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Dean gets kicked out of the Sublime Submission training school on his second day.

He sits in the waiting room, glowering at a potted fern, his ass throbbing in his jeans, and waits for his dad to come out of the business office behind the desk. The bright, cheerful signs decorating the walls--”Good Training For Healthy Dynamics!” “Real Results- Daily Levels Testing!” “Ask About Family Discount Packages!”-- get a sneer and a curled lip. Fucking Doms and their fucking posturing. It’s not Dean’s fault he’s bigger and stronger than half of the trainers here, or that he’s old enough to vote, while most of his classmates are just past puberty. They definitely weren’t prepared for him, he thinks, and smirks.

“Dean.” His eyes snap up and he sees the weary frustration on John Winchester’s face, and for a second he almost feels sorry. Then he stiffens up his spine and glares at the short Dominant standing beside his dad--that little blond dude had paddled him raw once the fight had been broken up--and stands up.

“Can we go?” He knows his tone isn’t properly submissive, but Dean’s never been a proper anything, and he isn’t gonna fucking start now.

John puts a hand on the back of his neck, big and warm and strong, and Dean lets out a breath, but doesn’t drop his eyes, doesn’t fall to his knees, none of that bullshit. He just waits.

John sighs. “Yeah, kid. Let’s go home.”

Home is a small, tidy ranch in a blue collar neighborhood outside of Austin, and Dean leans his head against the window of Dad’s truck and watches the familiar scenery roll by, ignoring the heavy, uncomfortable silence. Even as he follows his dad into the house and tosses his jacket onto a chair, he doesn’t say a word. At least Sam’s still at school, so they won’t have an audience.

John settles into his recliner and pats his knee with another sigh, and Dean, feeling a little hopeful suddenly, hurries to his side, though he slumps to a seat on the floor by his feet, instead of into his lap. He’s too big for that kid stuff now. And his dad’s hand in his hair is one of his favorite things.

“Nobody was more surprised than me when you tested submissive, Dean,” John’s low voice isn’t angry, isn’t even frustrated anymore, and Dean just leans into his leg, taking comfort there. “The way you took to hunting, the guns, the fighting, I would’ve pegged you for a Switch like your mom and me, or even a Dom. And maybe it was my fault for keeping us all on the road after that. Maybe I should’ve settled down right then, left the hunt to someone else--”

“Dad, no!” Dean looks up, meets his eyes, appalled. That last hunt, almost three years ago now, the one that had actually killed the yellow-eyed demon, the one that had set them all free? That had been worth everything. And John still hunts, though they’re more local. Sam has his school, now. Dean graduated high school and has a job in a garage that he really likes. But man, hunting is the greatest. John hasn’t let him come along much recently, but Dean will show him that a Sub can be just as effective out there in the field, he knows it.

“I love hunting,” he goes on, when John just arches an eyebrow at him. “You know that. I want to get back out there, as soon as Sam graduates. I’m not gonna be some lame house Sub for some asshole Dom. It can be just like before.”

“Dean, it can’t.” He tightens his hand in Dean’s hair, cutting off the protest. “This isn’t working anymore, boy, and you’re too smart to pretend it is. I should’ve done better by you, I can see that now. You’re all over the place, and it’s getting worse, fast. You’re drinking too much--no, don’t lie, I know you are. Your mood swings are getting worse, you’re not thinking straight, you’re not eating or sleeping right. It’s not your fault, it’s your brain chemistry. You need a Dominant, a real one, to set you right. You need more than what I can give you, here.”

“We talked about this before,” Dean grouches, to hide the sick swoop in his belly at his Dad’s words, the confirmation of what he’d known. He’s failing, he’s not making the grade. “I agreed to go to that stupid training school, right?”

“And you broke one of the trainer’s noses on day two.” John shakes Dean’s head lightly with the grip on his hair. “Jesus, Dean.”

“They made us prance around fuckin’ naked. And he grabbed at my junk. It was instinct, okay?” Dean frowns at his dad’s knee, unable to meet his eyes.

“No, that wasn’t instinct. That was you refusing to listen to instinct no matter what. And you signed the consent form, you agreed to the training program. I don’t know why you’ve gotta fight everything so hard, kiddo.”

Shame tightens its claws into Dean’s gut. A disappointment, again. Just like when he tested Sub, just like every other time he failed to act “appropriately.” “Guess I learned from the best,” he mutters. He hates being a Sub. Hates it with every fiber of his being. Hates the knowledge that he’s biologically wired to crave touch and comfort, boundaries and rules and guidance. That some part of him needs to be under a Dominant’s control, wants to be owned and subjugated. That somewhere in his brain is a time bomb of chemistry, that, if he doesn’t get to properly submit, reach subspace, and give up control, might just drive him crazy.

Lying in bed that night, listening to the tinny music from Sam’s radio through his bedroom wall, he feels the hot, itchy knot of anger that’s been growing in his chest for months grow bigger with every breath. Fuck submitting. Fuck all those ads with the pretty, barely-dressed subs on leashes dancing through the daisies at the heels of their tall, gorgeous dominants in leather. Fuck society in general, Dean thinks. As soon as he can, he’s grabbing his old gearbag and getting back on the road to hunt. The monsters never seemed to care what his designation was. He punches his pillow and rolls over and tries to sleep.

Chapter Text

The door slamming wakes Dean out of a heavy, unrestful sleep. His room is too bright and too hot and he stares groggily at the alarm clock, wondering why it’s so late, before remembering that he was supposed to be at sub training school today, so he won’t have a shift at the garage. Or is it Saturday? Fuck, his head is fuzzy.

“Sam! Get me some water!” he shouts, not bothering to get up.

“Get it yourself, jerk,” he hears Sam from downstairs, and grins. Damn, he loves that kid. And hearing his voice squeak now that it’s started breaking will never not be hilarious.

His door creaks open a few minutes later, and Sam’s messy head peeks in.

“Dad says to get up and wash your face and brush your teeth, he’s got somebody in his office, he wants you to meet him,” Sam gets out. Dean grunts into his pillow. “Seriously, Dean.”

“Seriously, Sam, I don’t care.”

“Your butt is already pretty red,” Sam says, in that judgy, snooty way that only teenagers can really pull off. “You really sure you wanna be this obnoxious?”

That gets Dean to sit up. “Obnoxious or not, I’ll beat your ass till it blisters if you ever mention mine again,” he growls at his brother, who yelps and disappears around the door again. Dean sighs and scrubs his hands through his hair, staggers to the bathroom, and takes care of business. He does wash his face and brush his teeth, because nobody deserves his morning breath. His dad hadn’t said anything about clothes, though, so when he eases down the stairs and through the kitchen, he’s still in his bright red SMU boxers and a threadbare Mechanics Do It Better t-shirt Sam had gotten him years ago for Christmas.

He can hear voices. His dad’s low bass rumble, and a similarly deep answer, but the stranger’s voice is sharp, almost angry? Definitely not pleased. Concerned, Dean slides through the office door. Maybe this is more fallout from the training school. Maybe he should have put on pants.

There’s a dark-haired man standing beside his dad at the desk, and they’re looking through a stack of papers. Both of them look up at him, and he’s pinned for a quick moment before he forces himself to keep moving. His hunter instincts are tingling like crazy, dangerdanger. The stranger is slim, shorter than John, maybe even a little shorter than Dean, but broad-shouldered with messy black hair and hooded, intense blue eyes. He’s wearing black dress pants and a pale blue shirt with the sleeves rolled up, but he doesn’t look casual at all. Every inch of him screams Dominant, in a way Dean just isn’t ready to deal with right now. John’s face isn’t giving anything away when Dean glances at him, but his eyes have a look in them Dean doesn’t understand.

“Hey dad, Sam said you wanted me?”

“Have a seat, Dean,” his dad says, and his voice sounds tired, strained, and Dean’s throat tightens, but he refuses to show weakness to strangers. He saunters in and throws himself into the free chair, looks expectantly up at his father. John drops a warm hand onto his shoulder.

“This is Mr. Novak. He brought over some of the test results from the training school. He has a proposal for us, for me, and I think...no. I know, it’s a good idea. He’s going to explain it now and you’re going to listen, you hear me?”

Dean shoots an incredulous look up at his dad. Like the school idea had worked out so well? But whatever, he owes his dad for messing up there, so he shakes his head with a smile.

“Sure, Dad. Hit me, Mr. Novak.” When he meets the man’s eyes, though, the smile falls off his face. Mr. Novak is...not amused. In fact, he’s frowning. Not just angry, but disturbed, concerned, maybe even upset. But he starts talking, after a beat.

“Dean Winchester. Nineteen years old. Tested as a low level submissive at age fourteen in a routine school physical in...Phoenix, Arizona.” Novak flips a page over, and Dean sighs. His voice is nice, rough and deep, but he’s not telling Dean anything he doesn’t already know. “Current Dominant of record and responsibility is John Winchester, father, high-dominance Switch.”

“I’m an adult,” Dean breaks in there, unable to stop himself, though John’s hand tightens painfully on his shoulder. “I’m responsible for myself.”

Novak’s eyes snap up to his, frowning, severe, but he doesn’t respond directly, just continues his recitation. “Nine complaints of antisocial behavior in the last six months. Seven official reports of aggressive or taunting behavior towards Dominants. Two citations for public intoxication and fighting.”

Dean tries to stand up, but his dad’s hand is like iron. His face is hot, burning, and he can feel his breath speeding up, that prickle of anger burning even hotter now. “Who the fuck are you--”

“Dean.” His dad’s voice isn’t loud, but there’s something terrible in it, and for once, he listens. Shuts up and sits still.

Novak glances at his dad, then back to Dean. He’s impassive, his voice is calm, almost monotone, when he keeps talking. Dean already hates him.

“Normally, this would be a case where the authorities might require some supplemental training for the familial Dominant of record, to be sure the Sub’s needs are being met at home. But when Dean was tested in pre-admission at Sublime Submission, there was an...incongruity. His results did not match the application. They retested his blood samples. When it was confirmed, the management there contacted me to deliver the results.”

He’s looking at John now, like Dean isn’t even there. “Dean is a high level submissive. He’s right at the top of the charts for just about every metric. In addition, his stress markers are dangerously elevated. Adrenaline, subutanol, lactic acid are incredibly high, and dopamine, rewardarin and serotonin are almost undetectable. I’m honestly not sure how he’s still walking around sane.”

What...this can’t be possible...The blood is pounding in Dean’s head and ears so hard he can barely hear his dad speak.

“I’m still not sure how that’s possible? The school tests are accurate, they assured us. I called after we got the results to confirm, Dean never seemed submissive--”

“My best guess is that your unusual circumstances were affecting his results. You explained some of your life on the road. It was very structured, yes? Almost military? And he was raising his brother, you mentioned. That kind of discipline, service, sacrifice, would have fulfilled him, even so young, unusually so for his age. The school tests are fairly bare-bones, so lack of the stress markers would have just been noted as an absence. And he hadn’t yet reached sexual maturity.”

“Still,” John shakes his head. “Dean’s always been pretty assertive.”

“His orientation is actually fairly rare,” Novak answers, and his voice has some urgency in it now. “Higher level Dominants and Submissives are often mis-identified early on--”

“Oh my god,” Dean says, his voice weak in his own ears, and then he fights off his dad’s hand and he’s standing up, rage rushing through him. “What the fuck? What the fuck! Dad, don’t listen to him! This is bullshit!”

“Dean?” Sam’s standing in the office door, he’s heard Dean’s shouts, fuck, this is just what he needs, the kid hasn’t even tested one way or the other yet--

“Sam, get out and shut the door--”

“Dean, sit down, right now!” that’s his dad, but he can’t listen, can’t--

“Sammy, go!”

“Dean, are you okay?”

“QUIET.”

Everything stops.

Mr. Novak looks pissed. And that voice had come out of him. Dean couldn’t speak if he wanted to, not in the face of that kind of authority. It’s like that voice reached down inside him and yanked his attention right out of him, and he staggers a little as he turns to face him.

“Dean Winchester, your father has agreed to sign over your papers to me. While in these circumstances it is not strictly necessary, I would prefer that you also sign the transfer and come with me willingly today.” He folds his arms and stares at Dean.

Dean’s heart shatters.

“Dad?” he whispers.

“Dean. Son.” His dad grabs him, turns him around, looks in his eyes. John has tears standing in his eyes, and that’s not right. “Mr. Novak trains...well, he specializes in submissives with troubles. Difficulties. I checked him out, he’s good. He’s the best. You need help, boy, or I’m going to lose you, and I can’t lose you. He’ll help you come to terms with this, get healthy, so you can have a good life. Please. Dean, for me. For Sammy.”

That’s not fair, that’s not fucking fair, and then he feels skinny arms wrap around him, and Sam’s there too, and Sam’s sobbing, and Dean knows he’s going to go. He’ll go.

Chapter Text

Novak’s house is big, and took two hours to get to and it’s in the middle of nowhere, and that’s all Dean’s mind can process when Novak’s bland sedan pulls up into the circular drive and stops in front of the big wooden double doors. He grabs his bag and slides out of the door when a man in a suit holds it open--of course a place this big has servants--and stands looking around carefully until Novak steps up beside him.

“Inside, please, Dean.” The voice isn’t demanding, isn’t requesting, isn’t anything but neutral, and that allows Dean to walk up the shallow curving steps and in through the doorway.

The entryway is large and plush, with cabinets and even chairs, coat racks, shoe racks, and another set of doors at the far side. Warm wood and thick persian carpets make it feel more like a living room, and Dean’s never seen anything so fancy.

Novak is hanging his coat on one of the hooks, and when he sees Dean hesitating near the door, he actually smiles a little.

“Have a seat. We’ll talk a little before we go inside. I want to be sure everything is clear to you before anything begins, and give you a chance to ask any questions, get any concerns and fears out on the table.”

“I’m not afraid,” Dean blurts, scowling, his first words since leaving his house, and Novak cocks his head consideringly.

“Mmm. Indulge me, then. I expect you would at least like to know the rules of the house? Ignorance is very much not bliss, in this particular case.”

The bastard has to be sarcastic, of course. Dean flushes, still angry, and nods jerkily. He’d promised Dad and Sam he’d try, so he stomps over to one of the chairs and sits, his bag still clutched in his hands. Novak sits across from him, so close their knees nearly touch. It’s not comfortable, but Dean can’t move now.

“Thank you,” he says simply, and then sits back. Calm as anything, as if they’re just having a normal everyday chat. “I think we got off on the wrong foot, though in these circumstances, the right one is difficult to find. I’m Doctor Castiel Novak. I’m thirty-two years old, a high level Dominant, and I am on the board of ten Dominant and Submissive training schools across the state. I specialize in high-risk, high-urgency individuals, and when one is found, I direct them to appropriate resources, or assist them myself if it’s a good match. You are not the first initially mis-oriented individual I’ve helped, so I do have some experience. Now, please introduce yourself.”

Dean folds his arms across his chest.

“Dean Winchester. Nineteen. Mechanic. Sub. I’m here because I promised my Dad I’d try this, so I don’t end up in a psych ward or whatever, like those PSAs they made us watch in high school.”

Novak smiles a little when it’s clear he won’t be expanding on that, his too-blue eyes keen on Dean’s face.

“All right. A man of few words, I see. I won’t press for more right now. When you signed the Emergency Transfer of Responsibility papers, you agreed to enter my care for the purpose of training in Submission until fully rehabilitated. Now that I am your Dominant, there are rules you will follow and expectations for your behavior while you are in this home. I am fairly Traditional in my lifestyle, but I have found that my methods are fair and work well. Dean, look at me.”

Reluctantly, Dean lifts his eyes from where he’s been glaring at the carpet, and he sees actual sympathy in Novak’s face for the first time, and somehow, that makes everything worse.

“I will be learning you as we go, and making sure everything is working towards the goal of your acceptance of your Submission. Adjustments can be made. But the rules are non-negotiable. Do you understand?”

There is iron under that soft tone. It feels like a fist at the base of Dean’s throat. But Dad trained him to be a soldier, and some stupid rules aren’t going to break him. He nods firmly, because he can’t speak.

“Good. There are plenty of small protocols you’ll learn while you’re here, and we will get to those eventually. The first rule is that Submissives do not wear clothing beyond that door,” he indicates the inner door of the entryway, “in my home. You can hang or fold all clothing on a shelf or hook here, and the staff will take it away.”

Dean chokes a little. His stomach sinks and he rubs his hands over his jeans, palms suddenly sweating. He’s been stripped before for scenes, of course. Even spent a whole weekend nude with one really kinky Switch. But all the time?

“Naked?” He gets out. “Completely?”

“At all times,” Novak confirms, and this time the smile is hard. “Unless I dress you in something myself, you will be bare.”

“But-”

“Second rule. You will address me as Sir. As you meet the staff, you may address them by name. You will treat everyone here with respect. Your manners are terrible, but we will be correcting those in the coming weeks.”

Dean scowls at him.

“You try learning manners in a muffler shop. Sir,” he belatedly remembers.

That actually gets him a grin. Novak’s eyes even crinkle up a little at the corners, and Dean has to admit, grudgingly, that the guy is hot.

“I’m not blaming you, Dean. Just stating facts. Third rule. You WILL obey me. I will tell you to do things you do not wish to do. I may even make you do things that frighten you, or that you hate. But I give you those orders, in word or in action, for good reasons, and you will obey me, or you will be punished. This is not part-time, and there are no exceptions. Is that clear?” Novak leans forward, and meets his eyes, deadly serious.

“Yessir,” Dean mutters.

“Good.” Novak stands. “Those are the big three. Clothes off, and leave your bag. I’ll show you
the bedroom, and give you a tour of the house. We’ll get your intake exam over with, and then it’ll be nearly dinnertime. I hope you have a big appetite, Francesca loves cooking for more than just me.”

It’s all so strangely normal, so suddenly, it’s giving Dean whiplash. His hands shake as he strips off his jeans and t-shirt, then slowly, his boxers. For Sammy, he reminds himself, as he shoves his clothes onto a shelf with his boots and bag. Bare as the day he was born, feeling far too vulnerable and exposed but refusing to shield his cock with his hands, he squares up his shoulders and walks to Novak’s side.

“Very nice,” Novak says, looking him over. “Now follow behind my right shoulder. I want you no more and no less than one step behind.”

Dean’s lip curls. He knew it. Novak is one of those assholes. Not just ‘fairly Traditionalist,’ but believing that Subs are second class citizens. No better than children, or livestock, who need to be sheltered in the home. Fuck. But he falls into place as best he can without saying anything, and follows Novak into the frankly ridiculously opulent home.

He can barely take it in, because he’s so aware of his nakedness. Even though he knows he’s big, muscular, it is a strangely vulnerable feeling to be in this strange place with nothing to shield him. His cock is trying to climb up into his body, but at least that makes it easier to walk behind Novak as he leaves the big parlor and moves towards the back of the house. A stunning young woman in a dark dress comes to them in a hallway with a big smile, and when Novak stops, Dean almost crashes into his shoulder.

“Dr. Novak! Welcome home, and I see you’ve brought someone with you!”

“I have indeed. Meg, this is Dean. He’s with me for readjustment training, and we have a lot of work to do. Dean, this is Ms. Masters, my second in command and office manager and right hand woman.” He smiles at her. “Meg, make arrangements for Dean at dinner, please? I’d like to get his intake done first.”

Dean shifts warily at that. Intake? This isn’t a hospital.

“Of course. Welcome, Dean. I know you’re going to love it here.” She nods at him but doesn’t try to shake his hand or touch him, and she hustles off back down the hallway. Novak just keeps walking, and leads him into a small, warm room with a low table and some chairs, and a little desk with a computer.

“Up on the table, Dean.”

Curious enough not to protest, Dean hops up, leaving his legs swinging. He tries to watch over Novak’s shoulder as he logs in and does something or other on the computer, but he can’t really see.

“Now, I need some sexual history from you. You can speak freely in this room, though I do still expect respect and honesty.” He comes to stand next to Dean, and for the first time, touches him, a warm hand on his back, between his shoulderblades. Dean can’t help it, he flinches.

“Shh,” Novak says, calm. “Nothing will hurt, right now. I’m going to touch, and ask questions. And you will answer.” He moves his hand, long strokes, while his other palm comes to rest on Dean’s sternum. Dean tamps down the urge to fling them off and punch him in the face.

“When did you lose your virginity?”

“When I was sixteen.” His voice sounds tight. He’s so angry, suddenly, he can’t help it. It’s like a tornado in his brain.

“Give me details. Man, woman? Dominant, Sub, Switch? Did you penetrate, or were you penetrated, or both?” Novak’s hands won’t stop moving.

“W-woman,” Dean grinds out. “Switch, I fucked her. Stop that!” He jolts backwards, away from the hands that are now curling down to stroke his belly.

“Do you need me to restrain you?” Novak doesn’t seem angry, but he also isn’t stopping. He crowds closer, in fact, pinning Dean who has no leverage, and now both of his hands are rubbing Dean’s belly, fingers just barely dipping into the crease of his thighs, where his limp cock is trapped against the table.

“No, I need you to stop. I thought you were taking some kind of medical history.” Dean’s jaw is clenched so tightly he’s afraid a tooth might break. He can feel sweat breaking out on his face, his shoulders.

“I think you need to accept and understand that I can touch you however I like, Dean,” Novak says above his head. “Anytime I like. Relax, accept. Submit. Let it go. We’re just beginning, don’t wear yourself out already.”

Dean chokes a furious little breath out and tries to force the red rage out of his mind. He succeeds at least a little.

“When was the last time you had a successful session with a Dominant?” Novak asks, his hands still moving, now holding and shifting him a little, moving Dean’s hips forward on the table.

“A-about six months ago, I think. Since then, I, my dad. I kneel for him. It calms my head some.”

“Does your father dominate you sexually?”

“Jesus christ, no! What the fuck!” Dean twists in the circle of Novak’s arms, but he’s trapped, and the hands on his hips pin him still.

“Shh, no.” Novak’s voice is still calm. It’s actually pretty soothing, now that Dean is listening to it more. “He was your Dominant. It would not be unusual, or wrong, with you in such distress, for the orientation to override the family bond. It’s okay, Dean.”

“He doesn’t.”

“All right. Lie down now, please.” Dean does not want to lie down, not at all, but he finds himself following that command until he’s flat on his back and he’s staring up at the soft lights in the ceiling. “Your signals are crossed, in your head. Your fight or flight instincts have been firing for so long they can’t differentiate between real threat and dominant partner anymore. So we’re going to have to rewire some things. I’m going to give you a little relief now, so you can start to hear me.”

“What kind of relief?” Dean’s head is fuzzy, he still has all that anger, but he’s both wary and curious. Is this guy gonna jack him off on the first day?

“Every Sub has special glands in the groin, the anus, the back of the neck, and the breasts.” Novak’s typing something, and there’s a little prick of a needle on his finger that he barely notices. “Just taking some blood, nothing to worry about. These glands affect orgasm, but also release neurotransmitters and hormones that help a Sub’s health and well-being, and reward true submission. Normally, once a Sub is sexually mature, regular intercourse and relations stimulate them sufficiently, along with proper brain chemistry and subspace. In your case, I’m going to manually express them. Just relax.”

Dean knows about the Angel Glands. Everybody does, they’re the topic of all kinds of leering schoolyard jokes and urban legends. But he still jerks when Novak’s hands spread his thighs wide.

“Relax,” Novak says, more sternly, and Dean growls. “I am being extremely lenient with you because it’s your first day and this is all new,” and now Novak is looming over him, and his voice is still calm but with that steel undertone again. “But I do have a line, and you are about to cross it. I will restrain you if you cannot control yourself.”

“Yes sir,” Dean snarls, and it must be close enough, because Novak’s hands are on him again. This time with purpose. He feels thumbs running up the insides of his thighs, right up to the root of his cock, and they circle there like they’re searching for something, and then they press in, firmly, towards his pelvis.

FUCK it hurts. It hurts like the knot in a pulled muscle getting kneaded, hurts like a really deep scab getting pulled. His hips jerk and jump and he thinks Novak is saying something, but he can’t hear over the rush of blood in his ears from the incredible pain and then a core-deep give, like the moment before orgasm, and the relief and release is so heady he moans out loud, from his gut, going limp.

“Good boy,” he hears in a deep hum near his ear, “oh, that is wonderful, so good, what a good boy,” and somehow the words add to the flood of warmth and pleasure and satisfaction that’s tingling up his spine and all the way to his fingers and toes. When his knees are gently bent and his feet put flat on the table he goes with it, why not, and then he can tell Novak is sitting on the table by his side, warmth and solidity there.

“No wonder you’re fighting so hard,” Novak murmurs. “I’ve never seen glands swollen like that. You’re a wonder, Dean.”

“Winchesters’re tough,” Dean slurs in answer, lolling his head to the side so he can see Novak’s face. He’s smiling a little.

“Indeed you are. We’ll finish up the questions so you can rest before dinner. Have you ever been anally penetrated by a partner?”

He’s so straightforward about the questions, Dean almost can’t fight through the haze of good feelings to be embarrassed.

“Uh, few times. Fingers, got fucked a few times by another sub and a switch, I was curious.”

“Were you able to orgasm from anal penetration alone?”

“Not even close, dude.”

“I know we are informal right now, but do not call me that. I will put your ‘sir’ restriction back in place here if I find it necessary.”

“Sorry.” Dean’s a little distracted. Novak has started stroking his chest, circles around his nipples, firm and probing like he’s feeling for something. Here and there he digs in a little with the pads of his fingers, and it sends a bolt of something tingly right to Dean’s spine.

“Do you find pain sexually arousing?”

Dean has to think about that one.

“No? I don’t think so. I never really enjoy it.”

“All right. Are you stimulated by the feeling of being humiliated?”

“No, definitely not.” Dean hasn’t let anyone do that, but it doesn’t sound like something he’d be into.

“How often do you masturbate to orgasm?”

“Used to be every day. Lately, uh.” Dean tries to think. “Every other day? Maybe longer. I dunno.”

One more press of those clever, long, warm fingers and Dean’s moaning again, eyes closing as that rush of something, whatever it is, floods through him. His skin feels alive, from his scalp to his toes, and he has to shake his head to clear it.

“I think we will focus here for now,” that calm voice is saying, and there’s a firm, no-nonsense pressure on his hole. He flinches his thighs together weakly. “No, stay open, good boy. Never hide yourself from Sir. Good. Relax.” The thumb-he thinks it’s a thumb--presses into him dry and it burns but it’s muted, quiet behind the good-warm-good-yes rush. “Good boy. Just a small stretch for now, one more sample, and we’re done.” He’s never felt like this when someone touches him there, never, he’s shivering with reaction, overwhelmed by too much conflicting sensation. “Well done, Dean. Relax, now. Breathe deeply, put your legs down. Stretch. Lie still while I type my notes.”

It’s easiest to just follow directions, right now. It’s been a long day, after all. And whatever that cocktail of acupressure-whatever Novak has cooked up in him, it feels freaking amazing, and Dean figures he deserves to wallow in it for a while.

Chapter Text

When he gets his mental feet back under him a little, he’s not sure how much time has passed, but the typing he was barely aware of has stopped, and Novak is sitting beside him. He’s got a hand on Dean’s belly again. Dean feels sore and wrung out, like he’s been on one of Dad’s training runs and then crammed for the SATs, but he still realizes that’s weird.

“I can’t get pregnant, you know,” he says before he can think, and Novak just slants a judgemental look down at him, then pats him.

“Welcome back. I’ll show you to our bedroom. You can shower and rest, we have about two hours before dinner. Slide down, slowly now.” He keeps a hand on Dean until he’s on his feet, and Dean feels a flare of that sullen anger again. He’s not a child. He’s not fragile or weak. He barely keeps the response in, though, and follows Novak back through the maze of rooms and up the long staircase.

“This is our room.”

Dean blames the bugfuck insanity of the day for the fact that he only just now registers the phrase.

“What do you mean ‘our room?’ Where’s my room?”

“We will be sharing a room and a bed while you are here with me,” Novak says serenely, and pushes him into the room.

It’s large, like the rest of the house, and warm, like the rest of the house. Thick, plush carpets stretch nearly to every wall, in blues and greens that complement the cream walls and three huge windows. The bed is enormous and has four big wooden posts and mounds of blankets and pillows. There are padded benches and chairs and a deep, plush couch and even a fireplace, and Dean can see a bathroom through a side door that looks decadent. But--

“No way. No, no way. You’re supposed to be my trainer, not my boyfriend, I’m not sleeping with you! That’s insane!”

Novak looks at him levelly. Goddammit, doesn’t the guy ever get mad?

“I would prefer not to have to correct you before dinner, Dean. It’s your first day and you are tired. There are shower things in the bathroom, you have ten minutes.”

“It’s bad enough you’re gonna fuck me! You’re gonna do that, right?” Dean bares his teeth at Novak, bristling up all over. “For my own good or some bullshit like that?”

He doesn’t even see Novak move. His arm is twisted behind his back in a classic come-along hold and he’s shoved firmly against the arm of the couch. He kicks one leg back but hits nothing, and then the pressure threatening his shoulder joint makes him go still and bend at the waist. Fuck, he’s out of shape and off his game. So far from hunter form, he should be ashamed.

“There is one of these in every room.” Novak’s voice is still calm, and a hand holding a three-foot wooden switch, thin and whippy and nasty looking, is in front of his face. Dean hisses between his teeth. “I prefer to discipline at the time of the error, so that the crime and punishment are more closely linked in the Sub’s mind. For larger infractions, of course, there will be larger consequences. You will take five with the switch for disobedience and disrespect. Say yes, sir.”

“Yes, sir,” Dean growls. He wants it over with. And out of all the parts of being Submissive, this is weirdly enough the one he’s most okay with. He was pushing, he knows it. That was totally across the line, and he’s gonna get punished for it, which he deserves and has earned fair and square. If Novak is a decent guy--and so far he seems okay--that will be the end of it, and they can both move on. Dean likes that kind of straightforwardness and clarity.

“Do I need to keep restraining you?”

“Definitely, sir.” He thinks he feels Novak sigh against his side where they’re pressed together then, but the moment after that, the sssmack of the switch hitting his backside lands. First the sound, then an ice cold line of impact, then burning pain so harsh his hips curl up and in reflexively, trying to escape. He sucks for air, desperate not to make a sound.

“Breathe, sweetheart,” Novak says quietly, and smack, there’s the second one, and Dean gulps his breath like it’s water. It’s agony. His dad has never whipped him so hard. No one ever has. Sssmack, the third, he’s chewing his lip raw. Sssmack, four, his hips twist in a silent, desperate heave, but he’s pinned down firmly. One more, he chants in his mind, one more one more one more and ssssmack, the last one is right in his sit spot, and he hasn’t made a sound, he didn’t break, he hasn’t--

Novak doesn’t praise him, doesn’t lighten the punishment with petting and sweetness like his dad always did. He helps him up from over the couch, though, and looks at him closely as he pants and shakes, running a thumb over his chewed lip with a smile that’s almost sad. Dean’s eyes are burning, but they’re dry. He hasn’t cried in five years and he’s not going to start now.

“This is our bedroom,” he says after Dean's breathing has steadied out some, holding Dean’s chin in his hand.

“Yes sir,” Dean says.

Chapter Text

Castiel beckons Dean forward at the door of the small study where he knows Meg has set dinner for the two of them. The boy had showered, sullenly, and then collapsed (on his belly) into unconsciousness in the bed for over an hour, as Castiel had predicted. He’s clearly exhausted, and clearly run right to the edge of sanity, but he’d woken up just as feisty as before. Castiel can already see improvement, though. His shoulders are lower, more relaxed, and his breathing is deeper. He is easier in his skin, less self-conscious, and moves more gracefully.

Castiel has to hide a grin as he watches Dean sweep the room with his eyes until he locates the switch in its custom stand, right by his own chair, near the table. Good. He’d been hoping to make an impression with that. He slides a hand down Dean’s back to stroke over the raised, angry red welts striping Dean’s bottom, just to watch him jerk and hiss.

“I hope I can count on you to mind your manners during dinner?” It’s not really a question, but he can already tell that with this one, it’s best to keep him engaged. He ignores the resulting glare, and guides the boy forward with the hand on his back, right through the resistance when Dean spots the cushion beside his chair. The boy’s father had done him no favors at all, treating him like a Switch. Every natural, healthy submissive behavior is a battle for Dean, and it’s heartbreaking.

“I’m not a dog,” Dean fires at him, big green eyes snapping with anger, his hands in fists, standing stiffly beside the cushion.

Castiel allows his surprise to show.

“Of course not. You are a Submissive, a precious and cherished human being, and a man. Who may kneel on your pillow for meals, as is proper and appropriate, so I may care for you.”

Thrown off his stride, Dean blinks at him. It’s enough of an opening for Castiel to reach out and cup his face with a smile, even as his other hand takes hold of Dean’s soft penis in a firm hand and exerts strong pressure downward. “Kneel,” he says firmly, as Dean yelps as his knees buckle instinctively and he collapses down to the pillow. “Good boy, well done, good,” he praises softly. He will move into every crack in that armor and fill the space behind it with praise and pain, pleasure when earned, and although Dean probably feels anger right now, Castiel can see the slight widening of his eyes, softening of the angry line of his plush mouth, the fractional tip of his head, as the praise hits the submissive centers of his mind.

You can’t fight biology. Castiel knows it. Dean will learn. He takes his seat, and beckons Dean closer.

Sighing like it’s a terrible imposition, Dean scootches closer on his pillow, until he’s right by his side. Castiel drops a hand onto his head, combing through the honey-brown strands, soft and cool from his shower, still.

“Please cut the steak and vegetables for hand-feeding,” he informs Benny, who is setting dishes onto the small table for them. With a smile, the big man nods, even as Castiel returns his attention to Dean, who’s now blushing and scowling, clearly uncomfortable naked and kneeling in front of the staff. The poor boy is so conflicted.

“Dean. Dean, look at me. While dinner is cooling, do you want to know your daily schedule? I think most of it will be interesting for you.” He smiles down into green eyes that open, clearly despite themselves.

“Sure. Sir,” it’s hastily tacked-on, but not forgotten. He can see wheels turning, almost smell the smoke. Of course Dean, so used to independence, will want as much knowledge as he can get. Knowledge is power, and Dean hates weakness.

“The first few weeks will be very flexible, but roughly, we’ll try to keep to this. I wake at seven every morning. I wake hard, so I will use you for my pleasure. You will not orgasm.” Dean’s eyes go huge, then narrow with the rage of his unbalanced brain chemistry, so Castiel pops a piece of too-hot steak into his mouth before he can say a word. Dean chokes, and chews. “This is not a debate, Dean,” he warns, low. “I am more than willing to place more stripes on your bottom tonight.”

Dean winces and nods, swallowing thickly. Hmm. Food may be an excellent tool. Castiel makes a mental note, and feeds him another cube of steak. The boy is clearly starving, and takes it eagerly, despite his distaste for kneeling, earlier.

“We will shower together, and then we will test your blood levels, and eat breakfast. You will then spend an hour with my masseur.” He smiles as he sees Dean perk up a little at that. Perhaps the boy thought it would be all beatings and chains in the dungeon? Dean makes a face at the asparagus spear that Castiel feeds him next, but doesn’t overtly protest.

“After that, exercise. I can tell you take pride in your body, it’s a work of art. That’s a wonderful thing and I support it completely, so please take advantage of that time as well. You have full access to my home gym. I run, myself, and train. You are welcome to join me, or train alone. Of course, when we are not together, you will be placed in chastity.”

“What-” Dean gets out around another piece of steak, a thundercloud on his brow, and Castiel strokes his cheek gently.

“Don’t speak with your mouth full. Sexual pleasure is a reward, Dean. It is earned with good behavior, here, and will be granted or withheld by my hand alone. It is a gift from a Dominant to their Submissive, and it is only one of many kinds of pleasure that true submission can give. You will learn all of them.” Perhaps it’s cheating a little, but he cups the back of Dean’s neck and unerringly finds the swollen gland there, at the top of his spine, and rubs it gently.

Dean’s eyes go hazy and he sways on his knees. His cock stays soft, as is appropriate.

“Why can’t you just do this? Why all the other stuff? Sir?” Dean gets out, and there’s a distinct complaint to his voice, almost a whine. The boy is so tired. Castiel keeps petting him.

“This is just a band aid. A shortcut. Without subspace, submission, real surrender, it makes you feel nice, but it’s not a long-term fix for anything,” he answers easily.

“Hate this,” Dean mutters, almost to himself, and Castiel knows they’ll need to get to the bottom of that eventually, where it came from, and the root of the poison. But for now, his boy needs to eat.

“You’re too thin, sweetheart. Eat. Here.” Dean looks up eagerly, and takes the next bite of steak with gratifying quickness. Castiel eats a few bites himself, and drinks his water, before moving on with the schedule.

“After lunch, you will rest for an hour in bed. You may read or sleep, but no television or other distractions. The three hours after that will be spent in the training room with me. We will be working on standard Submissive training, as well as some programs of my own that I’ll tailor to you once your kinks and preferences become clear.” More food for Dean, who’s clearly interested despite himself.

“Then after dinner you have free time. You can call your family, watch television, and once you’ve proven you can be trusted, I’ll be happy to take you into town in your collar and leash for any errands you would like to run.” There’s that thundercloud again, but Dean’s mouth is full again, and he’s too smart to let a warning hit twice. Especially with how badly his bottom must be throbbing by now. Castiel smiles with pride. God, he’s gorgeous. Full of fire, and once he’s healthy, he’ll be the most stunning Sub anyone’s ever seen.

“Bedtime is ten thirty. You will present yourself for me on on the bed, and I will take you. If you’ve earned it that day, and if you can reach it through anal stimulation alone, you will be permitted to orgasm.”

At that, Dean goes pale, fear and anger chasing across his face. “Mr. Novak. Sir, I can’t. I’ve never-”

“You told me, I know. Dean, you can. All Submissives can, your body is built for it. We will work towards it together, hmm?” He calms Dean with a touch again, wincing internally at how engorged the glands are, how unhealthy the boy truly is. He’s never seen a Sub so unfulfilled be able to maintain control like Dean can; Dean’s strength of will must be absolutely extraordinary. Honestly, he was expecting to have the boy shackled hand and foot by now, simply for his own safety. His sexual history is starkly bare. He’s clearly never reached true subspace. Castiel would prefer to take his time, lead him gently out of danger, but for Dean’s sake, it may not be an option.

Chapter Text

“Did you mean it when you said I could call my family?” Dean’s reluctance to enter the bedroom is evident in every line of his long, lean body, and Castiel can tell he’s stalling, but he can’t not answer when he hears the genuine pleading behind the question.

“Of course. I’d never keep you from contacting your loved ones. This is not a prison. You’re not a slave, and I’m not your owner.” He pulls Dean into a loose embrace, and is startled all over by the full-body shiver the boy gives. Touch-starved, to a degree he’s rarely seen. Castiel resolves then and there that their interactions will all involve contact.

“Could’ve fooled me, sir” Dean grumbles against his shirt, and Castiel chuckles.

“Think of it like therapy. Naked therapy?”

To his shock, Dean laughs. Actually laughs. When he pulls back to look, there’s a genuine smile on Dean’s face, and Castiel’s heart stutters in his chest. Oh, this is bad, this is dangerous, but those huge green eyes, lit with laughter, the way his lips curve, and the arch of his cheek…

“Come on now. Into the bedroom. Dinner was shockingly late, and with the day we’ve both had, early bedtime is well-earned.”

Dean balks. Castiel insists. They enter the room.

“I don’t want to get fucked, I don’t like it,” Dean growls, resisting again, and Castiel’s cock starts to respond, hardening in his plain trousers.

“Sweetheart, it is happening,” he answers, putting a little steel in his voice. “I will help you, tonight, come here.” Staying close, he guides him to a padded bench near one of the walls. It looks innocent, the high top padded with quilted maroon leather, the thick legs framing deep shelves. “Here, up, on your belly. Right on the bench.”

Looking suspiciously over his shoulder, Dean leans his chest on it. It’s a little too tall, so Castiel lifts his hips with a little shove, getting him off his feet and onto the bench completely. His cock hangs off the edge by just an inch.

“Hey!”

“Dean.” It’s a warning, and Dean goes quiet, though every muscle in his body is set in tension. He’s clearly braced to endure, like with the switching. There’s no submission in him, no liquid surrender. Somehow, Castiel will get him there.

Moving quickly, his own arousal now insistent, he takes two padded cuffs from the lower shelf and before Dean can protest, cuffs him to the heavy arms of the bench. It has a core of steel, it’s heavy, and he knows it will hold and not tip. Dean snarls, yanks, then subsides. Castiel, for safety, binds his ankles as well. This first fuck is absolutely critical; it will establish their dynamic, lock his Dominance in for Dean’s Submissive instincts. It must be rough, it will be painful, but he will not have Dean injured by struggling.

“Gotta have me helpless?” Dean is talking a good game, even with his face pressed into padded leather and spread out like a meal, but Castiel can hear the thread of fear under the words. “You some kind of pussy who can’t take me like a man?”

With a sigh, Castiel fetches the switch, and shows it to Dean, silently.

“Sir! I mean, sir!”

“I know you’re frightened, but your rules remain in place no matter what. You will take one with the switch for disrespect. Say yes, sir.”

“Yes, sir,” Dean says, thin and tight, and Castiel brings the switch down sharply, right across his bottom where the curve is thickest and highest, biting back his own aroused moan at the snapping whip of sound, the instant rise of the red welt, the way Dean’s hips try to dig into the bench to escape, the hissing gasp of breath from the Sub. He pats that quivering pale hip, and sets the switch aside.

That seems to have knocked some of the temper out of Dean at least, and Castiel finally strips, folding his clothes neatly. One of the bedside cabinets yields a long, slim syringe and a bottle of lube, and he doesn’t try to be quiet as he pads back to Dean. The cool room of the air is soothing against his cock, angry and so hard, now, the Sub’s fear and pain stimulating his own glands and driving his personal kinks hard. He won’t always get to indulge so, he knows, but for now, he will enjoy it.

“You can’t put that monster in me, sir,” and now there’s real panic in Dean’s voice, his head is turned and he’s watching Castiel. Perhaps he should have blindfolded him and just let him feel, but…

“I will not damage you, Dean,” he assures him, a hand on his lower back, stroking the sweet curve of it. “It will be uncomfortable, yes. You are serving me without immediate reward in this. I will find pleasure in your body, and you may not enjoy it. But I will not harm you. Try to relax now. Take deep breaths. Focus on my voice. Let go of your resistance and submit. You’re so beautiful like this, bare and open. So lovely, Dean. You see how hard you’ve made me? How badly I want you? Shh, there.” He spreads Dean’s cheeks with one hand, presses the tip of the lube syringe to his little pink hole, and slowly works the syringe inside. Dean huffs and twists, struggling a little, hole spasming around the intrusion. “Easy, it’s lube. Trust me, you want this.” When it’s halfway in, he depresses the plunger, withdrawing as he empties it. Carefully coating Dean inside, wetting him down. “Good boy, you took that so well. My lovely Dean. Just a bit more now.”

He’s saved some for the rim, and slicks it thoroughly, stretching it gently with his thumb. Just enough so it gives, loses its rigidity, and he can feel the gland nestled a few inches inside the rim bumping gently against Dean’s prostate.

Dean’s breathing heavily when he checks on him. Eyes hazy green, looking back over his shoulder in Castiel’s direction, more or less. His cock is half-full where it dangles in the air, though Castiel expects that won’t last long. It’s a nice solid package, and Dean is probably quite proud of it, but Castiel’s interest is elsewhere.

He leans over, blanketing Dean with his body, riding the full-body shiver he gets as he licks and nips up his spine, lining himself up, his cock prodding blind and hungry between Dean’s cheeks until it finds that small furl of his opening. Firmly reining in his drive to rut in fiercely, breathe in the screams and tears and surrender and pain of his Sub, he fastens his teeth gently at the base of Dean’s neck, and presses the first few inches of his cock inside.

“Huh, huh, huh,” Dean grunts, arching as much as he can, caught between the burning stretch of his hole and the calming wave of endorphins from the bite at his neck. His muscles are already relaxing, instinctively yielding to the forceful intrusion. Encouraged, Castiel presses in another inch, relentless, then another. It’s wet, hot, and burningly tight, but there’s no rigid resistance that would threaten a tear. Castiel pulls out, and then thrusts in again, a little further than before, rides out Dean’s bucking heave of protest, his abortive kick against the cuffs. Opening a place for himself in Dean.

On his fifth thrust he’s fully seated. All ten inches of him in Dean’s body, in to the root, his mouth watering at how incredible it feels. That tight little hole is spasming frantically around the thick, rigid root of him, he can feel Dean’s pulse fluttering in the velvet heat he’s buried in. He releases Dean’s neck, he’s stimulating other glands now; stands up and holds Dean’s hips in both hands, and starts fucking in earnest. His hips snap forward and he groans with the pleasure of it, and again, and again, the way it punches a whine of breath out of Dean each time he buries himself to the hilt...

“I am so pleased with you,” he purrs, and watches the way the muscles in Dean’s lower back soften and ease. “You are heaven inside, Dean. Made for my cock. Perfect, tight, hot. So good for me. I know it hurts, I know, but you are taking it so beautifully. Every inch of you is lovely, and never more so than right now.” He lets go of Dean’s hips with one hand, still fucking in hard, and reaches around. His cock is long enough to hit all three sweet spots between Dean’s legs, but it’s been so long for the boy a little extra can’t hurt. He forks his fingers down and rubs harshly at the root of Dean’s flaccid cock, in time with his thrusts, and that gets a noise out of the boy, a low, animal grunt that sounds like it comes from deep in his belly as his whole body bows in silent supplication. Beautiful.

“Good boy. Good, beautiful boy.” He twists his hips a little, changes the angle, drives up and in. Gets impossibly deeper, and yanks Dean’s hips back to meet his own force. Over and over he sinks in, reveling in the pure dominance of the moment as much as the pleasure of the fuck.

“Please come, sir. P-please be done,” Dean begs, stutters out through clenched teeth, driven to it, Castiel knows, but it’s such a huge leap forward in progress, so far from the curses and invective from before, it deserves consideration.

“You’re doing well, Dean,” his own voice is rough in his ears. “I’m very pleased.” He speeds up, hammering hard into the gorgeous body he’s penetrating. He can see Dean’s hole, stretched and red and angry-looking, sucking in his cock as it drives into him over and over. The boy’s whole body jolts on the table with the power of it, and that’s enough to send him over the edge, holding himself deep, twisting and grinding himself inside as his balls empty and he pulses his seed into Dean, heavy hot spurts that nearly blind him with pleasure. Marking the Sub in the most primal way.

“Good boy,” he breathes, as he comes back to himself. Carefully, he pulls out, not missing the cringing flinch from Dean as come and lube drool out after him. A quick inspection confirms that there is no blood and no tearing; he had taken care that there would not be. Just painful, then, and new. He strokes Dean from shoulder to flank, petting and soothing him, lavish with his praise. Tying his words and the flood of feelgood chemicals coursing through Dean to the act they just completed. “You are a wonderful Submissive, Dean. So strong and good for me. I am so proud of you, and so pleased. You took that so beautifully. On your first day, too. Well done, sweetheart. Here, let’s get these loose.”

He unbuckles the wrist restraints first, then the ankles, and half-lifts Dean from the table. The boy staggers a little when he reaches his feet, but Castiel holds him steady. His face is white, except for two spots of high color on his cheeks, and his eyes are so very green, though they are dazed and vague, his pupils blown huge. He’s shivering all over, obviously overwhelmed, and not making a sound. Normally, Castiel might be concerned about reactions the morning after sex this rough and unwanted, especially with a Submissive this rebellious and resistant, but this is truly the closest to subspace he's ever seen Dean. He thinks Dean will probably feel pretty good in the morning. “Here, sweetheart. Into bed. You have earned a good long sleep. I’m so proud of you.”

Dean is tall, slim-hipped and wide-shouldered, still rangy with lingering youth, but his shoulders and arms and thighs are heavy with muscle. Still, it is easy enough to move him into bed and ease him under the covers, and Castiel slips in beside him after cleaning himself up, dimming the light. He won’t hold the boy, not until he’s more knowledgeable about his sleeping habits, but he will be there. When he feels Dean hesitantly slide up against him, seeking contact, he smiles to himself, and settles in, eyes closing.

Chapter Text

Dean wakes up slowly, comfortable and confused. He feels--good? Almost like the mornings when he’s managed to have really good sex. He’s a little too warm, lying on his side in a pile of warm blankets, but as his brain gradually comes back online and he blinks his eyes open, he discovers his head doesn’t hurt, for once. He doesn’t have the usual sour taste of acid at the back of his throat. No stomach cramps means he was able to eat a real meal last night, that’s awesome, and he yawns, and reaches for a stretch--and freezes.

Everything south of his waist aches as soon as he moves, and it all comes back.

There’s a low chuckle behind him, amused and a little dirty. “Good morning, Dean. How do you feel this morning?”

Novak is behind him, but weirdly enough, he doesn’t feel threatened. Ignoring that for the moment, he takes a deep breath and tries to relax and take stock.

The skin on his ass hurts quite a bit from the whippings, but it has faded a lot since yesterday. His inner thighs and crack are tacky with dried come and lube. Dean presses a careful hand to his lower abdomen. Inside, it feels like when he’s worked out too hard and overstrained his muscles, a pulling soreness.

“Sore here,” he mutters.

“I am not at all surprised. Here, let’s have a look at you.” Novak is so matter-of-fact about it that Dean only grumbles a little as the blankets are pushed away and he is rolled onto his back.

Novak is naked too, and he’s smiling at Dean in the sunlight, kneeling above him, and Dean just blinks at him, still not really awake. He hadn’t had much chance to look last night during the...the sex--a full body shiver runs all over him--but Novak is gorgeous. He has pale skin and just a dusting of dark curly chest hair. Lean, corded muscle everywhere, wide shoulders and a trim, narrow waist. Dean’s eyes dip involuntarily lower. He’s hard, but not rampant, and his cock is huge, thick, and dark where it hangs between his thighs. Dean licks his lips nervously and looks away.

“Knees up. Hold them for me.” Novak presses his knees up towards his chest, and Dean stares at the ceiling, fighting back his blush. The anger that has energized him for months, years, is slippery this morning. He can’t quite grab hold of it; it’s present, but just out of reach. He wraps a hand around each knee, holding himself open as Novak moves to sit below him on the bed. The position actually seems to ease the ache in his pelvis, so he breathes deep.

“You’re quiet this morning,” Novak murmurs, and Dean jerks a little to feel palms on his ass cheeks, spreading them a little. “Not sure if you’re still processing or just not a morning person. I suppose time will tell. Ah, there. Such a pretty, puffy, sore little bud. Lovely, Dean.” Something dark curls through his voice, and Dean must be sick or something, because he feels a hot flush of satisfaction, or pride, or something like it, because Novak is obviously pleased with him.

A moment later he’s pressing his head back into the pillow, clenching his teeth, and hissing “owowowow,” though, because even though the probing fingers are very gentle, they feel like sandpaper and ignite a burn in his hole like when he’s had far too many hot peppers and been sitting on the toilet for hours. Novak presses a palm on his belly, though, and the finger pushes in and moves like it’s searching for something, it hurts, and there’s a strange moment where Dean has the strongest urge to pee, and then the pain all eases. He blinks, startled, and Novak laughs, pulls out his finger, and tugs Dean’s legs back down to the bed.

Dean really likes Novak’s laugh, he’s appalled to realize.

“Old trick I learned from another Dominant years ago. That should make you more comfortable for a while, sweetheart. I’ll let you heal up this morning, but we still need to take care of this. Do you want to give me pleasure, Dean?” His voice is a coaxing, low purr. Dean looks at him, his little smile, his quiet face.

He remembers last night. The overwhelming pain, the fear that transcended into something completely different. The searing burn of that cock coring into him, the helplessness he felt, the way that feeling sank into his bones and gave him the strangest peace. The pulses of near-orgasmic pleasure he felt when Novak shot his come inside him, and praised him, all of it wrapped in the agonizing, relentless torture of his hole.

“Yes, sir?” he tries, then clears his throat. He’s not some pussy simpering thing. “Yessir.”

Novak’s face lights up when he smiles.

“Oh, good boy. Roll on your side, good, just like that.” Dean hears the pop of a cap of lube and a little frisson of fear rolls down his spine, but he’s good, he’s being so good. Sir will take care of him, he’s sure.

As Novak slicks up his cock and starts to fuck the space between Dean’s thighs, Dean actually relaxes, for the first time in probably years. He leans back into the hard body behind him, letting the hand massaging his tit buzz up his nerves with good feelings. This might not be so bad, he thinks. He still hates being a Sub, but he can’t deny that something inside him gets all warm and satisfied and full when Novak is pleased with him. He can let Novak slap him around for a few months to learn how to keep shit under control, not go off the rails.

“Focus, Dean,” Novak says into his ear, and pinches his nipple hard.

“Ow! Sorry, ow.” He clamps his thighs tighter together, looking down his body, fascinated by how Novak’s heavy thrusts are pushing his own half-hard cock and balls forward on every thrust. Novak isn’t nearly as intense as last night, and comes quickly. He murmurs praise against Dean’s shoulder, kissing him, nipping under his ear, and Dean melts again, not even bothering to be disgusted with himself. This is a great way to start the day. He’s sure things can only get better from here.

...

Six hours later, his arms are braced against the door frame of the training room, his knees are locked, and only Novak’s grip on the collar he’s wearing is keeping him from bolting down the hallway. The big black frame against the far wall fills his vision; he can barely track Novak moving and saying something in the periphery. Flat, blank panic pounds his heartbeat in his ears, his throat, and he strains away again, nothing but instinct driving him.

Big arms come around him from behind, and he reacts instantly, slamming his head backwards into the face of whoever has him. They stagger backwards together, but the arms don’t let go, and he goes for another hit and then Novak is on him from the front, slapping wrist cuffs on him, wide leather bands, and clips a wide chain leash to his collar. Now his hands are bound and he’s leashed, and a tiny bit of sanity returns. He shudders.

“Easy, baby, breathe now,” Novak is murmuring, pressed up against his front. Dean’s still restrained, someone has his arms pinned to his sides, and he doesn’t have much leverage, but he can’t see the door anymore and he shakes his head, trying to clear it. Novak is right there, in his face. He looks unconcerned, what the fuck.

“Benny, keep holding him. Just another moment, let me get him clipped up--” Smooth leather tightens around one thigh, then the other, and chains jingle as Novak fastens them between the thigh cuffs and his wrist bindings. He’s not immobilized, but he’s definitely impaired; when he tries to jerk his hands up, they can only go a few inches above his waist before the chain catches them.

“Shit, what his this, sir? I’ll be good, I’m sorry, I don’t know what that was?” Dean breathes out, confused, already cringing a little in anticipation of the switch, and Novak nods at him.

“That was a full fledged panic attack, sweetheart. All right, Benny. Let go, step back. Have someone take a look at your nose.”

Dean glances back. Benny, the big man who’d served dinner last night, is bleeding from his nose, a lot; Dean winces. “I’m sorry, man, I’m so sorry--”

Benny waves a big hand, the other pinching his nose. “No worries, brother, not your fault. I should have been more careful. You be good, now.”

“Dean.” Dean whips around to look at Novak, who’s indicating the training room door. “Let’s go.”

“No no no no” Dean flings himself backwards until he hits the end of the leash, and shakes his head like a dog, pulling all his weight against it. Novak has a solid grip, though, and though he rocks a little as he takes Dean's weight, he doesn’t budge..

“I’m not going to force you. We’re going to go in together. Slowly. Take a breath, slowly, all the way in, good. Now let it out. Well done. Can you tell me what’s setting you off?” Novak takes his moment of indecision to tug him forward a step towards him, and Dean goes reluctantly. He reaches up to scratch his nose, the chains check his hands, and in that moment of imbalance Novak urges him on another step.

“There’s something in there,” is all Dean can say. “Big and black. It’s, um. Dangerous?” Fuck, it sounds so stupid. But Novak isn’t laughing.

“That’s a punishment rack. It can be set up a number of different ways, for all kinds of scenes and scenarios. Many masochistic Submissives adore it, but it is very menacing. Have you had a bad experience with one before? Take another deep breath. Good.” Novak urges him forward another small step, they’re in the doorway again, but Dean can’t see around the Dominant into the training room.

“I don’t think so. Never seen one that I can remember.” Stupid, stupid, this is so stupid, he’s shouting at himself in his head, but Novak’s hands on him are warm and steady, his eyes are very blue, and serious.

“You are having an atypical adrenal response, and your body is interpreting it as panic. Fight or flight, remember? The day has been quite calm so far, perhaps this is a hormone dump of some kind. Either way, Dean, there is nothing to fear inside that room. We will work on some standard Submissive body positions for an hour, nothing that will hurt, and then begin walking you through exposure to kinks and fetishes. The punishment rack will not be involved.”

If they sold Novak’s voice in bottles, Dean can’t help but think, it’d be a best seller. Calm, deep, and even, it soothes the pounding rattle of his heartbeat down into something a little less frantic. He shifts a little, following the gentle pressure of the hands on his hips, feeling the pull of the chains against his thighs, rolls his shoulders, and takes stock. He’s okay. Just a blip on his brain radar, somehow.

“Good. Excellent. Here, let me fix that, the chain is looped.” Novak tugs on the chain fastening his left wrist to his left thigh, Dean takes a step to compensate. “Keep looking at me, Dean. I want you to glance at the rack out of the corner of your eye, and tell me how you feel.”

Fuck, they’re inside the room, and Dean hadn’t even noticed. He does dart a quick look at the looming black structure, and...nothing. No fear.

“I’m. It’s fine. What the hell.”

“I know you’ve been skeptical about all the talk about brain chemicals and imbalances,” Novak says, now smoothing hands up and down his flanks. It feels really nice. “But that’s some real-life proof, if you want it. Imagine that that happened while you were at work, or driving your car. ”

Dean can’t fight back the full-body flinch. What if Sam was in the car. He blows a calming breath out through his mouth, eyes finding Novak’s face again. “Yeah, okay. That would seriously suck. Sir.” Ready to get it over with, he starts looking around for the switch.

“What are you doing, Dean?”

“I broke Benny’s nose, sir. That’s gotta be good for what, five?”

“Dean.”

His eyes snap back to Novak’s face at that hard tone, and yep, the Dom is frowning at him.

“I believe that there is only one person here who determines punishment and reward, and that person is me. You will never be corrected for a panic attack, or for any other inadvertent reaction that you cannot control.” The frown smooths out, and now those blue blue eyes are smiling a little. “In fact, if something we work on here in training takes you by surprise and your body jumps right to orgasm, you won’t be punished for that, either. Though I trust you will try to restrain yourself if you can.”

Dean has to scoff a little at that, but the relief is heady, and the last traces of fear drain out of him, leaving him tired.

“You’re really not what I expected, sir,” he says, unguarded, before he can catch himself. He winces and eyes Novak carefully, but the man doesn’t seem offended.

“I get that a lot,” he answers peacefully. “But we can talk about all that later. We’re already behind in our position training, so I’ll show you the space and we can get started. Come along, now.” He steps away from Dean and turns him a little, beckons him further into the room.

Dean’s eyes go wide. This place is crazy.

“The main space is for general use and training. Open floor with padding, to keep knees safe,” Novak narrates, as he leads Dean forward. The room is huge, with high ceilings, and five or six doorways lead off to other rooms. The main floor area is empty, but in addition to the large rack, there is other furniture and gear scattered around, some against the walls, some free-standing. Dean recognizes some--a spanking bench, a medical table, a regular dining room table and chairs, a few couches, a wide, padded low bench like an extra super-sized ottoman--but some he doesn’t have any clue about. The light is bright but not harsh.

“There are rooms off the sides for special use, as well. Since this is a training home, we need to be able to accommodate a wide variety of scenarios and preferences.” Novak leads him to one, and with a gesture invites him to look in.

It’s a room with pet bowls, leashes on the wall, dog and cat toys, and a wire crate, as well as soft furniture and a small couch-bed. Dean jerks back and collides with Novak, who is standing behind him, and who suddenly has arms around him, holding him firmly, one hand splayed across his lower belly, one on his chest. Warm and possessive.

“Once we have gone through the basic training, we’ll be walking through all of the main kinks and fetishes to test your affinities,” Novak says behind him, kind but firm. “If your scores had been accurate from the beginning, you would have been exposed to these things organically, over time, as you matured. High level Submissives like yourself almost always find fulfillment--and partners--in the more extreme areas of sexuality. Shhh, Dean. Relax. It’s natural and healthy and good.”

Dean tries to get his breathing under control again. He nods, stiffly, staring at the pet bowls.

“Can we see the other rooms, please, sir?” He gets out.

“Of course.”

The next room resembles a child’s playroom. It has a sturdy adult baby changing table, plush toys, blocks and games. Bottles and children’s books line the shelves of the brightly painted bookshelves, and a mobile turns above an adult-sized crib. Adult diapers and a plastic potty, a couch-bed, and a drain in the floor. Dean pushes right on past that one, without a word to Novak, who’s at least letting him lead.

The third room is better, at least. It just has clothes. Very traditional male and female clothing, it looks like...everything from underwear to work clothes to formal dresses and tuxedos, and large mirrors and a makeup table.

Dean cocks his head, considering.

“You’d look marvelous in a gown,” Novak murmurs into his ear, and Dean can feel his face heat, and moves on.

“This is the recovery room,” Novak says, gesturing at the room filled with soft pillows, reclining chairs, a full bathroom off to the side with a large soaking tub, and soft warm lighting. “After every session, we will spend time here. We can talk freely, and rest. This kind of training can be mentally and physically exhausting, and it’s important to take time to settle and return to baseline after exertion.”

“I’m feeling pretty exhausted now,” Dean, emboldened by Novak’s ease with him so far today, looks up at him through his eyelashes. Even Dad hadn’t been able to resist that look too much. “We should skip right to this part today, right?”

“Nice try,” is the dry answer, though Dean’s pretty sure Novak is trying not to smile. Dean sighs, regretful. “We’ll tour the other rooms some other day. Let’s get started. We’ll be going through the five basic positions today. Over here, if you please.” Novak guides him back to the big padded ottoman thing. Dean just stands in front of it, confused.

“Body positions are very important in communication between Dominant and Submissive. A Dominant will place you into certain positions to indicate what their plans and expectations are for you at that moment. A Submissive can move into positions that will communicate wants and needs to their Dominant without using words.” Even as he speaks, Novak is unsnapping the chains from Dean’s wrists, thighs, and collar, though he leaves the cuffs in place. “Up on the bench, on your knees.”

The bench only comes to about thigh-height on Dean, so it’s easy enough to crawl up onto it, and settle into a kneeling position. He watches Novak fetch a riding crop from one of the cabinets, a long black thing with a wide leather flap, and scowls at it.

“So I guess when you said this wouldn’t hurt, that was just another load of bullshit,” he accuses, a little nasty with it, and Novak pauses to look sternly at him, mouth pressed to a thin, displeased line. He turns and retraces his steps, and fetches the switch from a small holder near the door, and the minute Dean sees Novak touch it, he freaks.

“No! Sir, I mean, sir, I’m sorry,” Dean tries to scramble off the bench but Novak is ridiculously fast and has Dean’s collar in an iron grip before he can get his feet under him.

“Face down, ass up. NOW, Dean,” and reluctantly, stiff with resistance, Dean gets his head down, still on his knees, leaving his butt elevated and exposed. He hates this. His slippery anger, out of reach for most of the day, comes surging back to him. He’d barely said anything at all! This isn’t fair and the switch is too harsh, he hates it.

“You have a bright spirit and a quick mind, and a smart mouth, and I enjoy all of them very much. But there are ways to express yourself respectfully, and you are failing to use them. Stop pushing me, Dean. The consequences will get progressively more harsh.”

“It’s not fucking fair!” he bursts out, words muffled by the way his face is pressed into the quilted fabric of the bench. “That thing hurts too much! Fuck this.” He’d twist away but the hand at his neck seems strangely heavy, he can’t really seem to resist it.

“Spanking is for fun and pleasure. Punishment should be neither. And even the biggest pain-sluts I train have little love for my switch. I have told you before that everything I do has a reason. Would you like to continue adding to your total, Dean? Or should we get this done and continue the training?”

It’s not a real question, he knows it isn’t, he hates the reasonableness of it when all he wants to do is having something to kick and scream and fight against. But it’s like fighting water, when Novak won’t get angry, won’t counterpunch, just waits patiently and then doles out the consequences. As fast as it came up, the anger simmers away, and Dean slumps a little.

“Get it done, sir.”

“Politely, Dean.” He might not be mad, but that voice is pure steel, right now. No playfulness, no humor, just grit and purpose.

“Please get it done so we can continue training, sir?” Dean shoves the words out, though they don’t want to come, and Novak rubs a gentle hand over his butt, across the fading welts from yesterday. The words seem to let out more of his anger, though, and Dean can take a deep breath, even though he’s tense in anticipation of pain.

“You will take four with the switch for disrespect. Say yes, Sir.”

“Yes, Sir,” Dean says, quietly this time.

The hand leaves his collar, and before he can even properly brace, the first hit lands. The whippy little switch sears that thin line of fire across his buttocks and he chews his lip hard, hands fisting by his shoulders. The second one is worse, lower, on more tender skin, and it rocks him forward. It hurts it hurts it hurts The third and his mouth opens and he won’t scream so he bites down hard on the padding of the bench, and the fourth leaves him panting through his nose, sweating, shivering.

Novak puts a steady hand on his lower back for a long, silent moment, until he calms.

“Up, Dean. Let’s continue.”

Dean spits out the sodden padding between his teeth and kneels up immediately, but carefully, blinking in the light. He is calm, he realizes. Calm and the riot of temper and emotion in his head seems to have smoothed itself away into peaceful quiet for the moment. He turns wide eyes to Sir, who smiles a little at him. He seems pleased, so Dean smiles too, tentatively.

“Good boy,” and those words warm Dean right down to his soul.

Sir is looking at him thoughtfully, but then sets the switch aside, and stands beside him. The bench is a nice height, it means Sir can reach him without bending or having to stretch. He puts one hand in the small of Dean’s back, and the other right in the center of his chest, so Dean is held nicely between them, supported.

“The first position is the basic kneeling Wait position. This is how many Dominants will expect you to attend them, when you’ve not been given specific commands. Tops of your feet flat on the ground, toes pointed, there. Now sit back on your heels. Body straight.”

Dean tries, and immediately jolts back up, hissing, as the new, raw welts shock pain through him at the contact.

“If you do not wish to endure a painful bottom, perhaps do not act in such a way that it will get smacked,” Sir advises with a hint of a smile in his voice, and Dean sends him a tiny reproachful look, but tries again. It hurts just as badly, but he’s prepared this time and doesn’t jump, though he does clench his hands a little against the fiery burn.

“Good, better. Now here.” The hand on the small of his back slides lower, over his ass, down to the lower curve, pushing forward, and Dean chokes against the agony. “This won’t last long, sweetheart. We’ll move to a new position soon, but you must get this one right, first. Tuck your pelvis under, so your body is a straight line from hip to shoulders. Good. Lift up like there is a string attached to the top of your head, running to the ceiling, drawing you tall. Lovely, yes.” Embarrassingly, Sir reaches between his legs and scoops his cock and balls free, settling them on top of his kneeling thighs, vulnerable and exposed and displayed, but he’s too distracted to react. His ass feels like it’s bleeding, no skin left, but he raises his head and struggles to obey.

“Like this, sir?” His voice is thin and strained.

“Yes, just like that. Now place your hands on your thighs, palms up. Display yourself, Dean, spread your thighs open a little more. Open your palms to the ceiling, like they are waiting for something. Good. Now this is the Wait position. Hold it there. Take a deep breath for me. Another. Can you remember it?”

It’s seared into his memory forever, he’s sure.

“Yes sir.”

“Okay, kneel up.”

With a gasp, Dean jerks back up to stand on his knees. The relief is immediate, though the welts keep an angry throb going even after the weight on them is released.

“Well done.” There’s genuine congratulations, praise in Sir’s voice, and though his head is a little fuzzy and floaty right now, Dean is clear enough to realize he’s earned it by meeting a challenge Sir wasn’t entirely sure he’d get through. He grins, feeling accomplishment roll through him, loosening the remaining tension in his shoulders and hips.

“Thank you, sir,” he says sincerely. He loves challenges. He loves kicking their asses.

“Position two is Present, though some Doms will call it Rear Present. I’m feeling mercy for your poor sore bottom, so this one should be a relief to you. Spread your knees a little further than shoulder width…” Dean does so, watching Sir. Realizing for the first time that he’s dressed down, in soft-looking scrub pants and a white t-shirt. He looks comfortable and warm, his hair all messy and dark. Dean should pay attention.

“Now lean forward and put your hands on the floor. Good. Once you’re on all fours, rock back a little, spread your legs wider, good. Let your chest go down naturally and cross your wrists under your head, rest your cheek on your wrist.”

It’s a variation of how he was whipped; face down, ass up, but this feels so much more elegant. His thighs are spread wide, wide enough that he can feel the stretch in his groin, and he’s entirely exposed. In fact, even as he breathes and relaxes, Sir’s warm hand is between his legs, sliding up and down his crack gently, petting his cock and balls, rolling them in his hand, a thumb rubbing on his hole. He can feel himself start to get hard. Oh, that feels so good. He hasn’t come in...fuck, almost five days, with the training school and now this place.

“Very nice, Dean. Now see if you can pull your chest back a little. Arch your back into a deeper curve. Remember, you are presenting your sweet, soft, pretty parts to anyone behind you. Offer it up. Here.” Sir presses just above his pelvis, over his tailbone, with the heel of his hand, and Dean moans as the stretch hurts so good, as he lifts his hips and pulls his chest in tighter, keeping his face down. He feels loose and warm, relaxed like this. Like he could stay in this position for hours. It’s so peaceful with his eyes closed, his face pressed into his wrists.

“That’s a beautiful position for you.” Sir’s voice is quiet, calm. “I can see it suits you well. Imagine your spine is made of liquid, let everything hard and tense flow down out of you, into the ground. Breathe deeply. I will take care of you. You have nothing to fear, now.”

Maybe it’s the idea of his bones turning to juice, but somehow, Dean’s back suddenly loosens, drops into a deep, pornographic arch, lifting his ass higher as his whole chest is now resting on the bench. He sighs as the pull of ligaments and muscles eases, his cock twitching hard against his belly at the luscious, decadent relaxation of the feeling.

Sir is quiet, moving around him, touching him here and there, on his shoulder or hip, and it feels amazing. Then behind him, stroking the backs of his thighs, scratching through the curls of hair there. Petting his crack, his hole.

“Do you feel good, baby?”

“Mm hmm,” Dean says into his arm. He’s floating.

“Keep your hands where they are, pretty Dean. Let’s make you feel even a little better.” Dean doesn’t even jump when the finger catches at the rim of his hole, gently tugging at it, pulling, and even the zing of pain doesn’t prompt more than a deeper breath. Sir is being gentle, stretching him, massaging the rim of his ass, and it feels so different now that he’s relaxed like this. Every touch sends a little pulse of pleasure rolling up through his groin to the tip of his cock, and it’s been days and days since his last orgasm.

The lube is cold when Sir wets him with it, but he doesn’t flinch. He wonders muzzily if he’s going to be fucked here, like this. Wonders if it will hurt like before, that core-deep pain that somehow hollows him out so that peace and comfort can trickle into the space it leaves behind. But it’s not a cock that pushes into him, but something hard and smooth. The air of the room is cool, soothing on his ass, his sac, his cock, in contrast to the heat that flares in him when he instinctively clamps down around the thing being inserted into him.

“Hnnngh,” he moans into the quilting, his hips shifting a little as he gets used to the feeling. It’s still so alien. Ass play is not something he’s ever been into. He’s always shied away from anything that would lead down the road of being someone’s bitch, someone’s doormat, some subby little nothing. But those thoughts seem far away and unimportant right now, in this particular moment.

“Just a training dildo, lovely boy. If you can come just like this, you have Sir’s permission. Feel how it is stretching you? It looks exquisite opening you up when you’re positioned like this. Don’t move, hold your place, Dean.” Sir is talking steadily, and it grounds Dean, keeps him from flying apart as the dildo angles a little on the next thrust in and grinds along his prostate and Angel gland. Still sore from last night, hypersensitive, they light up like firecrackers and he moans again, louder, clenching his eyes so tightly that he can see red behind the lids.

“Be as loud as you like. Let go.”

Dean wants a hand on his dick. He needs it, is desperate for it. Like air. He shudders his hips back and forth, trying for some kind of friction without actually moving, but it’s futile. Long, warm fingers take hold of his sac, and he freezes. But they just squeeze gently and roll his balls back and forth, tugging a little, a tiny blurt of pain that gets swallowed up as the dildo drags torturously out and then pushes back in again.

“Please please please,” he hears himself chant. “Pleasepleaseplease”

“What? What do you want, sweetheart?”

“Please touch me, sir, please, gotta come, I’m dying--”

“I am touching you. Breathe deeply, Dean. Concentrate on your hole, your bottom, the pleasure you can feel here. As the dildo enters you, clench down around it.”

Slick and slippery, he can feel it pressing him open again, filthy and slow, and he tentatively does as Sir orders, clenching his hole. Immediately the pleasure throbs through his whole pelvis, deep inside, so different than when someone touches his cock. Deeper, almost like a cramp, hot and urgent and fascinating, but he can’t hold the clench and relaxes. Hears himself make a complaining little noise.

“It’s all right. Try again. It takes practice. Milk the toy with your hole. Imagine how it would feel to your Sir’s cock, that wet tight little mouth clenching and releasing. Don’t hold it for too long, sweetheart. Build a rhythm.” His sir’s voice is rougher, deeper than usual, the hand massaging his sac is a little more urgent in its touches.

Dean tightens and releases. Tightens and releases. Pleasure is spreading in a hot slow wave, out from his ass, up his spine, through his belly. His breasts feel warm and tight, somehow, and the back of his neck is heavy. He labors, hips working, chasing something he can’t quite reach, trying to match the rhythm of the dildo fucking him.

Then it slows, gentles. Sir’s hand releases his sac. No no no. That can’t be right.

“S-sir?” His voice is thick, slurred.

“That’s enough, baby. Not this time. Perhaps next time you’ll get there. You did very well.”

Dean wants to scream. Novak pauses, like he’s waiting for something, but when Dean is still and silent, he strokes a hand up the curve of his back and pulls back.

Dean breathes through the dildo sliding out of him completely with a wet little sound, and a soft cloth wiping him clean. His whole body feels like an explosion, cut off a moment before detonation. Like a single touch could ignite him. His cock is a rigid, angry thing, the tip wet, he can feel it pressing against his abdomen. But he can still hide his face, and his back still feels loose and easy, and as he takes a few deep breaths, he feels a little less likely to fall apart at the seams. And much more awake and present in his mind, if still overwhelmingly desperate for an orgasm.

Chapter Text

“Do you need a moment more?” Novak’s question is clearly genuine, but his voice has lost that intimate, raspy growl. Dean shakes his head a little, and blinks his eyes open. The light feels strange, after so long with them closed.

“No. I’m good. Sir.”

“All right. We’ll move quickly through the last three positions, and we’ll be practicing moving between them for the next few days. Here, slowly, don’t want you tipping over.”

I’ve burned whole nests of vampires and robbed three graves in a night to banish an angry ghost, I’m not going to faint from kneeling, Dean wants to grouch at him, but he lets Novak help him back up until he’s back to his starting position, kneeling up.

“Display is fairly simple,” Novak’s eyes are smiling at him a little, though Dean can’t imagine why. Dean’s pretty sure he’s looking fit to kill right now, and his cock is doubling down on the argument, standing out from his body in a demanding curve. “Walk your knees apart a bit. Good. Now interlace your fingers behind your head, and push your elbows back. Chin up, eyes down, tuck your pelvis under so your penis is elevated.” Novak reaches out with the crop and taps Dean’s chin until it lifts to his satisfaction.

That last, of all things, gets Dean’s cheeks warm with what has to be a blush. And his traitor cock gives a little jerk. He knows Novak doesn’t miss it, the way he watches, but he doesn’t comment, at least.

“Very nice, Dean. The next is Inspect, which can be done a number of different ways. We’ll do prone today. Lie down, on your back.”

Inspect what, Dean wonders suspiciously, but getting off his knees is starting to sound pretty nice, so he just flops over onto the table and rolls to his back. Only to bite off a curse when his sore butt hits the bench, jerk up, and then gingerly settle back down.

Novak makes a sound that is suspiciously similar to a choked-off laugh.

“The goal is to move between positions gracefully. Eventually. Something to work on. All right, Inspect is to make it easy for your Dominant to check to be sure you are healthy and well. For a male Submissive, they will generally inspect mouth, throat, breasts, penis, scrotum, perineum, and anus and rectum.”

“Wow, talk dirty to me, Doc,” Dean says, to the ceiling.

“This is training, not porn,” Novak says with an edge of severity, but when Dean glances up at him out of the corner of his eye, the corners of his mouth are a little lifted. “Put your hands behind your head again, lock your fingers, and spread your legs. During Inspect, the only time you are to move is when your Dominant gives you a direct command, is that clear?”

“Yes sir,” Dean says, as he shifts into position. Novak taps the inside of one thigh with the crop again, and Dean opens them a bit wider. This isn’t nearly as cool as the Present position. And he just knows he’s gonna be poked and prodded some more, which is not really his favorite thing.

“Mouth. Open wide.” Dean opens, managing not to roll his eyes as Novak bends close and pulls his lip up, presses down on his lower teeth, looks closely at his mouth and tongue and throat. He smells nice. Spicy and warm. “Good,” Novak says. He moves to Dean’s chest, and cups a warm hand over Dean’s pec, palming the nipple. “A very pretty handful. Still too hard, though,” as the heel of his palm kneads in. Dean grunts at the sore feeling, grimacing.

“Why the face, Dean?”

“I don’t get it. I’m never gonna pop out a baby. But no matter how hard I hit the gym, how many hours I put in at the garage, I’ve still got these fu--fricking moobs.” He strains his eyes down to glare at them. Small, sure, just a small soft rise of flesh around his nipples, but definitely an interruption in what is otherwise a very purely masculine torso.

“Their purpose is twofold,” and Novak is talking in what Dean is starting to think of as his ‘medical lecture’ voice. “One is to create space for your Angel glands, of course, and to elevate them to ensure stimulation. In a Switch, the breast glands are much smaller, so the need for subcutaneous fat is greatly reduced. The other is to allow for a much deeper erectile tissue structure underlying your nipples.” Novak rolls his palm gently over Dean’s nipple, over and over, and as it hardens, it sends pulses of pure pleasure down to his groin.

His cock, half-flagging, fills hard again.

“Your body is a miracle, Dean. The demands and needs of a highly Dominant partner can be extreme, and sometimes difficult to bear. You were built to extract pleasure and fulfillment from even those extremes. It’s incredible.”

Dean glances at him, searching for humor or sarcasm, but there’s genuine wonder on Novak’s face as he stares down at Dean’s body, still gently kneading at his breast, then shifting to give the same attention to the other one.

“I wish they taught some of this stuff in school. The Sex and Orientation Ed me and Sammy got was pretty bullshit and none of this stuff was in there,” Dean says quietly, without thinking about it, and Novak sighs.

“A number of doctors, therapists, activists, you know the type,” he finishes with Dean’s chest and moves down beside his hips, and Dean can’t help but tense a little as he takes his cock in hand, as hard and aching as it is. Novak ignores it, and keeps talking. “We have been lobbying the state for a while to change the curriculum. It’s been slow going, but I think there’s been some progress. As well as changes in the testing protocols.” He presses careful fingers down Dean’s shaft, and Dean hisses and squirms.

“Easy. Deep breaths.” Novak releases his cock, moves to his balls, pulling them up so he can run a finger around the root, check the seam.

Dean feels like a toy. Or, he thinks, like a gun his dad is checking and cleaning. But it’s not a bad thing, or a bad way to feel. Instead, he feels...valued, somehow. He flushes, staring up at the ceiling, as Novak gently squeezes each testicle, then lets them fall.

“Knees to your chest, Dean. This time, you will reach down and spread yourself wide for inspection,” Novak’s voice is gentle but firm.

It’s humiliating. It’s going to hurt, with his whipping welts. Dean bites his lip and slowly gets his knees up, feet coming off the bench as he curls, and reluctantly moves his hands down to his own hips. He can’t quite bring himself to reach between his sore cheeks and pry himself wide open, though. He can’t.

“Was I unclear?” His eyes shoot to Novak’s face, and there is a line between his brows, his mouth is tight. He is not amused.

“N-no, sir.” The little hitch in his voice is from his tight throat. Reaching back with his fingers brings his hands into contact with his sore, welted ass, and he gasps, but forces himself to keep going. Palming his own cheeks, he pulls his hands apart gently.

The cool air is shocking on his hole, but he can barely feel it. All his focus is on not letting go and just curling up from the pain.

“When I give a command, I expect it to be obeyed immediately and without question.” Novak snaps out, his voice still unyielding. He leans in close to Dean, lifting his balls aside, pressing on the tight skin of his perineum, and Dean’s breath hitches again. At least his cock isn’t hard anymore, he thinks half-hysterically.

“Yessir,” he gets out.

“If you relax, this will be less painful,” Novak says. Dean feels pressure on his hole again, and he’s still kind of loose and slick with lube from before, but two fingers pulling him open is still sharp, sudden pain.

“Ow! Ahh, ow,” he bites off, breathing hard, trying to relax his hole.

“I could use my speculum if you would prefer,” Novak says, voice level and unsympathetic. Dean winces.

“No, thank you sir.”

“I thought not. Your anus is slightly irritated from use, but much improved from this morning, and the rectum is normal and healthy.” The probing fingers leave him then and Dean gasps in relief. “You may release. Return to original position.”

Dean gets his shaking hands back under his head.

“And that is Inspect. The final position we’ll practice today is Rest. This is meant to be a neutral position that puts no strain on the Submissive, so that after working hard, a Dominant may leave them this way without concern that they will become distressed. Hands and knees.”

Dean clumsily gets back up.

“Now curl yourself up, not too tightly. Hands under your chest, knees under your body. Like a child sleeping.Turn your face to the side so your cheek is on the ground, good. Take a deep breath. Are you comfortable?”

It’s an odd pose to be in, but it actually is super comfortable, Dean realizes. “Yes, sir,” he answers, after taking stock. Even his butt doesn’t hurt, since he’s not putting any strain on the sore skin.

“Good. Rest there, do not move. I will not leave the room.”

Dean nods, eyes tracking him as he moves around the room. The dildo is washed and put away, the switch and crop replaced. It’s kinda soothing, like this, just existing quietly and watching Novak work. By the time Novak comes back to him, Dean’s breathing deeply and calm.

“I think that’s enough for you to take in today,” Novak says to him, and Dean has to nod his agreement. Novak smiles a little. “One last thing, then, before we go get cleaned up for dinner. Am I right in thinking you’ll want to call home during your free time tonight?” Dean nods again, much harder. “And you’ll want privacy for that call?” An even stronger nod.

“Yes, absolutely, sir. Yes.” He hasn’t had a moment out of Novak’s company since he got to this place. He suddenly needs alone time like he needs air.

“Your father did not have a personalized chastity cage to send with you,” Novak frowns a little, like that displeases him. “So we’ll have to use one of the standard cages I have here. Display, Dean.”

He has to search his memory frantically for a long moment, and then lurches up to his knees, and gets his hands behind his head with his elbows back.

“I don’t need a chastity cage, sir,” he tells Novak’s back, as the man opens one of the storage cabinets on the nearest wall and seems to be looking through the contents. “I won’t, you know. I swear.”

“Mm-hmm. While I believe you of course, I find it’s best to take temptation fully out of reach.” Novak has three small contraptions in his hands when he comes back to Dean, two metal and one plastic. They all look pretty much the same to Dean. Horrible. The padlocks in them have small keys inserted. Dean stares at them, wide-eyed.

“Don’t worry, they’ve never been used. We keep them here just in case,” Novak assures him, as he starts opening all the little fastenings on the clear plastic one.

“I wasn’t worried about it being dirty,” Dean chokes out.

“Really? Well then. Keep your hands back, please, and do not move. I believe this should fit.” Without any ceremony, he works the clear plastic ring around the base of Dean’s cock and balls, pushing them together. As he pushes the ends closed, the ring catches and yanks on a few stray pubic hairs, and Dean yelps, jerking back.

“Oh dear. Well, I’ll remind you of this during the inevitable tantrum when we have the waxing groomer out later this week,” Novak says, with actual sympathy this time, and wait, what? But he’s working the little plastic cage on over Dean’s actual cock now, and it’s not comfortable at all.

“Too tight,” Dean says, nose prickling with the uncomfortable constriction in his most sensitive place.

“I agree, definitely. Hold on, I’ll get it off.” Dean sighs with relief as the pressure is removed.

“The next size up is metal, so it will be colder.” It’s fairly simple, Dean can see. A smooth metal circle, that Novak replaces the plastic ring with. And a curved tube made up of silver metal bars, with a perforated solid tip. This time, the whole thing slips on smoothly. But it feels strange, heavy, hanging between his thighs.

Novak clips the cage to the ring, and locks it in place, and Dean has to take a deep, calming breath. He can’t get at his own cock. Not at all.

“I will always have the key with me, Dean,” Novak’s voice penetrates his rising anxiety, and interrupts it, with its calm steadiness. “And as there are multiple copies, so no matter what, you can speak to Meg or Benny, and they can release you in the event of an emergency. You will never be out of shouting distance from someone with the key. Yes?”

“Yes, sir,” Dean says, shakily. That does make him feel a little better.

“All right. I think it’s important to get you fed and hydrated, now, more than anything. And then I’ll show you the phone room, and you can have your free time.”

“A landline?” Dean’s nose wrinkles in unconscious disdain. His own cell phone had disappeared with his bag.

“A landline,” Novak confirms, with a little grin. “Come on, now. We’ll clean up in the recovery room, and then feed you. Since the steak was so well-received last night, I believe tonight is shishkebab.” As if on cue, Dean’s stomach rumbles, and if he follows a little too closely as Novak leads him away to the side room, well. No one has to know.

Chapter Text

Dean had fought the kneeling and hand-feeding again during dinner, and had only submitted to having his thigh and wrist cuffs attached to each other and his collar before his free time under threat of a whipping, and even then, with poor grace. Castiel runs a tired hand over his face as he steps into his office and closes the door. Sitting back in his big chair, he stares at his little desk lamp for a long moment. Then picks up the phone, and dials.

“Cassie!” His brother’s voice is not always a pleasure to hear, but right now, it makes him smile.

“Gabriel,” he answers solemnly. “I hope all is well at the school?”

“Oh, the school is good. It’s always good. Especially it’s good now that you’ve taken the delinquent home with you and nobody’s getting punched in the face. There’s nothing new or interesting here on a Sunday night and you know it, so spill, little bro. Did he break all your windows and climb the walls yet? Did he take your cook hostage?”

Castiel huffs a laugh, and kicks his feet up on the desk.

“No, the house is still standing, and I think Dean likes the food here too much to threaten anyone in the kitchen. Gabe, he is in very bad shape, though. And he’s a Winchester. How did it get this bad without one of us noticing?”

The teasing humor drops out of Gabriel’s voice for a moment.

“I’m honestly not sure. John and Dean would’ve noticed anything but the highest-level surveillance, so we’ve been totally hands-off, as you know. I did a little digging, and it looks like Dean hasn’t been to a doctor in about four years, now. Once he got his Orientation card he’d have been able to skip out on any of the school testing without any problems, so no red flags ever showed up anywhere we would have seen them.” Gabe sighs. “Michael’s already working on adjusting for Sam, so we can be sure this doesn’t happen again. He’s gonna be okay, though, right?”

“He’s not the worst I’ve seen,” Castiel admits. “But he might be the trickiest. His Subutanol levels haven’t budged a fraction since he got here. His pain response is atypical. All of his responses are atypical. He absolutely refuses to submit. He obeys, more or less, and sometimes he even enjoys it, but there’s no real surrender there. At least his Rewarardin and Adrenaline and Serotonin scores are starting to ease back towards normal. But he’s fighting me hard.”

“It’s a good thing you love challenges. Look, I know you’re used to working miracles--”

“Hah!” Castiel interjects,

“But it’s only been two days. Maybe he needs a little more time to accept his new normal.”

“He hates being a Submissive,” Castiel says, gloomy.

“Well, yeah,” Gabriel’s voice sounds surprised that it even needs to be said. “You think Submissives are these exalted, powerful, righteous beings, but that ain’t what a lot of them experience out here in the real world, and that’s the world your Dean-o has been living in. Plus his dad and his mom and their whole family for generations have been Switches, so he’s got no context at all.”

“I know, but this is different. It’s turned inward, somehow, more than just the general reaction to societal biases I’ve seen before. He struggles to kneel, for one thing, which is just...basic. And he’s incredibly resistant to anal play, for another. He’s almost completely inexperienced, there.”

Gabriel gives a long, low whistle. “The first fuck must have been something, then.”

“It was quite rough,” Castiel admits. He shifts in his chair, cock hardening even at the memory.

“Don’t lie, you loved it,” Gabriel teases. “And it probably did him a world of good, though it will take him a while to admit it. How does he respond to punishment?”

“Very well,” Castiel says, brightening a little. “He hates my switches--”

“EVERYONE hates your switches, Cassie--”

“--but the aftermath of punishment is always a calm, centered moment for him. He hasn’t cried, and hasn’t apologized, so we’re still far away from any kind of remorse and comfort, but even one or two stripes is a guaranteed attitude-adjuster for him.”

“See? That’s fantastic. He’s a strong kid, just ask Derek’s nose. Don’t be afraid to take a firmer hand with him, Castiel. Kid like that, he respects strength, and he’ll never submit without respect.”

“You know I have to be careful with that kind of thing, Gabe,” Castiel protests. There’s a moment of silence.

“Yeah, I know. Speaking of which, did I tell you about the new girl, Breanna, just applied to Dominant Delight to be a Submissive assistant for the training program?”

“No,” Castiel starts, wary, but Gabriel bowls him over with a rush of words.

“Oh my grace, Cassie, she’s something else. One of the highest-level Subs we’ve ever seen, and she’s a hardcore masochist. I did her interview and she was begging for more after I went as hard as I could; she was barely even registering it. Seriously, little brother, she’s applying for the job because she can’t find a Dom to hurt her like she wants--”

“Gabriel.” Castiel’s rubbing his temples again.

“You need someone, Castiel! I know you say you get everything you need from training, but you can’t be harsh with some of the Subs you get, and I know how hard it is for you even when you can be.”

Castiel blows out a long breath. “I know. I know. Not right now, okay? Dean’s taking all my energy and focus, and believe me, he’s going to be more than satisfying enough for a while, considering how bratty he is, and his pain response. He isn’t a masochist, though, so don’t get the wrong idea. But I promise, Gabe. After Dean, I’ll start looking. Okay?”

Gabe groans theatrically. “Fine. I’m holding you to that, you know. And we’re hiring Breanna, so I’ll know just how to reach her.”

“Fine.”

“Fine. Love you, Cassie.”

“Love you too, Gabriel. Talk to you tomorrow.”

After hanging up the phone, Castiel leans back again, quiet in his mind. Letting himself be free, for the moment, of the problem of what to do with Dean.

***

The collar and cuffs don’t bother Dean that much, but the chains linking them are a screaming pain in his ass. He can’t move his arms or legs freely, and no matter what Doctor Fucking Novak says about safety, Dean’s free time should be free, goddammit. He shuffles into the phone room, which is so weird and lame, and slumps onto the couch.

The room is kind of nice. Cozy. Not that any room in this ridiculous mansion isn’t nice, as far as Dean’s been able to tell.

Before he can get worked into a real funk, he grabs the handset off the base and dials his home number. It’s Sunday, Dad and Sam should both be home.

“Winchester residence.” That’s his dad’s deep, whiskey-rough bass, and Dean almost curls himself around the phone at the sound.

“Hey Dad,” he gets out. “It’s me.”

“Dean? Boy, it is good to hear your voice.” His dad sounds warm, like home. If Dean was the kind of guy who cried, he’d be in tears by now, but he isn’t, so he swallows hard, and tries to sit up straight again.

“Yeah, uh, Mr. Novak said I could call whenever, you know? Say hi, see how everyone’s doing.”

“We’re fine. Well, Sam’s still pretty mad, but not at any of us, so I only have to listen to the lectures,” John chuckles a little. “How are you doing? You settling in okay?”

“I, uh.” He swallows again. “I guess. It’s not. Well, you know.” He and his dad don’t really talk about feelings much. He’s not sure how.

“I know it’s gotta be a real adjustment, but Dean, I know you can do this. I ‘bout turned myself inside out the first few weeks of boot camp back when I enlisted, you know that? But it got easier, and this will too.”

“Yes, sir.” Dean almost chokes on the words. He’s not really sure it will.

“Attaboy.” Feelings discussed, John moves along. “Novak’s pretty famous, y’know. He and his brothers came out of nowhere a few years back, started a bunch of real good training schools all over the country. Their program is getting imitated all over the place. Guess it’s making a big difference to a lot of folks. Then they handle the rare cases, like you, son, free of charge. That’s pretty fortunate, I’d say.”

He hadn’t even thought of how his dad, a gun safety instructor, was managing to pay for high-class private training.

“Yeah, pretty lucky,” he sighs.

“I talked to your Uncle Bobby today,” John offers, after a moment of tight silence. “He’s happy for you, son. He told me he was getting pretty concerned, there, lately.”

“I was never even late to a shift! I always did great work!” Dean flares up, shocked and hurt, and his dad interrupts.

“No, of course, he said you were his right-hand man. They really miss you down there, but he could see you were getting pretty sick, Dean. He’s happy you’re getting some help, is all. He cares about you, you know that.”

“Tell him I say hi,” Dean answers, a little abashed.

“I’ll do that. And don’t tell him I told you, but my old Impala you’ve been working on with him? He found a transmission for it. He’s already put it in for you, so when you get home, if your Dominant approves, it’ll be ready for the road.”

Dean goes cold all over.

“What do you mean, if my Dominant approves?”

John clears his throat.

“There are a few good matchmaking services in Austin, Dean. It’s pretty clear you have...special requirements, to make sure you’re healthy and happy. And I think you’re old enough now to realize that sometimes life just goes in directions we don’t plan for. We’ll talk it over when you get home, and of course, get Novak’s input, too, but I expect to get you started looking for a long-term contract pretty quickly once you’re done with training.”

“Dad!”

“Dean, no. I listened to all your arguments, and look where we ended up.”

“But there’s no way some civilian Dom is going to let me go on hunts! Oh my god, what if they won’t even let me drive?”

“Then that will be their decision made for the best interests of your relationship.” John’s voice brooks no argument. Dean knows that tone. But he can’t stop himself.

“No way, Dad. No fucking way!”

“Dean Michael--”

“I won’t do it, you hear me? I’ll leave, I’ll hit the road, sometime when you’re not even looking. You’re not selling me like a cow to some whip-happy sadist, I won’t let you--”

“DEAN.”

A lifetime of respect snaps his jaw closed. And the anger in his father’s voice.

“You listen to me, boy. I know you, hell, I taught you everything you do know. Novak showed me your numbers. Did you know you were two weeks out, if that, from a full meltdown? Something you’d have to be hospitalized for? Can you even imagine what that would do to me, to Sam, to our family? We need you, Dean, alive and well and here with us. So you nut up, accept reality, and you make the most of this opportunity, you hear me? And don’t you even think about leaving Novak’s without his permission, before you’re cleared. You’ve probably got three escape routes planned out already, but you will not use them, am I clear?”

“Yes, sir,” Dean whispers.

“Louder, Dean. Make me believe it.”

“Yessir.”

“All right. That’s better. Now let me call your brother, he wanted to talk--”

Dean gently places the phone back on the base, disconnecting the call.

Chapter Text

Dean is actually waiting in their bedroom when Castiel opens the door at 10:30, and Castiel admits, it’s one of the larger shocks he’s gotten lately. The boy is sitting quietly on the side of the bed, still cuffed and chained, still in chastity, and Castiel has to pause to admire the gorgeous picture he makes.

“I’m very happy that you’re punctual for bedtime, Dean,” he comments, unbuttoning his shirt, toeing off his shoes. “Did you have a nice call with your family?”

There’s no response, so after he sheds his belt and shirt, he walks to the bedside, a little concerned.

Dean is staring blankly down at his hands. He doesn’t flinch or move when Castiel puts a hand on the back of his neck.

“Dean?”

Green eyes raise to his face at that, but they’re dull.

“What happened, sweetheart?”

Dean tips a shoulder, listless.

“Dean. Answer me with words when I speak to you, if you please.”

“Nothing, sir.” And where is the snap, the bite, the edge of defiance he’s already become used to?

“Is your father healthy? Sam?”

“They’re fine.”

Castiel shakes him a little, but there’s no resistance; Dean is like a doll. Limp.

Rocking back on his heels, Castiel considers the boy; something is very, very wrong. Then gently urges him back until he’s fully on the bed.

“Let’s get you more comfortable, pretty. Did you know, I had to stop in the doorway for a minute when I saw you, because you looked so gorgeous sitting there?” As he talks, his hands are busy. Unclipping the chains first so that Dean can relax back on the bed in comfort. Then unbuckling the thigh cuffs, the wrist cuffs, and the collar. The skin is smooth and unchafed underneath, good.

“Brown leather and silver suit you. Black is traditional, but I thought it might clash with your freckles.” He cuts a quick glance at Dean, who doesn’t even blink at that absurdity. Setting the cuffs and collar aside, he unclips the little key from his pocket chain, and unlocks the chastity cage. Gently working it off, he confirms that there’s nothing wrong there, either.

So the problem isn’t physical.

“Dean, I need you to look at me, and be honest with me.” Sluggishly, green eyes meet his own again. “Is this an anticipation of the sex we will have tonight?”

“No sir.” Dean shakes his head a little, then just stares past him, at the wall. Castiel can detect no lie in his answer, which is something, but leaves him as baffled as before.

With a final pat to Dean’s hip, he stands again and finishes stripping. The room is as he likes it, cool but not cold, water and fruit fresh on the night stand, but nothing feels right. With a sigh, he moves to the bathroom, leaving the door open so he can see Dean easily, and brushes his teeth, readies himself for bed.

Dean’s eyes are closed, but he’s not sleeping, and he moves easily enough when Castiel touches him, urges him to stand. The only reaction he gets is a little shift of surprise when Castiel turns down the covers and urges him to get in.

“Something is obviously paining you deeply,” Castiel answers the unspoken question quietly, following Dean into the bed, making sure that they are touching as much as possible, skin to skin. He presses a soft kiss into Dean’s shoulder. “I would no more take my use of you now than I would if you were suffering with a cold, or some other illness. Rest now. Things will look better in the morning, and perhaps you will be able to tell me then.”

Dean doesn’t answer with anything but a small sigh, more like a release of breath, but he doesn’t pull away.

***

It’s dark, with the quiet stillness of very early in the morning, when Castiel snaps awake with the bone-deep knowledge that something is not right. He reaches for Dean, and finds only cool sheets.

Ah.

It’s possible the boy could be getting a snack in the kitchen or wandering downstairs; it hasn’t been forbidden. But Castiel already knows that he’s gone. Energized, he jumps out of bed, digs comfortable, practical clothing out of his closet, shoves his feet into boots, and slaps the all-house intercom on his way through the bedroom door.

“Dean’s gone. Everyone meet in the front room in ten minutes, please, dressed for outdoors.” He can hear the echo of his own voice in distant parts of the house, and sees a light snap on downstairs, reflected up to him in an entryway window.

Ten minutes later, he looks around at the circle of faces, and nods. Everyone looks tired and pale. It’s almost 3 am. Benny especially appears to be quite unhappy.

“Dean left the house at an unknown time, between eleven and, let’s say, two am, judging by the sheets. I’ve confirmed his pack and the clothes he was wearing on arrival are also missing. Cole, can you confirm the contents of the pack?”

“Um.” Cole scrubs a hand over his eyes. “Jeans, t-shirts, flannel overshirts, boxers, socks. A wallet with ID and seven dollars cash. A ziplock bag of kosher salt, a little squeeze bottle of what looks like olive oil, a book, a small photo album. Two antique stiletto knives stitched in right by the framing. Oh, a cell phone, but it’s definitely dead by now.”

“Thank you. So, he is clothed, and armed. For those who do not know, Dean has been trained by his in hand-to-hand combat and fighting techniques, as well as tracking and evasion, since he was a child. His father is ex-Special Forces, USMC. Benny, Cole, Meg and I will be conducting the ground search. Ash? Please, discreetly, start checking the wires for anything unusual, anyone matching Dean’s description.” Ash nods, and scurries off.

“That little asshole. How’d he get his pack?” Meg shakes her head, almost admiringly. “It was locked up in the personal effects locker, like always. He shouldn’t have even been able to find it, much less get it out.”

“Dean is a very talented young man,” Castiel informs her, smiling a little. “The rest of you, if you could, please stand by the house. If Ash finds something, contact all four of our cell phones, as we may not be together. And Angelique?” The elderly cook squints up at him. “Might I trouble you to prepare coffee and something restorative to eat for when we return with our truant?”

“Of course, Mister Castiel.” She pats his arm. “You bring him home safe now.”

“I’m more worried about us,” Benny grumbles.

“Don’t complain, you’re getting a hazard bonus,” Castiel informs him, and that brightens him up nicely.

Castiel sends Meg and Cole off in cars in either direction on the road, to start at a far point and work back in, just in case. Benny, he keeps at his side.

Standing in the dark behind his house, Castiel breathes deeply. The spring air is cool at night, a little damp, and as he reaches for his small portion of remaining Grace, he takes a moment to enjoy it.

“Can you find him?” Benny is quiet, for such a large man, but right now, Castiel can sense every soul in the house, on the road. In the neighboring house a mile away.

“If he’s not gotten too far,” Castiel answers.

“Feels a little bit like cheating. Kid worked hard for that head start,” Benny points out, and Castiel chuckles.

“We still have to catch him and bring him home. You’ll earn that bonus, never fear. Ah, there.” Dean, moving south, his soul as bright as a star. Castiel had known it must be so, but he’s still a little dazzled by it. “Yes, he’s moving quickly. He’s about four and a half miles south of here.”

“Not heading straight for home, then. Can we drive?”

“We’d better. He’s running.”

***

They run Dean to ground in a wash by an old service road he’s clearly been using to stay out of sight. Ash hasn’t been able to pick up a single blip, and if Castiel wasn’t so angry, he’d be even more impressed. Cole has returned home, but Meg’s caught up with them and she’s carrying Castiel’s bag. There’s enough light from the streetlights that he’s quite clear, as soon as they can see him fully.

Dean appears to be treating a blister on his foot, sitting with his back to the stone embankment of the gully. He’s sweating hard, pale, and as far as Castiel can tell, has no water nor any source of it.

A quick hand signal and Benny peels off to block the only avenue of escape.

“Dean,” he says firmly, and Dean startles so badly he flings his shoe at the ground, before coming up to his feet in a smooth surge, slim knives glittering in both his hands.

“How the fuck did you find me,” he snarls, and his eyes dart to Meg, then down the wash, where Benny’s bulk is just visible.

“I’d say ‘magic,’ but it’s probably not a joking matter. I have my ways. You’ve had your run, Sub, and it was a good one, but we’re going to take you home.” Castiel takes a few steps towards him.

“You’re not. I’m fucking leaving. Don’t even think about touching me.” Dean is deadly serious, and those knives follow his every move.

“Boss,” Meg warns behind him.

“It’s all right,” he says. He cocks his head and looks at Dean. “So, your given word means so little to you? I had thought you a better man than that.”

“What?” That’s clearly thrown Dean off his stride.

“Your signature. You signed the transfer papers. You agreed to come into my care until you could be returned to health, and Dean, you are not even close yet. Clearly.”

“I--I didn’t understand. I was, my dad, I didn’t,” Dean stutters. The blades don’t falter, but some of the fierceness leaves his gaze.

“We can overpower you.” It’s a simple fact, and Castiel presents it as such. “There are three of us, and you are tired, depleted, and unwell. I do not underestimate you; I know you would fight us hard, and well, and probably cause major injuries, but we would prevail. Even without that though, I would prefer to have you come with us willingly. As you came the first time. Come home.”

“Will I be punished?” A much smaller voice from the boy, and Castiel steps closer, pleased.

“Absolutely,” he answers without hesitation. “This is appalling, dishonest, thoughtless behavior.”

Dean winces, and his eyes flick rapidly over them, moving as fast as his thoughts.


“You hurt me too much,” he blurts out. It’s so patently far from whatever caused the problem that Castiel can hear Meg swallow a snort behind him.

“On the contrary, my sweet,” he says, calmly, “I think perhaps I did not hurt you enough. Firm, clear boundaries are my responsibility, and I apologize that your needs in this were obviously not met. I will do better. Put the knives down, Dean. It’s time to go.”

“Okay,” Dean says, and then startles, like he wasn’t expecting to say that. He jerks his blades back up from where they had relaxed. “On one condition.”

“I’ll hear it,” Castiel allows.

“Don’t...don’t tell my dad that I ran, and that you caught me?” It’s a plea, more than an ultimatum. From the heart, and Castiel’s eyebrows shoot up. There’s so much to unpack, here. Is he more ashamed of running, or that he was caught? And does Dean believe Castiel is sending reports home? Why would he?

“I swear I will not,” he promises readily. “And you will come clean about what prompted your late-night adventure.” It’s not really a question, and Dean’s head drops in acquiescence. Finally, his hands fall, those wicked, needle-point blades point at the ground, and Castiel walks to him and gently takes them from him.

Benny and Meg are at his side instantly, ready.

“Water, Meg,” he orders, and she digs the big water bottle out of the bag, holds it to Dean, who takes it with hands that have a visible tremble. He gulps the water desperately, letting it run from the corners of his mouth and streak through the dust on his neck.

“Leave me the bag. Fetch the car, please. And can you phone the house to tell them we will be returning shortly? Thank you, my dear. Benny and I will meet you at the road with Dean.” He sends her off with a smile, and turns back to Dean, who is just standing now, looking lost.

“Strip, Dean.”

Shocked, big green eyes fly to his face. “You’re...you’re going to whip me here?”

“Of course not. We are going home, and you will bathe, and eat, and rest. But this degree of defiance needs to be addressed immediately, and if you decide to change your mind, you won’t get very far naked. Clothes off.”

“I won’t run!” Dean protests, even as his hands pluck at the hem of his t-shirt.

“Not naked, you won’t,” Castiel agrees. “Now, Dean.”

Under Benny’s watchful, silent gaze, Dean kicks off his one remaining shoe, shoves off his jeans and boxers, and skins out of his t-shirt, while Castiel digs in his bag. Coming up with a sturdy, heavy-duty brown leather collar and leash, he buckles the collar around Dean’s neck without ceremony.

Dean’s breath hitches in his throat.

“Benny?” He hands the big man Dean’s leash, and re-packs the bag, piling Dean’s filthy clothes on top. “All right. Back to the road.”

“Come on, little brother,” Benny says, not unsympathetically. Dean actually steps close to him without protest, and Castiel smiles a little to himself. Having a low-level Dominant like Benny on staff comes in handy. Dean can take comfort in his dynamic without being overwhelmed by his authority, and Castiel leads the way back to the car.

Dawn is painting everything in shades of gray by the time they pull up to the house, and even Castiel is starting to feel the fatigue of the night’s exertions. Dean is actually asleep in the back seat, leaning against the window, and he jumps when Meg shakes him awake. The relief on his face when he looks out and sees the house warms something inside Castiel.

“Benny, please send everyone to bed, and then follow. Tomorrow will be a day of rest, Monday or not. Meg, if you can speak to Angelique about having simple cold food available, nothing else is required, and I will talk to you tomorrow about scheduling Dean’s formal punishment with the staff. Thank you both for all your help, you are exceptional, and I could not be more grateful.” They grin and salute, and disappear into the house.

With a firm tug on the leash, Castiel brings Dean out of the car, and takes him home.

Chapter Text

Dean is exhausted. His eyes keep falling closed as Novak scrubs him down in a warm bath, doctors his blisters and scrapes, and pours some food into him, and Dean goes along with it all. He’s just too damn tired. It’s not the same as last night, when he’d felt like he was looking at the world though a tiny peephole from the bottom of a deep well; that had been terrifying, distantly, even at the time. Now he’s simply exhausted, which is familiar enough.

He’d made his play, and failed. There’s something peaceful about that, somehow.

“You’re not the first Submissive to try to run from training, you know,” Novak’s voice is startling in the silence; he’s speaking as he tidies the food dishes on the sideboard, and Dean looks up at him from the pillow where he’s been put in Wait. “But you are, by far, the most successful. If it weren’t for the awful inconvenience, and the danger you put yourself in, I’d be impressed.” Novak’s almost smiling, and Dean hesitantly smiles back at him.

“Given your evident skill set, you’ll be sleeping in your collar, and locked to the bed for the foreseeable future. Up on the bed, Dean. We’ll get a few hours at least, I believe we are both in desperate need.” As Dean climbs onto the bed, Novak pops open a small door in the headboard, revealing the wrought iron frame. There’s a heavy D-ring attached, with a padlock, and Novak snaps it shut around the handle of Dean’s leash.

Dean winces at the final-sounding snap of the lock. He can’t even see the padlock that secures the leash to the collar and the collar to his neck; he is well and truly secure. At least the leash is long enough that he can lie down without discomfort, and he follows Novak’s urging and curls under the blankets, back where he’d begun all those hours ago.

“We’ll talk later in the morning, sweetheart. Sleep now.” He can’t help but obey.

***

Dean has never been quick to alertness in the mornings. Being yanked from sleep by a hand dragging him from the bed, though, is shocking and disorienting enough to make him even more confused. He blinks, kicks out, tries to twist away, and suddenly finds his feet on the floor as he’s marched across the room to a low bench set up in front of the fireplace.

“What, what, sir-” his voice is thick with sleep.

“On the spanking bench, Dean. Hold the grips, do not let go. We will begin this morning the right way.” Novak’s voice is pure iron, like Dean has never heard from him, and instinctively, Dean scrambles to obey. Brain still fuzzy and confused, he crawls onto the bench, his knees supported by the padded slats, the wide bench supporting his hips and tipping his torso so his head is slightly angled towards the floor.

“Gotta pee...gotta brush my teeth…” he mumbles, confused by the speed of everything, though adrenaline is starting to kick his heartrate up, clear his head.

“Hold it,” Novak says, hard. “You will take ten with the strap to start. Say yes, sir.”

The strap? He hasn’t been strapped here before. Dean goes tense. “Yessir, but-”

SMACK. It’s different than the switch, wider, less sting, but a moment after impact there’s a deep, thudding pain. Dean gasps and twitches. Novak sets a fast, steady rhythm. It’s not mind-melting, nasty fire like the switch but by the tenth strike Dean is squirming, teeth clenched, and the skin between the top of his ass and high on his thighs feels hot and thin and tender, fragile.

“That is ten. Dean, look at me.” Dean pries his eyes open, are they done? Novak is standing beside him, showing him the switch. Oh no. Oh no.

“You will have fifteen with the switch for breaking your word, disobedience, disrespect, placing yourself in danger, placing my staff in danger, and dishonesty. Tonight at dinner my staff will have leave to spank you once each for their trouble as well. Say yes sir.” Still that iron voice and his eyes are hard, unyielding, like his face. Dean feels something dangerously like a sob rise in his throat. He knows he earned this, he deserves it, he knows it, but not the switch, anything but that on his already-tender ass--

“Yes Sir,” he squeaks, and Novak nods and moves behind him. Dean tenses and braces and tries to prepare himself--

The switch falls, and Dean screams. He doesn’t know why now, when never before. Maybe it’s that he’s still disoriented from sleep, maybe it’s that he really does feel bad about making Sir chase him. The guilt hurts, aches, makes him feel sick and wrong inside. But in that moment something in his mind feels like it clicks over to a new setting with an almost audible snap, and Dean...lets go.

“I’msorry I’msorry,” he gasps, hips trying to dig through the spanking bench to escape the pain from the welt. The second blow falls with a snap, and Dean lurches forward, scrambling, and the third comes, he can feel his eyes fill with tears and then the fourth lands and he’s sobbing wildly.

“Sir I’m sorry I’m so sorry I’m sorry!” he shrieks, the fifth and sixth falling and the pain washing through him, clearing his mind of everything but agony and remorse. He twists his whole body violently, trying to escape the next strike.

“I know, sweetheart,” Sir says gently, and hits him again. “You’re being punished now, and all will be forgiven. Let it out.”

Tears are wet on his face, his lips, and his nose is stuffed full of them, and he’s panting through his mouth and he’s lost count, it’s endless, just blow after blow and he’s finally unable to even react, just limp and pliant across the bench. Each strike with the switch gets a wail and a fresh apology, sobbed aloud, somewhere in his mind he knows it, but utterly overwhelmed, he can only let it happen.

Finally there are no more. His ass is searing agony, it feels like it must be twice its normal size, probably covered in blisters and broken skin. He tries to breathe but every inhale hitches brokenly and every exhale brings more tears. He’s so sorry. He was so bad, and so disobedient, and he disappointed Sir so deeply. The pain in his butt at least eases that pain away, but it’s only really soothed when Sir gently lifts him from the bench and into his arms. He holds him close, gentle, and pets him, murmuring sweet things until Dean's breathing comes back to something like normal.

“S-so sorry,” he whimpers, and Sir smiles at him, the nice warm smile, and stokes his hair back from his sweaty face. Gentle thumbs brush tears off his eyelashes and Sir presses kisses to his cheeks, his nose. It feels like a blessing, like absolution, and warmth spreads through Dean’s chest, his mind.

“You are forgiven, lovely. I know you will not behave so poorly again.”

“N-n-never,” Dean swears on a hiccuping breath, and Sir’s smile gets a little wider.

“My good boy. I know you will try, at least. I am so proud of how you took your punishment, Dean. Let’s finish our morning properly and then we’ll have a bath together. On the bed, please. Present.”

Dean’s dizzy, fuzzy mind stalls out at that. He blinks. His Sir is naked, holding Dean a little away from himself now. His huge cock is standing out from his body, so hard it almost looks angry.

Dean crumples into sobs again. “Sir, please…”

“Dean. Do I need to put you back on the spanking bench?” Sir’s voice holds an awful gentleness, and Dean shakes his head wildly in denial.

“N-no, no no Sir.” He walks very gingerly towards the bed, every step jolting pain through his butt, and carefully climbs up. His arms and legs are trembling, his mind is just static. He’s clinging to the warmth of Sir’s forgiveness, the vague idea that last time was painful but ultimately good, as he carefully moves into position at the edge of the bed.

“Good boy.” Sir’s warm hand strokes his lower back, urging it into a deeper curve, even as he feels the syringe penetrate him, the strange alien feeling of lubricant coating him inside. “Find the place inside you that delights in giving pleasure to your Dominant through sacrifice, sweetheart. I promise it is there. It is important for you to find and accept this part of you, it’s critical. And you do please me very much like this.”

Dean whimpers. He shoves his face into the bedspread. When he feels Sir press close behind him, the heat of his skin an unbearable sensation on Dean’s raw ass, he can't hold back any more. “Nooooo,” he wails, into the fabric. “No, don’t, Sir please please please, I can’t, please don’t...”

“You may protest all you like, but understand that this is happening,” that stern voice behind him, and Dean shivers at the words, buries his face deeper, and lets himself sob.  It helps, it feels like the fear is coming out of him with the tears.

The pain is sharp and savage when Sir’s cock penetrates him, that first breach shocking his breath out of him, his hands clawing helplessly at the bed. But hearing Sir’s moan, deep and rich with pleasure, does something to him. Sir pulls out and thrusts in again more deeply, and it burns just as badly, but it feels more distant, somehow, as waves of calm and the urge to surrender roll through him. He’s always fought them back before, but shock and pain and tears and remorse have cracked all his defenses. He lets them in this time, lets them soothe the frantic impulse to fight and flee. The next thrust cores into him, relentless, driving his breath out of him in a pained sound he doesn’t recognize, but his lower spine and tailbone feel soft, hot, swollen somehow; his hips want to spread wider. Sir’s cock drags out of him, fierce and harsh and so big, harder even than before; Dean knows that means Sir is even more aroused.

A strange warmth shivers up his spine, though his mind. His thoughts slow from their frantic tumble into calm, slow, syrup-sweet drops: his Sir is happy with him. He is forgiven. He is pleasing. He is serving well.

“Good boy, oh, excellent boy, you are so perfect, so beautiful, so sweet for me,” he hears a moment later, the words falling into his ears like healing balm, and Dean realizes vaguely that he’s settled into the fully relaxed pose of Present like in the training room, his back deeply arched, thighs obscenely wide. Sir’s cock is splitting him open over and over and over again, fucking him deep and hard, now, all the way in to his gut, so full he can barely breathe, a biting, stabbing burn with every advance and retreat, but it’s all becoming one with the pain of his whipping, the purring pleasure of Sir's praise, the sweet dragging, drugging pull he feels to submit, submit, submit.

Dean surrenders.

Chapter Text

Castiel can sense it the instant Dean submits. Most Subs drop easily to subspace during a scene or when interacting with their Dominant, but Dean has been fighting it every step of the way, every moment. When he finally goes down, the change is so dramatic, Castiel almost chokes on air.

The boy goes liquid under him. Back arching, hips yearning up towards him, shoulders round and soft. The small sounds of pain that his cock is forcing from that sweet, plush mouth go from harsh and broken to breathless, effortless, almost needy. Castiel slows his hips, dragging his cock out and leaving just the head buried in Dean’s hole, sore and strained and red, the reflexive, clenching spasms a glorious massage around him.

The rush of it is almost blinding. He almost hadn’t done this. The morning's punishment was the most severe Dean has taken so far, and rough sex on top of it...but his instincts had been demanding that he push a little further, a little deeper, once Dean broke down, wept, showed true remorse and cleansing. And his instincts have been vindicated. Dean has truly submitted to him, is under him, open and vulnerable, and Castiel has to take a deep, steadying breath. He must not dominate too far, too hard, must not be too rough, lest too much pain force the boy back up out of subspace, must keep himself in check. It’s a familiar mantra, but it’s never been a struggle like this. He wants to ruin this beautiful boy beneath him, lick his tears, swallow his screams--

With a long, powerful thrust, he sheathes himself to the root again, changing the angle so he can rest more of his weight on Dean. Mount him properly. Now he can see his face, turned to the side. It’s wet with tears, flushed, his eyes wide and dazed, blinking slowly, his mouth hanging a little open. Castiel ruts himself in, little screws with his hips without withdrawing, and bites down on the back of his neck. Dean cries out, a thin, high noise that’s almost a squeal, and Castiel feels a sudden wetness against his knees, where they’re braced between Dean’s.

His Sub has wet, bladder releasing, soaking the bedspread beneath him. A demonstration of deepest, most absolute submission, and even then, rare. Castiel wants to shout with it, roar it to the world, but he knows Dean, so new to all of this, must be close to the very edge of his endurance.

“My star,” he murmurs to Dean instead, resuming his thrusts, faster, chasing orgasm now. “My wonderful boy, how proud I am, there are no words. Dean, you have surpassed every hope. You are so strong, so good for me, so precious.” He feels his orgasm rise out of him like a tide, every inch of him singing, his skin alight with power, alive, rampant, fulfilled. Surging forward into Dean's tight, clutching heat he comes, shouting, spurting deep, cock jerking again and again as his balls empty themselves into Dean’s pliant body.

He rolls them to their sides as soon as he can, still shuddering a little with aftershocks but needing Dean in his arms. Gently withdrawing, ignoring Dean’s quiet moan of protest, he eases them up the bed, away from the wet spot, kicking the soiled bedding away.

Drawing Dean to his chest, he cradles him close, tucked under his chin as he settles comfortably against the pillows. Dean is quiet, breathing softly with his face pressed into Castiel’s shoulder, hands curled to his chest. Castiel runs gentle fingers through his hair, petting him, scratching gently, stroking down his neck and following the curve of his spine. Long, calming, soothing strokes.

When Dean finally stirs and rouses, it has been at least fifteen minutes, and Castiel has never stopped petting him, or murmuring praise to him. He shifts, stretches a little, and blinks, like he’s waking up from sleep.

“Welcome back, sweetheart,” Castiel says, smiling. His hand, gently cupping Dean's breast, checks his heart rate, and it has slowed to near-normal. He palms Dean's soft cock next, holding it with just a little pressure, bringing Dean back into his body little by little. He kneads it a few times, then moves on to his belly, rubbing the soft skin there firmly.

“Wuzzat,” Dean is still clearly a little fuzzy, though his eyes are clear again.

“That was subspace, lovely. I know it was difficult for you to get there, and I’m so proud of you. That was wonderful, Dean. So, so good.”

Dean flushes, and ducks his head, still sweet with the remnants of submission. “Felt good,” he mutters. “Amazing, actually.”

Privately, Castiel sighs in relief. He’s met a few Submissives who are neutral or even have a dislike of subspace, for their own personal reasons, and he’s thrilled that Dean is not one of them.

“I’m very glad. We’re a bit messy, are you feeling up to a bath? I will join you, I’ll be with you,” he adds quickly, as Dean’s hands clamp tight around his arm. The boy nods hesitantly.

Castiel can’t believe how sweet Dean is like this. He’s almost shy, peeking up at Castiel as they shift around, get untangled, Dean very very carefully, favoring his bottom. Castiel gets an arm free to pick up his phone as Dean leans on the other, getting his feet under him, and dials the kitchen.

“Yes, can you please send Claudia up with fresh bedding in the Master? Thank you.” He sets the phone back down in time to see Dean notice the blankets and sheets on the floor, and watch him pale as he stares at them with a look of dawning horror.

“Dean, no. You look at me right now.” Obediently, Dean does, though he still looks shocked.

“Did I...oh my god…” he says, weakly, and Castiel takes him by the shoulders firmly. Goddammit, they really must do something about the curricula in the public school health classes!

“It was perfect and wonderful, Dean. It’s a natural reaction to deep submission and it was beautiful. I loved it. It doesn’t happen often, but when it does, it’s to be cherished and celebrated. I will not permit you to feel shame about this, do you understand?”

“The mattress,” Dean protests, though he’s already brightening a little.

“Has a marvelous protector. This is nothing laundry cannot fix.” Claudia, the housekeeper, pauses in the open doorway. He’d left it open deliberately, ensuring that his household, affected by Dean’s thoughtlessness, could hear his atonement for it if they chose. Now he’s glad because he can wave her away. She smiles at him and nods, and moves quietly from the door.

“And you didn’t let me take a leak, before,” Dean remembers, definitely coming back to himself, now. Castiel nearly rolls his eyes.

“Indeed. And now a bath. We both need a shave, and I’ll have a look at those blisters again.” Dean follows eagerly enough, reassured, or possibly just repressing. He shaves his face and brushes his teeth quietly as the large soaking tub fills, and when he looks warily at the tub, Castiel offers him a hand mirror. His backside is a rainbow of color, it’s true. Blue bruising has started in a few choice spots, and shades from pink to red to purple decorate the rest of it in stripes. But the skin never came close to breaking.

Dean looks at the mirror one more time like he can’t believe his eyes, and then sets it aside. He eases himself into the water, hissing as it touches tender skin, but once he’s in he nudges eagerly against Castiel, actively seeking out contact for the first time, moving in until Castiel lifts his arm and cradles him close.

“Would you like to learn Krav Maga?” He’s feeling a gut-deep urge to please Dean, make him smile, and surely martial arts will appeal.

“Oh my god, are you serious?” Dean turns in his arms, incredulous, smiling. “Of course!” Every dominant instinct in Castiel preens and puffs up. “I mean, yes sir, thank you!”

“We’ll start next week. I generally train four or five days a week, you can join me after breakfast.” He nudges Dean’s bare hip with his knee, where they’re pressed together. “You can even wear clothes.”

“Be still my heart,” Dean sasses back, but he’s truly pleased, Castiel can tell. He grabs a cloth and soap and starts to bathe the boy, much more slowly and carefully than last night’s brisk scrubdown. Speaking of which.

“I believe you owe me an explanation, before it gets too much later,” he reminds Dean, gently but firmly. He runs the cloth down his arm, careful of some healing scratches. “Your distress before bed, and then your mad dash into the wilderness.”

“I, um.” The backs of Dean’s ears turn bright red, and he ducks his head. “You know I was going to call my family, right?”

“On the landline, yes,” Castiel soaps each finger on Dean’s left hand, then pulls the boy to rest back against his chest, so he can wash his front more easily. And so Dean can talk, and look away. Dean squirms a little, but then settles, the skin of his ass toasty-hot in the cradle of Castiel’s hips.

“On the landline, right. So I talked to my dad, and he said some stuff. About when I’m done here, stuff about how he’s planning to make me find a contract when my papers get signed back over to him.” Even with all Castiel’s care, the boy is tightening up like he’s being wound on a spring. But Castiel pauses at his words.

“Wait a moment. Dean, your papers will not be returned to your father. When you have completed your training, you’ll return to Austin, of course, to be near your family, but John Winchester cannot be your Dominant of record again.”

“What?” Dean tries to face him again and fails, too slippery, and Castiel wraps him up in his arms.

“For one thing, he’s a Switch, and doesn’t have the appropriate dynamic or instincts to dominate you properly. Even if he did, you’ve already told me that there is no sexual component to your relationship, and Dean, your submission is deeply sexual. Going back into that relationship would put you right back where we started.” He noses into the short hair behind Dean’s ear, kisses him gently there. “Part of your training will include help and guidance finding the right Dominant for you, a good match. Understanding your own needs and wants and how they interact with those of others. I won’t sign your Record papers over until you are fully comfortable with your choice, baby.”

Dean seems stunned. Or at least, speechless. Castiel easily lifts and floats him a little way in the deep tub, and turns him, to see his face, and yes, he’s definitely shocked.

“Once again, a situation where you could have simply asked me, and avoided a great deal of trouble.” It’s a pattern Castiel is not fond of.

“Shit,” Dean breathes, then blinks. “I am so sorry. I just thought-- I mean. Training is one thing but that’s my whole life, forever, and I can’t, I can’t even imagine it...My dad was talking about this matchmaking service, and said if my Dominant didn’t want me to drive then that was all right and proper and whatever, which is such bullshit, you know? I rebuilt that car with my own two--”

Castiel cuts off the torrent of indignant words with a kiss. Not something he usually does with trainee Subs, but Dean all warm and pink and wet in the bath, lit up with worries relieved, and complaining? Castiel would challenge many a stronger man than he to resist. And oh, Dean’s mouth is as sinfully wonderful as it looks.

Chapter Text

The ground is shaky under Dean’s feet. He feels kind of fragile, and sensitive, and raw in places other than his ass, and Sir toweling him off and gently fastening his collar on after the bath feels really good, safe, somehow.

He kneels obediently at lunch, and takes his cold chicken and fresh bread and potatoes from Sir’s hand without protest. It’s something to do while his mind works furiously, and he doesn’t want to get in trouble again. Maybe a benefit of this whole Sub thing; he can just follow orders and be okay, and let his mind go other places for a while.

His dad isn’t going to be his Dominant anymore. Not ever.

Maybe that’s a good thing. Dad’s never been big on what he calls “subby Subs,” though he always taught Dean and Sam to respect everyone and their choices in life no matter what. But life on the road is tough, Dean knows, and pillows and petting and soft things don’t really factor in.

Dean’s not sure he can be that kind of Sub anyway, though he’s not sure how that will work, with his new orientation. But what if that’s okay? He’s all turned around in his mind. Sir wants to teach him Krav Maga. Why would he teach a Sub Krav Maga if he was supposed to stay home and scrub the kitchen floor on his hands and knees with a dildo up his ass all day?

He only really snaps out of his whirl of thoughts when they’re in the little medical room and Sir has him up on the table again. Every day so far, he’s gotta get his finger stuck by a tiny needle and give some blood, for those tests or whatever.

He watches the tiny ruby drop well up, Sir pulls it into one of those tester things, and then it’s over. No big deal.

He realizes that his leash is hooked to a ring on the wall around the same time as Sir makes a happy noise and claps his hands once.

“You’re doing it, Dean. Well done!” Sir’s grinning at him, pleased, and Dean smiles back reflexively, straightening as a bolt of pure pleasure hits him in reaction to the Dom’s praise.

“Awesome! But doing what, sir?” He’s curious now. Distracted from his own thoughts, he watches Sir type a few lines into his computer, then turn the chair so he’s facing Dean. He rolls the chair over closer, puts his hands on Dean’s thighs, warm.

“Your Subutanol levels finally started to drop, and Rewardarin is much higher today. I think it’s because you finally reached real subspace. And you let yourself go during punishment and allowed it to do its job, and your body is finally responding as it should.” Sir’s blue eyes are twinkling a little as he looks up at Dean. “There’s a happy and healthy Submissive in there after all.”

Dean scoffs a little, looking away. Tears are a sign of weakness, he’s known that forever, but he can’t argue with the fact that he feels like he’s lost about fifty pounds of accumulated guilt and bad feelings since this morning. And subspace was frigging awesome, like every good drug Dean’s ever sampled all rolled up into one, mainlined into a vein, without the hangover. Just thinking about it makes his mouth water, and he swallows hard.

Sir is watching him with a shrewdness that Dean sometimes thinks means he’s reading his mind, but he doesn’t say anything immediately. Just cleans up the sample, unhooks Dean’s leash, and then moves over to the big, soft-looking armchair. He’s wearing what Dean thinks of as his training clothes...soft cotton pants with a drawstring, a v-neck long-sleeved cotton shirt.

“Here, Dean. On my lap.” Dean slides off the table and, feeling weirdly shy just like he has been since this morning, slips into Sir’s waiting hold. He feels too big for it, awkward, but Sir doesn’t seem to care, and wraps his arms around him, pulling him in nice and tight and secure. Dean relaxes, little by little.

“We are informal in this room, remember? I think we’ll take a little time every day for you to ask me any questions you have. There will be no shame or embarrassment in anything you ask, and I will answer to the best of my abilities. Anything at all that I can help you understand, I will.”

“I don’t even know what to ask!” John had always taught them that knowledge is power. But so much of the information on Subs out there, online and on TV and in magazines is bullshit, he knows it, because it doesn’t sound anything like him at all.

“Whatever comes to mind,” Sir coaxes. His elegant long fingers tease at the top of Dean’s groin, scratching gently through the curls of hair there, and Dean melts a little.

“Okay, okay. The pissing thing, I don’t get it.” Dean’s face gets hot with embarrassment, even remembering it. In the moment it had felt like an orgasm, a relief and ejaculation of pressure and a bone-deep pleasure that had almost knocked him flat. But he knows he was hurting too much to even think about getting hard. And then to realize what it really was. Fuck. He’s not a baby.

“Hmm, yes,” Sir sounds amused behind him, and he shifts Dean a little so he’s sideways across his lap, weight on his thighs, sore ass free of pressure. Dean huffs in relief, and listens to the ‘medical lecture voice,’ even as Sir begins to squeeze and stroke one of his boobs, the other hand warm and flat over his hipbone. It’s super distracting.

“As I told you, it pleased me very much. Subspace is...special. It’s a mental and physical state where Submissives are most in touch with that part of themselves that exists to serve, to please, and to gratefully receive the will of their Dominant. When a Sub, especially an inexperienced one, drops suddenly and completely, as you did this morning, sometimes all the body’s sphincters open instinctively into a receptive state. Combined with the repeated impact against your bladder, the result was what is known as Submissive wetting. It’s not something you can control, sweetheart, and it is a compliment to me that your body offered it up to me.”

Dean ducks his head, face still hot. “Good thing it doesn’t happen all the time,” he grumbles, squirming a little as the hand on his tit starts working him up. “The laundry bill would be nuts.”

Sir laughs, a warm sound. “It would be worth it for some of us. And plenty of couples regularly engage in fluids play, be it watersports or other things. Laundry is really not that much of a concern.” His fingers pull and pluck Dean’s nipple, like it’s nothing, like that doesn’t reach down into Dean’s belly as if there’s a cord of heat connecting his cock directly to his breast. Dean squirms again, mostly hard, now, and Sir’s hand on his hipbone tightens to hold him still.

“Okay, okay. Fine, I won’t freak out about it. Much.” Dean tries to sound aggrieved, but his voice is breathy, light, he barely recognizes it. He searches for another question amid the rising heat of arousal.

“Oooh,” a particularly deep pull has his hips trying to lift again. “Okay. If I’m all really Submissive, on my tests and everything, why doesn’t pain feel good?” He dips his chin so he can watch Sir play with him.

“No matter what you see in the media, and yes, I know, it’s all very whips and chains and screaming orgasms at the end of a beating, some Submissives are not masochists. Many others are only mild masochists.” Sir’s gravelly voice sounds even deeper when Dean is resting against his chest like this. “The wiring that translates pain to pleasure isn’t present in everyone. I even know some Dominant masochists, so it’s not purely related to dynamic, either.” He releases Dean’s nipple, now peaked and swollen. Dean isn’t sure if his sigh is relief or disappointment.

“Dean, I want you to pay attention, now.” He looks up, meets Sir’s serious eyes. “Because you don’t find any sexual pleasure in pain, it makes your punishments much more straightforward for your Dominant, which simplifies your training. But it also means you need to be open-minded in other areas of sexuality. A sadist/masochist pairing is the most common, but there are many, many other areas where a Dominant and Submissive can find common ground and mutual pleasure and satisfaction.”

“Okay,” Dean agrees, slowly. He’s not sure exactly what that means, but it sounds all right.

“You’ll understand more as your training progresses, I promise.” Sir palms his cock, just like that. Dean sucks in a breath, startled, and shifts to give him more room.

“Keep asking questions and I won’t stop,” Sir coaxes him, those long fingers tracing up the vein on the underside of his cock, torturously.

“Uhh. Ohh. Um, what do YOU like?” He’s squirming hard, now, and barely notices Sir reaching for the lubricant, slicking up his other hand.

“I won’t share my personal fetishes, because I don’t want them to influence your reactions as we experiment,” Sir explains calmly. A wet finger touches his sore hole and he flinches hard. “Shhh, lovely. This will feel good, I promise. Just a finger, to help you learn to come from here.” The finger presses inside, smooth and slick, and the sting is barely noticeable. Dean relaxes a little. When it starts sliding in and out of him, feeling so dirty and good, matching the stroking hand on his cock, he has to close his eyes and let his head fall back.

He had no idea it could feel like this.

“In core needs, I’m a sadist,” Sir continues, like Dean isn’t trying to get his knees wider apart on his lap, like Dean’s shameless humping into his hand is just...normal. “I take intense pleasure from the sexual pain and fear of my partner. Here, sweetheart, like this.” The long finger, hot and probing, curls up inside Dean and the hand on his cock is just gently holding and pulling the slick, hard, swollen head, now, and Dean feels heat pooling in his groin, between his legs. In his cock and balls, like normal, but also in his ass, down deep inside, a deeper, fuller, slower-building need.

“You-you like hurting people,” he gets out. He blinks his eyes open, looking at Sir blurrily. “It gets you off?”

“When the context is right, yes,” Sir confirms, stroking Dean inside, touching more firmly every time. “Walking up to a stranger on the street and slapping her breast would do nothing for me. But the same scenario with a Submissive in my bed is very arousing.”

Dean’s fuzzy mind turns that over. He feels like he should be nervous around Sir now or something, but he’s too distracted, and something doesn’t make sense... “Wait. If you slap her and it feels good to her, doesn’t that kind of ruin it for you? It’s not really pain then, is it?”

Anyone less sensitive than Dean, anyone not trained to pay attention by a Hunter, might have missed the way Sir’s hands go still for an instant, then keep moving. Dean notices, but can’t make sense of it in the middle of the tide of pleasure about to pull him under. And Sir is answering him anyway.

“For the majority, no. Sadism is more than satisfied by inflicting the pain. How the Submissive’s body translates the sensation doesn’t alter their fulfillment, which is a fortunate thing for the relationships of those sadists and masochists.”

He smiles down at Dean. “You can come, sweetheart. Come for me, I know you need it. You have earned the reward today, you’ve been so good for me.”

Dean comes, hips pumping, working back on that finger just as hard as he’s trying to get more friction on his cock. It feels incredible, like his whole body is coming at the same time, all up his spine and then back down in a slow wave of hot, violent pleasure that crests as he clenches and spurts, it’s been so long it almost hurts it feels so good, shot after shot of come pulsing across Sir’s hand and his own belly.

“Good boy, that was lovely,” Sir praises him, and that’s almost as good as the orgasm, what the fuck? Dean blinks his eyes open again and bites his lip, shivering with overstimulation as Sir holds his cock between two fingers and gives it a strong, stripping pull, a few beads of semen dribbling from the head, milked free. “Nice and clean, good,” he hums, and wipes his hand on Dean’s thigh.

When he doesn’t move or shift in the next few moments, Dean tries to get some moisture back into his mouth, and licks his lips, and wiggles a little. “Am I supposed to keep asking questions?”

“You’re supposed to thank me politely for allowing you to come, and then, yes, keep asking questions.” Sir pinches his buttcheek sharply, and Dean jumps with a yelp.

“Thank you sir! I didn’t know. Um.” He tries to pull his orgasm-drunk brain back online. But now all he can think about is orgasms. “I should’ve been super mad that you didn’t let me come yesterday in the training room. And with the whole chastity thing? But I wasn’t, it felt fine. Almost good. I was really confused.”

“Ah, the core conundrum of sexual Submission,” Sir chuckles again. When Dean peeks at him, he’s looking relaxed and content, holding Dean, even though Dean's covered in spunk and still kind of wiggly. His face is relaxed and those hooded blue eyes aren’t tense at all. “The more submissive you are, the less your focus will be on your own pleasure, and the more you will need to concentrate only on fulfilling your Dominant’s desires. It’s why matches between levels are quite important, though there are exceptions that work out.

"The higher-level Dominants will also focus intensely on their own satisfaction and satiation, and control and even deny their Sub’s orgasms to a much more severe degree. But both parties find a huge amount of contentment, security, and even joy in that exchange. When I told you that traditional sexual release was only one type of pleasure to be found in submission, that’s part of what I meant. Some high level Subs may even feel anxious or stressed when they believe their Dominant is trying to pleasure them at the expense of his or her own gratification.”

“Seriously?” Dean wrinkles his nose. He can’t really imagine that.

“Seriously,” Sir confirms. “Imagine that we are together at bedtime, but that instead of fucking you, I lay you gently down on your back. Slide down between your legs, stroking your thighs. Gently take your cock into my mouth as you hold my hair, sucking, licking down the shaft, sliding the--”

“Ugh! Stop, stop!” Agitated, Dean sits up straight. That’s just..it’s wrong. It’s so wrong. It makes him almost nauseated, thinking about it.

Sir doesn’t say anything, but his silence is very smug.

“I still like feeling good, though?” It’s almost a question. But Dean definitely does. And he loves blowjobs and orgasms.

“Of course you do. And any Dominant worth your time will ensure that you do, and that you are happy and fulfilled. Orgasm may just be a rare and special way to feel good, depending on your relationship. Or, who knows, they may enjoy making you come until you beg them to stop the pain. Or somewhere in between.” He snugs Dean close in a hug, and then with a last pat to his hip, stands him up on his feet.

“Why am I still wearing this collar and leash?” Dean’s going to keep asking questions, since it seems like his free pass is coming to an end.

“You’ll be wearing that full time for the next week, whenever we are not actively scening,” Sir tells him, handing him a towel from the cabinet so he can clean up. “Your free time will be chaperoned, and when your leash is not being held by myself or my staff, it will be clipped to a restraint. If you need to move to another room, or outside the range of the leash, you will kneel to whoever is holding it, and politely ask them to help you.”

Dean’s jaw drops open. He should feel angry, he knows. He should feel trapped, smothered, should be yelling his face off, but though he’s frustrated and more than a little scared, the real anger is far away. Distant.

“You said I was forgiven,” he argues, folding his arms across his chest.

“You are. I am not angry with you, sweetheart, and this is not a punishment. It is training, and it is to help you accept and submit to your situation.” Sir cups his face in a gentle hand, and Dean momentarily hopes he’s going to get another of those incredible, mind-blowing, toe-curling kisses. But Sir just smiles at him and leads him out of the warm little room.

Chapter Text

“Settle,” Sir growls at him, and Dean subsides back down to his knees, and he tries to calm himself, he really does. Dinner is good, big sandwiches and french fries, all simple things since Sir gave the staff an easy day. Because of Dean, he thinks miserably, and squirms again, crossing his ankles behind him and rubbing his bare feet together, the newly-sharpened guilt pangs digging at him.

“The discipline you are getting from my staff shortly will not prevent me from enforcing dinner manners, Dean. This is your final warning,” Sir gives his leash a snap, and Dean actually whines, forcing himself back into Wait position.

“Eat.” Sir holds a piece of the sandwich to him, and Dean takes it, chews and swallows. It’s like ash in his mouth. But he manages to hold still through a few more bites, and french fries, and a few apple slices.

After position training today, Sir had explained that his seven-person staff will be allowed to strike Dean’s bottom (Sir’s word) once each, with their choice of paddle, crop, or strap. That Dean had inconvenienced them all deeply and upset and disturbed them, and he has to atone. That he will apologize to them and ask them to punish him. Dean has been fretting himself into a mass of nerves, deeper and deeper, ever since. He drinks the water Sir holds to his lips, but his eyes keep darting to the doorway, to see if any of the staff are already waiting there.

Sir sighs, and Dean’s eyes fly back to his face. He is definitely annoyed, but not angry, Dean thinks.

“I shouldn’t have mentioned anything until after you’d eaten,” Sir’s grumble is more to himself than Dean, so Dean just stays still. He’s getting better at reading Sir’s moods. His bottom aches every time he moves, though, already so sore from this morning, and the thought of being punished further puts a knot in his throat that he can’t sit still and endure. He fidgets again.

“All right, that’s enough. Clearly, we must get this done, before you fly entirely to pieces.” Sir nods to someone Dean can’t see from where he’s kneeling, and snaps his fingers at Dean. “Up, follow me. Public punishments are held in the main sitting room.”

Heart in his throat, Dean follows. And when he sees the people gathered in the big room with all the chairs, and the wooden bench with heavy D-rings along one side with pride of place in the middle of the floor, he summons all his bravado and gets his chin up, refuses to slouch and hide.

Sir stops him when they’re facing the people. He knows Meg and Benny and has seen a few other faces. There’s Crowley, the masseur who doesn’t talk to him, and the small blond man he’s met in the hall. The others are a mystery. Sir puts a hand on his shoulder.

“Many of you know Dean already, and those of you who don’t were introduced by last night’s exciting events. Dean has something to say to you all.” Sir’s voice brooks no argument.

“I-” Dean has to clear his throat and start again. “I am very sorry for upsetting the house and disturbing you all last night.” He stares at a point past Benny’s head, he can’t look at any of them. “P-please punish me so I can be forgiven.”

“Very nice.” Sir leads him to the bench, helps him climb onto it. The wood is cold and unforgiving against his knees and hands. He loops Dean’s leash through one of the D-rings and pulls it tight, tugging Dean’s head down. “Dean, Present.”

The tears already standing in Dean’s eyes break free and fall down his cheeks. He obeys, though, going down on his elbows and putting his cheek down on his folded hands, lifting his hips and spreading his thighs, opening his most private, vulnerable places up to the eyes of these strangers because his Sir ordered it, because he has to make this right.

“Good boy.” Sir strokes his hair gently, soothing. “I will be right here, sweetheart. You will be fine.”

“Y-yes sir,” Dean whispers. Sir nods to someone behind him.

“Benny, go ahead.”

It’s definitely the strap, and it SMACKS across Dean’s butt so hard it rocks him forward almost off his knees. The pain hits that same instant, and he howls “I’M SORRY” into his arm, kicking instinctively, until the heavy hand on the back of his neck makes him go still.

“Present, Dean.” The stern voice must be obeyed. He pulls himself back into position, his heartbeat throbbing a wide stripe across his ass, face wet with tears now and breathing hard, but the guilty claws have started to release their grip on him.

“Ash.”

A paddle, it slaps down and he whimpers his apologies, hiding his face.

“Cole.” The strap again, and he screams, I’msorryI’msorry. Shameless now, just letting it out. The bad feelings lighten more, with every strike.

“Meg.” The crop, it’s a line of evil fire that steals his breath for a second, his remorse just a whimper.

“Crowley.” The crop, he hates it, another scream, hiccuping now through his sobs.

“Claudia.” The paddle, much harder this time, and over the crop welts; he howls again.

“Angelique.” He waits. Nothing happens for a long time, and it’s the last one, he needs to be done. Then there’s a little pat on his bottom, which hurts, sure, but nothing like the crop or strap or paddle would. Rousing himself, he peeks down past his own leg, and there’s a small old lady, dark hair mostly gone silver, with her hand on his rump, smiling at him. Then she twinkles up at his Sir.

“I can’t whip such a pretty tushie, Mister Castiel, not one that so much enjoys my cooking. Here, I spank instead.” She gives his cheek a small slap. He can barely feel it.

Dean’s giggle through his hiccuping sobs almost makes him choke. But Sir is laughing, and Meg is hiding her face, and Benny’s nearly in hysterics.

“Thank you all for punishing Dean.” Sir’s voice is strangled, but his hands when he unties the leash and helps Dean off the bench are strong and sure. He walks Dean over to them again, and Dean knows he’s a mess of tears, but he can look them in the face now.

“Are you satisfied?” Sir asks them, and they all murmur agreement.

“Took it like a soldier,” Benny says firmly, with a nod, and Dean gives him a watery smile.

“Then this public discipline is complete, and the slate is clean. No further repercussions or consequences, in deed or word, will be permitted from this time forward. Good boy, Dean, I am proud of you.” He smiles at Dean, and Dean takes a deep, shuddery breath, letting everything go, light as a feather, smiling back.  Sir wipes his face with a soft cloth and pulls him close, stroking his back, telling him again how good he is, how strong, how proud Dean has made him, and Dean fills up on the words until he feels full of warmth, like he's standing in the sun.  By the time Sir pulls back, his tears are long gone.

“One more thing, before you disperse,” Sir gets the attention of the others in the room again. “Dean is on leash discipline for the week. You all know the drill. He will be tethered if not held, and must ask politely to be moved. For restroom use, you may use the clips in each bathroom if you choose, but the door must remain open at all times. Of course anyone who does not wish to participate may call Benny, Meg, Ash, Cole, or myself to assist Dean at any time.”

What? Dean stares at him. He hadn’t even thought about the bathroom. He’s going to have to ask to go to the can? Like a toddler? A throb of pain from his butt keeps his protest behind his teeth, but he’s pretty sure Sir knows it was there, the way he gives Dean a little slap on the hip before handing his leash to Meg.

“It’s your free time,” he says calmly, in response to Dean’s questioning look. “Meg is your chaperone this evening. I will see you at bedtime. Be a good boy, Dean.”

Meg grins at him.

Oh shit. And he really has to pee.

Chapter Text

Meg wants to know how Dean found his pack. Benny wants to know how Dean got through the locked storage room door and then the secured locker to get to the thing. Both of them, and Cole and Ash, too, want to know where he got the knives. They’re all actually really cool, even if Ash is kind of a ditz and he has super-weird hair. For a while, it’s like Dean’s just shooting the shit with friends, though he has a little moment when he realizes that some of Sir’s staff actually double as a security team. Why the hell does a private training home need security?

But eventually, he absolutely has to ask.

“Gotta take a leak,” he tries muttering to Meg, who’s standing beside him, the end of his leash wrapped around her hand.

“I’m sorry, what was that?” She heard him just fine, he knows it, but the way her hip is cocked and her level, no-nonsense stare gives him pause.

“Uh. I need to use the bathroom.”

“I believe your Sir specified politeness.” There’s a definite frost to her voice that wasn’t there before.

“Please may I use the bathroom?” He would argue, but he’s already crossing his legs where he stands.

“Of course.” She leads him with a short-held leash to the large hall bathroom, and steps in with him.

“Sir said you could wait outside!” He’s almost in tears, he has to go so bad.

“If we want to. I don’t. Go, or don’t go, I don’t care. It’s nothing I haven’t seen before.” She leans close to the mirror over the sink and checks her eyeliner, and the fact that she’s not looking right at him allows him to let go and pee for what feels like hours.

He sags with relief when he’s finally done, and she moves aside easily enough to let him wash his hands. He can’t meet her eyes, and when he looks at himself in the mirror, his cheeks are red.

“One more thing,” she says firmly, and pulls a drawstring bag out of her pocket. The metal cock cage spills out when she tips it open onto the sink counter. Dean bites his lip hard to keep the words inside, but his whole body tenses up in denial.

“I know it’s hard,” she offers, all of the frost gone, now. She’s actually smiling at him a little in the mirror when he checks. “We’re all pulling for you. We’re here to help, Dr. Novak lets us know exactly what to do when we’re chaperoning like this, and you aren’t the first Sub we’ve done this for. Don’t worry, it’s part of our job, we know what we’re doing.” She puts a hand on his shoulder, pats him gently. He can’t help it, he relaxes just a fraction, though he has to close his eyes and turn his face away when he sees she’s pulling out some wet-wipes.

Her hands on his penis--now Sir has him using the weird medical terms, God--are gentle and kinda clinical. She wipes him down, quick but thorough, and then works the ring on over his penis and sac. The sharp yank of a pubic hair makes him jump and stare down at her, in her jeans and sweater and boots. He feels naked, suddenly, like he hasn’t in days.

“Shit, sorry. Good thing the waxer’s coming Wednesday.” She snaps the cage on, and tests the fit.

“I hate being the only naked person here,” he blurts out without meaning to. She glances up at him, neutrally.

“Why do you think you are?”

His lip curls.

“To keep the Sub in his place, of course. Just a sex toy. No privacy, no way to keep my stuff to myself.”

Meg straightens up, and starts to wash her hands. “It’s a good thing you’re so fucking pretty,” she finally says flatly, which snaps him to attention. What the hell? “Nobody here thinks that about you. Why would the whole house turn out to help find a sex toy? Or ask a sex toy to teach them to pick a combo lock. Dr. Novak is the best, and he has rules for damn good reasons. Subs don’t wear clothes in this house for a few of those reasons, and you should ask him what they are, but none of them are to make you feel bad. He’s not petty like that.”

He really can’t think of anything to say to that, so he follows her out of the bathroom in silence, the cage heavy between his thighs.

The others have gone off to do whatever they do by the time they return to the sitting room, and Meg lets him choose where he’ll go for free time. It’s really weird being the one leading, when she’s holding the leash.

He avoids the phone room. He misses Sammy like an amputated limb, but he won’t call home, not and risk talking to his dad right now. Does Dad even know that Sir isn’t planning to sign his papers back over, whenever the training is done?

When is the training gonna be done?

“So, Meg,” he starts, poking at one of the couches in the big sitting room, before deciding it’s safest to just kneel on it. Not so relaxing, but his butt will thank him.

“So, Winchester,” she answers, sitting next to him.

“How long am I here for? Ballpark.”

“I honestly have no idea. No, seriously,” she laughs at his raised, skeptical eyebrow. “We’ve had Submissives here for two weeks, and one was here for almost seven months. It’s pretty individual, I think. Dr. Novak says everyone’s different, so everyone moves at their own pace.” She shrugs a slim shoulder. “Most of us here on staff are Switches, a few of us are low-level Dominants, so we don’t have first hand experience with it, but some of the Subs that come here are in real bad shape. You’re not even close to the worst.”

“I like to think my shape isn’t so bad,” Dean mock-complains, flexing a bicep in a classic bodybuilder pose, and she rolls her eyes at him.

“And on that note, I’m going to tether you here and get some of the budgeting done. I’m here to chaperone, not endure bad pickup lines.” There’s a D-ring welded to the metal underframe of the coffee table, Dean sees as she clips his leash to it, spinning the lock secure. She pats the table. “Bolted to the floor. You can reach the remotes, there’s water in the cabinet, and I’ll be right through that door. Call me if you need the potty!”

Dean extends a meaningful finger in her direction, and she just laughs at him.

Leaves him alone.

He gives an experimental tug on the leash, and nothing moves. Suddenly urgent, he wraps both hands around the leather, plants both feet on the ground, and heaves back with all his strength. Nothing. His heart is starting to beat a little bit fast.

He grabs the remote and turns on the TV, and tries to get comfortable on the couch, half-kneeling to keep the weight off his ass. His free hand won’t stop tugging at the leash, though, testing it. The news is on, and he hates the news, so he flips the channel, and then again. Home Shopping. This house definitely needs a Roomba, Dean’s sure. Change again. A comedy special. Suddenly he’s back on his feet, yanking desperately at the leash, hauling at it wildly, blood pounding in his ears.

“Meg!” He’s shouting but he has no idea why, only that he’s gotta be able to move, he’s tied down to one spot, trapped, helpless, and that’s dangerous, that’s terrifying, anything could come through the doors, vampire demon wendigo shtriga--

“Hey, hey, okay, Dean, I’m here. It’s okay. It’s all right.” She’s right there next to him and as abruptly as it came, the panic floods back out of him. He staggers forward a step to take the pulling weight off his collar and that’s enough for her to release the lock, he’s free, and he’s rubbing his neck with a shaking hand, looking at the floor.

Even though she’s not Sir, when she touches him it feels okay. She’s settling him down, not on the couch, on one of the chairs, and she’s petting his hair like he likes. Her voice is pretty calming when she’s not being a bitch, Dean guesses. He manages a good deep breath.

“Good, that’s better,” she praises. “Not a big fan of the tethering, huh?”

Dean shrugs. He guesses not. He’s still staring at the floor. He’s such a pussy. This is basic shit, it was in the first few weeks of the training plan he got at the school.

“Listen, Winchester, everybody’s got their shit.” Her total lack of sympathy gets his eyes up, and she’s just looking at him like normal, no pity or disappointment. “Everybody. Don’t think you’re special. Now, you can come sit with me while I do the budgets, or we can just loop the leash on something here so you know you can get loose if there’s a problem. Your call.”

Budgets sound like hell.

“Uh. Can we try that second one, please?” He rubs his neck again.

“Sure. Here, see.” She holds up the leash handle, and hooks it over the wooden ball at the end of he couch arm. “Your neck okay? Let me look.” She leans in, pushes the collar up, and checks the skin underneath.

“Yeah, I think so. Just gave it a good yank.” He’s still embarrassed, but a little less so now. And the leash isn’t nearly as bad now that it’s only attached to the couch.

“Looks like you’ll probably survive. Okay. Take two. I’m going to be right by the door for a minute or two. You start feeling weird, you just say my name, no bullshit, capisce?”

“Capisce.” He even manages to pull out a grin for her.

She leaves again and his heart goes thump-THUMP, but it’s just an echo. He looks at where the leash rests quietly over the couch arm. It’s fine there.

Grabbing the remote, he hits the menu button. He’s pretty sure there’s a Dr. Sexy marathon scheduled for this week, and he’s got some catching up to do.

***

“So you literally fucked him into Submission! Hah!”

“Gabriel.”

“No way, Castiel, there is no way I’m letting this one go, this is way too awesome. You actually fucked the piss out of him! Holy shit, little bro!”

“Gabriel.”

“I mean, don’t get me wrong, if anyone could it’s you. Did he sing your praises in a hymn of rapture? I hear it’s better than an orgasm for the Sub. Kind of a built-in reward system for hitting subspace so hard. Is he kneeling in sweet surrender at your feet right now, gazing at you in adoration?”

“Hardly,” Castiel grumbles. “He was embarrassed by the whole thing. Then he had to take discipline from the staff, and now he’s on his free time.” He glances at the clock.

“Probably because he liked it too much,” Gabriel says knowingly. “That one’s gonna kick twice as hard against anything he feels like he shouldn’t want, if it feels extra-good. But hey, that’s your problem to solve, not mine.”

“It is,” Castiel says sternly.

“Seriously though, Cassie,” Gabriel’s voice softens and gets serious. “I’m really glad to hear you broke through with the punishments. Crying, the apologies...that must’ve been huge, and I know it’s a big step.”

“It was so hard not to comfort and soothe him before,” Castiel confesses, “but without any sign of remorse, I couldn’t. Thank the Holies that’s past.”

“And now you can cuddle him and wipe his tears away, you big softie,” Gabe teases him.

“I might have to start coming up with alternative punishments,” Castiel admits. “His bottom’s had about all it can take for a while, but I very much doubt he’ll behave until it heals.”

“Good,” Gabriel says, with an edge that surprises Castiel. “Make them good harsh ones.”

“What?”

“I know, punishment wipes the slate clean. But fuck, Cassie. If something had happened to him when he was out there, when he was your responsibility? You could’ve lost your training license. You definitely would have had to leave the board of the schools.”

“I know. We got him back!”

“Using your Grace! Castiel! You told me how far he got. If he was contracted with any human trainer, he’d have been in the wind forever. He’s not a normal mis-oriented Submissive who needs the standard training regime. He’s a highly trained monster-murder machine with a long kill sheet who just happens to also be a messed-up Sub. Are you even dealing with that?”

Castiel rubs his eyes. “I’m teaching him Krav Maga?” he offers weakly.

Gabe starts laughing. It’s real laughter, not mocking, but still. “Oh my Grace. Oh, only you, Cassie. Yes, make him even more lethal, that’s a completely fantastic plan.”

“Listen, Gabriel, as much as I enjoy amusing you, there was actually a purpose to this call. You still plan to visit on Saturday, yes?”

“Yep, with the papers and plans for the new Dom Center, and some contracts for SubSub that need your signature. Wouldn’t miss getting me a good look at the new and improved Dean-o, either!”

“All right, good. If I can arrange it, would you be amenable to driving Sam Winchester here and then back with you? Dean has mentioned him multiple times, and is clearly missing him terribly. He isn’t ready to leave the home yet for any length of time, but I believe seeing his brother would be very beneficial to him.”

“Gabe’s Taxi? Oh, fine, sure. Whatever. If the kid makes a mess in my car you’re paying the cleaning bill.”

“He’s fourteen, not four.”

“Still. Just let me know, I can do it.”

“Thank you, Gabriel.”

“You got it, bro.”

Chapter Text

Meg leads a yawning, heavy-eyed Dean through the bedroom door at 10:30 sharp, and Castiel smiles at her from his small writing desk.

“Thank you, Meg. Was he a good boy?”

“He was,” she confirms. She loops his leash over the doorknob, though, leaving him there, yawning again and shifting from foot to foot, and steps close to him.

“The locked tether induced an almost immediate panic attack,” she reports quietly. He searches her eyes and finds all well. “I calmed him, and just hung the leash on a dowel. As long as it’s not locked he’s fine. And if someone is there with him, the lock is acceptable, it seems.”

“Well done. Thank you. Please inform the staff of the change in the leash protocol for Dean.” She nods, satisfied. “Anything else?”

“Two bathroom trips, wet only.” Off his frown, she tips her head. “Benny still performs enemas on the Switch staff before and after heavy anal submission sessions, and whenever they need it. It isn’t sexual for him, as you know, but it is a Dominant practice for him, and he makes it very easy and good, if you don’t want to get into it with Dean yourself right now.”

He huffs a little laugh. “I wouldn’t mind, but I expect Dean would, knowing him as I am beginning to. Thank you, Meg. I will speak to Benny tomorrow and we will work out a daily time for Dean to go to him.. You are, as always, my right-hand woman.” He squeezes her hand and she beams at him, and leaves with a little wave at Dean.

“Long day, sweetheart.” He stands and walks to Dean, who blinks at him with a tired smile.

“Yessir. I like your bathrobe.” He reaches out and runs his hand down Castiel’s chest, petting the silk dressing gown, initiating touch for the first time. His palms reach Castiel’s waist and he steps forward, wordlessly asking for an embrace, and Castiel unties his robe before pulling him in. Skin to skin is best. Dean nuzzles into his shoulder, and Castiel hums to him, wordless comfort.

“All right, gorgeous boy. Do you need the bathroom before bed? Brush your teeth, anyway,” he encourages gently, after a long moment, and holds Dean’s leash to allow him to brush his teeth and splash water on his face. It seems to wake the boy up, and the nervous little looks he’s shooting Castiel’s half-hard cock have all his sadistic impulses sitting up and taking notice.

Not tonight, he tells them sternly.

“On the bed on your side, Dean. Bring your top knee up to your chest. Get comfy, you’ll be stretched well tonight before I take you.”

Dean moves towards the bed hesitantly, looking confused, and a hand plucks at the cock cage. Castiel smiles as he fetches the little hand-pumped stretcher from a drawer, his lube, and the book he’d been reading. “No, Dean, that stays on tonight. You’ve had your orgasm today, and I already know this will feel very good. It’s the whole point.”

“If you say so,” Dean grumbles, and arranges himself with his back to Castiel. “Why are you doing this? Sir?”

“As satisfying as our sex has been to me and for our dynamic...” Castiel sheds his dressing gown and joins Dean on the bed, and soothes a hand over his hip, pushing up his cheek to expose his hole. He coats the slim, deflated stretcher in lube and presses the tip to the little tight pucker, and eases it inside, holding Dean’s hip against the shudder. “Good boy, relax...I don’t want to set it in your mind that anal penetration is painful by default. Your body is still learning and adopting new ways to react to submissive acts, and as your trainer, it is my responsibility to ensure you experience the spectrum. Fearing rough penetration at any approach would be crippling, if your partner were to want you to anticipate and enjoy it.”

“Maybe I’ll just find a lady Dominant, ahhh,” Dean grunts, as Castiel inflates the stretcher one pump. The flared base keeps it seated snugly in his hole, and it will stretch him without stress.

“Almost all Dominants will penetrate you, lovely. With fingers, a dildo, a fist--” Dean’s whole body shivers, interesting-- “the heel of her boot. Many female Dominants will be able to fuck you with their clitoral pseudo-phallus, as well. So gendering your choice won’t change anything.” He inflates the stretcher again, and watches as Dean’s hips twitch.

“Wouldn’t it be faster to just use your fingers?” Dean’s voice is getting plaintive. The stretcher has a bulge that will make itself felt against his Angel gland and his prostate at is inflates. That chastity cage must be feeling very tight. Castiel smiles to himself, and opens his book.

“It’s not something I particularly enjoy. Take deep breaths, concentrate on relaxing. Next time I will have you do this to yourself. One pump every minute allows the body to adjust properly.”

“Mmmmm,” Dean squirms as he squeezes the hand pump again.

Ten minutes later and Castiel has abandoned his book. Dean is moaning pornographically into his pillow, hips rocking helplessly to rub the greatly-inflated stretcher against his insides. Castiel reaches around him and thumbs the smooth metal head of the chastity cage; there is liquid pearling there, fluid forced from Dean’s soft cock by the pressure on his prostate.

“Please, sir.” Dean’s voice is hoarse. “Please, too much, too much…”

“Hush, baby, okay. Okay. Let’s get this out of you. Take a deep breath, Dean.” Castiel unscrews the air release on the stretcher, letting it out quickly and steadily, and pulls it free, leaving Dean’s hole stretched wide. With a quick hand, he slicks his cock with lube.

“Ohmygod,” Dean whimpers, a thread of sound. His pupils are huge, black, he’s almost down, and Castiel rolls him to his belly, blankets him with his body, and pushes his cock home.

There’s no tight clench of resistance this time, no sound of pain from Dean, no tears, just a moan that breaks in half like a sob. Castiel pulls back, slow, and thrusts back in harder, knowing how close the Sub is to the edge of overstimulation, too much pleasure, and sets a quick, hard pace, hips pistoning.

“Sir!” Dean cries out, and then he’s squirming hard, and Castiel raises his upper body up on his arms, arching his back so he can dig his cock up and in and deeper, grind the thick root of it hard against every sensitive nerve and gland near the rim of his Sub’s hole, over and over, rutting in hard, merciless.

Goosebumps break out on every inch of Dean’s skin as he shakes. He’s moaning, a constant stream of wordless sound, and he seems to be trying to escape into the mattress and shove up for more of Castiel’s cock at the same time. His distress is sublimely gorgeous, and coils the knot of desire into a sudden, urgent need at the base of Castiel’s cock. One, two, three, four more quick hard fucks in and Castiel comes, fingers digging hard into the bed on either side of Dean, holding himself deep and solid inside as he shoots over and over.

When he pulls out, he slides down between Dean’s thighs immediately, spreading those round, deliciously bruised cheeks so he can see. Instead of red and angry, Dean’s hole is still stretched, loose, a hint of the soft pink inner muscle showing through. A slick white trickle of his own come is oozing out, and he pushes it gently back in with a finger.

One of Dean’s hands searches back around his hip, and he guides the fingers to his hole. Watches him pet and touch himself hesitantly, fingertips fluttering gently, shakily, where he’s wet and stretched.

“Feel that, baby? So soft and pretty. And my come is making your lips all shiny, honey, it’s beautiful. You’re such a good boy, Dean.”

“Feels so strange,” Dean murmurs. “Empty.”

He eases back up the bed, and gently urges Dean to his side so he can slide in behind him, wrap around him more easily. He reaches up and snaps Dean’s leash into place in the headboard, and then holds him.

“See, it doesn’t have to hurt.”

“It...it felt okay.” Dean’s voice is clear, if shaky; he’d obviously never reached subspace, too caught up in frustrated arousal and overstimulation, Castiel thinks. Too much in his own head.

“Just okay?” He feels around the cage, and it’s wet with precome; Dean had been gushing at some point, the frustration must have been intense.

“How come...how come when it hurts it feels so good after, and when it feels so good, it hurts so bad?” Dean’s voice is small, hesitant, and Castiel pulls his Sub’s hands up away from the cage, where they’d been starting to drift, and folds them inside his own.

“Sweetheart,” he puts a touch of dominance into his voice. “We talked about this, a little. When we are in bed together like this, whose orgasm am I interested in?”

“Yours, sir.” Dean’s voice is a little stronger, and he snuggles back closer.

“That’s right. And watching you beg, and squirm, and leak everywhere, and shake, was gorgeous. It was so hot and perfect, Dean, it made me come more quickly than I had intended to. So what’s the answer to your question?”

“Because it pleases you,” Dean says confidently, after a little pause, and it almost sounds like he’s smiling.

“That’s exactly correct, and you are submitting yourself to that. How does that make you feel? You can be honest, no matter what.”

“Really good.” Dean sounds surprised by his own answer. “Relaxed? Calm. Really...relieved, somehow? I don’t know.”

“So good, what a wonderful Submissive you are,” Castiel praises him, kissing his shoulders, his neck. “I’m so proud of you. You are incredible. Now sleep, amazing boy. We have a lot to do tomorrow.”

Dean hums, and his head ducks submissively. Castiel’s dominant instincts purr.

Chapter Text

The next few days are a whirlwind for Dean. Mindful of Gabriel’s words, Castiel tries to keep him just the smallest bit off-balance, introducing new things at intervals, making sure he’s always challenged and engaged.

Dean takes to Krav Maga like a duck to water. He clearly revels in being permitted loose-fitting workout gear, and tumbles and punches and ducks and throws with Castiel and Benny and Cole and Meg and Claudia as if he’s always been there. And he’s lit up like a candle for hours after, cheerfully learning the two new positions Castiel wishes him to practice--Supplicant, which he may use for requests, prostrate on his knees with hands extended on the floor above his head and wrists gently crossed, and Endure, a punishment position, an open-kneed squat with his fingers laced behind his back.

Surprisingly, he does not object to the nightly enema at all. They are familiar to him from a nanny and childhood illness, he says, and while he avoids meeting Castiel’s eyes while discussing them, he is happy enough to agree to spending an hour with Benny at the end of his free time each evening. And the first one leaves him sloe-eyed and relaxed, loose-limbed and flushed, so pretty that Castiel finds himself speechless.

In contrast, it takes half an hour, wrist and ankle restraints, and four with the switch across his shoulders to get him settled for the body waxer on Wednesday, and even then, he’s sullen and glaring.

“I could have whipped your thighs and then had you waxed there,” Castiel tells him, as they wait for Ash to be done with his turn in the salon room. He is near the end of his patience with the boy. “Be grateful I did not.”

“I’m not grateful you’re yanking all my body hair out by the roots at all. Sir,” Dean drawls without looking at him. He rattles his wrist chains.

“If you can show me where in the contract it states an exception for waxing when it comes to my responsibility for decisions concerning the training of your body and your Submission, I will happily cancel your time,” Castiel growls at him, and then it’s Dean’s turn.

It takes two hours to get Dean waxed bare from the chin down, and then rubbed with the growth-inhibiting cream that will keep him hairless for the next twelve to sixteen months. Castiel promises to double the waxer’s fee, and buzzes for Meg.

“I have never in my life handled a Submissive when in an unbalanced temper, and I will not begin now,” he tells her tightly. “As the most Dominant member of the household after myself, may I entrust him to you?” When she nods, wide-eyed, he shoves Dean’s leash into her hands. “Please return him to our room at bedtime.” Dean, pink and seething, is left in his wake as he heads to the gym, but he hears him snarl “I look like a goddamn hard boiled egg!” to Meg as he goes.

Dean takes ten with the strap and twenty with the switch that night, and sleeps at the foot of the bed tied to a bedpost, and it is a very, very sore and remorseful Submissive who spends every spare moment Thursday painstakingly cleaning every fragment of spilled, hardened wax out of the carpet of the waxing and massage room.

Castiel uses the time to meditate, re-center himself, do some reading, and call John Winchester.

It goes more smoothly than he expected. The man sounds tired, a little sad, and for all that Castiel hurts for Dean and all the things that are so hard for him because of his history, he knows his father loves him. And the man is a hero, after all. He changed the world, the future. Everything.

He assures John that all is well with Dean, that he is healthy and safe, that his training is progressing.

“That’s good news, because Dean, he’s a stubborn little cuss,” John says, and Castiel has to nod. Truer words. “And he and I, well, we had words the last time we spoke, didn’t end it well. It’s good to hear he’s getting along okay.”

“He is, yes. Better than okay, he’s thriving. But he misses his family, of course. Which is why I called, Mr. Winchester.”

“John, please.”

“John, then. My brother Gabriel, who manages Sublime Submission, will be visiting on Saturday. He’s driving up around eight am, and home after dinner. We were hoping Sam might travel with him, and spend the day with Dean, here with us.” He nearly holds his breath.

“I won’t tell you he hasn’t been bothering me six ways to Sunday about Dean,” John starts slowly, like he’s thinking it over. “But Sam is only fourteen. I’m not sure I like sending him off somewhere I’m not familiar with, and with a stranger.”

“Normally, I wouldn’t hesitate to invite you as well, of course. But Dean and I are still settling into our dynamic, and having a former Dominant in the mix, even if you are family, could be confusing for him right now. He’s been putting in an extraordinary effort, and seeing his brother would be a real gift.”

“Probably not so much for you, though,” John says dryly.

“I beg your pardon?”

“Oh, just that Dean’s not the only stubborn little Winchester cuss. I suppose I’ll allow it. I already know Sam will jump at the chance. I’ll need the full name of your brother, and the make, model, and plate of his car. And Sam will have regular phone check-ins. Those are my terms.”

“Done,” Castiel agrees firmly. “I’ll send you an email with all the details. I appreciate it very much, John. This will mean a lot to Dean.”

“Oh, don’t thank me yet,” John says, still with that odd humor. “But y’all enjoy yourself Saturday. I’ll be in touch.”

Castiel alerts Gabriel, cleans up a few more items from his inbox, and then sits back, feeling accomplished and well pleased with the world.

Benny’s call is a surprise. He’d had no idea it was already so late.

“Hey boss. We’re trying to do Dean’s enema, just like usual, but he’s tense and all sortsa nervy tonight. Nothing bad, but if he can’t relax a little, it won’t help him much. I’d just let him skip, but he needs it tonight.”

“Should I come down?” Castiel thinks he is perhaps not Dean’s favorite person at the moment.

“I think so. He’s a good boy for me, but you’re the only one has his Submission.”

“Be right there.” Castiel hurries, and by the time he reaches the door across from the room where he usually takes Dean’s blood, he can hear their voices.

Benny has the room nice and warm, he notices as he walks in. All the sterilization gear is camouflaged, the toilet and bidet, small sitz bath and corner shower are in quiet, peaceful colors, and the towels under Dean’s hips look soft. Dean’s on his back on the low medical table, knees up and spread, and he’s rubbing his abdomen with a fretful hand. Benny, surgical gloves on, just looks to be rubbing his thumb across his hole gently, slick with lube. The enema bag on its stand beside the big man is still full.

“What’s all this, then, sweetheart,” Castiel asks gently as he moves to Dean’s side.

“Sir,” Dean says, eyes locking onto his, and the relief in his voice makes Castiel smile. “Can you help me?”

“Of course. Always, lovely. Just tell me what you need.” The fact that Dean is letting himself ask for help, for assistance with what he needs, oh, that is important.

Dean glances at Benny, a silent question.

“He’s bound up a bit, and keeps clenching tight,” Benny answers. “Won’t let the flow in because he’s so tense. Your cock wasn’t in him last night or this morning, he said?” Castiel nods. “That’s part of it, then. And he’s been in punishment all day, that’ll cause a lot of stress.”

“I ate a loaf of fresh bread with butter on it in the kitchen with Angelique last night in free time,” Dean confesses in a small voice. “It was right out of the oven.”

“Dean!” Castiel is grinning, though, and Benny chuckles.

“I was upset! It made me feel better!” Dean says indignantly, and then winces and presses his hand to his belly again.

“Let’s get this going, brother,” Benny says, gently but no-nonsense. “You know you’ll feel so much better after you’re done.”

“Can I do hands and knees, Benny?” Dean’s discomfort seems to be allowing him to let his submissive nature free rein; his voice is small and respectful, and he waits for Benny’s nod before he moves.

“Why don’t I sit with you, Dean,” Castiel offers. “Would that help?” He’s happy to just stand by if that’s what Dean needs.

“Yes, sir, please,” Dean answers, almost shy, and Benny nods his head at the end of the table against the wall.

“If you’d like to sit there, he can put his head in your lap. That’ll be nice, eh, Dean, cher? All right. Let’s get that cute little derriere up for me, knees on the towel, that’s right.” He moves the enema stand closer, and stands behind Dean, between his feet, the slim tubing in his hands. “Relax, brother. Take a few nice deep breaths for me.” He looks at Castiel. “The chastity looks real nice on him, Boss.”

“Keeps everything out of the way,” Castiel agrees.

Castiel gets himself situated. Cross-legged, comfortable enough with his back supported by the wall, he’s able to guide Dean’s arms and head onto his thighs. The boy sighs and shifts, getting comfortable, smiling up at Castiel gratefully before going still. Benny lifts the tubing a bit, twisting it slowly.

“nnnNNN!” Dean whines suddenly, and Castiel can see his buttocks clench hard.

“Dean,” Benny warns gently, and meets Castiel’s eyes.

“I want you to take a very deep breath, Dean,” Castiel tells him, touching his shoulders, running his hands up the arch of his back to the dimples by his tailbone, where he starts rubbing his thumbs in circles, gradually increasing the pressure. “Now let it out for me, slowly. Let all your tension out with the air. Slowly. Good boy, that’s so good.” He feels Dean obey. “Wonderful, Dean.”

Benny nods at him and gives a thumbs-up, watching the hose, and Dean nuzzles against his thigh, hiding his face. He gasps once, and Castiel presses his thumbs in to those dimples firmly, then slides his hands back down to Dean’s waist, his sides, around to his belly. He strokes him there, soothing, bending forward a little to reach.

“Let it in, honey. It’ll make you feel so good. All nice and clean, no more stomach pain. Good, Dean.” The praise and his tone of voice make Dean relax even more, and Castiel can feel the little shivers under his palm, spread low across Dean’s abdomen.

“All right, that’s good flow, so I’m going to open it up,” Benny says quietly. “This is just saline and electrolytes, Dean, nice and mild. You be good, now, you breathe deep and calm.” Dean nods against Castiel’s leg, and though he squirms a little, his body relaxes in increments, even as Castiel can feel his belly distend under his palm, little by little. Not much, as the enema isn’t a large one, but it’s having a noticeable effect.

Benny’s hands are working between Dean’s legs, Castiel can see. Massaging his Angel glands, ensuring deep internal muscle relaxation.

“Sirrrr,” Dean slurs at him, and Castiel looks down. The boy is gone, down in subspace just like that, and Castiel grins, and moves his free hand to Dean’s hair, gently petting him, getting a slit-eyed look of pure pleasure in return.

“That’s a first,” Benny comments, hands still busy. “He relaxes when he starts getting real full, but he never goes down. Must’ve needed it pretty bad.”

“You’re incredible at this, Benny,” Castiel tells him sincerely, and gets a proud smile in return.

“Helps to love your work. Thanks, Boss.”

They work quietly together to gentle Dean through a few small waves of cramping, to turn him to allow the warm water to work fully, and after thirty minutes, Castiel eases to his feet, standing beside the table where Dean is curled on his side, his hands cradling the little bulge in his belly, serene.

“I’m going to let Benny finish you up, and bathe you,” he says softly, leaning down to kiss Dean’s mouth; the boy is almost unbearably sweet like this. “He’ll take such good care of you. Then he’ll bring you up for bedtime, and I’ll be there.”

“Okay, sir,” Dean smiles up at him, artless and genuine, still hazy and drowsy with subspace.

“That’s my good boy. I’ll see you in a little while, sweetheart.” He kisses him again, and with a final nod to Benny, who nods back with a smile, he slips out the door.

Chapter Text

Benny is great, a good friend. He presses Dean’s knees up to his chest to help him finish on the toilet and his voice is all soft and kind, he massages Dean’s belly, and makes sure he’s all clean. Dean’s stomach feels much better, just like Benny and Sir promised, and Dean would feel perfect, amazing, except he wants to be with Sir.

“Almost there, little brother,” Benny tells him, and leads him through the bedroom door.

Sir is there, reading in bed, and gets up to meet them.

Dean’s need to be with him is so deep and strong it feels like pain. He wants to get on the floor for Sir, go into the Supplicant kneeling bow, beg to be allowed to serve. Wants to please him, be good for him, wants to give Sir anything he asks and more.

“How did it go?” Sir’s voice is amazing, like rough velvet, Dean thinks. Benny holds his leash out, hands it off. Sir is smiling at him, his amazing blue eyes all warm and twinkling, so Dean has to smile back, of course.

“He was perfect, boss.” Dean preens a little to hear it. “Not a fuss or fidget out of him, and I couldn’t find a single bad thing to say about his behavior if you asked me to. He’s still down pretty far in ‘space, but he confirmed he’s a lot more comfortable now.”

“Thank you, Benny. Excellent work. If you’d be interested in making this part of your duties in the house, with a commensurate raise in pay, I’d welcome the chance to talk to you about it. Much like Crowley, with massage. Or if you’d prefer to continue to do it at a personal level, that’s fine too, of course. Just let me know.”

Startled but obviously pleased, Benny nods. Dean waves from where he’s pressed against Sir’s side, trying to share his skin, and Benny gives him a wink in return, closing the door behind him.

“I’m very pleased you were good for Benny, Dean,” Sir praises him, and it feels like his voice is directly connected to everything that makes Dean feel good. “Now, are you ready for bedtime? I want you to fetch the lube and syringe from the top drawer, and then Present, baby.”

Even the lurch of terror in Dean’s chest feels muted, and much less important than the tide of eagerness and gratitude that sweeps over him. “Y-you’re going to--” he tries to remember the term Sir uses, “--use me tonight? Sir?”

“Yes, sweetheart.” Sir is still smiling at him, and then he kisses him! One of those amazing, gorgeous, sexy kisses. With quick hands, he takes Dean’s chastity cage off, too, and puts it aside. “Now move it, young man. This,” he presses his erection against Dean’s belly, and it feels huge and rigid, like hot steel, “does not appreciate being kept waiting.”

Soft and floating like he is, Dean feels like everything is right up on the surface. His eyes are welling up with tears and his lips are trembling, because pain is coming, and he doesn’t like that. It scares him, his butt is clenched tight and his cock and balls are drawn up soft and small against his body with how scared he is. But at the same time, he’s soaring in anticipation, because his Sir is going to find pleasure in his body, dominate him completely, own him, hurt him, allow him to serve. He can’t wait, his mouth is wet, terror and yearning existing side by side. And all in the hazy, sweet softness of subspace.

Shivering even though the room is warm, he gets up on the bed, the lube and syringe set by his knees, and moves into Present. He loves this position best. It makes him calm and peaceful, even more than he already is in subspace like this, and he breathes deep, only a little shaky.

“There’s my best good boy,” Sir murmurs, so close behind him. That huge, hot cock brushes against the crease of his thigh and he flinches, hard, and Sir chuckles, not the warm funny one, but the dark Dominant one. It makes Dean’s spine go gooey. Sir puts the lube in him, which is easy since he just had his enema, but it feels too-cold and squirmy all deep inside his bottom. And then Dean starts breathing hard, quick, because he knows what’s coming. He makes fists in the bedspread and feels Sir’s hands hard on his hips. The big, smooth head prodding at his hole, catching at his rim before it gets the right angle.

“You cry if you need to, baby,” Sir says, soft. “But you’re already so soft and relaxed, and I’m so proud of how good you’re being, how you’ve surrendered. You’re a wonderful Submissive for me, Dean.” He drives forward, cock coring into Dean, steady and unrelenting and root-deep in one merciless thrust, and even cushioned and floating as he is, Dean screams helplessly into the bed at the razorblade burn of it forcing his hole open cruelly, suddenly wide. He feels Sir’s cock jerk and harden even more fully inside him at the sound. The gut-deep hot, curling satisfaction of that is even more powerful than the agony, and as Sir pulls out with excruciating slowness, drawing another scream from him, he tilts his hips higher. Silently offering himself up.

Dean,” Sir moans his name, like music, and Dean sinks further into that perfect, blissful place. He’s never been here so long, but Sir makes it easy to stay when he handles Dean like this, when he hurts him so intimately, makes him wail and cry and shake. Every punishing stab of Sir’s cock wrings more sounds from him, his voice cracking, thick with tears, his body going completely lax and pliant, his mind drifting easily, soothed by the knowledge of his Sir’s satiation.

It goes on and on, longer than ever before. Sir tells him how good he is, how perfect he feels around Sir’s cock, how pleased Sir is with him, and Dean’s soul basks in it. Dean can feel his body stretching, easing, the pains becoming less sharp, if no less deep. By the time Sir comes, grinding into him, he feels empty of everything but Sir. Clean and purified, good, beautiful, whole.

“Your first night with me, you told me you could not do this,” Sir murmurs to him breathlessly, as he shifts them to their sides on the bed. He’s still sheathed deep inside Dean, and Dean is so sensitive he can feel the rippling pulses as he ejaculates a few final times. “But you are perfect, you are wonderful. Your body is a delight and your Submission makes my Dominance complete. That was so good, Dean. What a beautiful boy.”

Dean sniffles, still panting a little, face wet, body still curled over. Docile, he lets Sir move him, settle his head on a pillow, and though he’s finally surfacing from subspace, the words are still sweet like honey. Sir’s arms come around him from behind, an embrace, and Sir takes his soft cock and balls in one hand, squeezing them together.

“Ahhh,” Dean chokes, head going back against Sir’s shoulder at the sudden dull hurt.

“Shhh, baby. Easy,” Sir soothes. He kisses Dean’s shoulder, his neck, as his cock fills a little again where it rests inside Dean. “I’m going to stay inside you tonight, sweetheart. Keep myself warm inside your lovely body. Try to relax, sleep now.”

Dean feels pinned, held still by the cock in his ass as surely as he would be by restraints. His sore hole throbs, trying to contract around the intrusion. But he is so tired, and Sir is here, holding him, and they are connected, closer than skin, safer than safe. As he drifts off, he thinks he hears Sir tell him that he has a wonderful surprise for Dean in the morning.

Twice in the night, Dean rouses whining, trying to squirm away, and Sir gentles and holds him until he calms. He never fully wakes, but the heavy fullness between his cheeks, the weight of the cock inside him, is unusual and uncomfortable enough for him that a few tears fall until he can slide back into deep sleep again.

Sir firmly gripping his breast in one hand and his hip in the other startles him awake in the morning, just in time to feel the cock inside him drag out, then thrust hard back in. He gasps, shocked, but his body has truly stretched overnight; though he’s dry and sore, his muscles accept the hard, deep intrusion easily.

“Good morning, honey,” Sir says, mouth close to Dean’s ear. “What a perfect way to start the day. Just relax and take it, that’s right. Good boy, Dean.”

“I gotta pee, oh, OH,” Sir digs his fingers in hard to the soft flesh around Dean’s nipple, making him arch in protest.

“Control yourself until your Dominant is finished with you,” Sir orders him firmly. “Relax your hips, good, that’s so good,” and his hips piston more quickly, finding a steady rhythm, his hipbones slapping against Dean’s bottom.

The squirmy, uncomfortable feeling of repeated, hard pressure against his full bladder is distracting Dean. It feels funny, different, like an orgasm about to crest, but not quite. That same kind of tension and waiting fullness, low in his belly. Sir thrusts deep. Shocked, Dean feels his cock begin to plump, fill with blood, harden against his thigh. It feels good.

Sir hums against his shoulder, nips at his neck, and pinches Dean’s sore nipple, then pulls it firmly away from his body, dragging a moan from him.

“Look at that. Dean, sweetheart, I think we will look at some desperation play next week when we start exploring fetishes, I think you’ll like that very much.” Dean can hear Sir’s smile in his voice, and his face goes hot. The embarrassment makes it worse and better at the same time; his cock gets all the way hard, in a rush, and he wants to hide his face and maybe die, all at once.

“You’re not permitted to come, Dean,” Sir warns, and then braces him, slams into him hard, five or six times, and comes himself, a deep groan in his ear of pleasure and satisfaction that makes Dean’s toes curl.

As he relaxes, he pets Dean’s tense belly. And finally pulls out, drawing a panicked squeak from Dean. Without subspace, everything feels sharp-edged and immediate, and oh god, he’s really gotta go, right now. Even half-hard now he knows he can’t hold it, not much longer.

“Okay, quickly,” Sir says with humor, and unsnaps his leash from the bed frame. Dean bolts from the bed, towing Sir on his leash behind him, and practically runs for the toilet, uncaring that Sir is watching him, only focused on the blissful release as he finally reaches the facilities and aims and lets go.

“Ohhhh,” he leans his forehead against the wall. Bliss.

“Feels amazing, doesn’t it?” Sir sounds approving and strokes his back gently, and then uses the sink to get a drink of water and brush his teeth, giving Dean at least the illusion of privacy. Light-headed with the relief of pressure and tension and how good it felt to let go, Dean just nods silently. His cheeks are still hot with embarrassment and sneaky, shameful pleasure, and he can’t quite meet Sir’s eyes.

They have a pretty good morning routine set by now. Sir takes off Dean’s collar and leash so they can shower, and they both use the toilet, brush their teeth, and shave with just a few words exchanged. Then Sir puts him in Inspect on the bench in the room, and makes sure he’s in good shape for the day. Dean likes how it makes him feel small and cared for, especially when Sir has used him in the morning. And then they head out to breakfast, usually. Dean’s always enjoyed predictable routine, ever since traveling with Dad, when mornings were always the same, no matter where they were, and he could hold onto that. But today, after putting some soothing cream up inside his hole and praising him again, Sir sits him on the edge of the bed with a smile.

“Tomorrow’s Saturday, and I’ve got a surprise for you. I know how difficult this has been for you, and how hard you’ve been trying. Nothing proves it more to me than how good you were for me last night, and this morning: Dean, you were amazing.” Dean flushes, looks down at his bare knees, still a little red from cleaning carpet all day yesterday. He’s not sure about that, but it still sounds wonderful.

“I spoke to your father, and we’ve arranged for Sam to come visit for the day tomorrow. He’ll get here right after breakfast, and stay all the way through dinnertime.”

Sam. His Sam. Sam, who he’s never been apart from for more than a few hours, who he hasn’t seen in almost a week, now. He stares up at Sir, mouth hanging open. He...oh holy shit. He really is…

“Really?” He swallows hard. “Seriously, you’re not fucking with me?”

“Seriously, I am not fucking with you.” Sir is grinning at him. “Does this please you?”

“Please me? Oh my god. Sir! Holy shit. Oh my god. I gotta...what are we gonna...he’s gonna freak when he sees the pool! And the gym! Oh my god!” Dean bolts up to his feet. “I gotta tell Angelique he’s coming, he likes vegetables, ugh, who raised him I ask you--” he’s practically dancing, he’s so excited, pacing back and forth as far as he can within the length of his leash.

Sir laughs, catching him as he moves by.

“Dean, calm down! He won’t arrive until tomorrow, we have a whole day. I will end your leash discipline one day early so you can spend time with him without being tethered or held, all right?”

“Thank you, Sir!” Dean beams at him, he knows he probably looks ridiculous, but he can’t help himself. This is the best, the greatest thing. Sam is coming!

Chapter Text

Castiel brings Dean to the regular Friday afternoon staff meeting; though normally he would be excused, since they’ll be discussing Sam’s visit for the first part, he knows Dean will want to be a part of it. As they walk to the large sitting room, Castiel watches him with pride. He’s adjusted beautifully to the leash training. He roams a bit, but always stays within the length of the leash, never getting caught with a jerk and needing to catch up. And it seems to be automatic, now, as well. In just a few days, his boy has adjusted to this new skill.

The staff choruses hellos and Dean tags at his heels as he moves to his regular chair.

“Dean, Rest,” he snaps his fingers and points to the floor at his feet, and when Dean hesitates, he raises his eyebrows. Lower lip sticking out just a little, Dean sinks gracefully into position on the floor. “You will be silent,” Castiel informs him. “You’re not a member of the staff, so being here is a special privilege.” He may be here and listen, but he won’t be invited to participate.

“Yessir,” Dean sulks into the floor. It will do.

“All right, people,” Castiel calls them to attention. “I know we have purchasing and budget changes on the agenda, and a proposal for an additional hire, but first, we will have two visitors tomorrow. My brother Gabriel will be here for the day, and he’ll be bringing young Mr. Sam Winchester with him. Sam will be our guest until after dinner, when he will return home.”

“That’s awesome, Dean!” Meg is grinning. “Can’t wait to meet him!”

“Dean is very excited about his visit,” Castiel smiles back, “and I’m looking forward to meeting him him as well. However, he is a minor child, and as such, I wanted to be sure you are all mindful of his presence in the home for the day.” He looks around and meets all their eyes. “You are all professionals, and I have no doubt you conduct yourselves as such at all times, but I’d be remiss not to emphasize that there must be no sexual activity and only age-appropriate conversation with Sam present.”

“Hell yeah,” Dean’s voice is muffled by the carpet, and Castiel puts a warning hand on his back.

“Dean’s schedule will be altered slightly to accommodate Sam’s visit, as well. His leash discipline will end tonight, and Krav Maga is postponed to Sunday. Dean’s free time is moved up to after lunch, to provide him time to spend with Sam. That said, the household’s rules are all still in effect, and I will explain them to Sam if he has any questions or concerns. Please alert me if you observe any being broken.”

“Wait,” Dean says, after a moment of frozen silence.

“Any questions about the visit?” Castiel ignores Dean. Benny quirks a sideways, amused look at him.

“WAIT,” Dean insists.

“Dean, you will be silent, or you will be punished. We will speak after the meeting,” Castiel says, hard. “If there are no staff questions, we’ll move on to the landscape-”

“Sir!” Dean’s head is up, out of his Rest position, his jaw is set stubbornly, and Castiel sighs and gets to his feet, Dean’s leash in hand. Meg puts her face in her hands, and her shoulders are shaking a little.

“Dean, Up.” He pulls a startled Dean to his feet and looks at the staff. “Excuse us for just a moment, please.” He tows Dean to the doorway, where the switch is in its stand, and grabs it.

“No, sir, no, no, wait, just wait, let me explain--” Dean struggles and squirms as Castiel gets him bent down over one of the padded benches flanking the door.

“If someone is not bleeding from an injury or in some other danger, your rudeness and disrespect to me and the rest of the staff is unacceptable,” Castiel tells him firmly. “You will have five with the switch for that rudeness and disrespect. Say yes, sir.”

“Noooo,” Dean wails, bucking, and Castiel puts a knee into his back to hold him still.

“Now it’s six. Say yes, sir.”

“Yessir,” it’s still defiant, but he says it, so Castiel lays into him with the switch without further delay. One-two-three-four-five-six, rapidfire cracks down on that raised bottom, so fast Dean barely has time to react to the first before the next is hitting. He’s shrieking apologies and kicking by the fourth and sobbing wildly by the sixth, and Castiel releases him gently after that last one, knowing the switch has done its work.

“Sorry, s-sorry, d-didn’t mean it, sorry Sir,” he cries into the bench, and Castiel raises him up, holds him close and soothes him quietly for a few long moments.

“Feel better now? More like my good Submissive with polite manners?” he asks when the tears have slowed, and Dean nods into his neck. “All right. I’m going to tether you here by the door, baby. I want you in Rest, right here, while we finish our meeting. We will talk right after, but I want you to think about how to ask your questions respectfully while you wait. Will you do that?”

“Yessir,” Dean murmurs. He slips down into Rest, his leash hung on the bench’s post. Castiel has positioned him so the six hot, bright-red stripes on his cheeks are displayed to the room.

“Dean apologizes for the interruption,” he says to the group, all of whom are clearly in various stages of amused sympathy as he rejoins them. “Now, where were we…”

Dean’s eyes are still a little red when Castiel fetches him half an hour later, when the meeting breaks up. He doesn’t move stiffly when Castiel has him stand, and Castiel gives him an encouraging smile.

“Now, we can sit and talk here, or we can go somewhere you’re more comfortable,” he offers, looping his arm around Dean and giving him a brief hug.

“Here’s okay, Sir,” Dean mutters, though he glances warily at the switch.

“All right. That spot in the sun looks nice. Let’s go get settled. We can be informal, but I still expect manners, Dean.”

Dean nods as they sit on one of the well-padded couches, drenched in light from the wall of windows.

“Okay. You have my full attention. What was so important?” Castiel is half-turned so he can see Dean’s face.

“Look,” Dean starts, and then stops. He huffs a breath out through his lips and rubs the back of his neck with one hand. “Look,” he starts again. “Sam’s my baby brother. Okay?”

“I know that, Dean. I know you two are very close, and that you practically raised him for years. It’s why I knew it was so important that you get to see him.”

Dean sends him a quick grin.

“Yeah, definitely. But look. I mean, the rules, the house rules? I can’t. I can’t be, like, a Sub, when Sam’s here, okay? I gotta wear clothes and stuff. Like a normal person.”

Castiel’s heart breaks a little, right then and there. He reaches out and takes Dean’s restless hand, tugs, pulls Dean close to his side so he can wrap him up, get him close. Dean grumbles, but sinks against him.

“Dean Winchester, I want you to listen very carefully. You can be a Sub when your brother is here...you have to be, because it is who you are. Submissives are normal people. Just like Dominants and Switches. There’s nothing abnormal about you or your orientation or your needs. And if you’d been oriented correctly from the beginning, well, Sam would have been used to seeing you nude occasionally in the home, and more once you started having relationships with non-familial Dominants.”

He turns his head a little so he can see Dean’s face. He doesn’t look convinced.

“Subs don’t wear clothes in the house here for a lot of reasons. One is that many of the things I ask of you here are very difficult and stressful, and I need to be able to see you, to make sure you’re not in any distress.” He strokes his hand down Dean’s side. “Another is that it’s a very visible mark of your Submission, a way to remind you that it is necessary for you to behave in a certain way towards your Dominant, to keep you in a particular, healthy mindset; it sets you apart as different and special. And yet another is that this is Training. The ultimate goal is to prepare you to go out into the world and have good, fulfilling relationships, and to help you understand the realities of those relationships. Almost all Dominant partners prefer their subs naked indoors whenever practical and possible, with no barriers or restrictions to their appreciation and enjoyment of their bodies.”

Dean huffs again.

“Fine, you have reasons. But would it really hurt? It’s one day!”

“It would be a dishonest representation of your role, your life here, and how your life is likely to continue,” Castiel points out gently. “Do you wish to give Sam a warped view of what life as a Submissive is? Being naked does not mean being sexual, Dean. Nor does it mean being weak.”

“Sam will think so!” Dean bursts out. “He’s gonna think I’m some pussy fuck-toy now, just because I’m a hard Sub, and I gotta be naked all the time, and you make me kneel and pose like those Subs in porn-” he’s breathing hard, looking away, and they’re getting at the heart of something here, Castiel can tell. “He’s gonna hate me. He’s gonna fucking laugh.”

“He will not.” Castiel puts all his Dominance into that tone, and Dean snaps to attention despite himself. “You have done nothing but sing the praises of that boy’s intelligence. I know you’ve told me you don’t know any high-level Submissives personally, but do you really believe that Sam, who is so clever, and who you raised from a baby, would believe that about you?” He turns Dean to face him. “You are incredibly strong. You’ve overcome a condition that would have hospitalized most, and you are still healing, but almost no one would be able to tell. You allowed yourself to hand over control to me, Dean, when you were terrified and raging, and that is one of the bravest, most righteous acts I have ever seen. And Sam knows you better than I, he knows that about you.”

Dean’s green eyes search his desperately, like he’s seeking truth. Castiel hopes he can find it in his own gaze, because he has never been so sincere.

“But what if he doesn’t,” Dean finally asks, in a small voice. “Can I put on clothes, then?”

“No,” Castiel sighs. “But in that vanishingly unlikely event, I’ll be sure to set him straight. You have my word.”

Some of the rigid tension has left Dean’s shoulders, but he’s still not really relaxed. .

“Can I meet him outside, at least?”

“Of course. If you’d like, I can explain the house rules to him in the entryway, much as I did with you, though of course he will not need to strip.”

“Do I have to eat on the floor?”

“Yes, Dean.”

“But why!”

“Do you really want to know, or are you just objecting because you think Sam won’t like it?”

Dean pauses. “I really want to know,” he sounds vaguely surprised.

“Taking food from your Dominant’s hand is both intimate and primal. For the Dominant, it fulfills a deep need to care for and provide for the Submissive, to ensure their good health, and to give them sustenance, pleasure, and delicious things. For the Submissive, you allow the Dominant to place the food in your mouth with their fingers; you have surrendered control of this most basic function of life, and placed it in their care and keeping. It demonstrates deep trust and faith in them.”

“Oh,” Dean says, eyes a little wide.

“Yes,” Castiel agrees, and flicks his nose gently.

“Will I, um. Be punished, in front of Sam?”

“Will you deserve to be?” Castiel gives him a narrow-eyed look, and Dean flushes.

“Not on purpose!”

“Correction and discipline is a healthy and normal part of the Dominant/Submissive dynamic too, Dean. It’s not shameful, or wrong. So, yes, if you earn punishment while Sam is present, it will be delivered while Sam is present. Please do keep that in mind.”

“But-”

“That one is not open to negotiation. You know exactly why I correct you as I do, and I believe you even know that you need it, now. If you behave, it won’t be an issue at all, so it’s entirely within your control to make sure it never comes up.”

Dean scowls and shifts against him, undoubtedly feeling the burn of his most recent stripes. Castiel smiles into his hair.

“So you don’t think Subs are weak,” Dean asks, almost challenging him, after a moment.

“I think that once your numbers are stable and you’re more comfortable in your orientation, it will be very good for you to meet some high-level Submissives I know. Some are my very dear friends, some are my employees, some are both. One of the challenges with the more rare orientations, the higher levels on both sides, is that many people seem to base their understanding of them on pornographic films or lurid novels, at least partially due to unfamiliarity. My Submissive friends have different needs than my Dominant friends, but that does not make them lesser people. So to answer your question, no, I do not think Subs are weak, because I don’t think anyone is anything merely because of their designation.” He pats Dean’s stomach.

“I did watch a lot of porn there for a while,” Dean admits.

“Doesn’t surprise me at all,” Castiel says.

Chapter Text

It’s odd to see Dean in clothing, Castiel admits to himself. And Dean himself is fidgety where he stands at the foot of the stairs by the driveway, though it’s hard to tell if it’s the clothing or impatience. He’s practically hopping from foot to foot, rubbing his arms in the cool morning air, and he’s been out there for almost fifteen minutes. Castiel himself prefers a comfortable seat in the entryway.

When Gabriel’s green coupe turns into the drive, Dean practically vibrates. And when it stops and the door opens, and a long, lanky teenager with an unruly mop of hair unfolds himself from the passenger’s seat, he bolts.

“SAM-MAY!” he bellows, laughing, and the kid tosses his backpack aside and tries a dodge and hip-throw that absolutely fails, gets swept up around the middle by his older brother, and taken down to the grass in a perfect tackle.

Castiel is watching the tussle when Gabe makes it up the stairs and leans a shoulder against the wall by his chair.

“So, the Winchester boys.”

“It appears to be them, yes.”

“I can’t believe you just subjected me to two hours in the car with that one.”

Castiel looks at him. “Why?”

“Oh, I’ll let you find out on your own. It’s the least that I can do. Are you current on your legal journal reading? Findings of the Texas lower appellate court? Sociological studies out of Stanford University? If not, you’re about to be.” Gabe pats him on the shoulder, and it feels almost like sympathy. “I’m going to raid the kitchen. Have fun!”

Blinking with confusion at that, Castiel keeps watching the boys. They’re just sitting in the grass, now. Sam is saying something, waving his hands wildly, and Dean is laughing hard.

When they finally get up and brush off the grass and dirt, Sam digs a phone out of his backpack, and makes a quick call. Too far away to hear, Castiel can still see Dean’s quick shake of the head in response to something Sam asks, and then Sam puts the phone away again. They walk up the steps shoulder to shoulder, and if Dean’s steps are reluctant, Sam doesn’t seem to notice.

Castiel stands to meet them at the door, smiling.

“Sam? I’m Dr. Novak. Welcome, we’re so glad you’re here.” He extends his hand, and Sam takes it readily.

The boy is nearly as tall as Dean, but maybe half as wide, all arms and legs and huge hands, and if Castiel is any judge, he has a great deal more growing yet to do. Sam is going to be very, very tall.

“Hi Dr. Novak,” he says, polite if a bit stiff. “Thank you for having me.” Dean is making big pleading eyes behind him, which Castiel resolutely ignores.

“Dean asked me to explain our house rules to you as soon as you got here, so there’s no misunderstandings, and to spare him and you any confusion or embarrassment. Is that all right with you?”

“Sure,” Sam seems to take that in stride, and sits down with them in the little waiting area. Dean sits rather gingerly next to him.

“Dean’s also given me leave to talk a little bit about his medical status, so I’ll start with that,” Castiel continues, with a smile at Dean. “I remember meeting you at your home, and as I’m sure you know, Dean’s brain chemistry was very unbalanced at the time?”

“Adrenaline, Subutanol, Serotonin, Rewardarin, serotonin, and lactic acid,” Sam answers crisply, with a nod. “He was critical on three, and approaching that on the others.”

Castiel stares for a moment, then catches himself. Dean just fidgets with the hem of his t-shirt. “Yes. Exactly. He was also approximately fifteen pounds underweight, and both sleep-deprived and experiencing elevated heart rate and blood pressure. When we arrived here, Dean began intensive Submission training immediately, to bring those levels towards safety as rapidly as possible.”

As part of that, I have firm house rules which Dean obeys with no exceptions. While you’re here, I’ll ask you to respect his discipline and our dynamic, and also ask that if you have any concerns or questions, you bring them to me.” He holds Sam’s gaze, watches it narrow thoughtfully.

“You’re going to tell me the rules, right?”

“Of course.” Castiel relaxes a little. “Dean does not wear clothing in the house; he will strip here, and leave them in a cubby. This isn’t sexual, it’s a full-time visual and tangible reminder of his Submission.”

Sam doesn’t look upset by this, so Castiel continues.

“He addresses me as Sir, and with deference. He is expected to be respectful and polite to all members of the staff here, and to guests in our home. And most importantly, he is to be obedient, and submit himself to direction and commands when I give them. When these rules aren’t followed, he is punished.” Plain and simple, he leaves it at that.

Sam raises an eyebrow, and despite the fact that their features are different, he looks so like Dean for a moment that Castiel has to hide a smile.

“What, like a spanking?”

“I whip his bottom with a switch, on the spot,” Castiel says plainly.

Sam’s other eyebrow goes up, and Dean buries his face in his t-shirt, and groans.

“Oh my goood.”

“Good,” Sam finally says decisively.

“Sam!” Dean emerges from his shirt, and he looks so dramatically betrayed, Castiel can’t even hide his smile anymore.

“Oh come on, Dean. I know you were practically napping through Dad’s spankings the last couple of years. Mostly ‘cause he didn’t want to be giving them to you, but also ‘cause you got a tough butt.” He leans forward eagerly, eyes on his brother.

“I read this study that Johns Hopkins published last year, a really big five year study, where they were looking at couples with mild, moderate, and strict punishment protocols? And the mild protocol couples had really high levels of dysfunction across the board, even imbalances--”

“Saaaaam,” Dean groans again, interrupting him, and Castiel holds up his hands.

“I also read that study. It was excellent, and well-researched and thoroughly reviewed. But I think right now your brother would like to give you a tour of the house, and I need to go rescue my kitchen from my brother, and do some administrative work for the organization and the training centers. We’ll see each other in a few hours for lunch, though, 12:30 in the dining room.” He tips his head towards the door.

“Uh.” Dean goes red in the face. He’d seemed mostly accepting after their long discussion yesterday, but now in the moment, Castiel knows it’s hard.

“Here, Sam. Let me take your jacket.” Sam nods knowingly and stands, turning his back to Dean, taking his time shrugging out of it and handing it over. Then settling his backpack, making sure all the pockets are zipped. By the time they turn, Dean has stripped and is standing with visible bravado near the inside door.

“Dean,” Sam says quietly, and Castiel tries to look at him with eyes that haven’t seen him in a while.

He’s put on weight, erasing the hollows under his ribs and at his flanks. He’s still lean, narrow below his broad chest and shoulders, but time spent bare in the daylight has turned him golden all over, with freckles scattered here and there. The removal of his body hair highlights every sleek, healthy line of him, and without its thick nest of curls, his soft cock is almost discreet where it hangs quietly between his thighs. The small soft curves lifting his nipples just accentuate the muscle he’s been building everywhere else.

Castiel hears a sniffle next to him, and glances at Sam, startled. There are tears in his eyes.

“You look so good, Dean, I was so worried,” Sam says, choked, and Dean actually relaxes at that, and huffs a snort, and rolls his eyes.

“No chick flick moments, Sammy. Come on. We got a pool here, and all kinds of good stuff. I’ll show you.”

“Jerk,” Sam accuses, as he walks through the door at his side, bag on his shoulder.

“Bitch.” Dean knocks his shoulder into Sam’s. Castiel trails them, and closes the door, and goes to find Gabriel.

***

Halfway through their discussion of the new center they’re considering opening for high-risk Dominants, Cole knocks and sticks his head in the door.

“Sorry to interrupt,” he nods at Gabe and Castiel, “but I thought you should know Dean and his brother are going room to room and putting down salt lines on all the windows and exterior doors. You want I should tell them there’s already salt embedded in all the frames?”

Gabriel starts laughing, and Castiel pinches the bridge of his nose.

“Thank you, Cole, but no. I suppose it’s keeping them busy. Ah, please do stop them if they look like they’ll damage anything?”

“Sure thing, boss.” Cole withdraws as quickly as he came.

“So you still haven’t told him you know about all the things that go bump in the night?” Gabriel asks, once he’s settled down a little.

“It hasn’t really come up. And we’ve been very busy with other things.”

“Any more escape and/or murder attempts?” Gabriel looks very innocent when Castiel shoots him a hard look.

“No, none. But here. Look at this.” He digs in his desk and finds the chart of Dean’s daily tests, and hands it to Gabe. They’re about due a break from new-center budgeting anyway.

Gabe whistles, low, as he scans the numbers.

“I’ve kept notes on daily events and activities. As you can see, his numbers are all over the place. Thankfully he’s staying below critical on everything since the second day, but his rewardarin is low and adrenaline spikes are still incredibly high every day he doesn’t receive a severe punishment.” Castiel taps the day after Dean returned from his escape attempt, and then again the day after the waxing debacle; they are the only days where every number shows a distinct positive trend.

“So he responds positively to discipline. You knew that, right?” Gabriel says.

“Those are also the only two times he’s reached and maintained deep subspace,” Castiel tells him.

“Jesus.” Gabe sits back.

“It’s early days, yet,” Castiel continues. “His reactions and responses are still resetting themselves, and he’s still struggling with a lot of things that should eventually come easily and naturally. But both of those tests correspond to a severe whipping, which resulted in abject sobbing and remorse, followed by very painful anal submission to me.”

Gabe is clearly considering it seriously before he answers. “That’s really not all that harsh, for Training, for a Submissive with his issues who is fighting his orientation. Your switch has a bite, but it’s not going to do him any harm, and he’s not even limping, so I know you weren’t brutal with him. Just from what you’ve told me, it sounds like the pain allows him to give in. If he’s still subconsciously resisting his designation, when the hurt is powerful enough, it gives him an excuse to surrender completely. And without the surrender, his levels won’t change. Over time, and as his chemistry balances out, it should become easier.”

“That was my thought as well,” Castiel nods. “I wanted to hear your independent opinion, though, to confirm that my own...preferences...are not unduly influencing my conclusions. Thank you, Gabriel.”

“You’re so careful, Cassie,” Gabe says, affectionately. “You should know you’d never let that happen. Trust yourself a little.”

“I do,” Castiel smiles at him, “but I always check to be sure.”

“The thing is,” Gabriel looks at the numbers again, “he needs more subspace. Clearly. It’s healing, it’s healthy, it’s the biological pot of gold at the end of the submission rainbow. And I bet those good numbers are at least partially down to ‘space, not just the pain experience. Twice in a week is really low, even for a new Sub.”

“I can’t and won’t punish him without cause, especially not to that extent,” Castiel sighs. “But so far, it’s the only thing that works.”

“Well, that’s why you get the big bucks,” Gabe declares, tossing the chart aside. “I bet you’ll figure something out.”

***

Lunch starts awkwardly. Sam seems startled, and then unhappy, when Castiel orders Dean to his pillow beside his chair, and Dean slumps into his Wait position with poor grace. Even after they’ve started eating, it’s silent; Sam keeps straining to see Dean over the table. At least Dean is making what Castiel judges to be a sincere effort at good table manners.

“Sam,” Castiel finally lays down his knife, after making sure Dean has had a few bites. “Is something bothering you?”

Sam shrugs a little, finally looking like the fourteen year old he truly is. His sharp little face is displeased, though he’s eating heartily. “I don’t like it that Dean’s on the floor when the rest of us are at the table,” he finally says, after swallowing. “Doesn’t feel right.”

“Hand-feeding is important-” Gabriel starts, at the same time as Castiel says

“A Dominant feeding a Submissive--” and then they both stop.

Dean snorts quietly.

“I know it’s important,” Sam says impatiently, “but I’m only here for a day and eating together’s important for us too, you know? We’re family.”

Castiel thinks about that, and then drops his hand to Dean’s hair, smoothing it as he looks down at him.

“Dean, would you like to join us at the table for lunch?”

Dean grins, wide and delighted.

“Hell yes! Sir. Definitely, thanks!”

“All right, up you get. There’s another setting by you, Sam, can you hand it over? Thank you.” They get Dean set up, plate and cutlery, water glass and napkin, and Castiel puts the portion of food that’s for Dean on his own plate.

Sam’s grinning across the table at his brother, and Gabriel’s got his tolerant face on, but then Dean gets a good look at Gabe, and his nose wrinkles up.

“Trainer Novak,” he nods stiffly.

“Submissive,” Gabe nods back, and oh dear, Castiel thinks.

“You know each other?” Sam’s lively with interest, watching them.

“Trainer Novak kicked me out of training school, and beat my ass so I couldn’t sit down,” Dean answers immediately. “So yeah, kinda.”

“Submissive Winchester attacked one of our trainers and broke his nose,” Gabriel fires back, and Castiel steps in before it can escalate.

“That’s all in the past, now. Dean, Gabriel brought your tests to my attention so I could bring you here. And Gabe, Dean is coming to understand what was prompting the violence of his outbursts. It was unfortunate, but it’s done.” He gives Gabe a warning stare.

Sam’s snickering into his roast beef, though, and Dean doesn’t seem all that angry. He just bends to his food with evident delight.

“Did you see the whole house, Sam?”

Sam nods. “It’s beautiful, really nice. The pool is going to be amazing in summer, I can tell. I bet Dean loves the gym, too, and he told me about the Krav Maga class?” He’s full of approval at that one for some reason, to Castiel’s amusement. “It sounds really awesome, Dr. Novak. If I was Dean, I’d totally want to stay here.”

Dean chokes a little and sips his water hastily.

“You should be settling in your orientation soon, Sam. I know they test your age group in school pretty regularly. No matter what, you’re welcome in any of our training schools,” Gabriel interjects. “I think it’s actually in Dean’s contract, that his siblings can attend any of the schools free of charge.”

“It is,” Castiel confirms.

Sam gins, excited. “That’s awesome. I think that’s such a cool idea. Get everyone educated right, and then there won’t be so many people needing intense rehab training, right? And a lot more happy and fulfilled people in their relationships?” Castiel blinks at him. “I read your literature,” he explains.

“Oh my god, you nerd,” Dean mumbles around some french fries.

“Manners,” Castiel reproves gently. “And yes, that’s the idea, Sam. So far we’ve seen incredible results. We offer everything from intro classes for the newly-oriented young people, to couples instruction, to intensive six-month boot camps for older singles who are struggling in some way. And we’re looking to start a live-in center for Dominants who need something even a little more supervisory than that, to get them back on the right track. And our organization is a fantastic employment opportunity for Dominants and Submissives both, as we hire across the spectrum for all kinds of positions.”

“I love it,” Sam says fervently. “I mean, I know a lot of people learn at home, but plenty of kids don’t have a dynamic example in the house, you know? Or maybe it’s not a healthy example.”

“You have another convert, Cassie,” Gabe teases.

“If the school tests were more accurate,” Sam starts, and Dean sighs and waves his hand in the air.

“Mercy, mercy! Can you save the world another day, Sam? Cause we got a date with the pool table in the rec room, and Meg’s got winners. You’re gonna like her, she’s great.”

Castiel glances at the wall clock. “And you’re meeting Ash and Angelique in the training room soon, Gabe? If everyone’s done, Dean, you may be excused. Your free time extends to dinner. Have fun.” Dean grins thanks at him, and escapes with Sam, Gabe heads off, and Castiel breathes deep and congratulates himself on another minefield navigated.

***

The soft knock at his study door a few hours later brings his head up from his book. “Come in,” he calls, and isn’t entirely surprised to see Sam Winchester step through and close the door behind him. He wasn’t expecting him to be alone, though.

“Where is Dean?” It’s not an accusation, but he does need to know.

“He and Ash are playing Super Mario in the rec room. I told him I had some questions for you about orientation stuff.” Sam shrugs. “It’s not a lie.”

“Well, come in and sit down, then. Ask away, my ears are open.”

“Dr. Novak,” the boy takes a deep breath as he settles in the chair. He sets his backpack between his knees. “Sir. There are a few things I think you should know about Dean. And yeah, a few things I wanna ask, too.”

Castiel nods, encouragingly.

“My dad, well. He raised us military. Dean was always gonna follow in his footsteps, you know? Marines, Special Forces. It’s all he ever talked about, and he and Dad, it was their special thing. Dad was so excited about it, too, they had little practice training camps and Dad would tell him all about being in the Marines and running missions. After mom died, Dean took care of me, he raised me, mostly, but this was how he and Dad connected. And then he got his orientation, and all that stopped.” Sam takes a deep breath and rubs his palms on his thighs.

“Don’t get me wrong, my dad is great. He loves Dean like crazy, but he’s kind of old fashioned. And you know there aren’t many Subs in the military, and I don’t think they even let them into Special Forces. So right there, immediately, Dean hated it. And that’s kind of where it started. No matter what, people kept telling him he couldn’t do stuff he wanted to, because of being a Sub. Even a low-level Sub, which is what we thought he was.”

“And being Dean, I’m sure he took that well,” Castiel murmurs, hiding his internal wince. Oh, Dean.

“Right?” Sam breathes, relieved that it’s clear Castiel is listening, understanding. “Only, Dad stopped talking about the Marines, but he didn’t change anything else. We were still military, we still lived the drills and the guns and...there’s stuff I can’t really talk about…”

“I know he’s a Hunter,” Castiel interjects calmly, suddenly tired of the subterfuge. “I haven’t had time to discuss it with Dean yet, but I’m aware of the life.”

THAT startles Sam. He stares at Castiel, eyes wide, then going narrow and assessing. It strikes Castiel, suddenly, that this boy could be very unsettling. Those clever cat-eyes, the unusual maturity and self-possession, the self-control.

“Well, okay,” Sam says, breaking the silence. “That’s...strange, but okay, cool. I can’t get sidetracked. Dean got heavy lifting part of it, always. And I read an article, a couple of months ago, in the New York Times. It was one of those longform things, and it was about Submissives who grew up in conflict zones, or in military cultures, and how they’re different. Dean’s different,” Sam leans forward, suddenly urgent.

“Different how,” Castiel encourages him, curious as to whether it’s going where he thinks it is.

“He’s always going to need to fight. That adrenaline thing, that’s probably permanent now, at least a little bit. Growing up fighting monsters? He didn’t learn to kneel and obey, he learned to go for the throat and never hesitate, that’s who he is. He’s never gonna be a, a domesticated Submissive.”

Sam’s got his hands together, almost pleading.

“Sam. Sam. I know. I know that, I understand. I figured it out too. It’s okay.” He reaches out and puts his hand over Sam’s, and squeezes once.

“So you won’t try to break him, to make him the same?” Sam begs. “I know you probably can, you could. Please don’t.”

“I swear to you, Sam.” Castiel meets his eyes. “I will do what I need to to get your brother to accept his orientation and his needs, to help him understand himself and his place in a healthy dynamic. But I won’t try to change who is is, or make him someone he isn’t.”

“What about when he’s done with training?” Sam demands. “What about, who’s gonna understand that, get him?”

“He will find someone. And I won’t sign over his Responsibility papers until he does, and he’s sure that it’s someone who’s truly right for him in every way.”

Sam sucks in and releases a deep breath, and Castiel can almost see the moment when he realizes he has no choice but to trust him. He sits back, and shakes his shaggy head.

“I’m just real worried about him,” he says softly.

“I know. But listen. Your brother isn’t as unique as you think.” He smiles at Sam’s skepticism. “You think most Submissives are, what, ‘domesticated?’ If that was true, there wouldn’t be much need for a training school, would there? Young man, your brother has some special challenges, it’s true. And he has some lethal skills that aren’t really the norm. But he’s doing very well, and he’s making good progress.  He's not some kind of singular lost cause; once he settles and truly wraps his head around things, he'll improve even more quickly than he has already.”

“He does look really good,” Sam admits.

“And he’s not a zombie or a pod person?” Castiel prompts.

“Definitely not,” Sam grins at him. He stands up when Castiel does, and extends his hand. “Christo,” he murmurs, as they shake.

“Beg your pardon,” Castiel says politely, hiding his internal laughter.

“Just a little blessing, for dealing with Dean. Thanks Dr. Novak, I feel a lot better.” Sam grabs his backpack and lopes out of the room, leaving Castiel staring down at his palm, where there’s a tiny smear of salt and ash.

Chapter Text

By the time dinner is done--Dean joining them at the table again, happily--and he’s hugged Sammy goodbye, promising to call every other day, no matter what, and then waved goodbye as he and Gabriel head out for their drive home, Dean is completely exhausted and also feels like he might explode.

He rounds on Sir the moment they’re alone.

“Why didn’t you tell me you knew about hunters! Sir!”

Sir spreads his hands a little, a who-me gesture. “It never really came up. And we were fairly busy with other matters.”

“Who else knows! Does your brother? What about the other people here?”

“Yes, and yes, mostly. I designed and built the house myself. There’s salt embedded in the sills and lintels of all the doors and windows, and in the foundation, an unbreakable line. You’re very safe here, Dean.”

Dean tries to wrap his mind around that. He hasn’t had a lot of time to worry about the supernatural, honestly, since he got here. He’s got a basic kit in his bag, of course, but all his energy has been devoted to getting through each day, everything new and strange.

Honestly, a werewolf attack would feel kind of homey and familiar right now.

“What did Sam do when you told him?” Dean’s wildly curious and Sam wouldn’t say. Sir grins at him, with lots of teeth.

“He said ‘Christo’ and shook my hand with salt.”

“That’s my boy,” Dean says, proud. “Nobody’s gonna get the drop on him.”

“Probably not. You were right about his intelligence, too.” Sir’s admiration makes Dean feel just about as good as if he’d birthed Sammy himself, which might be kind of weird, but whatever.

“Yeah. Kid’s a genius, all right. He’s gonna change the world, you watch.”

“He’s almost as special as his big brother,” Sir goes on, which, what? Sir crooks a finger at him, and Dean goes to him, still all flustered. He feels fidgety and too-tired and a little like his skin is too tight, but it’s awesome when Sir puts his hands on his waist and reels him in so they’re touching all down the front, right there in the front hall.

“I’m incredibly proud of you, Dean,” Sir says. “You maintained the house rules beautifully, even with the distraction of your brother here. You were polite to my brother Gabriel despite your history. You were a credit to your training and this house and your family. I am sincerely and deeply impressed.” He leans in and kisses Dean, first soft and slow, gently, on the lips, and then harder, more passionately. His tongue licks Dean’s mouth open, and his hands are strong and firm on Dean’s hips, and Dean is melting, he knows it.

When Sir breaks the kiss, Dean is dazed and half-hard, swaying a little.

“My good boy,” Sir hums. “I think you earned an orgasm today.” He reaches down and casually palms Dean’s cock, toying with it a little. “It’s still early. Are you seeing Benny at your normal time?” Dean nods, leaning against him, a little lightheaded at the prospect of an orgasm and the feeling of touch on him. He’s smiling like an idiot, he knows it. “Okay, an hour before that, I want you to tell me a position and a place. The position can be anything, doesn’t have to be one of your Submissive positions, and the place can be anywhere in the house that isn’t our bedroom. Then we’ll go to that place and you will get in that position, and you can masturbate just how you like while I fuck you with the training dildlo.”

Dean swallows hard, his mind flooding wildly with possibilities. And just as suddenly as he started, Sir stops fondling his cock, with a last little pat. “No touching this, Dean,” he warns. “I’ve missed you today, so you will stay right by my side until it’s your enema time, are we clear? And you’re not to touch your cock at all.”

“Yessir,” Dean gulps. He keeps his hands well away, doesn’t even want the chance of an accident. And Sir missed him? Something warm and sweet kindles in him at that, and the too-tight feeling of his skin starts to ease, a little.

“I missed you too, sir,” he answers impulsively.

“Even though you were running around with Sam and salting my house?” Sir is laughing a little, but he’s also taking his hand and leading him towards his study. Dean kind of misses the leash in a weird way, for just a moment; he always knew where he was supposed to be when he was wearing it, and how to follow.

“Yeah, though in our defense we thought we were doing a good thing,” Dean argues. “But it was weird not seeing you all day. I’m kinda used to it, I guess.”

“It’s jarring to break routine,” Sir nods, guiding Dean into the cool, high-ceilinged room with shelves lining the walls, his study. Dean doesn’t spend much time here, so he looks around curiously. There are two comfortable big chairs, a padded bench against the wall--he can guess what that’s for--and a dark wooden desk with a chair and a computer and lots of nicknacks on it. The windows have sheer curtains on them, and the evening light is coming in.

“So, you gonna tell me how you found out about hunters? Have you ever been on a hunt? You ever ganked a supernatural?” Dean can’t quite resist asking the questions. Sir is stronger than he is, faster, and kicks his ass without apparent effort in Krav Maga training. He also tracked Dean somehow that Dean still doesn’t understand, so it’s all worrying around in Dean’s mind like a sore tooth.

“Perhaps another time,” Sir smiles at him. “Let’s get you back settled into a healthier headspace, for now. On the bench, Inspect.”

“Again?” Dean whines without thinking.

“Dean,” Sir raps out sternly, and Dean scoots to the bench quickly, gets on his back with his hands behind his back, legs spread. He hears Sir washing his hands at the little sink in the corner. His heart’s beating a little fast. He doesn’t feel as calm and quiet as he usually does when Sir inspects him in the morning, and it’s hard to force his thighs apart.

“I know Sam’s visit was exciting,” Sir says calmly. He has a long ruler in his hand as he walks to Dean’s side. He taps Dean’s far elbow with it, and Dean presses it down harder, opening his chest up properly. “You were very good, and it went very well, but I know how disruptive it was to your routine and your schedule. That loss of structure and security can be hard for a new Submissive to navigate. I want you to relax, and take deep breaths, down to your belly. Don’t think of anything but my hands on you.”

Dean nods tightly. He’ll try, though he thinks it’s kind of crazy that Sir imagines one little visit from Sam could wack him out like that.

“Mouth,” Sir commands, and Dean opens his mouth. Sir looks closely, presses his tongue down, rubs a finger over his bottom lip. “Close,” he says, and Dean does.

“Why don’t...you’ve never made me give you a blowjob,” Dean realizes, out loud, as Sir rubs his throat with careful fingers.

“Would you put your cock somewhere with teeth, without being absolutely certain there was no danger of a bite?” Sir answers dryly. He touches Dean’s right breast, then spreads his whole hand over it, rubbing gently and pressing down.

“I wouldn’t!” Dean protests. The funny, deep pull of heat he always feels when Sir plays with his tits feels stronger today somehow, and his voice is all thin.

“Three days ago, you were in full restraints for a simple waxing. I prefer to err on the side of caution,” Sir says. “Hmm.” He rubs harder, firmer bigger circles that move Dean’s whole breast under his hand, and Dean’s breath catches. It’s just on the edge of pain, now.

“You’re softening here beautifully, baby,” Sir praises him. “Much more sensitive and responsive. That’s very healthy and normal, good boy.” Ugh, Dean thinks. They jiggle a little now. Sir moves to the other breast, and repeats the touches, the palming, the massage. Dean knows it’s because of his Angel glands, but the way his muscles relax and ease, his shoulders just soften, arms give up their tension, it feels so delicious. He sighs, and his next deep breath feels way easier.

“Knees up,” Sir commands gently. Dean pulls them towards his chest. “Up all the way,” Sir says again, with a tap from the ruler, and Dean strains, gets them higher. “Good boy,” is his reward.

“This is nice and healthy,” Sir praises, fingers squeezing the head of his cock, then pressing down the shaft, prodding at the base, moving it back and forth, up and down. Dean grunts, the pleasure of touch on his erection is too much for words, right now. His eyes are closed so he can just feel.

Sir tugs gently on his sac next, testing, and Dean whines, his thighs tensing. “Shh, sweetheart,” Sir soothes him, and he tries to keep those deep breaths going. “You’re a young and healthy thing, aren’t you? All full and heavy here. When we move to longer-term chastity, we’ll have to have a regular milking schedule, won’t we?” Dean knows what prostate milking is, and he tosses his head in wordless protest at the idea. “Shh,” Sir quiets him. He is holding each testicle, fingers measuring them. “Good boy. All right. On your belly, Dean, hold yourself open please. Spread nice and wide for me.”

He’s missed Sir touching him, Dean realizes. All day he’s been in free time, mostly, hanging out with Sam or sitting at the table for meals. But as he rolls over and reaches back to hold his cheeks open wide, he startles at the knowledge that this is good, it’s making him feel good, so much better than he had before.

Sir rubs a thumb firmly down his taint and Dean gasps, and then he’s got a couple of fingers at Dean’s hole. It burns when he pushes them in and spreads them, but it’s a familiar, comforting hurt, somehow, and Dean feels his legs and the base of his spine ease even as his nose prickles in reaction.

“There’s my good boy. My good Submissive,” Sir praises him. “That’s better, isn’t it?” His fingers press deeper, spread wider, and Dean sucks in air. “Very nice, Dean. Nice and healthy here, and your anal gland should be back to normal size very soon. That’s wonderful.” The fingers slide free and Dean gasps with relief. Sir removes his hands, letting him relax, and then palms his cheeks, rubbing them, stroking up to his back and then down to his thighs. It feels heavenly. Dean smiles blissfully into the bench.

“All right, all done now. Come sit by me.” Sir helps him up and leads him to the desk. There’s a big square pillow next to the chair, and Sir puts him on it, on his knees. “Rest,” he commands, and Dean obediently curls into the position. “You have half an hour before I need your answer about your orgasm. I’ll let you know when,” he says with a smile.

“Yes Sir,” Dean answers, smiling back, before putting his head down. His too-tight skin feeling is all gone. He’s not jittery anymore. God, he feels so much better now. And with some of the stuff Sam said when he was here still fresh in his mind--how proud he is of Dean, how cool he thinks it is that Dean’s going through this intense kind of training and kicking butt at it, how he kinda hopes he’ll present Sub so he do some of the stuff Dean does--he can’t even muster up any worry about it.

He hears voices at one point, Sir talking to someone. Then again a few minutes later, but he’s resting, his face is in the nice soft pillow. It’s not his concern. A little while later, Sir touches his shoulder.

“All right, Dean. Slowly, please, up to Wait.”

Dean uncurls, blinking, easing up to his knees, sitting back on his heels, and settling his raised palms on his thighs. He feels like he’s had a nap. Sir’s looking at him expectantly.

“I want to sit on the couch in the sitting room,” he says, with a nod.

“The sitting room? May I ask why?”

“Well, I got punished in there,” Dean explains, “so I should get rewarded in there too, right? And I always used to jerk off sitting on the couch, I kinda miss that.” And the idea of someone maybe seeing him with Sir like that, it makes his belly get all hot and tight. Sir nods with a smile.

“Excellent reasoning. Claudia brought the training dildo and lube for us, so we don’t even have to detour. Come on then.” He helps Dean to his feet.

“Pick your spot,” he invites when they get to the sitting room. Dean heads for the biggest, softest couch. Flops down on it with a grin. It’s kind of strange to be scheduling a jerk-off session like this, planning it out, with an orgasm being a special treat at the end. Really strange. But he’s so eager that the strangeness is just an extra layer of hotness, kind of. Sir is chuckling at him, too, and pulling over a low footstool.

“Hips up,” he puts a towel under Dean. “Lube,” he explains, after Dean’s questioning look. “Don’t forget the dildo. Here, get your hips down right to the edge. Spread out and get comfortable, you can touch yourself a little.”

You don’t have to tell Dean twice. He pets the head of his cock with gentle fingers, the hot, hard sleekness of it nice in his hand. He lets his head fall back against the couch. Oh, that’s good. He squirms a little when Sir slicks up his hole with a finger, works some inside, but it’s a distant distraction.

The blunt, cool push of the dildo is a lot more than that, and his eyes fly back open and he stares down his body. Sir’s sitting down between his legs, and the training dildo is all wet with lube in his hand, and he’s gently twisting it into Dean.

“Ohhhhhh,” he moans, as it pops inside his hole. It doesn’t really hurt, but the stretch is intense. He strokes his cock, root to tip, letting that pleasure ease the intrusion. Sir presses it deeper, and it rubs on the sensitive places inside Dean, and his hips buck up.

“There we go,” Sir murmurs. “Okay, baby. You go ahead. I want you to remember to clench around the dildo, okay? Like we’ve been practicing. Make yourself feel good.”

Dean starts jerking himself for real. Long hard strokes down, gentle up, palming the head, it’s heaven, every nerve lighting up with pleasure. And the dildo working in and out of him, steady and deep, feels so good too, like his hips are melting inside. He clenches down and gasps, a heavy jolt of electric lust shooting straight up his cock, his lower back, through his pelvis. He does it again and again, timing it with his strokes.

“Little faster and deeper now, honey.” Sir’s voice sounds far away. The dildo fucks up hard into him and his hips lift with it, driving his cock into his hand perfectly, fuck, fuck, it’s so good. He’s moaning like a porn star and his thighs are shaking, he doesn’t want this to end so soon but his balls are hard and tight against his body, primed and ready. He slows his hand down, trying to make it last.

Sir is merciless though. The dildo is slicking in and out of him fast and hard, and Sir has it angled forward so it’s rubbing his sweet spots every time it moves. Dean lets go of his cock, he doesn’t want to come yet but it’s too much. He’s gotta slow it down somehow.

“Someone’s been a very good boy, I see,” Benny’s voice is behind Dean and he doesn’t care, can’t look, but someone is watching him, seeing him like this. Dean keens with the pleasure of it, hips up off the couch as his cock fucks the air.

“So very good,” Sir affirms. “He’s even making himself wait for his orgasm, making it last.” The dildo changes angle a fraction and grinds into him and Dean’s almost sobbing with the hot weight of tension between his hipbones, the fullness, the burning desire to come. His hand is back on his cock in an instant and flying up and down the length of it, whipping himself closer and closer until he clenches one last time on the dildo and that’s it. The pulses start in his ass and spread, deep as a heartbeat. His balls tighten and everything releases and he comes, pure pleasure, blanking his mind, nothing but how incredible it feels, all over his body. Like every inch of him is orgasming, as his cock shoots over and over, all over his belly. Everything but sensation is gone, the world is white noise.

He comes back to himself a little while later to voices, and a warm cloth cleaning him.

“I came to see if you’d like his enema done early,” that’s Benny, “since the schedule was all crazy today, and I could tell he was tired. But we’re just about on time now anyway.”

“Can you do a deeper cleanse tonight?” Sir’s voice, above him, and Dean blinks his eyes open. “I know tomorrow’s the staff day off, so of course he won’t have one then.”

“Sure thing, boss. Might be a little--” his voice fades out, he can hear them murmuring. Then Dean hears Sir again, telling Benny yes, of course, and then Sir’s face is right above him.

“There you are.” Sir smiles down at him. “I think Dean likes showing off a little bit, Benny, what do you think?”

“Oh, definitely. And it was a very pretty show, cher.”

Blushing furiously, Dean turns away, and Sir chuckles. “All right, it’s time to go with Benny. You be a good boy for him, and I’ll see you at bedtime. Dean, even though Benny isn’t your Dominant, when you’re having your sessions with him I want you to obey his commands like I’m right there giving them, do you understand?”

Dean nods, and then realizes he’s meant to go with Benny right now.

“But sir.” Dean sits up; he’s still hazy and loopy with orgasm, but something is bothering him. He came, but Sir didn’t. He’s feeling wonderful and satisfied, but Sir isn’t. That’s...that’s wrong. He grabs Sir’s wrist, anxious and almost feeling off-balance. “What about you? You didn’t come.”

“No, I didn’t.” Sir takes his hand and guides it to his crotch; his cock is obviously soft under Dean’s palm. “It’s okay, this was your reward, Dean. You earned this with your wonderful behavior today. I don’t need service now, I’m very pleased that you enjoyed your treat.”

Dean relaxes at that, something unsettled in him easing away. “Oh. Okay, that’s okay.” He stands up, knees only a little wobbly, and meets Benny’s smile. “I’m ready, Benny.”

“Come on then, sugar.”

Dean really loves his enemas. They feel so good, and make him all warm and relaxed and sleepy. Benny warns him that tonight’s going to be larger, though, and he will have to hold it longer. Dean’s pretty sure that will be okay, so he’s nice and relaxed, lying on his back on the table, as Benny pets the back of his thigh gently as he works the nozzle and hose into him.

“You’re still all slicked up from your special good time,” Benny teases him, and Dean grins at the ceiling. “Nice and relaxed too, that’s good, brother. I’m starting the water now, you breathe deep.” There’s a little burr of Dominance in Benny’s voice that has Dean breathing from his belly, slow, and then letting it out, as the first water flows into him. He can barely feel it, Benny always gets the temperature just right.

He fills up steadily. It’s strange-feeling and not totally comfortable, but it’s drugging in the pressure and warmth and heaviness in his belly. He moans a little as Benny starts rubbing his sweet spots. That feels so good, and he relaxes even more.

He’s full, but it’s not stopping.

“Benny?” He can hear the nervous waver in his own voice.

“Relax, cher. This one is big, remember? I’ll take good care of you.”

“I don’t think I can hold it,” he squirms a little. His belly is bigger, he can see it, the pressure is getting intense.

“Of course you can, brother. Just a little more.” Benny’s thumbs dig in firmly on either side of Dean’s cock and he groans, relaxing involuntarily, easing the pressure. “There, see? That’s real good, Dean. Now I want you to play with your nipples some. Let’s make sure your lil’ derriere remembers that this feels good.”

“I don’t like that, Benny,” Dean objects, the pressure building again. He tries to bring his knees together, but Benny’s elbow stops him.

“Dean, Dr. Novak told you to obey me like he was right here. I know it’s hard, but you do what I say right now,” he insists, firmly, and Dean growls but his hands reluctantly go to his chest.

Playing with his boobs is actually really distracting, a few minutes later when Benny tells him quietly that he’s all full, there’s no more. It’s still really uncomfortable, he feels stretched inside and so heavy, but the tingles of pleasure from pulling on his nipples are enough to keep his mind off it. And this time Benny puts a little plug in him, which feels strange, and Dean grumbles a little about it, but slowly the discomfort eases, and he relaxes.

Slowly, that heavy, sleepy, warm feeling comes back.

“You gotta trust us a little bit, brother,” Benny says, an affectionate, quiet scold, as Dean blinks at him from the sitz bath as he’s cleaning up after. “I wouldn’t give you more than you can take. Some of the folks here, they take half again as much for a deep cleanse.”

“Sorry, Benny,” Dean sighs. He’s so tired he almost can’t keep his eyes open, now.

“You’re learning, it’s all right. Okay, let’s get you upstairs and back to Dr. Novak, little man, ‘fore you fall asleep right here in my tub.”

Dean follows Benny back upstairs, and lets Sir take him, and roll him into bed. He’s asleep before he can even say goodnight.

Chapter Text

Sunday is usually a slow day, Dean knows from talking to the staff. Most everyone has the day off, and the Submissives have a low-protocol day, with lots of free time. But since Sam was here yesterday, Sir explains as he tests Dean’s blood before bringing him to breakfast, Sir and Dean will just have a normal day.

“I can cook, you know, Sir,” Dean offers tentatively, as they take in the cold cereal and pastries, fruit and granola and yogurt set out on the sideboard. Even the coffee is being kept warm in a metal carafe. It’s Angelique’s day off too.

“Can you? Well, if Angelique grants us kitchen privileges--she guards her territory fiercely--we’ll have to take advantage of that next week. For now, I don’t fancy feeding you cereal from the table, so make yourself a bowl and sit with me, and we’ll talk about the plan for today.”

Once they’ve taken the edge off their hunger, and both Sir and Dean have their second cups of coffee, Sir sits back and looks at him seriously.

“You’ve been here a week now, Dean. And I’m very, very impressed with your progress. We’re going to start looking at different fetishes and kinks today, to find out where your interests are, and give you exposure to them. If we find one that means a lot to you, we’ll incorporate it into your daily life and training here.”

Dean squirms a little. Those rooms off the training room have been teasing at him since Sir gave him the tour on his first day here.

“Yessir. What about the ones I don’t like at all?”

Sir shrugs. “We’ll still explore them a little. You never know when something that doesn’t appeal might suddenly become interesting with some practice, and some Dominants may have a wide appetite for different fetishes. But beyond that, your levels have been improving, slowly but steadily. Mostly.”

Dean stares at him. Mostly? He feels so much better! He doesn’t get that weird, stuffy-hot feeling of rage anymore when Sir dominates him, or touches him. He hasn’t tried to punch anyone in days.

“We think--I think--the reason some of your numbers are staying unbalanced is because you have only dropped into subspace twice since you’ve been here. Do you remember?”

“Uh, yes. Yes, sir.” Dean chews his lip, going hot and cold and shivery at the memories. Sir dominating him so roughly, the whippings that pushed him past the point of endurance, oh yes, he remembers.

“Most healthy Submissives reach at least a shallow state of subspace once a day, or at most, every other day, and deep Subspace three or four times a week. So we need to find a way to help you get there, without making a run for the Arizona border or trying to attack the best body waxer in Texas.” The humor in Sir’s voice brings Dean’s eyes up from the table; he’s smiling, and his eyes are twinkling. He’s not mad at all, and Dean grins tentatively back.

“I loved being in subspace. I’m not doing it on purpose,” he swears, and Sir holds up his hand.

“I never thought you were. And every Submissive finds 'space in their own way, and you will find yours. We just have to come up with a good way to convince your subconscious that it’s okay to let go and enjoy it. I have a few ideas, but I’d like you to think about it too, and come to me if you think of something that you believe would help.”

Dean nods eagerly. Just getting to have some input sounds freaking awesome. “What are your ideas?” He’s kind of wildly curious.

“You probably won’t like them,” Sir warns him gently. “Remember, they’re meant to push you past your resistance and into subspace.  The more you get there, the easier it is to return.  Eventually you should be able to enter subspace at will, but in the beginning it might be hard.”

“I still wanna know,” he insists stubbornly. He does. He deserves to know!

“All right. One is to allow you to fight before I use you. The idea is that if you struggle, it will kick those instincts into high gear.” Sir’s watching him closely, and he can probably see how Dean’s breath catches at that.

“What if I win?” Dean can’t help but ask, cheeky.

“You won’t. Another is twice-daily maintenance paddlings. Once in the morning and once in the afternoon. This would not be a punishment, but it would help your mindset, and it would make any whippings you earn much more effective and painful.”

“You’d paddle me even if I hadn’t done anything wrong at all?” Dean’s appalled at the very idea. Sir grins at him.

“Absolutely, and with pleasure. And then there’s humiliation. Perhaps putting you in diapers a few days a week, and having you find the staff and ask politely when you need a change.”

Dean freezes cold, then slams away from the table with a clatter. “FUCK no!”

“Dean.” Sir’s voice is a warning, but he can’t hear it right now, it’s not important.

“No way are you putting a diaper on me! I’m not a fucking baby!” He’s yelling and his hands are in fists, fucking bullshit is this, what is Novak thinking about?

Something is shouting in the back of his mind, but he’s too mad to listen, and when Novak reaches out towards him, he shoves his hand away hard, only just keeping himself from following up with a punch.

“Okay,” he hears Novak say, and then his hand is grabbed and twisted and his wrist bent back in some kind of fuck-off ninja grip, and the leverage and pressure crashes him down to his knees, the breath shocked right out of him, his arm straight out to his side, Novak--no, SIR, fuck, fuck--still holding his wrist and thumb at a funny angle.

He pants his fading rage out into the room.

“Normally I’d be putting your disrespectful bottom over a chair right now and whipping it soundly,” Sir tells him calmly. “But we’re going to try something a little different first when you act out like this. You stay right there and take deep breaths. I want you to find your center, and breathe right from there. I know you’re angry right now, but you need to let that go. You know better than to behave like this, Dean. Are you hearing me yet?”

“Hnnng,” Dean grunts through clenched teeth. He is, but he’s simmering, steaming, and his shoulder hurts, and his wrist, and he doesn’t want to give Sir the satisfaction. Deep down, though, there’s a nasty feeling growing. He does know better. And he knows he has controlled his temper before. Guilt starts nibbling at him, shame taking bigger bites once it gets going. Finally, he caves, and slumps down, head dipping.

“Yes, sir,” he mutters.

“That’s better. Come here.” Sir pulls him back up to his feet and turns him to face him. He’s too ashamed to meet his eyes, but Sir tips his chin up and forces him to. “What do you do when something frightens or angers you?”

“I talk to you about it. Sir.” Dean still flares with anger every time he thinks the word diaper, so he tries not to, but.

“That’s right. And who makes the decisions about your training and your activities in this house?” Sir’s eyes are stern and he’s giving no quarter.

“You do.” This is exhausting. Dean would rather be whipped immediately. It’s just making the guilt worse and worse; now it’s almost physical pain. He cringes away from it, holding his belly.

“I’m very disappointed, Dean. Not only did you curse at me, raise your voice, and disrespectfully and disobediently reject a simple idea when it is not your place to do so, you also violently touched your Dominant. That is absolutely unacceptable, and I thought we were beyond this kind of behavior.”

“Oh...oh no...I’m sorry…” the words hit him hard. The regret and guilt and shame burn. He feels queasy suddenly, like his stomach is dropping into his feet.. “No, sir, I’m sorry, I didn’t mean it. Please. Please forgive me. I’ll do better. I’ll try harder to ask next time, I promise.” He’s begging and he doesn’t care. Sir is disappointed in him. That’s awful, that is the worst thing.

Sir softens a little, looking at him. “You’ll be forgiven when you’ve been punished properly. The slate will be clean, and we can start fresh.”

Dean gasps in relief. “Thank you, sir.” His eyes are watering, how did that happen?

“Fetch the switch, baby, it’s by the door. Bring it here to me.”

Dean runs to get it and bring it back. Absolution will come with it, he knows it. He hands it to Sir, and he’s only shaking a little.

“On the bench, Dean. Present.”

Dean swallows hard. Punishments in Present are so much harder. But he hurries, and gets himself into position. Then Sir puts a big round pillow between his knees, spreading them a little further. He holds the switch so Dean can see it.

“You will have eight with the switch on your bottom and two on your anus, Dean. Say yes, sir, please punish me so I may be forgiven.”

Dean’s mind races wildly. Sir is going to whip his hole? But everything aches with the guilt and oh, god, he wants it to stop, wants to be good for Sir again, wants everything to be okay. Tears are already running down his cheeks when he chokes out the words.

“Yessir. Please punish me so I m-may be for-forgiven.”

“Good boy.”

Dean’s waiting for the switch to fall, but instead, he hears a little *snap* and then--AGONY. He’s launching off the bench, screaming, his hands scrabbling behind him, trying to get between his cheeks to touch his burning hole, it’s on fire, it’s bleeding, he has to touch, has to make it stop--

“Dean.” Sir’s hands are on him, getting him back on the bench into position. He’s sobbing wildly.

“No more! No more sir, I’m so sorry, I’m s-sorry I’ll never do it again, sir, please--” Sir is relentless and he wails wordlessly as the bolster is put back between his knees.

“You will stay still for your punishment, Dean,” and then *snap* and he’s going to die, he’s burning, it’s too much, Sir’s hand is keeping him down but his hands are behind him again, trying to block, his throat hurts from the sounds he’s making. And then the first strike falls on his bottom, and jolts his hole, and he is so sorry he was bad but he’s truly paying for it, he’s suffering for his sins, and the second and third and fourth and fifth come and he’s falling, it’s so sweet, forgiveness is the sweetest thing in the world. By the eighth he’s floating, even as he hears himself sob helplessly against his arm, wet with tears and mucus and spit, shaking like a leaf.

“My good boy, my beautiful Submissive,” Sir is humming to him, and it’s music, it’s like angels are talking to him. He cries out when Sir moves him gently, holding him, petting him, and Dean nuzzles against him, needy and small. “You’re forgiven, Dean. It’s all done, now. Good boy, that was very good. You just breathe and rest for a little bit, baby. You were very brave.” Every word soothes another raw spot, makes subspace that much sweeter. Dean sniffles and smiles, tears slowing. Sir gives him water, and it tastes so good. He wipes Dean’s face tenderly, and kisses his nose and cheeks and then his mouth.

It’s not deep, like the last time he was in subspace. He can still feel everything, he’s in touch with everything that’s happening. But it’s still a balm and a little taste of heaven after the pain of before. He feels clean and scrubbed bare, all purified. The harsh edges are all gentled away.

“Is that better now?” Sir asks him, still holding him gently.

“Yes sir. Thank you so much,” Dean says quietly, his voice still rough and soft.

“You’re welcome, sweetheart. We'll continue our talk, including the diapers, later. I think we’re a little late to the training room, but that’s okay. Let’s stand up now, slowly. Good boy.”

Dean whimpers as he stands up. Every movement shifts pressure against his hole, and it feels like it’s on fire.

“You can walk slowly if you need to, Dean. It will burn for a few hours. A reminder of how important the rules are, perhaps?” Sir kisses him gently one last time and then moves away to tidy up the pillow and put away the switch. Dean follows slowly, gingerly, first limping, then walking wide-legged. It hurts no matter what.

It takes longer than usual to get to the training room, but Sir matches his pace patiently.

He’s pretty sure he’s been damaged for life. But when he tells Sir this, Sir just chuckles and leads him over to the big mirror on one of the training room walls, and gives him a hand mirror, and tells him to bend over and look. Cringing, he does. His hole is kind of puffy. A little red. There’s one little darker red mark. And that’s it.

“That’s it?” He’s almost indignant. That fucking hurt, so so much.  It feels like there really should be some kind of visible sign of that kind of pain.

“I’ve told you before I won’t harm you, lovely. I will hurt you, but I won’t harm you.” Sir grins at him and flicks his nose. “And now that you’re reassured I haven’t scarred you forever, we will start on your fetish education.” He claps once and rubs his hands together, like this is exciting.

Okay, Dean admits it is kind of exciting. The edges of subspace are still softening everything, and he’s eager to please his Sir.

“What are we doing first? Sir?” He shifts, winces. “Hopefully something that doesn’t require walking?”

“Oh, Dean. You know that punishments don’t have any affect on my plans. If you earn a punishment, you’ve also earned the consequences during your daily activities as normal. Now, when we are navigating this process, I’ll give you two choices, and you will pick one. For your first experience, you may choose between puppy or kitten play, and feminization.” Sir is smiling at him expectantly.

Dean wasn’t expecting to have to choose. Oh man, he has to pick one? He flushes red. What if Sir thinks he’s really into the one he picks? Or secretly into the one he doesn’t pick? And he has to actively decide on one instead of the other...that means he can’t even tell himself that he had no part in this at all. Oh this is way harder than he thought.

“F-feminization. I guess. Sir.” That room full of dresses hadn’t been too scary. And that one Dom in high school, Rhonda Hurley, wearing her panties had been amazing.

“All right. We have a nice, complete wardrobe of ladies’ things in the third room down,” Sir leads him there. Dean’s face is warm and his heart is going kind of quick. Sir opens the door and flips on the lights, and it’s just like Dean remembers. Racks of dresses and suits, wardrobes and dressers, little labels with sizes on things, and a few comfortable chairs and big mirrors.

“Unlike shopping at the mall, we don’t have to deal with salespeople, changing rooms, or for that matter, undressing you before trying things on. I think we should start with some pretty, lacy lingerie, don’t you, sweetheart?”

Tongue too heavy to speak, Dean just nods mutely. His eyes are huge when he catches sight of himself in the mirror.

“We’ll start with something simple. Green, to match your eyes.” Sir is holding a pair of panties, they look like silk and lace. “Why don’t you put them on, while I go pick a few things out?”

“Yessir,” Dean says, and takes the panties carefully. They feel too fragile for someone big like him, just a scrap of nothing. Sir walks away towards a rack of dresses, and Dean holds them up, figures out where the legs are. Carefully, he steps one foot in, then the other, and pulls them up over his hips.

They’re cool and sleek on his hot, sore bottom and his cock, the lace is just a tickle on his belly. They’re clearly made for men, because they fit just right. Daring, he turns to see himself in the mirror.

They look amazing.

“Look at you, beautiful,” Sir’s voice is admiring, and when Dean checks, there’s no mockery in his face, just sincere appreciation and definitely some lust. It makes Dean flush even warmer.

“I have some dresses for you to try. They’re all soft, pretty things you can just pull over your head to see how they feel. And this.” He holds up another scrap of green. “Pretty breasts like yours should have pretty lingerie, too.”

Dean goes scarlet. “I don’t, I’m not sure how…” he trails off. He’s removed more than a few, but he has no idea how to get that thing onto himself.

“I can help you, if you like,” Sir offers, and Dean nods. Oh yes, please.

“This one is for boys, so it fastens in the front,” Sir narrates. “Here, your arms go through the straps, here. Good.” He cups Dean’s little tits in his palms, gentle, and then ducks his head, taking a nipple in his mouth, licking and then sucking on it with steady, powerful suction.

“OH!” Dean has to steady himself by grabbing Sir’s shoulders. It’s like his mouth is directly connected to Dean’s cock via his nipple, it’s so intense. Sir chuckles, and that’s a whole new sensation, and then switches to the other breast and does the same thing. Dean is swaying on his feet by the time he releases.

“Just making sure you get the full experience of the lace,” Sir says with a wicked smile, his mouth red and a little wet, and Dean’s hazy and ridiculously turned on, and hey, now he knows these panties stretch a lot.

He brings the cups around to the front, smooths them into place, and snaps the little clasp shut in the center of Dean’s chest. He fusses with the straps a little, and then turns Dean to the mirror.

He almost can’t recognize himself. He’s heavy-eyed, face flushed, mouth a little open. The green bra emphasizes the soft rise of his tits, and his nipples are hard and very evident, pressing against the lace. His waist looks smaller, curvier somehow with the bra and the line of green lace panties on his belly, the way they hug his hips like a second soft skin. The lace is a little scratchy against his nipples, which is new and kind of strange, and keeps his mind going to them.

“So pretty, Dean. What a pretty girl.”

Without thinking, Dean shakes his head, frowning a little.

“No? Are you still a girly-boy in pretty lacy things?” That sounds a little better, for now, and Dean nods, relieved. “All right, lovely boy. Let’s try a dress.”

Dean doesn’t like the first one. The sleeves are too short and small and it makes his arms look huge and bulgey, like he’s going to bust out of it. Sir laughs a little and agrees when he points that out, and helps him pull it off. The second one is perfect, though.

It’s a summer dress, light and flowing, with a wide v-neck and fluttery half-sleeves. The soft fabric of the body is snug until it bells out into a swirly skirt that comes almost to Dean’s knees, and it’s light blue, with white details around the neckline and a white fabric belt, and white lace at the hem.

He makes a cautious spin, and has to laugh a little at the feeling of the skirt swinging with him and then settling around his legs.

He’s so pretty in the mirror he almost can’t look at himself, except in shy, quick glances.

“Do you want to try makeup and hair, too, or is this enough for the first day?” Sir has a pair of white shoes in his hand, and they’re little slippers, it looks like to Dean, who doesn’t know anything about girls’ shoes.

“I think this is enough?” He looks to Sir for confirmation, and he nods. Helps Dean get his shoes on, and they fit, and they’re comfortable, how weird, and then extends his elbow like a gentleman in an old-timey movie.

“If I may do the honors,” Sir says with exaggerated manners, and Dean laughs a little, feeling light and happy, and slips his hand into Sir’s arm. Even though it hurts his aching hole, it’s worth it to walk with a little swing in his hips to feel the skirt sway around his legs, as Sir leads him back out into the house.

 

Chapter Text

To: ALL
From: GarrisonBoss
DailyDigest

Winchester Update:
Dean will be feminized over the next few days in training. He is taking to it very well; please feel free to compliment his dress and lingerie, if visible, if you wish. Please continue to refer to him as a boy, he is not yet comfortable with female terms while in female clothes.

He had a violent outburst at mention of diaper discipline today. Reminder to all non-enhanced/supernatural staff: ensure at least two Dominant/Dominant Switch staff are present at all times, or that adequate restraints are used, when with Dean in any potentially challenging situations until this Submissive is completely settled. Yes, this means you, Benny. This is for the safety of the staff, the Submissive, and the house. Any questions please see me.

Anal whipping is now in the punishment rota. FYI, Benny.

House Update:
Charlie Bradbury will be returning to the house on Tuesday. She will be under Meg’s Dominance and care as usual for the week she is here upgrading the house security systems and network, with the able assistance of Ash. She has asked me to remind everyone to please leave your work computers on, but logged off, at the end of each day, so she can start the upgrades remotely.

The main driveway is being resealed this week. Please direct all deliveries to the alternate entrance on Colby St.

Be sure to schedule your Training Room time early! With two Submissives in the house full-time the space will be busier than usual. The calendar is shared with everyone, and with the exception of Dean’s training, the room is available on first-come, first-serve basis, as you know.

Reminder to all staff who live on the grounds or in the main house: proposals/requests for remodeling, painting, large maintenance or improvement needs and projects need to be in by the end of next month.

Novak Corp is running a free webinar series in July and August: Short-Term, Long-Term, and Permanent Contracts: Reading And Understanding The Fine Print Before You Sign. Relevant to both Dominants and Submissives, lots of great info. The advertising campaign should be airing soon, please keep your eyes out!

Dominant Delight in Austin is hosting a Caning Seminar the week after next. I can confirm the clinicians are excellent and the clinic should be fun and informative. Free to attend for any staff who wish to go. Date is on the public shared calendar, just let Meg know so she can schedule coverage if you plan to attend.

Thank you all as always for your hard work and dedication!
Castiel

TO: GarrisonBoss
From: InfernalMeg
Re: DailyDigest

Hey boss-

Charlie’s been in touch and her latest contract was a dud, she cancelled it early, so we’re going to be in a pretty strict dynamic while she’s here, she needs a lot of care and attention. Let me know if there’s anything specific that would be helpful for you and the kid and I’m sure we can work it in so he can get some exposure.

Can’t wait to see that cute lil butt of his in a dress! >:D
See you tomorrow, pinches and spanks to Dean,
Meg

TO: GarrisonBoss
From: LafitteB
Re: DailyDigest

Boss- You don’t mean I have to restrain him for his enemas, right? Those aren’t challenging at all, he practically purrs for them. It would ruin the whole vibe I like to set anyway. Ask Claudia, she always wants spankings with hers and I just won’t do it. Anyway, that’s my thoughts.
Benny

TO: GarrisonBoss
From: ArchGabriel
Re: DailyDigest

Did you know I was on your ALL mailing list? I bet you didn’t, but you do now! What the hell is a ‘violent outburst?’ At least the dress thing gives me hope. If you can get him into really high heels I bet his fatality rate falls by like 60%.

Call me!
Your loving brother

TO: GarrisonBoss
From: @$#
Re: DailyDigest

Hey Sir-

You know I could totally do this upgrade on my own, right? Charlie’s just coming in for consulting and some outside networking expertise, she has a better handle on some of the router configs but I could have totally worked it out by myself. Anyway just wanted to be sure you knew that. Glad to hear Dean’s doing good. Oh we need a new AC unit for the server room.

Ash

***

Castiel leans away from his desk, and firmly logs out of his computer. No. He will not be reading any more emails today from his staff or family. Reading just one more might drive him insane. He spins in his desk chair, and smiles at the sight.

Dean’s in free time, but he said he’d rather ‘hang out’ with Castiel than be put in chastity, since he likes the feeling of the panties too much. He’s sitting on the couch, but instead of sprawled out as usual, he’s half-curled against the pillows. The dress is draped demurely over his thighs, and he’s actually humming a little, tunelessly and soft, as he flips through a magazine.

“You’re prettier than a picture,” Castiel says, meaning it, and Dean looks up at him surprised, and then flushes. Castiel gets up, abandoning his desk, and moves to one of the big chairs. “Come here, you pretty thing.”

With gratifying eagerness, Dean tosses the magazine aside, and pads over to him, smiling. The Dean who seems to live at the intersection of bravado and bad ideas is gone for the moment; this Dean is a little shy, eager, and entirely adorable. Castiel pats his thighs. “On my lap, pretty. That’s right, swing your knee right over.” As Dean settles tentatively astride his thighs, he slides his hands up under that skirt, until he’s palming the lace and silk over Dean’s hips.

“You’re done with work, Sir?” Dean won’t quite meet his eyes, but his hands are on his chest, smoothing his shirt a little.

“I am. And I have proof I’ve been thinking about you the whole time.” He pulls Dean’s hips down firmly against the hard, hot ridge of his cock in his pants, so it gets right up against all Dean’s tender soft parts.

“Oh!” Dean’s eyes fly wide, his hands grab Castiel’s shirt, and his mouth drops open. There’s a touch of pain on his face--Castiel knows his bottom is still quite red and hot--but mostly excitement. “You, um. You really like how I look, huh?”

“Very, very much. I know you’re on free time, but I’ve been thinking I should just bend you right over my desk, flip your skirt up over your back, pull your panties aside, and have my way with that sweet little pussy you’ve got all wrapped up in silk.” He leans up and kisses Dean deeply, swallowing his gasp, and when he pulls back, Dean’s blush goes all the way down his chest, meeting the low neckline of the dress.

“Or maybe I’ll have you take off your panties and leave them with me. Walk around all bare under your dress, naughty and hard, until I can’t stand it anymore and take you to bed. Would you like that, darling? Being my naughty pretty little thing?”

Dean’s eyes are all pupil. Even through the panties and the dress, his cock is ragingly hard, his erection unmistakable.

“Y-yessir,” he stutters, his voice a thin little thread of sound. His hips give a hesitant grind down, and Castiel rewards him with a groan, his own hands tightening on Dean’s hips.

“Careful, sweetheart, or the first option will be it, and I don’t have any lubricant in this office,” he pinches Dean’s hip with a grin that’s half-threat. Dean gulps and his hips still.

Then he cocks his head and actually teases, “A switch in every room, but no lube? What kind of boy do you think I am, Sir?” He even flutters his eyelashes a little, and Castiel laughs, delighted.

“A very naughty one. Perhaps that can be a task for you tomorrow: distribute lube throughout the house. My last Submissive in training was female, so although of course lube was essential, if the matter was urgent I could make do.” He kisses Dean again, unable to help himself. “An oversight, clearly. I will try to make it up to you. Up, off my lap, you tempting boy. Panties off.”

All pink and pleased, Dean does as he’s told. He wobbles a little as he steps out of the panties, but hands them to Castiel without hesitating. Setting them on the desk, Castiel reaches out and puts his hands on Dean’s waist, then smooths his palms down the front of his hips. Pulling the skirt tight over the jut of Dean’s erection, tenting it obscenely.

Dean sways, a little moan falling from his lips.

“We need to go and make sure the house is closed up for the night and fetch a few things from the training room before we go to our room, Dean,” Castiel tells him, smiling. “I think this cute dress is going to make our walk feel very nice for you, but you are not to touch, not even once. If you do, I will spank your cock very hard, and you will wear chastity for the next week, do you understand?” Dean nods, looking down at him, licking his lips. “Good boy.” With a final pat to Dean’s hip, he stands up and gets them moving.

The house on Sundays is quiet, but people do still come and go, and Castiel always makes the rounds in the evening, checking door locks and making sure the lights are off. Dean walks quietly beside him, only the occasional quick breath betraying that the dress is brushing against him as he moves and teasing him delightfully.

Castiel gathers up a few things he’d set aside in the training room; more lingerie sets, a few simple, soft shifts, some dresses made expressly for Submissives that are entirely sheer, and some ruffled nighties. Dean watches him, clearly curious.

“What are those for?” He finally asks.

“I think we can both tell that this particular kink is a winner for you,” Castiel grins at him, and Dean smiles back, a little abashed. “These are coming to our room, so I can dress you in them without running back and forth all the time. Eventually we’ll practice full evening wear, and Crowley will help you learn cosmetics--he is incredibly talented--and hair, as well as jewelry and shoes, the whole package. But for now I think this will suffice.” Dean is nicely stunned by that, eyes tracking to the rack of evening gowns, each carefully stored in a clear zipper bag, lying in exotic and mysterious wait.

One more stop in the main room, for a selection of cock rings that has Dean’s eyes going wide again, and Castiel turns off the lights and locks the door behind them.

As soon as they reach the bedroom, Dean’s nearly vibrating with eagerness, and Castiel has to laugh. To think, just a week ago, this boy had to be strapped down! He hands the armload of clothing to Dean, and indicates the small dresser and wardrobe to one side of the room.

“Put away your dresses and panties and bras, baby. Fold them neatly and hang the dresses up, and then pick out a nightie for bed. You know where the stretcher is, I want you to prepare yourself. Only five pumps tonight, Dean. And Dean?”

Bright-eyed, Dean turns back from where he’d already started moving. Castiel reaches out and lifts the dress. As expected, the boy’s cock is red and hard, wet at the tip, and he’s quite sure Dean won’t be able to control his orgasm in this state. He picks a slim leather cock ring with a rough inner surface and a strong snap, and fastens it around the base of Dean’s cock.

“Ah!” Dean twitches a little at the feeling of it.

“I’m saving you from yourself,” Castiel informs him, and lets the dress fall again. “Scoot. I expect you to be nice and wet and stretched by the time I’m done preparing for bed.”

Dean scoots.

“Ow ow ow OW!” Castiel hears, as he’s cleaning up at the sink, and he grins wickedly at his reflection in the mirror.

“Five pumps, baby,” he calls through the door. “I know your hole is sore, but it will stretch.”

“Y-yes sir,” Dean says in his smaller, lighter voice, the one Castiel is starting to think of his girl-clothes voice. He smiles to himself. It’s a different headspace, roleplay like this; not subspace, but a different mindset, and Dean seems to be embracing it fully.

Once he judges enough time has passed, Castiel spreads lube on himself, he’s not going to want to wait. “On your back, Dean. Hand behind your knees, hold yourself wide, wide open.” He leaves the bathroom and god, what a sight.

None of the nighties are demure, but Dean’s chosen a hip-length sheer cream gown with thin straps and a loose top that does more to expose his breasts than hide them. His cock is pillowed on a mass of ruffles, bunched at his waist, and his spread and lifted thighs expose his gently stretched, glistening wet hole, still red from its previous punishment.

His face is flushed red and desperate, plush mouth open and panting, eyes heavy and dark. He looks at Castiel’s nakedness and moans.

“Oh baby,” Castiel croons, approaching. “Oh, look at you, how desperate you are.” Dean whimpers, nodding, pulling his knees a little closer to his chest as Castiel crawls onto the bed, prowls up it on hands and knees towards his Submissive. Surging up between Dean’s thighs, he braces himself on his hands on either side of Dean’s body, and shifts until his cockhead is rubbing against Dean’s hole, teasing and prodding.

“Oh oh oh.” There’s a thread of fear in Dean’s moans, but mostly raw need. Castiel rubs again, circling his hips, enjoying the slick slide and the way he can feel Dean’s hole flutter and clench.

“That feel nice, baby? You need more?” His voice is thick and dark, he can feel all the muscles in his back tighten and clench with the urge to thrust and claim. “Can you ask me nicely, sweetheart?”

“P-please,” Dean manages to get out, and then his hips rock a little. “Please, Sir!”

“Now this may hurt, sweetie,” he warns, as he gets his hips lined up, lets the rigid tip of his cock sink just barely into the softness of Dean’s hole. “Sir’s cock is so big and hard, and your little bottom is very tight and red. But I want you to keep your legs nice and wide for me. You can be brave for me, right baby?” He waits.

Dean breathes hard and chews his lip, his hips are rocking a little, still. “Yes,” he finally breaks, “please, I can, I need it, please do it, Sir please please it hurts I need it,” he’s been aroused for so long, Castiel can see desperation in every line of his face.

Finally, the muscles in his back and thighs and ass can flex and release, and he drives himself up and in, past the mild resistance of Dean’s tightness, all the way in to the base. Almost gasping with the relief of it.

“Oh oh nnn, NNNNNNN,” Dean wails, teeth clenched, head back and throat tense. Castiel has never been able to see his face before, and his suffering is exquisite. He hardens further, with a jerk and swell, and Dean cries out again, tears running from his closed eyes down his temples. The cock ring is keeping him hard, and Castiel knows he was stretched, so much of his distress is frustration and overstimulation.

Being sure to stimulate all his sweet spots, Castiel sets a punishing, relentless pace. Dean’s hard cock rocks into his bunched-up nightie on every thrust. His little whimpers and cries fall from his lips like music, but Castiel can tell when the pain disappears and the frustrated arousal takes over; the tone changes, Dean’s squirms become deeper, looser.

“Just a little more, darling,” he murmurs, quickening, hips pumping fast, as he leans in, bites down on the tempting swell of breast exposed by the sinful little nightgown. Dean squeals, shock and pain clenching every muscle of his body and the sudden hot vise of his ass brings Castiel over. His orgasm is explosive and so powerful he shoves them both up the bed as he comes, his cock digging deep and spending fully inside Dean’s body.

Easing down from that incredible high, he feels Dean’s shuddering breaths against his neck. They’re pressed together tightly, Dean’s legs up on his sides, his own cock still jerking with aftershocks into the hot, wet heaven of Dean’s hole. Castiel eases back just a little, smooths his hands down that pretty nightgown, stroking Dean’s sides, his belly, never approaching his cock, still red and hard and angry, trapped by the ring.

“Mmmm,” Dean hums, and his face looks deeply sated, slack with pleasure. Perfectly Submissive. No orgasm, and none coming, but he is clearly absolutely fulfilled, satisfied, and nearly purring under Castiel’s hands.

“Such a good boy,” he praises, finally pulling free. Dean makes a little complaining noise, but drops his legs at Castiel’s urging. “You were perfect for me, baby. I’m so very pleased with you. Here, sit up, let’s take this off for now.” Gently, he eases the nightgown from Dean. It’s time to give the boy some time to process, accept, and adjust. Sleepy-eyed and pliant, Dean lets himself be moved.

“How do you feel?”

“Sore inside. Bruised.” Dean glances at him, almost sly. “Just like you like it, Sir.”

Smiling, Castiel shrugs a little. “Well, you’re not wrong. But I meant about the dresses and lingerie. Stay awake a little, Dean, we still have to deal with that.” He points at Dean’s groin.

“Deal with it how?” That’s gotten his attention, and a little bit of alarm.

“The ring is too tight to leave on all night, but we can’t have you so close to orgasm and uncontrolled, can we? So,” he slides off the bed, and makes his way to the bathroom. An absorbent cloth run under icy tap water for a few moments, and he returns. “We deal with it.”

“Oh shit,” Dean breathes, warily watching him.

“Deep breath,” Castiel warns, and then presses the cloth to his cock, while unsnapping the ring. Dean convulses, jacking up into a curl, and Castiel rides it out, feeling the erection soften and shrink under his hand with the cold.

“Fuckfuckfuck” Dean gasps, and when the cloth pulls away, he’s soft.

“Good boy, very good,” Castiel puts the cloth in the laundry. “Now, do you need your chastity cage tonight? I know today was very stimulating. It’s okay to need it, just be honest.”

All the sleepy pleasure is gone from Dean’s face; Castiel can sympathize, since he supposes an ice-cold washcloth to the genitals would wake him right up, too.

Dean scowls, and shakes his head. Then nods. Then shakes his head again.

“On your head be it, if you orgasm in your sleep,” Castiel warns, and Dean scowls harder. Then nods.

“I thought so. Now, unlike the lube in my office, I did think to keep a spare here in the bedroom. Lift up a little, lie back, that’s good, sweetheart. I think it might be a good idea to have some custom cages made up for you. They’d be sized just to fit you, very comfortable, and more attractive, too--” he talks Dean through putting the cage on his highly-sensitized penis, locking it in, and making sure it’s adjusted properly. When he’s done, Dean is breathing a little hard, but looking more relaxed again. Ready to sleep.

Impulsively, Castiel leans in and kisses him. Not as a gesture of Dominance, not to provoke a sexual response, but because he looks debauched and pretty on the pillow, and Castiel wants to kiss him. And as Dean curls close to him in sleep that night, Castiel lies awake, staring into the darkness, worrying.

Chapter Text

Dean is not having a good morning.

He wakes up and his cock is sore from trying to get hard inside the cage. It’s an aggravating, nagging ache, and Sir only laughs at him when he complains about it. And he has to sit down to pee with the cage on, too, which just makes everything worse, and Sir leaves it on him.

Sir doesn’t even use him for sex, either. He says Dean had been pushed enough last night, which, whatever, Sir’s not the one getting a baseball bat shoved up his ass, Dean should get to make that call, right? But they just take showers and shave and do normal morning stuff. It’s hard to believe that pisses him off, but it does.

And then, then, Sir dresses him in this thing, it’s...it’s not even a dress. It’s shaped like a dress, it has a low neckline and a waist and a skirt like the dress yesterday, but it’s more loose and flowy. But it’s this pale gold color and it’s completely see through. Dean feels way more naked in it than he did when he was actually naked.

Dean tells Sir there’s no way he’s leaving the bedroom wearing this ridiculous thing.

Sir tells Dean he had better check his attitude quickly, and that he will in fact be leaving the bedroom wearing his pretty Submissive dress which Dean himself had said he liked the day before. And he can choose right now whether he’ll do so with or without fresh stripes on the bottom underneath.

Dean leaves the bedroom wearing the ridiculous thing.

Sir stops him outside the dining room, and cups his face in both his hands, and looks into his eyes. His stupid blue eyes are all soft and understanding.

“Dean. Everyone has bad moods, bad days, even bad weeks. You’re not a robot, and no one expects you to wake up singing every morning. But you may not take that bad mood out on me or other people in the house. That’s both unfair and against your rules. So I want you to think about that while we eat, and if there’s something I can do to help, you let me know after the meal.”

Dean has to nod at that. “Okay. Yes, Sir. Sorry.”

“It’s all right. Come on. Some good food can only help, hmm?”

Sir shows him how to kneel mostly gracefully in the dress thing, without it getting all twisted under his knees, and feeds him some bacon, first off. So the morning is getting a little better. Then Meg walks in, joining them for breakfast like she sometimes does, and Dean has to stare hard at Sir’s leg, bracing himself for some kind of comment.

“Morning, Boss. Morning, Dean. That dress is gorgeous.” She strolls on by and serves herself eggs, and Dean blinks, because...is that it?

Sir’s smiling a little at him, and offering him toast. Dean takes it, bemused.

“Have you told Dean about Charlie yet, Boss?”

“I haven’t. We have a consultant coming this week to work on the computer systems, Charlie Bradbury. She’s a low-level Submissive, and Meg will be her Dominant while she’s here. They have a standard short-term contract in place for when she visits.” He offers Dean another piece of bacon. “She’s also gay. I’m sure I don’t have to tell you this explicitly, but there will be no tolerance whatsoever for any homophobic sentiments, words, or behavior in this house.”

Dean chews hard and swallows. “Like, she’s really gay?” Holy shit!

“As opposed to fake gay?” Meg’s rolling her eyes, he can tell just from her voice. “She’s married to the love of her life, another Submissive. They both have a few routine, short-term non-romantic Dominant contracts every year to make sure they stay healthy, of course. Apparently California has fifteen or sixteen different dating services you can use to find what you’re looking for? Though usually she just goes through one of the Novak schools.”

“How does that even work?” Dean’s fascinated. He's messed around with another Sub before, but it was all just physical, casual stuff, nothing with a dynamic or any romantic feelings. “Who’s holding her Responsibility papers?”

Meg laughs.

“They just used a fake name. Nobody really checks those things. And they sign them over and get them back for the short-term contracts, and everyone’s happy. I mean, even fifty years ago, no way. They’d have had to each marry another Dominant in the same situation, and hide everything, like in the movies. But it’s a lot easier now.”

“What if they get caught?”

Sir answers that one. “The original purpose of the Record and Responsibility papers, a hundred years ago when they first became mandatory, was to ensure the safety and well-being of Submissives. Too many were being neglected, arranged into marriages with inappropriate dynamics, or were not having their needs met and being driven to what they called “gland madness” at the time.” Dean remembers that crap from History class, and he nods. “So the Responsibility papers were to ensure that the Dominant who held them was made legally and enforceably accountable for that Submissive’s health, happiness, and so on. It was quite progressive for the time.

“Now, of course, Submissives have a great deal more agency. The law is perhaps more than a bit dated. To answer your question, they would probably be brought up on forgery charges, but I would happily step in and sign their papers to prevent them becoming involved with the State system, and sign another committing to holding no authority over them, if it came to that.”

“That’s because you’re the best Boss ever,” Meg says.

“That’s very rah rah Submissive Rebellion of you, Sir,” Dean says, admiringly. “Didn’t you say you’re Traditional?”

“I am, and I wouldn’t go that far,” Sir answers, lips quirking as he holds another piece of bacon to Dean’s lips. “Just because I see nothing wrong with their love story doesn’t mean I don’t require a certain level of respect from you, young man.”

Meg giggles, and Dean eats his bacon.

Krav Maga practice is awesome, and Dean maybe gets a little too into it. He gets to shed the dress thing and his chastity, and put on pants and the practice shirt, and hit and tumble and block. The third time he flips Meg over his shoulder and slams her hard into the padded mat, Sir taps him on the back and sends him outside to run with Cole in the light rain. They run the whole property perimeter, and Cole runs just like Dad used to, steady and dogged like he still has combat boots on. It’s mindless and perfect and by the time they’re done with the whole six miles, Dean feels about a thousand times better, even though he’s wet to the skin and exhausted. And Sir is waiting, leaning hip-cocked on the door to the workout room, grinning at them as they run up.

“You couldn’t be training an out of shape Sub? I ain’t run like that since Ranger school,” Cole complains. It’s the first thing he’s said since he warned Dean about a stump two miles ago, and Sir laughs, as Dean bends over with his hands on his knees, getting his wind back.

“I’ll take him off your hands so you can go clean up and dry off, Cole. Try not to drip too much on the mats.” He strips Dean out of his soggy training gear and dries him off with a big rough towel that leaves his skin glowing, and then takes him to the training room, and puts him in a hot shower that feels like heaven.

When he comes out, clean and smelling so much better, Sir’s waiting by the clothes rack.

“I can see the dress isn’t working for you today,” he starts, and Dean winces a little.

“I didn’t hate it. It was okay!”

“No, we’re exploring. It’s all right to like some things more than others, though you do need to try. So we’re going to try something else now. Not a dress, but still very feminine and pretty.” He takes a box off the low table. “Display.”

Dean slides to his knees, hands behind his head, knees spread, elbows back, back arched.

“This is body jewelry. It’s meant to draw attention to your beauty.” Sir smiles at him. “Not that you need any help, but it also feels good. First, a necklace.” He draws out a long silver chain, and loops it over Dean’s head, making him move his hands so it settles around his neck. It falls down both his front and back; he can feel it between his shoulder blades. There’s a knot that rests right over his sternum, and three green stones dangle on thinner chains below it. “This would sit below a collar, if you were wearing one.”

The stones tickle the top of his belly a little when he breathes. Dean smiles. Sir paying attention to him like this, now that he’s run off most of his bad mood, is making butterflies start doing somersaults in his belly, and now the chain is joining in on the action.

“Now your breasts.” Sir plucks and pulls at a nipple until it’s stiff and dark, and Dean is chewing his lip to keep from moaning. He slides a small silver cap over it, with tassels of chains and more tiny green stones, and tightens four little screws until Dean can feel the pinch. He does the same on the other side, and sits back.

Dean looks down. His nipples are silver, with jewels. It is kind of pretty.

“Arms and wrists.” Thin cuffs around his biceps, no chains on these, just green studded gems. But the wristbands have waterfalls of jingling silver tipped with green that almost reach his fingertips, and fall back on his wrists when he raises his hands.

“The belly chain.” This one has heavier links that sit low on his waist, and clasps well below his navel, with the rest falling loose. A dangling chain behind rests cool between his cheeks, and he can feel the weight of a stone there too, falling lower, just brushing the crease of his thighs. The jewels on the front chain tap his pubic bone, and he shivers a little.

“For your penis.” A filigree...cuff? It looks like a cuff. It has dangling green gems, too, and Dean sucks in a breath as Sir gently works it onto him. It has a little give to it, so if he gets harder or soft it will stay on, and there’s a solid circle that notches into place just under the head of his cock. It has a little ring, too, where you could attach something else, it looks like.

“Some like to use a leash with things like this,” Sir murmurs. “I prefer them to be purely decorative. All right. Stand up, please.”

Dean stands, careful and shaky.

“Ankles.” Three strands of chain, separated by a bar, that shift and move with every step without interfering.

“All right, lovely. Now turn around, and watch yourself walk to the mirror.”

Dean turns and catches sight of himself, and almost loses a step as the chains sway and shift against his skin, like a touch, and he sees them in the mirror.

“It’s exotic,” he breathes, staring at himself, at the shine of the chains, the way silver shifts and shimmers, drawing eyes to his sex with every tiny move he makes.

“Very,” Sir agrees, his voice rough. “And lovely. I have gold and blue as well, but the silver and green on you, with your eyes…” he lifts his hands, and meets Dean’s gaze in the mirror. His look is hot, heavy. “They are not for everyday. But they are unusual, a bit pagan, a little wild. I thought they might suit you.”

“Can I keep them on for now?” Dean asks hopefully. He takes a little step, and silver and green ripples back at him from the mirror.

“Of course, sweetheart. This can be your fetish training wear today, and after, we will put them in your dresser, to keep.” Sir grins at him. “I confess I am delighted you like them.”

“I love them,” Dean declares. “They’re awesome. I look like a harem bellydancer, only better.” He turns quickly to feel the chains sway and swing. “Thank you, Sir. They’re amazing.”

“You are very welcome. Now come. I believe you have a mission to undertake. Something about putting lubricant into every room in the house?”

Dean takes Sir’s arm again, just like yesterday, and just like yesterday, he’s laughing. His afternoon is shaping up a lot better than the morning.

***

“Jesus please us, Dean.” Claudia, laundry basket on her hip, stops in the hallway and puts her free hand on her chest. “You should come with a warning label, boy. My goodness, just look at you.”

Dean doesn’t even feel shy. He grins at her and shakes his hands a little, to get the silver chains moving even more. Kind of like before, when someone would throw him a sincere compliment, it’s just kind of cool, nice. He can tell she means it.

“They’re cool, right? I love ‘em. I guess they’re supposed to be for special occasions, but Sir says I can wear them today, even though I’m just running around doing random stuff.”

“Give us a turn, let’s see the whole thing,” she encourages, and he does, pleased. “Oh my. Just stunning. And Dr. Novak has you out and about unchaperoned, and without chastity?” She raises an impressed eyebrow. “That’s a lot of trust he has in you. You must be making a wonderful impression. Well done, Dean.”

He smiles gratitude at her and gives her a thumbs up as she moves on towards the laundry room, while his mind keeps working over the problem it’s been nibbling at all afternoon.

Dean knows he’s not super smart. He’s nowhere near Sam, okay? He’s not winning any scholarships or blowing anyone out of the water with his brains. But he’s pretty street-smart. He’s got good situational awareness, even Dad always said so, and a solid grasp of tactics and probabilities. Plus, people, he’s always been pretty good with people.

And part of him is still freaking out about the fact that he’s not more freaked out by all this.

He remembers how shitty he felt before coming here. Getting blackout drunk, way more times than anyone knows about, because it kept him from spiking back and forth between crazy twitching anxiety and what felt like the worst sadness in the world. He’s never been all that tolerant of strange Doms getting pushy, but the rage he’d felt when they’d even talked to him then, that had been out of control and scary as shit. And he’d felt sick all the time, too, his stomach all cramped up and miserable. Some of it is honestly kind of a blur, but he’s far enough away from it now to admit that yeah, he’d definitely been in trouble, and he’d been so deep in it he couldn’t even see it or admit it or understand it. Now he feels so much better, it doesn’t even compare.

So there’s that.

Dean tucks a small bottle of lube in one of the drawers of the big cabinet in the dining room, and as he turns away, the jewels on his belly chain swing and tap against his pubic bone and the lowest crease of his crack. It’s pure pleasure, the tickle and tease, a rush that’s only matched by the lingering warmth from Claudia’s words, knowing Sir is trusting him, approving of his progress, giving him these extra freedoms.

Is it more crazy that he’s smiling about that, or that he’s happily stashing lube all over the house so his Training Dominant can more easily fuck him, wherever they happen to be?

Dean puffs his cheeks, holds them like that, and then blows out the breath. Sir keeps talking about accepting his Submissive nature, and Dean thinks his body’s on Sir’s side. It feels like a hand on his cock when Sir praises him, like a hit of good drugs when Sir orders him around, and like a full-body orgasm when Sir uses him intimately and finds his pleasure and is happy and satisfied and pleased with Dean’s service. He’d never expected that. He hadn’t known it would feel so natural, that it would get easier and easier to obey, submit, bow his head to Sir and give himself over. And that’s what’s freaking him out. It isn’t hard at all. He’d planned to fight, tooth and nail, all the way. But he doesn’t even want to, anymore, a lot of the time. That’s so fucking scary.

Even when there is pain that makes Dean scream and sob and claw at the bed, deep down, the pleasure and fulfillment is rich and dark, like really good chocolate.

It’s only been a little over a week. Shouldn’t it be harder than this, take longer than this, to make a change this big?

This thinking thing is hurting his head, and when Claudia sticks her head into the dining room, he smiles at her in relief.

“I thought you were headed this way. Dr. Novak wants you to join him in his study. He says there’s a phone call for you from your family.”

Dean runs. He’s pretty sure Sir would have come for him personally if it was an emergency, but still. He busts through the door a few moments later, to see Sir smiling and nodding as he listens on the phone. Everything’s okay, then.

“Here’s Dean,” Sir says, and hands the phone over.

“Hello?”

“Hey, son.”

“Hey, Dad,” Dean replies automatically to that voice, though his mind is spinning.

“I’m sorry for calling in the middle of the day like this,” his dad sounds awkward, he never sounds awkward, “but I wanted to let you know right away. Sam’s school got in touch this morning, he’s presenting. He, ah, the test came back as high-level Dominant. Now, I talked to your Mr. Novak, and of course we’re gonna confirm that test with one of their training schools this time. But it’s a pretty big day for Sam. I know he’ll be calling you later, but I knew you’d want to know as soon as I did.”

Dean’s smiling, big, even as his eyes sting and prickle.

“That’s...holy crap, Dad. That’s awesome. Little Sammy’s finally growing up?” He chokes out a laugh, and hears his dad echo it.

“Yeah. Yep. Pretty crazy. You did a fine job raising him, kiddo, don’t think I don’t know it. I gotta get back to work, but you take care of yourself, Dean. I’ll see you soon, all right?”

“Okay. Thanks, Dad.”

He hands the phone back to Sir, dazed. He’s still smiling, but his cheeks are wet. Sir puts the phone down, and wraps him up in his arms, his big hands warm and gentle on Dean’s back and hip.

“Tell me?”

“Sammy. He’s presenting.” Dean laughs again, and he’s so happy for Sam, his brilliant, amazing little brother, who’s gonna have every chance in the world to do anything he wants, and the tears won’t stop coming. “He’s high-level Dominant, the school says. What are the odds?”

Sir wipes the tears from his chin with a gentle thumb. “Just as slim as for a high-level Submissive. About five percent of the population are high level either way. You Winchester boys are clearly destined to take things to extremes.”

Dean giggles, watery, and bumps his forehead against Sir’s shoulder. “He’s gonna put Dad through hell, huh?”

Sir rubs a gentle hand up and down his back, under the necklace chain. “I think it’d probably be best for everyone if he starts classes sooner rather than later. Come here, sit with me, sweetheart.” Dean lets himself be moved to the couch and settled there, half in Sir’s lap, held close. “How much do you know about Dominant training?”

Dean shrugs. “Not much. I mean, we all had the same Sex and Dynamics classes in school, but that stuff was all pretty vague.”

“Right.” Dean grins a little as Sir predictably mutters for a moment about public school sex education, and then gets himself back on track. “Just as your Angel Glands developed because you are a Submissive, in a Dominant, between age thirteen and fifteen, the King Glands grow and start producing hormones. Tell me they taught you that, at least.”

“Oh, sure,” Dean nods against his chest. “The Top Knots. The Master Blasters. The Crown Jewels.”

“Good lord,” Sir sounds appalled. “Are they really called that?”

“I could keep going,” Dean offers.

“No, thank you,” Sir declines hastily. “As I was saying. They are located in the small of the back just above the pelvis, in the base of the throat, at the base of the penis or clitoris, and high in the chest, near the join of both shoulders. For a few years yet, they won’t mature. Sam won’t see many changes, besides developing instincts and urges towards Dominance. Training classes now will be age-appropriate, introducing concepts of responsible and healthy Dominant practices, and start laying the groundwork for the more advanced work later.”

He tips his head so he can see Dean’s face, and smiles. “In our schools, we expect the more senior student Dominants to experience all the punishments and disciplines they learn to administer. And they are, almost without exception, enormous babies about it.”

That startles an actual shout of laughter out of Dean.

“Are you serious? Sir!” He can’t stop laughing, imagining red-faced, red-assed Dominants squalling like infants at having a stripe put on their butts.

“I’m absolutely serious.” Sir’s laughing a little too. “If they don’t know how it feels, how can they know if it’s appropriate discipline for their Submissive, when the moment comes?”

“I guess that makes sense.” Dean thinks about it. “Does that mean you’ve felt everything you do to me?”

“I have,” Sir confirms gravely. “I know precisely how painful each correction will be.”

Dean sniffles a little, with a nod.

“So, Sam won’t be Dominating anyone right away? He won’t be trying to tell me to kneel or anything, next time I see him.” It’s a niggling worry.

“No, and you would be well within your rights to tackle him harder than you did the last time, if he made the attempt,” Sir laughs again. “The sexual maturity of his glands will eventually lead to the Dominant voice, as well as the ability to maintain an erection for long periods of time when interacting with a Submissive, and a few other traits. But first and foremost, he’s your younger brother, and as with any other Submissive who has not offered him their surrender, he has no business ordering you to do anything at all. That’s a pretty fundamental thing he’ll learn.”

“Yeah, we should definitely get him signed up for classes,” Dean says. That sounds nice, but remembering high school, and some of the older Dominant kids who’d strutted around dropping commands like they owned every Submissive ass in sight…

“I spoke briefly to your father, before you arrived. He told me Sam had presented, though not how, and we confirmed he would get a more precise test, and be scheduled to join the first beginners class we have starting next.”

“Thanks, Sir,” Dean says, quiet. He wishes he was there. Wishes he could have heard Sam’s big news in person, could have given him a hug, talked it out with him. Taken care of him, like he always has. But this is maybe the next best thing, knowing that Sam’ll have good options, real knowledge, good people showing him the ropes.

“You’re welcome. It will be just as important for him to know and understand his orientation as it is for you. And very challenging, although different. He’s lucky he’ll have you in his corner.” Sir kisses him lightly on the mouth. “Now, why don’t we go take off your jewelry, and pick out a pretty dress and panties for the rest of the day? It’s been a long time since lunch, and it’s almost your free period.”

“Okay,” Dean smiles a little. Sam, of course, will never wear shimmering chains, or a frilly dress. He wouldn’t enjoy it, for one thing, as Dean’s honesty forces him to admit to himself. And he’ll never be expected to kneel, Dean also thinks, with only a little bitterness. But he’s going to call later, and Dean will listen to him tell all about it, and Sam will be so excited, and Dean will celebrate right along with him.

Chapter Text

This morning is even worse than yesterday.

Sam had been over the moon excited to present, and he’d been honest that he hadn’t really cared which way, Dean can tell. But he’d been most thrilled that he’d been high-level, since he’d told Dean that now they could share important information--not sex stuff, he’d hastened to clarify, but like, relationship tips and things. Because apparently, he’d read off the Novak website on some page called Getting To Know Your Orientation! that being a Dom or Sub or Switch just tells you what you need. The level tells you how intensely and deeply you need it, and high-level Dominants and Submissives almost always find happy lives in 24/7 total power exchange contracts and relationships. Preferably long-term or permanent.

Dean doesn’t know exactly what that is, but it sounds like hell. He got Sam off the subject by asking about his training classes and school, but it kept nagging at him. Even his enema didn’t relax him all the way, and then Sir was busy with some important contract at bedtime, and left him in chastity to go to sleep alone.

Sir would probably tell him 24/7 is a sublime expression of his Submissive nature or some shit, he thinks grimly, as he shaves, moody and irritated with the whole world. Then he realizes his chastity cage is still on, and he’s gotta sit to pee.

“FUCK!” He slams his hand into the counter.

“Dean.” The warning is mild but unmistakable, from the other room.

“Fuck,” he says more quietly, sitting on the toilet, and doesn’t hit anything this time.

When he slumps out of the bathroom, Sir is sitting in the chair he seems to like best, and there’s a pillow at his feet. Sir points to it, and Dean barely resists rolling his eyes. Yeah, he can figure it out, thanks. He goes to his knees at Sir’s feet. Only, apparently Sir was busy while Dean was showering, because he gets the leather wrist restraints and fastens them on without a word, clipping them together, and then sitting back. Dean shifts on his knees, a little uneasy, suddenly.

“Now that I’ve had time to get to know you a little better, and you’ve become more comfortable here, I’m going to make a few changes to your daily schedule,” Sir starts. “The wonderful thing about private training is that I can devote the great part of my schedule and attention to you, but even so, outside matters will occasionally intervene.”

“That’s all right,” Dean offers. Honestly, he’s still of two minds about the whole sex deal. And he hasn’t been punished recently, that’s a good thing, right?

“It is, because that business is important. But I can tell that over the last days, the change in our level of dynamic interaction has had an effect on you, and not in a good way. You simply have not been Dominated as regularly as before. So your new schedule will address that.” Sir smiles at him, and it’s gentle and scary all at the same time, it’s the means-business smile.

“Uh.” He shifts on his knees again. The hot, soft, wanting place in his belly starts aching, just a little.

“Just listen for now, sweetheart. Morning sex does not seem to suit our schedule, so that will only be on occasion and when I desire it especially. But every morning after your shower, you will bring this paddle,” he holds up a rounded, wooden thing from the end table, flat on one side, nobby on the other, “and the switch to this pillow, and you will kneel and wait. You will ask me to help you begin your day of Submission properly, and to use a firm hand, so that you know how much I care for you. When I accept, you will kneel on the spanking bench for your morning warming.”

Dean’s teeth are grinding together already. The wrist restraints are really helping, actually. They’re reminding him to take a deep breath, and then another one. To count to fucking ten, to not just lash out because he’s mad and fucking scared, because this doesn’t seem fair at all, to get punished first thing in the morning before he’s even had a chance to fuck up? And to have to ask for it, like he wants it?

Sir ducks down and looks into his eyes. “I can see this is a struggle, baby. You’re doing very well,” he praises, and it helps. It’s soothing, calming. Sir knows he’s trying, here, can see it’s not easy. The next breath comes easier.

“Thank you, Sir,” he says, and it’s almost polite.

“The paddling isn’t a punishment, Dean, and it won’t be severe. You’ll get ten strokes on your bottom, and the switch is only there to reinforce the rules, and will only be used if needed. Once you’re done, we’ll go do your blood test and have breakfast as usual. Then Krav Maga, and on the days we don’t train, I’ve spoken with Cole. He’s agreed to run and visit the weight room with you on those days, and also do shorter runs and workouts after we train if you would like.”

Dean glances up at him, warily pleased. The earlier rush of agitation is wearing away, and the idea of running regularly, working out, definitely appeals.

“I can see you need increased activity. You’re ridiculously fit, and need to move. So no more rest hour, during the day.” Sir grins at him.

“Yes, sir.” That sounds awesome. He’d honestly been pretty bored, resting so much.

“For an hour before lunch, you will kneel with me. I may give you something to read, or we might just talk about your Submission, your body, Dominance, anything I think you should know or that you are curious about.”

“You’re making me go back to school? Siiiir,” Dean groans.

“Clearly, the schooling system failed you abjectly, and your classmates as well. Those poor souls are out wandering, but you, I can do something about.

“After lunch, our training time will continue. You’ve done extremely well with your positions, I’m deeply impressed. You move between them like someone who has been practicing for years, and it’s beautiful to watch.” Dean grins helplessly at the praise, twisting his fingers together. “We’ll start some High Protocol, because I find it beautiful and I think you’ll enjoy the challenge. And continue to explore kinks and fetishes, of course.”

Dean resolves to ask about High Protocol as soon as possible. He has a vague impression of period dramas with Subs in elaborate makeup and stiff gowns floating through rooms and sinking down flat onto the floor when their Dominants even peeked into the room.

“Do I still have free time?” He ventures to ask.

“Yes, but shortened. We will do sexual play in the common areas every day. I enjoy your exhibitionism, and definitely want to encourage that.” Sir is smiling at him again, and now it has a wicked edge, and Dean’s face is getting hot. “After all, you are still unable to reach orgasm anally. We have to get that fixed immediately, so that your penis can become a no-touch zone that much more quickly.”

Dean’s bound hands drop to shield his cock protectively, and Sir laughs. “Don’t worry. I won’t lock it up permanently. It’s too important for me to be able to see what arouses you, and what makes you soft. You’ll have your free time, too, and then meet with Benny, and then bedtime. I want you on the pillow with your paddle and switch at 10:30, and you will ask me to end your day of Submission properly. Then you will place yourself on the bed, in Present. I’ll take care to schedule my business during the morning and afternoon whenever I can, so we can be sure to reinforce our dynamic every evening, now that I have seen how unsettled it makes you to go unused.”

Now Dean’s squirming hard. It’s not true. It isn’t.

“Sir,” he complains. Even in his own ears, it sounds like a whine. “I don’t need that. It’s not, it hurts.” Even admitting that feels like a weakness.

“I know, baby. But your body eases to it beautifully and naturally. I know you aren’t a masochist, Dean. But there are pleasures besides the physical, and I’ve seen you experience them when I use you.” Sir cups his chin and raises his face. He looks tender. “I’m very careful with you, with lubricant and a great deal of restraint. If I were truly trying to cause you pain, it would be quite different. And it’s clear you do need it. I think it’s time for the dishonesty with yourself about this to begin to come to an end. Why don’t you ask me to start your day properly.”

He places the paddle and switch on Dean’s pillow, right in front of his knees.

Dean stares at them, arms flexing against the wrist restraints absently.

“Dean,” Sir warns, in the voice that means his patience is nearing its limit.

“Guess you should paddle me to help me be Submissive,” Dean says, sullenly.

“I’m going to give you another chance, since this is the first time. Ask me to begin your day of Submission properly, with a firm hand and a paddle, so you feel how much I care for you.”

Dean scowls and twists the wrist bindings against each other. Fuck! It’s humiliating to ask for a paddling like this! “Tell me one more time?” he asks, stalling. “Didn’t quite get that.”

Sir looks at him levelly, and then sighs. “All right, sweetheart. I didn’t realize you needed correction before your paddling, but clearly, you do.” His hand is on Dean’s neck before Dean can even blink. “Head down, ass up.”

“No!” That wasn’t what Dean meant at all! He wanted no paddling, not a whipping too! He tries to pull back, but Sir isn’t budging, and he has the switch already in his hand.

“You will take three with the switch for bratting. There are more polite ways to get my attention. Now, Dean.”

Defiant, Dean slides his legs all the way out, going down flat on his belly on the floor. Sir still has a hand on his neck and he can’t get any leverage and get up, but damned if he’ll make this easy on him!

“My goodness, Dean.” Sir sounds...amused? “I certainly wasn’t planning to punish you flat. It’s so much more painful. But if you insist.” Wait.

“Wait! Wait!” Dean didn’t mean it! But Sir has a knee pinning the back of his thigh, he’s looming over him, and it’s too late. The first strike smacks down and Dean squeals and kicks, it is more painful, the bite so sharp and deeper without tensed curved muscles underneath.

“No! No no no I’m sorry, I’ll ask nicely! Sir I’m sorry!” He wails as the second hit lands, then the third, “OW! Sir! I’m sorry!”

“Mind your manners,” Sir says sternly, and takes his weight away. Dean sniffles into the pillow. It wasn’t enough to really take him apart, but he does feel sorry, and regretful, and his butt is burning, and when Sir urges him back up to kneeling, he goes quickly.

“Let’s try that one more time. Properly,” Sir commands. The switch is across his knees. It has Dean’s full attention.

Clearing his tight throat, Dean pulls himself together. “Please...um. Please begin my day of Submission the right way, please paddle me with a firm hand, s-so I can feel how much you care for me.” To his horror, he feels tears well in his eyes. To his even greater horror, the words sound true. It does feel like Sir cares about him when he corrects him. It feels like he wants good things for Dean, for him to be happy and secure, like the rules mean something and Dean means something, something important enough to enforce and support.

“Of course I will, sweetheart.” Sir’s voice is all soft and tender now. He sets the switch aside and strokes Dean’s face with a gentle hand. “Let’s get you up on the spanking bench. Just ten, and then you’re done, and we’ll go have breakfast.”

“Okay,” Dean mumbles. The spanking bench isn’t his favorite thing. It’s hard, it has no give, so there’s nowhere to squirm away. Sir helps him up, knees on the steps, his thighs outside the braces that keep his legs spread so wide, cock and balls hanging below him, the body support tipping his head to the floor and lifting his ass up towards the ceiling. He grips the hand-holds hard.

“I will not decrease the count because of your whipping,” Sir warns behind him. “But this is not punishment, remember. If you behave yourself before, it will not be heavy or harsh. It will give you a nice rosy, tender bottom to carry with you into your morning activities.”

“Yes, sir,” Dean sniffles. In hindsight, it maybe wasn’t such a good idea to kick up such a fuss before.

The crack of the paddle is flat, not sharp, and while he can feel the slap of impact against skin and flesh, without the throb of fresh welts under it, Dean thinks it wouldn’t hurt too bad. Over the welts, it seems unbearable. He howls his distress into the bench as Sir lays down five firm smacks on the highest round of one cheek, then five on the other.

“Good boy,” Sir praises him after the last one. “That’s very good, Dean, you’re all done.” He rubs the heel of his palm over Dean’s tailbone, soothing. “Take a few deep breaths, baby. Good boy.” His voice makes the pain ease, makes the burning melt into something warmer, and Dean eases off the bench when he’s urged. Sir wipes his face and tells him he’s good again.

As he walks behind Sir to breakfast, just behind his left shoulder, Dean realizes with a shock that he feels awesome. His butt hurts like fire, but his head is clear, his bad temper is all gone, he’s kind of calm and settled in himself again, like the ground’s steady under his feet. Even the chastity cage feels okay, normal, not something to worry too much about.

Well, shit.

***

Dean hadn’t wanted to choose either pet play or bondage; he’d much rather just keep going with dresses and body jewels. But Sir had insisted, and now he’s on all fours in the room with the leashes and toys on the walls, a jingly collar around his neck, paw-gloves on his hands and pads on his knees.

He’d promised to give it a try. He’s trying.

“Come here, puppy,” Sir pats his leg, coaxing. Dean crawls to him dutifully and sits back on his haunches, takes the piece of chocolate Sir holds out to him and eats it. It’s pretty good.

Now that he’s been here for a while, getting down on hands and knees and wearing a collar and leash hadn’t been hard, but he doesn’t feel anything like a dog. Sir had given him a belly rub, which had felt awesome. He’d put him in a wire crate, which had freaked him out until he’d realized he could bust the lock in about a half-second, and then it had been okay, kind of restful. He’d had to drink from a water bowl on the floor, which had been annoying and messy. And dog toys? Super boring.

Sir looks at his face, and chuckles a little.

“All right, Dean. Kneel up. Experiment over.”

With a huge sigh of relief, Dean does, holding up his hands to be freed from the annoying mitts.

“So, now you know,” Sir tells him. “If a Dominant approaches you to discuss a contract, and high on their list is a desire for a happy puppy-boy, you will definitely not be a good fit. You can take off the knee-pads. Thank you for giving it a good-faith try.”

Dean grins at him, and hops to his feet, shedding the knee pads cheerfully.

“I really don’t get this one. It’s boring as hell, Sir. Do people actually like this?”

“They absolutely do. And don’t get judgemental, Dean. Plenty of Submissives would find it equally tedious to be dressed up in the opposite gender’s clothing. For some Subs, pet play is incredibly fulfilling, an innocent and restful headspace, and a way to interact with their Dominant from a whole new perspective.” Sir is unbuckling the dog collar, and setting away the toys.

“Dump the water bowl, please. So, tomorrow, you will choose between bondage and age play.” He says it so casually, like it’s no big deal. Like both of those things don’t make Dean want to dive back into the puppy crate and hide.

“Sir,” he protests, cringing, then stops.

Sir looks at him sharply, and then crooks a finger, and leads him out of the pet room. He puts Dean down on his knees in Wait, at his feet, while he sits.

“Charlie is coming today,” he starts, and Dean looks at him curiously. Where is this coming from? He knows that. There’s gonna be another sub here, and Dean hopes she’s cool. He’s kind of looking forward to meeting her.

“She is not only a Submissive, but also a member of my staff while she is here. I expect you to keep this in mind, Dean. You will likely see her and Meg interacting in their dynamic while she is here, but you will maintain the respect due to all staff while you are under this roof.”

Dean gapes at him.

“Sir! Of course I will! I mean, I’d never disrespect her, or any Submissive, because Meg might punish her, or she’ll be submitting, or whatever that means...of course I won’t!”

Sir cocks an eyebrow at him.

“Your own Submission and the practice of it is clearly something you are ashamed of, unwilling to embrace, and find demeaning. Why would it be different for another Submissive here in the house?”

The words fall like stones. Dean is struck dumb. He stares at Sir, mouth still open. The silence stretches on, and on.

“That’s different…” he finally tries, weakly.

“How?” Sir’s question is swift and sharp.

Dean squirms, desperately uncomfortable. “I’m supposed to be strong,” he finally mutters.

“So other Submissives are weak?” Sir is merciless.

“No! That’s not what I meant!” Dean cries, breaking position, his hands clenching together, then fisting, then rubbing at his neck and finally twisting together in his lap again.

“What did you mean? Because surely, you would not say someone eating when they are hungry is weak. But Submitting because your nature demands it, just as your body requires food, that is somehow different? Embracing your dynamic and sexuality in all its facets, something that will bring you balance and health and happiness, is shameful? ” Sir reaches down and puts his hands on Dean’s shoulders, pulls him close to his knees, and Dean goes gratefully, falling forward until he can rest there.

“It’s...I never used to think about it like that,” he confesses against Sir’s leg, hiding his face, he’s shivering a little, this is so hard. “I tried not to think about it at all.”

“I know.” Sir strokes his hair slowly. “But this is important, Dean. And I will not shy away from the aspects that make you uncomfortable. We will work through it together, all right? Tomorrow you will choose between bondage and age play. And we will move through all of the fetishes eventually.”

“Yes sir,” Dean says, with a sigh.

“My good boy. Now go wash your face. Charlie should be arriving soon, and we’ll greet her at the door. She likes a formal greeting to get her settled into her role in the house, which Meg and I are happy to oblige her with, and you may observe quietly.”

“Okay. What’s a formal greeting? She doesn’t just come in? I mean, take her clothes off and come in, I guess, here.” Cold water feels good on his hot face.

Sir chuckles. “No, not exactly. The Submissive is escorted to the door, and presents herself silently at the entrance to the home. Her escort--Crowley, in this case--will speak for her, requesting she be granted the hospitality, shelter and protection of the Dominant of the house. It’s a little piece of High Protocol. Sort of like a dance, it’s a way to draw a boundary between her time purely as an employee, and when she is here as a Submissive as well.”

“Whoa.” Dean thinks that sounds kind of intense, but also interesting. He hopes this Charlie person isn’t completely stiff and a stickler for the rules. But she’s married to another Submissive...surely there’s some fun and rebelliousness in there somewhere?

Chapter Text

Castiel stands at the inside entrance, relaxed, Meg a few steps behind and Dean practically vibrating, kneeling on a pillow off to the side. Crowley’s already at the door of the town car, leaning down and murmuring into the open door.

Crowley stands with a chain lead in his hand, and helps Charlie, nude, with her hair bound up in a formal knot, out of the car. He leads her up the stairs, and in through the first set of doors, where she sinks with perfect grace into full obeisance. Crowley drops the chain and steps aside.

“This Submissive requests entry into your home, Dominant Novak,” Crowley states. “She most humbly places herself into your protection and begs your hospitality, if so granted. She acknowledges your Dominance and will submit herself to your rules and your protocols, and will gratefully accept your punishment and correction if she should stray therefrom.”

Castiel nods, and steps forward. He walks once around Charlie.

“Present,” he snaps, and her hips slide up, thighs parting, head down. He walks behind her and slides a finger ceremonially from top to bottom of her crack, then stands straight and walks back to the door.

“I find this Submissive pleasing in her deportment, in good health, in acknowledgement of my Dominance, and in good standing with my rules and protocols. I grant her my hospitality and the protection of this house.”

He grins a little, inside. Charlie looks fantastic, and it looks like she’s gotten another tattoo!

“This Submissive requests the guiding hand, Dominant care, and control, of Dominant Meg Masters, while in this house,” Crowley continues, and Meg steps forward, the next in the dance. Castiel glances back. Dean’s eyes are just about the size of saucers, and he’s leaning forward so far Castiel’s worried he might just tip right off the pillow.

He tunes back in in time to see Meg, her own ceremonial inspection and acceptance complete, remove the chain collar and lead from Charlie, and place her own black leather collar and leash around her throat. Keeping hold of the lead, she steps back a pace.

“Stand,” she says firmly, and Charlie rises to her feet. Her eyes are sparkling, though her face is appropriately solemn. Meg unclips the leash, leaving the collar in place. “Welcome, Charlie. Release.”

As if a spell has lifted, Charlie claps her hands, and Castiel immediately steps forward for his hug.

“Thank you, Fergus,” and she drops Crowley a little curtsey that he returns with a bow before disappearing back into the house. “Boss!” She flings her arms around his neck. “You’re a sight for sore eyes!”

“Charlie, you look fantastic. It’s been far too long. It’s such a delight to have you here, always.” He embraces her warmly, then waits as Meg gestures her inside. “This is Dean, my Submissive in training. Dean, you may get up now.”

Dean scrambles to his feet and Castiel goes to him, placing a firm hand on his waist. He knows the boy has a million questions--he can practically see them spinning--but now is not the time.

“Hi Dean.” She beams at him and holds out her hand, and he takes it. All of a sudden it’s like he dons a second skin, and he’s cocky, grinning, head tilted just so.

“Hey there, Charlie. I gotta say, that was pretty badass, right there. I’ve never seen anything like it.”

“Why shucks,” Charlie giggles, “You’ll make a girl blush with all that.”

“And that’s enough for now,” Meg steps up beside her, reaching for her hair and pulling out the fastener. Bright red locks tumble down. “Kitten, down.” With a little sigh of what sounds like relief, Charlie sinks to the floor, with a murmured “Yes, ma’am.” “We’re going to the training room to make sure the little miss here is very clear on what I expect of her for the next three days. She’ll be ready for work in the morning, Boss.”

Castiel grins and nods at her. Dean gapes.

“You may crawl,” Meg informs Charlie, clipping her leash back on, and leads her out without further ceremony.

“They’ll join us for dinner,” Castiel tells Dean, who’s watching them go. “Both Meg and Charlie enjoy being in public in role like they are.”

“Lucky us,” Dean says absently, and Castiel feels a sudden hot flare of--not jealousy, that would be completely inappropriate and unethical towards a Trainee Submissive, of course--but possessiveness. Completely normal and expected, from any Dominant whose Submissive’s eyes are wandering.

“Dean,” he says sharply, and finds himself pleased when green eyes snap back to him instantly. “I would be remiss in my duties as your trainer not to tell you that, if you were to flirt and stare in such a way while the Submissive of another Dominant, you would find yourself in a great deal of trouble, very quickly.” He takes a step closer to the boy. “And even I find myself...unamused.”

Dean swallows hard, but his cheeks go a little pink and the corner of his mouth kicks up, like he’s pleased? Is the boy mad? Does he enjoy being in trouble?

“Sorry, sir,” he says, and it almost sounds sincere. “Old habits, I guess.”

“Break them,” Castiel advises, and leads him to the staircase. “I want you to go to our bedroom and choose a pretty dress, one that you will like wearing. Put it on, with no bra or panties, and take the red case from the bureau by the door. Meet me in the television room in ten minutes. Quickly, Dean.”

Curious and slightly flustered, Dean jogs up the stairs, and is back down and standing in front of Castiel, shifting a little from foot to bare foot, well within the time given. He’s lovely in pale gray with a subtle lace pattern, low-scoop neck and a knee-length skirt.

“You’re not in trouble,” Castiel lets him off the hook immediately. He takes the bag, and smiles up at Dean, reinforcing the message. “Lift your skirt for me, honey. I’m going to take your cage off for a little while.”

It’s the work of moments to remove the cage, but Castiel lingers, enjoying the incredible smoothness of hairless skin, the little shudders that rock through Dean’s leg muscles as he strokes the warm silky shaft and lets his fingers play. As he’d expected, Castiel working under Dean’s skirt like this has the boy dark eyed and breathing deep, his cock hardening in quick little jerks, far more quickly than if he’d been standing naked.

“There,” he finally says, sitting back and tugging the skirt free of Dean’s white-knuckled grip. “Now come sit with me on the couch, and we’ll look in my bag together. There are some toys there that you’ll get to know very well.”

“Yes, Sir,” Dean says, red-cheeked, his erection visibly interrupting the line of his skirt.

“These are all yours,” Castiel informs him. “Everything in this case was ordered for you specifically, so everything should be the right size and shape. Now let’s see.” He opens the bag, and Dean cranes to see.

“Here are some plugs. I prefer you nice and tight, so we probably won’t be using these much.” He sets them aside. “An anal hook, these are lovely for when I prefer to keep you restrained by something a bit more creative than your wrists…” the elegant toy is a long rod of cool stainless steel, curved beautifully, with a large ring on one end that would rest in the small of Dean’s back above his crack, and a sizeable silver ball on the other, angled sharply inwards. Dean’s breath catches.

“That...oh my god,” Dean says, weakly, staring at it.

“I like it too,” Castiel agrees. “But today I’m looking for something a bit more active. Ah.” He pulls out a dark blue vibrator, smooth on the inner curve and deeply ridged on the outer. He holds it up to show Dean, flicks it on with the control on the base, and it hums to life, vibrating hard.

“You’re gonna put that in me?” Dean’s voice has gone a little high and squeaky, and all of Castiel’s Dominant instincts flare into warmth. He’s not protesting, he’s not fighting, he’s nervous but not closed off. In fact, he’s still leaning forward a little, obviously fascinated.

“I told you, we’re going to work on your anal orgasms,” Castiel says, setting the bag aside for now. “Now, slide up on the couch, pretty boy, get comfy on the pillows. On your back, spread your knees, open yourself up for me.”

“I didn’t think we were going to start today,” Dean complains a little, even as he’s moving. He’s still not used to moving in the dress and it gets stuck under his hips, trapping him, but he pulls it free and then turns sideways, leaning against the arm of the couch, supported by the pillows. His knees are up, the skirt draped over them, and Castiel can see underneath it, the soft curve of his balls, a hint of his hard cock, and then his thighs nervously squeezing together.

“Does the skirt make you shy?” He gets closer, almost between Dean’s feet, and runs a gentle hand up Dean’s leg, then down his inner thigh, urging it to fall outward. “It’s different, isn’t it, when there’s clothing and I’m still touching you under it? Tell me.”

Dean nods, chewing his lower lip, his cheeks red and his eyes very bright. “It’s. It feels dirty-sexy. Good, though. I can’t see your hand but I can feel it.”

Castiel chuckles. “Now, I want you to keep your hands on your knees, or behind your back if you think you won’t be able to control them. The only place you’re going to get stimulation is inside, and I want you to focus very hard on that.” He squeezes some lube onto the vibrator, then nudges the slick tip of it into the shadowed space beneath Dean’s sac. “Spread your legs, Dean. When I tell you to open for me, I expect obedience.”

Dean’s thighs spread reluctantly wider. When he looks, Dean is craning his head, trying to see what Castiel is doing.

His tight, puckered little hole furls open around the vibrator at Castiel’s firm pressure, and at this angle, it’s gorgeous to see all the little muscles in his groin and inner thighs twitch and clench and release, reaction to the intrusion as he fights to adjust.

“God,” Dean gasps, and Castiel sees the skirt move, a sure sign that Dean’s hands are clenching. “Sir, that’s...oh it burns but, oh my god, Sir.”

“It’s designed to fit inside you,” Castiel murmurs, as he inserts it fully. He rests it for a moment, letting Dean breathe, and then strokes his thumb over the sleek warm dampness of Dean’s perineum. “I want you to concentrate here. Work your sweet spots against the vibrator, and make yourself feel good.” He sits back up, but leaves his hand cupping Dean, fingers just under his cheeks, heel of his palm right where he’ll be able to feel Dean obey his order and contract his inner muscles.

Dean already looks wrecked. Laying back against the cushions, his legs raised and spread and draped with his skirt, his face flushed and lips bitten red, he could be from an old-fashioned pinup calendar.

“I don’t know how to just squeeze those muscles,” he complains, and shifts his hips fretfully. “Oh!”

“Those are the ones,” Castiel encourages, having felt the movement under his hand. “Again.”

A tentative squeeze pushes the base of the vibrator against his fingers. Dean’s mouth drops open on a sigh. The ridges on the outer curve will allow his muscles purchase, Castiel knows, while the smooth lower surface will be a delicious frustration.

It is dirty-hot, he decides, as Dean starts to work. His hand disappears under Dean’s skirt, and to any watching eyes, he could be fingering him, or teasing his cock, or any number of things. And when Dean’s hips rock, Castiel stills him.

“Ah ah ah,” he warns. “Inside muscles only.”

Dean groans, staring at him.

“That’s...I’m pretty sure that’s unconstitutional, Sir.” He’s breathless already, and Castiel can feel him clench despite his protests.

“Really? I never learned the amendment regarding hip movements!” Castiel grins at him. “Inside muscles only. Bear down, baby, squeeze and release. Use your muscles to milk the vibrator. I know you can do this.”

“I’m not so sure,” Dean despairs, and there’s a sheen of sweat on his face, the space between his legs is humid and hot, but he’s trying, and he tries again.

“Maybe in violation of the Geneva Convention?” Dean tries, and throws his head back against the arm of the couch, eyes snapping closed as he finally finds the right muscles to work together. Castiel can feel the rhythmic pulse of the vibrator, pulling and returning, against his testing fingers. Dean’s hands are white-knuckled fists on his knees, and there’s a fine tremor starting in the big muscles of his thighs.

“Who’s violating the Geneva Convention? Can we sue?” Charlie looks like she’s walking very gingerly, which makes sense given the slim black leather belt circling her hips and cinched between her legs. There’s clearly at least one insertable locked inside her, but her smile when Castiel meets her eyes is bright and irrepressible.

“Charlie,” he smiles back. “I thought Meg would certainly still have you occupied?”

“She said it was too close to dinnertime, and she didn’t want to start something we wouldn’t have time to finish. Right after that, though, we have all evening together.” She touches the belt with careful fingers as she eases herself into the chair beside him. “She said this was a hint, but I stopped trying to anticipate her plans a while ago. Hey, Dean!”

Dean blinks dazed eyes at her, and Castiel thumbs the vibrator to the lowest, silent setting, and he shivers all over with a moan. “H-hi Charlie,” he gets out, thin and strained.

“Dean’s learning to orgasm anally,” Castiel says casually. “Lift your skirt, sweetheart. Show Charlie how hard you’re working.”

“I can’t,” Dean whimpers, even as his hands shakily raise the fabric of the skirt up, baring his lifted knees and his lower body. His stiff, red cock twitches hard against his belly; oh yes, Castiel thinks, exhibitionist indeed, my boy.

“Oooh, and on his back, too, not even any leverage,” Charlie winces sympathetically. “Well, but at least you have a prostate! Let me tell you, it’s not easy at all to drive yourself to a g-spot orgasm through the totally wrong entrance.”

“You persevered,” Castiel notes blandly. “It was character-building.”

“It was hell,” she counters with feeling, and Dean actually struggles up from his sprawl.

“Wait, Charlie, Sir, you were a Trainee Submissive here? Like me?” He’s obviously struggling to get his brain online, the vibrator no longer pulses against Castiel’s hand, and he’s let his skirt fall.

“No, not in the same way,” Castiel answers, and then grabs a pinch of soft, loose skin on Dean’s sac and *twists.*

Dean squeals, high and thin and shocked, and twists his whole pelvis up and away, his hands fluttering in the air, whole face drawn with the sudden snap of pain.

“You were told to lift your skirt, and told to focus on your hole,” Castiel snaps. “Both of those commands are still in place. Your attention must be on your Dominant and obedience. I will not be so lenient with the next distraction.”

“Yessir!” Dean gasps and yanks his skirt back up, and Castiel’s reminder takes instant effect. Every part of Dean is now angled towards him, his eyes, his energy, his attention. His neck has softened and bowed a little, and the muscles in his ass immediately start working at the vibrator again.

“Good boy,” he praises, and watches Dean’s eyes glaze a little more, and turns back to meet Charlie’s amusement.

“What if he can’t come before dinnertime?” she asks, and he rolls his eyes at her. She knows very well, and she’s just asking for Dean’s benefit, but he’ll indulge her.

“I will ice him down and place him back in chastity. He will get there eventually, all Submissives can. It’s simply a matter of correct...motivation.”

“Oh god...please…” Dean’s voice is a thread of sound. His eyes fall closed again.

Charlie laughs a little. “I actually came to find you to ask a favor. Can I borrow Dean for a couple of hours tomorrow? We need to move some equipment around, and usually Ash and I are fine, but he hurt his wrist and we could use some extra hands.”

Castiel thinks about it. “I believe so. That should be fine. Just let me know when you might need the assistance, and I’ll rearrange his schedule to accommodate.”

Charlie gives him two excited thumbs up. “Awesome. Thanks! I’m pretty psyched to meet him when he’s not quite so busy, and I’m a little more in my head, too. Speaking of which, I’m gonna go unpack so I can have a clean slate tonight. Thanks Boss. Bye Dean! Good luck!” Still walking carefully, she’s gone, and Castiel can return his full attention to Dean.

The boy is suffering, now. His legs are shaking, and every breath trembles in and out in small pants. He’s still keeping his skirt bunched above his knees, and in the light Castiel can see the blood-dark hardness of his cock, wet-looking as it arches against his belly. But he has clearly turned all that powerful will inwards. Muscles ripple against Castiel’s hand and his hole is nursing at the vibrator like a little mouth, pulling at it rhythmically, trying to draw it in deeper, then releasing it. Dean is grinding it against his own Angel gland and prostate, Castiel knows, over and over.

“You’re doing so well,” he praises Dean. “You’re doing perfectly. That’s exactly right, sweetheart, you’ve got it. Find what feels best, and see if you can do it again.” He presses the heel of his hand gently against Dean’s perineum, giving him just a little firmness to brace against.

“Oh. Oh.” Dean’s eyes fly open and he freezes, everything going still in an instant. The vibrator still shivers gently against Castiel’s fingers, but other than that the only movement is the sluggish pulse of come as it moves up the big vessel on the underside of Dean’s cock, then ejaculates weakly, two small spurts onto his belly.

“You did it. You made it happen.” Quickly, Castiel turns the vibrator off. He leaves it in place for just a moment, but as Dean just lies still and breathes, he draws it out gently, wipes it clean, and sets it aside. “That was so good. I’m so proud of you.” He smooths his hands up and down Dean’s thighs softly, gentling him.

“It didn’t feel as good as I thought it would,” Dean says, bewildered. He blows out a breath and looks at Castiel. “It felt like it was gonna be amazing and then it wasn’t.”

“Well, to be fair, the first time you masturbated by stroking yourself, you probably didn’t get it just right either,” Castiel points out with a grin. “Maybe you stopped too soon, and you need to work the vibrator all the way through.”

“Or maybe I sprained my ass,” Dean suggests, with a wince as he shifts a little.

“Doubtful. Don’t forget, your body was made to do this. I could use you three times a day, and you wouldn’t lose elasticity, wouldn’t become strained or overstretched.” He drifts his hands down, thumbs Dean’s hole, and thrills at the wet, soft give that instantly sucks him in. He pulls down on the rim a little, and drinks in Dean’s squirm and whimper.

“You’re saying my butt is magical?” Dean sounds skeptical, if breathless.

“Not at all. It probably has to do with supporting structures needed for the Angel gland, but I won’t argue with the side benefits I enjoy.” He presses the rim a little more open, feels it cling and pull, lets it drag shut and tighten around his thumb again, close and hot.

“Sir,” Dean whines again, squirming harder.

“All right. You’ve been so good, I won’t tease you. And it’s nearly dinnertime. You’ve made your dress all messy, would you rather wear it to dinner, or be naked?”

Dean barely has to think about it at all.

“Naked, please, Sir.”

“Very polite. And Dean?” He stops Dean, who is already struggling up out of his sprawl and starting to pull at his soiled dress. “You did something new today, something that was difficult and strange, and you did it so well. I’m extremely proud and pleased with you. You worked hard, and listened, and submitted beautifully. You’re a very good boy.”

Slow pleasure rises over Dean’s face like the dawn. For all his sass and snark, Castiel has never had a Submissive react to honest praise more openly and sweetly than Dean does, and finding these moments to give him direct positive reinforcement is becoming something Castiel seeks out more and more. Dean responds like Castiel has stroked his cock, almost shivering with it.

“Thank you, Sir,” he is smiling down to his feet.

“You’re welcome, baby.”

Chapter Text

“Wars or Trek?”

Startled, Dean blinks at Charlie. She’s just watching him with narrowed eyes, with hands still on her hips, she hasn’t moved or changed since Sir left Dean alone with her a few moments ago.

“Uh, Wars, I guess?”

“Who shot first?”

Dean knows this one. “Han,” he says confidently, starting to smile.

“Co-RRECT. Kirk or Picard?”

“Jesus, Kirk,” he says, almost insulted. He’s a Sub, sure, but he’s still a red-blooded American male, thank you very much. She hums a little at that, eyebrow going up consideringly. Then her hand raises and her fingers split in the Vulcan salute.

“If I do this, what do you say?”

“Live long, and prosper,” he replies promptly, now just grinning.

“Okay. We can work together,” she declares, just like that. She waves a hand around the small room, stacked with computer towers and a few large boxes. She, like Dean, is wearing pants and a t-shirt today, suitable for working in, though Meg’s collar still peeks above the neck of the shirt. “All this has to get moved three doors down so I can run new cables, and the AC guys can do the new venting. You up for it, big guy?”

“I was born ready,” Dean declares.

At first it’s all just simple work talk. Move this box here, no, that one goes on top, okay, now grab this one. But they get into a rhythm pretty soon, and he can’t help watching her, itching with curiosity.

“Okay, spit it out,” she finally says, standing up and shoving hair out of her face. “I can see you’re dying to ask me something.”

“Well, it just seems like you know a lot about this place, about Sir,” Dean shrugs, suddenly fascinated by the box he’s taping up. “I mean. I’ve only been here a couple weeks. You know a lot more about him than I do. Maybe he’s got a permanently contracted wife stashed in the attic, I don’t know.”

Charlie snorts.

“Castiel? He doesn’t do long term contracts. He really only even does short-term contracts because he’s so careful to stay healthy so he can do his Training work right.”

“So he’s, what?” Dean finishes one box and starts on another. “Married to his work or something?”

Charlie giggles a little. “He is pretty passionate about it! But nah, he’s a pretty serious sadist.”

“So?” Dean makes gimmee hands and takes the tape back. “Hot guy like him, rich, super nice, super smart, a doctor, there’s gotta be masochist Subs lined up around the block all, ‘please whip the skin right off my ass, Master!’ Doesn’t seem like that would be a problem.”

Charlie looks at him a little pityingly. “Firstly, dude, no, nobody wants their butt-skin whipped all the way off. And second, Cas doesn’t want a masochist. If they’re getting off on it, he’s not. It’s a wiring thing, I guess. Anyway, finding a Submissive who gets satisfaction from real pain without masochism isn’t easy, from what I understand.”

Dean frowns down at his hands. “What do you mean, real pain?”

“Well, there’s plenty of uncomfortable stuff pretty much all Subs do okay with.” Charlie shrugs. “Punishments. Stresses. Rough sex. A lot of that stuff actually helps with subspace and reward triggers, things like that. Real pain is different, though. If a sadist like Castiel is set to give it out, you’d definitely know the difference immediately.”

A few things come together, then. The way Sir always reaches around when he’s fucking him roughly and is so pleased to find Dean soft, the way he reacts when Dean screams. And Dean wonders how much Sir has been holding back. Remembers how he’d told him how different it would be if he was really trying to hurt him, and a deep, hard shiver travels down his spine. The little daredevil voice inside his head is asking if he could handle it. Reminding him of all that intensity. Wondering what it would feel like, without any leashes on it, all aimed right at Dean, and then whispering a thought that Dean might actually be missing out on something great, here.

He shakes it off. “Right, okay, yeah, I see what you’re talking about. That’s the last box, now what?”

“Now we move ‘em. Come on, hot stuff. Tell me all about yourself. Who’s your favorite porn star?”

Over the next hour, Dean discovers that he and Charlie share a taste in soap operas (Dr. Sexy!), porn stars, and mixed drinks. She’s also unsurprisingly supportive of Submissives in the workplace, and knows about all things supernatural.

At that discovery, Dean puts the shelf he’s moving down, sets his hands on his hips, and stares at her, exasperated.

“This shit is supposed to be secret! We spend a huge amount of time and, okay, maybe not money, but effort, to keep things looking reasonable for the public so nobody knows there are werewolves and wendigos out there. And I show up here and there’s rock salt in the foundations and everyone here knows what a protection sigil looks like! What the fuck!”

Charlie grins at him. “I knew even before I got involved with Novak Corp. I mean, the truth is out there, you know? But I kind of let it slip when Cas and I were setting up the LA office, and he already had the whole picture, so that made it easier. None of us are real hunters, though. Not like you are.”

“Were,” Dean corrects, and is a little surprised by the depth of bitterness in his own voice.

Charlie looks at him sideways. “I get that it might be hard,” she says slowly, handing him some shelves. “Hell, probably harder since you’re high-level and probably gonna be in a seriously strict contract. But if there’s one thing I learned over the last couple of years, it’s that not much is impossible.” She shrugs. “I got married. To someone I actually love and want to do sexy sexy things with, and it’s amazing, and we’re both happy and healthy and everyone I knew growing up said that would never happen. So if you’re a hunter, and you wanna keep being one, figure it out. Find a Dominant who’ll help you make it work. Don’t give up so easy.”

Dean stares at her. Jesus. Did she just call him a quitter?

“I don’t know a single Sub hunter,” he tells her bluntly.

“So be the first one,” she raises an eyebrow at him. “Be the baddest ass in the valley of darkness, I dunno. I bet there are some though, and you just don’t know them. I thought there weren’t any Subs running tech for companies, but Castiel hired me and put me in charge and then I found out there are some, it’s just not a lot.”

“Oh.” Dean busies himself with the shelves again. He’s all off-balance again. Everything he learned from his Dad, from what he’s seen and heard, is telling him one thing, and Charlie and Sir and his own hopes, they’re fighting against that. It’s dizzying.

“So tell me about hunting,” Charlie says, sounding eager. “Give me the real nitty-gritty, c’mon. We still gotta set up this new room.”

That, Dean can do.

***

They’re just connecting the last monitor when Sir steps into the room, an hour or so later, and Dean would suspect him of psychic powers except Charlie clearly had a pretty good idea of exactly how long this was all going to take, and kept them moving right along.

“Nice work, you two,” Sir looks around the new computer room approvingly, hands in his dress pants pockets, looking all casual and relaxed. The room is larger and brighter than the old one, and there is more storage, and a window.

Dean beams at the praise, and notices Charlie is too.

“Still have to re-run the wiring in the old space and get the AC work done, but it’s coming right along, boss!” She says, all cheerful. “I’m done with Dean, he was awesome, a huge help.”

“I’m very glad to hear that.” Sir turns that smile on Dean, and Dean melts a little inside. “Since you’re finished, clothes off, Dean, immediately please. Come kneel by me.”

His own eagerness and...relief?...at those words is startling, but Dean shrugs out of the work clothes and folds them roughly, then hurries to Sir’s side and slides down to his knees with alacrity. When Sir’s hand lands in his hair and pulls his head against his thigh, Dean sighs, a tension he hadn’t noticed leaving his neck and shoulders.

He can hear Sir’s rumbling low voice and Charlie’s lighter replies, but he’s too busy basking to notice the words, especially since they’re probably talking about electronics, still.

He tunes back in when Sir tugs gently on his hair.

“Do you need the bathroom, Dean?” Sir is asking him.

He shakes his head no against Sir’s thigh.

“You look good together like that,” Charlie sounds approving.

“He’s a very good boy.” Some warm note in Sir’s voice has Dean looking up, and Sir is looking down at him, and smiling.

“He’s all right. Even if he does prefer Kirk to Picard.”

Sir laughs a little at that. “I still don’t know what that means, but I’ll get him out of your hair now. See you at dinner, my dear. Dean, up, follow.”

Dean casts his mind back over the day as he walks behind Sir back towards their bedroom. Pretty normal, even with the hated morning paddling, which does seem to be helping him feel better even if he doesn’t want to admit it at all. Breakfast and Krav Maga, a little time with Sir learning about how knowingly disobeying a Dominant’s command causes major stress, and then lunch. He’s been working with Charlie ever since. His muscles are pleasantly tired.

“We’re not going to the training room? Sir?” He knows they’ve probably missed most of their regular time, but Sir doesn’t generally skip out on a chance to put Dean through his paces, even if it’s shorter than usual.

“Not today, lovely. I had a long call with our board of directors while you were working with Charlie, and I find I need to release frustration with my Submissive.” He puts a warm hand on Dean’s neck, and ushers him into the bedroom.

Oh, Dean thinks. OH.

“This is an important part of the dynamic,” Sir says calmly, as he guides Dean to the spanking bench and onto it, Dean going without resistance, breathless, unmoored. “Just as a Submissive relies on the Dominant partner to keep them balanced and calm, the Dominant looks to the Submissive for the same. Knees up, honey.”

Sir is raising the knee supports higher, so Dean is almost crouched, ass pressed up and back, legs spread. The wooden spreaders keep his thighs parted so wide, and the air of the room is cool against his hole, his soft cock and balls hanging free below.

“What...what…” he stutters, looking back over his shoulder at Sir, his hands clenching on the holds. His stomach feels hot and yearning. His Sir needs him, needs him to help, Dean can fulfill this need for him. It’s exciting and terrifying and amazing.

“I’m going to whip you, with a flogger, and then a flail, and then fuck you,” Sir says. “Dean, this is not punishment. You are serving a deep need and an important place in your role, and this will be fulfilling to you, as well. I want you to close your eyes, and think about that for me. Take ten deep breaths, thinking of nothing else.”

Obediently, Dean closes his eyes. He can hear the rustling sounds as Sir strips, the little noises of the house around them. The fast hard beat of his own heart. He jumps a little when Sir touches between his shoulder blades, but then relaxes again as the hand strokes down his spine, all the way to his rump, curving over his cheeks, and then repeats the motion. The petting is soothing, drugging, and soon he’s breathing in time with it. Deep inhale, and then slow exhale. He feels his tight muscles slowly loosen and give. This feels right, it feels good. He is here for Sir. He can give Sir this, offer it up. He wants to, so much, a deep, primal craving that he’s only now recognizing.

“Good boy,” Sir murmurs, after what feels like forever. “I’m going to begin now, baby.”

“Yes please,” Dean sighs.

The swish and thud of the flogger against his bottom is new and different. It doesn’t hurt at all, really, just kind of a tingle on his skin and the deeper The tails trail off his skin slowly like a tickle, and then thud down again, in a different spot. He likes it, and squirms a little. Sir gets a rhythm going, both cheeks, then starts on his back, up to his shoulders. It’s like a good massage, and Dean melts into the bench, eyes going half-closed in bliss.

Back to his bottom, and it’s tender now, more sensitive. He jumps a little at the impact, and then Sir starts whipping his thighs. Over and over, back and forth, one then the other, then up to his butt and back down, up and then down, until Dean is rocking with it, easy and loose, feeling as if every muscle has been liquefied.

“So good, Dean,” Sir says clearly. He walks around and leans down to kiss Dean’s mouth, and it’s only then that Dean realizes the flogger has stopped, no more hits are falling. He moans into Sir’s mouth. “You like that, lovely? That’s good to know. What a beautiful boy you are. Now the flail, pretty, this one is much sharper.”

The first strike from the flail is such a shock, after the soothing, heavy comfort of the flogger, Dean arches up right off the bench. It’s thin and stinging and whippy-sharp, hot and nasty on his warm, sensitive skin.

“Down, Dean,” Sir’s voice is stern, and Dean reluctantly resettles himself. The next strike is harder. More painful. He whimpers, his left asscheek starting to burn. Then the right. Then the left again. Then *snap* against his thigh.

“AH OW!” he cries out, unable to stop it, leg trying to jerk forward, prevented by the wood of the bench.

“Good, breathe,” he hears, and he tries, but *snap* against his other thigh and this time his cry is wordless, just a protest of the pain. His eyes and nose are starting to prickle. Every strike lays down many thin lines of fire on his skin, diffuse and sharp and Sir is going faster now. Focusing on his bottom. Dean is really squirming now but there’s nowhere to go. The tears standing in his eyes well up and over as the burn spreads through his bottom and up, overwhelming, and his thighs and down, blinding.

He’s crying openly now, not the raw desperate sobs of punishment, but softer, quieter tears. The pain is building slowly like a wave, and his tears match it. The regular snap-snap-snap of the flail on his skin is like a metronome, every one sending a shudder through him and clenching his hands on the holds. Sir’s breath is coming harder too, he can hear that over his own pants, and it all comes together with his tears and the pain to wrap him in a cocoon that lulls him down and down and down until, strangely, he feels like he’s flying.

“My wonderful boy,” Sir says, and it has that sweet, distant echo sound, oh, Dean has found subspace, it’s why he feels so light even when his tears are still falling, why the fiery pain crackling over the skin of his ass and thighs is more like a caress, for all that it doesn’t feel good. The flail stops and Dean gasps for a deeper breath, heaving air into his lungs and only then realizing that his sobs had wrung him shallow.

Tear-blurred, he sees Sir step around him again, going to the cabinet.

“NO,” he begs, his voice cracking. For the first time, he really struggles, trying to lean up and turn so he can make himself heard. Even in subspace, he knows this is important.

“What is it, sweetheart?” Sir seems to realize this isn’t a normal protest; he pauses and steps back.

“No, no lube,” Dean pleads, voice thick with tears. So many conversations in his head. Sir is holding back, not using him as he wishes to, Dean doesn’t know what it would be like to really be his Submissive, Sir hasn’t even really tried to hurt him once. “Please no, please, just use me, truly, Sir.”

Sir seems frozen. Then there’s a hard hand in Dean’s hair and his head is wrenched back painfully. Sir is staring into his eyes.

“You are asking to be taken dry,” he states, cool and flat and somehow incredulous.

“Please,” Dean whispers through his strained throat. God, he wants it. Wants to know how it feels, know how it’s different from their usual sex. Wants to know how it feels to truly feel Sir in passion, unconstrained. Even the hints he has experienced have left him stunned.

Sir leans closer, and suddenly he looks fierce. Eyes black with just a sliver of blue, face pale, lips thinned and cheekbones drawn sharp with his frown. Dangerous, in a way Dean has never felt, in a way that makes his mouth dry and his pulse kick and the soft edges of subspace start to pull back.

“I would fuck you until you bled,” Sir says, still flat, no longer cool. His voice is a dark rasp, and his hand tightens its hold on Dean’s hair. “Then take you from this breeding bench and whip your hole as you tried to crawl away, just to make you tight again, and never having softened, fuck you again there on the floor. Dig my fingernails into your cock until you lost your voice from screaming, and then bring it back by torturing your breasts. And this is what you ask for.”

Dean’s arms and legs and spine are watery-weak with terror, and he’s blinking too much, too fast. But the part of him that runs into vampire dens alone, that escapes werewolves with a rescued ten-year-old riding piggyback on his shoulders, that once laughed in the face of a yellow-eyed demon, that part of him is practically drooling with desire. He manages a tiny nod against Sir’s fist in his hair.

“Please,” he manages, quiet but clear. Dean has lived most of his life in go-big-or-go-home mode. So why would this be different?

Sir doesn’t blink, just stares at him with those heat-dark eyes for an endless moment. When he finally pulls back, though, he looks like Sir again, face smoothing into its usual impassive lines. Calmer. He lets go of Dean’s hair, and Dean barely keeps his face from smacking down into the bench.

“I will decide when, if ever, that type of scene is something that would be appropriate for you. You will not speak again until you are released from the bench,” Sir tells him, and fetches the lube from the cabinet. Dean, face burning, ass feeling like it’s on fire, is left sobbing against the unforgiving wood.

Sir spreading his cheeks with two firm palms hurts terribly, and Sir punching his cock into Dean, even lubed, shoves a cry out of him that cannot be stopped. But even as he cries out, even as his hips twist and strain to spread further as if that will ease Sir’s entrance into him, he feels like he’s missing something, like this isn’t quite complete. And as the pain washes through him and leaves him hollow and filling back up with that tranquil peace, satisfaction, contentment, he can’t help but wonder if there might be more.

Chapter Text

Castiel watches Dean and it’s a struggle to hide his amusement. In anyone less aggressively masculine, he would have said the boy had spent the whole rest of yesterday pouting; in Dean’s case, it was really more of a sulk. He had obeyed the letter of every law, while scowls and sighs and slumped shoulders indicated his displeasure.

It’s truly a mystery what he was thinking, begging for real sexual pain; even as every desire in Castiel was driving him to accept, his rational brain knew that it was far too much, far too soon, even if Dean might ever reach the point of readiness. After he had finished, and they had both recovered, Castiel had held Dean and had assured him that he was not angry with Dean for requesting more intensity, but that those decisions were the prerogative of the Dominant alone. And that any requests should be made well before a scene began. Still, being denied is clearly not something Dean is best pleased with. And now that they’re back in the training room, Castiel thinks it’s about time to reset his attitude a bit.

“Since you are obviously so far advanced in your training that you are qualified to request advanced activities,” he begins blandly, turning up the lights and opening the skylights as they enter the main training area, “you’ve obviously moved beyond needing the comfort of choice in fetishes. Today, we will do Age Play. I’m sure this won’t be a problem?” He looks at Dean expectantly.

Dean’s face is a picture. Torn between dismay and horror and stubborn will, his mouth opens and closes three times, before his shoulders finally drop.

“No, I guess not.”

“I beg your pardon?” Castiel snaps, and moves to take the switch.

“No it won’t be a problem Sir!” All in one breath and Dean’s standing straight, suddenly, eyes much wider.

“Thank you, that is much more appropriate. I’ve let you have your little tantrum, because your moods are your own, but I will not tolerate disrespect, and I believe I’ve made that more than clear. Now, this is the age play room, as I’m sure you remember.”

Castiel actually likes this play room a great deal. It’s quite comfortable, larger than most, and has a television, a stereo, a small living room set, even a kitchenette and bathroom attached. It could double as a small apartment in a pinch, and as he urges Dean inside and closes the door, he smiles a little at the cheerful bears and balloons painted on the walls.

Dean is standing stiffly in the middle of the room, the scowl back on his face, as Castiel takes one of the soft blankets off the pile by the crib and spreads it on the floor.

“Come here, sweetheart. Sit with me,” he orders gently, sitting crosslegged on the floor, and Dean does, if with a little huff.

“I know this does not appeal to you now, but from what you’ve said, I also realize you may not understand it very well, so this time, we will talk about it a little first, and you can ask any questions, all right?” He reaches out and tips Dean’s chin up, forcing stormy green eyes to meet his own.

“Yessir,” Dean agrees, reluctantly.

“First, age play is not about the Dominant being attracted to children, nor about the Submissive actually becoming a child,” he starts. “That’s quite important, obviously. For all the childlike mindset and attitudes it encourages, the Submissive remains an adult.”

Dean snorts at that. “I knew that much, Sir, unless there’s some kind of crazy magical mojo going on, nobody’s turning Subs back into babies and toddlers.”

“Exactly. So, what this kind of play does is take the concept of caretaking, providing, and protecting--we spoke about this, with hand-feeding--and escalates it to a certain extreme.” Castiel meets Dean’s eyes again, seriously. “For the people who do this, it can be a powerfully fulfilling display of Dominant care on one side, and Submissive surrender and trust on the other. Some find it sexual, and some do not, and that is entirely up to the individuals. But it’s meaningful either way.”

Finally, Dean is looking thoughtful, instead of surly. “Okay, I see that. But why all the...stuff? The toys and books and...diapers,” the last spit out like it’s a swear word. “Baby clothes and everything?”

“Because it’s fun?” Castiel grins at him. “Because it helps the Submissive find an innocent, simple, childlike headspace, where they can release adult pressures and worries for a time. The clothes, the diapers, the toys, all help shed the habits of adulthood and return to childhood pleasures, even if temporarily, and trust that their Dominant will protect and care for them.”

Dean gives the building blocks a judgemental side-eye. “I was field-stripping M-15s when I was ten years old, not playing with blocks.”

Castiel nods, careful to show no pity or even sympathy. “And if my previous experience is any guide, that means you will either have no affinity for this at all, or you will enjoy and benefit from it very much. And Dean? If it does work for you, you should know that little boys have different rules. It would be far too harsh to whip them; they get corner time, or perhaps a spanking for bad behavior. The rest we can work out as we go.”

He grins as Dean perks up at the change in punishment protocol, and stands, going to the changing table to gather some things.

“We will start slowly, today,” he keeps talking to Dean. “You will wear the diaper, but I won’t expect you to use it. You can ask me anything, no language restrictions besides speaking respectfully. You may play with any of the toys and read the books, and choose the music. Just relax and enjoy the room, if you can. Try to let go of the big concerns you have, just for a short time.”

He hopes that if he remains as matter-of-fact as possible about the whole thing, Dean will simply go along with that, and so far, it seems to be working.

“Come here please. Up on the table, let’s get you ready. Would you like something to hold while we get your diaper on?”

Dean’s jaw is working, but his hands aren’t in fists. He’s tense, but not lashing out.

“Something to hold like what?” He approaches warily. Castiel pulls a large stuffed tiger off the shelf above the table, and offers it out.

“Go get ‘em, tiger?” he attempts.

Dean actually barks a laugh at that, a genuine one, his tense shoulders easing a fraction.

“That is just. Super lame, Sir,” but he’s smiling, and taking Castiel’s offered hand to step onto the stool and get up on the table. He also hasn’t let go of the tiger.

“I know this is used for humiliation, at times, but in this kind of play, it’s not meant to be so,” he keeps narrating, as he gets Dean settled. “In fact, for those who enjoy age play like this, diaper discipline can’t really be used anymore, as it would be a shame for it to be associated with anything negative. Here, hips up.”

Stiff, with his face turned away, Dean complies. He’s got the toy tiger practically strangled to death in his hands. Deftly, Castiel slides the adult diaper under his hips. “Back down. Just some powder to prevent chafing and we’re done.” Dean’s belly jumps as the he rubs the silky powder into every crevice, and then gently brings the front panel up between his legs, and fastens the tabs, making sure the diaper is snug around Dean’s waist.

“There. Not so bad?”

Dean blows his breath out through his teeth. He’s staring at the ceiling now, still strangling the tiger, but he’s much more relaxed. Even his breathing is slower and deeper.

“Soldiers in the military sometimes use these when they’re out in the field,” he informs Castiel suddenly, like it’s important Castiel knows. “So they’re used by regular adults too.”

“Of course,” Castiel agrees. “They’re made for adults, meant for them. It fits you nicely. Now, do you want to go choose some music? Anything you like, just keep the volume reasonable.” He tugs Dean up to a sitting position, then eases him off the changing table. Before getting him down, though, he makes sure to catch Dean’s eyes.

“Just like with the puppy play, Dean. All I’m asking is that you try. If this does nothing at all for you, we will move along to the next thing, as long as you’ve made an effort. All right?”

Dean gives him a little smile. He doesn’t seem upset, actually. A little resigned, kind of interested in the stereo, but not upset. Between the challenge he’d thrown down at the beginning, and keeping it private today, Castiel has derailed his resistance.

“Yes sir. I’ll give it a try.”

“Thank you, sweetheart. I think you’ll find the floor’s a lot more comfortable to sit on, now. There are a few other benefits, too.” He grins a little at Dean’s disgruntled scowl, and again when Dean takes a step and then pauses, and has to carefully readjust his stride because of the padding between his legs.
Keeping an eye on Dean as the sounds of a classic rock radio station start filling the room, Castiel busies himself sorting through some of the shirts and onesies, setting aside those that might fit Dean, just in case.

“I heard you and Charlie discussing Star Trek,” he calls out, seeing Dean eyeing the toy shelf. “I believe there’s a Lego model kit of a spaceship on there somewhere. The Millenium Hawk, or something like that.”

Dean turns horrified eyes to him.

Oh my God. It’s the Millenium FALCON. Falcon! And that’s Star WARS! Not Star Trek! The Falcon is a cultural ICON, Sir, I don’t even know how you...she can do the Kessel Run in 12 parsecs!”

Castiel, laughing, holds his hands up in defense. “I’m sorry! I meant no offense, popular culture is truly not one of my areas of expertise! Here, I see the box. Educate me about this culturally iconic spaceship.”

Coaxing Dean to the play mat with the box is easy. Listening to him chatter about Star Wars, and the story and the characters is also easy. He watches Dean’s face soften and brighten as he works on the model; he’d guessed that hands used to repairing automobiles would have an affinity for Lego. Dean drinks from a covered cup without complaint when Castiel brings him some juice and apple slices, and even wipes his hands easily, eager to get back to the model.

Not wanting to startle Dean, Castiel puts a gentle hand high on his thigh, first. “I’m going to check your diaper, baby,” he says quietly, not wanting to interrupt as Dean works two blocks together. His words still make Dean go motionless.

“I think I’d know if I pissed myself,” Dean says flatly.

“Hmm. But I’ll still check. Relax.” He slips his fingers in past the elastic leg, and the silky heat of Dean’s sac is pressed against dry padding. He withdraws them smoothly. “All dry. What a shame. Little guys who use their diapers get an extra surprise.”

Dean cuts his eyes sideways. “What surprise?”

Castiel shrugs. “Doesn’t really matter. You’re dry, and time is almost up. In fact, we’re over our training time by almost half an hour.” He shows Dean his watch.

“But…” Dean looks at the model, only about a quarter put together, and the pieces he’s assembling right now. His toes dig in to the luxurious pile of the carpet, and he rolls his shoulders, appearing smaller than he is. “Okay,” he says, reluctantly.

“We will come back tomorrow,” Castiel promises, hiding his smile. “And you can work on the model. The film sounds very interesting, perhaps we can watch it during your free time tonight? And then I’ll have a better idea of the importance of the...gun turrent?”

“Gun turret,” Dean corrects, rolling his eyes.

“Of course,” Castiel nods. “We’ll leave everything just as it is.”

“Okay,” Dean says, brightening.

“Up on the table, young man,” Castiel encourages him, and drops a kiss on Dean’s nose when he lies down obediently. “What a good boy you are,” he praises, gently unfastening the diaper. “I know this is a harder thing for you, and I’m so proud of how well you’re doing.” Dean blushes and blinks at him, clearly pleased.

He fetches a wet wipe, and gently starts cleaning the powder from Dean’s groin.

“Cold,” Dean gasps.

“Sorry, baby. Now, just like when we were practicing with the dresses, we will take small parts of this out into the house with us. Not the diapers,” he clarifies, when Dean tenses. “But when you need to use the bathroom, you will ask me permission to go, and I will help you. Perhaps that will help to show you that none of this is anything but another level of intimate care, and not shameful or in any way upsetting or dirty.” He strokes Dean’s hips gently.

Dean’s scowling at the ceiling.

“It won’t be so different from when you were on leash restriction,” Castiel reminds him. “Now, that’s enough for today. Do you need to use the potty before we go play with the toys in your bag?”

Jaw clenched but not too terribly tense, Dean shakes his head. Castiel puts a gentle hand low on his belly and presses. “Are you sure? That dry diaper was on you for almost three hours.”

“Yes, sir,” Dean insists stubbornly. Castiel sighs, and helps him off the table, ushers him to the door.

“So be it. Today, you will be sitting on my lap, but since we only have a little time, you will only be allowed to touch your breasts…”

***

That evening, Dean is clearly very reluctant to bring his paddle and the switch to the pillow at bedtime. Some days, he has no problem with it, and submits easily to it, sometimes even with a smile. Tonight he is struggling, though, his steps slow, face screwed up in a combination of resolve and frustration and a little anger. Castiel waits patiently in his chair, letting him work through it on his own.

When he finally makes it, kneeling on the pillow with the paddle and switch, Castiel feels a wash of pride. He’s not sure what causes these flare-ups; they don’t seem to be in the morning or evening particularly, or on hard or easy days. But Dean is doing better with them every day.

“Good boy,” he says softly. “Now ask me, lovely.”

“Please end my day of Submission with the paddle, and a strong hand, so I know how much you care about me, Sir,” Dean recites, sighing a little on the last word as if some last tension is released.

“Do you want to tell me what’s bothering you now, or after your paddling?” Castiel asks gently, stroking his hair.

“After, please,” Dean begs, and Castiel nods. “Please can I pee first?”

Startled, Castiel blinks down at him. Casting his mind back, it’s true..he hasn’t asked. Not through dinner, free time, the movie they’d watched, and he assumes his enema, since Benny hadn’t reported a request.

“Yes, of course. Come on.” He gives Dean a hand up, and leads him to the bathroom. Gently turning him, he gestures. “Sit, Dean. No diaper, but some parts of our current fetish remain, remember?”

Dean is clearly too far gone to even object. Gracelessly he sits and tucks his cock down, and instantly begins to pee, endlessly. It’s obviously such a relief, he bends at the waist, mouth opening in an O, arms crossing in his own lap.

“Never wait that long again,” Castiel scolds. “It’s terrible for your body. And it changed nothing, since here we are.”

“Wasn’t that,” Dean mumbles, looking up at him. “I didn’t know it was that bad, I promise. I thought maybe if I held it that thing would happen again. Remember? The, the wetting thing.”

Castiel leans back, shocked.

“You were deliberately trying to bring about a Submissive wetting?”

Abashed, Dean nods, looking back down at his knees. “Felt better than any time I’ve come I can remember. Kinda stands out in my memory. Since I was already holding it I figured, why not.”

“Oh, Dean.” Castiel sighs. Hearing that Dean is done, he helps him stand. “No, you don’t touch,” he warns, as Dean reaches for tissue. Castiel grabs a wet wipe, and urging Dean’s legs apart, begins cleaning him carefully. “Wetting doesn’t happen because you have a full bladder, though it probably helps. It happens because of an abrupt and complete drop into subspace. If you would like to try desperation play, and see if that sensation is still good for you, just ask.” He tosses the wipe aside, and washes his hands quickly.

“Didn’t know how,” Dean shrugs.

“I find directness useful. ‘Sir, can you fuck me with a full bladder and make me urinate from the pressure’ would probably work.” He smiles a little at Dean’s appalled face.

“I’d never use the word ‘urinate,’” Dean protests weakly.

“The point remains. Now, you’re clean, so place yourself over the chair arm. I will not punish you for endangering your own health, since it was clearly not deliberate. But the next time this happens, you will be switched severely, do you hear me?”

“Yessir,” Dean says, muffled against the chair.

He paddles Dean slowly and deliberately, morning and evening. Not a punishment, as he promised, but a reminder, so he makes sure that each smack is precisely placed, that the paddle rests on Dean’s rump for a moment after impact, and that it is deliberate and calm. By the tenth, Dean usually has a few tears in his eyes, and tonight is no different.

“Come sit with me, honey. Tell me what the trouble is, before you set yourself up on the bed,” Castiel welcomes the sniffling boy into his lap.

“I-I” Dean starts, then steadies himself. “I promised myself, after the dog play thing, when you just stopped it when it wasn’t working, I promised myself I’d try anything. Because you weren’t gonna m-make me do something I just hated or that didn’t do anything for me?” Castiel smooths tears from his cheeks, and nods.

“Thank you. That trust is very precious to me.”

“So, I thought I would hate it today. And I. I.”

“You enjoyed yourself,” Castiel prompts gently.

“Yeah,” Dean says, small.

“I know it can be an adjustment,” Castiel answers, after a moment of thought. “Expecting to react one way, and finding that expectation isn’t correct. And with something as intimate and challenging as age play, it can be even more of a jolt. Remember though, also, today we did a very small introduction. You played with Legos and wore an unused diaper, but we didn’t engage in any of the deeper behaviors. I would recommend you reserve judgement for at least another day or so.” He smiles at Dean. “I think everyone likes Legos.”

Dean sighs. “I guess so. You’re gonna make me do more than that tomorrow?”

“I think it’s only fair,” Castiel answers.

With another sigh and a last kiss against Castiel’s fingers, Dean levers up out of his lap and goes to the cabinet. Fetching the lube syringe and filling it, he crawls up onto the bed, and takes a few deep, settling breaths. Castiel loves watching this, even as he carefully strips and sets his clothes away. Seeing Dean prepare for him, mentally more than physically, shoots arousal all through him; the way he breathes deep, shakes his shoulders a few times to settle them evenly, flexes and relaxes his hips as he curves his body into waiting.

Every night, his Present position seems to get more perfect, the dip of his back deeper, the spread of his thighs wider, his hips tipped up more invitingly. His hole, tiny and pink, is fully exposed and waiting there, above the small, submissive softness of his cock and balls.

Castiel licks his lips, and shoves the syringe in suddenly, relishing the startled clench of Dean’s pink-paddled cheeks, the bow of his back in silent protest.

“I think you’d better hold on to something, darling,” Castiel leans over him to say as he empties the syringe, feeling the Dominant burr in his voice and watching it shiver through Dean. “I have been hungering for your perfect bottom for hours, and I do not expect to find much restraint tonight.”

He watches Dean’s hands make white-knuckled fists in the bedspread, even as he knees up between Dean’s spread thighs, lifts his raging erection to prod the head at Dean’s hole. He’s barely slicked himself, and the hard-smooth head of his cock catches, sticky and hot, on the rim of Dean’s hole and then skids down to nudge his perineum. The second time it hooks into the small give of Dean’s hole, though, and every muscle in his hips and midsection curls tight, his breath stutters hot and fierce, and for one second he’s totally still...and then it all unleashes forward, in a primal surge of his whole body that nearly forces Dean down flat onto the bed.

The burn against his cock of the too-tight hole reluctantly parting has his teeth baring in satisfaction, as Dean’s body clamps down and he shrieks into the covers, his thighs going loose and weak even as his feet reflexively kick up.

“That’s it. Sing for me, sweetheart,” he says, and pulls out and shoves in again, the clutching wet heat almost too much to bear. “So good,” he gasps, “so fucking perfect,” and does it again, and again, Dean’s cries driving him on.

His hips flex and pump, catching and holding a rhythm, the first burn of penetration fading as his cock cores a space for itself into Dean’s body. He folds a palm over Dean’s shoulder, yanks him back harder into his thrusts, and Dean’s face turns to the side, revealing his open mouth, eyes half-closed, near-euphoria on his face.

Castiel reaches down below. The boy is soft, his cock bouncing with every heavy thrust, and Castiel wraps his free hand around those tender balls and squeezes.

“AHHHHHHH!” Dean jerks back, impaling himself hard, a low cry breaking from his lips at that again, falling forward, his hands scrambling for purchase, trying to crawl away.

“Don’t you dare,” Castiel growls, yanking him back with the hand still on his shoulder. His hips connect with Dean’s ass with a *smack* and Dean howls, arching, hands clenching on air as Castiel holds him up and drives into him over and over, hips pistoning.

“Good boy,” he manages to pant. “God, Dean, you are so good, so sweet.”

“Sir,” Dean keens, whole body jolting, one hand down and supporting his weight as best he can, “Sir, please, hurts so much, please stop, please, too much, hurts, I can’t--”

“You can,” Castiel snarls, “let go and submit, let it go, give it up. Let go,” he twists the hand still holding Dean’s balls and the sound Dean makes is barely human, his supporting arm collapses under him and he goes limp all over. The hard muscles in his lower back soften and inside, he goes liquid-soft. Castiel lets go of his sac, gets his hand around Dean’s hip to hold him, and catches his rhythm again, starting to chase his orgasm in earnest. Fast and hard, he plunges deep, again and again, faster every time.

“Good boy, so good,” Castiel praises, over and over, and Dean’s face is showing that exalted agony again, bliss that has nothing to do with physical pleasure. Seeing it yanks Castiel’s orgasm out of him like it’s on a string, and he bites kisses into Dean’s shoulders as he hunches over, hips driving hard to get the last, sweetest moments of pleasure deep inside.

When he finishes, he eases Dean, still sobbing quietly, down to he belly on the bed. Bracing himself, he starts to pull out, only to have Dean twist under him.

“Noo,” he begs, hand grasping Castiel’s arm. “Don’t go, please stay. Sir. Stay in me.” His eyes are vague, blown dark and hazy, his voice is thick and slow, and all the muscles in his pelvis are still quivering.

“Easy, lovely,” he soothes. “I need to clean us up.” He pulls free and Dean sucks a breath in at the feeling, then relaxes again, seemingly boneless. Castiel cleans them quickly, then spreads Dean with a thumb and forefinger: no abrasions, just redness from the friction. When he turns off the light and pulls Dean to him on the pillow, though, Dean clings with arms and throws a leg over his hip, clearly trying to angle himself so Castiel can slide back inside him.

“Want it, want to feel you,” he insists, obviously still deep in subspace. Castiel caresses the bottom curves of his ass with both hands, sighing. He rubs and spreads them, considering, then shifts Dean so his cockhead is pressed into his loosened hole. Short, firm upthrusts seat him again inside Dean, and soon he’s back deep inside, with Dean’s face tucked against his shoulder, little gasping breaths warming his skin.

“Thank you, thank you,” Dean hums. Castiel cradles the back of his head in one palm. He knows the position and the deep penetration will wake Dean in the night in discomfort, but he can’t deny him when he’s like this. And his cock warm and snug inside Dean is not something he can resist, anyway.

As Dean slips into sleep, hitching breaths slowly smoothing out, Castiel thinks that soon, Dean will need to begin working with the other trainers on staff for aspects of his Submission. It will be good for Dean to accustom himself to other Dominants and their styles and needs. And just as valuable for Castiel, he thinks, to gain some separation. And, as the darkness forces him to admit, to not become more attached than he already is.

Chapter Text

Dean’s pretty sure he pulled a muscle in his thigh and tweaked his back somehow last night, but he just does not care. He’s still drifting a little, feeling no pain, all the way through breakfast. Sir feeds him french toast and potatoes until he’s satisfied, and coffee, and Dean practically purrs. Even the short, sleeveless dress he’s wearing this morning is perfect in every way.

Sir talks into the intercom briefly, and drops a hand to Dean’s hair once they’re done eating.

“Do you need to sit, sweetheart? Is your leg stiff?” Sir has been keeping an eye on him since he complained in the shower. Dean shakes his head.

“It’s much better than it was, Sir. I’m fine.” He smiles.

“Good. Ah, there we are.” Dean looks up curiously and then grins at Meg and Charlie, Cole and Benny, and even Ash and Crowley walking in to the dining room.

“Claudia is sick today,” Meg tells Sir, “so Cole and I are covering for her today. Don’t be surprised if the towels aren’t properly fluffed, that woman has a magic touch.”

“Thank you both,” Sir says sincerely, “and that leads nicely into the reason I called you all here. As of yesterday, and confirmed today, Dean’s levels are within high-normal range for everything. He has officially settled.”

Dean is shocked, and stares up at Sir, even as Meg claps her hands and Benny lets out a whoop.

“Definitely a cause for celebration,” Sir agrees, his smile big, his hand never leaving Dean’s hair, and indeed, a little heavier? “And though it’s a little late, it means that Dean can now start the more routine training protocols in the house.” He nods to them all. “Time to start earning your keep, people.”

Meg scoffs a little, eyes bright. “As if it’s such a chore.”

Sir looks down at Dean, meeting his eyes. “Most of the staff here are licensed trainers, as well as having their other duties. And as Submissives progress in your training, you will work with them, and with some other Dominants from the Novak Corp, in areas where they have expertise. It’s the best way to make sure your training is the best it can be.”

“What do you mean?” Dean’s happy floating morning feeling is rapidly disappearing, replaced by cold anxiety.

“Well, for example, Meg will be training you in Service Submission,” Sir nods to her, and she wiggles her fingers at him with a grin, “as well as some strictly Female Dominant-focused skills.”

“Not to be missed!” Charlie interjects, to some laughter.

“Benny will handle your Medical Fetish exploration, Cole will be responsible for oral training. Crowley will be in charge of protocol and etiquette, as well as formal wear and makeup for your female wardrobe.”

The dapper little man inspects his fingernails. “My lessons always seem to be forgotten most quickly,” he mourns.

“I love them!” Meg claims.

“As do I,” Castiel confirms. “Ash practices Shibari at a master level, and will be exposing you to that practice. As well, I’ve been considering Jerome and Peter--” he looks up at his staff, and nods at what he sees, “to come in at some point, to hand over your overall care temporarily. It’s a good thing to experience other Dominants’ styles and methods.”

“Sir,” Dean says, and it’s almost a whimper; he realizes he has his hand clenched in Sir’s trouser leg only after he’s already spoken. “But you’re my Trainer. Not them. I know Benny and Meg and...but, strangers?” He’s freaking out, he knows it, but what the fuck? The idea of some other Dominant, someone not-Sir with their hands on him, touching him, looking at him inside and out, ordering him around, it makes his stomach turn.

“We’ll speak about this more,” Sir tells him gently. “But for now, we celebrate your return to good health.”

“We’ll finally get to play a bit, eh cher?” Benny tousles his hair on his way out the door, and Dean manages a smile for him. He likes Benny fine, but. And everyone’s so happy for him, and all he can think is that he fucked up, or something’s wrong, or...he has no idea, but this doesn’t feel right at all.

“I only want you, Sir,” he says, when the room is empty. He’s staring at Sir’s knee.

“Dean, lovely,” Sir sighs. He tugs Dean up and pulls him into his lap. “It’s normal to develop a strong bond with your first Dominant. And that trust is so important, and I could not be more honored by it. But I am your Trainer, one of possibly many. You need to experience more, to prepare you to find a real relationship, a contract, that will be good and meaningful.”

“What if I don’t want that!” Dean bursts out. “What if I want...I can go work for you, in a training center! I could hunt on the side. Then I don’t have to work with anyone else.” He’s feeling desperate. He really and truly does not want to submit to anyone else. Not when he’s finally found real bliss in submitting to Sir, realized what it can feel like with someone he genuinely trusts and...likes. Respects.

“Perhaps that’s what you’ll do,” Sir allows. “But it shouldn’t be because that’s all you can do. You will work with other Dominants, Dean. It’s important, and healthy.”

“This is not going to go well,” Dean predicts. He doesn’t even bother to dissemble. Sir deserves his honesty in this, and Dean can feel resistance hardening through every bit of himself.

“Try, at least, with the staff. For me, Dean.” Sir makes it an order, but Dean nods like he’s agreeing, after a long moment. With the staff, he can try. With outsiders? It’s anyone’s guess.

***

Dean is still jittery and agitated by the time they get to the playroom that afternoon. He hadn’t been able to run with Cole because of his leg, and the excess energy isn’t helping. Possibilities keep swirling around in his head. What if he just can’t do it? Will Sir be disappointed? What if he can do it, what does that say about him?

He stops dead inside the door of the brightly-colored playroom.

“Maybe this isn’t the best day for this, Sir,” he says dubiously. He can’t think of anything he feels like less than sitting around in a diaper and playing with toys, pretending to be a kid. He has major existential issues at hand.

“I think today is the ideal day for this,” Sir insists gently, and puts a hand in the middle of his back, driving him forward. “We’ll get you a snack first, and something to drink. See, the Falcon is right where you left it.”

It’s true, the model looks undisturbed. And Sir really had seemed to enjoy A New Hope last night, which was cool, because it means Dean doesn’t have to disown all knowledge of him forever.

Reluctantly, Dean steps in, and climbs the little footstool, and up onto the table. Ugh. He just knows he’s gonna be thinking about the stupid ‘Guest Dominants’ or whatever the hell they are the whole time.

The diaper really isn’t so bad, he thinks, distracting himself as Sir puts it on him. It does make sitting on the floor way more comfortable, and it’s kind of warm and comforting, in a way. If he doesn’t think about what it’s for, he can even enjoy the cozy feeling. And having Sir tend to him like this feels so good. He’s smiling, and gentle, softer than usual and laughing a lot more.

Once Dean’s all padded up, he goes straight for the Lego set. But Sir holds his wrist.

“Snacks first, young man,” he says sternly. With a big sigh, Dean follows him to the red table. Snacks today are crackers shaped like animals, and grapes, and cheese in cubes. A big cup of water with a top on it, that Dean gives a skeptical look to.

“It’s very much like a sports bottle,” Sir encourages.

“I know what you’re doing,” Dean accuses, even as he’s reaching for the grapes.

“Hmmm,” Sir agrees, and reaches to rub Dean’s belly, his fingers just slipping under the snug waist of the diaper. His eyes are crinkled up smiling, though, and Dean can’t even be mad.

“I think you should call me something other than ‘Sir’ in this room,” he adds a moment later. “You may call me Castiel, if you wish, or something else if that works better. Let me know if you think of something.”

Dean chews, and drinks, and thinks. “Castiel is too long,” he finally declares, “and not respectful enough. And Mr. Novak sounds like you’re the butler or something. Can I call you Mr. Cas?” It’s not quite right, not exactly what he’s looking for, but it’s close.

“I think that would be fine, Dean.” There’s those smiling eyes again. Dean grins happily.

Water and food finished, he’s finally allowed to flee to the Falcon, leaving Mr. Cas to clean up. He dives into the model again, delighted to see the ship slowly taking shape as he fits all the pieces together painstakingly. Piece by piece, the round shape comes together. He’s so engrossed that the touch on his shoulder makes him jump.

“Dean. It’s been over an hour.” Mr. Cas is looking down at him. “It’s time to take a break, baby. Come pick out a book and sit on the couch with me.”

“In a minute,” he says vaguely, already contemplating where the next block goes.

“Dean.” Mr. Cas’s voice is a little stern, now. “Your leg is sore and you need to rest it. Come on. Right now.”

“After this piece!” He doesn’t even look up.

“Dean Winchester.” That voice gets his attention. Mr. Cas has his arms crossed and he’s not smiling anymore. “When I say right now, I mean right now.”

“My leg feels fine!” He wiggles his toes to show it’s true. “I’m just, there’s one more part.”

Mr. Cas sighs. “Okay, young man. I can see we need to work on listening. I think you need to stand in the corner for a few minutes until you can remember how to be a good boy.” A strong hand around his arm lifts him easily to his feet, and he’s too shocked to even struggle. It marches him to an empty corner, and his nose is pressed right into the corner until it touches.

“Not listening and arguing back is very disrespectful,” Mr. Cas says, all stern. Dean is still shocked, all turned around, but that voice is making his stomach do upset turns. “You keep your nose there for five minutes, and think about that.” And with that, he’s gone.

Dean’s mind spins. He’s standing in the corner and nothing is keeping him here, except, except, how he feels really bad, for not listening, and even though there definitely was one more important piece, he should have picked out a book. Sitting on the couch sounds nice too. His nose feels funny in the corner, and his neck aches a little at this angle, and he looks so stupid, he knows it, his butt sticking out in a diaper, his nose in a corner. His eyes fill with tears. He deserves it, though. He was definitely not as respectful and nice as he should have been.

And now that he’s standing up he needs to go potty, too.

He sniffles. He doesn’t want to go in the diaper. He’s scared he’ll like it, like the toys and the snacks and the simple, quiet way his mind is working right now, he knows it and recognizes it but can’t work up the will to struggle against it. He shouldn’t like it or want it but it feels so nice.

“Okay, that’s five minutes.” A gentle hand on his back turns him away from the corner.

“S-sorry,” Dean says, woeful.

“That’s all right, sweetheart. You’re forgiven. Now go pick out a book, we’ll spend some time on the couch.”

Dean hurries to the shelves and grabs a book about trucks. Mr. Cas is sitting sideways on the couch when he comes back, and Dean isn’t sure where to sit, but Mr. Cas pats the couch between his legs, and Dean crawls carefully into the spot there.

“Lean back against me, just like that. Now we can both see the pictures.” He holds the book in front of Dean, his hands resting low on Dean’s belly. It makes Dean squirm, the pressure there, but he can’t close his legs like he wants to, with the diaper padding there.

“Sir,” he whimpers, the pain already building in this new position.

“Let it go, baby,” Mr. Cas soothes. “It needs to happen. Just try to relax.”

“I can’t!” He really doesn’t think he can.

“We need to see how it works for you,” Sir says. He closes the book and sets it aside, just holding Dean for a moment. “It’s an important part of this fetish. I can give you a diuretic and a laxative, which is the step we’ll have to take tomorrow, if I have to, but I would much rather you let go and let it happen naturally.”

Dean stiffens in horror at that.

“I don’t even--Since Benny, I don’t--” he can’t even say the words.

“I know. I know, remember? We’ve been visiting the bathroom together, and I notice how you eliminate. Sometimes it helps to break the mental barrier to get everything moving, though, and as I told you, nothing about this is dirty or wrong, nothing will make me look at you differently, or think of you poorly.” His hands start rubbing gently, pressing here and there on Dean’s abdomen. It hurts. Thinking about it so much makes the painful pressure even worse, crampy and mean.

“Can you help me?” His voice is small in his own ears.

“Of course, baby.” Mr. Cas rubs his belly harder, then reaches up with one hand. “Hide your face in my arm, just like that. Close your eyes, my good boy. There, that’s good.” Dean hides his face and Mr. Cas smells so nice. He feels a warm hand and strong fingers on the back of his neck, rubbing hard, and pressing in near the top of his spine. Tense muscles relax all down his back, and he breathes deeply. Then Mr. Cas pushes hard, right over his pubic bone, and startled, he can’t clamp down.

The first hot trickle breaks the seal. He can’t pull it back, and it feels so good, and then he’s peeing helplessly, the relief tearing a sob from his throat. It’s like he’s coming, only not, the pleasure is so intense, the release, the wet heat around his groin. He feels the padding soak and swell as he empties himself for what feels like forever, and he’s vaguely aware of Mr. Cas praising him, petting him, saying sweet things. But all he can do is feel the pleasure.

His cock stiffens inside the wet diaper and he whimpers again, burrows into Mr. Cas’s chest, so embarrassed, and the embarrassment makes him even harder. The twist of shame makes it sexier, in his dazed mind, overwhelmed by what he’s done.

“That was so good, Dean,” Mr. Cas’s voice suddenly registers again. “Wonderful, amazing boy. I’m so proud of you.” He is stroking Dean’s sides, his belly, his chest, warm and nice. “Come on, honey, let’s get you changed. Nice and dry.”

Dean can tell that the diaper won’t be nearly so nice once it cools, but he still doesn’t really want to be changed. Still, he gets up obediently, biting his lip at the heavy fullness between his legs, walking carefully to the changing table. Mr. Cas has a blanket down where his hips go, and he lies down carefully on it.

“You are the best boy,” he says warmly, unfastening the tapes. “Oh, and that’s so pretty, Dean, such a hard, happy little penis, I can see it felt so good for you, too. That’s beautiful, baby. So good, I’m so proud.” The last of his uncertainty washing away under the warmth of the tone and the words, Dean lets himself relax and bask a little.

The cool of the wipe softens his erection, but not all the way, and as Mr. Cas folds the fresh diaper up around him, the soft warm padding pressing against it makes him wiggle and smile.

“Does that feel nice?” Mr. Cas grins down at him, then swoops down to kiss his belly with a theatrical smack that startles a laugh out of Dean, before helping him sit up. “I bet it does, you silly thing. Okay, mister, back to the couch. Let’s read that story.”

“But I went potty in the diaper,” Dean whines, looking longingly at the Lego set.

“And you still need to rest,” Mr. Cas says firmly. Dean ends up right where they’d started, resting back against his chest, listening to him read about trucks that go to school. Mr. Cas only slaps his hands once for rubbing on the front of his diaper, and then he gets to play Legos again, and have another snack. And then he’s done, Mr. Cas says, but he doesn’t really want to be done, and he has to fight back silly tears as he’s on the table getting his diaper off.

“It’s okay,” Sir gentles him. “I know, it’s hard to move back and forth sometimes. Would you like to keep your diaper on, under your dress today when we leave?”

Dean thinks about it, but shakes his head, eyes still wet. He’s definitely not ready for that yet.

“All right. Bottom up. Good boy.” Sir cleans him so softly, and gives him little kisses on his hipbones, he feels so cherished and special. When he gets down off the table he’s smiling again.

“I think we can call age play a success,” Sir says, as they leave the room together. Dean ducks his head, but has to nod agreement. He feels refreshed, like he’s had a long nap, and lighter, as if most of his worries have just been scrubbed away. He remembers that he’ll be working with other Dominants, but he knows and trusts Meg and Benny and Cole and Ash, and Sir will be right there, he knows, close by. Everything else, he’ll just deal with when it comes.

***

They take it pretty easy for the rest of the day, and Dean is grateful. He feels kind of fragile in his skin, and he just wants to hang out near Sir as much as possible. Sir doesn’t seem to mind, and smiles at him when Dean sets up camp on the couch in his office during free time.

Meg and Benny come in for a meeting, and Dean listens with half an ear. Apparently Claudia is still sick, and Meg promises to send someone to check on her, and she asks if she can have Dean to start working on Service Submission soon, since there’s an actual need. Dean’s ears perk up at the mention of his name.

Sir glances at him, and sees him watching.

“I think that would be fine. After his workout tomorrow, you can take Dean for the day. He’s had a fairly easy day today; we practiced age play, and he accepted his diaper enough to wet.”

Benny beams at him, and Meg claps her hands and then gives him a smile and a thumbs-up. “That’s awesome, Dean,” she says enthusiastically. “I usually don’t let my service Subs use the toilet while they’re serving. I was going to figure out something with a bucket, or puppy pads, but this is way better. Congratulations!”

“One of my favorite fetishes,” Benny adds earnestly, not even mentioning Dean’s burning red blush. They’re just talking about all this like it’s, like it’s so normal, just everyday stuff like the weather, or what’s for dinner. For them, he guesses, it kind of is. And that thought lets him relax and smile back, a little, though his face still feels hot.

“Someday I’ll find a lovely little Sub who will wear diapers for me 24/7, and I will finally sign a long-term contract,” Benny goes on dreamily, and Meg laughs at him.

“But why?” Dean breaks in, fascinated and a little scandalized. Benny just shrugs easily.

“We like what we like. I find it fascinating and sexual and intimate to dig deep into parts that others consider private, or shameful, sometimes medical or clinical, even dirty, though I never thought so. Always been that way, cher. I like watching y’all squirm.” He winks at Dean, who blushes even harder, to Meg’s increased amusement, and even Sir chuckles, though his eyes are hot and kind of heavy, watching Dean. Like he's considering something.

“You’ll have your chance to watch Dean squirm on Friday, with Medical Fetish,” he says, grinning. Dean has to duck his head. “Let me know if there’s any special prep he’ll need,” he adds, and Benny nods.

“We’ll do some urethral sounding, probably a speculum and full checkup, a little dilation, maybe an internal sonogram,” he grins at Dean. “I’ll let you know if he needs a lot of extra water before.”

“Awww, Benny,” Dean complains, and Sir laughs again.

“All right, so the schedule is set. Meg, you’ll let me know how Claudia is feeling, if she needs anything at all? And I’ve contacted Peter, he’ll be arriving Friday afternoon for the weekend. Can you be sure the guest suite on the main floor is ready? And make sure dinner tomorrow is with the whole staff, anyone who wants to say goodbye to Charlie.”

“Sure, Boss.” Meg makes a quick note, then stands. Dean is biting his lip again at the mention of this stranger Dominant, but Benny and Meg seem to think it’s normal. “Bye, cutie. Rest up, tomorrow you’re mine,” she says cheerfully as she and Benny leave. Dean’s left flustered on the couch.

“I don’t know exactly what Service Submission is, but I think I’d rather piss in a bucket than wear a diaper and do it,” Dean says, strangled, after a long pause.

“Dean,” Sir rises, and comes and joins him on the couch. “That will be something for you to discuss with Meg tomorrow.”

Stricken, Dean meets his eyes. He sees something, a flash of strain, or tension, or pain, cross Sir’s face, before it’s smoothed away.

“It will be easier than you think,” he continues gently. “It’s why we start with Dominants you already know, and trust. And Meg and Benny are the highest-level Dominants here besides myself, and the most familiar to you. She knows you, too, and has seen us and our dynamic together. And you know that I trust her very much. She will demand your Submission, and your obedience, just as I would, and you will do your very best to give it to her.”

“I submit to you,” Dean says, stubborn, and Sir tugs him close.

“And you still will, lovely. This will just teach you other ways.”

“I don’t like it.”

Sir sighs, and pulls Dean’s head against his shoulder. “But you will still try.”

Chapter Text

Chapter 30

Dean runs his fingers over his collar in a nervous gesture, standing in the middle of the floor. Sir had put it on him this morning, saying it was a reminder that no matter what, he’s Dean’s Dominant, and that he’s expecting Dean to behave well and remember his manners. It is comforting, like Sir’s hand on him, but looking at Meg typing something at her desk right now, Dean really wishes Sir was here right now, instead of just the collar.

“All right,” Meg announces, finishing with a flourish. She stands up and walks to him, eyes running over him from head to toe. He fidgets again as she walks around him slowly.

“Hi?” he tries, and she clucks at him disapprovingly.

“I talk, you listen, right now. I spoke with Dr. Novak about today, and I want you to know that everything I plan to do has his approval. We both think that will make it easier for you. So for now, kneel.”

He sinks down, relieved by her words. He still doesn’t feel submissive in the least, but he knows Meg, he’s worked with her. She’s chaperoned him, and now that she’s established a boundary already, he’s not so nervous anymore.

“Service Submission is finding satisfaction and fulfillment through tasks and jobs that make your Dominant’s life easier, better, and more comfortable,” Meg starts, as she drags a folding chair over and sets it up directly in front of him. He watches, interested, in the Wait position. “Not all Dominants and Submissives enjoy it; it’s very nearly a fetish itself, though because it involves everyday tasks, some people don’t think of it as one. Many Dominants will combine it with another fetish, such as crossdressing, forced nudity, diaper discipline, or others, and sexualize it that way. Some won’t. You follow me so far?”

“Yeah,” Dean nods.

Quick as a flash her hand has him by the chin. “Let’s make sure this goes well. You will answer me with yes, ma’am and no, ma’am. Do you understand?”

“Yes, ma’am,” Dean squeaks, feeling his eyes go wide. She’s leaning very close, and he can see all her teeth. There’s something about her, something that almost reminds him of Sir. It’s a little extra, like a hint of static electricity, the smell of the air after lightning strikes. Whatever it is, it has him feeling very careful.

“Good.” She lets go. “Of course, all Submission is service. You serve the pleasure of your Dominant, however it might be expressed. This particular kind is domestic service, though, and it’s something I enjoy very much.”

Dean nods this time. So, he’s going to be doing housework?

“We’ve been together before more casually, so we’ll start slowly. We’ll do a few small exercises to try to get you into the right mindset. Then I’ll have you vacuum the carpets downstairs here in the main house, wearing your diaper, since as I told you, Service Subs under my direction do not have toilet privileges. Dr. Novak told me that your nightly enema takes care of any solid waste, but if you wet, you will tell me immediately.” She grins at him. “Not that I expect you’ll want to clean house in a wet diaper. Once you’re done vacuuming, we’ll sit down together and evaluate. All right?”

Dean’s ears feel like they’re going to burst into flames. He still doesn’t feel Submissive to Meg, nothing beyond the regular low-level respect and deference he’s always had to her since the first time she chaperoned him. But he promised Sir he’d try.

“Yes ma’am,” he gets out, again.

“Dr. Novak would probably talk to you for a while about Submission, and finding your center. Me, I’m a little more primal,” she tells him, showing her teeth again, even as she’s drawing her skirt up. Dean can see a scrap of lace between her spread thighs. “Men, especially, have a good strong link to the animal brain. So move forward, little boy, and put your face in there. Close your eyes and breathe, get the scent.”

Mouth dry, even as his palms feel sweaty, Dean moves forward on his knees. He follows her beckoning gesture and ducks his head down under the hem of her skirt, pressing his face into her crotch, his cheek against smooth skin, his nose finding her pubic mound. She drops her skirt over his head, cocooning him in darkness.

All he can smell is woman-scent. After weeks with only Sir, it’s dizzying. Not heavy, but a little sweet, a little salty, a little dash of bleach-basic on the back of his tongue as he breathes. His eyes are closed, as ordered, and he feels her small hand and sharp nails on the back of his neck. Right over his Angel Gland. As she starts to massage him there, he rolls his face to the side, and her clitoris is rising and tenting her panties, smooth and firm as a finger, a few tall inches that brush his cheek.

Fuck, he can feel the now-familiar warm relaxation spread down his spine. Maybe he’s not getting enough air; his mind feels slow, drugged. She’s around him, over him, everywhere. He feels strangely safe.

After what could be a minute, or an hour--but his knees are distantly starting to ache against the floor--he feels cool fresh air on his face and realizes the skirt has been removed. Firm hands sit him straight back up, and though he keeps his eyes closed, brighter light filters through his lids. Ow.

“I was going to give you a spanking, but I don’t think that will be necessary,” Ma’am sounds amused. “You can keep your eyes closed, Dean. On your back, knees up. We’ll get you ready now.”

Feeling about as stiff as a noodle, Dean obliges, rolling to his back. He feels her fingernails tap teasingly on his chastity cage, then lifts his hips when silently prompted, and shivers a little as she efficiently fastens the diaper onto him.

“All done,” she says, as her hands leave him. “Open your eyes slowly, boy. Back up to your knees.” Blinking to adjust to the light, he manages to blurrily focus on her as he gets back up. “There you are. All right, now to your feet. Carefully. Well done.”

He’s definitely not in subspace, but he’s feeling small and obedient. He can almost still smell her, and the sharp crispness of her voice, so different from Sir’s deep rumble, keeps him paying close attention as he follows her to the closet and fetches the canister cleaner.

As soon as the vacuum starts, though, all the nice fuzzy floating feelings go away. He knows cleaning, he has done this at the auto shop, at home, in hotel rooms his whole life. This is chores, not something he does as part of Submission. But he reminds himself he promised to try, again, so he sets his jaw and resolves to forget the annoying presence of the diaper, and gets to cleaning.

Meg is watching from the end of the hallway, arms crossed, as he zips through, getting all the corners efficiently and making sure the lines are straight. He moves the cord, going through to the sitting room next, since it seems logical. With Claudia out, it’s fine to pitch in, he’s happy to help.

“Ugh,” he itches under the collar, where he’s sweating a little.

“Doing all right, boy?” Meg is closer, watching again.

“Fine, ma’am,” he says politely enough, a little annoyed at the interruption. She cocks her head and narrows her eyes a little, but lets him continue.

More than familiar with cleaning awkward spaces, he has the sitting room finished quickly, moves the cord again, and does the far end of the hallway. Then into the dining room, which is a little harder with all the chairs and the kneeling pillows, but he gets it done.

He fucking hates the diaper. It’s awkward, it keeps him from walking normally, and it’s rubbing him weird. It’s not comforting and nice like when he was in the playroom with Sir, it’s just an annoying hindrance.

“Dr. Novak’s office next,” Meg directs him in a neutral voice. He could turn either way, next, so he nods at her and opens the door. And Sir is at his desk! Dean grins at him helplessly, and Sir smiles back at him just as fast, before glancing past him and nodding at Meg.

“Meg, Dean,” he says calmly. “May I get out of your way?”

“Oh no, you can stay,” Meg says, sauntering in past Dean. “I think it’s safe to say that Dean here is in no way, shape, or form a Service Sub. Soon as he picked up the vacuum he was in pure work-mode, not a hint of dynamic about it. But I’d hire him as a housekeeper in a heartbeat.” She grins at Dean as she waves at the room. “Carry on, boy.”

Shaking his head a little, Dean gets the room done as quickly as he can, while still being sure to be thorough. Sir and Meg get out of his way when needed, and then he and Meg move on to the other rooms. Dean feels a lot more cheerful, just for having seen Sir’s smile.

It doesn’t take very long, and after the vacuuming, Dean folds sheets and towels, cleans the glass and mirrors in the entryway, and changes the linens on a guest bedroom downstairs that he didn’t even know was there. When they’re done, Meg leads him back to the room where they started.

“Knees,” she orders, and he kneels, happy to get off his feet. “You were doing well until you started working. Explain what changed, then.”

Dean looks at her boots, crossed at the ankle in front of his knees while she leans back against her desk. “I think...that kind of work, it’s just part of living somewhere. Just normal life, you know? Nothing submissive about it.” He shrugs, a little helpless. “Cleaning and cooking, all that stuff, sure it’s domestic, I’m happy to help out, glad I can do it. But it doesn’t make me feel any way except eager to get it done.”

She hums a little, thoughtful. “Would wearing different clothing change that, do you think? A maid’s outfit?”

Dean barely has to think about that. “If this didn’t make a difference,” he tugs a little at the waist of the diaper, distastefully, “a dress definitely won’t.”

“And it’s still dry. You’re no fun at all,” she very nearly pouts at him. “All right. So, Service Submission is a bust, clearly, which is a shame given your talents. Here.” She leans forward and unfastens the diaper, not even making him lie down first before whipping it off and tossing it in the trash. He sighs in relief.

“Oh man, thank you,” he says sincerely. “That thing was making me crazy.”

“Interesting that you only tolerate them when you’re in the right mindset,” Meg comments. “Also interesting is that I’m supposed to teach you to please a female Dominant, but I’ve been instructed not to fuck you, your useful part is in a cage, and I suspect you’re already quite good with your mouth.” She cocks an eyebrow at him. “Am I right?”

“I’ve never had complaints,” Dean admits with a touch of modesty, looking down, licking his lower lip. She laughs.

“Which doesn’t mean you don’t have anything to learn, but I think I’m gonna wait on that. Do you need the bathroom?”

Dean groans quietly. “It’s still really weird for me, this whole bathroom thing,” he informs her. He does have to go, actually, so he nods.

“Get used to it, babe,” she says, unsympathetic. “Managing, handling, and controlling your body functions--eating, sleeping, bathing, eliminating, ejaculating--it’s one of the most intimate and fundamental Dominance urges, and the higher the level, the stronger it gets. Once you get a contract, you might never pee alone again.” She reaches out and helps him up as he tries to process that. Mostly, honestly, he’s resigned. It’s not so bad. He’s getting used to it, and it does make him feel cared for, in a strange way.

He certainly won’t get lonely, he thinks, as Meg unlocks his chastity cage and carefully cleans him after he goes. She has him put a leg up so she can wipe around the base of his sac and shaft, too, hands gentle and thorough. She moves the cleansing cloth back, wiping the creases under his cheeks, where his thighs meet, his taint, and his hole, freshening where he’d sweated while he worked. The watching and cleaning makes him feel valued, he realizes in a flash, blushing as she feeds his cock back into the cage, locking it in place. Special and worthy of attention. That’s the part he’s still getting used to, more than anything.

“Thanks,” he murmurs, glancing at her almost shyly. She smiles back at him, genuine.

“My pleasure, sweetie. Now, we’ve got almost an hour left, since you’re a madman with a vacuum. Charlie’s still doing something in the server room, and I think Dr. Novak’s on a conference call. Do you play blackjack?”

“Hell yeah I play blackjack. Lead the way.”

***

Castiel finally hangs up the phone, and frowns. The legal teams from Los Angeles and New York had talked for almost two hours longer than he’d expected, and though he’s thrilled that the legal details are now solid for the Dominant Centers, he does regret having to miss watching the next movie in the Star Wars saga with Dean. In fact, it’s very nearly time for his enema, and then bed.

He hunts the boy down in the television lounge. Dean is sprawled out on the couch, the TV on but muted, and a book in his hand, of all things. His full mouth is turned down in a discontented curve, but he looks relaxed and comfortable.

“Did you save the movie for tomorrow, Dean?” Castiel smiles at the thought. “That works out well. You can tell me how it went with Meg, today, instead.”

Dean doesn’t answer and doesn’t look up. Castiel feels himself pause, then start to frown. He’s well aware that Dean has five exceptional senses.

“Dean,” he says, sharply.

“Fuck off,” Dean answers abruptly, and throws the book on the floor, still not looking at him. “It’s not like you care, so why even bother?”

The surge of simultaneous hot dominance and cold resolve is a rush, Castiel can’t deny it. It’s why he has always preferred working with Submissives in training, or Subs who have defiance or stubbornness or bratting as a defining trait. He knows it brings out the best in him, and he likes to think he deals with them very well. Right now, for example, he simply folds his arms over his chest, and waits, not moving a muscle.

Working with another Dominant can cause this, sometimes. And it’s necessary to be very firm in correction, to re-establish the dynamic with no hesitation.

Dean’s eyes dart to him, then away. He fidgets. Then squirms. Then looks at him again, longer. Castiel stares, level and disappointed and cold. Dean draws his legs up, then swings around so he’s sitting on the couch instead of sprawling. Rubs his hands on his thighs. Looks at Castiel again, then away.

“WHAT?” he finally bursts out, still sounding sullen, but also now worried, with some guilt added in. “It’s true!”

“Not only is it untrue, it is disrespectful, rude, and unfair,” Castiel says calmly. Leaves it at that. Dean rubs his hands on his thighs again.

“Stop,” he begs, after a long moment, his shoulders curving in, knees pressed together, looking smaller by the minute. “Stop looking at me like that. Sorry I swore at you. I’m really sorry. That wasn’t cool.”

“I think you know what to do if you want to be forgiven,” Castiel answers. He still doesn’t move.

Dean squirms again, curls tighter around himself. He’s lost all the sulky anger, and now his face is clearly showing regret, discomfort, guilt. Castiel can almost see it eating at him.
“Okay,” Dean finally gasps, jerking up to his feet. He knows where the switch is in this room already, Castiel knows, and he goes and fetches it without any more delay, and brings it right back, his head hanging.

Castiel takes it from him with a nod. “Thank you. That was a good choice, Dean. You will take five on your anus and five on your bottom, and perhaps this lesson will last longer than the last one did.”

Dean’s eyes snap up to meet his, wide and horrified. “Five? Sir! That’s too many!”

“This is not a democracy and you do not get to vote.” Castiel puts a hand on his neck and turns him. “Over the chair arm. Spread your cheeks.”

“Sir, please!” It’s a frantic sob, Dean’s eyes are suddenly wet and his face has gone pale. “You can’t! Please! Don’t!” There’s the fear that Castiel has been missing from the last few times he’s punished Dean. He is accustomed to hardship, painful circumstance, and has a toughness few can match; for punishments to even register, Castiel will have to keep them fresh.

“I will tie you down if I must,” Castiel coolly informs the boy, who is still resisting being bent over. “You won’t enjoy what happens if I do.”

“Nooo,” Dean sobs, but caves. He bends reluctantly over and shaking hands pry his cheeks apart behind him. His little hole is clenched so tight Castiel can barely see it.

Castiel braces his knees between Dean’s legs, against the side of the chair, to help hold him in place. He holds the tip of the switch about an inch from Dean’s quivering hole, and using the other hand, bends it carefully back. When he releases it, it snaps forward and impacts with a small *pop*

Dean screams, high and shrill, and his thighs try to clamp closed, his body jacks upwards as he convulses.

“Hands back where they were,” Castiel commands him calmly, pressing him back down. “Hold yourself open for your punishment.”

“Nonnonono,” Dean blurts into the fabric of the chair, twisting and shaking even as he obeys, “nomoreplease,” and Castiel positions the switch and releases it again. The reaction is even stronger this time, Dean’s shriek and the twisting buck of his body.

“Three more,” the fight and resistance is draining out of Dean with each strike, he’s going soft and defeated. “Now, Dean.”

“Sir,” Dean sobs, “I’m s-sor-ry, ss-orr-y sir,” his hands are trembling so hard that he can barely hold his cheeks apart.

“I know, sweetheart.” He lets the tip of the switch snap free. This time Dean almost climbs off the chair completely, and Castiel has to hold him in place as he kicks and strains. With the fourth, he holds still but the scream lasts twice as long, and the fifth and final has him shuddering all over and his hands scratching at the chair, digging, as he sobs wildly.

“Now five on your bottom,” Castiel knows better than to let too much time pass between stages. “It will be over soon, baby, you’re doing so well.” He pushes his thigh against Dean’s hip, supporting him in place as he lets the switch fall hard and fast, five swift strikes on Dean’s high, round, quivering rump. As soon as the last one lands, he releases Dean and turns to the chair, getting a hip into it and sliding the wailing Submissive into his lap carefully.

Dean is a mess, face wet and blotchy, mouth open as he sobs unrestrainedly. The guilt and shame from before are gone, though, and he turns against Castiel and curls into his arms without hesitation.

“There, sweetheart. My good boy. That was much better, so well done.” Castiel soothes him with words and hands and his voice, gentling him until his breath evens out into small hiccups. He’s sitting awkwardly even in his lap, though, hips cocked and legs spraddled. His hole must be burning fiercely, Castiel thinks with no small satisfaction.

“F-feel better,” Dean confirms after a long moment. His voice is small and wet with tears.

“I bet you do. You had yourself in quite a temper. I know it’s hard when we have plans and they change without warning, but you must learn to moderate yourself. These things are bound to happen.” He kisses Dean’s mouth, nipping at his full lower lip. “Good boy.”

“Thank y-you, Sir.” Dean manages a smile for him, and it’s sweet and reaches his eyes. “Sorry.”

“You are completely forgiven. Now do you want me to help you down to Benny’s room? It’s nearly time.”

Dean winces, shifting. “Do I have to?”

“Yes, baby. We’ll tell him you were whipped, I’m sure he’ll be gentle.”

“It hu-hu-hurts,” there’s still a bit of a hitch left in Dean’s voice, and it definitely makes itself heard as Castiel eases him to his feet and gets him walking slowly.

“It wouldn’t be a very effective punishment if it didn’t. And now you’ll have your enema all nice and submissive, instead of knotted up in a temper and cranky.” Castiel smiles at him. “Benny doesn’t like punishing Submissives, so he makes sure it’s very very severe and memorable when he’s forced to do so. Something to remember tomorrow.”

“I don’t like submitting to other people,” Dean confesses as they walk slowly together. His head is down. “It was okay with Meg, I guess. But it’s so much better with you.”

Castiel can’t even bring himself to reprimand the boy, or contradict him. It feels too good, hearing that. He bites his tongue, and just contents himself with running a gentle hand along Dean’s shoulder.

“A limping Sub and a supportive Dominant,” Benny muses from his desk as they come through the door. He looks like he’s making notes for something, but he stands up to meet them. “I’m guessin’ that means a certain young man got himself into some trouble?”

“Correct,” Castiel confirms, smiling at him as Dean practically scuffs his bare feet in shame. “Dean just had his hole whipped quite strictly for rudeness, so I helped him down to you. Mostly for moral support, to be honest.”

“Ouch. Couldn’t have given yourself even a few hours before you came down here, eh?” Benny looks at Dean, who sighs.

“I wasn’t really thinking, honestly.”

“And that’s obviously the truth,” Benny laughs, as Castiel chuckles.

Dean just winces, then looks at Benny apprehensively. “Is it going to be awful?” he asks.

“It won’t be sunshine and roses,” Benny admits. He glances at Castiel and gets a nod. “Let’s have a look at the damage, cher. Just lean on the table, up on your elbows, spread ’em wide.”

Dean does, and Benny puts his thin gloves on, and rubs lube generously over his fingers. “All right,” he warns. “Boss, can you open him a bit?” Dean’s tense enough that his cheeks are clenched tightly.

Castiel gently pulls them apart, and Dean hisses, then yelps as Benny prods at his red, angry-looking hole gently, smearing it with slick. He actually squeals, going up on his toes, when Benny pushes his fingertip in, lubing the entrance, then withdraws.

“Very sore and tight, which I’m sure you know,” he reports, stepping back. Castiel releases his cheeks, and Dean pants down against his forearms. “Nothing too much to worry about. Releasing will be the big challenge, since he won’t want to relax, but we’ll manage it. If he tries to get retentive, I have spreader plugs and such.”

“I could fuck him open for you,” Castiel offers, feeling the idea ignite heat all through him, even as Dean whimpers. Benny looks thoughtful, then shakes his head.

“He’d tighten up again during the enema fill. I think we’ll be all right. You mentioned that he’s getting dependent?”

“Yes.” Castiel strokes Dean’s back, long soothing sweeps with his hand. “I’m watching to be sure he’s well hydrated, but he hasn’t had a bowel movement in nearly five days, besides the enemas.”

“With daily cleanses, it can happen easily, and it’s quickly enough reversed if you want.” Benny’s busy with the stand and bag.

“Talkin’ about me like I’m not here,” Dean grumbles, obviously recovered from Benny’s probing.

“You just relax, cher, and get up on the table. On your side, get comfortable.” Even with the waterproof medical cover, the padding is noticeable and thick, and Dean crawls up eagerly with Castiel’s help, curling up on his side. Benny clearly believes in ripping the bandaid off; before Dean is even fully settled, he slides the long enema nozzle in between his cheeks, and with a twist, into his hole.

“AHHHH!” Dean arches back, jaw locked and clenched.

“Easy, lovely, relax,” Castiel hums. “Good boy.” He’s so gorgeous like this. Castiel’s trousers are getting tighter by the minute. Soon both of them will need help walking anywhere.

“I’m running the flow a little quick,” Benny warns, more to Castiel than Dean. “It will help strengthen the urge to release. Try to take it all, little man. Breathe deep.” One hand resting on Dean’s belly, the other massages at the root of his limp cock, urging relaxation.

“Ow, ahhh, ow ow,” Dean whines, hips twitching a little as he tries to adjust and accept the warm water.

“I’ve been trying to think of a way to fuck him when he’s full,” Castiel mentions to Benny, watching the boy squirm with hungry eyes, “but the bathtub is too cold and hard, and the mess is prohibitive elsewhere.”

“Sir,” Dean gasps, craning his neck to stare at him in shocked disbelief. He does so love watching those green eyes go wide and bewildered like that.

“Do it outside,” Benny shrugs. “Clean him out first, then bring another bag and stand out to the lawn. You can fill him up out there easy enough, and if you prefer an audience, it’s ideal. It’s a sensation not to be missed, I’m sure you know.” He rubs Dean’s abdomen soothingly.

“What? No...you can’t…”

“I think you’ll find that he can,” Benny says him plainly, as Castiel smiles. “It won’t harm you, cher, just be very full and uncomfortable. All right, that’s the whole bag.” He locks the nozzle and works the nozzle back out of Dean. This time, when he massages Dean’s stomach, sides, and lower abdomen, his hands are stronger, more forceful, and Dean’s eyes flutter closed as he struggles to process the feelings in his body.

“I want to be sure everything is expelled in the first release,” Benny tells Castiel, as Dean gasps and tries to rock back away from his hands. “After that he’ll tighten, and it’ll be a lot more difficult. I know, little brother. It’s not as sweet and quiet as we usually do,” he croons to Dean, who shakes his head with his lower lip clamped between his teeth. “But if you don’t clean out, I’ll have to put a big dilator plug in you, and that will be a lot more uncomfortable than this. Work with me a little, deep breaths. We’ll take care of you.”

Dean is sweating hard by the time he’s allowed to move to the toilet, and he howls through gritted teeth as he releases. The relief on his face after is beautiful to see, though, and his whole body relaxes completely enough that he barely squirms when Benny rinses him out one last time with a slim shower attachment in the sitz bath.

“There,” Benny says with satisfaction, once he helps a swaying Dean out of the bath and towels him dry. “Told you we could get it done.”

“I never doubted you,” Castiel smiles. “Before I take him upstairs, will he need any special prep tomorrow?”

“Just have him drink plenty of water, just a light lunch, and no bathroom breaks for two hours before. “ Benny grins at him and hands Dean over. “I have some things planned and I’d hate for him to not experience them properly.”

Jealousy surges through Castiel in a hot flash...his own medical kink is powerful, and the idea of Dean discovering it with Benny, not him, exploring it under hands other than his own, these ‘things’ Benny has planned...but he fights it back. This is the whole point of pushing Dean’s training out to other Dominants, he tells himself sternly.

“I’ll be sure of it,” he answers Benny. “Thank you,” he adds, sincerely. Tonight he'll reinforce his claim on Dean, and tomorrow Benny will explore a new kink with him. It's for the best, Castiel tells himself.

Chapter Text

Dean isn’t too proud to admit he spent his kneeling time with Sir basically clinging to his leg, even as Sir was telling him stuff about medical kink in response to his questions. He likes Benny fine and his enemas are usually awesome, but this feels kind of intimidating and new and honestly, he’s still not sure how he feels about Submitting to anyone but Sir anyway.

But Sir sends him off to the training room firmly, with a swat to his backside and an order to behave, so Dean goes.

The medical room off the training room is smaller than the age play room, but it’s still pretty big. It has a table-chair thing (with stirrups) and a counter with all kinds of instruments, and a scale, and sinks, a toilet, none of it too scary. But everything looks sterile and washable, and Dean hesitates in the doorway, even though Benny’s right there, pulling one of those paper sheets down the bed.

“Come on in,” Benny’s clearly noticed him. He looks normal, smiling, relaxed, and that makes Dean relax too, at least a little. Benny’s wearing normal clothes, too, his blue scrubs, and it’s familiar enough that Dean smiles back and goes right to his side.

“Did the bossman tell you I’m a registered nurse?” Benny guides him to a scale and actually takes Dean’s weight, which is kind of funny. “It’s true. I have a license in Texas and I specialize in Submissive medicine. But I’m technically the house nurse here.” He makes a note and then waves Dean to a seat.

“Seriously?” Dean grins at him as he gets out the blood pressure cuff. So far this isn’t any different than a regular visit to any old doctor. “So all this is legit?”

“This is actually doubling as your two week health checkup, even though it’s a little overdue,” Benny smiles back and pumps up the cuff. “I started working for Novak Corp as a nurse, but then the boss saw I had a good way with some of the Submissives that came in. He taught me a lot, and here I am. Pulling double duty, so to speak.” He loosens the cuff when he’s done, and puts it away. “And helping out with security, too. Little bit of everything, that’s me. Okay, cher, up on the table.”

The paper is rough under Dean’s bare ass when he slides up, and Benny rolls a little cart over. Dean eyes it nervously.

“You’re twitchier than a black cat on Halloween,” Benny chuckles. “Here.” He reaches up and adjusts the bed, so that the back comes up. “Lean back a little.” Dean does, and finds himself relaxing instantly. “That’s better. Now scoot your hips forward right to the edge. Nothing strange yet, brother.” Trustingly, Dean does, and Benny moves to stand right between his legs.

“Now, I’m not into pain, like some Dominants,” Benny starts, and his gloved hands run up the insides of Dean’s thighs until they reach his groin, where he moves them, pressing here and there. “Nothing much today should hurt, though it’ll be intense. So just like with the enemas, I want you to breathe nice and deep, and relax. I’ll help you as much as I can, but I need you to be real good for me.” His thumbs find the Angel glands at the base of Dean’s cock and rub there, a gentle circular motion.

“It’s just new,” Dean breathes, as the warmth spreads through his hips, the muscles easing and loosening. He sighs, and his legs relax, too. “Don’t really know what to expect, even though I asked Sir about it.”

“Well, he does medical kink one way, and I do it another, just like everything, everyone’s got their own style.” Benny’s got a little Dominant rumble going in his voice now, and the harmonics of it soothe Dean even more. “But the core of it is the same, which is that you submit to the kinds of examinations and procedures you’d normally get in a doctor’s office.” He stops rubbing, and pats Dean’s belly.

“I figured that much out,” Dean would roll his eyes but he feels too nice right now.

“Sometimes it goes further. Getting to know someone inside and out, all the ways their body works, it’s an intimate thing, cher. Okay, I’m going to get a temperature now, and finish the regular exam.” Dean opens his mouth for a thermometer, and Benny snickers at him.

“Oh, it doesn’t go there.” The thermometer he holds up is long and sturdy-looking. “Much more accurate, anally. I’ll just slide it right in--” A small pinch of pressure and cold, and Dean’s eyes go wide, “and you hold it there.”

“Okay,” Dean breathes. That’s unexpectedly sexy. He can feel the little thing inside him, just sitting there, reading him, as Benny moves to his side. He has to clench to make sure it doesn’t slip out.

“You have any soreness here?” Benny’s kneading around one breast, moving in towards the nipple as he goes.

“No. Sometimes? If, uh,” Dean flushes. Benny’s fingers are sending that warm lassitude through his chest and shoulders.

Benny just nods. “If you’re not put down on your front enough. That’s natural, just your Angel glands doing what they do. It’s why you’ve got a little swelling, too. I’ll mention it to the boss, to be sure you get a chest support for when you’re paddled or training. That’ll set you right.” He moves to the other side, does the same, checks Dean’s ribs and stomach, his throat. Even makes him open and say ahhh.

When he slides the thermometer free, he leaves his fingers at Dean’s hole for a moment, rubbing and stroking, as he checks the reading.

“You’re a very healthy young Submissive so far,” he announces with a smile. “Congratulations.”

“Thanks,” Dean grins back.

“Did you listen to the instructions? Light meal, no bathroom breaks?” Benny’s pulling out the stirrups, and what look like knee supports, and Dean sucks in a breath when he takes one leg and just...bends it up and out, sets it there, so easily. Just like that, Dean’s spread wide open. His heel snugged into the stirrup, knee up on the brace, and Benny fastens a strap there too. Then the second leg. Dean can feel cool air brushing hot skin between his legs. He’s never felt so exposed in his life, and he can’t believe it, but his cock gives an excited little twitch.

“I did, I didn’t, I mean, yes, I followed them,” he babbles, knowing his face is scarlet, he can feel how hot his cheeks are.

“Good, that’s good. I know it might be a little uncomfortable, but a full bladder is important.” He winks at Dean. “And if you need to let it go at some point, I won’t mind at all. I’ll think it’s a compliment, actually.” He’s doing something with the instruments on the little rolling table, and Dean cranes to see, his hole clenching nervously in the cooler air of the room.

“I’m not gonna pee myself,” he says indignantly.

“Don’t make any promises,” Benny warns, and pulls over a rolling chair. “Okay. How are you feeling. Still relaxed? Still breathing nice and deep?”

“Kinda nervous,” Dean admits. He has to look down his own body to see Benny, between his spread thighs.

“No need to be nervous. I’m gonna take wonderful care of you, cher. Just relax and let it happen. First thing, I’m going to do an internal sonogram. I’ll put a wand deep inside you, and it’ll give me a picture of your insides.” He holds up a fairly substantial white cylinder, wired to a machine off to Dean’s side. Dean swallows.

“That’s...big.”

“It is. And to get a good picture I need to move it around, so I’ll be opening you up nice and wide, first.” Benny’s voice is calm, soothing. He’s not asking, though, he’s telling, and somehow that settles Dean. He doesn’t get to say yes or no, here. “I know you’re very tight, normally.” His slick fingers are at Dean’s hole, prodding. “You snap right back after any kind of stretch, which is very nice, a sign of a good strong muscle. I’ll be using a spreader for you, to keep you open.” Even as he’s working lubricant into Dean with one hand, he has something long and silver in the other.

Sensations are rocketing through Dean already. Fingers in him isn’t something he feels a lot; Sir doesn’t do it, and Benny only briefly before his enemas. They’re thick and forceful, and they move a lot, rubbing and spreading, like an itchy stretch. Spread like he is, he can’t even squirm, so he just lets his head fall back as he tries to breathe through it. He feels all wet between his legs from the lube, and so vulnerable already. Squirmy. His cock his half-hard on his belly.

“Deep breath, little brother.” There’s something cold and metal in him, in his hole. It slides in without resistance, even though he reflexively clenches. And then there’s a click, and he feels it push, side to side. Another, and he spreads another bit wider.

“Oh my god Benny,” he gasps, his hands reaching down.

“No, cher, you hold still,” Benny says, sweet but firm. “Do you need me to tie your hands? I would normally but I know being tied can be a lil’ stressful for you.”

“No, no, that’s okay.” Dean puts his hands flat on his own stomach. Feels his own breaths coming fast. The stretch isn’t painful, exactly, but it’s so strange. Rigid. The metal is pushing him apart and it’s unyielding.

*Click* Another degree wider. He whines in his throat. That one hurt, the delicate skin stretching hard.

“Okay, little break. I’ll take a look around while you adjust,” Benny tells him. A finger, inside, past the hard metal thing, stroking his soft, vulnerable inner walls, left wide open. Dean realizes his legs are shaking at the same time as the finger touches his angel gland directly. Not squeezed against it, not rubbing it, just touching it, like someone would brush a nipple.

“Fuck!” He curls up at the feeling, but Benny’s big firm hand is right there on his abdomen, pressing him back down.

“Okay, honey. I won’t tie your hands, but I can’t have you thrashin’ around and hurting yourself.” Leaving the cold spreader, the bars dangling down and pressing against Dean’s cheeks, he stands up and moves to the side of the table again. He pulls up a wide, softly padded strap. “This is a belly-band. You can hold onto it if you need to, and it’ll keep your body nice and still for me.”

“Uh..I...okay,” Dean manages. Benny’s face is kind, like always, but his eyes are dark and intense, his voice still deep with the Dominant burr. Dean can see how hard he is in the scrubs, too, his erection a long bar right there that presses against Dean’s arm as Benny moves to draw the band over Dean’s body, right below his navel, drawing it snug, and buckling it tight.

It feels like a warm security blanket. Dean immediately relaxes some, when the band presses his lower body down. His hands are still free, but he can’t move his hips at all.

“That’s better, eh, cher?” Benny smiles down at him, and strokes his cheek gently. With a shock, Dean realizes he’s half into subspace already, the way he turns into the hand like a needy slut, the way he’s making soft little noises without realizing it, the soft drift of his thoughts, all signals he’d missed before.

“Better,” he sighs in agreement.

“You’re real pretty inside,” Benny soothes him. “So pink and soft. Can’t wait to get my sonogram up there, my camera. We’ll make sure you’re real healthy.”

That sounds good to Dean, so he nods.

“Gotta get you a little more open,” Benny returns to his chair. “This spreader opens to six inches, but I think today we’ll only do four or so.”

Dean’s breath catches in his throat, the dull burn of his ass leaping to the front of his mind again. Six inches is so much, so big.

*Click*

“Hnnnnn!” Dean tries to arch, but the bellyband holds him still.

“Shhh, easy,” Benny says. “You’ll be fine, sugar. One more, you breathe, now.” *click*

“Ohmygod.” Surely his insides will fall out. Surely there’s nothing left holding him together, he must be open wider than his hips now. He can feel cool air inside him, delicate tissue exposed to the air for the first time. “Benny, Benny,” he begs, his hands clenched hard on the bellyband, all the muscles in his legs rigid as his body tries to clench anything it can against this alien feeling.

“That’s real good, that’s enough,” Benny responds. “I’m gonna get the wand up into you now. You remember, this will feel strange, but it won’t hurt you, cher. Just a lot of intense sensation and pressure. Think about your cock, it’s enjoying this. Focus on what about it makes you feel so good.”

Dean is hard, he realizes with a shock. And the stretch isn’t painful, just so weird it’s freaking him out, but the strangeness is part of the goodness. He’s panting, but tries to slow his breath, so when the first cool intrusion of the sonogram wand makes itself felt inside him, he almost chokes.

Short, smooth thrusts move it deeper and deeper into him, as he stares blindly at the ceiling, completely immersed in what’s being done to his body.

When it pushes against his bladder he moans. Benny chuckles. “There’s my picture,” he says, almost to himself. “Very nice, Dean.” Then he starts moving the probe tip around. It’s rooting around inside Dean, moving back and forth, gently, even up and down.

“Nice, healthy seminal vesicles,” he narrates. “If I can get down a little...yes..there’s the prostate. I’m very glad your bladder’s so full, or I couldn’t see half of what I want to.” He is looking off to the side as he pushes the wand around, to some screen Dean can’t see. He moves it forward a little and suddenly things get urgent.

“Stop stop I’m gonna piss myself,” Dean blurts. He can’t close his legs, can’t sit up. His cock is still half-hard so he doesn’t even know how it will happen but he knows it’s coming. It hurts, how bad he has to go, the pressure inside is suddenly absolutely overwhelming.

Benny doesn’t stop. He smiles at Dean and slides his chair back a little but that’s all. “I have a good sonogram, nice shots of everything I need. You go ahead, cher.”

“Noo,” Dean whispers, every muscle in his abdomen tightening as he fights to hold it in. But Benny keeps moving the probe, hard little prods and it’s futile. He starts to pee and just like always it feels incredible, the first release like heaven, but now he’s naked and spread and there isn’t even a diaper. He’s just wetting the crease of his own thigh, feeling hot liquid trickle down. Then the dam breaks and with a sob he lets go completely, what feels like gallons, a huge spurt that there’s no way he can hold back..

“Oh god oh god,” he’s chanting, eyes closed, face turned away, before he realizes Benny’s stroking his belly, the probe isn’t moving anymore, it’s out of him, Benny’s rubbing his angel gland, he’s relaxing, so even though his eyes are hot with shamed tears he’s feeling so relieved and good. The relief is exquisite. As the heavy stream finally slows, he slumps back, drained and boneless.

“What a star you are,” Benny’s crooning to him. “Gotta get that out of the way, Dean. Gotta get it over with so you can let it go, stop worrying about it. Nothing to be ashamed of, just your body being a body. You did real good, brother, I’m proud of you. Looked so pretty, too. Feel that?” He takes Dean’s hand, presses it to his crotch. His cock is like iron, hot and solid under Dean’s palm. Blinking, Dean stares at him, and manages a small, hesitant smile. “That’s right.”

“But the mess,” Dean tries.

“Not much of one, and this room cleans easy,” Benny assures him. “Felt good, right?”

“Yeah,” Dean breathes.

“Holding it that long isn’t good too often. It can stretch out your bladder, lead to problems later, even maybe lead to infections and worse. But once in a while it’s worth it.” Benny takes his cock, still wet, still half hard, in his gloved hand. He fondles it a little as Dean flushes wildly.

“We need a sample to be sure your daily enemas aren’t disturbing your gut flora,” he adds, gently. “While you’re spread nice and wide and still stretched from the sonogram. It’s for your own good, cher, so you be a good boy.”

“What?” Dean struggles a little against the hazy distraction of the hand on his cock, the aching stretch at his hole, the lingering shame of his accident. “What sample, what…”

“I’m going to get way up inside you and get a small stool sample. Shh, easy,” Benny gentles him immediately. “This is important, you’re dependent on the enemas now, so we need to be absolutely sure you’re still healthy while getting them so regularly.”

More hot tears prickle his nose, but maybe Benny was right about getting it over with, because after the earlier accident, he just can’t muster up any resistance to this new thing. He nods, eyes closed.

Honestly he barely notices it happening. He’s so stretched that Benny’s hands between his legs, the long, slim instrument he uses, barely register. There’s a funny feeling in his lower abdomen, and then Benny’s telling him he’s good, and it’s over. He breathes deep.

“I’ll leave this inside,” Benny holds up a curved silver prong, with two smooth nubs and a long, curved base that will cradle him front to back. “It’ll give you something to squeeze down on, make you feel nice as you close back up.”

He gently, slowly clicks the spreader shut, and then slides it free, setting it aside. Dean feels gaped, loose, wobbly. Like nothing is where it should be, behind his balls. Even as his sphincter tries to squeeze, it just spasms weakly and fails to close.

“Give it a few minutes. It needs to relax again from that kind of wide spread,” Benny says, and gently cleans Dean with a soft cloth and soap that smells crisp and herbal. It’s a clean and refreshing smell, and cuts through the fugue he’d fallen into a little.

He blinks. His legs feel rubbery, and he’s glad they’re strapped to something. He realizes he’s sweating, his whole body a little damp. But it hadn’t hurt, not like anything he’d felt before.

“Here.” Benny’s holding a water bottle to his mouth, and Dean gulps it gratefully. He can’t believe just lying here like this is making him sweaty and drained like this, but when he says as much to Benny, he just gets a chuckle.

“I told you, it’s intense. Pain isn’t the only intensity you can feel, or even pleasure. Some things are intense in other ways, and this is one, hey?” Benny smooths his damp hair off his forehead. “How are you doing, little brother. You feel good?”

Dean smiles up at him. “Real good, yeah.”

“That’s what I like to hear. Now, since this is your first time, we’ve only got one more thing to do. Do you know what this is?” He holds up a thin, straight piece of metal. Dean shakes his head, wide-eyed.

“This is called a sound. It goes inside your cock.”

“Inside my what?” Dean asks, faintly.

“You heard me,” Benny teases. “Sugar, if your body has a hole, someone out there has figured out a way to put something in it and tease and torture you with it. Now this isn’t going to hurt either. We’re starting real small, just a little stretch. This one won’t even reach your prostate. But there’s a chastity cage that it fits into just right, so if the Boss wants to lock you up in more ways than one? This can click right into place.”

Dean feels a little dizzy. “How do you piss? Or come? Or anything?”

“You’re already askin’ permission for all those things anyway,” Benny waves a hand. “Just a little extra step, is all. And like I said, it feels pretty good. You have all kinds of nerves in there.” He takes hold of Dean’s soft cock, and Dean jolts at the touch; he’s feeling extra sensitive right now, like all his nerves are fizzing, and even though he’s soft, every touch feels magnified.

“Easy.” Something hard teases at the opening at the head of his cock. It’s utterly alien, and strange, to feel that tiny hole prodded into opening wider.

“Fuck,” he gasps, as an inch or so slides in.

“That’s real nice, cher,” Benny hums to him, bent over his groin, both hands moving carefully. “I’m using plenty of lube, so...ah.” A burn, more alien stretch, and something moves deeper inside Dean, where nothing’s ever been before.

He realizes his hands are clenched and he’s panting again, even as Benny starts rotating the little metal rod. It’s a pulling, stretching, throbbing sensation, like an orgasm half-finished without ever starting or beginning. Dean can’t get his mind wrapped around it.

“Oh oh oh,” he chants, legs trying to close, pulling against the restraints.

“Breathe, relax, I know,” Benny says again, and the little rod goes deeper again, and Dean goes limp with a gut-deep moan. He can feel his cock trying to harden, but all his signals are confused. It feels like his cock is being stroked, from the inside, which is just backwards.

“Okay, it’s all in,” Something cool and solid fastens around the head of his cock. “There’s a little ring to hold it in place. I’m going to let you get used to that, while I clean up a little. Just take some breaths, let it flow, let yourself adjust.” Benny strokes his thighs, his belly, the cheeks of his ass, and all the touches help him feel the rest of his body again, get himself centered so he can get his bearings.

When he glances down, nervous, there’s just a little metal ring around the tip of his cock, with another metal piece curving up and then, something going down inside. But it looks so normal. He’s half-hard, but there’s no way to tell there’s something inside him.

When he tenses and shifts, he realizes he’s tightened up again, and that dildo thing Benny had left in him is rubbing him in nice places, too. Another distraction. He bites his lip, and squirms again. He hears Benny turn off the water at the sink and chuckle.

“I see you’re enjoying yourself. And closing up again nicely, too. You’re an excellent patient. I think, for therapeutic reasons, I’ll leave the stimulator and the sound in for the next few hours.” Dean cranes his neck to see him as he comes around, casually patting Dean’s knee, his thigh, then standing between his legs again. He starts to carefully unfasten the straps holding Dean’s legs in the stirrups.

“Is it safe for me to walk around with this thing?” It’s a worry. Every time he moves, he’s reminded that it’s there.

“Completely,” Benny assures him. He finishes unfastening, and gently lifts Dean’s feet out of the stirrups, setting his heels back on the bed, so his legs don’t just dangle. “Since you’re all lubed up, I have special briefs for you to wear for a few hours. It will keep you from making too much of a mess, with the leakage.”

“Whuh?” Dean’s still trying to cope with how it feels to have the stimulator moving inside him, the little nubs rubbing his prostate and his angel gland, at the same time as the sound in his cock shifts with every motion he makes.

Benny urges him to slide back again, get more comfortable, and sighing with relief, Dean does. He can feel himself get a little shivery now, some kind of reaction, and when Benny slides onto the medical table with him, he leans into his warmth with a happy sigh.

“Briefs,” Benny answers, like there hadn’t been a delay. “They’re normal after a medical scene. I used a lot of lube, and it will be coming back out for the next hour or so. You’ll need to keep them on, it’ll stop you from making a mess.” He reaches out a long arm and snags a white thing off his little cart.

Dean looks at them. “I’m not wearing those,” he says flatly. “They look like maxi pad granny panties.”

Benny chuckles, shaking his whole body. “Afraid you will be, Dean.”

“No way. I’ll just sit on the toilet or something. Those are way too embarrassing!”

“Dean.” There’s a rumble in Benny’s voice Dean hasn’t heard before, and he’s not laughing. His arm is snug around Dean’s waist, and gives a little squeeze. “You’ll be puttin’ these on, like a good boy, and coming back into the house. The boss plans to have dinner with you just like normal.”

“I’ll just put a pair of panties on,” Dean tries.

The arm around him turns to steel. Dean tries to squirm, but he can’t even move, not with his current leverage.

“I don’t like punishing Subs,” Benny says calmly. “I’m more of a kill ‘em with kindness guy. I like things gentle, calm. But don’t you think for one minute that means you can disrespect me, or disobey me when we’re in a scene like this. I will beat your lil’ ass black and blue, do you understand?”

Dean’s breath hitches. Benny’s this big, friendly bear of a guy, always has a smile, but right now, it’s like leaning on a steel wall.

“Yes, Benny,” he says. Meekly, damn it, that Dominant voice is doing things to him, and also, he’s still kind of wrung out from before. He even feels his chin dip, but he really doesn’t want Benny to punish him, and he can tell the big man means it. Right down to his bones.

“That’s more like it,” Benny approves. He relaxes, arm around Dean all soft and nice again.

Dean hates the briefs. They’re very snug, and hold his cock against his body and the stimulator pressed firmly into him, and they’re plain white with thicker parts between his legs. High-waisted, he just knows he looks ridiculous, but with Benny’s eyes on him, he doesn’t dare do more than sigh resentfully about adjusting them carefully.

The sound still tugs at his consciousness, but with the briefs cradling him firmly, there’s much less shifting going on. He guesses that’s an okay side effect.

“You did real well, Dean,” Benny tells him proudly, helping him with the first few wobbly steps he takes, hands on his waist, supporting him. “Now let’s go find Dr. Novak. I bet he’ll be glad to hear how good you were for your procedures, how well you submitted.”

He’s happy to have pleased Benny, but the idea of Sir’s praise has Dean lighting up inside. He grins and nods, and follows Benny out the door.

Chapter Text

Dean’s favorite thing about their bathroom is definitely this tub. It’s big enough for two, and when he’s had a long day, or Sir is feeling tense, they often share it, relaxing and bathing together. Right now, he’s leaning back against Sir’s chest, and Sir is gently playing with his cock, just casually toying with it. There’s no purpose to it, he knows. Sir had teased and tortured him with the sound for over an hour, earlier, and even now that it’s gone, he seems to want to keep touching Dean there, which Dean is more than okay with.

Especially with how Sir’s hard cock is all snugged up between Dean’s cheeks, like he’s riding it, even though they’re just sitting still right now.

“How did you even get started doing this?” he asks idly, watching Sir trace some complicated pattern over the solid, wet head of his cock under the warm water. The little shivers running through him are strong enough that he needs some distraction.

“Oh, that’s a long story,” Sir’s deep voice is amused, over his shoulder.

Dean shrugs a little. “I don’t have anywhere else to be?”

“All right.” Sir shifts a little. “Well. My brothers and sisters and I...hmm. Our father is very powerful. We all had plans laid out for our careers, our lives, pretty much from the beginning.” He runs a washcloth gently over Dean’s shoulder, leaving his cock alone for now, and Dean isn’t sure if he should celebrate or mourn that.

“Sounds kind of boring,” Dean comments, into the silence. It feels like Sir is speaking carefully, choosing his words.

“It was definitely...structured,” Sir agrees. He drops the cloth back into the water, does the other shoulder. “Then he disappeared. This is quite a few years ago, now. And for a while, most of us carried on with the plan, just as though nothing had changed.” Apparently done with the cloth, he gets his hands back between Dean’s legs, but one cups his balls, now.

God, it does something to Dean, the way Sir just...handles him. So casually, matter of fact, like Dean’s cock and balls are there simply for his amusement. Which they kind of are, Dean realizes, through the daze of lust. Sir could literally do this any time, any where, for any reason. Just because he feels like it.

“A-and then what?” He gasps out. His cock is so very hard, not so much from the touching a the thinking about it.

“Well, a few years ago, things changed again, drastically. Something happened, and as a side effect. Well, let’s just say we all got a look at what the future might hold if we went on the way we were, just keeping to the plan with the family business. So we sat down, and discussed it. How we might do different things, go a different way.”

“What even is this family business?” Dean’s curious enough to ask.

“Not really relevant anymore.” Sir tugs his balls, just a little yank, and Dean sucks air through his teeth. “One of the things we’d all noticed was the way dynamics weren’t quite as healthy in a lot of the population as they could be. A lot of failing marriages, broken contracts, despite the fact that Submissives have so many more legal rights, as you should. And the idea for the training schools was born.” Dean can’t see Sir shrug, but he can feel it. “And here we are.”

Dean twists a little, wanting to see his face.

“I know Gabriel, how many brothers and sisters do you have?”

“Quite a few.” Sir’s damp with the steam and the hot water, his cheeks are pink, and he looks completely delicious. God, Dean wants him so badly.

He’s pretty sure Sir can tell, by the way his lips curve up.

“Do you like it, being a trainer? Don’t you want to find someone just for yourself?” Dean’s feeling bold today, or maybe just very bare, opened up by the medical scene, by the way Sir has been with him since Benny brought him back, how much touching they’ve been doing.

“I do like training. I very much enjoy helping someone find their true Submissive self, what fulfills them, what will help them,” Sir answers. He tugs at Dean, turning him back away so his hands can roam freely again. “And it’s fun getting to know different people. I’ve made wonderful friends.”

“So that’s a no on finding your own Submissive,” Dean prods. He wriggles a little, getting the hard shaft of the cock between his legs a little more firmly nestled against him.

“I am generally...fulfilled by my training role,” Sir answers, after a pause. He sounds careful again. “I have not found it necessary to look for a personal relationship outside that.”

“Doesn’t mean you don’t want one,” Dean points out, trying to sound wise, which is hard when a gorgeous, wet Dominant has his hand on your cock.

“You are a very impertinent boy,” Sir scolds, laughing a little. “Has anyone told you that?”

“I think you did just yesterday,” Dean grins. “But not one of the, what, hundreds of Subs you’ve trained was just perfect for you, huh? So you’d stay together, after?” He’s almost holding his breath when he asks, which is so stupid, he knows he’s pushing, but he really needs to know.

“Hardly hundreds. Dozens, perhaps. And Dean.” Sir tugs him in closely, now holding him in an embrace. “It’s a very strict Novak Corp policy that trainers and trainees do not enter relationships together. I put the policy in place myself, with the rest of the board.” His voice is tight with something Dean doesn’t recognize, can’t, through the blood rushing in his ears. “It’s common, almost universal, for intense temporary bonds to form during training. It wouldn’t be ethical or right for any professional to leverage that bond into a personal relationship beyond the contracted time. Otherwise, it would be easy for detractors to say we were just a group of Dominants hunting Submissives, or that our Submissive staff were trapping Dominants in need.”

Okay, fine, so maybe Dean has been building a little fantasy in his head. Where Sir looks at Dean one day and stops talking about these other Dominants and Dean finding someone else after training is done, and invites Dean to discuss a real contract with him. Where he stays here for real, and maybe helps with the training somehow and definitely keeps hunting, and has a job, and Sam visits all the time. Where every night Sir breaks him apart down to his smallest pieces and then the next day puts him back together again in amazing new ways.

He can’t speak around the frozen feeling in his chest and throat, even though Sir is holding him and the water is still hot.

“Dean?”

His pride spurs him cruelly. He can’t sit here mute, like a pining Sub in some old-timey novel.

“So, uh, never? You’ve never had someone meet their one true whatever, at work, in any of your training centers?”

“A few times,” Sir says cautiously, and Dean wonders what his voice must sound like. “If they wait an appropriate time after training, of course, they are welcome to see and contract with whoever they please.”

“Right, got it,” Dean nods.

“Your numbers only settled this week,” Sir says, voice close to his ear. “I know it may feel like submitting to Paul tomorrow, and the other changes, are huge disruptions, but you are still early in your training, and this is all part of it. Don’t rush to anticipate the end, Dean. Think how dramatically your feelings and attitude changed from the day you arrived to now. Imagine how different it might be a month from now.”

“I guess,” Dean says, skeptical. The ice in his chest has loosened a little, though. “This Paul guy. He’s...he’s okay, right?”

“He’s definitely okay. He knows about hunters, for one thing.” Sir releases his hold, and starts petting Dean’s belly again, smoothing the wet skin under his palm. “I haven’t seen him for a few months, but he is one of our most experienced trainers, and spends a great deal of time with disruptive and aggressively reactive Submissives. He’s been sent detailed notes on your progress, so he knows all about you. All you need to do is submit, be a good boy for him, and everything will be fine.”

“Easy for you to say,” Dean grumbles.

“Not so’s you’d notice,” Sir mutters, but that doesn’t make sense.

“What?”

“Nothing. I’ll bring you to Paul tomorrow, first thing, after breakfast. I’ll introduce you, and leave you with him. We will check in on you throughout the day, to be sure all is going well.”

Dean’s head dips lower and lower.

“He’s not gonna tie me to a rack and leave me or something, is he?” Trying for humor and failing.

Sir squeezes him again. “He won’t do anything you haven’t already explored here, and nothing that has not gone well for you. You also won’t be punished beyond anything you’ve already experienced. You’re not being thrown to the wolves, Dean. This is intended to be a good, healthy, learning experience for you, not a trial.” When he pulls back and turns Dean to look at him, there’s concern in those blue eyes. “Are you not even a little curious about experiencing a new dynamic, exploring what Submitting to a different Dominant might be like? The excitement of someone new, with new ideas and even kinks?”

Dean scoffs a little, but softens. “Not...not really. But maybe once I meet him it’ll be different. It’s all just abstract right now, some stranger. I’m more a meet them face to face guy.”

Sir searches his face a little longer, then nods.

“All right. I think it’s best we get out of this bath before we become supersaturated. Since you were so good for Benny today, you get to choose for bedtime; stretcher and chastity, or no stretcher, and no cage?” Sir boosts him up with firm hands on his hips; the hot water has made Dean all relaxed and loose-limbed, and he practically oozes out of the huge tub.

“No stretcher, sir, please,” Dean chooses without even having to think about it. The dilator and stimulator earlier had left him feeling so strange and open and gaping, he’s pretty sure he didn’t like that. He definitely would prefer to feel every painful inch of Sir tonight.

“Good boy,” Sir hums, and Dean preens. “Dry off and get your paddle and wait, sweetheart. I’ll be out in a moment.”

Chapter Text

I apologize for the long and continued delay! I got the flu in January and it turned into pneumonia, moved to a new apartment in February when still very sick, and I am only just now starting to get back on my feet with any kind of normal energy. I had some writing done from after the holidays but It turns out writing with a high fever isn't a great idea, so the next chapter was totally terrible and had to be trashed and rewritten. But Stiletto isn't abandoned and I hope to post the (newly rewritten) next chapter sometime in the next week! Thank you all for being so patient and especially for everyone who has commented. I read all your comments and love them so much. - Beth

Chapter Text

“I just can’t shake the feeling that something’s not right,” Meg sighs, kicking back in her office chair and regarding Benny from across her desk. He’s as relaxed as she is, slouched on the couch. The afternoon in the house is generally quiet, and apart from check-ins on Paul and Dean, there isn’t much happening today for either of them to be concerned with. As the two other Dominants on staff, it’s sometimes nice to just sit and talk.

“Dean didn’t give you any sign, though?” Benny confirms again, and sighs at her nod. “He made eye contact, he wasn’t in subspace?”

“He wasn’t even close,” she snorts, and sits back up straight. “He looked bored, and a little annoyed. He was fine. Paul was fine. They were in the middle of an oral sex scene, and they paused so I could check in. The time before that, they were eating lunch and talking. It was just, the vibe of the room. I don’t know.”

“Maybe it was Dean being, ah, ‘bored and annoyed,’ giving you that feeling, Madame,” Benny grins at her. “I mean, you will owe me twenty dollars if the whole thing ends today because they can’t make any progress at all.”

“I’ve met Paul a few times. He’s not a quitter.” Meg doesn’t actually know the tall blond Dominant all that well, but she does know he specializes in some of the really difficult subs. Dean being resistant to subspace isn’t going to put him off.

“May well be, but our enfant terrible is something else. He doesn’t trust strangers any closer than the end of his fist. I don’t know what Castiel is thinking with this. You and me, bien, it’s fine. Strangers? The boy won’t take to it.”

“He’s gotta learn sometime.” Meg sighs. “It’s as much for Castiel as it is for Dean, too. You can see it, right? They have to get some distance.” She meets Benny’s eyes.

He sobers, and nods.

“Oui. Yes, of course. The rules being as they are, and Castiel being as he is... I understand it, Meg. I just don’t think it’ll work. Not this way.”

She shrugs again. Honestly, he’s probably right. But so is she. It’s a hell of a mess. And the worst of it is, everyone in the house adores Dean. He fits here, naturally and organically, with all his quirks. She can imagine him being here long-term, if it turns out that by some miracle he truly is sexually compatible with Castiel's Dominant needs. But violating the charter of the training organization would be catastrophic for them all.

“You have the next check-in on them, right? I was in there over an hour ago now, so you’re coming up before dinner.” She returns to the original subject, and he nods in response. “Just...take a little time, would you? Pull Dean out and get a one-on one. Get a feel for the dynamic, even if Dean doesn’t give the sign. Maybe I’m just reading the room wrong--”

A commotion somewhere else in the house cuts her off. It sounds like Dean’s voice, and then, is that Claudia? Almost a scream. Meg and Benny’s eyes meet, and they bolt for the door together in a rush. Through the television room and around the corner, down the hallway, up the back stairs towards the guest suites. They can hear Dean bellowing “SIR!” more clearly now. As they round the last landing, they nearly slam right into Dean himself.

He’s grinning like a berserker, eyes wild and hair not much better, a small cut on his cheek bleeding down his face. He’s naked, black leather cuffs ringing one wrist and both ankles, but they’re not attached; he’s dragging a bound, naked, cursing Paul Gudwin down the hall by his feet. Claudia has her hands clapped over her mouth, now, and looks to be frozen somewhere between hysterical laughter and shock.

“Where can I dump this fucking trash that threatened to take my eye out?” Dean asks, all manic swagger and cheer, and Meg suddenly feels an overwhelming desire for a vacation.

***

Castiel has been located, Paul has been untied, given first aid, and removed to an outbuilding under guard pending the investigation, Dean has been patched up and settled with Ash and the video game console, and Gabriel has been looped in on a video call, before Meg does so much as sit down.

“Has he sat down with one of you to explain what happened?” Castiel is pacing in his office, and Meg eyes him warily. She can almost see his wings mantling, and his teeth are showing, and there’s a feeling of heavy, dangerous static in the air.

“I spoke with both of them, but we’ll go over that once we’ve seen the video,” Benny steps in, interrupts Castiel’s angry course, and steers him to his chair. “The CCTV has it all. Even without sound, we’ll get some idea of what happened, and then we can speak with Dean. Here, some water.”

Thank god for Benny. He’s calm, big, steady, and even Castiel eases around him. He takes the water and doesn’t so much settle as perch, but at least he’s still.

“All right.” Cole, acting head of security, has the CCTV cameras recording on a loop, she knows. They’re never watched or observed except in cases like these, but it’s good to know they’re there. “Here’s where they begin.”

It’s not riveting viewing at first. In fact, Cole fast forwards through large sections where nothing much happens at all. Dean and Paul talk, they move around the room. Dean appears to be respectful enough, even smiles a little. Paul puts him in a dress and panties. He apparently tries to teach Dean to dance. Then has Dean kneel on a cushion for a long time. Then more talking. The camera catches one massive eye-roll from Dean when Paul turns away, but then Paul leaves and brings in lunch, and Meg sees herself come in for the check-in.

“He’s tense,” Castiel says into the quiet room, making everyone jump a little. “Dean. He’s not relaxed. See, how even when he has his head down, he tries to keep his eyes on Paul. And how his weight is on his feet even when he’s kneeling.”

“Yeah,” Cole says, leaning closer to the video.

“I can’t see a damn thing,” Gabriel complains through the video call. “And you’re all terrible narrators.”

“Nothing’s happening,” Meg explains. “It’s all very mild so far. He’s wearing a dress, they ate lunch. I checked in. Now they’re going to the bed. Hang on, let me adjust the video so you can see.”

Meg is fairly sure that she’s the only one who can hear Castiel’s subsonic growl. It almost turns her eyes black, and she shoots him a reproving look.

“A spanking,” Benny picks up the narration. “Nothing extreme. Looks like he’s trying to get Dean into subspace.”

Dean is over Paul’s knees, and he no longer looks bored, but the annoyance is more evident on his face in the video, as is his clenched jaw and narrowed eyes. He looks almost angry. But he’s not fighting or struggling. Paul isn’t going overboard or anything either, and appears to be checking in on him like he should. He has Dean’s dress up over his back, which is admittedly a pretty picture. The spanking goes on for a long time. Nearly half an hour. Dean answers when spoken to, but doesn’t appear to make any other sounds.

Then Paul gets fingers up into Dean, suddenly, and it’s clear he’s hitting the Angel gland, the way Dean goes heavy-eyed. Pau looks a little different, too. More intense. He plays with Dean like that for a while, then strips Dean naked without fanfare, and moves Dean to the floor, and Meg sees herself come in for the last check-in. Everything pauses and they both respond to her on-camera, and then the oral sex continues for a while, before Paul yanks Dean up off the floor and moves them both to the spanking bench. Dean’s perfectly alert, goes with apparent willingness, but Paul doesn’t look happy. Not unhappy either, but there’s something…

“I think this is where it gets interesting,” Benny points out, as Dean speaks and Paul’s face flashes into an expression that’s totally unfamiliar. Angry and hard. Then it smooths out, and he snaps the ankle and wrist cuffs Dean’s wearing to the bench, and takes off all his own clothes.

Castiel has been raging since he was told that something had gone wrong with Dean and Paul, Meg knows. It’s been evident in every word and movement he’s made. But now he’s like a lit fuse beside her on his chair, and she’s honestly a little concerned about the house if he should blow.

“He’s fine,” she murmurs to him. “We know how this ends.”

“He dared,” Castiel breathes, but then shakes himself. “Yes, thank you. Indeed.”

They watch as Paul uses the strap on Dean, then the flogger, then the strap again, and Dean obviously stays silent, though his body reacts. Paul speaks to him often, but they can’t see his full face. His body looks angry.

“Dean knows there’s a panic button on every one of those pieces of furniture! Why isn’t he hitting it!” Benny breaks in, frustrated, after a particularly hard strike with the strap, and Meg shoots him a sympathetic look.

“He shouldn’t have to use it,” Castiel growls. “Paul knows better. This is, this should never happen.”

“Nothing terrible HAS happened yet,” Meg points out. “He gets smacked harder than this for sassing. Calm, please,” she almost begs. Castiel’s wings are a dark shadow behind him, his eyes are nearly white, now.

The scene seems to go on forever. Paul puts aside the flogger for a time uses hot wax on Dean’s back, which as far as Meg knows, Dean hasn’t been introduced to yet, and should therefore be on the no-go list. He fingers him again, roughly, and uses a vibrator on his balls and caged cock. The camera can’t see Dean’s face, but there’s no relaxation or surrender in his body, though he isn’t struggling, either.

Finally, Paul, his hair dark with sweat, throws down the vibrator, and rummages in his bag. When he comes up with the large, single-bladed knife, Meg sucks in a breath. Castiel is still as stone beside her, and a glance shows both Cole and Benny frowning hard.

Paul shows it to Dean, shoving it under his downturned face, and Dean goes tense all over. Paul is grinning now, but it’s not a friendly expression. He walks back down Dean’s body, trailing the tip of the knife down his spine leaving a bright red line, and laughs at Dean’s full-body shudder, talking to him. Then--oh fuck--he slides it between Dean’s ass cheeks. It’s not a clear picture, but from Dean’s rigid motionlessness, Meg can imagine the point is right at his hole. And Paul’s still talking. He finally moves it again, and Dean’s body heaves for air, as the blade scrapes over a round buttcheek, and then Paul slaps him with the flat of the blade.

The next split second is a confusing flurry of motion. Dean is suddenly up off the bench, one hand cuffless and the other hand and one foot unfastened somehow, and he has Paul’s knife wrist in a tight grip, while his other hand punches at Paul’s throat even as he kicks Paul’s knee. They both go down in a tangle, the bench tipping with them, and Paul jerks his hand loose, shoves the point of the blade right at Dean’s eye--Dean slips the strike, bobbing away so the tip slides down his cheek, then burying his face down out of danger as he kicks loose of the bench and starts fighting for real. Precise, brutal hits that clearly mean business. He twists the knife away in a moment, it looks like he snaps Paul’s wrist in the process, punches Paul twice in the face, then drops a knee into his solar plexus and it’s over as Paul gags and heaves and curls into a curve on the floor.

Panting, bleeding, grinning, Dean wastes no time in tapping the handle of the flogger--flung to the floor in their scuffle--on Paul’s head, knocking him out. Then he takes his time finding rope, binding Paul hand and foot, and dragging him out the door.

Cole hits stop on the video, freezing the frame on the empty room. Everyone sits back, even Castiel, blinking a little.

“I think you should get Dean, now,” Castiel tells Benny, clearly forcing himself to be calm. “I would very much like to know what prompted the breakdown of the scene.”

“I want to know how he got out of the cuff,” Cole agrees.

“I want to know why he didn’t let me know something was wrong during my check-in,” Meg says, coolly. Castiel holds up a hand to them.

“Let him tell it in his own words, save the questions for later. For now, it’s clear he was able to save himself from a highly volatile and dangerous situation, for which I am very grateful.”

Meg stares at him, then at Gabriel’s somber face on the video feed, then sits back in her chair. She will hear Dean’s story, all right.

Dean struts into Castiel’s office behind Benny, a butterfly bandage white on his cheek, gauze wrapped around one ankle, but obviously very pleased with himself. He glances quickly around the room, waves at Gabe on the laptop screen.

“Benny said you’ve been watching my highlight reel,” he says brightly, before anyone else can speak.

“Dean,” Castiel rumbles, and is at his side in two strides, hands on his shoulders, pulling him into an embrace. Dean jumps, almost grimaces, and Meg can practically taste the adrenaline rolling off him still. “I’m very glad to see you well. We have some questions about what happened. Can you answer them for us now?”

“Sure,” Dean says, cocky, pulling away a little. Castiel cocks his head consideringly, and hums, and Meg breaths a silent sigh of relief when he takes hold of Dean’s collar firmly.

“Let’s get you settled a bit, first,” he glances around the room. “A moment, please. Dean, up on the bench, Wait.”

“Right here?” Dean whines, and Castiel growls at him, and Dean sucks in a breath and scrambles down to his knees quickly on the long padded bench, sliding into the wait position. Privately, Meg has to admit that he has totally mastered all the positions, and looks perfect even now, kneeling elegantly, hands palm-up on his thighs, back straight.

“Better,” Castiel praises, and runs a hand gently over his head, down to the back of his neck, and Dean shudders out a little sigh. “I know Benny has checked you over to be sure you’re all right, but I believe we will all feel better to confirm it with our own eyes.”

Meg watches, patient, as Castiel touches Dean everywhere. He lingers on the red marks on his wrists and around the ankle that isn’t bandaged, and the red welts on his ass, the shallow cut down his spine. He’s right, she does feel better, seeing that Dean is whole and unharmed like this, seeing that the strapping only left minor welts and bruises, and that he appears to have taken no lasting psychological harm. At least so far. But the way he is calming under Castiel’s hands is promising, and his flush and shiver as Castiel gives his breast and anal glands attention, massaging them firmly, even more so.

Watching them together is always a treat.

“There,” Castiel says finally, stepping back with one of his enigmatic little smiles. He seems much steadier, too. Dean looks very different now, his eyes clear and calm, shoulders down, hands no longer clenching into fists. The bossman cleans his hands at the wall sink, and Dean takes a deep breath and lets it out, and even Gabriel is smiling a little when he looks up from something he’s reading at his desk back at home.

“We ready to do this now?” His voice is tinny over the microphone, but clearly fond. “I think it would be a good idea to hear the whole thing from Dean’s perspective, in your words, Dean. No interruptions until the end. And Dean, we’re recording this, just to be clear.”

“I mean, you saw everything on the video,” Dean looks uncertainly at Benny and Meg, “but okay? Do you want me to start when we got to the room and were in private, or?”

“That’s fine,” Gabriel assures him. “Castiel was with you until then.”

“Right.” Dean rubs his hands down his thighs, then laughs. “So, I guess you don’t need me to tell you all the stuff that happened. Since you saw it. But it turns out, Paul knows all about Hunters and the supernatural because his sister got bit by a werewolf when he was a kid. And my dad killed her? Or at least was part of the team that got her. He wasn’t totally clear on that.” Dean grimaces a little, glancing at Castiel sideways. “It’s not exactly something that would have showed up on a background check or anything. Nobody knew.”

“Holy shit,” Meg breathes, leaning forward, elbows on her knees. Benny stands up violently, and Castiel is taking deep, measured breaths.

“This was revenge? It was planned?” Gabriel’s voice is clear and cold. Meg can sympathize. If he’d come into their home with premeditated plans to abuse Dean…

“Please, no interruptions,” Castiel reminds them all, through clenched teeth.

“I don’t know. I don’t think so?” Dean shrugs, unsure. “I mean. We didn’t exactly have a heart to heart about it, but he didn’t say anything like that. He was getting frustrated because I wasn’t going into subspace, I think. He kept talking about hunting, and I kept asking why he knew about it. Anyway. So, we got started, and it was fine. Boring, I guess. It was like when we did the cleaning stuff,” he looks at Meg. “There just wasn’t any kind of...I don’t know. It wasn’t interesting. But I was gonna try, like I promised. So I did what he told me to do, I didn’t argue or anything.”

At Castiel’s nod, he fidgets, settles, and continues.

“He kept using his Dom voice on me, and it was fine, but I only met the guy today. He kept saying he wanted me to relax, but I’m not a relaxed kind of person,” Dean scowls. Meg bites back a rueful smile. “So, we go through all this stuff, and he starts talking about how I gotta let all the reflexes from being a Hunter go, that it’s holding me back from being a good Submissive. That being all defensive like that wasn’t helping. And I said, how the hell would you know, since you’re obviously not one, and you wouldn’t last a day. Only I said it politely,” he hastily adds to Castiel.

Now Benny is also obviously trying not to smile.

“He started getting frustrated. He started, uh, spanking me, and telling me that Hunters were killers. That’s when I knew something wasn’t right. He sounded too angry. So I picked the lock on one of the wrist cuffs--”

“How?” Cole asks, and ignores Gabriel’s huff.

“Oh, I,” Dean pauses, glances around the room, suddenly hesitant. “I, uh, I have a few paperclips and things stashed in all the rooms. In the house. You know, in case. You never know when shapeshifters might invade!” he defends, in response to Castiel’s flat look.

“We’ll return to that. So you knew then that something was off, with Paul.”

“Yeah. He was fixated on me giving up on the whole idea of hunting, wanted to get me to say it was bad, wrong. And I guess he thought if I was in subspace it’d be easier? But the spanking just made me angry.” Dean shrugs.

“Dean,” Meg interjects. “I came in, to check on you both, well after that. Why didn’t you end the scene then? You could have just given the hand signal, and I would have called the whole thing off.”

“I had it under control,” Dean says, casually dismissive, and by god, that is IT. She bursts up to her feet, only to be checked by Castiel.

“Later. When he’s done. Continue, Dean, please.”

With a wary look at Meg, Dean keeps talking.

“I asked him about why he was so fixated on the Hunter thing. I said Sir hadn’t been having any trouble and I’ve been here over a month. Then he told me about his sister, and being ‘dealt with’ by someone named Winchester. It wasn’t like some vendetta thing. Just to illustrate why hunters are murderers to him, I think.” Dean makes a face like he’s tasted something sour. “Anyway, I maybe told him it wasn’t murder, once she had been bitten.”

“Oh, Dean,” Benny sighs.

“That’s when he put me on the spanking bench, and started to get real rough. I think he thought I would admit I was wrong if he hurt me enough. He kept telling me to apologize, to submit. I wasn’t gonna do that, but I admit I was a little surprised when he pulled out that huge-ass knife. I wasn’t expecting it to get that serious.” He shrugs, almost apologetic. “That really pissed me off. No need for that, you know? So I unfastened the cuff, unbuckled most of the others when he wasn’t paying attention. Almost got caught, there, so I only got three loose, but it was enough. I mean, once I felt like there was real danger, I took steps. And then I took him out of the room and yelled for help.” He stops. Clearly done, clearly satisfied that he has explained everything to full satisfaction.

Castiel sits back, obviously as astounded by this recitation as the rest of them.

“Now can I ask?” Meg patiently asks the room at large.

“Sure, go ahead,” Gabriel answers from the laptop.

“Let me start with this,” she says, meeting Dean’s eyes levelly, sitting up tall again. “I understand that your background lends itself to independent problem solving, to self-reliance, and to mistrust. I respect that. But if you were on a hunt with your family--hypothetically--and Sam were in a situation that he knew was going bad, and decided to not let you know in any way, to just ride it out himself, how would you feel?”

“That’s not the same at all!” Dean protests immediately, hotly.

“How?” she shoots back, just as sharply. “You are the beginner here. You’re still learning the ropes, still figuring things out. We’re more experienced. What’s more, we, all of us, are responsible for your safety and health and well-being here, and it’s easy for a Sub in training to get overwhelmed without even knowing it. That’s why we have the check-ins, Dean. And the panic button. And the cameras, though clearly we need to keep a better eye on those. But we rely on you, the subs, to be honest with us when you’re feeling unsafe. So we can help, and keep things like that physical altercation from ever happening.”

“Easy, Meg,” Castiel murmurs.

“I don’t think that would be appropriate at all,” she informs him. “What if he were cut? Really damaged, by this Dominant, in a rage? What if it truly did go badly? That would be on US, because we put him in that situation.”

Castiel blanches.

“It wouldn’t happen,” Dean pleads. “I can deal with it, no matter what.”

“That is stupid overconfidence,” she tells him, brutal and direct, and he narrows his eyes at her. “We are here to help you while you are learning. But you have to trust us to support you, and I don’t know how to get through to you, to let us.”

“Okay, okay,” Benny breaks in, making calming motions with his hands. “Your point is made. It’s something to talk about. For now, it’s obvious Paul broke every rule, regulation, trust, and faith with the Novak Training Company. And Dean isn’t at fault here. We’ll have you give another statement, cher, just the facts and events, without the supernatural stuff, for the legal team, okay? And he’ll be let go, of course. Do you want to file charges?”

“I think I broke his wrist,” Dean says, considering, once he’s torn his eyes from Meg. “And his nose. Nah, I think I’m good.”

“All right. So. Cole, we’ll escort him out. Yes? Drive him to the Austin facility, to process his paperwork. Get his full statement on the way. We should be back late tonight. ” At Cole’s nod, they leave the room. Gabriel signs out moments later, leaving Meg and Dean and Castiel alone in the room.

“I’d like to take over Dean’s alternate Dominant training, since Paul didn’t work out, Boss,” she offers, once they’re really alone. Castiel can’t look away from Dean for long. “Benny and I were discussing it, and we know it’s still important. But I know trust is hard for Dean, and I think here in the house we’ve all built a good foundation of that. I know Benny would also be happy to step in.”

“I think you’re right,” Castiel admits, though it almost sounds grudging. “I...perhaps tomorrow or the next day. Tonight I believe both Dean and I would benefit from time together, yes?”

“Yes, Sir,” Dean beams at him.

“Thank you. And I’m glad you’re okay, Dean,” she smiles at him, and he smiles back. He’s a handful, all right, but it’s certainly never boring with him around. And she’s already plotting and planning, how she and Benny might tag team the boy for best effectiveness, once he’s theirs for a few days.

Chapter Text

By the time Dean is done giving his statement (again) to the camera, with all the fun parts left out, and has wolfed down the sandwiches and soup Angelique brings to the study for them, he’s nearly wobbling on his feet. He knows it’s the adrenaline rush finally leaving; it’s been carrying him okay so far, and he’d really like to be done with this whole day sometime soon.

“All right. That’s finished,” Sir closes his laptop and stands up from behind his desk. Dean blinks at him from his spot on the couch. “And you look beyond done in. Let’s get you a bath, and then to bed, and start fresh tomorrow.”

“Mmm. Sounds good.” Dean’s shoulders and one hip are aching, now that he’s been still enough for long enough to notice, and he accepts Castiel’s hand up gratefully. He has to block an enormous yawn behind the back of his hand, and Sir slips an arm around his waist, leading him out of the room and up the stairs.

“No wonder you’re tired. That was quite a day. Here, sit. I’ll waterproof your cuts while the bath is filling.”

“I can do it,” Dean protests, half-heartedly, only to be stilled by Castiel’s hand on his shoulder, pressing him down to sit on the toilet seat.

“No, you sit. I very much need to look after you now.” He crouches by Dean’s side, looking up at him with a small smile and warm blue eyes that never fail to make Dean feel a little dizzy. “I must apologize again, Dean. We’ll talk about this more, tomorrow and over the next few days. But no one should ever have threatened you like that, hurt you like that. And it happened on my watch. I cannot tell you how much I regret that.”

“It’s not your fault--”

“It is,” Castiel interrupts him firmly. Dean looks away from his gaze. “I take responsibility for everything that happens in your training, yes? That means good and bad. And this was bad. He violated your trust. And we will do everything we need to to make that up to you, to repair that faith that we didn’t keep with you, to keep you safe.”

It’s all just. A lot. Dean stares down at his knees. He’s still feeling more than a little triumphant about his absolute victory over Paul. At the same time, he really was trying to be good. He’d promised Sir. And then Paul fucked it all up by going crazy on him. He’s not in trouble for beating on the guy, everyone has been super clear about that. Benny even gave him a high-five. But at the same time, that sour feeling, like something he ate is sitting wrong in his stomach, is still there.

“You’re not mad,” he says. It’s a question, but he can’t quite make it sound like one.

Sir sighs, and stands, and pulls Dean’s head close to his hip with a warm, firm arm. It feels amazing, comforting and secure and Dean sighs and lets himself relax a little.

“No. I’m not mad at anyone but myself, for failing to check Paul’s background more meticulously. We--Meg and Benny and myself--will work to earn more of your trust, so that you know you can call on us to help you. To prove to you that something like this, that never should have happened, will never happen again. So you know you have us, no matter what, even when you are with a stranger. We thought that was clear already, but obviously, it isn’t. And I’m disappointed that your first session with a stranger went so poorly, but that’s nothing at all to do with you, sweetheart.”

“Okay,” Dean says, feeling small. “You’re not going to get rid of all my picks?” Because now they all know about them. It’s an uneasy feeling.

Sir pulls back so he can look him in the eyes again. “No. Though I am surprised you managed to hide them from Claudia. And I hope you’ll tell us when you’re comfortable removing them yourself.”

“Mmm.” Dean looks down again. “Shapeshifters could get in.”

“Is it really them you’re so concerned about?” Sir stands up and turns off the water, then urges Dean to step into the tub. It’s just this side of too hot, and Dean hisses and dances a little as it stings the abrasions on his ankle, and then on his wrist and butt as he eases in. But the burning soon passes, and he relaxes back, watching Sir remove his clothes with interest.

“Yeah. I mean, I’ve been in some bad situations. It’s not...I don’t know. I need to have an exit strategy.” He looks at Castiel as the man steps naked into the tub. The long, powerful lines of his body, the dark curls of body hair, the intimidating heft of his cock, even soft, between his legs.

“All right,” Sir says calmly, thoughtfully. “Perhaps you’ll consider lettings us--myself, Meg, Benny, Ash, Cole, the rest--be your exit strategy, in time.”

It sounds crazy to Dean. Just today, someone had held a knife at his ass, in his face. But that feels strangely far away right now, as Sir tucks in behind him in the huge tub, starts giving him all that skin contact, pulls him in between his heavy thighs.

“Maybe,” he allows, though he’s dubious.

“Here, let’s wash this day off you.” Sir gently moves the soap over his shoulders, down his arms. It’s gentle and calm, everything today hasn’t been, and he’s careful with Dean’s wrists. He takes off Dean’s chastity cage, and that feels strange, the hot water against his cock with no barrier. Weirdly, he doesn’t get hard. Sir’s fingers stroke and soap and rinse every inch of him, and by the time he’s done, Dean feels like he’s wearing a new skin; kind of raw, but fresh, and clean.

“Better now?” Sir’s voice is a low rumble that moves through his chest into Dean’s back, and for no reason at all, Dean feels tears prickle his eyes.

He sniffs hard. Then again.

“Hey now.” Sir’s arms come around him, and turn him, and then he’s crying a little--not a lot!--with his face against Sir’s neck. It’s warm and dark and safe there. And it’s only a minute before he’s making his eyes wide and staring at the ceiling and getting the tears to stop.

“Sorry,” he gets out hoarsely, but Sir shushes him quickly.

“Want to tell me what that was about?” His blue eyes are calm. There’s no mockery there, he’s just watching Dean, and holding him close, one hand resting on his hip, the other on his belly.

“Just.” Dean flaps a hand in the air. “Leftover stuff, I think. I was angry, and then worried you’d be pissed off, and then it felt good to take him down, but bad because...I wasn’t good for him, was I?” He stares at the ceiling.

“Dean.” Sir sounds a little stern now, and nudges Dean’s chin until they’re looking at each other again. “You are very good. You are wonderful. Standing up for yourself, defending yourself in a dangerous situation? Keeping yourself safe? That is exactly what a good, strong, stable submissive does, that’s what you did, and I’m very proud of you. You were perfect. And none of this, anything bad that happened today, was your fault.”

Dean makes a small noise in his throat and maybe has to hide his face again for a little while. But that sick, queasy feeling in his stomach is gone.

Sir gets them out of the bath and dry with no wasted movements, and then right to bed, and Dean’s shivering a little in anticipation, thinking about what comes next. But Sir just hangs up his towel, goes around putting a few things away in the room. He catches Dean watching him, confused, and smiles.

“You’re all bruised, Dean. No paddles for you until your bottom is healed up, and I think with that sore arm and leg, anything too rough would be too much, tonight. Just sleep.”

“But you said I was good!” the protest bursts out before Dean realizes it, and catches Castiel in mid-stride. He turns, and comes to where Dean is sitting gingerly on the bed.

“Sweetheart.” He cups Dean’s face in his hand, strokes his hair. God, it feels so good. “I want you to stop and think for a minute. Do you really need this tonight? Or are you just unsettled from our routine being so confused today?”

Dean breathes hard, through his nose, and forces himself to think about it. The way the pain of Sir’s cock in him gives him something to fight against and surrender to so he can find that perfect, quiet, calm peace. The way knowing he’s bringing Castiel so much pleasure fills every part of him with bliss. Balanced against the deep ache in his shoulder, the way his ass throbs from the strap, how exhausted he is.

“I need it. Please,” he says, voice almost firm. It’s not begging, it isn’t. “I want to feel it.”

“You are a constant surprise,” Castiel smiles at him. “No, don’t get up. Put yourself in Present or Rest, whichever is most comfortable and the least strain. We will do this gently tonight.”

Dean chokes back a little sound of protest, but obeys quickly. He can’t see Sir behind him now, but something in him settles even as his stomach tightens in fear and anticipation. He’s curled on his front, in the Rest position. And he still jumps when the cool hard tip of the lube syringe enters him.

“So needy,” Sir teases, though there’s a bass growl in it now. “You have the most perfect bottom and the sweetest little hole. I’ve been thinking about fucking you all day, Dean. And I heard that little whine. I should tell you, there are so many ways to make this more torturous for you, without being rough at all.” He slowly withdraws the syringe. It almost tickles, and Dean squirms his hips, and gets a gentle slap on his hip.

“There’s a lotion that will keep your anus and rectum from ever stretching,” Sir growls in his ear. “So every time I push into you, it’s like the first time, tight as a vise.” The sticky-hot, hard head of his cock slides up Dean’s crack, and suddenly Dean’s heart is thundering hard in his chest, his mouth is wet, his hands are making fists in the blankets. “Or a cock sleeve I can wear, roughly textured for your displeasure. Or put the Humbler in you all day, and have you come to me at night already raw and sore.” The tip is right there at Dean’s hole, clenched tight.

“Oh god oh god,” Dean breathes out, barely a sound at all. “Please please-” and even he doesn’t know if he’s asking for those things or to never experience those things, because Sir pushes in then.

It’s much slower than normal, but Dean’s back still arches up, then hollows down, his body trying to make room for the huge hardness splitting him open. And it burns, it is like fire, the slowness just forces him to feel every inch.

“HNNNN,” he gasps out all his air, trying to make room. Sir is relentless, in and in and in, then a brutally quick slide out, then in again, and Dean wails into the bed. And again. And again. Dean feels rigid, stiff, he’s panting for breath, but then a wave of something hits and his hips give, spreading a little.

“There you go,” Sir growls, and starts to speed up his pace. He’s still so slow, though, and it’s hard for Dean to find that sweet, drifting place without the edge of rough struggle, the physical aggressiveness and roughness. He tosses his head, moaning, flinching when Sir reaches for his soft cock, tucked between his thighs and belly.

“You’re so good, Dean,” Sir murmurs in his ear, and shoves himself home right to the root, deep and hard, his whole body weighing Dean down and holding him still, and Dean can’t even scream. His cock is clamped in one of Sir’s hands and his hole is agony and then, slowly, everything falls away. No more worry about Paul, or the day’s events. No more thinking about what will happen tomorrow, or the next day. He’s only right here, right now. The sharp edges of the world fade and his body finally eases, finally feels right, the pain feels right and good, and Sir is making pleased, proud sounds, as he rolls his hips against Dean’s, over and over, changing the angle, rooting in deep.

He’s there, Sir got him there, but the pain is still sharp, and Dean still howls when Sir kneels up over him, fucking his cock straight down towards the bed, pistoning in fast and hard and then coming with a long, snarling groan that rattles Dean’s bones. He pulls out without any fuss, and then gently eases Dean to his side, cleaning them both quickly and tucking them into bed, watching Dean’s face closely as he blinks, suddenly overcome with exhaustion.

“Thank you sir,” he manages to blur out, even though everything is slow and sticky and sweet. Sir’s arms around him are heaven. The bed feels like clouds.

“You’re my good, good boy, Dean,” Sir praises, and smiles, and oh, warm tingles everywhere, that’s amazing. “You were wonderful, I’m very pleased with you. Now rest.”

“Mmmyessir,” It’s the last thing Dean remembers until morning.

Chapter Text

Dean squirms deliciously under Castiel’s hand as he smooths his palm over that upturned, still-bruised rump, already pinkened by his palm. Yesterday had been a calm day, of rest and recovery; as Castiel had thought, Dean had been sore and out of sorts and hadn’t wanted to leave his side, so Castiel had insisted on a massage, an easy swim in the pool instead of exercise, a (much-protested) rest period, and an early bedtime. Today he has been rewarded with Dean seemingly back to normal, though it will be another day before he’s able to paddle him properly, morning and evening.

“Spankings are nicer than paddlings, hmm?” he teases a little. Dean is over his lap on the big armchair. They’ve had breakfast already, and he’d pulled Dean to him in the big common room directly after to be sure his bottom didn’t feel too neglected.

“If you say so, sir,” Dean grumbles, but his voice is breathy, and Castiel can see how pink his cheek is where his face is turned to the side, and his visible eye is heavy-lidded.

“I do,” Castiel confirms gravely, and spanks him again, right and left, careful of the fading marks from two days ago, but firmly enough to see the clench and jiggle.

“Mmmm,” Dean sighs, and squirms again. His cock is a little interested, chubby where it’s held between Castiel’s thighs.

“Did you know that your bottom is one of the finest I’ve ever seen?” Castiel muses, as he strokes it again. “Round, and full, and so sweet. And it bounces.” SMACK.

“Sir!” Dean gasps, and he’s red now, whether it’s from embarrassment or the spanks, Castiel can’t be sure, but the curve of his neck is soft and relaxed and submissive.

The front door slams, in the distance. Castiel can hear a murmur of voices, but doesn’t bother to rise.

“Cassie?” Gabriel’s voice is cheerfully distinctive, and he strolls in, takes in Castiel and Dean and their positions, then throws himself into a chair opposite. “Well, you two make a pretty picture.”

“Thank you, Gabriel,” Castiel says, dry, and SMACK, brings his hand down again, preventing the aborted motion Dean was making to lift off his lap. “Dean, you weren’t told to move.”

“Hnng,” Dean gets out, strangled, then buries his face against Castiel’s leg.

“What brings you by unannounced?” Castiel’s happy to see him, but Gabe is generally too busy to make the two-hour drive on a whim.

“I was actually in the area for a meeting. And since I’m close, and as your elder brother and senior partner, I thought, I should drop by and see my bro. Gather up his little flock and find out how things are. Have a little tete a tete. A meeting of the minds.” Gabe is grinning at him, but his eyes are serious. “And you know I need your answer about coming to the city for a few days to help with the new hires, too. It’s meeting time, Castiel.”

“Hmm.” SMACK. “All right, Dean, sit up.” He gently helps Dean regain his bearings, flush-faced and blinking, and settles him half on his lap, curled under his arm.

“AND I wanted to talk to Dean, specifically,” Gabriel continues, and eyes Dean meaningfully before looking back to Castiel, and Castiel sighs. His nice, relaxed morning is disappearing before his very eyes.

“All right. We can meet you in the study in ten minutes? And you can speak to Dean then.”

“About what?” Dean is practically twitching with curiosity. That little spanking wasn’t nearly enough to get him into real subspace, though he’s pressed closely into Castiel, holding on tightly. “What’s the meeting about?”

“It’s nothing bad,” Gabriel assures him with a grin. “Okay, back in a few.” He bounces out as quickly as he’d come in.

“He’s so...perky,” Dean complains, after a long moment, and Castiel nods.

“I’ve always found it unbearable in the mornings, especially. But don’t let it fool you. Gabriel is both older and more intelligent than he would like you to believe, and he hides it behind this juvenile smokescreen to disarm people.” Castiel looks at Dean out of the corner of his eye, meaningfully “It’s very effective. But as he said, he is one of the senior partners in our business, and he’s called a meeting, and that is in fact, quite serious. So I need to make myself presentable. And you may wear one of your dresses, if it will make you more comfortable, or stay as you are.”

Dean chews his lower lip for a moment. “I think I’ll stay like this,” he says, a little hesitantly.

“That’s fine. Do you need the potty?” He asks it gently, but Dean still flushes a pretty pink color and looks at the floor.

“No thank you,” he mumbles, newly polite about it, at least, and Castiel leaves him there to change his shirt and wash his face. Take a few deep breaths, and try to settle his mind around what he suspects will be a challenging meeting. Surprise inspections are par for the course, and he knows intellectually that it’s perfectly appropriate for Gabriel to be here. Emotionally, though, every part of him wants to bundle Dean away and keep him away from prying eyes. He takes a few deep breaths and reminds himself that this is Gabriel, and that this will be fine, and goes and retrieves Dean.

When they get to the study, a few minutes later, Benny is lounging outside in an armchair, playing on a tablet. He glances up at them with a smile.

“Boss, lil’ man,” he nods at them.

“You’re in the meeting too?” Dean asks.

“Maybe later. For now, just standing by.” He tilts his head at the door. “Gabe is waiting in there. Had me bring a few things, Dean’s records and such, then told me to wait around a bit.”

Dean’s now visibly nervous, and Castiel puts a quieting hand on his hip.

“I’m in trouble,” Dean mutters direly, before they can even get to the door.

“Of course you aren’t.” Castiel soothes. “Gabriel is checking in, getting an update. It’s his job, sweetheart, he does it with all the submissives in training. Don’t worry.” And indeed, Gabe looks perfectly relaxed and normal, lounged in one of the most comfortable chairs, flipping through what looks like Castiel’s detailed progress reports on Dean’s Submission.

“There you are,” he enthuses, but doesn’t get up. “Get comfortable. I’m actually gonna talk to Dean-o, here, Cassie, you’re just moral support for now, so sit wherever, okay? We got a bunch to get through, here, so cop a squat and Dean, you can sit here by me.” He pats the seat of the chair beside him.

Dean makes big pleading eyes at Castiel, but he just shoos him over. Sitting gingerly, Dean watches Gabe warily, like he might explode at any time.

Finally looking up from the report, Gabriel blinks at him, then frowns.

“I’m not gonna bite you. I thought we got through all that last time I was here.”

Dean scowls a little. “Last time you were on the video, though, and I just beat up a Dom in the guest room and you were looking pretty pissed off you had to deal with all that, so forgive me for being a little worried.” He huffs and sits back, relaxing a bit now that that’s out, and Castiel has to duck his chin to hide his smile.

“Right, that whole thing.” Gabe sighs, and closes the report. “I’m here about that. Kind of. You didn’t do anything wrong, I’m getting that out there first thing. Okay? Hey, look at me. Okay?”

Dean meets his eyes with only a little reluctance, and nods agreement.

“Good. But that doesn’t mean there might not be fallout, so we’re going to be proactive here and make sure none of it falls on you, or the rest of us. And you’re going to have to work with me a little, kiddo. Think you can do that? Refrain from punching me in the face?”

That gets a snort-laugh out of Dean, finally, and his shoulders come down from around his ears.

“Yeah. Yes, I think so. Thank you.”

“Good.” Gabe looks satisfied. “Here’s the deal. We do outside check-ins on our Subs in training anyway, at certain points. It’s important to get new eyes on the situation, to make sure everything is going okay. You’ve been here just over a month, so you’re not quite due, but I’m moving it up a little, for a couple reasons. This is just one of ‘em. And I’d apologize for not warning you, but we always do these things cold. We want non-prepared reactions, and honest answers, you feel me?”

“I-” Castiel starts, and Gabe cuts his hand at him sharply.

“You are only here because he recently had a traumatic experience in unfamiliar hands, Castiel, and because I think he’s got some atypical reactions you might help with. In fact…” Gabe turns to Dean. “You want him to go?”

“No!” Dean exclaims, startled. “No, thank you, but no, please, he can stay.”

“Gotcha.” Gabe stands, and even though he’s a short man, Castiel’s always impressed by how much space he takes up in a room when he starts to pull his Dominant side forward. He drags one of the lushly padded benches around to the empty space, and holds out a hand to Dean.

“Up, Dean.” The Dominant command in his voice is so deep that even Castiel’s fingers twitch a little. Dean shudders all over, but then his eyes narrow, and his shoulders set like he’s bracing himself against a door.

“Why?” he demands, sharply.

Unexpectedly, Gabriel huffs a laugh.

“And there’s one question answered.” He strolls back to the report, and makes a mark somewhere. Castiel knows he must look desperately curious, nearly as much so as Dean, and Gabe has mercy. “Paul was questioned, extensively. One of the things that came out is that he’d tried to force you into subspace, and compliance, using his Dominant voice, and that it was ineffective. He had all kinds of idiotic ideas about why, but it’s obvious that you are simply very resistant.”

Dean looks smug, but then Gabriel turns to Castiel. “Cassie, please order your Submissive to the bench for inspection.”

Castiel is still reeling from the idea that Paul would commit such a violation as attempting to force subspace--force it!--on Dean, but he wrestles himself back from his rage, and nods.

“Dean. Up on the bench, sweetheart. Inspect.” He makes sure to put all the Dominance he can into his voice, feeling it thrum along his tongue.

Dean’s head dips, and he gets out of the chair, crawls up on the bench, and arranges himself prettily.

“He’s fully capable of ignoring or defying me,” Castiel warns Gabriel, who nods knowingly.

“But he doesn’t want to right now, he trusts you and has given you his Submission, and that’s the difference. Dean, if you’re ever looking for a job after all this, our Dominant reorientation schools are always happy to employ Submissives who can ignore an inappropriate command and make the Dom sorry they even tried.” He grins down at Dean, who smirks back.

“I might take you up on that--erp.” He sucks in a breath and goes tense as Gabe puts a gentle hand flat on his sternum.

“I’m going to touch you,” Gabriel tells him seriously. “A full inspection. I would anyway, and after the incident, I need to, and I think it’s important we get past our first impressions. I can bind you if you think it’s necessary, but I’d prefer not to.”

All the facade of goofy playboy is gone, and Dean seems to recognize it. He blinks a few times and takes a breath deep enough to move Gabe’s hand.

“Okay,” he says clearly.

Castiel can’t imagine what his face looks like right now, but Gabe’s smirk when he meets his eyes only gets more terribly annoying and knowing, and then he’s touching Dean’s face, his hair, his throat.

“Remember when you came here?” He starts, conversationally, and Castiel can tell Dean is startled, but he nods. “I’m sure Castiel, and probably others, had their hands all over you all the time. Touching like this, it’s the best way to start a bond of any kind between a pair. Hands on skin, it’s the oldest magic there is.” His palms run down to Dean’s collarbones, and Dean breathes out a shuddery sigh. “That’s very good. Yeah, if I’m going to be working closely with someone, Sub or Switch, we’ll do a long touch session. Like this, or a massage. It builds trust and closeness.”

Even Castiel finds himself relaxing, reminded again that Gabe, for all his fickle facade, is in fact, his elder, and sometimes wiser, and more powerful, and usually knows what he’s doing. He settles back in his seat, actually starting to enjoy the sight of Dean on his back, hands under his head, Gabe moving quietly around the bench as he strokes his arms, his hands, checks the abrasions on his wrists.

“These are nearly healed. How do your shoulders feel, Dean?”

“Much better, almost a hundred percent,” Dean answers calmly, immediately, and Castiel smiles a little to himself, matching Gabriel’s pleased expression.

“Good. Excellent. Though I shouldn’t be surprised with how fit and strong you are.” He reaches Dean’s breasts, and Dean tenses a little again. “Easy,” Gabe soothes him. “Let me feel.” His fingers circle one breast carefully while the other is flat on Dean’s shoulder, gently prodding, before he covers it with his palm and presses in. Dean sucks in air at that, arms going tense like his fists are clenching behind his head.

“You’re rigid here, my dear,” Gabe hums, moving to the other one and massaging more firmly, and Castiel winces a little, because he’d known about this. “Are they painful?”

“Sometimes,” Dean mutters. “I don’t like ‘em jiggly.” He’s staring at the ceiling with his lower lip between his teeth again, his cheeks flushed.

“Too bad for you,” Gabe tells him cheerfully. “They need much more stimulation. If your Dominant can’t tear himself away from your perfect posterior for long enough to give them attention, you’ll need to spend time on your belly, or do self-massage.” Castiel can feel his own cheeks heat. Dammit, Gabe!

He finally leaves Dean’s breasts, and checks his belly, his hips, his legs. Castiel knows that the scrapes on Dean’s ankle are nearly healed, but it’s good to see Gabe confirm it.

“Slide down the the end of the bench, Dean-O,” Gabe finally says, kind but firm, “and spread your knees wide.”

Dean glances at Castiel, who nods with what he hopes is an encouraging smile. Face set and determined, Dean scootches down the bench, until his hips are at the very end, knees bent up high and wide, heels barely touching the padding to either side.

“What a good boy,” Gabriel hums, “what a credit to Castiel,” harmonics rich in his voice, and Dean relaxes visibly, warming. Even smiles a little.

“You don’t keep him caged all the time, Castiel?” It’s nearly startling to be directly addressed, and Castiel has to clear his throat.

“No. He’s not aroused by pain, and after the spanking, I had planned to work on anal orgasms with him this morning. I often keep him uncaged to see his reactions as we train, as well.”
Gabriel nods, and takes Dean’s soft cock in hand. Dean’s hips jerk a little, but then settle. Gabe spends more time on it than Castiel usually does, fingering the head, the circumcision scar, weighing it and moving it. He pulls on it gently. Dean whimpers as it starts to fill in soft, helpless pulses of blood.

“There we go,” he says, satisfied as he watches it stiffen in his hand. “Good, healthy arousal reaction. Dean, tell me about the pain. Castiel says it doesn’t arouse you. Is that true? You don’t get hard when he hurts you?”

“It’s, ah, it’s true,” Dean answers, after a moment. Gabriel lays his cock gently on his belly, and starts feeling for his angel glands at the root, rubbing his thumbs in deeply, making Dean give a liquid little shiver. “I don’t, I don’t need a cage.”

“So you don’t like it?” Gabriel muses, as if absently. He presses Dean down with a hand low on his belly, and the other takes his balls in hand, rolling them.

“No! I mean. I don’t. I do?” Dean blinks down his body at Gabe. “My body doesn’t like it?” he tries, plaintively.

“That’s good. See if you can tell me a little more about how it feels,” Gabriel encourages him. Castiel has to bite his tongue, HARD, to keep from interrupting.

“It hurts?” Dean makes a motion that could be a shrug. “When I’m being punished it just hurts. Makes it better, after, so the bad feelings go away. I’ve paid for what I’ve done and now it’s over and I can feel good.”

“And when he’s dominating you? Using you for sex, hurting you here?” Gabe’s hand is moving, and from Dean’s little twitch Castiel’s best guess is that there’s a thumb at his hole.

“Different,” Dean says, thickly. He almost looks like he’s remembering it. “Um.”

“Tell me, honey. I need to know. Tell me how it goes, so I know how it’s different,” Gabe orders quietly.

“It’s a hard thing, because it hurts a lot,” Dean blurts quickly, “so it makes me proud I can do it. For Sir, so I can give it to him. And at first it’s just pain, and I can fight against it and lose, but it’s kind of winning too, and then on the other side everything is just perfect. It’s perfect, okay? Like nothing else ever.” He closes his eyes, his face bright red. “It’s like flying and being high and the best orgasm. My cock stays soft but what does it know anyway.”

“That’s so good, Dean,” Gabriel praises him, and Castiel himself is struck silent, even in his mind. He knew the pain of Submission was the only way Dean was reaching real Subspace, the battle and surrender were crucial for him, but he hadn’t understood quite how deep and meaningful even Dean had found the experience until this moment. He’s holding his breath, he realizes, and gets some air, and Gabriel meets his eyes, uncommonly serious.

“Has he reached subspace through any other means?” Gabriel asks.

Castiel tips his head, considering.

“Something close to it, what I’d call more of a penitent space, after a stern correction. A small space, during ageplay. A lighter subspace, after a difficult, painful enema. But real, deep subspace? No.”

“I’m going to need to see you put him down while I’m here,” Gabriel informs him, which he’d already guessed, since interacting with a Submissive in ‘space is part of every inspection. He rolls Dean’s testicles again, then pats his hip. “He’s very heavy and full, here. Are you milking him?”

Castiel has to glance at Dean at that, just to see his face, which is stricken and hopeful and murderous at once. He’s been begging since yesterday for an orgasm, which has been firmly denied.

“No, not yet, though if training keeps progressing, soon. I want him to start orgasming exclusively anally before I restrict orgasms entirely, and he’s come often enough to remain healthy so far.”

Gabriel nods, with a bit of approval. “Up and over, Dean. I’m going to look inside you, and then we’re done.”

Less gracefully than usual, but without protest, Dean rolls over and immediately hides his face in the bench. Castiel wants to go to him, hold him, pet his hair, anything, but knows that Gabriel needs to finish, first.

“Is he clean?”

“Nightly enemas. He’s dependent.” Castiel nods. “Present, Dean.” Dean moves up into his favorite position, and as always, he seems to settle as soon as his cheek is resting on his folded hands, his ass presented up in the air, thighs spread wide. His erection is gone, and it’s the prettiest sight. The way the low arch of his back emphasizes his tiny, lean waist, the long stretch of his back, and the perfect high round of his ass cheeks. Even the muscled thickness of his thighs, spread temptingly like this, all bare and golden, is perfection.

“Your positions are perfect,” Gabriel praises as he lubes his fingers, and Dean wiggles a little with pleasure. “Only one small mark left on your ass, I see, and some fading bruising, a small line on your back. You’re a fast healer, Dean-O. I’m happy to see it. Now be still. I’m going to spread you open a bit, look for good health, soft healthy glands, any sign of damage.”

He suits action to words, his fingers firm but not rough, and he prods them into Dean’s tight hole without ceremony. Dean gasps and tenses but doesn’t jerk away, even as Gabriel pulls two fingers slowly apart, stretching him open side to side, making him whine high in his throat.

“He’s lovely,” Gabe murmurs to Castiel, and Castiel knows he probably sounds like a besotted fool, but he can’t help answering “I know.”

Gabe’s fingers rub around inside Dean, rocking him gently on his knees, and then pull out, leaving his rim shiny with slick. Dean heaves a deep breath, and Gabriel strokes his bottom gently.

“You are looking wonderful, Dean. The turnaround you’ve made in a little over a month is nothing short of amazing.” Gabe moves around and sits near Dean’s shoulder, so he can see Dean’s face. “I know we got off to something of a rough start. But I could not be more proud of how different things are for you now, how healthy you are, how well you behaved just now, and how much it means to us that we were able to help.” His smile at Dean is one of his rare, genuine, beaming ones, and Castiel can tell Dean is giving him a broad smile in return.

“Castiel, come here a moment, touch your boy.”

Castiel only keeps from bolting to them with the firmest of self-discipline. He slides onto the bench, and then his hands are everywhere. He cups Dean’s soft cock, both of his breasts, the back of his neck, and feels small tensions relax in his boy as he does. He ignores the murmur of Gabe’s voice speaking to Benny to lift Dean out of his position and tug him into his lap. Dean comes willingly, a heavy solid weight across his thighs.

“You were so good, Dean,” he praises, and the sweet shiver through Dean is like the best drugs to his Dominant side. “I am so pleased and proud of you. I know that must have been hard, and you were absolutely perfect.”

“Wasn’t so hard,” Dean mutters, but he sounds pleased, and rubs his cheek against Castiel’s chest. “Are you really gonna...I mean. With him here?” He sounds scandalized, a little scared, nervous, eager, all at once.

“I am,” Castiel confirms. “This is part of my work. And I believe I’ve mentioned before, that sometimes orientation overrides relation?” he waits for Dean’s tentative nod. “Very much like that. Gabriel and I are both Dominants, and we have worked together with Submissives before. For us, this aspect isn’t familial, but solely to do with our presentation.”

“Oh.” Dean appears to be digesting that, so Castiel just holds him a little more closely.

Gabriel sits back down in the chair facing them, elbows on his knees.

“We have a few minutes before Benny comes back, before I have Castiel take you down, Dean. And I have a few more things to go over. First though, are you feeling good? Clear-headed, right here with us?”

“Yeah. Definitely,” Dean nods, and turns a little, so he’s sitting up straight, facing Gabe.

“Okay. I’m gonna talk for a minute, and I want you both to listen. You too, Cassie. I’m pulling rank right now, both as your superior, and as your elder.” He meets Castiel’s eyes sternly, and Castiel blinks, startled. He heard the subtext, could almost see a gold flash of wing. He can’t remember the last time this happened, really, but he nods, a little warily.

“The two of you have clearly formed a strong bond. No, Castiel, don’t ruffle up at me,” he holds his hand, and Castiel closes his mouth again, “I’m not accusing you of anything inappropriate. But we have conducted more than a few of these together, and you have never behaved in one as you have today. You were on the edge of your seat, your intensity was almost palpable, as was your possessiveness. And Dean, you are keyed to Castiel nearly exclusively. You looked to him throughout your inspection, even with an older and stronger Dominant working with you.” He sits back a little, looking determined.

“From what I’ve seen and heard, you’re also reasonably compatible, in terms of dynamic, sexual and orientation needs, and, if I can dare to say it, romantically.”

“Hnnng,” Dean makes an embarrassed noise, and shoves his hands against his face.

“Dean! Are you all right?” Castiel leans around to try to see.

“He’s fine, Cassie,” Gabriel laughs. “I’ve just called him out in front of his crush. While he’s sitting on your lap. But Dean, it goes both ways.” He gets abruptly serious again. “Since you are trainer and Submissive, this is obviously something that would present a few challenges. You could find another trainer for Dean---ah!” he cuts off the immediate protests. “You could finish Dean’s training, and then find another Dominant for him for a few months, until enough time had passed to offer him a collar and contract. Either way, though, I think it’s important that he understands exactly what you will expect from him, need from him, sexually, Castiel.”

Castiel takes a deep breath.

“We’ve spoken of it. A little.” He tells Gabriel. “We have other kinks in common, as well. But Dean is not a masochist, so I have been introducing him to pain in small steps, being sure to not crush him.”

“I’m stronger than you think,” Dean declares, stubborn with it.

“Either way,” Gabe shakes his head. “Before you make any decisions, you need to find out of this is something you can be to each other. If the serving and being served,” he holds up his hands flat and tips them back and forth, then holds them even, “fulfills you both. It’s the most important thing, no matter how pretty you think each others’ eyes are.”

“Gabriel,” Castiel growls, sincerely irritated by the intimation that he’d have his head turned that far.

“I’m serious, Castiel. You are the closest thing to a pure sadist I have met, and you’re not to make yourself miserable by shortchanging or downplaying that need.” Gabe’s voice has a hint of thunder behind it, and Dean leans back against Castiel’s shoulder.

“Whoa,” he breathes, even as Castiel dips his head with a chastened “Yes, Gabriel.”

“All right,” Gabe says, abruptly cheerful again, as mercurial as the weather, clapping his hands. “I’ll expect regular status reports if you decide to try it out. You get set up for phase two, and I’ll see what’s keeping Benny.”

They sit motionless for a long moment after Gabriel bounces out of his chair and to the door. Dean is rigid on his lap, and Castiel almost dreads looking at his face. This is not at all how he’d intended to declare his interest to Dean, if at all. But he is not a coward, and so he eventually sighs and turns him, using a little extra muscle when needed.

“Can we talk about it later? Or never?” Dean blurts, not meeting his eyes.

“Never is not really an option, but later, yes,” Castiel allows. “After all this is over. For now, don’t worry about it. It’s something we can let happen, let develop, and work through over time, and for now, it’s not important.” He tips Dean’s chin up with a finger, and forces their eyes to meet. Dean looks embarrassed, a little sullen, hopeful, worried, all tangled up with desire, far from the calm surrender Castiel knows he will need to find soon.

“Fetch your paddle, Dean,” he says seriously, calmly, and Dean sucks in a hard breath, eyebrows coming together. “Be a good boy for me,” he warns, before Dean can protest. “I will not hesitate to use the switch if I must. This will help you, settle you, and make the sex much easier for you.”

“Sir,” Dean says, like the start of an argument, and Castiel shakes his head, shifts Dean off his lap and to his feet.

“Run, upstairs, get it and back down and I want you back here on your knees in less than a minute. Go. Now.” He growls the last word, hard and commanding, and Dean bolts, passing Benny and Gabe as he does.

“Was it something I said?” Gabriel jokes, as he comes back in. “Cassie, Benny’s going to observe today, and assist if I want to pause or reposition, like he did with Juliette that time? Between not wanting you to snap my hand off if you get possessive of him, and Ben wanting to start training subs too, I figured it would work out.”

“Good idea,” Castiel nods, and Benny grins and hefts the large square block in his arms.

“Breast board for Dean. If you want it.”

“I think I’ll hold off this time, thanks. He hasn’t used the bathroom in hours, so we’re going to do desperation wetting instead, which will make him feel good, instead of introducing something new when he’s already off balance. But leave it here, we’ll get him onto it regularly,” Castiel thanks him.

“It’s going to make him yowl like a cat,” Benny predicts cheerfully, and Castiel has to agree.

Dean hurries back into the room, paddle in hand, and then stops, seeing all three of them standing in the middle of the room. Once again, Castiel is struck by how beautiful he is; caught mid-stride, perfectly balanced, all smooth lines, sleek muscle, and grace, the dusting of freckles over his cheeks and nose and shoulders just accents on the pale gold of his skin, the wide green of his eyes.

Castiel snaps his fingers and points to his feet, and Dean grimaces a little, but comes to him, dropping to his knees there.

“Good boy,” Castiel soothes, and strokes his hair. “This isn’t punishment, Dean. You’ve been very good today. Keep being my good, submissive boy.” He turns to Benny. “Can you put the padded breeding bench into the middle of the room, and the absorbent mat under it, please?”

“Sure, boss.” Benny moves to do it, and Dean looks up at him with huge eyes.

“Up and bend over the chair, sweetheart,” Castiel says gently, and lifts him to his feet, guiding him to the armchair. “I’m going to avoid his bruising, but he’s rattled from our conversation, and he needs to be calm before we start,” he tells Gabriel, who nods.

“I don’t need to be calmed down,” Dean twists to tell him, and Castiel puts a hand on his neck and bends him in half over the arm of the chair.

“Ten, Dean,” he says firmly. And follows it quickly with the first slap. Dean squeaks and goes to his toes, then back down. Castiel is sure to keep it exactly like their normal morning and evening paddlings, knowing how the ritual and routine soothes Dean; a slap, a pause, a slap, a pause. Even, steady rhythm. By six, Dean is quiet and still, breathing deeply, his face turned to the side, his jaw unclenched, and by the time the tenth blow falls, his fists have uncurled, and his bottom is pink and his thighs loose and easy.

“Beautiful,” Castiel hums, and sets the paddle aside, stepping up close behind Dean, running his hands over that lovely ass, feeling the warmed skin under his palms, then gently bringing Dean back up to his feet. The boy’s eyes are bright, but no tears. He hadn’t struck him hard, careful of the healing bruises. Dean gives him a small, quiet smile.

“I’m going to take you now,” Castiel tells him, holding his hand, pressing it to the front of his pants, where his cock is rigid and urgent. Dean’s eyes go big again, and he sucks in a quick, nervous breath. “I’m going to be very rough with you, Dean.” The shiver and flinch, the way Dean’s mouth falls a little open, it makes something hot, urgent start to coil in his belly, the back of his neck feel tense.

“Sir,” Dean pleads, a little begging word, and his eyes flick to where Benny is just finishing the breeding bench, Gabriel leaning on the desk and observing.

“You are going to come apart just like when we are alone,” Castiel promises him. “Perhaps even more, with how you love being watched. Sweetheart, it will be so good.”

“Sir, I gotta, I need the bathroom,” Dean says suddenly and urgently, like he’s only just realized, and Castiel frowns a little. Dean knows how to ask. And Castiel knows that it is good for Dean, for his submission, to ask properly. He cocks his head, stern.

Dean flushes a slow, hot, bright red. “I...can I, please, go potty?” he mumbles, head down.

“No,” and that red face comes back up in shock. “You’ll wet, from pain, or fear, or just the pressure, while I’m fucking you.”

“Sir,” Dean gasps, and staggers a little, like his knees just went weak.

“Go get your lube, and up on the bench. Now, baby,” Castiel directs, stern, and Dean goes, dazed. The lube syringe is on the desk, and it rattles as Dean’s shaking hand picks it up, as Castiel strips quickly, the relief of his rampant cock being freed delightful. Dean climbs onto the breeding bench, the straight middle supporting his torso, the knee braces spreading him wide and open and leaving his cock and balls hanging free while he grasps the crossbars in tight hands.

“Benny,” Gabe murmurs, and Benny nods, with a glance at Castiel, who also nods, as he takes the lube. Benny steps behind Dean and puts a gentle hand on his back, rides out his jump, and then feels around his tailbone, down his crack, around his hole and perineum. His fingers press gently at the taut skin there and Dean moans quietly, trying to hide his face in the bench.

“Hot and swollen,” Benny tells Gabriel quietly, stepping back. “He’s frightened, but fully receptive, despite being flaccid. Hole is rigid, tense, but the surrounding areas have responded to Castiel with hugely increased blood flow.”

“Very good,” Gabriel says, pleased. “Excellent. And how would you list that, if you were an observing Dominant trainer, giving a report?”

“Uh, Dean is showing evidence of Submissive arousal--”

“Nonsexual Submissive arousal,” Gabriel interjects. Castiel listens with one ear, idly delighted at the mentorship happening, as he approaches Dean, takes the lube in hand, cups his hand over one asscheek, feeling the deep tremble there.

“Brace yourself,” he coos, and shoves the lube roughly home, revelling in the way Dean gulps back a squeal, the way his hips clench uselessly tight, and empties the plunger as it withdraws. His own headspace, ruthlessly suppressed so far, starts to surge through him. He can feel his skin prickle and tighten, his shoulders bunch, his cock jerk and drip precome, even at this small taste of what’s to come. His vision narrows to the sweet, prone body spread before him, waiting for his attentions, his cock, waiting for what it needs and craves even as it gives him what he himself must have.

There’s no lubricant left for his cock, but Dean is well-slicked inside, and he spreads the boy’s cheeks with rough hands, pushing forward until the dry, hot, needy head shoves rudely against that tight, tempting hole.

“No no no no no no…” Dean is muttering, twisting, the first surge of real fear and resistance, always, trying to climb up the bench, away from the rough intrusion, and Castiel yanks him back into place by his hips.

“Be still,” he snarls, heat bursting through his pelvis, his belly, his mind, and surges forward, and Dean screams.

*

Benny is seriously grateful to Castiel and Gabriel for tapping him in on this inspection. He’s been hoping to move up to trainer, like Castiel does, for a while now. Seeing how much of a difference it makes to people like Dean, and getting to work with so many different subs, well, it seems like a no-brainer. And there’s no better people to learn from. Castiel, he’s like learning from an encyclopedia sometimes, though, tends to go into all the technical details. Gabriel’s running through it from a practical perspective as they watch the boss prep Dean, which is a great second perspective to get.

Anyone with eyes can see how far Dean’s come in the almost six weeks he’s been here, too, but watching Gabriel mark it down on his list has been damn satisfying, too.

“Non-sexual submission means what?” Gabriel asks him leadingly, eyes on the pair as Castiel lines himself up behind his Submissive.

“Mmmm, means he won’t get turned on or come from the act?” Benny knows this, he’s a little distracted right now.

“Partially. Mostly it means that he’s showing all the secondary signs of arousal, because orgasm and sexual pleasure aren’t this Submissive’s first or even a high priority for them in this situation or with this Dominant. He’ll get enhanced sensation, greater gland stimulation, faster recovery time, but no sexual response, because this is about Castiel’s sex, not Dean’s.” Gabriel looks happy about it, Benny thinks.

“I’ve heard them, can’t help it, Dean is a screamer,” Benny admits, “but this is the first time I’ve seen them together.”

Just then, Castiel shoves forward with his hips, and just his hips, holding the rest of his body away. He goes in to the root in one brutally fast thrust, and Dean shrieks, his whole body arching away as far as the bench will let him, arms scrambling for purchase on the wood, all his muscles suddenly in hard, glistening relief.

“Fuck, gorgeous,” Gabriel breathes, and Benny isn’t much of a sadist, but Dean’s pain is so exquisite he can’t help but agree.

Castiel looks gone, too, eyes dark and dangerous, hands digging in at Dean’s hips, and once he’s in, he drags back out with no ceremony, and then starts fucking hard and fast. Dean’s reflexive kick comes nowhere near him, and when Dean arches up, keening through clenched teeth, he shoves him back down with a quick, hard hand at the back of his neck.

“He’s nowhere near subspace yet,” Benny notes.

“He has to fight first,” Gabriel points out. “Go check him, please. If I touch him or Castiel right now, Cassie might try to kill me.”

Nodding, Benny approaches deferentially, making sure Castiel can see him, head lowered. He reaches a slow hand towards Dean, and doesn’t touch until Castiel murmurs “Go ahead.” and goes still, seated to the root inside Dean. Benny crouches to see Dean’s face.

“Ah, ah, ah, ah, ah,” every breath is a little sobbing cry, some loud, some soft, and Castiel lowers his hips and twists and Dean screams “HMMMMMM” with his mouth closed, eyes open but unseeing, his face wet with tears. There’s no release and relaxation of subspace, not yet. When Benny moves down, Dean’s cock and balls are tiny, pulled against his body, but when he touches around the root, even there is warm, full, soft, the glands fully stimulated. His hole is an angry red, strained hard and thin around the thick root of Castiel’s cock. Benny thumbs his perineum, and can feel his prostate and angel gland, shoved against the skin by how full he is, abused by the intrusion.

“Thank you,” he says respectfully to Castiel, bowing his head a little and stepping backwards, back to Gabriel.

A little more clear-eyed, Castiel nods back, drags his cock out with cruel slowness, and then thrusts back in.

“NO!” Dean wails, breaking somehow, shaking all over as he loses his grip on the handholds, his arms reaching back, trying to catch at Castiel, “I can’t, sir, too much, it hurts, please, Sir, please please, sirrrrr,”

“Let go, Dean,” Castiel grits out, voice rumbling with Dominance. He reaches down around Dean, leaning forward, grabbing his cock, pulling at it without much force. “Let yourself feel it, sweetheart, let yourself be a good boy.”

“I can’t, I can’t,” Dean sobs, but then he kicks again, and he’s wetting, as Castiel drives into him again, a powerful stream that draws his whole body forward with it, the release and relief and ecstacy so obvious on his face that Benny’s breath catches. He pees for a long time, a steady stream and then spurts coming with the thrusts of Castiel’s cock, and he’s moaning in time, and it’s one of the most erotic things Benny has ever seen. He’s hard enough to cut steel inside his scrubs, and he couldn’t look away from them to witness a murder.

“Good, so good, what a good, perfect boy,” Castiel is nearly singing to Dean, now, and Dean is finally easing, pain still written all over him, his mouth open and painting, little cries and whines and sobs driven from him, but softness passes through his body like a wave. His hips tilt back and up, his shoulders go liquid and his waist dips invitingly. Castiel keeps murmuring praise and pleasure to Dean, voice almost a purr.

“Jesus Christ,” Benny blasphemes, as Dean’s soft cock finally stops dripping.

“How would you document it, Benny,” Gabriel insists, though when Benny looks his face is a little flushed too.

“Erotic desperation? No...bladder release as substitute for sexual pleasure during intercourse,” Benny decides.

“I think that’s good, with some urolagnia thrown in, with both of them, and shame for Dean. I’d note that control of body functions for high-level Doms and Subs adds another dimension as well.”

“Yeah, that’s right,” Benny nods. Dean is boneless, now, rocking with Castiel’s movements, little cries of pain breaking from him when Castiel digs his cock deep or shifts his angle, but open and easy in his body.

“Check him again, please,” Gabriel asks, and Benny repeats the procedure. Dean is deep in subspace, eyes almost all dark pupil behind heavy lids, tears still rolling from their corners. His mouth is half-open, loose, cheeks flushed, head resting down like it’s too heavy to lift. He doesn’t touch, this time, but Dean is flushed dark between his legs, swollen and ripe aside from his small, limp cock, and his hole is an agonized red.

“He’s down hard,” Benny reports. “That’s fucking gorgeous. I’ve never seen him tip over the ledge like that before.”

Gabriel nods understandingly. Castiel growls suddenly, his body a hard arch over Dean’s prone and lax one, and he bites down hard on Dean’s neck, hips hammering suddenly, breaking his harsh, steady rhythm as he chases his orgasm. Dean doesn’t struggle, but his moan goes high, thready, desperately pained, and then Castiel’s hips are digging in and clenching tight once, twice, again, again, and he slowly comes to rest.

“Good,” he says, as soon as he lifts up. “So good. You were perfect, Dean. I’m so pleased, so proud of you.” His voice is like buttery velvet, rich and soft, and he pulls out of Dean slowly.

“No no don’t leave me sir,” Dean sobs, slurring, twisting, almost mindless, and Castiel gentles him down with long strokes of his hands.

“I’m going to bring him to the couch now,” he tells Benny and Gabe without ever looking away. “Benny, warm water and a soft cloth? And a bottle of cool water, please.”

Benny hurries to bring them to where Castiel is more or less carrying Dean to the couch, settling him on his lap, and pulling a throw around his shoulders. He takes them with a smile of thanks. All that fierce possessive Dominance seems to be tamped down again for now, and he’s just the same Boss Benny works with every day.

“Can you check his hole for me? I’m going to give him some water, let him be down for a while.”

“Happy to,” Benny smiles back. He has to gently lift one of Dean’s legs, but gets no protest. Lube and come are trickling from Dean, but that’s fine; he wipes the wet cloth gently there and Dean arches, gasping “ah! Ah!”

“Calm, Dean, easy,” Castiel soothes him. “Just quickly, sweetheart.”

“Be still, cher,” Benny agrees, and gently presses a finger into the raw, swollen puff of Dean’s anus.

“Ow,” Dean sobs, and Castiel gently hushes him.

“A tiny bit of blood, boss,” Benny reports, standing. “Just an abrasion, not a tear. He should be healed by tonight or tomorrow at the latest.”

“I’d tell you to be gentle with his enema tonight, but I know you always are anyway,” Castiel’s eyes crinkle with his smile. “Thank you, Benny, for everything.”

“Always a pleasure, and this was a privilege. He was beautiful.”

“He always is,” Castiel says, and it’s almost doting.

Gabriel sits cross-legged on the couch next to Castiel and watches the pair.

“So, Benny, what would your conclusion note say?” He finally asks.

Benny shrugs. “I can’t really give an honest one, since I know Dean so well. But I didn’t know how hard he fought before letting go. Every time?” He looks to Castiel.

Castiel nods. “Nearly. Sometimes more, sometimes less. His brother said something interesting when he was here...said Dean’s been fighting his whole life, and it’s part of who he is, now. I don’t know if it’s that, if it’s nature, or nurture, or a combination. But I think he’ll always need to kick and shout and hurt before letting himself surrender.” He smiles fondly down at Dean.

“Sounds exhausting,” Benny mutters, and gets a head-tilt of agreement from Gabriel.

“Mmmmm, tired,” Dean murmurs against Castiel’s chest, and Benny grins.

“This is why we do this before bed, now,” Castiel tells them. “He goes deep, and stays there.”

“Will he be all right without this, while you’re away?” Benny asks. “I know we’ve talked about it, but I don’t think I can get him there like that. Meg might be, but you’re the one he is really bonded to.”

“I think he’s going to test you hard enough the first day or so that you’re going to have to punish him,” Castiel says, plain and blunt. “Dean tests, and tests, and then tests some more, because until he knows what the boundaries are, he doesn’t feel safe and secure. You establishing those boundaries should be plenty for him, even without this level of subspace. I won’t be gone that long.”

“What’s this?” Gabriel is clearly itching with curiosity. “I know you’re coming out to help with the new Dom center, but why would he test Benny?”

“I’m going to be diaper training Dean while Castiel is away,” Benny says, with a sigh of both anticipation and a little dread. “With Meg’s assistance. And Dean is resistant. Right now he’s enema dependent and bladder shy, so there are a whole raft of challenges, too.”

Castiel smiles evilly at him. “Dean got hard as a rock the one time he used a diaper, so this will be good for him. I love having a trained submissive, but this is one part of training I’m happy to hand off to a subordinate. Especially one who has it as a primary kink.”

“It will be amazing,” Benny admits, “once he starts behaving. The first day is going to be hell, I expect. And I don’t enjoy punishing Submissives. I’ll do it when I need to, and do it so hard I don’t need to repeat myself.” He really, really hopes Dean won’t be the exception. He has the sinking feeling that that hope is futile.

“Well, isn’t that going to be interesting for Dean,” Gabriel muses, looking at him. Still completely checked out, Dean nestles closer to Castiel, who rocks him a little, stroking his hip.

 

“I fully expect to come home to a boy who can’t sit down on an unpadded surface,” Castiel agrees cheerfully.

Gabriel snorts a little, then straightens up.

“Okay. I’m going to write up a full report and send it, as you know. But off the top, you already know he’s about a zero as a masochist, but his nonsexual submission to your sadism is off the charts. He reached a full and healthy subspace and is maintaining it without issue, while normal conversation is proceeding around him. He was able to be touched and inspected by an unfamiliar Dominant. His medical numbers are still a little on the high side, but within healthy range. In conversation, he’s able to discuss his Submission clearly, calmly, and with acceptance. Overall, you have a healthy, active young Submissive on your lap. Congratulations, Castiel.”

Benny feels his face split into a huge grin. Castiel’s expression is a little more mixed.

“I suppose that means you did me something of a favor, though I had planned to speak to Dean about our future plans once I returned,” he says, with some asperity.

Gabriel nods. “He’s no longer a Submissive in distress. Under normal circumstances, he could be moved to one of our normal Submissive training schools, or even start looking for a regular contract or someone to take his Responsibility papers. Now you have this trip to plan how to tell him about...family history. And hide his stilettos.”

Benny laughs. “We’ve hidden them five times. He always finds them.”

Gabriel stares at him. “Take them out of the house, man!”

“Nah, that would be cheating,” Benny tells him comfortably.

“I will never understand the madness of this residence,” Gabriel informs them, and pops a piece of candy into his mouth.

“We could not put Dean into the dating market anyway,” Castiel interjects abruptly. Benny notes with interest how his arms have tightened more closely around the boy, and the distinctly possessive rumble in his voice. “Imagine what he would do to someone approaching him with disrespect. Though I don’t think that’s anything to do with his former distress, or his Submission. I think that might just be Dean.”

“Right,” Gabriel says, a bit faintly. “Benny, maybe we should let the two of them have their afterglow. I’ll show you how to write up a formal report in Castiel’s office. Cassie, we’ll see you two at lunch?”

“Definitely,” Castiel agrees. “I think we’ve both worked up an appetite.”

Benny glances back at the door, and sees Castiel curved protectively around Dean, pressing soft kisses to his hair.

Chapter Text

Dean, far from his usual sleepy, relaxed ease after his enemas, looks incensed when Benny ushers him through the door, and Castiel has a flash of fondness that he doesn’t bother to suppress. This boy, he thinks, will never stop being a challenge and a surprise, things he relishes and enjoys right down to his bones, and he almost can’t wait to hear what has caused this particular contremps.

“Sir! He wouldn’t let me talk to Sam!” Dean explodes, almost before they’re in the room, and Castiel, laying in bed with his ankles crossed and reading, raises a brow at Benny, who is obviously torn between hilarity and temper in a way he rarely shows.

“Dean, brother, you know that’s not how it was,” he tries, and Dean waves his hands in the air, stomping forward.

“Sam called, and we were just getting started, and Benny had Claudia say I’d call back tomorrow. That’s not okay, dude!”

“Dean!” Benny exclaims, and Castiel closes his book.

“Dean, quiet. Get your paddle, and be on your pillow, you may speak in a moment. Benny, sit down. Tell me,” he invites.

“That’s not fair!” Dean protests, and Castiel LOOKS at him, and he quails. Not a lot. But enough that he deflates just a little, and keeps stomping long enough to get to where the paddle is kept, grab it, and gracelessly fling himself down on the kneeling pillow. Castiel joins him there, sitting on the chair, pulling him between his knees firmly.

Benny takes a deep breath. “Sam called just as I was finally getting the flow started with Dean,” he explains, his deep voice calm. He clearly isn’t apologizing, and he settles in, relaxed, across from Castiel. “He’s still real sore from earlier, so it took a while to get the nozzle in and get him settled. Claudia asked if it was an emergency, or urgent, and she said Sam said it wasn’t.” He shrugs one shoulder. “It wouldn’t be good for Dean to stop and empty, then start again later. So I had her tell Sam that Dean wasn’t available just now, but that he’d call back in the morning.”

Dean makes a little growling noise from between Castiel’s knees, but it’s definitely a sign of progress that he doesn’t jump in and argue.

“Okay. And Dean?” The boy lifts his chin.

“I haven’t talked to him in almost a week, and Benny shouldn’t have kept me from at least checking in with him,” he says, stubbornly.

“All right.” Castiel rubs gently at the back of Dean’s neck. “It’s been a challenging day. And I know you’re very sore in your bottom, and the enema was probably hurting you in a way you’re not used to. Do you think maybe you weren’t listening to him, weren’t being very respectful, because of that? He had a reason for you to wait, it wasn’t arbitrary. But it sounds like your temper got away from you.”

Dean’s hands are making fists in the soft fabric of Castiel’s sleep pants.

“I was respectful,” he claims, though his voice is a lot smaller now. Castiel looks to Benny, who quirks his mouth and makes a see-saw motion with one hand.

“I think Benny did exactly right. He made the best decision while he was taking care of you, to be sure everything would go well with your enema. If it had been an emergency, that would have been different, of course, but it wasn’t, and you can call Sam tomorrow right after breakfast.” Dean is pouting, now. “I’m going to have Benny do your paddles, tonight. Not as a punishment, but so he knows how we do it for when I’m away, and so you start realizing he is just as much a Dominant in this household as I am.”

“I know that, Sir!” Dean protests, his eyes flickering from Castiel to Benny and back.

“Hmm. And yet, your behavior. Go and kneel to Benny and ask him, Dean. Don’t make me use the switch tonight.” He puts a snap of warning into his tone. He would prefer very much not to punish the Submissive tonight.

“Aaargh,” Dean groans, but reluctantly takes up the paddle again, to Castiel’s silent relief. It helps that he’s genuinely come to appreciate and even enjoy the twice-daily ritual, Castiel thinks. Sometimes he struggles to ask, but he really does enjoy it, and isn’t conflicted about it. And that tonight, he’s not spoiling for a fight, not really. He slumps over to Benny, the picture of reluctance, and slides to his knees with a sigh, staring fixedly at Benny’s kneecaps.

“Please end my day of Submission the right way, please paddle me with a firm hand, so I can feel how much you care for me.” As usual, he starts out prickly and too-fast, but ends softly.

“Of course, cher,” Benny answers gently. “Up you go, put yourself on the bench.”

Dean rises and leans over the spanking bench without further protest.

“You saw how I did it in the study,” Castiel says softly. “It’s a ritual, morning and evening. Be sure to leave the paddle on the skin after each strike.”

Benny nods, and pets Dean’s back and bottom for a moment, and then the paddle falls.

Dean starts to cry after just a few smacks tonight, but he’d he’d been very tightly wound, and watching all the tension leave him is beautiful. It takes long minutes to reach the count of ten, and after, Castiel stands to join them.

“Nicely done,” he praises them both.

“Dean is such a good boy,” Benny hums, and lifts Dean from the bench gently, hugging him close, stroking him from shoulders to thighs and letting him hide his face for a little while.

“Thank you Benny,” Dean hiccups, finally, pulling back, and his smile is just a little watery, no more sullen temper on his face.

“You’re welcome, brother,” Benny pats his hip.

“Tomorrow, Benny?”

“You got it boss. Y’all have a good night.” Benny beams at them both, and heads out.

Dean sighs against Castiel’s shoulder. “Tired.”

“I know, sweetheart. Let’s brush teeth and have you go potty. We’ll use a dilator tonight, I know how sore you are.”

Fresh tears spring up at that, but Dean doesn’t protest, and Castiel admires the pale pink of his bottom all through washing their faces and brushing their teeth, gently wiping Dean down after he uses the toilet, and then shepherding him back to bed.

“Twice in one day?” There’s a little whine in Dean’s voice, as Castiel gets him situated on his side, facing the wall, one leg pulled up. “You’re a sex fiend.”

Castiel has to laugh at that. “Twice? If I took you every time I had the urge to, it would be five or six. And that’s not really an unreasonable number, Dean. You’re tender and new, and you’re in training, so you’ve had plenty to learn besides being fucked. But don’t think yourself hard-used, here.” He laughs again at Dean’s indignant little huff.

Dean’s hole is much improved from the afternoon, almost back to normal, just a little redness and swelling. He still flinches and gasps when Castiel touches the lube syringe to it, though, and Castiel clucks to him.

“Deep breath, press out a little, there.” There’s no denying the little twitch and shiver of Dean’s hips is pulsing heat through him, but he lubes the boy carefully, thoroughly, gently sliding the syringe out and being sure there’s plenty of slick at the entrance.

“Phew,” Dean breathes out. Castiel drops a kiss on his shoulder, and Dean giggles in surprise.

“Step one of evil torture is over,” he intones, and Dean giggles again, bringing the heel of one hand up to his eyes.

“Hardly torture,” he snorts.

“That’s what I thought!” Castiel agrees, smiling. “I think you’ll enjoy this new dilator,” He reaches around to show it to Dean. “It’s for times like this when you’re sore. It expands, yes, but also ripples and pulses, so it’s not a rough stretch.” It’s a long, slim cylinder now, dormant in his hand, the squeeze bulb still resting on the bed.

“That might be cool,” Dean says, cautious. “Can I….I don’t have my cage on.”

“If you can come tonight, from this or when I’m in you, go ahead,” Castiel reassures him. If Dean can overcome the pain in his hole and reach orgasm, he will have earned it.

“Thank you!” Dean is suddenly eager, interested. Castiel grins, and eases the tip of the dilator in, watching Dean freeze, then remember to breathe, then pant as he pushes it home.

“Ow ow owowowow,” Dean mutters, his hips twisting a little, and Castiel stills him. Settles behind him, making him the little spoon, keeping the bulb in his own hand tonight. He slides his hard cock right into the hot, damp spot between his thighs, snugged hard against Dean’s taint, pressed tight behind his sac, and wraps an arm around him, pulling him back until there’s no air between them.

“You’ll get a stretch tonight, lovely,” he murmurs into Dean’s ear. “I will watch every moment.”

“Oh,” Dean breathes, and flushes right down over his chest. His eyes are bright, and yes, his penis is beginning to take an interest, though only just; when Castiel squeezes the bulb, Dean whimpers and squirms.

“Deep breaths,” Castiel tells him quietly. “The muscles have all stiffened, you have to let them relax.” He reaches up and palms Dean’s hard little breast. It’s true, he has been neglecting them.

“Hnng, ow,” Dean whines, complaining, as he kneads the heel of his hand into the rise of flesh below Dean’s nipple. At least he’s distracted from his stretching, Castiel thinks.

“I have a proposition,” he leans in and kisses Dean’s ear. “I want you to hold and rub and knead these any time you think of it. At dinner, when you’re watching television, during your enema. Any time your hands aren’t busy. And every time you do, you’ll get a tally mark. When you have twenty five tallies, you may have an orgasm any way you like.”

“Ohhh,” Dean whimpers, and Castiel squeezes the bulb again, loving the way Dean clenches his thighs and tightens around his cock. “Any way? Um. With my hand, even?” He peers back, eyes a little hazy now, but intrigued.

“Within reason,” Castiel tempts. “If you wish to masturbate while you’re being spanked, that would be fine. Or all alone in the bath, or with a dildo, or anywhere in the house. Absolutely. I will even assist, if you request it.” He digs in deep right over the largest angel gland in that breast with his thumb, and Dean hisses a little, squirming.

“I’ll be groping myself all the time to get points,” he objects.

“Mmm, yes,” Castiel agrees, voice going deep as he imagines it, Dean idly massaging his own breasts while he watches television, waits to be fed... “Not just holding, though, you must stimulate yourself for at least five minutes to get a tally. No cheating, lovely,” he mock-warns, and rolls Dean’s nipple between his thumb and finger, tugging it slow and long, just to watch Dean’s neck arch back in reaction. Dean doesn’t even seem to notice two squeezes of the dilator bulb as he does.

“O-okay...I think...okay, I’ll try,” Dean gets out, breathless, the temptation of getting his hands on himself obviously too much to be ignored, just as Castiel had hoped. His cock is well past half-hard now, Castiel notes with satisfaction.

“How does your bottom feel, baby,” Castiel asks, shifting back just a little so he can check. The flared base of the dilator extends out, and he runs his fingers down to where it disappears into Dean’s body.

“Sore, achey, oh, mm, ow,” Castiel watches with interest as he squeezes the bulb again, and Dean’s hole stretches a little wider.

“I think that’s enough,” he muses, and starts working the toy free without deflating it first. He wants Dean nice and open, loose and wet, and watching that red little anus stretch obscenely wide around the thick part of the dilator...he feels his own glands almost cramp, heavy and hot, his cock kicking up demandingly, already wet at the tip, wanting in.

“Ahhh,” Dean moans, twisting, thrashing a little, but he’s spreading his knees willingly, opening his hips, easing the way sweetly, and with one more rocking motion the toy slides free and he gasps in relief, rolling forward so he’s nearly face-flat on the bed..

“On your belly, Dean,” Castiel insists, slicking his cock with a quick hand as he sets the dilator aside. The remainder of the lube goes right into Dean, leaving him truly dripping wet. He puts a hand between Dean’s shoulder blades, pressing him down, and settles between his thighs. “You may grind on the bed if you like.”

“Yeah, yeah,” Dean breathes, thin and nervous and eager, rolling his face against the pillow. Castiel spreads his cheeks with firm hands, pressing them wide, clearing the way for his cock to ease forward, a gentle but insistent press.

Dean hisses through his teeth like a kettle, and flinches with his whole body, knees jerking reflexively up. Castiel follows the motion, ending up lying over him, propped a little on one arm, but blanketing him. He eases his cock forward and in.

“Squeeze and release, honey,” he murmurs, against Dean’s shoulder, the searing heat of Dean’s body almost stealing his voice. “Milk my cock, welcome it in. You can do it, Dean.”

Dean’s cry is muffled by the pillow, half-sob, half-laugh, but he obediently clenches, and Castiel sinks home smoothly, coming down to rest, chest to back, pressing him into the bed.

“Again, Dean,” Castiel holds very still, and Dean does, and that rich, tight ripple of muscle milks him perfectly. “Good, so good,” he praises, and Dean’s shoulders relax. “Tell me, how does it feel.”

“Burns, like fire,” Dean grits out, clenching again without having to be told, and gasping as he does. “Oh! Oh, but good, like with the toys, at the same time, I dunno, I can’t tell,” he’s breathless, struggling a little.

“That’s good, that’s all right,” Castiel assures him, flexes his hips, pulls out, slowly thrusts in again, listens to Dean moan and the sound might be pleasure, might be pain. He does it again, and then goes still again.

“Is it good, is it good for you?” Dean sounds restless, needy, a little worried, and Castiel winds his fingers through his hair and gives a sharp tug. He pops his hips forward, a hard little flex, and preens at the sharp gasp it drives from Dean.

“Oh yes. A gorgeous boy moaning in my bed, my cock balls-deep in his sore hole? Yes, it’s very good for me. Now work my cock, boy. I want to feel it.”

A quick hand slipped down under Dean’s body encounters his penis, still stiff, the skin hot and tight, so Dean has made a truce with the pain, the pleasure strong enough for now. He tucks it down out of the way, but where it shouldn’t be pinched if Dean rolls his hips, just as Dean clenches again around Castiel’s length, a rippling pull.

“That’s gorgeous, Dean,” he purrs, leaning into it. “So good. Make yourself come, baby. I know you need it. You’ve earned it today.”

“Thank you Sir,” Dean whimpers, eyes half closed, mouth a little open, his whole being focused on something he can’t see as his inner muscles work. He’s concentrating, face flushed pink, hands restless against the bedding and Castiel is proud that he he doesn’t even attempt to use them.

“Hands under your chest,” he urges, “hold your pretty little breasts, that will keep your hands full and help your nipples feel so good. Good,” he praises, as Dean automatically obeys, and whimpers as he does. “Are you close, sweetheart?”

“I...yes…” Dean’s ass works on him hard and urgent, as he rests his cock as motionless inside it as a toy. “Maybe...ohgod...I can’t…” he chews on his lip, hard, and finally breaks. “Help me, sir, please help me,” he begs, and Castiel instantly leans down, drags kisses across his shoulders, down his neck.

“Of course, of course I will. Keep squeezing, honey.” Slow and easy, without raising up at all, he pulls his pelvis back, dragging his cock over all the hot spots inside Dean, and then pushing back in. And again. And again. Dean’s hole is a frantic flutter around him now as his inner muscles go crazy, but his face is transported.

“Feels so good,” he slurs, “Oh god, sir, GOD, please, yeah, yeah, god, YES,”

“You come when you can,” Castiel tells him, working him from the inside, riding the heaves and bucks as he chases his orgasm without use of his hands.

“Ah...ohgodsir...AH….” he bites off the moan and comes silently, body arching, clenching like a vise around Castiel’s erection. The many days of denial have clearly done their job; he comes, and comes, and comes, contraction after contraction, his whole body jerking and shaking with aftershocks over a minute after his climax had begun.

As he slowly goes completely boneless, Castiel hums praise to him, kissing his back, nipping under his ear gently, and pushes himself deeper inside than he’s ever been. All the tension has been wrung out of Dean, and he’s flat on his belly, allowing this kind of deep, deep penetration that is the kind of thing that makes all of Castiel’s dominant tendencies purr. If he could live here, he would, he thinks, fleetingly and madly, and then strokes his hands over Dean’s sides, petting him.

“Oh my god, Sir,” Dean breathes, looking over his shoulder. HIs eyes are bright and clear despite the fatigue in his face, and there’s a wondering little smile on his face. “That was incredible.”

“You earned it with your amazing behavior today,” Castiel praises him, leaning up a little to kiss his jaw. The shift makes Dean squeak and tense. “Shh, shh, easy,” Castiel gentles him. “I haven’t come yet, but I won’t be rough. Take some deep breaths.”

Now that the impending orgasm isn’t distracting Dean, Castiel knows that even still, this kind of intrusion will start to burn and ache soon. And indeed, Dean tries to ease his thighs closed, but Castiel is between them with his own, and blocks the motion. Then his hips twist a little. His buttcheeks clench, then relax, and his breath starts to quicken.

“Tell me,” Castiel murmurs.

“Big,” Dean gasps out sharp, almost unwillingly. “Like it’s splitting me open but slow. Little more every second. Sir. Sir.” He tries to raise up on his elbows, but Castiel’s weight over him keeps him down.

“Breathe. Let your body adjust for a moment,” Castiel orders, and Dean subsides. His eyes are a little wet, and Castiel’s cock jumps, hardening more. He wants to accustom the boy to this. If they’re to be together, perhaps long-term, he’ll have to push a little more every day to be sure Dean understands what that entails.

“I”ve been in you this deep before but only actively,” he says, quiet but firm. “This is what it feels like, honey. I may want you like this while I read, occasionally. Or perhaps in my lap while I dine with other dominants. A sheath for my cock, all hot and tight. It will get easier with practice.”

“Yesssir,” Dean whines, and then chokes a little out of nowhere, like a wave of pain had caught him off guard. His face crumples and he’s crying, and it’s gorgeous, it’s beautiful.

“So good for me, that’s very good,” Castiel praises, and gently thrusts once, twice, and comes. It’s gentle and easy and sweet, and he kisses and praises Dean even as he’s carefully pulling out.

As he wipes Dean clean and kisses his face, tucks them both in to bed for the night, all he can think is that he sincerely hopes tomorrow is completely uneventful. They’re all tired, and with Gabriel safely home, perhaps tomorrow will be a welcome return to routine.

Chapter Text

Over the last couple of weeks, as Dean has been spending some time in the afternoons learning more about dynamics and stuff, he’s started thinking about his own reactions and submissiveness and things like that in a different way, kind of. Like, there’s a part of him that he thinks of as his ‘sub brain,’ and when he got to the training house, it was tiny and silent and pretty much sick and busted. Like a stale little walnut, inside his head, hard and sour. Now it’s a lot bigger. Sometimes it’s his whole mind and those times are kinda amazing, but sometimes, it feels closed-off and defensive, like it’s been wrapped in leather left to dry in a thick rough shell where nothing can reach it. Sometimes, like this morning, when Castiel wakes him up, he can already tell it’s going to be a hard morning, because his sub brain is prickly like a cactus. It isn’t soft and waiting and easy, open to listening to Castiel, to being obedient and good; it’s got nasty little prods of temper and defiance instead like long sharp thorns.

He’s pretty sure Castiel can tell these things too, without him even saying, because when Dean just rolls over and buries his head under the pillow with a groan, he stays quiet and pets his hip for a few minutes.

“Talk to me, Dean,” he eventually says, his voice still a little deep and gravelly with sleep. “Is your bottom still hurting you?”

“It’s my ASS, I’m not a baby,” Dean snaps into the pillow, before he can even think twice about it, aggravated beyond belief for no reason he can tell. “And yeah it’s sore but I’m fine.”

“Hmmm.” He doesn’t get reprimanded, which is surprising, but Castiel rubs his hip a little harder, then shifts him gently. “Let’s have a look.”

Dean doesn’t resist having his cheeks spread, or the way Castiel’s finger probes his sensitive hole, but he doesn’t help, either.

“You look much better,” Castiel says, and pats him. “Come on. Time to get up and start the day.”

“I don’t want to,” Dean tells the pillow, mulish. “I should get to sleep in some days.”

“Hmmm,” Castiel says again, a little deeper. “Dean. I can see you’re out of sorts this morning. I’d like to let you try to work through it, but not if you’re going to be this disobedient. Will you need the switch before your paddle, this morning?”

Dean kicks at the bed, sullen, not wanting to let go of his mood. He shakes his head at Castiel’s question and rolls out of the bedcovers and to his feet without any more protests.

Even with prickly-brain, Dean isn’t bold enough to shrug off Castiel’s hands while he’s peeing or brushing his teeth or when they jump in the shower. He lets himself be washed, and dried, and tries his best to get back to equilibrium, even as he holds himself as far away from his Dominant as he can. By the time they’re dry, he feels a tiny bit more clear-headed, at least.

“Get your paddle and come here,” Castiel tells him, and instead of his normal chair, he’s sitting on the big soft loveseat, and pats the seat beside him. A little warily, Dean sits there, his paddle in his hand. He keeps his eyes on Castiel’s face, wondering what this is all about.

“You’ve been missing your morning workouts, baby,” Castiel says, reaching out and drawing him closer. Dean doesn’t resist, blinking in surprise. “In addition, our routine has been disrupted for nearly a week, now, first with Paul, then with recovery, then with Gabriel’s visit. It has been a lot to take in, I know. This kind of disruption can have a huge effect on the mindset of both Dominants and Submissives, especially young and inexperienced ones, and the fact that you’ve been so resilient is actually very surprising and excellent.”

That startles a little grin out of Dean.

“Yeah?”

“Yes indeed. I can tell it’s catching up with you right now, though. I know you’re not being naughty on purpose, you’re just reacting to the loss of structure and routine you need.”

Dean scoffs, scowling. “I’m not...I can adapt to anything. I don’t need. It’s not.” He cuts himself off, uncertain, at the way Castiel lifts a brow.

“If that’s so, then how did you wake up already so cranky and off-balance?” Stupid Dominant, he looks so knowing, and shit, with that dumb little smile. Dean scowls harder. “I can do a few things, here. I can give you your paddles, and that will help, and we can go on through our morning, and let you try to work your way through the rest of this on your own. I can do your paddles, then a much harder set with the small strap, which I believe will help you rebalance yourself and start the day well. Or instead of the small strap, I can dress you in panties, bra, and one of your nighties, before we go to breakfast. You may choose.”

Dean realizes his mouth is hanging open, and he closes it, and shakes his head.

“My sub brain probably wants number two,” he says, huffing, still mad that he even has to be paddled, this morning. He’s explained his ‘sub brain’ theory to Castiel, who, after determining that Dean wasn’t pretending his submissive side was a whole different person or anything, was more than fascinated by how Dean ‘conceptualized his Submissive needs and desires.’

“But…?” Castiel prompts him gently.

“But it’s angry and full of thorns right now,” Dean finishes, helpless to describe it any other way.

“I think the second one might smooth away those thorns,” Castiel suggests. “Ease some of that anger.”

Dean struggles with it. He does. He knows it’ll work, knows Castiel knows what he’s doing, what he’s talking about, knows that once it is done he will be so much happier and even grateful and content, but fuck, he can’t, it’s so hard.

“I can’t,” he grits out, into the waiting silence. “I can’t pick, sir, I can’t make myself. Please.”

“That’s okay. I’ll choose for you, honey,” Castiel says gently. “We’ll do number two, thorns or not. Remember, this isn’t a punishment. This is to help you find your feet again.” He drops a hand down between Deans thighs and holds his cock, rolls it in his palm before wrapping his fingers around it, and Dean squeezes his thighs and twists his hips, trying to dislodge him. “Stand up, come on, up you get,” Castiel tugs his penis, and Dean follows the pressure instantly, no thought of resistance in his mind. On tiptoes to avoid any tugs, shocked into compliance at being led by his cock, he’s brought to the spanking bench directly and without a fuss.

“Good boy,” Castiel praises him, warm and low, like he hadn’t just forced Dean into position by his dick, and when he tries to bend Dean over the bench, he stiffens, resisting, contrary.

“I decided I don’t want a strap, I wanna work it out on my own,” he says, suddenly feeling like it, feeling like going against whatever Castiel decides, because...because he’s mad, and he wants to.

“You asked me to choose for you, and I did.” Sir sounds very firm, now, and he’s pressed up all along Dean’s naked back, his bare skin warm and weirdly reassuring. Dean doesn’t want reassuring now and he tries to squirm away, but Sir holds him tight until he stops. “I would rather not punish you when you wake up like this, Dean, because I know it’s at least somewhat outside your control, while you’re still so new at managing your reactions. But I also know that you are capable of controlling yourself, and if you keep demonstrating that you need firm correction with your behavior, you’ll have the switch before the paddle and the strap.”

“NO!” Dean bursts out, kicking back with one heel, suddenly outraged at the thought. “I don’t want the switch OR the strap! You said I could choose! You just wanna use the switch because you fucking get off on it--” he’s cut off sharply when Sir’s hand grabs the back of his neck and shoves him down to the bench, the other hand getting his wrist bent up behind him in a grappling hold.

“Claudia?” Sir’s voice sounds so calm and normal and Dean’s near tears of rage, here, it’s not fucking fair, it’s not, his stomach is in knots and he reaches back to try to pry Sir’s hand away, and he hears Claudia answering from the open doorway. “Can you bring me the switch, please? My hands are just the slightest bit busy. Thank you, my dear.”

“Here you go, boss,” she’s right there, the traitor. “Can I get you anything else?”

“Actually, yes. The cuffs by the bed? And the leather set, in the tall cabinet. Thank you.”

“Noooo!” Dean howls. He’s never cuffed for his paddling. It’s almost insulting how easily Sir gets the cuffs around his wrists, and his wrists bound to the bench, though.

“Should I have Angelique hold breakfast?” Claudia again, from the door, and Sir answers like they’re talking about the weather or something.

“No, I think we’ll be down at the regular time. Thank you again, Claudia.”

“Anytime, boss. Page if you need anything else.”

“I apologize for not seeing sooner what state you were in, Dean,” Sir tells him, calm and serious, even as Dean is yanking futilely against the wrist cuffs and trying to slide sideways off the spanking bench. “Now that I understand better how quickly you can escalate, I will be more watchful and vigilant in future. Now be still, and spread your legs, so we can get this fixed, and help you feel better. Your little hole is still sore, so you’ll have three on your penis, two on your anus, and five on your buttocks with the switch, before the paddle and the strap.” On his cock? He hasn’t ever been switched there, Sir can’t do it, it’s way too much.

“You can’t, you can’t do that,” Dean cries, and clamps his thighs closed as hard as he can.

“Spread your legs,” Sir says, deep and stern, and Dean tries to kick him.

“Make me,” he snarls, and something in his sub brain, behind the vicious thorns that are goading and prodding him into all this nastiness,sits up and pays attention, suddenly. Can he? Will he?

“All right,” Sir says, just as calm as before, and a cool leather band, wide and flat, is being pulled tight around Dean’s left thigh, dragging it wide and binding it to the spraddled leg of the bench. He’ll be splayed obscenely open, he realizes, and he starts to fight for real, twisting and kicking with his free leg, gasping for air, in relief, almost like a release.

“Go ahead and let it out,” Castiel murmurs to him, even as he’s corralling the other leg, implacable, forcing it down and out, strapping it to the other side. Then he binds Dean’s ankles one by one

“NNNNNNGGGGG,” Dean screams through his teeth, arching against his bonds, and it feels so good to just be able to fight it, to put all his strength against something, even if he knows he won’t get loose. Like he’s letting out all the anxiety and restlessness and anger and frustration and fear that have been building and building in him.

“One more,” and another wide band around his waist, snugged up right below his ribcage, keeps him from lifting even an inch off the bench, no matter how he heaves and pulls. Which he does, for what feels like twenty minutes, until he’s sweaty and actually a tiny bit tired, and panting.

He blinks tears out of his eyes and Sir is crouched in front of him, eyes on his face, calm and waiting.

“I can’t move,” Dean huffs out. He’s still mad, but the thorns are more blunt, now.

“That’s the idea,” Sir nods. “You won’t hurt yourself here, no matter how hard you struggle.”

“I...I feel better now,” Dean offers. “I’m sorry I kicked you and yelled at you. I think it’s okay if we just do the paddling.”

“Do you,” Sir says, flat and unamused.

“Yes,” Dean nods, fear starting to trickle in now that the worst of the red fog of anger is gone. He doesn’t want the switch, he doesn’t. He tries to close his legs, he can feel cool air on his asshole, the delicate skin behind his balls, he’s totally helpless, spread out wide, knees a little bent, his boobs crushed hard against the bench by the waist band, it’s not comfortable. He can’t move even an inch. “I tried to get off the bench for a long time, we’ll miss breakfast.”

“You fought the restraints for a grand total of three minutes,” Sir informs him. “We have plenty of time.” He stands, and Dean can crane his neck far enough to see him take the switch off the table.

“Sir! No! Don't, please....Fuck you, if you do this, you sadistic asshole,” he blurts, as Sir just walks around behind him.

“And there it is,” Sir murmurs. “Three on your penis, Dean.”

He doesn’t draw it out, just gets back between Dean’s legs and there isn’t even really a sound and then the pain is like nothing Dean’s ever felt, worse than when he’s whipped on his hole, worse than anything. His whole body convulses and he can hear himself gagging, he’s trying to scream and he’s choking on spit, his body doesn’t know what to do.

“One,” Sir says. “Breathe.” A second hit makes Dean want to puke, it hurts right up into his belly, he can’t move, can’t rock or squirm or anything to escape and distribute the pain, he just has to take it, held still by the straps, absorbing it as it comes. It’s agony, he can’t, he’s screaming so loud his ears are ringing. “Two. One more.” Sir’s voice sounds far away. A third streak of fire on his cock and the relief of knowing this part’s over, that’s all there will be washes through his mind, even as it makes him strain every muscle in his body trying to levitate off the spanking bench, escape, get away. “That’s three. Two on your anus, now, sweetheart. You’re doing very well.”

The thorns are almost gone, and the realization drifts through, disconnected, he hurts too much to care, his face is all wet, his cock is burning up. He tries to pull his hips forward, tuck them down, hide from the switch he knows is coming, but with a snap his hole is seared and he can’t get away or curl up or kick, just howl out his pain.

“One,” Sir’s voice is so calm and steady. Like a rock Dean can cling to. SNAP and he shrieks and tries to crawl through the bench, hot/cold stabbing searing pain feeling like it’s encompassing all his softest parts, his cock, his asshole, all the places between. “That’s two. Good job. Now five on your bottom.”

When the first one falls, something hard and sharp and angry in Dean’s mind finally breaks in two and fades to nothing, chased out by the pain, the helplessness, the calmness of Sir’s voice.

“I’msorryI’MSORRY,” Dean heaves out between wrecked, wet sobs, cleansing remorse finally leaching poison out of him, or at least that’s what it feels like right now, dizzy and sick as he is with pain. The second and the third knock screams out of him too but somehow he’s found his words, too. “I’m so sorry I was bad, I was so rude and bad, I’m sorry sir, so sorry,” he’s chanting it when he can get his breath.

“You’re forgiven, Dean, you’re doing so well.” The last two are quick and fast and then Sir’s undoing the wrist bindings and the one around his waist and tilting the spanking bench up and pulling Dean into his arms. Sobbing and shaking and needy, Dean clings.

“There’s my sweet good boy,” Sir murmurs against his hair. It sounds like music in Dean’s ears. Sir rubs his shoulders and back and kneads the back of his neck where it feels so good, and then down by his tailbone, where it’s a little sore but then a good ache. When he finally pulls back a little, he’s smiling, the wide one with the eye crinkles that shows his white teeth.

“You should feel how much more relaxed you are, Dean. That was quite a tantrum, hmmm?”

Feeling small and still ashamed, Dean nods a little. His legs are still bound to the bench, it’s a little awkward, or he knows he’d be shuffling his feet.

“I have you in hand,” Sir tells him seriously. “I’ll enforce the rules and your boundaries. So will Benny, so will Meg. You’re not adrift, honey, you’re not alone, we are here to help you. Even on a bad day, we won’t let you fall. We committed to that when you came here and we won’t fail you.”

Dean’s sub brain, already feeling bruised-soft and purry and wet with tears, furls open somehow hearing that, and he sniffs hard as he nods. “Thankyousir” he says in a near-whisper.

“You are so welcome, Dean,” Sir says in this warm, rich, pleased voice that’s like having a hand wrapped around Dean’s cock. He sighs with pleasure. “Okay, let’s finish your morning properly. Back down on the bench, I won’t bind your hands again, but I like the way the leg straps are holding you open, it’s lovely. We’ll do ten with the paddle, then ten with the small strap.”

Dean feels his face crumple helplessly.

“Honey,” Sir says, gentle but firm. “This is not punishment. That is done, you are forgiven, the slate is clean. This is to help start your day correctly.”

“But I already hurt suh-suh-so much,” Dean wails through a fresh sob, even as he’s laying himself back down prone on the bench. The pain from the switch has faded to a dull, angry throb that wakes back up every time he moves, most markedly in his cock.

“It sounds like that will be an excellent reminder of your manners today,” Sir’s voice holds no sympathy. “Hold the hand grips, Dean.” Still sniffling, he does.

“This is your paddle, that you love. First we do ten, then ten with the little strap. You know neither of these will ever be used in a punishment. And none of your punishment implements will ever be used for anything else,” Sir is talking to him, quiet and calm, and it’s a lifesaver. He does know that, and it calms something frantic inside him to hear it again. The first paddle slap falls, familiar and steady, and Dean coughs out a yelp as it lights up the switching welts again. But it is so comforting. He knows this, every morning and evening, the paddle falls and lingers, ten times, with or without punishment.

He actually loses count somewhere in the middle, and feels Sir rubbing his thighs, running fingers along his crack and balls, intimate and intrusive and knowing, with a little surprise when he’s done. He’s relaxing like a puddle on the spanking bench, pain or no pain, now. His sore cock is all soft and scared still but the rest of him is starting to feel way better, more normal, somehow. His sub brain feels like it’s had a deep tissue massage.

“All done?” He peers over his shoulder to look at Sir, who’s smiling at him a little.

“Ten with the small strap.” He shows it to Dean. It’s wide and flat and short, leather. It doesn’t look so scary, though Dean knows Sir could make it very nasty if he wanted to. “It won’t be rough, just a little extra for a very hard morning.”

“O-okay. Thank you Sir.” Driven to it, Dean huffs and smiles a little. “Please start my day of Submission the right way, please paddle me with a firm hand, so I can feel how much you care about me?” The words roll so sweet off his tongue, completing the ritual, making him feel warm inside.

“It’s my honor and privilege, Dean,” Sir says seriously. He leans down and gives Dean a quick kiss on the mouth, then the cheek. Dean hums, pleased, and then lays his head down on the bench, waiting for the strap to fall.

It’s different than the paddle, warmer, more of a thud than a smack. Over the switch welts, it’s so painful. Dean shrieks once, when it hits across his sit-spots, so tender, but otherwise he just lets the strap knock all the last hard, sharp anger that might be lingering right out of him.

“So good,” Sir is telling him before he knows it, gentle hands releasing the bindings. “I am so proud of how you took that, Dean, that was very challenging, and you were perfect.”

God, yes, give him more of this, when Sir tells him this stuff it’s like hits off a crack pipe. Straight shots to the pleasure center. Dean grins, a little dizzy, and lets Sir get him off the bench and pull him into his arms. It’s so worth it for this part, where Sir holds him and rocks him back and forth, petting him, telling him how good he is. Dean preens a little. That was pretty intense, he figures. Sir whipped his cock. Speaking of which!

He looks down, suddenly worried, only to find there is absolutely no sign of the whipping on his dick. What the fuck!

Sir is laughing at him, a warm chuckle, even as he’s putting away the paddle and switch and strap.

“The thing about targeting the penis, or anus, or testicles, or nipples--or labia or clitoris, in a female Submissive--in punishment, is that I can achieve a remarkable effect without needing to strike very hard or do any damage,” Sir informs him.

“It doesn’t feel like you didn’t do any damage,” Dean cries in protest, but he’s smiling a little at Sir’s good humor.

“And isn’t that the point?” Sir throws on what Dean thinks of as his around-the-house clothes, soft jeans and a dress shirt, and then leads him out the door. “Now, let us not keep breakfast waiting. And I believe you have a phone call to make, after?”

Shit, that’s right. He has to call Sammy! Wincing a little at the way walking pulls at his asshole, his sore butt, Dean scrambles to catch up with Sir and head towards the food.

Benny and Meg are already at the table--Meg’s back? He knows she was in Austin for something--and Cole and Ash wander in just as he and Sir do. Breakfast is funny, sometimes nobody shows up, sometimes everybody does.

“I’m glad to see Dean survived whatever it was that caused that amazing ruckus,” Meg says, grinning at Castiel, who laughs a little, and ignores Dean’s blush and pause to guide him firmly to the table.

“Dean had a magnificent temper tantrum this morning. Attention- and correction-seeking behavior, both of which I was able to provide for him immediately,” Castiel answers her dryly. Dean wants to sink into the fucking floor. “Dean, turn around, bend, and spread your cheeks. Show Dom Meg, Switch Cole, and Dom Benny your hole.”

Dean’s thoughts stutters to a halt. What? What’s this. He meets Castiel’s level stare, and it’s uncompromising. Slowly, he turns around, his face like fire, and bends at the waist, reaching behind him to spread his sore cheeks open. Oh fuck oh fuck it’s embarrassing, they’re looking at him, at the breakfast table, but his sub brain is going gooey and warm, thumping a little like a pulse. It likes being looked at like this, like he’s a sex toy.

“Today at least, we’ll be doing strict discipline with Dean. He is to obey all rules absolutely until he re-settles after the upset of the last week. As you can see, his hole is nearly recovered from use, so if it’s a minor infraction, switch his anus, unless it is too sore from punishment or use. For more serious problems, his anus and penis. Anything worse than that, call me, and I’ll handle it, and we’ll re-evaluate as we go. You can relax, Dean.”

“What?” Dean asks, standing straight and turning around, looking to Castiel, who’s smiling at him warmly.

“Just be a good boy, and you don’t need to worry about it at all. Remember the rules you’ve had since the beginning? I’m not talking about anything new. Treat everyone in the house with respect, and obey my commands. If I’ve left you with one of the others, obey them as well. That’s all. This is just reinforcement, in case things have slipped a bit. In case the thorns come back.”

“Oh, okay.” Dean breathes out, relieved. Jeez, that had sounded scary for a minute, like everyone was gonna be lining up to punish him or something. He's going to just have to remember to be careful today, is all, not step on anyone's toes, because no way does he ever want that switch touching his cock again.

“Let’s eat,” Meg claps her hands, and Dean goes down to his kneeling cushion with relief.

For a few moments everyone’s busy getting food and drinks and stuff, and Dean’s starving, he can smell bacon and sausage and pancakes. All the best things. He can’t kneel back on his heels, either, ‘cause his butt is hurting like fire, so he’s kneeling up, where he can see all the foot but not touch it, which is like a special kind of torture.

“Here.” Sir rolls up a small pancake, dips it in syrup, and holds it to Dean’s lips. He takes it all eagerly, and chews and swallows, blissful.

“Maybe not so much ready to head back out into normal dating and contracting just yet, huh?” Dean hears Benny say with some humor, once they’ve all slowed down on eating a little, and Sir laughs wryly with a nod.

“Dean has a call to make after breakfast, and I’ll call Gabriel so he can update his notes, as well. Then, Cole, you’re ready to resume normal morning workouts?” Dean can’t see Cole, but it seems like he nods. Man of few words, is Cole. “Then I think Meg and Benny, we should get together with Dean and talk about plans for when I’m out of town.”

Dean makes a face at that. He’s not really looking forward to Sir being gone for five days, though yeah, he knows that Sir has a plenty of responsibilities, and it’s not like Meg and Benny are a bad second option.

“You bet, Boss,” Meg answers. “I’m free after eleven.”

Sir looks down at Dean. “I see you aren’t interested in earning a tally mark this morning,” he says easily, and crap, Dean had totally forgotten it. “Dean can earn a point towards an orgasm by self-stimulating his breasts and nipples,” he goes on to the table in general. “He must do it for five minutes at least, both breasts, and it must be active, not just cupping or holding. I’ll put a sheet on the shared drive, and any of you can record a tally for Dean if you note one down.”

“How many for a reward?” Benny asks, and Dean cranes up to look at him across the table.

“Twenty-five,” he says. Benny grins at him, and he smiles back.

“That’s great, cher. A nice treat, huh? Boss could just put you in a breast trainer or in time on a board, but this is a lot nicer.”

Dean feels himself flush red, and nods. He’s not sure what those other things are, but when Benny puts it that way, this incentive program thing Sir has offered really does sound like an excellent deal.

“One last thing before everyone goes,” Castiel says, in his ‘boss voice,’ and it’s great to see how everyone sort of perks up and comes to attention. “I know that Gabriel interviewed some of you yesterday, and nothing that happened during Dean’s inspection was secret, so you’re aware of some developments. However, until and unless a waiting period is complete and a contract is offered and signed, Dean is still a Trainee Submissive in this house. It’s fine to look forward and wonder, even hope, and I’ll admit to some of that. But never to assume. Dean will not be trained for the preferences of any particular Dominant. That is critical. If you feel that there is any bias in his training, you are to bring it to me immediately, or Gabriel, if you feel more comfortable.” He looks sternly around the table, meets the nods there with approval. “There are a hundred ways things could change, and it’s vitally important that no matter what, Dean graduate from this program with the tools he needs to be healthy, fulfilled, and happy with whatever Dominant he settles into a relationship with. Understood?”

A chorus of agreement replies to him, and he smiles. “I know I can count on you all. Thank you for all your hard work, dedication, and excellence. You’re the best. Now get out of here and do the work I pay you for.”

He shoos them with his hands.

“Yes Boss,” Benny and Meg say in unison, with Cole and Ash a beat behind, and they’re gone before Sir even gets Dean up off his pillow.

“Here, Dean,” Sir raises him to his feet, and pulls him to stand square. He pulls Dean’s cock cage out of his pocket, and Dean claps his hands over his mouth to keep from whimpering out loud. “Hush now,” a gentle scold, as Sir gently works his tender cock into the cool metal. It actually feels kinda nice, he realizes, cold and smooth, and he sighs out a long breath. Sir pats him gently on the butt once he’s all locked in and tucked away.

“How do you feel?” He asks seriously, and Dean thinks about it a minute.

“A lot better,” he says honestly, with a little smile. “Uh, steady? Not prickly or pissed off anymore. I wanna be good and I’m not mad about it.”

“That’s very good,” Sir praises, and Dean beams. “Now you should go call Sam, so you can have a good talk before Cole comes to get you. And Dean? I’m proud of you.”

Suddenly shy, Dean tips his chin. Then he ducks in super-fast and kisses Sir, awkward and quickly, before hurrying out of the room to call Sammy and see what the heck he’d wanted last night, anyway.

Chapter Text

“All right. Yes. I’ll see you Friday,” Castiel says into the phone, and hangs up, finally. He does love his brother, but the man can talk like none other.

“Dean and Meg still aren’t here,” Benny points out from the chair in the little sitting area across the room, as Castiel gets up from behind his desk, stretching out the stiffness of long immobility “You’ve got a few more minutes, no rush.”

“I don’t think I could listen to Gabriel explain more about the second floor of the new Dominant center for another moment,” Castiel confesses, and goes to the big cabinet by the window, grabbing a length of soft rope and the black leather arm bindings that he knows will fit Dean, and then picking up the switch from its holder by the door before settling down in the loveseat beside Benny’s chair. Meg ducks into the room with a wave, and Benny beckons her over. The late afternoon sun makes the whole room glow warm and golden and welcoming, and Castiel smiles at them both as he gets comfortable.

“Hey boss, Benny. I passed Dean, he’s on his way.” she says, sitting with her customary grace across from them both.

Benny arches an eyebrow at the restraints in Castiel’s hands. “Planning to wrap the boy up?”

Castiel shakes his head with a small smile. “The more I train Dean, the more I realize he is a Sub who needs what I think of as heavy work. He learns with his body, and once he struggles and strains against resistance, he calms, and can hear and learn. Even then, though, unless he’s actually done something himself, worked through it and learned it physically, he doesn’t really know it. I’ve got these in case he needs them, if the conversation turns difficult.”

Meg has a thoughtful furrow on her forehead. Castiel can almost see the wheels spinning. “You leaving him in our hands so he can be in our hands for a few days?” she guesses, and he is always so impressed by her.

“I can tell him a hundred times that you two are Dominants in the household, to be trusted and obeyed, but until he’s been in at least a temporary dynamic relationship with you, and absorbed it through the skin, with the same kind of body learning he’s had with me, I doubt it’ll be anything but superficial.” He tips his head at Benny. “I know that now that he’s not in distress, we’ll be opening up the house for service, short-term contracts, and more, and he’ll need to be a little more reliable with you both.”

“And you don’t like doing diaper training,” Benny interjects, with a grin.

“And that,” Castiel agrees, with a laugh. “So tedious.”

“Hey, sorry, Claudia needed help getting a big bin out of a cupboard,” Dean bursts in, a little breathless and bright-eyed.

“You’re not late, it’s fine,” Castiel assures him, and waves him over to the cushion at his feet. “Kneel, wait.”

“Right, right,” Dean hurries and joins them, dropping to his knees in the Wait position. “I talked to Sam, I gotta ask you some stuff, Sir.”

“All right.” Castiel looks down, and Dean’s pretty face is looking right up at him from his knees, big green eyes hopeful, and he has to reach out and cup his cheek with a hand. “Take a breath, sweetheart. We’re here to talk about what you and Benny and Meg will be doing while I’m away. Can it wait until after that?”

“Maybe? I mean, it’s kind of related? Can I ask first and then we can figure out if it can wait?”

“That is some extraordinary logic,” Meg murmurs, and Dean shoots her a wrinkle-nosed glare over his shoulder. Castiel gently turns him back.

“Yes. All right, ask,” Castiel has to chuckle at Dean’s answering smile. It’s not like they’re on a time crunch, here.

“Okay, so,” Dean dives right in, turning a little so he can see Benny and Meg, too. “So, my Dad is going out hunting with some friends. And Sam’s on break from school, but only for a couple of the days he’s gone, so he can’t go with. Normally he’d stay with me, or our Uncle Bobby. He’s not really my uncle,” he tells Castiel, like an aside. Castiel, his chin now propped on his hand, just nods, transfixed by this singular recitation. And feels a little anger is growing inside him yet again, at this glimpse into the lives of the Winchester boys, how hard they've been. “He’s my dad’s really good friend, and he’s my boss. But anyway, Sam says Bobby has plans to go to Tampa for a classic car convention and to buy a bunch of really important parts. Sam is gonna just stay home alone. It’s not like he can’t do it. He’s almost fifteen. But can’t he come stay here for a visit? It was awesome last time he came.”

Dean looks at Castiel, then at Bobby, then at Meg. The hope on his face is ridiculous.

“What days, and have you even asked your father about this?” The first and most important questions, Castiel believes.

“He’d come on Wednesday and leave on Saturday morning first thing,” Dean answers promptly, starting to grin, his hands clenching a little on his thighs, almost bouncing on his knees. “We didn’t ask Dad yet, had to find out if it was even a possibility first. Sam thinks it would be cool with him.”

Castiel looks at Benny and Meg. That overlaps one day with his own trip. Benny gives him a shrug. He clearly doesn’t care. Meg is obviously more torn. She taps her fingers on her knees for a moment.

“As long as our plans can go on with just minimal adjustment,” she finally answers his silent question. He nods at her. That’s entirely fair. He knows she’ll adjust what she needs to for Sam’s sensibilities, while still doing what Dean needs.

“Before we make any plans, I want to talk about the next week or so with you,” he tells Dean, serious, bringing the boy’s eyes back to him, his shoulders straightening back out and coming almost to attention. “For one thing, having Sam here for that long would ensure that he would see you in your normal routine here every day. That was something that was very concerning for you, last time.”

Dean deflates a little, and nods. “I thought about that,” he says, hesitantly. “I think...I think it’ll be okay. It was okay last time. We’ve talked a lot on the phone, and it’s so...it’s a lot easier now. We’ve talked about a lot of stuff. It’s cool.”

“That’s very good, Dean,” Castiel tells him, warm and pleased, and watches Dean’s cheeks flush pink at the praise. “I also want to tell you about a new challenge we will be setting for you while I’m away. Since Sam would be here for one of the days I’m gone, it’s something you’d need to take into consideration. Here, hold out your arms for me.”

Looking a little bewildered, Dean does, and Castiel gently wraps the arm bindings around one arm, then the other. Wide, supple, smooth leather fastens around Dean’s biceps, his forearms, his wrists, and then straps connect one arm snugly to the other in front of him. Now that the prospect of Sam being here is in the mix, he’s going to make sure Dean has this to push against if he needs it.

“I don’t get it,” Dean says, a little flat.

“Benny? Meg?” Castiel invites them.

“Can I take him a minute, Boss?” Benny asks politely, and Castiel nods.

“Come here, cher,” Benny says, and helps him stand, still confused, and move to the couch with him. He sits them close together, his arm around Dean’s shoulders, nice and snug. “While the Boss is gone, you know he’s leaving me an’ Meg in charge, yeah?”

“Yeah,” Dean nods, relaxing a little at all the touch, Benny’s calm everyday voice.

“He’s been nice enough to give the two of us something we really like to do, and something he knows is gonna be a hard job for you, to keep us all busy while he’s gone.” Castiel glances at Meg, and she’s leaning close, smiling a little in agreement, obviously standing by as backup. Excellent. “We’re gonna be training you to use a diaper for the five days he’s away. So you need to think about that when you make plans with Sam, make sure you’re okay with that in your mind, considering I know it’s been a tough thing for you, before.”

So calm and matter of fact, it looks like it takes a few long moments for the meaning of his words to sink in. Then Dean’s eyes widen a little. He looks at Castiel, who nods at him seriously, at Meg, who’s still in position, and finally he arches back to stare at Benny, who’s like the Buddha, he’s so mellow.

“What...I mean. In the age play room, the whole time?” He sounds honestly confused, not raging, not scared, and Castiel feels a little pride bloom in his chest.

“No, Dean,” Meg takes that question. “We may spend some time there, especially in the beginning, to make it easier for you. But you’ll be wearing the diaper all the time, in the house. By the time Castiel comes home it should be much more comfortable for you.”

“Why?” Now Dean twists his body a little hard, like he’s trying to stand up, but Benny holds him, and he hits against the armbands, and as his muscles strain and stand out, the rest of him eases. “Why?” he repeats again, a little more plaintive as he sags back against Benny’s side.

“For one thing, because it’ll please your Sir,” Benny tells him firmly. “For another, because he thinks it’ll help your training. And it’ll get you past some other resistance you have, and accept some things you’ve been fighting, and you'll like it in the end. And it’s a hard thing that you’ll need to work with me and Meg real closely for, real intimately, so your Submission will get stronger for it. Easy, little brother.” He holds the back of Dean’s neck in a big hand, rubbing there, as Dean grits his teeth a little and relaxes from another instinctive yank away from him.

“Is that what you meant when you said it was okay for Sam to come as long as you didn’t have to change your plans?” Dean asks Meg accusingly.

She nods. “Friday would be our first day of training,” she answers, without a hint of apology. “We would keep Sam from seeing anything sexual or inappropriate, but we will not postpone for him entirely.”

“I’m not wearing one of those things in front of Sam,” Dean declares, and Castiel’s eyebrows go up.

“Remember what I said at breakfast, Dean,” he warns. The switch is ready on the arm of his chair, and he knows Dean knows it’s there. Dean’s mouth snaps shut, but he looks pale and mulish.

“We could perhaps discuss you wearing one of your dresses over top while Sam is here,” Meg says. “But if Sam is here on Friday, he will be here while you’re wearing a diaper. The other option is for him to not come, or to leave a day earlier.” Her voice is like steel, and the Dominance in it is sharp as one of Dean’s own stilettos. “This is not up for negotiation, Dean.”

Castiel can almost see the thoughts flying through Dean’s head. That he’ll figure out how to get out of it while Sam is here. That he might wear it but he won’t use it. That he’ll get them to relax the rule once Castiel is gone, or sneak his noncompliance past them. They’re practically written on the boy’s face, and it’s probably a sign of the sadist in him that he almost has to bite back a smile, imagining the reaction Dean is liable to get if he tries any of that on Meg and Benny.

“Sam’s gonna want to spend all his time in your library anyway,” Dean finally says, grudging. “I guess...I guess it might be okay. If it’s okay with you, Sir. And my Dad.”

“If you two are all right with a day of an extra Winchester under your responsibility?” Castiel wants their verbal agreement, before giving the go-ahead. When Meg and Benny give it, he nods to Dean.

“But Dean, be sure to remind Sam that unlike last time, you will have your regular training schedule and won’t be able to spend the entire time with him. We’ll make some space in your days, but he should bring school work, or other things to do when you’re not available. Of course he’ll have access to the guest house television and game systems, as well.”

“Right.” Dean seems to be brightening back up quickly, future plans notwithstanding. “Now he’s presented, though, he’s been researching this stuff, plus the supernatural, pretty much all the time he’s not studying for his SATs. I mean, he’s got some theory about pheromones.”

“It’s not a theory,” Meg chuckles, “it’s science, and it sounds like it will be delightful to have Sam here again if he’s that interested in our work. And of course we’ll keep it appropriate,” she assures both Dean and Castiel, not that he’d been concerned. Meg has taught classes at their Dominant centers before, and of all of them, is probably best suited to help Sam with any questions.

Benny still has Dean tucked in the curve of his arm, and is looking at him with a little concern, but then blinks it away. Castiel knows the feeling. This is going perhaps too smoothly. Or maybe Dean is just still calm and submissive from this morning. Castiel isn’t getting any sense of suppressed distress from the boy, though he does still appear to be a little flustered or confused, beneath the excitement about Sam’s prospective visit. Maybe this is one hurdle he’s come to terms with, at least partially. If so, it will make Benny and Meg’s job much easier.

“Watersports, elimination play, in one form or another, it’s one of the most common kinks there is, all the way across the spectrum,” Benny keeps going, now that the question of Sam is temporarily answered. Dean chews on his lip, looking down at his hands, his cheeks flushing pink. “I want to be sure you have a chance to ask any questions about it, and we have a few days to talk about it, before your training starts, to make it easier for you.”

Meg nods agreement. “And we'd like to know a little bit about why you were so against it, too, so we can help with that. The boss told us how when you finally used the diaper, you had a good time. So that's great. But if you're worried or concerned about anything, you gotta talk to us about it, so we can help.”

Dean eyes her sideways, then Benny, then looks to Castiel, who nods encouragingly.

“Why?” he asks Castiel again, a little plaintively. “I...I want to understand, I guess.”

“For me, it is about control,” Castiel answers, after a moment of thought. “Much like the hand feeding. Controlling the aspects of how your body works, seeing it, managing it, handling it. Everything in and out. Not all the time, that would be too much for me, but occasionally, yes, it's something I enjoy. It's intimate, special.”

“But it's dirty,” Dean protests, like he can't resist, and Benny huffs a laugh.

“Cher, like I said, this is one of the most common kinks, to one degree or another. Maybe not everyone uses a diaper, or some of the even more exotic things the high-level Dominants and Subs tend to go for, but it's very common. We had a special pad for you, for your inspection, yeah? No mess, no smell. And that's just for free release. There are so many tools, toys, even medications, to make this easier. There is a supplement you'll start on soon to remove the urine odor safely. And our adult diapers control the mess and any smells perfectly.” He rubs Dean's belly.

Dean twists a little restlessly. “And you like it too?” he asks Meg directly. She's been the least present in his training so far, Castiel knows.

“I do,” she nods. “I enjoy the control, like the boss does, and I also enjoy the embarrassment part of it, for some submissives. Having to ask to be changed, losing bathroom autonomy.”

“You said no humiliation,” Dean instantly protests to Castiel, who smiles at him a little.

“Embarrassment, not humiliation. Humiliation makes you feel small, worthless, and yes, some Submissives and Dominants enjoy that dynamic, but I don't believe it's right for you. But I've seen you enjoy some embarrassment, which is much lighter, like a tickle instead of a punch. You're doing something that embarrasses you, yes, but we're not shaming you for it. We're telling you how much we enjoy and appreciate it.”

Dean flushes and looks away, chewing his lip. Meg grins at him, and keeps going.

“None of us think of it as dirty or disgusting, and we love watching you blush and squirm. I like using it as a way to control the access a Submissive has to any body part between their legs. They're never to touch or interact with those parts when they're with me, that's only for me to do, so a diaper is useful. And like the boss and Benny, I like age play a lot. Maybe even more than they do, though we all do it our own ways. A Submissive who is comfortable and easy in longer-term diaper wear opens up a lot of possibilities for that.”

“And you know how much I enjoy it,” Benny chimes in. Dean's looking between them, eyes wide, overwhelmed a little, pulling absently at his arm bindings, but resting back against Benny trustingly.

“So why couldn't I just say okay I'll wear one, whatever, and then, it's all good? I don't get why there's training?” Dean sounds a bit plaintive, and more than a little stubborn, and Castiel looks down to hide his smile.

“It's harder than you think to allow yourself to relax and release into a diaper. You found that out once already, your Sir told me how much help you needed,” Benny reminds him, his deep voice gentle. “There are plenty of mental and physical blocks. To stop resisting it, to tell someone right away when you need to be changed, to even learn to enjoy it, that's a process. You're not the first who me'n Meg have introduced to this. We'll use rewards to help it be fun for you, too.”

“What kind of rewards?” Dean perks up at that, as always interested in something good coming his way.

“Meg is strict with no-touching, but I let good boys touch their cocks while I'm changing wet diapers,” Benny chuckles, “and I touch them myself as a reward for messy ones.”

Dean goes still. “But I get enemas,” he says, his voice a little thin.

Benny hugs him close. “We'll stop your enemas on Thursday, cher. By Friday you'll be ready to use the diaper like a good boy. We have some mild medication to give you that will help, too.”

“No way,” Dean says, flat and serious.

“Dean,” Meg warns him, with a look at Castiel. He hands her the switch. This meeting is theirs, really, he's just here to supervise.

“No WAY, fuck that, no way, pissing is one thing, but I'm not, not that,” he says, and strains against the arm bands, much harder than before, pulling away from Benny.

“We can talk about this calmly, or Meg can deal with how disrespectful you're bein' right now,” Benny says firmly, “you've gotten a lot more warnings than I thought you'd get, after what the boss said this morning.”

“Screw you, you can't punish me, only Sir can,” Dean hisses at Meg, eyes narrow and angry, jaw clenched tight, shoving back against Benny to try to free himself, and Castiel blows his breath out between his lips, propping his chin on his hand.

“You know that is untrue,” he says, disappointed.

“Five on your hole and then we can continue this conversation,” Meg says, hard and stern, and Dean twists fiercely, but Benny flips him with practiced efficiency over his lap.

“No! It's not fair!” Dean kicks wildly and tries to push up and away, but he has no leverage, and Benny had taken him by surprise; he'd been focused on Meg, and not expecting the double-team. “You can't! Sir!” he twists to appeal to Castiel, who shakes his head.

“Don't look at me,” he tells Dean. “I'm not the one who you were disrespectful to, and I'm not the one punishing you for it.”

His face falling, Dean tries to get his knees under him to escape, but Benny was anticipating it, and has an ankle over his calves quickly.

He pins Dean's legs with a little effort. “Behave,” he growls at the squirming boy in his lap. Castiel sympathizes. No matter how Dean pushes for punishment, he never goes to it gracefully.

“NO!” Dean shrieks, and tries to rear up, but Meg is there, her hand on his lower back.

“Be still,” she commands, Dominance heavy in her voice, and though Dean doesn't submit to it entirely, he does stop his struggles and goes still, with a waiting tension all through him. “You reacted disrespectfully and rudely, in the middle of a discussion. Castiel told you this morning that there would be no tolerance for misbehavior today, and you were warned. I will switch you five times on your asshole for that rudeness.”

“I'm not sorry,” Dean snarls into Benny's jeans.

“Not yet,” she promises. Unlike Castiel, she doesn't bend the tip and snap it. She holds Dean's cheeks open with one hand, and slaps the switch down smartly with the other.

“One,” she says, as Dean heaves silently against Benny's hold.

And again, “two,” and Dean hisses through his teeth as the blow lands, but doesn't cry out. She looks at Benny, who nods, and then “three,” the next strike is sharper.

“AH AH AH!” Dean breaks, yelping, arching up, hips curling frantically down and away. “No more, no more, please Meg, I can't...” She ignores him as Benny holds him back down into place, as she pulls his clenching, shivering cheeks open again.

“Four,” just as hard as the third, and Dean wails wordlessly, voice cracking with a sob. His legs sag open, his hands grip at Benny's arm as the fight and tension drain out of him.

“I'm sorry,” he gasps, thin and wet. “I'm sorry, I'm sorry, pleeeease.”

“Five,” the hardest yet, striping down into his crack, and he shrieks and jerks and tries to crawl into Benny.

“I'm so sorry, I'm sorry, I won't, I'm sorry,” he sobs, face in Benny's belly, curved awkwardly.

“You are forgiven, little brother,” Benny says gently, warmly, petting him. “There, that is much better, yeah?”

Meg puts down the switch and slides in next to Benny, and he shifts the boy to her, and he goes easily, without a protest, letting himself be held in her arms as she strokes his back, his hips, his wet face in her shoulder.

“You did very well, Dean,” she murmurs to him. “That was good. I'm glad you're sorry, and that we can keep talking. It's over, and you're forgiven.”

Pleased with how Benny and Meg handled the whole affair, Castiel smiles at them. “He's been having a hard day,” he says sympathetically.

“That's what we're here for,” Benny answers sturdily.

“Indeed,” Castiel agrees, counting himself fortunate yet again in his staff, his friends. So many Dominant trainers of his acquaintance would never be able to leave a Sub in any stage of training with their friends or staff with confidence, and yet he has no qualms in this. In fact, it comforts him, knowing that Dean will experience new hands in such a safe and trustworthy environment, and one he's already comfortable in.

Gently, Meg pulls away so she can look into Dean's tear-streaked face. The boy looks calmer, if still a little devastated. “I know your bottom is already sore,” she tells him, gentle but no-nonsense. “I went easy with you, because of it. But we are serious when we tell you that your manners are required, Dean, do you understand?”

“Yeah, I think so,” Dean nods a little stiffly. “It's hard. Sometimes it's like I want to fight it? Or I need to? But, I don't wanna get punished.” It's plaintive, at the end.

“Is it easier, now, to relax and listen?” Benny's rumble interjects. “When I say your enemas are going to stop, but we'll help make it good for you to use the diaper?”

Dean takes a deep, shaky breath, but then nods, tentatively. “Yeah,” he answers, almost surprised. “I mean. I still...I don't...but yes.”

“Sometimes it helps to know what the boundaries are, when you're afraid or uncertain,” Castiel says, gently. “Part of you may realize that, and acting out is your way of asking for reassurance, because it's all still very new.”

Dean turns his face into Meg's neck, curling small, clinging to her. She bends to him, murmuring something Castiel can't hear, but clearly soothing and easing him, as his body gradually relaxes and opens. He watches, considering, and tips his head to Benny, who moves quietly to his side.

“Is the plan for Meg to handle some of the age play?” he asks, low enough for Dean to not overhear.

“Oui, yes,” Benny confirms, a knowing glint in his eye. “His maman died when he was just a baby, and he's had no real female authority figures, right? And she likes her littles very young indeed, and is never sexual with them at all. If it isn't working for him, of course we will adjust, but we thought it might be a benefit for him to have an Auntie as he worked through some of the early stages.”

“I think that might be a very good thing,” Castiel replies, quietly.

They watch Dean cling to Meg, and she says something to him that makes him giggle, bright and young, even as he's still holding on to her like a baby monkey. She's running gentle fingers through his hair, scratching the back of his neck where the hair is just starting to curl. His eyes are half-closed, blissful. He tilts his face up, listening, and then flushes, and nods shyly.

“Did you have attention stimulators made for Dean?” Meg raises her voice just a little, but never stops petting him.

“I did,” Castiel answers. “Custom, from Benny's internal scans. They're here in the office, actually, they arrived earlier this week.” He stands and goes to the desk, where he remembers stashing the package.

“Charlie calls hers Mister Thinky,” Meg tells Dean, and he laughs again. “They were invented by a Submissive, did you know that? He had trouble with impulse control, and attention span, and it was frustrating both his Dominant and him. So he invented these. Do you remember how slowly and carefully Charlie walked when she was here, that whole first day? And she sometimes paused to think before she spoke.”

Dean nods, watching her.

“The stimulators are a reminder. Uncomfortable, but not actively painful. Well, the small one isn't. For Charlie, it helps her get into and keep a Submissive, respectful mindset when she isn't just here for work.”

They look like shaped dildos. Castiel has had two made for Dean, a thick one and a more slender version, but both have shaped extrusions that come to blunt points, customized to prod into his Angel glands and his prostate if he moves too abruptly. The thick one is slightly roughly textured at the tips, and is rough around the slim neck below the flared external base to chafe a little at his hole. He hands them to Meg with a smile.

“You think this'll help?” Dean looks a little skeptical, but he reaches out to touch the slender one with a finger. “Keep me from getting punished so much?”

“I think it might help you stop making mistakes by accident, or because you're not paying attention,” Meg nods. “If you're acting out because you need correction, it probably won't stop you, but nothing will. And you can't wear these in a diaper, or when you're exercising, or a few other times. But they'd probably be helpful sometimes.”

Dean looks at Castiel, who tips his head.

“I've had them made for every Submissive in training who comes here,” he offers. “Every one has found them useful, some more than others. I may have you wear it, if we're going into a situation where I think your attention and manners may be tested in public, for example. But other than that, using it is up to you.”

“Okay,” Dean breathes. He looks between them again, his face hopeful. “Are we done talking about the training thing for today?”

Benny chuckles. “Not quite. But close enough, cher. I think you can make it, without the assistance, if you want.”

“Okay. Cause my butt really hurts, and I don't want anything touching it right now,” Dean confesses artlessly, and Meg laughs, and hugs him again.

“All right, I guess we'll keep this quick, then, eh?” Benny laughs. “The original plan was to start on Friday in the age play rooms, and probably Saturday too. With your brother here, we'll likely not move to the playrooms until Friday evening, which isn't perfect, but we can make do. You'll be staying with me in my quarters while Castiel is away, unless Meg decides that staying in the playrooms would be better. But other than the first few days, we'll be spending the days normally. We'll do meals, you'll train with Cole, have a massage, all the rest. Meg or I will be with you, to help you, the whole time.”

Dean's chewing his lower lip, and Castiel has to remind himself not to interrupt to go over there and make him stop.

“What if I really can't do it?” he asks, obviously worried. “What if I, I don't know, freak out, or can't do it?”

“We will be right there with you,” Meg repeats firmly. “If you're ever in distress, you know we'll fix it.”

He glances and her and nods. He's thinking now, brain really engaged, and not just reacting, Castiel is happy to notice. There’s still a slight frown on his face, a wrinkle between his brows, but his eyes are thoughtful, not afraid.

“Okay,” he finally says. “Okay, I think I gotta...think about it, and maybe have some more questions. But okay. At least my junk won't be hanging out all over.”

“That is true,” Meg tells him solemnly. “And my only argument against, since this thing,” she taps a fingernail against Dean’s cock cage, small between his thighs, “is so pretty. It really dresses up the place.”

“Meg!” Dean’s scandalized, and then laughs with her, settling easily back into her lap, though he moves gingerly.

Castiel stands to put the stimulators back on his desk, and Benny comes with him.

“You know you’ll need to tell him about the nonhumans working here, sooner rather than later.” the big man says quietly, but with an unusual amount of seriousness for him.

Castiel sighs and rubs a hand over his face, looking back at Dean curled into the lap of a demon, face trustingly against her breast, his own wings itchy where they’re hidden. “I know. It hasn’t been the right time. I’ll need to be here and have a somewhat clear schedule first. But I will.”

“Before too long?” Benny’s watching him intently, and it occurs to Castiel that Dean has friends, family here, beyond himself, and he is glad.

“Before too long,” he swears, and Benny smiles, relieved, hearing the promise in it.

Chapter Text

This time of year, Benny likes to drink his coffee walking around the grounds outside the big house, just enjoying the quiet and the early summer mornings, the peace before the hustle and bustle of the day. Wednesday dawns no differently. The two small guest houses, the detached garage, the sheds and outbuildings are quiet and still, but there’s movement in the main house; early breakfast, he knows, getting ready for Sam to arrive. He sips his coffee and wanders across the short lawn, still wet with dew.

A battered old compact with an engine that’s running, to his ear, like a brand new car turns down their long drive, tiny in the distance. He turns towards the house, but he’s in no hurry, and yep, by the time he strolls up to the steps, Dean is hugging his brother tightly by the side of the car, and the other door is just opening.

A tall, burly older man, short gray beard, wearing a trucker cap, looks over the top of the car at the brothers. Dean’s naked and Sam still has his backpack on one shoulder, but they’re talking into each other’s ears, and he’s grinning at the pair of them as he closes his door and stumps towards where Castiel has just left the door and moved to join Benny on the steps.

His eyes are some of the sharpest Benny’s ever seen, and his hand is as callused as wood, when Benny takes the extended handshake. He’s clearly a Dominant, if a low level one, but wears it as easily and comfortably as his old boots.

“Bobby Singer,” he says, gruffly. “Since the idjit didn’t see fit to introduce me.”

“I’m Benny Lafitte, one of the Dominant employees here,” he smiles at Bobby.

“Castiel Novak,” the boss says, shaking his hand in turn, and then just stands there. Benny sighs silently. Give the man a Submissive to work with, a room full of prestigious people to present to, and he never falters. But his regular everyday social skills are sometimes pretty bad. He just kind of goes awkward, sometimes.

“Heard about you,” Bobby nods, “from John, and Sam. Heard a lot about this place, too. Gotta thank you for what you’re doing for the boy.” He turns to look at Sam and Dean, who’ve progressed to wrestling for something, though at least they’re still standing up.

“It’s really our pleasure,” Castiel says, some of the stiffness easing. “Dean speaks fondly of you, too, and his work at the garage. And it’s good to meet more of Dean’s family.”

Bobby huffs a little, but looks pleased. “John wanted to bring Sam himself, but had to leave early. It was no trouble.”

“I’m surprised he didn’t come, at least to see the house, before letting Sam stay overnight,” Castiel muses, and Bobby laughs, surprising both of them.

“I mebbe shouldn’t be telling you this, but Sam says you’re in the know about the life, so I suppose it’s okay. John’s been here, and seen the place, at least twice.”

Benny’s jaw drops in shock, there’s never been a hint of anything on any security systems, and he can feel Castiel drawing up, his face getting thunderous.

“Don’t get tempered about it,” Bobby continues, waving his hand. “If you know hunting, you gotta know John Winchester would never let his most precious chick stay anywhere without confirming for himself the place and the people were safe. And the fact he’s letting Sam stay here too? Both his boys under one roof, without any of us there? Well, I can say it speaks real highly of you all.” He grins at both of them, clearly enjoying their discomfiture.

“Bobby!” Dean’s shout interrupts; he’s finally torn himself away from Sam, it seems, and runs towards them, something clutched in his hand. But Sam catches him from behind and tackles him hard, and they both go down.

“I, ah,” Bobby clears his throat, suddenly losing his grin and staring out towards the lawn intently. “I was real worried about him before he came here. And he looks fine. More than fine. Better’n I’ve ever seen him, maybe.”

Castiel nods stiffly. Maybe not quite over the revelation about the unknown home invasion, but the naked emotion on Bobby’s face is impossible to resist.

“He’s a lot healthier,” he says gently. “Still himself, but getting more comfortable with who he is every day. Last time, he insisted on getting dressed before coming out to meet Sam. This time he just shrugged it off, since he knows he’ll take them off in the house anyway.”

“Bobby,” Dean tries again, breathless with laughter, he’s made it back to his feet. Sam’s reclaimed whatever it was he’d stolen, and he’s let Dean go, and they’re walking towards the house. Benny tries to see him with new eyes, imagining Bobby’s perspective. Dean’s gained back all his lost weight and more. He’s put on pounds of muscle, and his bearing is straight and confident, he’s smiling and bright, his eyes clear. He’s sleek and hairless, the silver cock cage glinting discreetly between his thighs. He moves differently now, a little, a sway to his hips, his back a tiny bit arched as he moves, his chest proud and shoulders back, all the positioning work paying off, and perhaps his own sexuality showing through as well.

“Boy,” Bobby says gruffly, but his eyes are shining. “You look real good, Dean.”

“Missed you,” Dean blurts, and then throws himself forward for a hug, which Bobby crushes him into without hesitation.

Benny finishes his coffee and nods to Castiel, heading into the house, leaving the Winchesters and Singers to their reunion. Bobby will probably get a tour of the house, he knows, and Dean will talk his ear off. Benny has a list as long as his arm to get through today, and the day’s just beginning.

***

With the last onesie folded and stacked, he marks the last item off his prep list for the age play room, and just in time, too, as Meg comes through the door.

“Nice,” she compliments, looking around.

The furniture has been rearranged somewhat to accommodate a longer-term stay, with more free space on the floor, and an additional large armchair, with big plush padded arms brought in. The supply shelf is stacked high with diapers, wipes, and cloths, the medicine cabinet is full with everything they’ll need, and the fridge is full of food for both them and Dean. The bedroom’s been set up with a crib, and the bed made up.

“I think I got everything,” he nods, smiling at her. “Even some extra toys and books. And I brought my bag like you asked,” he lifts it from the chair, showing her.

“Great.” She starts unbuttoning her blouse, sitting up on the changing table without a second’s hesitation.

“You’re really going to take him down small, hmm?” He gets the needle and bottle of medication, and starts drawing the injection out, as she removes her bra. She nods.

“Have you ever nursed a Submissive?” She watches him tap air bubbles out of the needle, and he shakes his head.

“I’ve brought in milk IN submissives, and fed from them, obviously not in this context. The bond is incredible. Powerful and primal,” he notes, taking one of her breasts in hand and feeling for the correct spot.

“It’s like that, only reversed,” she says, and bites her lip at the pinch of the injection. “Like handfeeding, only...more. Feeding them directly from your body, providing like that, it’s hard to even explain. And for the Submissive, it gives the most incredible feeling of calm, peace, protection.” She watches him swab the site with iodine. “You could nurse him too, you know.” Her eyes glint teasingly up at him as he moves to the other side. “You’re far more nurturing than I am, anyway, and you’ve been calling him Little Brother for over a month now. If you did, we could keep him on the breast and the bottle for the whole time he’s little.”

“I’ve heard it’s a real bitch when the milk comes in, for Dominant men,” he says, but the idea of it’s taking hold. He taps the hormone and limiter cocktail again in the syringe, making sure the second dose is correct, and injects her second breast carefully.

“Worth it,” she claims absolutely.

“Think it’d help?” He discards the used needle, but doesn’t put the bottle away.

“I think knowing he can trust us and depend on us for everything will help,” she says firmly. “That he’ll need to ask for help, but that he’ll get it, he will learn that quickly, in that physical way Castiel described him needing. And a liquid diet will absolutely make the diapers a necessity. And the bonding and closeness? Definitely.”

He rubs at his own chest absently, consideringly. The injection lasts about a week, he knows. It will take a day or two for milk to come in, and when it does, it’ll be perfectly normal human breastmilk. Though all men CAN lactate, he knows most Dominant men don’t ever bother, because it’s a hassle, and can get uncomfortable. But he’s admittedly curious, and knows it does suit his particular style of Dominance well.

She’s done re-dressing by the time he makes up his mind, and starts preparing another shot.

“Awesome,” she grins at him. “This is gonna be great. And so good for him, too.”

“I wouldn’t do it, otherwise,” he admits. “If he doesn’t take to it, we’re in for some uncomfortable days of pumping.”

“He’ll take to it,” she says confidently, and so far, she’s been pretty spot on in her readings of Dean, so he nods, and goes ahead with it.

***

They all show up for lunch, except Dean, which Benny thinks is a little odd. Sam looks pretty much just like he remembers him, except maybe even a little taller, and his voice has fully changed, deeper now, so when he answers Castiel’s question it’s almost a rumble.

“He said he wanted to show me something about twenty minutes ago, and went off to get it, and I haven’t seen him since. We were playing pool.” Sam shrugs helplessly. “I don’t know where he is.”

Castiel frowns a little, then stands and goes to the intercom. Being late to meals is, Benny knows, one of his pet peeves. He finds it disrespectful of the effort Angelique puts in to make them all delicious food. “Dean, come to the lunch room. You have five minutes, or there will be consequences,” he says sternly into the intercom, and then sits back down.

“How are you liking the training classes so far?” Meg asks Sam, and Sam brightens up right away.

“I’ve only been to two, so far? But they’re amazing. So much better than what we get in school. I wish everyone could go. We got sorted into groups depending on our tests, Doms and Subs together, and it’s so cool, we’re mostly doing reading right now, but we’ve seen some demonstrations and stuff. The teachers are amazing.” Benny grins at his gushing. “We’re learning how to recognize the nonverbal cues from a Submissive right now, just the basics. And the Subs are learning to read our body language. I didn’t even know my body was saying so much stuff!” He sounds incredulous, and Meg laughs, not meanly, but in enjoyment.

“It’s pretty incredible,” she agrees. “Who’s your main instructor?”

“For the Dominants, Dominant Mosely? She’s just, wow,” Sam says, with stars in his eyes.

“She’s one of our most experienced instructors,” Castiel puts in, pleased, Benny can tell. “I’ve worked with her myself, and she’s one of the best.”

“She’s so intuitive, she can tell when anyone in the class needs more help, or isn’t getting something,” Sam enthuses. “She does it all just really...effortlessly, I dunno, it’s amazing. She says what we’re learning is reinforcing our instincts and making sure they’re all pointing us in the right direction and that our brains and bodies are all working together in good healthy ways. It totally makes sense, the way she puts it, I understand it completely.”

Benny shares an amused glance with Castiel. He vaguely remembers being a brand-new baby Dominant. The rush of instinct, the confusing imperatives from his impulses, the conviction that after a little learning he knew pretty much all there was to know. Sam’s adorable with it, though, all enthusiasm and big broad gestures with his hands, and almost gets Benny in the face once or twice, since they’re sitting next to each other.

He’s describing one of the books they’re reading for class when Dean hurries through the door, flustered and red-faced, and everyone goes quiet. Castiel looks at the clock, and then back at Dean.

“Almost seven minutes,” he says quietly.

“Someone moved my pack again, I couldn’t find it!” Dean protests, looking accusingly at Benny, Meg, Cole.

“What’s the rule about meals?” Castiel stands, and Dean huffs an aggrieved breath, but starts to look guilty.

“We’re on time to show respect to Angelique and her hard work,” he mutters, and shuffles his feet a little.

“The switch, if you please. And put yourself on the bench.” Castiel’s Dominant voice is steel and velvet.

“Sir!” Dean gasps, jerking to look at Sam, then at him again, eyes wide. “I lost track... I thought I could make it…”

“You were already late when I gave you five minutes. If you’d left then, you could have made it here at a slow walk from anywhere in the house. The switch. Now, Dean.”

Benny glances at Sam. He doesn’t look embarrassed, or angry. A little concerned, maybe, but more interested than anything, just watching. Benny doesn’t think Dean earned punishment while Sam was visiting last time, so this will be his first time seeing this. Honestly, Benny’s a little mad at Dean too, right now. He’s starving, and this is another delay for getting to start eating.

Dean fetches the switch with obvious reluctance and drags his feet getting to the bench, and Castiel follows him silently.

“Bend over,” he says crisply, and Dean does, still reluctantly. He clearly knows he’s earned it, though, there are no protests. “Six on your bottom, two on your anus, Dean. Lateness to meals is absolutely unacceptable, unless there’s a conflict or emergency. Spread your cheeks.”

“Yessir,” Dean acknowledges, already half a sob under the word as he reaches behind to hold himself open for punishment.

Dean’s squeal and kick and thrash at the first snap on his hole clearly startles Sam, who jumps almost as much as Dean. Benny leans towards him.

“You okay?” he asks. Sam is watching, still with that little line between his brows.

“Two,” Castiel says sternly, there’s a second snap, and Dean cries out again, this time with words, his apologies thick with tears.

“Yeah,” Sam answers, after a moment, sounding surprised. “I was thinking it would be hard. He’s hurting Dean, right? Even though I know it’s a good thing in my head, I thought it’d be hard to see. But it isn’t.” He’s sounding a little baffled, now.

Dean’s sobbing, as the switching continues on his upraised ass, hard enough to leave marks. He screams a little as each blow lands, twisting and kicking.

“Feels right and proper?” Meg suggests gently, from his other side, and Sam tilts his head in a nod.

“And I can tell Dean’s okay. Like. I don’t know how?” He shakes his shaggy head. “He sounds like it hurts so bad, how do I know he’s okay?”

“A lot of ways,” Benny comforts him. “All those nonverbal cues and instincts are working, now. He’s in a dynamic that’s working properly. He’s not in distress, even if he’s in pain; if he was, you would sense it. He’s being corrected appropriately for bad behavior. He’s responding the right way. All of that tells your subconscious that he’s fine, he’s better than fine.”

Sam’s face clears, and he nods, with a small smile at Benny.

“I’m sorry, so sorry Sir,” Dean sobs, as Castiel puts the switch away, finished.

“I know, and you are forgiven, it’s over and done,” the boss says, warm and fond, lifting him off the bench and into his arms. “Please go ahead and eat, we’ll be a moment,” he tells the table, and slides into a chair with Dean in his lap, held closely in his arms. “That’s my good boy,” they can hear him say to Dean. “You won’t be late again, hmm?”

“No Sir, I won’t, promise, promise,” Dean sniffs, face in his shoulder.

Benny, relieved, piles his plate with food, and passes the potatoes to Sam.

When Dean and Castiel join them at the table, Dean’s place is set, and Castiel guides him to the chair beside his own. He pauses before sitting down, his face going pale.

“Be seated, Dean,” Castiel’s voice brooks no argument, and Dean sits, gingerly, biting his lip and wincing as he makes contact. He still hasn’t looked directly at Sam, but his eyes are clear, and he isn’t hiding or ashamed that Benny can see.

“Rump roast for lunch, huh Dean?” Sam says, out of the blue, and Meg almost chokes on her tea.

“Sam!” Dean’s scandalized voice is almost drowned out by Benny’s guffaw.

“Oh dear,” Castiel sighs, but the corners of his lips are twitching.

***

The most tedious part of Benny’s job is definitely the paperwork. He updates the clinic records for the house, inventories all the medications, puts in orders for anything needed, and updates a few files, noting the injections for himself and Meg on their own records. In addition to taking care of Dean while Castiel is away, he and Meg will be responsible for the rest of the operation, and he wants to be sure everything is squared away in the clinic to free him up.

By the time he’s done and making his way to Security to check in with Cole--the poor guy kind of lost it when he found out John Winchester’s been in the house twice and nobody had noticed, and has been going through security footage all day--it’s late afternoon, and Castiel calls his name as he’s passing the study.

“Yeah, boss?” He sticks his head in. Dean is kneeling in his regular place on a pillow by Castiel, and Sam is on the couch with books and papers spread on the coffee table. Everything looks pretty calm, though Dean’s cheeks are pink.

“Can you spare a moment?”

“Sure.” He’s curious, and in no rush.

“Dean and I will be working on some sexual submission for the next hour,” he says, straightforward, and Dean blushes harder, “so if you could take Sam to the library, or to your rooms, Sam, if you’d prefer that, it would be much appreciated.”

Benny grins at Dean’s scarlet face, and nods. “Of course. You need help with all that?” he asks Sam, who’s bundling up his papers.

“Nah, I got it, thanks,” Sam says distractedly, mind obviously still caught up in whatever he’s studying. “See you at dinner, Dean,” he waves as he follows Benny out.

“I know they’re having sex,” he says, a little impatiently, at Benny’s raised eyebrow as they make it into the corridor. “Just because there wasn’t a dynamic relationship in my house growing up, doesn’t mean I don’t get how it works, like, at all.”

“Hopefully you aren’t learning the ins and outs from watching porn,” Benny mutters, and Sam snorts.

“That stuff never looks real. I mean, not that I’ve seen any!” he hastily adds, and Benny grins again.

“Of course not. Your stuff is in the downstairs guest room, right?” Soundproofed and far from the main goings-on in the house.

“Yeah. It’s really nice,” Sam enthuses. “I’ve never slept in a bed that big! And there’s a TV right in the room! And my own bathroom!”

“We want you to be comfortable,” Benny tells him, and opens the door to the library.

“The real question is, are the rest of you having sex with Dean?” Sam asks, setting his papers down on one of the desks and turning to look at Benny.

“That, my boy, is absolutely none of your business,” Benny informs him calmly. “But the boss did ask me to tell you about Friday, and this seems like a good time. He’s heading out of town, and leaving Meg and myself in charge of the house.”

Sam sits in the big chair, and listens intently as Benny gives him the bare bones of what will be going on, the training, the schedule. “And we’ve changed our plans a little to account for you being here, but we expect Friday will be a little challenging for Dean. Hopefully, everything will go smoothly. But if not, I’ll expect you to listen and respect me and Meg just like you would Castiel.”

Sam nods, big-eyed.

“He’s got a good brother in you, Sam,” Benny tells him sincerely, and for the first time, sees Sam lose some of his unnaturally mature composure, flushing and looking down, his mop of hair falling over his eyes.

“I owe him a lot,” he mumbles. “He’s not just my brother, you know? He’s my best friend, too. Least I can do is be supportive.”

“You’re doing a great job,” Benny assures him, fondness welling up for the Winchester brothers.

“You guys, too,” Sam says, just as sincere, smiling. “Dean’s awesome. He’s so happy, now. Like, I’d forgotten what that was like, but he’s...normal again. Like I remember when I was younger, only now it’s even more, cause I can tell he’s a happy Submissive, too. Mostly.”

“Mostly,” Benny agrees, with a laugh. “And that’s those instincts again. When a Sub, especially one we are close to and care for, is in distress, unhappy, unfulfilled, a Dominant can tell. And we are driven to fix it, to make it better, yeah? Unless there’s something wrong with the Dominant, or they're just an asshole, we’ve gotta try to make it better, protect and care for the Sub, try to get things back to balance and under control.”

“That must have been hard for you all, when Dean first got here,” Sam muses, head cocked. Benny smiles a little.

“It’s our job, it’s part of what we do, so we’re used to managing that kind of input. But I’m glad Dean came before you presented. It would’ve been real hard on you, for sure, since he was in a lot of distress when he got here.”

“And he’s not now,” Sam says, definitively. “Which is so great.”

Benny claps him on the shoulder. “Well, I’m glad we have the brother stamp of approval. That means a lot. The security office is right down the hall, three doors on the left, and I’ll be in there if you need anything, okay?”

“Okay,” Sam says, and looks around the library, the walls of books, with a happy sigh. “I don’t think I will. Can you come get me so I’m definitely not late for dinner?”

“I absolutely will,” Benny promises him.

***

No one’s late to dinner, which is a good thing, because Benny’s starving again, and his chest is starting to hurt. Mostly he wants to get everything over with and go home to his quarters, attached to the main house, and put heating packs on his pectorals, but it’s fun watching Sam and Dean talk to each other, easy and animated, catching up, names and jokes and teasing flying back and forth.

It feels like family, he finds himself thinking. He really hopes this thing with Castiel works out, with Dean. They’ve had many Submissives in training here before, but none who’ve worked themselves into the fabric of the house, their lives, the way Dean has, and the way even his little family has. He finds himself smiling affectionately at the pair of them, sitting back in his chair, finished with his meal, just enjoying the togetherness.

“I’ll miss this when I’m away,” Castiel murmurs beside him.

“It’s nice,” Benny agrees, and then winces and shifts his shoulders.

“Meg convinced you,” Castiel notes, humor in his voice as he looks sideways at him.

“She did,” Benny admits. “It sounded great at the time, and I probably won’t regret it, but right now, it’s no fun.”

“I’ve never felt the urge. It wouldn’t suit me in the least,” Castiel admits, candidly. “But I can definitely understand her point, and yours, and see the dimension it would add to the play. I’m looking forward to hearing all about it.”

“We’re all set up to go,” Benny says, pleased. “I let Sam know, too, and he’s unworried.”

“Huh?” Sam, hearing his name, turns to them.

“Nothing important,” Castiel smiles at him and Dean. “Go, enjoy your free time. Try not to bring the house down around our ears. Just be sure to take Sam to his room before it’s time to see Benny.”

“Yessir,” Dean agrees quickly, and stands up gingerly. Obviously the sex session had been intense, and Benny notices he’s still wearing the cock cage. Laughing and shoving, the two tumble out of the dining room, their voices audible for long moments after they’re gone.

“I was gonna ask, boss, think I could tap out of his enema tonight? Have you do it instead? I’d like to get flat with some hot packs and some ibuprofen, if that’s all right,” he winces a little again. It’s not awful, but it’s definitely strange and uncomfortable, and he’d rather not work with any of the Subs while distracted and out of sorts like this.

“Of course,” Castiel says immediately, sympathetic. “I’m sorry I haven’t stayed more in touch with what’s going on with you, but do you have someone you’re seeing right now? A Submissive who could assist?”

“Not at the moment,” Benny admits ruefully. “I’m pretty busy here, lately, and honestly, all my needs are met with the practice I get in with the staff. But I’m all set, I can take care of it.”

“If you’re sure,” Castiel frowns a little, and Benny chuckles.

“Absolutely sure. Thanks for asking, though, Boss. And good luck with those two tonight.”

“They make me feel old,” Castiel complains, and Benny nods.

“Yeah, me too.” He stands and stretches, carefully. “Anything special on the docket for tomorrow?”

“No...Sam will be doing an informal class with Meg while I’m intimate with Dean, but other than that, he’ll be joining Dean’s run and workout, and the rest of the day should be normal. Ash is still in Houston,” he thinks for a moment. “That’s all.”

“All right. Then I’ll see you tomorrow.” Castiel sends him off with a smile.

As he makes his way through the grass again, now cool with evening, Benny has to stop and appreciate his life for a minute. Sure, it’s pretty far outside of ‘normal,’ but he wouldn’t change it for the world.

Chapter Text

Sir wakes Dean up much earlier than usual, the sky still dark outside the bedroom windows, with a hand on his shoulder and saying his name quietly. For once, Dean wakes up right away, the knowledge of what today is sparking into his mind, driving a little rush of adrenaline and nerves right through him.

“Leaving soon?” His voice is still rough with sleep, even as he rolls out of bed and stretches a little.

“The car will be here in a few minutes,” Sir confirms, turning on one of the room lights, smiling at him. He’s showered and dressed, and the bags that were packed by the door last night are nowhere to be seen. “I wanted a chance to say goodbye properly, so let’s have you go use the potty and brush your teeth.”

Dean nods sleepily, and pads after him to the bathroom. Sir actually puts him onto the toilet, and tucks his penis down, and holds it while he pees, running soft fingers through his hair the whole time. It feels soft and warm and caring, somehow, and Dean hums when he’s done, and Sir shakes his cock a little, then stands him up and cleans him gently with one of the wipes.

When he’s done brushing his teeth and splashing some water on his face, he feels a little more awake, and Sir brings him right out to the big chair, and tugs Dean into his lap.

“Gonna miss me, huh?” Dean teases a little, shifting to ease the pressure on his bottom. Sir had fucked him for a long, long time last night, and he can still feel it, like an ache.

“Absolutely,” Sir smiles at him, a hand playing with one of his boobs, the other one just holding his cock, which chubs up a little at the attention. “My pretty boy, my very good Submissive. You’re going to remember your rules and be good for Benny and Meg while I’m gone?”

“Yessir,” Dean nods, seriously.

“And not get into trouble with Sam?”

“I’ll try?” Dean hazards. That’s a little harder. Having Sam around is just really fun and distracting, and there are so many potentially fun and interesting things to do with him.

“Keep Wednesday night in mind, and try hard,” Castiel suggests, pointedly, and Dean winces, remembering. He had Sam had started a fire--a really, really small fire! They’d put it out almost immediately!--in one of the outbuildings, testing out one of the anti-vampire concoctions Sam had discovered in one of Bobby’s old journals. Dean had gotten fifteen hard switchings on his bottom, but Sam had not. When Dean had protested wildly at the unfairness of this, Sir had told him that corporal punishment didn’t work for Dominants, just made them angry and resentful, and told him to look at Sam. Sam was getting what looked like a really stern talking-to from Cole and Benny. Dean heard words like “responsible” and “trust” and “amends” in there. He was actually squirming where he stood, and there were real tears in his eyes, and it went on a lot longer than Dean’s whipping did. And then Sam had to file security footage with Cole all the next morning and miss out on his class with Meg.

So Dean guesses he and Sam will try pretty hard.

“Yessir,” he answers, pushing his face into Sir’s neck, breathing in his warm, spicy smell.

“That’s my good boy,” Sir hums, and holds him close for a long moment. “I’ll be checking in every evening, to find out how things are going. I have no doubt everything will be fine. Now let’s do your paddles, and I’ll get going.”

Dean sighs and nods, and stands up, fetching his paddle and bringing it to Sir, putting himself into place on the spanking bench. He says the ritual words, and Sir strokes warm hands over his back and butt and shoulders.

“You’re beautiful, Dean,” Sir tells him, his Dom voice all rich and honey-sweet in Dean’s ears, and he squirms with pleasure. “I’m so pleased when you submit yourself like this. One.” The paddle smacks into Dean’s bottom and then holds in place, sealing in the sting, and Dean feels the wave of it rock through him.

By the time the paddling is done, he feels peaceful and clean, only a few tears on his eyelashes, not even from pain, but from the feelings he always gets. And the hugs and petting from Sir afterwards are the best, too. Then Sir cups his cheeks in both hands and smiles at him, and kisses him one, two, three times on the mouth.

“So good, Dean. I’ve got to go. Benny will be up soon to get you ready for the day, and I know you’ll make me proud. You remember telling me how the hard things make you feel the best when you accomplish them?”

Feeling a little shy, Dean nods.

“Keep that in mind, for me, if you can.” Castiel kisses him again, this one long and lingering, and then steps away. “I’ll see you soon, sweetheart.”

“Bye, Sir,” Dean says, around a weird pang in his chest, a strange lump in his throat. God. He’s gonna be back in five days. Dean’s done stakeouts longer than that, this is no big deal, right? But he watches Sir go out the bedroom door and then climbs right back into the bed, and pulls the covers up over his head, and tries to sort out why he’s feeling so wobbly and sad.

Benny just lifts the covers right off his face maybe half an hour later, and smiles down at him, his nice big smile, and it already makes Dean feel a little better. He’s not alone, or anything.

“Morning, Benny,” he says, looking up from the bed.

“Morning, little brother,” Benny says, and offers him a hand, and he takes it, climbing out of his warm nest with a sigh. God, someday maybe he’ll get to sleep in again. As soon as he’s standing up, Benny flips the covers back down, though, and then opens up the bag he’s got at his feet, and puts another blanket over the top, and gets it smooth. Then starts putting stuff next to it. Some powder, some wet wipes. A diaper. Dean chews his lower lip, feeling himself go tense all over. It was all just academic till just now. Now it’s right there in front of his face.

“Up on the bed, cher,” Benny says kindly, firmly. Dean looks around the bedroom a little wildly, but then he takes a deep breath. Hard things, he reminds himself, and his sub brain, which is in some strange half-scared half-excited state, and climbs up on legs that only shake a little. “Good boy,” Benny praises him, and it feels really good to hear it, even for just a small thing like this.

“The house isn’t even awake yet,” Benny continues talking to him quietly as he stands close, moving his legs, pushing his knees up, opening the diaper, all as calmly as if this was an everyday thing. It helps Dean take a deep breath. “Pretty early for us, huh? I had to open the gate for the car, but after we’re done here, you an’ me, we can go raid the kitchen, get some coffee and some pastries. I already okayed it with Angelique.” He grins at Dean, who smiles tentatively back.

“Did she make the cherry ones?” Those are his absolute favorites.

“I believe she did,” Benny nods. He gently removes Dean’s cock cage, and the cool air feels strange on him; he’s been wearing the cage for days now, and being without it feels odd and super-naked. Benny’s big hands are warm and gentle as he wipes Dean down, then puts that silky powder on him everywhere, making him lift up his hips.

“I don’t gotta wear the cage?” he asks, curious.

“Not in the diaper,” Benny confirms. “It can hold too much moisture, cause chafing. Now pull up your knees for me, Dean, open up.” He pushes at the back of Dean’s thighs, lifting his feet off the bed, and Dean obediently holds his knees. Benny rattles a bottle somewhere he can’t see, and then there’s a cool slick hard thing pushing at his hole, and he flinches his knees down.

“Up,” Benny says sternly, and startled, Dean pulls them back up.

“What’s that?”

“You’ve been getting enemas for a long time, and this is medicine that’ll help your insides remember what their job is,” Benny explains, and Dean would snap his knees closed but Benny has already pushed it in, and his finger with it, deep and firm in one move, and he squeals softly at the burn on his sore hole.

“Looks like the boss gave you something to remember him by?” Benny teases gently, and pets his thigh gently, distractingly, as his finger works deeper, and Dean’s trying to catch his breath but the memory of last night, the way Sir helped him fly so high, makes him hot all over, and he nods. “That’s real nice, sugar. Okay, that’s far enough. That’s real good.” The finger withdraws, and Dean sucks in a deep breath, blinking at the ceiling.

“Almost done. Just the diaper now,” Benny assures him, and Dean narrows his eyes at him. Like that isn’t the worst part? But Benny puts it on him quickly and efficiently, adjusting it carefully around his legs, snugging it tight around his waist, making sure it fits. This one is dark green, he notices, looking down. He guesses that’s better than white.

“Okay,” he breathes, as Benny lets his hips down. He stretches his legs out experimentally. It’s not too bad.

“Good boy,” Benny says, in his Dom voice, and Dean preens a little despite himself. “Do you want to wear a dress today? Meg and I agreed that it’s fine if you’d rather, while Sam is here, until we move to the age play room tonight.”

“Yes please Benny,” Dean says, relieved. He hasn’t worn any of his girl clothes in front of Sam yet, but it’s infinitely better than wearing nothing but a diaper.

“Okay. Up you go, pick one out and get dressed, and then we have a kitchen to raid,” Benny pats his knee, and Dean rolls back off the bed, feeling awkward with the extra padding between his legs, like usual.

He repacks the bag as Dean picks out the plainest dress he has, the gray one that comes down to his knees with the big swirly skirt, and pulls it on. He looks at himself in the mirror critically, and turns sideways, and no, he can’t see the diaper at all.

“You look great, Dean,” Benny assures him, from the door, and Dean blows a breath out through his lips. He feels too-warm, constrained between his legs, all wrapped up like this, but he thinks he can walk normally with effort, and he digs up a smile for Benny as he follows him to the kitchen.

The cherry pastries are tucked away in the huge fridge, and Dean unearths them as Benny makes a pot of coffee. It all feels kind of secret and weird, being in the dark quiet kitchen like this, the rest of the house asleep around them, both of them talking in quiet voices as if someone might hear them. He sets out the pastries and Benny brings two steaming mugs of coffee to the table, and then sets a kneeling pillow next to his chair, and Dean has a sudden flash of missing Sir, so hard that it stops him in his tracks.

That’s when the first deep grumble from his lower belly hits, and his hand flies to it, shocked. He gets a sudden urge to run to the bathroom.

“That’s the medicine working,” Benny tells him, watching him, sitting in the chair and taking his other hand, tugging him close.

“I gotta go,” Dean says, a little frantic, suddenly, but Benny just reels him in till he’s standing between his thighs, and Benny holds him, hands soothing his sides, his belly.

“I made sure we’d be all by ourselves this time,” he rumbles, deep Dominant voice all fuzzy and comforting. Dean sways towards him involuntarily. “I know it’s hard, cher. I’m here for you. If you let go, I’ll make it easy and good for you, I promise.”

Dean trusts Benny, he does, and the pressure is building in his gut. It rumbles again, ominously. It’s hurting a little, too. And he wants his cherry pastries, and the coffee. More than that, suddenly, he wants this over with, while nobody’s around. He blinks hard--why are his eyes wet?--and nods stiffly, and Benny’s eyes crinkle with his pleased, proud smile.

“Good boy. I’m real proud of you, Dean. Here, lean on my shoulders a little, bend over just a bit, that’s right. Take a few big deep breaths for me and just relax.”

You relax,” Dean grumps into his shoulder, but he’s breathing deep, and feels Benny chuckle. Then there’s a hand rubbing and pressing at the front of the diaper, and oh geez, that feels good. There hasn’t been any direct contact on his cock in so long. Even as he consciously tries to unclench, relax, let go, contrary to every single instinct he has, his hips twitch a little, pushing into that sweet friction.

“There you go,” Benny croons, right by his ear. Another cramp comes and he grits his teeth and screws his eyes shut and pushes and oh god, oh fuck, he’d forgotten how good it feels to have the urge and just GO. It feels amazing, and the hand rubbing over his dick makes it a thousand times better, even, distracting enough that he can pretend he’s sitting on the can like normal, even though he can feel it, the weight and soft heat, filling the diaper and against his skin. He gasps a little and pushes again and it feels just as good, and he’s glad Benny’s holding him because his knees are super-shaky.

“So good, that’s wonderful. Amazing, Dean, what a good, good, perfect boy,” Benny’s praising him, just a constant stream of good things right into his mind, and his sub brain feels like it’s dizzy with pleasure and embarrassment. Some part of him realizes that Benny was right, he can’t smell anything at all, and he breathes out a shaky little huff of relief, and realizes too that he’s almost entirely in Benny’s lap, now, being held, and he’s not really sure how that happened but he’s more than okay with it.

“Are you all done?” Benny asks him gently, and Dean nods against his shoulder. He feels empty and cleaned out and so relieved.

“Good, that was beautiful. Feel how much I liked it.” He moves Dean’s hand to his own lap, and Dean can feel his hard-on, rock hard, not as long as Sir but thicker, maybe, bulging in his pants. It’s a little dizzying knowing he made that happen. “I’m so pleased with you. What a good Sub. Let’s get you changed, cher, gently now.”

Maybe Benny can read minds, because he eases Dean down right there, doesn’t expect him to walk or anything. The blanket comes back out and goes under his hips, his dress tucked up out of the way.

“Is that a diaper bag?” He suddenly realizes, and Benny chuckles, kneeling between his knees, carefully unfastening the used diaper. The cool air hits him after the humid closeness and he shivers a little, and Benny pets his hard cock, stroking it firmly.

“It is. And good boys get a big reward for using their diaper so well the first time. Let me get you cleaned up and you can come.” Dean’s old diaper is carefully folded, and then Benny cleans him thoroughly, getting into every little crevice with the wipes, which feel soft like they have lotion or something. Then a new one slides under his lifted hips, and Benny starts jacking him for real.

“Oh, oh oh oh,” Dean jerks his legs, hips arching, chasing that hand. “Oh god, Benny, so good…” the hand on him is like fire, he’s achingly, painfully hard. He’s been hard, he realizes faintly, since maybe a while back. “Not supposed to, without something in me,” he gasps out plaintively, but Benny shakes his head.

“All those rules are suspended in diapers, cher. You come whenever you want.” He twists his wrist and rubs his palm over the head of Dean’s cock and Dean’s coming, hard and long, hips jerking up and up and up as Benny works his cock through it. When he finally rides the last aftershock, hot deep pleasure rippling through his belly, Benny’s smiling at him and cleaning his own jizz off his belly with another wipe.

“And that’s how I reward good boys and girls who don’t fight their diapers,” he says, simply, and Dean nods dumbly, blinking up at him. He gets the fresh diaper onto Dean without fuss, and then eases him up, helping him to the kneeling pillow.

Dean kind of wants to complain about not sitting at the table, but he’s wrung out and turned around and still sparking and fizzing with little aftershocks of orgasmic pleasure, and it feels like a lot of work, so he kneels with a little sigh, and lets Benny feed him delicious pastries and fresh coffee. By the time they hear the house stirring awake around them, he’s feeling almost back to normal.

***

Sam looks at him curiously a few times during breakfast, but maybe that’s because he doesn’t eat as much as usual, or that’s what he tells himself, at least. Benny’d said the other day that Sam knew what was going on today, but there’s knowing, and then there’s knowing, and anyway, mostly today is supposed to be business as usual, right? So it’s a little weird when instead of going right with Cole to run after breakfast Meg and Benny pull him and Sam into the big sitting room and sit them down.

“Don’t worry, you’ll be meeting Cole shortly,” Benny assures Dean, who sighs in relief. He really needs to run today, it feels like, he’s all tense in his skin. “We just want to lay down a few ground rules for the day, before we get started.” Meg’s sitting beside him, and she’s in workout clothes too.

“Sam, you know Dean is wearing diapers today,” Meg tells him bluntly, and Dean’s mind goes a little fuzzy. He sees Sam nod with his serious face on, but he starts feeling angry, too. They don’t need to tell Sam this stuff. He doesn’t need to know! “So we’re going to need a little more privacy than usual, from time to time. I know it’s your last day here, so we’re going to try to balance that and give you as much time together as possible. And we’re trusting Dean that he won’t try to use the bathroom when we’re not there.” She grins at Dean, like he doesn’t want to rip her head off right now. He just glares back, and she has the balls to wink at him.

“That sounds good, anything I can do to help, I just wanna spend time with Dean,” Sam says, all eager, and what the hell does he know? He’s not in training, he doesn’t know anything, he’s barely even presented, Dean seethes to himself.

“Thank you, petit,” Benny says solemnly. “We appreciate it. Meg’s gonna run with you this morning, and then I think Cole has to skip Krav Maga, so you’ll have some free time together, but we’ll be real close by, and we’ll be checking in all the time. If we ask you to give us a minute with him, I want you to just step out of the room, and we’ll call you back in when we’re done. After lunch Dean has training with me, and you’re with Meg, and then we’ll give you more time together. You’ll need to say goodbye tonight after dinner, since your Uncle Bobby is coming tomorrow morning early to get you, and Dean will be in full-time training then.”

“Okay,” Sam says, looking at Dean like he’s happy. “That’s a ton of time, Dean. We can go over those protection sigils again. And I still haven’t got that card trick down yet.”

Taking a deep breath, Dean stuffs his anger down hard and deep. None of this is Sam’s fault at all.

“Yeah, you’re right,” he agrees. “And if I beat your time at the five mile, you gotta draw out the Wedjat sigil till you get it right, this time.”

Sam scowls. “I always mess up the curvy flippy ones,” he complains.

“That’s why you gotta practice,” Dean says smugly, and settles his dress more smoothly over his thighs.

“You lot ready?” Cole sticks his head in the door. “I’m blaming you for all of this,” he tells Benny directly, like an aside. “Sam asks me questions while we’re running.”

Dean bursts into helpless laughter at that. Dad had always hated that, too, but not even long-distance running can keep Sammy’s curiosity contained.

“It’s a cross you gotta bear, man,” Benny tells him, and sends them out the door. Dean’s not looking forward to running in a diaper, but at least the running pants and t-shirt will hide everything, and the pounding freedom of exercise is something he needs to clear his head.

A few hours later, and Sam has mostly gotten over looking at his dress with that admiring face, and even teasing Sam about his poor sigil-making isn’t enough to keep his temper down anymore. He’s back in his dress, he’s on free time, but Meg or Benny has come in twice already and sent Sam out and lifted up his skirt, slipped fingers into his diaper. And they’re disappointed that he hasn’t used it. But he can’t, not with Sam right there, especially not now that he’s pissed off at them for making it all blatant and stuff. His stupid sub brain keeps trying to remind him of this morning, but for once it’s Dean who’s mad, even while his sub brain is showing him pictures of Benny and Meg protecting his privacy, giving him time with Sam, promising to make it good for him.

God, he wishes Sir were here. How dare Sir leave him with something hard like this? He shoves down the memories of all the explanations of that, too. The anger feels good, powerful. He’s missed it, kinda. Sure, it makes him feel sort of queasy and sick, but energized, too, and it’s not like Sir is around to care.

“Dean?” Sam asks, and Dean shakes his head a little. He’s dying to take a leak. Seriously, really badly, he’s gotta go. He can’t think of anything else. His brain is running in like twenty pissed off directions at once.

“I got something stuck in my teeth,” he says, standing up abruptly. Screw Benny and Meg anyway, they don’t get to tell him what to do. Jesus, it’s not like they’re Sir, anyway, they’re just assistants, this’ll be easy. “Gotta find a mirror, it’s driving me crazy. Be right back.”

“Dean,” Sam says again, kind of helpless and worried and warning all at once, and Dean points a finger at him, eyes narrowing.

“I’m getting something out of my teeth, Sam. I’ll be right back.”

Spinning around before Sam can say a word, he heads for the door quickly, there’s a bathroom right down the hall, and he can be in and out before anyone even blinks. And there’s no one in the hall, and he knows there aren’t any cameras here, so he slips into it, home free. God, the sight of the toilet is like heaven. He hikes up his skirt and tries to figure out the best way to get his cock out without it being obvious that he’s done so. Maybe through a leg hole, but they’re really snug...if he puts one leg up on the toilet…

“Dean.” Benny’s voice behind him drops into the room like a stone and Dean’s foot slips on the toilet, and he flails and catches himself and gets back upright, barely, heart hammering like crazy, and he turns around real quickly and Benny is standing right there and Meg is right beside him.

“I didn’t, I wasn’t,” he babbles, dropping his skirt real fast, backing up against the sink, his heart sinking. Their faces are like stone, they look so disappointed.

“Don’t compound your offense by lying,” Meg tells him coolly.

“Benny,” he appeals, voice thick in his suddenly too-tight throat, “I just, I didn’t--”

“Quiet,” Benny commands, and Dean’s mouth shuts with a snap. “Can you imagine Dean showing this level of dishonest and disrespectful behavior with Castiel?” Benny asks Meg, and Dean’s mind is whirling panic, and he’s still mad, but oh shit they’ve caught him oh shit.

“I can’t,” she answers calmly, still watching Dean with those eyes.

“I believe it is time for Dean and me to come to an understanding,” Benny tells her. “You can have your class with Sam early?” She nods. Dean can’t even speak. Benny’s never punished him. “We will have lunch privately together as well, if you can have Claudia bring it to my quarters?” She nods again. Dean sucks in air and looks around like an escape route will magically present itself, but his knees feel like water and he feels about an inch tall and he’s never seen Benny like this, all iron-cold and forbidding and hard.

“Come with me,” he orders Dean, and Dean steps forward like he’s on a string, his hands twisting in his skirt.

“Sam,” he says weakly.

“We will let him know where we’re going.” Benny takes hold of the back of his neck and marches him back down the hall. His mind’s a litany of oh shit oh shit oh shit and he still has to pee, that’s somehow the worst of it.

Sam’s worried face pops out of the study door, and then falls into kind of resigned understanding when he sees them.

“Plans have changed,” he hears Meg say, and then he and Benny are moving out of earshot, towards the back of the house.

“I can explain,” he tries, the silent walking breaking the words out of him as Benny opens the door to what Dean guesses are his quarters, he’s never been here before. “Benny, please-”

“Quiet,” Benny says again, though it’s just an order this time. He moves Dean briskly through what looks like a nice living area, to the back, and straight to a big heavy bench that has a red paddle and a lot of other things on it.

“No, Benny, wait.” Dean wakes up or something, he doesn’t know, but he digs his heels in finally, fear flashing through him. “Wait, you gotta listen--”

“Was there an emergency requiring the removal of your diaper that you couldn’t reach Meg or myself in time for?” Benny turns him, holds him, looks him right in the eyes. Dean can’t hold his gaze and looks down.

“No.”

“No, what?”

“No, sir,” Dean gets out, guilty and small.

“Were you going to use the toilet, in violation of the trust Meg and I gave you so you could have time with Sam?” Benny shakes him gently, his hands are like steel.

“Yessir,” Dean admits, and sets his jaw stubbornly against the sudden urge to cry.

“Arms up,” Benny says sternly, and Dean lifts his arms obediently. Benny pulls the dress off over his head, folds it neatly, and sets it aside. Then he unfastens Dean’s diaper, sets that aside too.

“I-I’ve still gotta go,” Dean gets out, his throat thick, eyes wet, but Benny just ignores him. Moving without a lot of rush, he guides Dean to the bench.

“I have a different punishment philosophy than Castiel,” Benny informs him coolly. “I prefer to do it once, and make it memorable enough that it’s not required again. Take the paddle, the belt, and the cane, and put them to the side, Dean.”

“Bennyyyyy,” Dean begs, and it’s almost a wail, even as he’s moving to do as he’s told, eyes blurry. He shouldn’t be scared, he knows it, this is Benny, the big friendly bear, but he is, oh he is.

“You’ve earned this, and once it’s done, you’ll be forgiven,” Benny says without any give, and clears the rest of the tools off the bench. Then he sits and pulls Dean across his lap without ceremony. “Hold the bar above your head,” he orders Dean, who reaches up with shaky hands and finds it there and grips hard.

“How-how many,” he pleads, his face down against the cushions, butt up over Benny’s thighs. It’s a stupid position, he thinks, with a flare of comforting anger.

“Until I think you’ve had enough,” Benny says firmly, and the first smack of the paddle lands.

At first Dean thinks this will be okay. It’s a big hard paddle and Benny’s using a heavy hand, but it’s not devastating like the switch. But Benny is like a machine. The smacks come down again and again and again and pretty soon Dean’s squirming in earnest and his feet are kicking up off the ground and it’s starting to burn, really badly, and it’s quiet, no counting, so it’s just Dean and the pain and the way his own heavy breath is making the fabric of the bench damp under his face. A hard hit on his sit-spot drives a grunt out of him, and then he’s making noises, little huffs of impact every time the paddle lands, whining through his teeth when real tender spots get hit.

There’s a pause, and Benny’s hand on his rump, and he’s knows it’s not done, but he dares to hope…

CRACK the belt is blistering fire on his tenderized bottom and he’s shrieking and kicking before he even realizes it, letting go of the bar, hands flying back behind him to shield his bottom.

“Move your hands, now, Dean,” Benny’s voice brooks no disobedience, and Dean finally sobs out loud, and reluctantly drags his hands away.

CRACK no no no he can’t, he can’t, he’s kicking and twisting and then Benny has a leg over his legs, pinning him, he’s trying desperately to hang on to his anger but it’s moving out of reach, slipping away, leaving remorse and cleansing pain and penance behind. CRACK CRACK CRACK CRACK CRACK “BENNY NO BENNY NO PLEASE,” he shrieks, trying to rear up, but he has no leverage, and a hand pushes him back down. His whole ass is just fire, a mass of pain now, he can’t even tell where the belt-stripes are. CRACK CRACK CRACK

He arches his back, trying to dig into Benny’s lap and escape with his hips, and breaks. “I’m sorry,” he wails, “I’m so sorry, so sorry Sir, Benny, I was wrong, it was wrong, I know it, I’m sorry, please please…”

CRACK CRACK and then there’s silence for a moment. Benny’s hand is heavy on the back of his neck, and just rests there for a moment. He’s gasping for breath, face wet. He’s vaguely aware that Benny’s lap is wet, too, and he should be concerned about that, but his mind is foggy, fuzzed with regret, the agony of punishment, the fluid feeling of paying for his bad behavior, forgiveness waiting for him on the other side.

“Almost done, cher,” Benny’s voice is almost gentle, now. “You’re being very brave.”

Almost? There’s more? Dean struggles weakly, but then the cane hits, and his mind whites out.

He’s screaming, he knows that, but everything else is just raw sensation. It’s probably only three or four hits, but on his raw bottom, they’re agony. Without the hand on his neck, he would have flipped himself off Benny’s lap, he can feel his whole body fighting to escape. It takes him long moments, sobbing wildly and struggling and gulping out his remorse, to realize that it’s over, that Benny’s hands are holding him close, not holding him down, and he breaks into fresh tears and clings tight and burrows as close as he can to the big man.

“There, it’s all right,” Benny rumbles, soothing and low, hand rubbing gently at the back of his neck, flooding him with feel-good feelings even as his butt seems to fire worse and worse pain into him every time he moves. “You’re all forgiven, cher. The slate is clean, it’s all right.”

“B-Benny, Sir, Benny,” Dean sobs into his chest, feeling lightheaded with relief, almost dizzy with it, almost floaty, like he gets sometimes in subspace. Benny has him, he can feel it now, right down to his bones, he can relax and let go, Benny will take care of him. “Please, please,” he begs, incoherent, not sure at all what he wants or needs, but sure he wants to serve Benny, be good for him, make him proud and happy.

“Shh, baby, you’re all right. Deep breaths, Dean,” Benny hums to him. Slowly, gradually, he calms, though he keeps that fuzzy edge to the world. His bottom throbs with every heartbeat.

Gently, Benny unwinds them, once Dean’s breathing is back to normal, and Dean makes a little protesting noise, but Benny hushes him.

“I need to get us cleaned up, and then we can sit some more,” he tells Dean, easing him down onto the bench on his hip.

“Please, sir, let me,” Dean doesn’t know how to articulate it, this powerful drive to prove his Submission, this primal need to serve. He hasn’t felt anything like it except with Sir. It’s not like that, really, he doesn’t want to kiss and love Benny the same way, but he wants to please him, give him pleasure. Be good for him. It feels like it will fill some of the emptiness Sir’s leaving has left him with.

Benny watches him thoughtfully, with dark eyes, the way he reaches out. “All right, cher, I understand. Present, Dean.”

Almost crying with relief, Dean scrambles up into his favorite position. He gets his head down and his aching bottom high in the air and breathes a deep sigh, sinking into it, and barely flinches when Benny’s fingers circle his hole, wet with lube, then push in, stretching and prepping him. Lots and lots of lube, he kind of drifts on the feeling.

“Head up, honey. Get me hard,” Benny says from in front of him, and he’s naked, standing there, only halfway erect. That’s strange to Dean, who’s used to Sir getting hard when he’s punishing Dean, but he eagerly lifts his face and opens his mouth, taking Benny’s cock into his mouth and working his tongue, hollowing his cheeks, using every trick he knows. Benny’s hands are in his hair and that’s so nice, and he hardens fast in Dean’s mouth, salt-bitter rewarding Dean’s tongue when it probes the slit at the tip.

“Good boy, that’s very good,” Benny praises, and Dean shivers with pleasure at doing well. He sucks hard as Benny pulls out, releasing him with a slick pop, and Benny tugs his hair a little, and Dean glances up shyly to see him smiling.

He’s being good. Benny has him. The ground feels steady under his feet for the first time since Sir kissed him goodbye.

Benny’s thick cock working into him is amazing torture. It doesn’t hurt, he’s too well-prepped, but his ass is so inflamed that the motion hurts anyway, so he gasps and moans into the bench, hands clenching and releasing, hips arching as he tries to open them more, ease the fire on his bottom. When he starts thrusting in, steady and strong, Dean buries his face in his hands and lets the motion rock him back and forth, his cock swinging small between his thighs, his ears tuned to the murmurs of praise Benny keeps up the whole time. Every word eases Dean until he’s nearly purring, and when Benny comes inside him, pumping hard and fast, Dean works his cock just like Sir taught him, until he stills, finished, and gently pulls out. Dean feels bone-deep satisfaction, knowing he pleased Benny, that Benny came inside him. Like something hungry inside him has been fed.

Benny wipes him down carefully, and then helps him to his feet, pulling him close. His knees are still wobbly, but he goes eagerly, and the hug is delicious, all that skin warm against his own.

“That was so sweet, Dean. Very nice, I’m very pleased,” Benny’s voice rumbles under his ear. “Can you sit here for a moment? I want to get a cream for your bottom, and some pants for me, and then we’ll sit together on the couch for a while until lunch.”

“Yessir,” Dean murmurs, his throat dry. He can’t sit on his butt, but he can perch on a hip, and he watches Benny move around the room, getting scrub pants and a soft t-shirt on, a bottle of water, a canister of cream, another diaper, before helping Dean stand up again and bringing him to the couch. Dean’s gulping some of the water when there’s a tap at the door, and Benny calls to come in.

Meg steps through, glancing between them with a smile, all the forbidding coldness from before gone.

“Everything good?” She asks, and it’s the first little break in the haze Dean’s mind’s been in since the punishment, but it’s okay.

“Better than good,” Benny confirms, in his normal voice, and Dean flushes a little as she walks to them and reaches out, cups his cheek.

“Better, duckling?” She asks, fondly, and he nods.

“I punished him very strictly, and he reached his headspace,” Benny tells her, though his hand never stops petting Dean. “And then he asked for reassurance himself, through sexual submission. He was a very, very good boy.”

“Dean, that’s so good,” she praises, and he hides his face against Benny’s shoulder to conceal the way he knows his face is bright red with pleasure. He’s starting to feel a little more normal again, but everything still feels raw and close to the surface.

“My goodness,” she says mildly, and he lifts his head to see what she’s talking about. She’s looking at his ass, and he flushes even more.

“Normally I wouldn’t mellow the punishment with soothing cream, but given that he needs a diaper shortly,” Benny holds up the cream with a smile. “Want to do the honors?”

“Sure,” she agrees, and slides in next to them, opening the little jar. “I haven’t seen a butt this purple since you punished Ash for stealing your enema setup and breaking it,” she muses out loud, over the sound of Dean’s hissed breath at the touch of the cold cream on his burning-hot skin.

“Ash is a Switch, though?” Dean manages to ask, trying to distract himself from the pain, though after a moment, the cream brings a blessed cool numbness.

“He is, leaning Submissive. But he’d taken the kit three times already, and both Benny and the boss had warned him about it, made him aware of the consequences. But he had this hot date, and said he really really wanted it…” she sighs a little laugh. “He never touched it again after that last time, though.”

“I bet not,” Dean says fervently.

“There,” she says, smoothing her hands over his rump gently. “I know it feels terrible, but you’ll be fine in a few days, and the diaper will actually help you sit comfortably. Has he at least used it again?” she asks Benny.

“He wet in my lap during punishment,” Benny tells her easily, and Dean has to hide his face again.

“Didn’t even feel good, did it, Dean,” she asks knowingly, and he shakes his head. “Don’t hold it in like that. I think we’re done with the games, yes?” He nods, fervently again. “Then you have a brother who’s fretting about you in the library. I know the plan was for a private lunch, but it sounds like maybe we could be flexible?”

Benny nods, and shifts Dean a little, who squeals and lurches to his feet as weight comes down on his bottom. Then he stands there, red-faced, as they both look at him knowingly.

He swears to himself right then and there that he’ll never ever give Benny reason to punish him again.

Back in his diaper and dress and walking so so carefully, gingerly on his toes, like he’s carrying full glasses of water, Dean follows Benny back to the library. In the hallway, though, something strikes him.

“Benny, how did you know I was sneaking out to the bathroom?”

Benny smiles a little. “Cher, we hope for the best but expect the worst when it comes to training, so we had a little motion detector set up on the bathroom door. Sometimes it’s not the training itself, sometimes it’s pure contrariness, or bratting, or just testing, but we like to know what’s going on.”

Dean nearly facepalms. His dad would be ashamed, him missing a motion detector like that, and he’s embarrassed he underestimated Benny and Meg, but all that’s pushed aside by the relief on Sam’s face when they walk into the library.

“Dean! You’re not dead!”

Benny belly-laughs at that. “We’re not that scary, surely?” he offers, and Sam shrugs.

“Dean was really bad, and you looked really serious about it.” He walks over and slings an arm over Dean’s shoulders.

“Ugh,” Dean scowls at him. “I’m fine, Samwitch. Geez.”

“It’s about time for lunch, and Dean’s walking a little more slowly than usual, so we should probably get going,” Meg urges them.

“Can I see?” Sam asks, grinning.

“Absolutely not,” Dean says, appalled at the very idea, and tries to shrug off his arm without jostling his own sore bottom at all. It doesn’t work very well, Sam has arms like an orangutang. “Get off me, you moose.”

“Boys,” Meg says, fingers tapping on her arm, eyebrows up, and they hustle.

Dean can’t sit in the chair for lunch, and ends up kneeling beside Benny, as the best alternative option.

Finding out that he can’t actually just use the diaper when he wants to is an unpleasant surprise. He tells Meg when she checks on him, a couple of hours after lunch, that he’s been trying, and he just can’t, and she nods at him like it’s no surprise at all. He’s a little startled when she tows him into the bathroom, though.

“Human brains are weird,” she tells him with a smile. “We’re all kinds of conditioned, and it’s pretty easy to do, and pretty hard to break. When you were a kid, you were conditioned that when you had to pee, you did it here, if you were inside, and nowhere else, so help you God, probably. So now it’s really difficult to let go anywhere else.”

“So I can use the toilet?” He guesses, and frowns when she chuckles.

“No But you can stand in front of it and close your eyes.”

He huffs at her, but there was a lot of iced tea at lunch, and he’s willing to try whatever. Astonishingly, it works like a charm, and he’s able to go almost instantly. His eyes fly open in shock as he soaks the diaper.

“Human brains, weird,” she nods, her hand warm and steady on the small of his back.

She changes him just as easily as Benny did, though she makes it almost fun, scratching his belly with her nails gently, rubbing his Angel glands a little. And she praises him the whole time, which is awesome.

He can’t help but mention the weird conditioning thing to Sam, too, because he knows that’s just the kind of thing that turns the kid’s crank, and sure enough, he lights up with a million questions. Meg stays, and they have a pretty cool discussion about conditioning and training and establishing and breaking it and all kinds of pretty fascinating stuff that goes on right through dinner, which he barely eats, and before he knows it, he’s saying goodbye to Sam, telling him to be good and study hard, that he’ll see him soon, and getting wrapped up in an octopus-hug.

Fuck, he loves that kid.

He’s really, just, super-tired, though, and sick of wearing this dress, and he leans a little bit on Benny as they head towards the play area. Honestly some time in the age play room sounds kinda good right now, his brain’s tired, and his butt hurts like crazy.

Meg’s already there when they come in, dressed in something soft-looking and reading a book, and she looks up with a soft smile that he can’t remember seeing on her before, but it’s really nice.

“Hey Benny, hey sweetheart. You ready to settle in?”

“Definitely,” Benny says, and Dean nods too. It’s nice and warm in here, and the lights are kind of low, just warm soft lamps on the side tables. Benny moves off to the small bedroom, and Meg comes to Dean’s side.

“Let’s get you all set,” she says gently to Dean, and takes him to the changing table, helps him out of the dress, which gets folded and put away. He sighs a little with relief to feel his skin breathe again, and goes willingly when she urges him up to the changing table.

“We’re going to help you be a little younger than you might otherwise play here,” she tells him quietly, moving around the table. “You can still tell us if something’s bothering you, but I want you to try to be quiet if you can, okay, honey?” He nods at her, already feeling the atmosphere of the room, quiet and peaceful, steal over him. She holds a rubber soother to his mouth, and he makes a face, but accepts it. It feels kind of awesome against his tongue, actually, and he gives it a few experimental sucks. So satisfying.

“Good boy,” she murmurs. “Left hand, Dean.” She takes it when he holds it up, and puts a funny-feeling foam ball in it. “Squeeze.” He does. “Okay, let go.” The foam has formed and is stuck to his fingers and hands, kind of like a glove, making his fingers stiff and clumsy. Like a kid’s, he thinks, wonderingly. He stares at his hand and sucks on the soother, and Meg has him do his other hand, but he barely notices.

He sees Benny behind her, moving around the kitchen, just normal things, filling a glass of water. He’s wearing scrubs and no shirt, though, it looks like he’s getting ready for bed.

“Seepin?” he says, around the soother, and Meg smiles at him.

“Not yet, baby. Are you going to need help to mess your diaper if you need to? Be honest. We have a few things that will make it easy for you to not have to worry about it at all, if so.”

Dean’s tired mind worries at that for a moment, but he shakes his head. It was okay, this morning. And he doesn’t have to go, yet. He can worry about that later.

“Okay.” She slides a slim hand into his diaper, it’s dry, and helps him off the table. “Why don’t you come sit and read with me for a little while? I got some special books just for my special boy.”

He blushes, he can feel it, and he can feel his mind start to go syrup-slow and soft, with relief. He nods, and follows her to the big armchair. He’s not sure he’ll fit, but she eases him into position in her lap so he can see the book okay, his head kind of against her arm and shoulder, pillowed on the big soft arm of the chair. She smells soft and warm and sweet, somehow, and he sighs in a huge breath and lets it go, feeling himself go limp in her lap.

“There’s my sweetie Dean,” she says, smiling down at him.

“If that isn’t a picture,” Benny says, sitting on the couch, his own book in hand. “Auntie Meg and her best boy.” He’s smiling at them too, all wide and crinkly, and Dean has to smile back.

“Annie Meg,” he tries it on, and likes the sound, though talking with the soother in is annoying.

“That’s right.” She opens the book and holds it so he can see. “Once upon a time, in a land far away…”

The story is good, but Dean keeps drifting off. He’s not sleeping, not really, but sucking on the soother and the quiet in the room and Auntie’s steady reading voice are putting him into some kind of trance. All of the craziness of today, the struggles, they’re all slowly falling away, like shingles off a roof, leaving just quiet small Dean behind.

“Here, sweetheart,” Auntie murmurs to him, when the story’s had a pause for a while. She tugs the soother out of his mouth, and he makes a wordless protest. “Shh, baby, no, it’s okay.” Then she’s lifting something better to his lips, nudging the nipple against his mouth, and he instinctively knows what to do. He turns a little into her, eager, and latches on, the first rich spurt of warm sweetness in his mouth like heaven. He suckles hard, bringing the milk out, swallowing it eagerly.

“Ohhh,” she sighs, and he hums delight against her breast. He feels so safe, her hand cradling his head close. The milk is coming on its own now, he barely has to suck, just swallow, it’s bliss. He feels like he’s barely had enough when it slows, and he suckles demandingly, but she puts a gentle hand on his cheek and pulls her breast from his mouth.

“Gently, baby,” she murmurs, smiling down at him, her eyes bright and cheeks pink, and he blinks slowly at her, then moves a little clumsily as she guides him to her other breast. Just like the first, he nuzzles in, soft warm against his face, sweet goodness on his tongue. He feels a surge of devotion, fondness, belonging, and closes his eyes and nurses.

“He didn’t have much dinner,” Auntie Meg says quietly, as he’s sucking to pull the last drops. “I think the baby’s still hungry, Uncle Benny.” Dean’s the baby, he knows that, and he doesn’t want to let go, whines as she pops her thumb into his mouth, breaks the nice suction he’d made, and releases her breast. “Greedy sweetheart,” she says, and kisses his nose, his cheeks, the corner of his mouth, little sweet kisses that make him scrunch his nose and smile.

“Come here, handsome boy, we’ll see what we can do about that,” and that’s Uncle Benny’s big rumbly friendly voice, and he’s being scooped gently right up off Auntie’s lap and carried to the couch. Dean’s happy to see him and pushes a couple of little kisses right on his shoulder, and then he’s getting settled right to Uncle Benny’s nipple, too, and he blinks up, curious.

“Go ahead, honey,” Uncle Benny strokes his hair back from his face. “I promise.”

Curious, Dean nuzzles in, then latches on, and sucks, and it’s just like with Auntie. He hums eagerly and roots in, greedy, and Uncle Benny’s making a purring kind of noise, his arms are strong and warm around Dean, safe, protective.

Auntie and Uncle are saying things, talking, but it’s just noise to Dean right now. He’s pure simple innocent instinct, all the upheaval of the past hours being soothed away by this oldest ritual. The milk is sweet and rich, and when he’s shifted to Uncle’s other side, he’s finally nearly satisfied, just swallowing idly, nursing a little, his head easy in the crook of Uncle’s arm, watching him with drowsy eyes as he talks.

“Finish your milk, baby boy,” Uncle Benny tells him gently, looking down at him, rubbing a soft thumb to the corner of his mouth. Dean blinks at him, and suckles a few times hard and strong, until the milk is spurting and Uncle makes that purring sigh again. “Good boy, Deanie,” and that makes Dean feel all warm and squirmy. “He takes to it beautifully,” he’s talking to Auntie again.

“Dean’s very primal in a lot of ways, and this is about as primal as it gets,” she answers softly, and then Dean stops listening again, and just feels.The warm nipple in his mouth, the body pressed against his, feeding him, giving him this closeness.

His tummy is so full and warm and happy when he’s finally done. Aunt Meg washes his face and gives him back his soother, and pushes on his belly until he goes pee in his diaper. That’s okay though because the dry one is red, and Dean likes that, and he plays with a stuffed giraffe that has a really silly face while Meg is getting him all clean and dry.

Real exhaustion has set in by then, though, and he can barely keep his eyes open. So when they put a soft legless onesie on him and tuck him into bed, he only vaguely notes the crib bars, and mostly just that he can see through them to Meg slipping into the bed beside his.

“Sweet dreams, baby,” she tells him, gentle and fond, and he crashes into sleep without a second thought, clean and warm and safe.

Chapter Text

Meg’s ears, attuned to any disturbance in this situation, wake her immediately at the sound of a groan and then a bitten-off gasp from the crib beside the bed. Glancing at her phone, she notes it’s just a little after midnight; he’s slept for over four hours, then, which is more than she’d hoped for in a strange bed and in these strange circumstances. She clicks on the bedside light, dim and not too intrusive, and rolls out of bed to go to the crib.

Dean’s awake, for sure, and lying rigid in the crib, his lower lip caught between his teeth. He’s woken up big, and sore, and uncomfortable, which she’d half-expected. She reaches down and strokes his cheek, and he scowls at nothing, face going red, turning away. Ah. She smiles at him, and opens the side of the crib.

“All the soft fuzzy feelings are gone, and now everything hurts, and you want the bathroom? And your mind is beating you up, too?” She can read it in his face, his body, even the way he’s holding his clumsy hands, but saying it out loud lets him know she understands. He turns back to her and the scowl drops, and he just stares in surprise, those big green eyes and his mouth dropped a little, and she grins at him like normal, like she would any other day.

“I can’t move my butt at all,” Dean grumbles, his voice rough, and she nods.

“You’ve gotten all stiff. Come on, let’s see if we can get you more comfortable.” She holds her hand out to him, and he puts his foam covered one in hers, frowning at it.

“I don’t like those,” he declares, as he moves with infinite slowness, wincing and stopping regularly, to the edge of the crib and eases to his feet.

“That’s okay,” she tells him. “It’s okay to not like certain parts of this, but we’ll talk about it a little more once you’re comfy. Moving around some will loosen up those muscles, and you need to use your diaper.”

He flushes a dull red, and looks away, though she doesn’t let go of his hand. Moving nice and slow and ignoring that for now, she leads him slowly out of the bedroom and on a slow walk around the living room, letting him stop when he needs to, until he’s walking with a little more freedom.

“I can give you medicine,” she starts, and Dean pulls his hand from hers sharply.

“I don’t like that medicine! It made my stomach hurt,” he bites out, not looking at her, still red.

“All right,” she says, evenly. “Dean, if you wet and mess your diaper on your own, I can get you changed, and put the cream on your bottom, and help you stretch, and you’ll feel a lot better. If you don’t, I will use the medicine, all the other things will still happen, and we’ll talk about some other options with Uncle Benny when he comes back for breakfast.” She reaches out and takes his hand again. “I know you’re out of sorts right now, but I’m here to help you through it. It’ll be okay.”

“It won’t,” he insists, staring away from her, stubborn. “That stuff we did, last night, that was crazy, I never even thought...”

“That was beautiful and sweet, and I won’t have you talking down about it,” she lets a little sharpness slide into her voice, and he looks at her, startled. She’s always been the no-nonsense one, here, and he’s always responded well to it. “It’s the most natural thing, feeding a child, a person, from the breast. It felt wonderful to me and Uncle Benny and and I know you loved it too, and I won’t let you lie to yourself or to me about it.”

Abashed, if only a little, he tips a shoulder at her. “I guess,” he says, sounding very young and sullen.

“And we’ll be doing a lot more of it, too,” she informs him, and he honest-to-goodness shivers, and looks down at the floor again, biting his lip. “I can tell that’s going to be okay with you,” she says, gently again. “It’s a nice thing, that closeness. It can be hard to trust and connect, and this can a wonderful way to bring that togetherness quickly, for Submissives and their Dominants, and it’s a good thing, Dean. But right now, let’s focus on getting you comfortable, hm?”

His legs are almost crossed, and he’s touching his belly off and on, too.

“I don’t want the medicine,” he insists.

“You can try without. Come here.” She leads him to the couch, and sits in front of him. “Squat down, put your head in my lap.”

“Oh my god, I don’t think I can,” he says, eyes wide, and she lifts an eyebrow.

“Go slowly,” she suggests. “Ease into it,” she encourages him down, through his wincing gasps, until he’s crouched between her knees. “Good boy, very good,” she praises, and watches his pupils dilate in reaction to the praise. “Now put your head in my lap, take some deep breaths, and relax.” He puts his head down easily enough, but the tension in his body is evident through the thin cotton of the loose onesie he’s wearing. She rubs the back of his neck gently, but even though his shoulders ease, his back is a hard line, and his breath isn’t slowing. For long minutes she pets his head, strokes his shoulders, hums a little, until she notices his thighs are starting to shake, and then she lifts his chin with her hand.

“Not working?” He shakes his head, jaw clenched, breathing hard through his nose. “Okay, stand up. It’s not good for you to hold it in, baby. Come on.” She stands up with him, puts a hand on his back to guide him to the changing table.

“No,” he refuses, planting his feet. “I can use the toilet.” He sounds frustrated, tired, a little scared, testing and pushing, and she nudges up behind him, shoving until he steps off balance and then she keeps him moving, her hand on his wrist gently twisting, a hint of a threat.

“Castiel and Benny and I started talking to you about this a while ago, and do you know why?” She doesn’t wait for an answer, just pins him against the table with her body, using just a hint of extra strength and leverage. He shoves back against her and then flinches away when his butt comes in contact with her. “Because we wanted you to be as comfortable as possible with this in your mind and accept the idea and be able to ask any questions, let it settle. We’re trainers, not torturers, and we want you to have good and pleasant associations with the diaper. Good feelings, good experiences. So far it’s been working pretty well, yeah?” She urges him up on the table.

He goes dead weight in her hands, the brat, and if she hadn’t been prepared for it, he would have collapsed back on her. But she is, and she claps a hand to his ass and shoves, and he jolts and scrabbles frantically away with a strangled shriek, twisting as he lands on the table.

“Don’t push me,” she says firmly. “We want this to be a good and positive experience, but you will use the diaper.”

“No!” Dean protests, even though he’s on the table now, on one hip, half reclined. “I don’t want to, I WON'T,” he insists, his voice hoarse, his face tight, eyes narrow.

There’s the challenge statement she’s been waiting for, and she moves instantly, fingers targeting the big nerve cluster at the top of his thigh. She pinches and twists and he yells in shock and pain and surprise and collapses down on his back, and she knows his leg is all pins and needles.

“Do not think that because I am physically smaller than you, that you may disrespect me,” she puts the full weight of Dominance into her voice and stands directly over him, and he tries to shrink back into the table, eyes shocked and wide.

“No, ma’am,” he says carefully.

“Good boy,” she approves firmly, and unsnaps his onesie without ceremony. She pulls the whole thing off over his head, too, gently working his arms and head out of it, since she expects he’ll need the comfort of skin contact before too long. The room is still warm enough that he doesn’t even shiver, though he turns his head away as she unfastens the diaper. It’s a little stretched and creased from being slept in, and she leaves it open under his hips as she grabs one of the glycerin suppositories from the cool lower shelf.

“Turn over, kiddo,” she pats his thigh.

“No way,” he mumbles at the wall, and crosses his arms defiantly over his chest. Well, she tried, she tells herself, and reaches underneath him, grabs a handful of his ass as the other hand grabs his shoulder, and deftly flips him, using his own weight and bucking attempt to get her touch away from his tender bottom against him. He rolls pretty well, she thinks with humor, and she gets his leg bent up behind him quickly as he lands on his belly.

“No!” He tries to pull it free, but he’s not really defying her, there’s an edge of frustrated tears in his voice. “I don’t want it!”

“I know, but it is necessary,” she says firmly. She’d rather keep this sweet and gentle if possible, but there’s something to be said for just getting it done and over with, so she nudges her knuckles in between Dean’s clenched, bruised cheeks, lining up the bullet-shaped suppository with his little hole. “Deep breath, baby,” she warns him, and then presses it home past his resistance, following it in with her finger, working it up deep inside him.

“Noooo,” he tries to pull himself up the table, away from the intrusion, but she presses down on his captive leg and he goes still and shivery. She works her finger firmly in and out, making sure the suppository is in nice and deep, fully lodged inside, before pulling free.

“Back over, now,” she says gently, and Dean rolls without protest. His cheeks are a little wet and his mouth is set in a sulky line and he stares at the ceiling, but she fastens the diaper back on with soft hands, and rubs his belly and breasts a little, until his breathing calms and some of the tension relaxes.

“There. Do you want to stay here until you mess your diaper, or come sit on the couch with me?” She holds his hands between her own as he opens and closes his mouth a few times.

“This wasn’t so hard yesterday,” he finally gasps out, like the words are being forced from him, and she nods and instead of making him choose, climbs right up on the table with him, slipping under his head and shoulders so he’s supported by her lap. She urges him to his side, too, and reaches down to tug at his knees until they’re drawn up, and he fidgets, but follows her hands.

“Sometimes the first time is easiest. Then we have a little time to think about it, and we get all caught up in our heads and remembering the experience and second-guessing it, and that makes everything more complicated and difficult.” She feels him nod against her thigh, and looks out into the dim, quiet room, stroking his hair.

“It’s all a lot,” he says, voice small.

“It is, but it can be easy, too. If you can relax and give up control, you can enjoy it again. I think Uncle Benny and I will make it easier for you tomorrow, okay? Let’s just get you comfy tonight. I know how tired you are.” He’s not in any kind of age play headspace, but using the terms and phrases come easily in the room, and he seems to respond well to them anyway. He relaxes a little more with another nod.

“Sorry I was a shit earlier,” he says unexpectedly against her leg, and she chuckles.

“That was pretty minor, Winchester. But thank you for apologizing, and you’re forgiven. I know you’re trying, and I appreciate it.” She keeps her hand on his shoulder when he bends abruptly around his belly. “Relax, let it go,” she soothes.

“Don’t wanna,” he whines, but it sounds hopeless now, and a moment later he’s shoving his face into her lap with a small grunt of effort, hands gripping her leg, and she can see the relief ripple through him, a few small sounds the only sign of his release.

“Wet too, baby,” she reminds him, “What a good boy you are, that’s so good, Dean, I’m so proud of you, I know it’s hard. Go pee, now, let it all out, get all comfy, and I’ll change you and we can relax and sleep again.”

He nods against her leg, all the fight clearly gone out of him, and hums against her thigh, squirming a little. She knows the diapers will catch and soak in all the liquid, but also knows that with a full diaper, the sensation will be new and strange for him.

What a good boy,” she praises,” pleased Dominance running richly through her voice, and he squirms again, with pleasure this time. “That was so good, Dean, don’t you feel so much better?” She lifts his face gently out of her lap, and he’s pink and a little tight around the eyes, but smiling slightly, too, in what looks like relief.

“Yeah, feels better,” he admits. “Still don’t like that medicine,” he tacks on, and she grins.

“Noted. I know, it’s a little harsh. Time for a clean diaper, hmm?” She slips back off the table, businesslike, and slides the changing blanket under his hips. She pretends not to notice as he grabs the stuffed giraffe that is still sitting by the wall railing, and holds it to his face.

There’s an art to changing a big diaper, and she has it down pat. She lifts and spreads his thighs and lifts his hips, using the diaper to hold most of the mess and wipe the round bottoms of his cheeks. His mess is soft, probably due to all the milk, and she cleans him with a few wet wipes, careful to get it all, the little crevice of his hole, under his balls, his cock, taking her time and humming. She smooths the numbing cream on his buttocks, hearing his deep sigh of relief. She can feel him relax, by degrees, until by the time she slips the fresh diaper under his dry and powdered butt his thighs are splayed open, he’s almost boneless, and his cock is chubby and pink with all the attention.

She’s happy to see him so pleased and more relaxed, since her breasts are starting to become painfully full again, and it’s important that he nurse and reinforce their bond before she puts him down in the crib to sleep. The instinctive comfort and reassurance of nursing will be a big help in the coming days, if she can get him into the routine of it.

“That’s better,” she says, satisfied, as she helps him up off the table. “Don’t you feel so much nicer?”

“Yeah,” he agrees, only a little grudging. Almost all of his body tension is gone, now, and he’s starting to look sleepy again. “Can I sleep now?”

“Come on. Almost. Let’s cuddle a little first,” she smiles at him and leads him to the bedroom, where the crib side is still down. The end of the crib mattress has a soft chair attached for bottle feeding, diaper changes, and breastfeeding, for caretakers of little Submissives given they can be difficult to move once they’re drowsy, and she slides down that side of the crib too, and settles in with him.

“Winchesters don’t cuddle,” he grumps, though he gets into the bed easily enough, sighing with relief as she guides his head and shoulders into her lap again. Even as he’s protesting, he instinctively nuzzles against her, and she smiles fondly down at his face. She quietly slides her milk-heavy breast free of her loose pajama top, and shifts enough so that her nipple rests at the corner of his mouth, and waits for nature to do the rest.

“Just think,” she tells him softly, rocking just a little. “Tomorrow we can play with all the toys. Uncle Benny will be here sometimes, and he’ll play with us too. Your bottom will feel much better, and there’s a sandbox in the little yard outside, we can build a castle if the sun is shining.”

“That’s fun,” Dean says muzzily, his eyes closed, and his lips brush her nipple with the words. He stills, and his sleepy eyes blink open warily, before he sighs and turns against her, sucking her nipple and breast in, making a good latch, going limp in her lap as his eyes flutter closed again in pleasure.

“Good boy, sweet boy,” she croons, riding the wave of endorphins, the Dominant rush of fulfillment and completion that is equally pleasurable to orgasm. Non-sexual Dominance like this is one of her favorite things, and something she seeks out with her service Subs and yes, age play, and breastfeeding. She shelters and feeds and protects this Sub with her body, as he trusts and takes what she gives.

The rhythmic pull of his mouth is sweetly drugging, and she can tell he’s nearly asleep when she moves him to the second breast. He whines until she feeds him the nipple, and then starts suckling by reflex. She’s close herself, and tips her head back, relaxing into the simple pleasure of feeding a Submissive.

Benny’s hand on her knee startles her awake some amount of time later, but she can see morning light coming in through the shaded window. She blinks at him, and then down at Dean, who’s not nursing anymore but is sleeping peacefully in her lap.

“I thought we weren’t going to co-sleep with the baby,” Benny whispers with a grin, and she rolls her eyes at him with a smile.

“Shhh,” she hums. “Are you bursting? We had a restless diaper change last night but he’s nursing sweetly so far.”

“I could feed him,” Benny admits, fingers already opening the buttons on his shirt, and she nods. His chest looks a little swollen. Nothing like the breasts of a woman or a Sub, but she can definitely see Benny needs some relief. Dean stirs and wakes a little when she slides out from under him, but he’s definitely not a morning person, and it’s easy enough to get Benny into her spot.

“Just offer the nipple, and he’ll nurse instinctively if he’s hungry or thirsty,” she whispers, and he nods, something a little wondering in his face. Last night, he’d looked absolutely astonished, almost transported, as Dean had fed from him, and it’s maybe not as easy without a breast, but he gets Dean situated, face to bare chest, and with a little effort, presses a nipple in.

Dean’s sleepy face scrunches and then relaxes, lashes fluttering, and then he’s suckling. Benny sighs with relief, though he winces slightly.

“Intense, until the heavy flow starts,” he explains. “Really good, though. Gets me hard as a rock,” he teases, and grins at her second eye-roll and laughing sigh. It does feel amazing, and she knows Benny is often sexual with his age play. They’ve shared this kind of training before, and it works out well, since some Subs are very sexual, some not at all, and some go back and forth when they’re in this headspace.

“I’m going to take a shower and make some coffee. See if you can put him back down when you’re done?” He nods, and cradles Dean closer, his face soft and fond as he looks down at him.

The shower feels like heaven, and she masturbates twice, pulling herself off, pseudo-phallus between her fingers as she imagines David, the Sub she short-term contracts with in Austin and who screams so prettily when she fucks his penis with her clit. Relieved and relaxed, she’s toweling her hair and just finishing the coffee when Benny joins her in the kitchen, buttoning his shirt again, leaving the bedroom door a little ajar.

“Night go okay?” He grabs a mug and sits at the table. She bumps his shoulder with his hip as she passes by, friendly and fond. They’ve been working together for years, and she knows the kind of easy friendship and communication they have together is precious.

“Mostly. He woke up after midnight, all retentive and stiff and sore. I had to give him a suppository in order for him to pass solids, and he resisted it, even after trying. I had to force it in.” She fills her own mug. A little caffeine in his milk will do Dean good, she thinks with humor, and and takes a big swallow.

“We can’t really keep giving him those, they’re too harsh,” Benny points out. “Time for the injections?”

“I think so,” Meg nods. “Take it out of his hands and control. At least while we’re in here. That way he can get used to the rhythm of soiling and changing, and we can get him a little conditioned to associate it with good things.”

Benny nods, untroubled. “Should we do butt and bladder, or just butt?”

She grins at him, and tilts her hands back and forth like she’s weighing something. “The benefits of him giving up control, or the tantrum he’ll throw at being made to give up control?”

Benny laughs at that. “The urinary sphincter is harder to reach, though. Maybe start with one and see how he takes it? He may wet sympathetically anyway, once he’s soiled.”

“It’s a plan.” She taps their coffee mugs together, and chat a little about Dean; how pleased Benny was when he reached what Castiel calls his ‘penitent space’ and how relieved Castiel himself had been when Benny had reported the whole event during their nightly call, how he’s resisting the diapers still, how smoothly he slipped into a small headspace the night before.

“We did stack the deck a little by tiring him out first, which honestly seems like the best way to do anything with Dean the easy way,” Benny acknowledges, and Meg nods.

“And we know he enjoyed age play with Castiel, as well. This whole age play is in support of the diaper training, to smooth the way for that, and I think it’s a great thing for Dean to experience, but I can’t imagine either of them doing it like this long term, or often. It’s too soft and calm for them.”

“We do like a peaceful house. Just thinking about having to keep three steps ahead of Dean and then keep up with him all the time exhausts me,” Benny chuckles, nodding. “But for the Boss, that’s a dream come true.”

“It takes all types,” Meg says with all the fondness in the world, and then they bend their heads to a few household administrative tasks while their high-maintenance baby is still sleeping quietly.

Benny checks his watch an hour later.

“I have to get back to the house soon,” he says regretfully. “We have a delivery coming in, and I’m helping Cole with it. I hate to get him up, but it’s almost nine.”

“It’s fine. I’ve got a bottle ready, and I’ll give him a bath. We’ll be okay here,” she assures him.

“Yeah, but this is a lot more fun than unloading boxes,” he complains, as they make their way into the bedroom, and bend to gently rouse Dean. He’s obviously in a much better mood than he was last night, smiling a little at her when she helps him out of bed and to the bathroom to brush his teeth and wash his face. His diaper’s dry, but she didn’t expect anything else, and he’s very sweet like this, mumbly and half-awake.

Benny’s waiting by the table, and he takes Dean into his arms for a long hug that Dean seems to melt into; he’s not small, but he almost disappears in Benny’s huge arms, and emerges pink and smiling and ruffled.

“Morning, sugar,” Benny rumbles, finally. “I’m glad I got to see your pretty face before I have to go do some work. Let’s get the diaper off you.” He suits actions to words and lifts Dean right up. “Present, Deanie.”

Looking a little confused, but willing, Dean slips into position, rear facing them and up high, hole exposed. The angry red on his skin has faded, Meg notes, and deep blue bruising is showing here and there.

Benny pulls a syringe and sterile wipes from a little case under the table, and wipes gently around Dean’s hole, cleaning it carefully. Dean tries to peer over his shoulder, but Meg puts a hand on his shoulder and presses him back into position. He huffs a little, but settles, as Benny taps the syringe.

“Aunt Meg told me that you had a little trouble last night,” Benny says gently. “Deep breath, honey, little pinch, be brave now.” He slides the needle in just next to Dean’s hole, depresses the shot, and Dean squeaks, jumping, and Meg holds him steady.

“What, hey, what’s that,” he babbles, and Meg strokes his hair.

“One more,” Benny tells him, and Dean grunts and twists a little. “There. All done. That was so good, Dean, what a good boy.” He puts the syringe away and sits Dean up carefully, cups his red cheeks, smiling at him. “Remember we told you we can help you use the diaper? No more suppositories, I heard you don’t like them, and using them too much is bad for you. These shots will relax your bottom, and you won’t be holding it in anymore, so your belly won’t hurt, and you won’t need that medicine.”

“Benny,” Dean breathes, eyes shocked, and Meg rubs his back soothingly.

“The injection only lasts for a day, baby,” she assures him. “Then everything goes back to normal. But for now, you don’t have to think about it or worry about it. Just tell us when you need a diaper change, and we’ll take care of everything.” Even as she’s talking, Benny’s tugging Dean down on his back and sliding a fresh diaper around his hips.

There are two ways to approach new things that Dean might resist, Meg has found: one, present him with all the information well in advance, let him mull it over and come to terms with it, and hope he meets you in the middle and isn’t strategizing rebellion instead. Or two, treat it as a done deal, just do it, and just keep on trucking through, hoping to keep him a little off balance. The second approach seems to be working right now, as Dean seems a little stunned by it all.

Benny has him off the table and over to the play area before he can do more than stammer a few not-words, and Meg shakes her head fondly, as she goes to fix Dean some breakfast. Supplements, protein, vitamins, everything he’ll need to stay healthy, blended with coffee ice cream and milk. It’s not a traditional bottle, but she thinks Dean will like it, and the sippy cup is convenient.

“I can’t even tell if I’m mad at you,” Dean’s saying plaintively as he shoves a pile of blocks away from him, clearly not having any of it.

“That’s okay,” Benny assures him, crosslegged beside him on the playmat. “You can figure it out when I come back for lunch.”

“Ugh.” Dean flops over sideways onto the soft mat. He might not be a baby right now, but he’s acting much younger than usual, Meg notes, all child angst and drama and petulance. She also notices that he’s being much more respectful towards Benny, even in his upset state, than he would have been yesterday, and she smiles a little bit.

“Here, honey. Something for breakfast.” She holds out the cup.

“Coffee?” Dean asks hopefully, sitting back up, just as she had anticipated.

“Coffee ice cream,” she tempts him, and he looks at the cup suspiciously, but takes it with clumsy hands. Benny climbs to his feet and dusts off his hands.

“Gotta go to work, Meg. Deanie, you be good for Aunt Meg, have fun, okay?”

“Maybe,” Dean mutters, between sips of his milkshake.

“Good enough,” Benny says cheerfully. “As long as you try.” He crouches down and cups Dean’s face in his big hand and gives him a kiss, his other hand patting the front of Dean’s diaper firmly, and Dean goes very pink and flustered all of a sudden at whatever Benny murmurs in his ear.

Smiling, Benny stands and heads for the door. “Promised rewards,” he tells Meg as he passes her, and oh yeah, that’s right. The third method of getting Dean through resistance: bribery. She laughs, and finds a channel on the big television that’s showing old Bugs Bunny cartoons. Leaving Dean to his sulk for the moment, she tidies the kitchen and finds where she’s set her book, settles on the couch.

He’s still on the play mat, sort of facing the television, running one of the toy trucks back and forth idly. Still not little, she notes, and tucks her feet up under her, undoing a few buttons on her blouse and settling in to read. Dean, she knows, can’t stand to be bored. She can wait.

Sure enough, it’s not even fifteen minutes before she sees him moving oh-so-casually towards the couch. She hides her smile in the book, and lets him find his own way. When he’s pressed up against her leg, finally, she drops a hand to his hair, and feels him sigh.

“I’m still hungry,” he demands suddenly, looking up at her challengingly. His eyes keep flicking down to her chest, then away, over and over, and his face is flushed.

“Hmm. All right.” She sets the book down and pulls a big pillow onto her lap. “How about this. If you’re hungry, or worried, or just want to be quiet and warm, and you want to nurse for a little while, you can just do this.” She takes her hand gently in hers and taps her thigh with it three times. “Uncle Benny and I both know what that means, okay?”

“I want real food,” Dean argues, but it’s not convincing at all.

“Hmm,” she tips her head, noncommittal. “Why don’t we sit together first and see. Come on.” She urges him up onto the couch, and he’s a little clumsy and hesitant, but he slides his head onto the pillow willingly enough.

“You’re being so good, Dean,” she praises him softly, as she strokes his cheek, looking into his eyes. “I’m so proud of how hard you’re trying, how brave you’re being with all these new things.”

“Some of them are nice,” he mumbles, abashed, turning his face into her hand.

“That’s right, and even some of the hard things can be nice if you let them,” she reminds him.

“I don’t know why this doesn’t feel more weird,” he comments, almost calm, watching her free her breast, hand already coming up to rest on her sternum gently.

“It’s the most natural thing in the world,” she says, smiling.

“For babies,” he protests, weakly, but then he’s seeking the nipple eagerly, nudging and bumping in to start the flow and suckling hard. The warmth of his pulling mouth spreads through her instantly, and she sighs with pleasure.

Hot sweet milk, skin on skin contact, the soothing primal sucking reflex, she knows they all combine into a powerful cocktail. He watches her as he nurses, this time, big green eyes steady on her face, and she can see the changes as his eyes soften, widen, his cheeks relax, his body eases and curls into her trustingly.

“More,” he says, a smear of white on his plush lower lip as she gently removes him from the nipple when the sucking becomes painful on that side. His voice is very very young, now.

“Slide up, honey, other side.” She shrugs out of her shirt entirely and puts the pillow aside, and he scootches up, now really in her lap. Skin to skin, warm and smooth. “There, now.” He hums happily into her breast, pushing gently with his clumsy hand.

Suddenly his head snaps back and his thighs clench as his wet mouth falls open on nothing, and she holds him steady, rocking a little. She can see alarm, pure shock, appalled realization fighting with his headspace, dragging him back up, and oh yeah, she’d timed this all just right. The early feeding, breakfast, now more milk, and his fully relaxed sphincter has allowed peristalsis to move everything right through without resistance. Now to see if she can keep him down, prevent any negative reaction, ease him through it.

“Baby has a messy diaper?” She murmurs, petting his head, stroking his hair. “That’s a good boy, Dean, what a good little man. You can keep nursing for a little while, it’s okay. Shh, honey, it’s all fine.”

“Nnn, I,” Dean struggles, eyes blinking fast, and she hums sympathetically.

“You can fight it and get upset, and angry, and I’ll understand, and we’ll deal with that. Or you can take a deep breath and nurse for a little bit, calm down, and then we’ll have a nice quiet diaper change and a bath.” She meets his eyes seriously. “That’s up to you, Dean.”

She can see the struggle in his face that goes on for long moments. Then he sniffles a little, and takes the breast back in, and starts nursing almost frantically again. She doesn’t fool herself that it means everything will be clear sailing. But Dean is a smart boy, and he’s a hedonist at heart, and understands clear boundaries. She’s not above a little bribery herself, she thinks with amusement, and Dean did tell her once he’s always been a breast man.

Deanie is very good for his diaper change. The little headspace makes him happy to play with a toy while he’s changed, and he doesn’t even whine when she presses a finger into his loose hole, testing, and it just spreads open without a hint of resistance, all the muscles slack, and stays open even when she pulls away. He’s even cheerful about being helped down and guided to the tub, where she runs him a warm bath with toys and bubbles. He makes an enormous mess of the bathroom, splashing bubbles and water everywhere, which Meg vengefully leaves for Benny to clean up, too busy being charmed by little Dean’s sweetness. They play with a puzzle, and blocks, and Dean loves the big colorful trucks. He’s still a little older than she’d expect, but that’s all right, he seems to have found a balance that suits him, and he’s relaxed and content.

When Benny arrives for lunch, Dean scowls at him fiercely, and throws a truck right at him. It’s clumsy, with his gloved hands, and doesn’t connect, but she still has to clap a hand over her mouth.

“I see you’ve decided to be angry, little man,” Benny says gravely, closing the door behind him. “But we don’t throw things.”

“Bad,” Dean insists, his lower lip sticking out.

“Hmm, I don’t think so, but that was very rude.” Benny strides right to him, heaves a startled Dean up to his feet, and marches him directly to the corner, pressing his nose to the seam. “Ten minutes. You don’t throw your toys, it’s dangerous and mean,” he scolds.

“No!” Dean protests, though he doesn’t move his nose.

“Ten minutes,” Benny says sternly, and leaves him there.

“Things were going so smoothly!” Meg laughs, getting up from the play mat. “But you’re just in time to help with lunch.”

“Want lunch,” Dean says hopefully, turning out of the corner and taking a step towards them.

“Young man,” Meg says instantly, with warning. She puts him right back in the corner, tugs his diaper down, and delivers three gentle slaps to his bottom. By the third, Deanie’s crying.

“Sorry Auntie, sorry,” he pushes his face to the corner, shoulders shaking a little.

She pulls the diaper back up, makes sure it’s snug, and steps away. “Ten minutes. You think about being a polite boy and listening better.”

Just sniffles answer her, but he stays put and doesn’t make a move to stray while they make sandwiches, toast and cheese for Dean with another shake, and sandwiches for the adults. Dean’s already so much more accepting of their Dominance, direction, and correction. In another day, she hopes, going back out into the house and back to their everyday routines, it should be a much easier dynamic. In the meantime, she’ll take this small domestic vacation and enjoy every minute of it.

Chapter Text

The third morning Dean wakes up in the crib, he stretches luxuriously, fingertips to toe tips, and blinks drowsily into the bright light of the bedroom. The shades are wide open, letting in sunlight, which isn’t the same as yesterday; so far, the bedroom’s been dim and quiet when he’s been in here, and he wonders vaguely at the change.

He still feels very small, in his head, but in that in-between state where he usually seems to wake up from naps and sleep. The diaper he’s wearing is still clean and dry. He remembers waking up in the night and crying a little, because his diaper was messy and he didn’t like it, and Auntie Meg calming him down with the soother and changing him and then nursing him back to sleep. That was so nice. He smacks his lips a little, remembering it.

Uncle Benny is the one who looks in the open door, though, maybe noticing him moving around, and smiles at him, and Dean smiles back happily.

“There’s my little man, awake at last,” and he comes and puts the crib side down and helps Dean out of the crib.

He takes Dean’s hands and washes them, though, with a funny soap, and the soft foam on his fingers dissolves off in the sink. Dean opens and closes his hands, enjoying the sensation, turning them over, stretching his hands out.

“Nice and slow, we’re going to have you come back up to being grown up again,” Uncle Benny says gently. “You can take your time and go at your own pace. Let’s start with having you brush your teeth, okay?”

Dean nods, mind all a-kilter, simultaneously excited and sad and a little worried and pleased. He feels so well rested, but last night especially he’d started to get a restless kind of itch in his skin, the inactivity grating on him maybe, he realizes slowly now, as he brushes his teeth with hands that mostly follow his directions, and washes his own face, and then follows Uncle Benny--no, maybe just Benny now?--to the small kitchen area.

Auntie Meg is there, and it smells like she’s making eggs. Dean loves eggs all of the time, big or little, so that’s good. Instead of the high chair, though, Uncle Benny pulls out just a regular, normal, big person chair, though there’s a cushion on the floor next to him, too.

“Your choice, honey,” Aunt Meg says over her shoulder with a smile. “You can sit at the table with us, or Benny will feed you. Whatever’s the most comfortable.”

He actually has to think about it for a moment, but settles into the chair eventually, blinking to orient himself.

He sits quietly and lets his brain be fuzzy while Benny gets glasses and cups and Meg puts eggs and toast on plates.

“No coffee?” he rouses himself to ask, when he realizes his cup has milk. Benny grins at him.

“Let’s get you back to grownup food a little more slowly than that. Maybe with lunch.”

“Ugh,” Dean says. He’s missed coffee.

“How you feeling?” Benny asks, sitting next to him, as Meg brings the plates.

“Kind of off balance,” Dean admits, still raw and honest like he can’t remember before. “Like I got a lot of sleep, though.”

“It’s almost ten in the morning,” Meg notes, putting a fork by his plate. “We let you sleep in.”

“Oh my god,” he says, with dawning joy. “I finally got to sleep in on a morning here!” He grins at them both, feeling alertness flood back into him. “I mean, it’s not super late, but that’s like two hours longer than normal!”

Meg laughs. “Special treat,” she tells him, and then they’re all eating the eggs before they can go cold, because nobody likes cold eggs.

He lets little memories run through his mind as he eats, testing them like a sore tooth, but he can’t quite feel bad about anything. All the memories are too soft and warm. Auntie Meg, when he was frustrated with his clumsy hands, holding a cup for him and kissing his face until he was laughing. Uncle Benny, holding Dean on his lap in the big chair, reading an amazing story about a girl who ran away to train dragons. Nursing, which makes his sub brain quiver and go soft and gooey and blissful even thinking about it. Even the diaper...no, he’s not even cringing away from that. It was okay. He used it and got changed and got so much praise and treats and sometimes got to come. It wasn’t nasty or even difficult, it just happened.

By the time they’re done eating, Dean feels almost all the way back to normal.

“Can I, can I help?” he offers, seeing Benny start to clear the table.

“Nope, you just relax. We’ll sit and talk on the couch in just a minute, now it looks like you’re pretty grown up again.”

Dean nods. He’s a little sad about that, but his arms and legs are almost aching with the need to move, and run, and stretch.

“Come on, sugar baby,” Meg pets his arm, guides him to the couch, and sits with him, cuddling him close.

“I thought--” he’d assumed that was only for little Dean, the hugs and stuff. He’s been trying not to think about it.

“You’re still...waking up, for lack of a better term,” Meg tells him, smiling as Benny pulls the chair over and sits close. “And anyway, I think you’re pretty great, small or big, and I like having you close, when you’re behaving.” She tweaks his nose gently.

He fidgets with his hands, pleased, and leans against her, enjoying the warmth and closeness, delighted he didn’t lose it after all. He’s always been friendly with Benny, but this new bond with Meg is sweet and fresh and he likes it a lot.

“First of all, we want to tell you how pleased we are with what a good boy you’ve been here, for us,” Benny says seriously, and Dean practically squirms at the words. “I’ve been speaking with Castiel every evening, and he is so proud of you, Dean, and so are we.”

Meg nods. “You were amazing,” she praises him, and Dean’s face is going to catch on fire, he can tell. He doesn’t know where to look. Praise is so hard, it makes him feel so good, but he doesn’t quite know what to do with it, how to accept it, so he just grins helplessly and looks down at his knees.

“I want you to try to tell us how you’re feeling about the diaper, cher,” Benny says, seriously. “Things are going to change just a little bit when we go back into the rest of the house. It’s not as quiet, it’s not just us, so before we do that, we want to check in.”

Dean shakes his head a little. If they’d asked him this three days ago, he probably would have given a half-answer, or tried to make a joke, or something. But he feels different now. He wants to open up and tell them. God, is this what trust feels like?

“I...I still don’t like it,” he starts, hesitantly, glancing between them. They’re listening calmly. “I dunno why. You know I get hard sometimes, using it. And it makes me feel really...not small, little, like a baby. But small, Submissive. When I’m wearing it. Especially when it’s wet or um. Dirty. And when you’re changing it.” Words are hard. That’s not exactly it, but it’s close.

“Okay. And you don’t like that?” Meg presses a little. Dean huffs.

“It’s just all the time. It...doesn’t stop? It’s not like when I’m getting spanked, or sex, when it ends, you know, it’s done. Wearing these just keeps going.” He’s not sure he’s explaining it well, the way the diapers keep him constantly feeling just a little off-balance, his sub brain simultaneously excited and nervous and embarrassed and aroused.

Meg nods thoughtfully, and sits back. “But you’re not angry or scared anymore about it, right?” Dean scowls reflexively at her.

“I wasn’t scared.” Benny just looks at him. “Okay, whatever. I guess not. I’m used to it?” And now when he thinks about it he can almost anticipate the praise, the attention, the soft hands between his legs. He even feels a little spark of extra excitement when he thinks of the way the wet diaper feels, geez, what the hell.

“Okay.” Meg hugs him closer. “That’s really good. I’m glad.”

“Do you think you’ll be able to mess your diaper on your own, or do I need to do another injection?” Benny asks it gently. The second incontinence injection had been a struggle. Dean had had a tantrum, and had been spanked after. He goes bright red.

“I don’t need!--” he breaks off and really thinks about it. About not needing to fight it, about not having that shaky-kneed feeling after consciously using the diaper. But maybe it’ll be easier now. And it was just too strange, having no control of his bowels. “I think I can do it,” he says, more moderately, and they smile at him, looking really pleased for some reason.

“That’s excellent. If you can make the choice yourself, it’s a lot more meaningful than just having no control at all. Okay. Just a few more things, and we’ll head upstairs, then. I got this for you,” Meg says, and hands him a little book. He takes it, curious.

“From The Source: A Guide To Breastfeeding For Dominants, Switches, and Submissives,” he reads, and blinks at her.

“About twenty years ago, when some doctor realized lactation could be controlled with an injection, there was a rush of people getting very into breastfeeding and,” she explains. “And then there were a lot of books written about it, of course. This one is the best, nice and short and simple, just gives the basics. We can tell it was a definite yes for you, apart from everything else.”

Dean didn’t even realize it could be apart from ‘everything else.’ He looks at the book, back to her, tries not to die of embarrassment, and gets out a strangled “thanks,” before tucking it down to his side.

“You’ll need to do both sides and for five minutes to get a tally mark,” Benny says gently, and he didn’t even notice that he’s been rubbing and kneading at his own boob. Holy shit. It’s comforting, though, it feels nice, he can’t make himself stop.

“The rules are pretty much the same as before,” Meg continues, mercifully ignoring his confusion. “You wear the diaper and don’t take it off, and you’ll be staying with Benny in his rooms at night until Tuesday when the boss gets back. But hey.” She squeezes him. “If you need a brain-break, or if you’re just wanting a little time out, you can still give our signal. The shots last a week.”

“We’ll just be pumping and discarding it if you don’t drink it,” Benny smiles big and soft. “It’s a beautiful thing, cher, and I’m very glad we’re sharing it with you.”

“Thanks,” he says again, faintly. He won’t ask, of course he won’t. It was one thing here, with the age play, that makes sense, it all fits. It would definitely be too weird with different parameters, though.

He grabs the book before they leave the age play suite together, though. Maybe he’ll glance through it when he has a break time, or something, and it was super nice for Meg to get it for him, no matter what.

He tries to hide behind Benny when they run into Cole in the hallway outside the dining room, and Benny just reaches back and fishes him out.

“Good to see you, man,” Cole says, in that laconic way he has. “Missed our run today but I’m working out at two if you wanna join.” He nods at Benny and Meg and keeps walking.

“Not so terrible?” Meg suggests. “I can run with you now, if you’d like. I’d love to stretch my legs.”

“Can I take the diaper off?” He’s hopeful.

“Absolutely not,” she raises her eyebrows at him.

“But I hate running in it! I’m not gonna use it!” He throws his hands up in the air. “It’s stupid and pointless!”

“Okay,” Benny says, firmly, and walks him directly into the study, sitting him down on the couch, sitting right next to him. “Maybe you could show me where in the guidebook it says that Submission is always going to be sexy and fun and comfortable. Because I missed that page.”

Dean looks down, feeling sulky. “It’s just ridiculous to have to run in this thing,” he insists, with maybe a little less force.

“You beat Sam when we ran last time,” Meg points out. “And I know it didn’t chafe or rub at all. You just don’t like it.”

“I don’t like it! Exactly!” He points at her. “And nobody’s going to see it or care!”

“You’ll know, and we will know.” Benny leans over him, suddenly, takes both his hands, presses them against the couch. “Obedience for its own sake, Dean. Submission. Accepting someone else’s will. It might not always be your favorite thing, but put yourself in the mindset where you’re submitting, being good, and let that help you. It will make things much easier.”

“It’s always that,” Dean says, a little bitterly, and Benny shakes him, startling him.

“Castiel isn’t your contracted Dominant, right now, but did you know that cross-dressing isn’t on his list of fetishes anywhere?” Shocked, Dean looks into Benny’s eyes, and finds only truth there. What? But Sir had...he has all his pretty things... “That’s right. Part of it is training, but part of training is learning that any good Submissive and Dominant dynamic is about give and take. You will probably give more, because of your orientation and your role, but a good Dominant will make sure that many of the things you give will fulfill you. You might not enjoy them all the time, but they will benefit you. Bratting because you aren’t excited about being obedient to your rules isn’t cute, and I think that’s enough of it.”

Benny’s stern steely tone has Dean biting his lip and sitting up straight and nodding carefully.

“Yes, Benny.”

“That’s better.” Benny lets go of him.

Chastened, at least a little, Dean rubs his wrists. “Geez, your hands are like bricks.”

“Keep that in mind before your bottom feels them,” Benny suggests, still a little stern, and Dean nods, but grins at him.

“I will definitely keep it in mind.” He looks up at Meg, a little apologetic. “Sorry. I’d like to run. I really would.”

“Okay.” She claps her hands. “Let’s go.”

***

Benny and Crowley take him through all of his positions, one after the other, so fast that it’s almost like dancing, that afternoon. He’s sweating a little by the time he’s done, but even Crowley’s usually-sour mug is looking pleased, and Dean puffs up some at that. The itchy gotta-move feeling is nearly gone, too, he feels stretched out and almost tired, after the long run and now this. He almost manages to forget the dumb diaper the whole time, too. But by the time he’s done, breakfast and lunch are catching up with him; he guesses biology is biology, and he knows he can’t work out with Cole later without...going, first. Weights and sparring, for an hour and a half? He’d rupture something if he tried.

He’s determined not to ask for help. It’s pretty easy to let go and pee, now. He gets kind of excited about it, even, knowing it’ll feel good, that everything that comes after is great. It had already felt good before, and now it’s like his body remembers all the great stuff from the age play room every time he even thinks about it, and perks up. Now it’s doing the same thing. So when he waits until Crowley’s gone and steps close and kind of nudges against Benny where he’s wiping down one of the benches, maybe Benny can read his mind or something, because he just puts his arm around Dean and stands there supportively and lets Dean put his forehead against his shoulder and lean in.

His dumb body must have gone through a dozen diaper changes in the age play room, he can’t really remember, but it was a lot. Either way it’s scary-easy to let go and push and his body just does the rest like it’s used to this now. He can feel it, the diaper gets hot and heavy, and it feels good to do it, and embarrassing, and his knees get a little watery, just like every time before. His sub brain is soft and excited and proud of himself and doesn’t care at all that Dean’s face is all red even though he can hear Benny’s voice saying really nice things to him.

“Hey, come here, cher.” Benny sets them down on the bench right there, Dean facing away from him in his lap, back against his chest. Dean squirms a little, but Benny’s arms are big, and snug around his waist, and he’s nervous of struggling too hard with a...with a full diaper, there, he can admit it. Just another thing about this.

Dean’s mid-squirm when Benny’s big hand palms his belly, then pushes gently right into the front of the diaper. He freezes, he doesn’t know what to do, and then the hand is right there on his chubby cock, big and warm, squeezing him.

“Benny,” he whispers, breathy, he doesn’t even know himself if it’s a protest or begging or what. His body’s on board, though, he gets hard so fast it’s amazing, pushing against Benny’s fist. In the last four days his dick’s been played with more by other people than maybe in his whole life before this put together, but he’s still on a hair trigger, he can already feel orgasm coiling at the base of his cock, in his ass, at the small of his back, all the spots where his Angel glands are. But he hasn’t been changed yet, he’s not clean, what if...

“That’s right, little brother,” Benny sounds all warm and amused, sweet, pleased. “That was so good, Dean. You let go and did it all by yourself, I’m so proud of you. You definitely earned a reward. Just let yourself feel good. It was so sexy, honey, so good to see.” The way his pelvis is thrusting up against Dean in his lap doesn’t leave anything to the imagination, even though Dean can’t feel anything through the diaper.

Something snaps into place in Dean’s head, then, in his sub brain and his regular brain, feeling Benny’s hand on his cock inside his diaper, his arousal, his approval so evident. This is pleasing the Dominant, this is arousing him, it truly isn’t just for age play or punishment or to make Dean learn something about Submission. Benny really does want this, and maybe others do too, and maybe it’s okay. He lets his head fall back on Benny’s shoulder with a sigh as he goes lax, he stops trying to hold himself up off Benny’s lap, he lets it all go at least for the moment.

Good, Dean,” Benny’s Dominant voice rumbles right down to his bones, and it lights up his brain and Benny’s hand twists and pulls and Dean comes, whining high in his throat, his hands grabbing at Benny’s forearms and clinging tightly. Spasm after spasm, Benny works him through it, rubbing and stroking and pulling, until he’s too sensitive and starts pressing back into the big body behind him, away from those insistent fingers.

“That’s right, good boy,” Benny hums in his ear, his other hand flat on Dean’s belly, holding him close and firm. His hips are rubbing up faster now, as if with now that Dean has come he can focus better. Without the distraction of pleasure and arousal and chasing his orgasm, it feels so weird, squishy and vague, he can’t even really tell that Benny’s hard, through the padding and the mess. Which, oh, god, he can feel it, the embarrassment of it twinging through him, turning his face scarlet, weirdly making him go even more relaxed, let Benny do what he wants without protesting. There are tears on his face that he doesn’t remember shedding, but they’re not bad, not exactly.

Benny jacks his hips up hard once, twice, three times, and then he’s biting gently on the back of Dean’s neck and groaning at the same time, the good feelings are flooding through Dean and pride and accomplishment and he hears himself moaning too, even though his so-sensitive cock is still soft in Benny’s hand.

“That’s very good, Dean. Good boy,” Benny’s voice is deep and rich with pleasure and Dean’s dizzy with the praise, the shame, the pleasure, all tangled up into a big warm mess in his head. It’s easier to just lean back against Benny and let himself be petted and hear nice things, so Dean does that.

“Let’s get you cleaned up,” and he’s shifted, turned, laid down on his back right there on the bench they were sitting on.

“Gonna have to clean this bench again, Benny,” he points out blurrily, going easily enough.

“Small price to pay, cher,” Benny informs him. He’s got the ever-present bag right there with him and Dean bits back a pleased smile to see his face, how relaxed and pleasured he looks, around his eyes especialy.

“That was really good?” he asks hesitantly, as he obediently spreads his legs, lifts his knees in the now-familiar changing ritual.

“Very, very good,” he can tell Benny isn’t kidding, the firmness of his voice, and all the evidence, too. “Relax, sugar, you’re really messy, you’ve got come and poop to clean up this time. Just lay back and let me take care of everything,” he strokes Dean’s belly as he tucks the top of the used diaper under Dean’s hips, and Dean feels like he should be wildly embarrassed and freaked out by this, but he just can’t get there. He’s too relaxed and all the parts of him are in agreement that that felt really good, that end part.

“You should’ve waited till after this,” he does tease Benny a little, as he realizes how long it’s taking with the wipes.

“That would have ruined the fun,” Benny twinkles a smile at him, urges his hips up, gets a fresh wipe, keeps stroking it over his skin and making him fresh and clean. “For my own Submissives, I have a diaper with a resealing hole between the legs, so I can fuck them after they’ve used the diaper one way or the other, without ever taking it off. But this was its own kind of good.”

Dean’s mouth drops open and he blinks down his body, brain struggling to turn that over. But, but, the expected disgust, recoil, it isn’t there.

“Isn’t that so messy?” He asks curiously. Benny laughs as he rubs powder all over Dean, gently between his legs, it feels so nice and soft and silky.

“That’s half the point. Here, lift up.” A dry diaper goes on, snug, kind of comfortable actually, and then Benny’s pulling his hands, sitting him up, right into his arms. “How you feeling, honey?”

Dean thinks about it. “Messy,” he finally decides on. Benny chuckles.

“Well, you’re clean enough, now. You’ve got about half an hour before Cole comes and fetches you. How about you just sit with me, once I’m done cleaning up?”

Dean nods. That does sound nice. And he’s still all soft and fuzzy in his head, and Benny’s so big and strong and firm, and once they’re sitting together in the big armchair, it is nice.

***

The next day, Dean wakes up in Benny’s bed, and all he can think is that tomorrow, Sir is coming home. He goes on his run and eats breakfast and almost falls into a doze when Ash tries out Shibari on him--oh my god, Dean is so bored, all those knots, what is even the point, and Benny makes a note for Sir with a little sigh and Ash tries not to look offended when he has to wake Dean up--but the whole time he’s thinking that Sir is coming home tomorrow.

“You’re as fidgety as a cat at the veterinarian,” Meg scolds him, as they’re leaving lunch, with a small smile. “Too bad you’re going to have to sit with us for an hour or two while we go over some house accounts.”

“Awwwww,” Dean groans dramatically.

“It’s a truly tragic life you lead, cher,” Benny chimes in, heartless. “It’ll do you some good to kneel for a while and settle down, anyway. You can read, if you like.”

“Oh, my book,” Dean brightens up a little.

“Go ahead and get it, it’s in the study,” Meg nods, and he grabs it in a flash and is back to them. He’d read the first couple of pages, and gotten interested, but he’d been too tired after all the exercise yesterday to really concentrate.

It’s divided up into sections, for Doms and Subs, but Dean’s reading the whole thing through, because why not. And there’s a bunch of interesting stuff in there about brain chemicals and things that Sam is bound to go nuts for, Dean will totally have to lend him this book. Apparently breastfeeding releases tons of oxytocin, which is some kind of bonding chemical, no matter who is...having the milk. Feeling himself flush, Dean rubs his boob, absently. He can’t really picture Sir feeding him, not like Benny did. Anyway, in Subs, there’s a big spike in Rewardarin if you’re nursing, and Doms get both Sationin and Serotonin, so no wonder Meg and Benny were into him sucking on their nipples.

He flips the page and keeps reading, and gets down about half the page, and feels himself go hot all over. He stops, and scenes flash through his mind. Then that conversation with Sam, right before he left.

Feeling shaky and kind of wild, he stands up, book clenched in his hand, and stares at Benny and Meg where they’re at the desk, writing in notebooks.

“You,” he chokes out, and they look up and stare at him. “You’re conditioning me. You, you--” he runs out of words.

Benny closes his notebook and looks at him, but he doesn’t look sorry or guilty, there’s just a little puzzled line between his eyebrows. “Dean, what is this? Of course we are, what do you think Sub training is for?”

He reels. He holds the book up, he has to charge on, he can deal with that later. “The book says, it says breastfeeding a Sub can be a good reward trigger for conditioning out resistance and encouraging desired behavior...for accepting kinks...you used it, you used what I like against me, you didn’t tell me,” he is remembering all the soft sweet touches, the rewards, the orgasms, every time he used the diaper, even the age play itself all soft and warm.

“Honey, we did, we told you we wanted to associate the diapers with good feelings and good experiences,” Meg looks concerned, but it’s directed at him. Oh fuck, he remembers, they had said that. And he hadn’t known, hadn’t realized, even after talking about conditioning with her and Sam. He’s so stupid. Humiliation washes through him in a sick wave, just as she says, “why don’t you calm down and come sit, we can--”

“Don’t you tell me to calm down, bitch!” He throws the book at her.

Then claps his hand over his mouth and takes a sharp, horrified step back.

The ruffling pages of the book as it settles on the floor are the only sounds in the room for a long, deadly moment.

The longer Benny and Meg sit, just looking at him, their faces hard, the more the guilt and remorse shove the anger aside, inside Dean. He shivers with it, almost nauseated. Oh fuck, oh that was so bad, that was incredibly disrespectful, so far across every line. Even if she wasn’t his Dominant at the moment, that would have been really bad.

“I’m sorry,” he gets out, still behind his hand, around a too-thick tongue, his eyes hot and scratchy. “Please. I’m sorry.”

“I will fetch the belt,” Benny says flatly, and gets up.

A wash of terror goes through Dean. “No,” he begs, and tries to catch at Benny’s arm as he passes, only to be shaken off, “Benny no please, not that, please,” and then he’s gone and Dean is crying, standing in the middle of the room, with Meg still just looking at him.

“I don’t punish Submissives when I’m angry,” she says, almost pleasantly. “We will wait for Benny to return, and see where we are. Fetch the switch, bring it here. Now.”

He jumps to obey, taking the switch with shaking hands, kneeling in front of her to give it over, because that feels right. He looks at her feet, in the combat boots she likes to wear, his mind a sick whirl of misery, remorse, failure, wrongdoing, and worse, having hurt someone he genuinely likes and respects.

She takes the switch.

“Tell me why you’re being punished,” she demands, still in that calm voice.

“Because I, I called you a bitch,” he says, miserable.

“Try again.” He looks up, startled. She doesn’t look at all forgiving, so he stares at her shoes some more. Wracks his aching brain.

“I got angry and yelled?” he tried.

“Both of these are part of it. Keep going,” she demands.

“I, I,” he hiccups a sob. His face is already wet. “I assumed the worst thing, without checking with you?”

“Closer,” she says, and then she’s tipping his chin up with one hand. She looks blurry through the tears. “You flew off the handle, and attacked us, without a single pause to think, consider, ask, or give respect. You used language that will never, ever be acceptable. Most of all, you demonstrated yet again that you do not trust us to not harm you, to have your best interests at heart, and though that lack of faith is your own business, the way you expressed it is juvenile, disrespectful, cruel, and ignorant.”

He’s being scolded, and every word is hitting him right in the chest. It hurts, he earned it, but he’d almost rather be getting whipped. The tears are falling now.

“You let your anger carry you away. You did not listen when we tried to intervene. You threw something at your Dominants.” She goes on, relentless, and he’s whimpering now. “That is bad Dean. I am terribly disappointed.” He cries out a little at that. When she slaps his face, sharply, with the hand that had been lifting his chin, it’s a relief, though it’s shocking, too. “Don’t you ever, ever use that language again, do you understand?” She slaps him again, the other cheek, rocking his head.

“Yes ma’am.” he gets out, watery. His cheeks are burning.

“Will you go first, or will I?” Benny’s grave voice is behind him, and Dean doesn’t even know how long he’s been there, he’s been so focused on Ma’am.

“You first, I believe.” Meg stands, and Dean catches his own hands before they grab her ankles and cling. He refuses to scream and beg for Benny not to punish him, he’s earned it, he knows that but he’s scared, he remembers the last time, the scorching agony of the belt against his ass.

“Up, Dean. Bend over the couch,” Benny orders. Dean stands up, legs wobbly, and makes it three steps, before his sub brain takes over and tough Dean Winchester, veteran of hunts and fights and brawls, is washed away.

“Please Benny no,” he wails, turning desperately to the big man, “I’m sorry, I’m so sorry!”

“On the couch,” Benny puts a hand on his shoulder and turns him back and “NO!” Dean keens, but Benny moves him, and then he’s being put down over the couch, belly to the cushions, butt high in the air. Benny yanks the diaper right off him, down to his ankles.

“I do not enjoy this,” Benny says coolly, one hand firmly on his butt. “But I will punish Submissives who have earned punishment. I am not going to use the paddle or the cane on you today, which you have more than earned, considering your bruising is not gone, and there will be two of us. And once you have been punished, you will be forgiven.”

“No no no,” Dean babbles, trying to turn over, shield his bottom, just instinct, his mind staticky with fear. Benny just ruthlessly flips him back. Deep down he knows he needs to atone, that until this happens everything will be wrong and awful and sick and bad in his heart and mind, but he’s scared and he doesn’t want it.

“I’m not going to start until you’ve calmed down,” Benny tells him, quiet but firm, his hand still there. “Take a deep breath.”

The order, so familiar, settles Dean down some. It’s like he’s standing a little outside himself. He struggles, trying to pull himself back together. He wants to fight and wants to beg and wants to run away all at the same time, but one deep breath and then another does help. He stops shaking so hard, feels a little shame creep in at his hysterical protests. He knows he earned this, he does.

“Better,” Benny allows, and then there’s a hissing sound and the belt comes down. CRACK

Instantly, Dean bows away, twisting, kicking, screaming, the burning stripe agony, flaring all over his skin. “I’m sorry!” he cries, his hands back behind him, shielding his bottom. Benny takes them both and holds his wrists together in the small of his back without a word, and then starts laying into him. The belt comes down fast this time, smacking down from the top of his ass all the way to the top of his thighs, blurring together so he can’t count them. Every blow gets more tears and then Benny starts again at the top and Dean crumbles, the fight going out of him. He sags, limp, against the couch, sobbing into the fabric.

CRACK the belt lands again, and “I’M SORRY so sorry so sorry” it’s a cleansing litany, the words all he knows in this blank place of penance.

No more come, and there’s a gentle hand on his back, patting him. His wrists are released, his arms just drop down to his sides, he’s out of strength to hold them.

“Good, Dean. I forgive you,” Benny says, quietly, warmly. It’s balm to his ears.

“Five on your ass, five on your hole,” Meg’s voice, and he nods against the couch cushions, dizzy. Please, just let it be done, let it be over soon, he wants to be forgiven.

No one asks him to hold himself open. Benny maybe does it. The switch on his hole is sharp, fiery, not like the belt, so much more needling and fierce and he’s trying to climb the couch away from it, but hands aren’t letting him. Then another one and another and another, he’s screaming into the cushions, and one more. Meg is fast at least and he is starting to feel better under the pain, light and floating, washed clean.

“Almost done, Dean.” Benny leans on him, and he doesn’t understand it until the switch lands on his bottom, where the belt has already left the skin hot and red and angry.

He can’t move, he can't escape no matter how hard he tries, his butt is screaming burning fire at him with every stroke, he just has to take it. Endure. He thrashes hard, he can’t help it, and when the final switch lands, it snaps through him like victory, it’s over, he’s paid, the relief is like an orgasm, rippling through his whole body.

“Very good, good boy,” Meg murmurs to him. He can’t move, his ass feels huge, raw, throbbing, so he just stays where he is, face mashed against the couch in a spot wet with tears and snot and spit. His ears are ringing but he can feel them moving, feel soft hands on him, and then Meg is urging him to slide up.

Dizzy and disoriented and still crying, he does, carefully. She eases him into her lap, balanced on a hip, and lets him drink sips of water, stroking his face and hair, wiping his tears, while she smiles at him.

“Sorry,” he croaks at her, when his voice feels like it might work again. "I do trust you. I do. I was just embarrassed and it made me mad."

“You’re forgiven. It’s behind us, all’s well,” she says firmly, after a long look into his eyes, and a little nod. He wants to crawl inside her skin, feel it somehow, know viscerally that he’s a good boy, that he’s still in her regard. He feels raw and uncertain and young and exhausted.

Hesitant, hardly daring, his heart pounding too fast, he taps her thigh three times, barely there. Maybe he can pretend it was a mistake if she says no, he thinks hysterically, maybe he can say it never happened...

“Here, sweetheart, of course,” she hums to him. She tugs her sweater over her head, unbuttons her blouse just like that. She’s got a clip-front bra that she just unclips and pushes aside, and Dean stares shamelessly. Her breasts are heavy-looking, he can see blue veins, and her nipples are standing up already. She lifts one in her palm, urging him closer, offering it to his lips.

With a little sigh, his mind almost hiccuping with relief, he takes it in, mouth pulling in the nipple and part of her breast, too. The first taste is soothing heat against his tongue, his rough throat, then he’s pushing closer, sucking harder, and the flow really starts. He barely has to suck at all, just swallow as the milk jets into his mouth. Looking up, she’s smiling soft and warm down at his face, and that’s so good too. Everything eases, he can breathe nice and calm again, his thoughts slow down, his body relaxes. It’s okay, he’s good, he’s forgiven, he can feel it now.

He nurses through Benny putting cooling cream on his ass, and Meg and Benny talking quietly over his head. He’s drifting in sensation, he can’t be bothered to pay attention. She moves him to the other breast effortlessly, and he closes his eyes, letting himself float. He knows they’re going to make him talk about what he read in the book, probably. And there’s stuff to do today, and to get ready for Sir coming home tomorrow. But right now he’s content to be still and quiet, and rest.

Chapter Text

Castiel has been keeping track of Dean’s progress, and everything else going on at the house since he’s been gone, with nightly phone calls to Meg and Benny. He knows that water pipes broke in the second guest house, that Dean earned two strict punishments and how they went, that Claudia is out sick again, even that Dean has a strong lactation kink that no one suspected before. But as he drives around the corner and sees the entrance to the long drive ahead, he knows that seeing them, seeing home, is completely different than just knowing those things. He speeds up and is a little amused at himself for doing so.

He hopes Benny and Meg were able to follow all of his directions for his homecoming.

Crowley is waiting by the door, immaculate in black, as he always is when Castiel returns home from being away, and Castiel sighs in relief as he pulls up and puts the car in park, steps out, stretches luxuriously.

“Thank you, Crowley,” he says politely, “my things are in the trunk.”

“Welcome home, Sir,” the small man says, with a crisp little bow, and Castiel smiles at him. Yes, home, he’s back.

He sheds his coat, his jacket, his tie in the entryway, feeling each layer loosen the binding of outside responsibilities. And when he steps through the door, something settles inside him, clicking into place. There are Meg and Benny, smiling at him, and there is Dean, kneeling on a cushion a little to the side, naked and golden, in a perfect Wait position with his cock caged in gleaming metal on his thighs, looking almost vibrant with excitement. He smiles broadly at them all, and steps to his Dominant employees, hand extended.

“Boss, so good to have you back. I hope the trip went well,” Meg says, warm and welcoming, clasping his hand, going to her tiptoes to give him a kiss on the cheek. Benny shakes his hand and clasps his arm warmly, and Castiel is almost flustered, as always, by their honest affection.

“It did, thank you. And everything is peaceful here? I’m sure it is, of course. I could not have left the place in better hands. And Dean,” he turns to the boy, smiling, stepping to him, warming to his toes at those huge green eyes lift to look at him. Dean shifts and then stills suddenly, and Castiel knows smugly that his requests have indeed been followed.

“Sir,” Dean says, a little breathless, beaming, oh, he’s everything lovely like this. Castiel cups his chin in one hand, a caress. His skin is like warm silk.

“I’ve never had a more pleasant greeting upon homecoming,” he tears himself away from Dean’s eyes and tells them all, the words feeling a little stilted in his mouth, but not less sincere for all that. “Meg, Benny, I relieve you of your responsibility for this establishment and this Submissive. Thank you for your care and guardianship. I could not be more satisfied.”

They don’t give him any platitudes like ‘it was no trouble,’ or ‘it was nothing;’ both are too aware of the great trust it had taken for him to leave them with the house, with Dean, and he knows it, and they know it. They both just smile at him and tip their heads, looking pleased and proud. Dean gives a little sigh, like he’s tasted something good, and blinks slowly, as if he’s relaxing right there in the front hall.

“Angelique is doing your favorites for lunch in a couple of hours,” Benny tells him, “to celebrate you getting back. Dean’s already had his run and his enema this morning, too.”

“And the stimulator is in,” Meg adds, a little wicked smirk on her face. “The big one, just as you requested.”

“In that case, I think Dean and I will adjourn to my office, and find out how it’s working,” Castiel smiles down at Dean, whose face is slowly flushing pink. “Up, with me. Bring your pillow.”

“Yessir,” Dean says instantly, but his rise is much slower and more awkward than that. He teeters like a colt with one leg in front of him, still on one knee, then finally has to use his hands to help get himself upright, trying to move his hips as little as possible. There’s a light sheen of sweat on his face when he’s finally upright with the pillow in his hands.

“Well done,” Castiel praises him. He waves a little to Meg and Benny, and leads the boy away.

Dean’s normal graceful swagger is gone, replaced by a careful, stilted hobble. He freezes, mouth open silently, more than once, and is so focused that he doesn’t say a word the whole time. But they make it eventually, and Castiel settles on his favorite couch, and tugs Dean close, then into his lap, gently, facing him, so Castiel can touch to his heart’s content. His hands feel starved of Dean’s skin.

He finally breaks the silence when Dean settles gingerly onto his thighs.

“There. That is so much better. I missed you terribly, lovely.” It’s only the truth, after all.

“I missed you too,” Dean sounds almost surprised, not by what he’s saying, but that he’s saying it. “So much!” He laughs, then looks down, to where his hands are pressed against Castiel’s chest.

“I’ll tell you all about the Dominant Center soon. I think you’d find it interesting,” Castiel promises. “We had our first inpatient clients this week, after all, and some of the staff are Submissives who remind me a bit of you. But first, tell me about your week. Did you enjoy the training?” He grins at Dean’s conflicted face.

“Um.” Dean starts to squirm, then freezes. “I liked some of it?” He answers carefully. “It was challenging. I, uh, messed up a few times. I was pretty glad to be done this morning.”

“And you’re more comfortable with some of your body functions now?” Castiel prods, gently. He smooths his hands around Dean’s waist, up his shoulders, down to the round perfection of his bottom. Just in the lower curve of the crease, he can feel the metal of the base of the stimulator, and jostles it a little with his finger.

“Ah! Ah owww,” Dean goes rigid, then whooshes out his breath, and nods quickly. “Yeah, I definitely...you can’t not, right? I mean. All things considered. And some of it was good.”

“I got the daily reports, but I’ll get the full notes from Dom Meg and Dom Benny,” Castiel assures him. “I’m so proud of you, Dean. They told me how hard you tried, how good you were.” He watches Dean’s face go soft and pleased, and pulls him close. “Come here. You were with other Dominants for an extended period doing difficult training, and you came through it. That’s very challenging, and you rose to that challenge and did so well. I am so pleased with you.”

“I wasn’t always good,” Dean protests against his shoulder, but he’s pushing close, his arm tight around Castiel’s shoulders, accepting and eagerly returning the embrace.

“Maybe not, but you were punished, you atoned, and moved past your mistakes,” Castiel says against his hair. “That’s what matters.”

“Mmm,” Dean hums assent into his shirt. He can feel the boy going relaxed by degrees, and despite the urgency of his dynamic demanding he re-establish Dominance, the prod of his cock against the inside of his pants, it’s nice to just sit and hold him for a moment like this, reconnect, enjoy the closeness.

He strokes his hands down Dean’s back once more and gently sets him back. Breath hisses through Dean’s teeth with his wince, and Castiel feels himself smile again.

“And how are you finding the stimulator?” he asks, with what he hopes is innocence. “Is it effective in keeping your attention on your manners?”

There’s the glare he’s used to, though it’s half-hearted. It appears the stimulator is doing its job indeed.

“It’s rough,” Dean complains. “It’s itching me, inside. Why did you tell Benny I had to wear it today?”

“Because I have a few things to attend to before I can be with you without distraction,” Castiel tells him easily, “and I very much do not wish to punish you today. And I am looking forward to you being a bit raw and sore when I take you in a little while.” He watches Dean’s eyes dilate to near-black, his breath catch, his body go still, and everything in him purrs. “I have missed much about you, sweetheart,” he murmurs, leaning forward to nip sharply at Dean’s neck. “Your smile, your questions, your incorrigible spirit, and yes, how you scream so beautifully on my cock.”

“Sir,” Dean whispers, and licks his lips, like his mouth has gone dry. “I, um. Imissedittoo,” he mumbles, so quickly that Castiel almost misses it entirely. But he doesn’t, and it feels like the sharpest surge of adrenaline straight to his veins. Oh yes, he will be rough with the boy today, a proper reminder of their dynamic. He reins it in, leans in and kisses Dean’s lips, firm and nearly chaste, and then sets back again.

“Surely Benny and Meg were not so easy on you,” he teases gently, even as his hands cup Dean’s hips and press him down a little against his own thigh, pushing it against the base of the stimulator.

“Hnng...” Dean gulps, then gathers himself. “They were...it was soft. The things, a lot if it, it was difficult, but all soft.”

“Even the punishments?” Still teasing. Dean glowers at him, a weak thing. “I did warn you about Benny’s firm hand, when he’s driven to correction.”

“Those weren’t soft at all. My ass still hurts,” Dean complains, and indeed, there’s a tapestry of old and new bruising decorating the boy’s cheeks. One of the reasons he’s wearing the attention stimulator, in fact; Castiel would prefer the bruises to be older or even gone before he’s punished again.

“So the diaper training was soft, and the punishments were hard. I think I see, now,” Castiel says thoughtfully, knowing he’s still smiling a little.

“I know I’m not saying it right, but it was! It was long, and it never stopped or changed, it just...was. And when we were in the age play room, that was really soft. I liked it okay. But I missed you, I like how it is with you better,” Dean insists, stubbornly.

“I am gratified to hear it,” Castiel answers, suddenly serious. He knows the boy enjoys challenge, adversity, struggle, even needs and craves it in his dynamic. He even needs and craves force, at times, the practical demonstration of Dominant will, something to test his restless energy against. The time with Benny and Meg has clearly allowed Dean himself to realize it, if not in so many words, if only by its absence. “I like how it is with you better, too,” he tells Dean honestly.

“Even though you don’t like dresses?” Dean glances up at him slyly through those ridiculous eyelashes, and Castiel chuckles.

“Ah, they’ve been tattling, I see. No, it’s not one of my particular fetishes. But I enjoy you in dresses, lovely. I like how you are in them, how they affect you, and that is more than enough.”

Light dawns in Dean’s eyes. “Like me, and the diapers, with Benny,” he says, a little amazed. “I mean, I’m okay with them, but I don’t love love them, except in the age play room. But when he was really loving it, I kinda felt like that.”

Castiel nods fondly. It’s also not entirely separate from how Dean reacts to the pain Castiel inflicts on Dean himself, how Dean revels in it despite his body not feeling pleasure, how he fights it and then throws himself into it in total Submission to Castiel’s pleasure, but that is much more intense and visceral, and he doesn’t want to muddy the waters.

“But I’m happy to tell you,” he says, reaching up to cup one of Dean’s small breasts, gratifyingly soft now, and thumb the nipple, “that having a Submissive in milk is a fetish of mine and has always been. So your newfound enjoyment won’t go unfulfilled, should we end up contracted.”

Dean goes pink, then white, then red, looking between Castiel’s hand and his face.

“I, um. They told you. Of course they did! But I wasn’t, Meg and Benny were the ones.” He takes his hands from Castiel’s shoulders and shoves his face into them. “I don’t even like my boobs!” he nearly wails, but it’s about as unconvincing a claim as he’s given Castiel yet.

“Hmmm. I expect that will continue to change,” he muses out loud, and gives Dean’s nipple a last firm tweak.

Dean makes an incoherent noise into his hands, then grabs for him again when Castiel shifts him.

“I’m going to take care of a few urgent things for the house, now, that have been waiting for my return. You, pretty, will kneel here, quietly, and get ready. As soon as I’m finished, I will say hello properly.” He pats Dean’s bottom gently.

“Yessir,” Dean squeaks. He licks his lips again, shifting on his knees on the couch, right where Castiel put him. “Can’t I kneel by you instead?”

Castiel raises his brows in surprise. And pleasure. The floor will be less comfortable, but it will be good to have Dean right by his side.

“Bring a pillow, right next to my chair. Good boy, Dean.” Dean glows with the praise, and hurries as much as he can to obey, easing to his knees as Castiel sits at his desk.

Castiel has never felt less interested in signing checks, marking items paid, and signing off on purchases and requests, but he schools himself to rigid self-discipline, despite the warm head leaning against his thigh, and soldiers through. It also allows him time to shift, settle, from the playful, teasing, affectionate talking they had been doing before to something darker, more intense, more primal. He feels it settle in his King glands, urgent and hot, as he glances down at Dean’s bent head. The boy is being good, quiet and still, breathing evenly. His cock is an angry red in its cage, though, pressed against the metal bars, trying to become erect, and Castiel’s own erection jerks a little at the sight.

He sets aside the last check.

“Up, Dean,” he orders, his voice a growl in his own ears. “Bend over the couch arm, spread yourself.”

With a little gasp, like he’s been taken by surprise, Dean lurches up to his feet, and gets himself to the couch quickly. Bending, spreading, such a good boy.

“Let’s get this out of you, hmm?” Castiel fingers the base of the toy, long and slim, which flares in a smooth anchor-shape up Dean’s crack. Easy to toy and play with, or attach to a collar or belt with the small ring at the top, but for now, it just makes it easier to remove. “Press down,” he instructs, and twists the stimulator so that the prongs are no longer hooked against Dean’s gland and prostate. The roughened neck of the toy swivels in Dean’s hole as well.

“AH!” Dean arches up, hands losing their purchase on his cheeks as they clench.

“Dean!” Castiel slaps one cheek sharply.

“Sorry, sorry,” Dean whimpers, getting his hands back quickly, pulling himself open again, shakily.

“It has left you a bit raw inside,” Castiel notes, not bothering to hide the pleased purr in his voice, hearing Dean’s whimper in response as he works the thing out of him, gently, holding him open with a thumb to ease the prongs out. Dean whimpers again as they pop free, and then groans in relief when he’s finally empty. Castiel prods his thumb at Dean’s hole, watching it twitch and clench, enjoying the angry red of the inner rim.

“Sir,” Dean begs thickly, and Castiel isn’t sure what he’s begging for. He suspects Dean might not know either. He gently stands Dean up and turns him, drinks in his pale face with the spots of bright color high on his cheeks, the wide dark eyes, the way he’s chewing his lip with nerves.

“Let’s have this off,” Castiel thinks out loud, as he unlocks the cock cage, works it loose, sets it aside. The pain has left Dean small and soft, lovely, and he puts a hand on his back and walks him back to the cushion on the floor.

“Present, knees on the pillow. I’ll take you on the floor today,” he decides, loving the pause in Dean’s step, the hitch in his breath.

“Yes sir,” Dean murmurs, automatically, sounding stunned. He settles to his knees, and then slides his body down into Present, and it’s like he takes a deep breath and lets it out, settling, easing, his hips high, chest on the floor, face cradled on his stacked hands. If Castiel can’t get into that perfect ass in the next few minutes, he thinks, he might actually die, so he strips hastily, grabs the lube from the desk, and gives himself a cursory slicking. The remnant he smears on Dean’s crack and hole, watching him jump and shiver.

There’s just enough room on the pillow for his own knees, inside Dean’s, and he grabs the boy’s hipbones in his palms, anticipating Dean’s jumping jerk and gasp when his cock nudges that little red hole.

“Sir,” Dean mutters into his hands, pleading, and his cheeks are clenched reflexively tight as Castiel presses forward again, nudging, seeking, the hot head of his cock finally finding the soft give of his hole and he squeals and scrambles and tries to go flat. Castiel holds him up, pulls him back onto his erection, his cock spearing in, finally, blissfully, hot clenching tightness, Dean’s bitten-off howl as he fully seats himself in one powerful motion.

“SIR!” Dean’s squirming, almost out of his position, one hand under him, back arched, then bowed, hips twisting. “Sir please, too much, I can’t, I can’t...” Castiel growls, and leans over him, a hand on his neck pressing his face back down. “SIR!” he shrieks into the floor as Castiel drags his hips back, then thrusts forward, deep and powerful. Dean’s body clenches hard and tight around him, his whole body rigid, writhing, speared on Castiel’s cock. He does it again, and again, then catches his rhythm, slamming home over and over, exultant pleasure washing through him after so many days of denial to feel this again, to have his boy under his body, so beautiful in his distress.

For long minutes, he just revels in the feeling, the blood-hot glove of Dean’s body, the power and pleasure of it, the sensation of finally coming home in truth. Dean’s struggles firing heat through every nerve, twisting his arousal higher and higher.

Dean’s lost his words, every thrust just knocking a cry out of him, but his legs are restless, trying to hook around Castiel’s, his body keeps trying to twist away, only Castiel’s hands on his hips keeping him in position and still.

“Let go, Dean,” Castiel leans up, blankets him with his body again, bites the words into his shoulders, avoiding the weak hand Dean gropes behind him, reaching to catch at him, push at him. He works his hips, leaving his cock sheathed deep, drinks in Dean’s high, breathless whines and moans. “Give in, baby, I have you.”

“I can’t, I can’t, I forgot, it’s too much, OH, ah ah ah,” Dean arches, teeth clenched, as Castiel bites the back of his neck, then ruts into him hard and fast over and over, pounding him, his body held in a hard arch between teeth and cock, and that does it, he feels it ripple through the body underneath him, faster and more complete than usual, as Dean suddenly goes limp and relaxed and open.

He feels the wetness against his thighs and knees a moment later and shouts his own triumph against Dean’s neck, holding him hard, working his own hips even more furiously. He straightens back up, wanting to see, and Dean’s body is a gorgeous submissive curve, now, hips high and open, thighs easing wider, shoulders soft and low. The tip of his cock is still wet from his submissive wetting, and Castiel moves a hand to the small of his back, rubbing and stroking the dimples there, a thumb pressing just at his tailbone, feeling the hot softness, relaxed muscles, every hole open and offered to him.

“You are amazing,” he purrs, his hips never pausing their brutal rhythm. “You are so good, Dean, so brave, such a wonderful Submissive, I am so pleased, so delighted with you. You have made me so hard, I wish I could fuck you forever, sweetheart. Your body is perfect for me, YOU are perfect.”

He never knows if Dean hears his words when he’s down like this, but his tone definitely gets a reaction, as Dean’s back arches even more, his face turns to the side, his face a gorgeous mix of agony and bliss. He’s still panting out cries, but they’re muted now, without that frantic fighting pained edge, and his eyes are glazed, lost, dreamy. Beautiful.

Castiel wishes he could fuck him like this forever, but it’s been too long, and his stamina is not up to the task. He can feel the orgasm boiling at the base of his spine, and he holds Dean’s hips again, leverage, as he starts working for it in earnest, slamming himself in, then standing without ever pulling out. He crouches over Dean’s hips and goes for it, cock a blur fucking in and out, hips pistoning, angling down for the best friction and tightness and oh, yes, there it is, he groans and clenches his teeth and fills Dean with his seed. The orgasm almost whites him out it’s so powerful, his Dominance and body both utterly satisfied, and he only eases back down to his knees behind Dean when the last aftershock is done.

Dean is still gasping hitching little breaths into his cupped hands, shivering all over lightly, and Castiel pulls out gently, noting the dark redness of his hole. Perhaps some extra lube before bed tonight, he muses, and gently checks for abrasions...there are some minor marks, from the stimulator and the friction, but nothing that will not mend.

“Come here, my good boy,” he murmurs, energized and awake as always after an orgasm, fixated entirely now on the well-being of his Submissive. He eases Dean to his back, and the Sub rolls easily, pliantly, still completely down. “Let’s go to the couch, honey,” he urges, getting Dean stumbling to his feet, then to the couch. There is water on the table, and he tucks Dean into his side, holding him close and quiet, and feeds him sips of it as he strokes his hair, his breasts, his belly, his legs, tells him how good he is, how beautiful, how brave, how obedient and perfect.

Dean is limp, pliable, every warm word seeming to ease him further into Castiel’s hold, his relaxation becoming more and more complete. They sit together quietly for nearly half an hour, small sips of water for Dean, Castiel holding him, petting him, praising him. When Dean finally stirs, it’s a mellow shift, a stretch of his arms only, reaching to hold around Castiel’s waist.

“I’d forgotten how much it hurts, and then, after, how amazing,” he murmurs into Castiel’s lap. Not complaining, just in a wondering kind of way, as if he can’t imagine forgetting such a thing. “I can’t believe I missed this so much. And oh, I did the pee thing again! Oh my god, that was...it felt just as good as I remember.”

Castiel strokes a firm hand from his nape to his tailbone. Considers this calm, pleased reaction with the first time, his horrified cringe. “You did, it made me so happy. You are special, lovely. You are a high-needs Submissive, and you need what you need, and you like what you like. And what fulfills you will not be the same as it would be for someone else. Let me show you something.” Dean peeks up at him, still a little dazed and sleepy and subspace-drunk, and he smiles down at him. “Just let me get my laptop, I’ll be right back.”

With a little disgruntled huff, Dean lets him retrieve his laptop from the desk and return. He has these files ready to hand, they’d been part of Dean’s progress report that he’d prepared for Gabriel before his trip, and he thinks seeing them will be interesting for Dean, too. He finds the first one, and clicks play.

“This is the video of your arrival from the first day,” he says quietly.

On the screen, what is obviously a high-quality security video of the main entryway plays. There’s Castiel himself, looking more or less the same but with a longer haircut. And behind him, hunched resentfully, thin, with all his body hair, is Dean. His face is fixed in an angry scowl. He moves stiffly, almost like he’s in pain, or ill. His ribs are obvious, and he’s pale.

“Holy shit.” Dean leans towards the laptop screen, his own eyes going wide. He watches his past self sneer at Castiel’s back. Then the screen angle flips, and it’s the little medical room, and he’s sitting on the table, watching Sir warily. Sir puts a hand on him and he flinches halfway across the table.

“I was a fuckin’ mess,” he breathes, he can’t look away. It’s kind of fascinating, watching this, even though he can’t hear anything. He watches, appalled, as his past self gets more and more obviously pissed off when Sir isn’t doing anything more than touching his belly and shoulders, and then actually tries to throw him off, and Sir just stays calm and keeps going steadily. When the Dean-on-the-screen finally, stiffly, lies down on the table, and Sir rubs his Angel glands and that old Dean has what looks like a little seizure, Dean blows out a breath he hadn’t known he was holding. Honestly, a lot of those early days are kind of a blur of anger and panic and frustration. But wow. If he acted like that now...he hides a wince of reflected embarrassment.

“Do you see how much things have changed?” Sir is watching, too, still with Dean mostly in his lap, all warm and strong. “You’re so much more powerful now. So much healthier, stronger, more sure of yourself. Here, look.” He sets the laptop aside, and with that memory fresh in Dean’s mind, gently urges the boy to his feet, over to the mirror by the door. He stands him there, and stands behind him, hands on his hips.

The contrast could not be more stark. This Dean stands proudly tall, muscled, golden with sun and exercise. He’s easy in his skin, and moves with confident grace. Dean meets his own eyes in the mirror, then Castiel’s, then flushes and looks away.

“I see it,” he mutters. “Okay.”

“So you can believe you missed the things you need, that you crave,” Castiel prompts gently, sliding a hand around him to cup his soft penis.

“Yeah,” Dean breathes, and leans back into Castiel, watching them in the mirror, face wondering and soft. “Yeah, I guess so.”

***

To: ALL
From: GarrisonBoss
Subject: Conversation with Dean

To all staff-
As you know, I have given serious consideration to offering Dean a long-term or perhaps permanent contract after his training is complete. Matters are proceeding in this vein, and in order for them to continue, the supernatural and non-human nature of myself and some of the staff here at Novak House must be revealed, so as not to be deceptive and to allow Dean to understand the truth of the group he would be joining.

I have spoken to each of the supernatural staff individually and obtained their consent to reveal their natures, or not, in a few cases. However, it is uncertain exactly what Dean’s reaction may be. Though we may of course hope for the best, we must all remember that the safety of staff and employees is of first concern, and that Dean is a trained Hunter, and related to Hunters. Given that, please note the following:

- Cole has removed Dean’s personal possessions, including all weapons, to an offsite location, at least temporarily.
- All supernatural staff are required to report to my office sometime this afternoon or evening to check on individual protection and concealment sigils.
- As Claudia is at home for her monthly time away, extra security has been placed on her home.
- Please take all caution with your safety. You are of course entirely safe within this house. However, trips off-property should be undertaken with company and caution until we are assured of a good reaction.

The plan is to inform Dean tomorrow in a controlled environment. We do expect some disruption to the normal daily schedule. Please go to Meg with any questions or concerns during the day. As always, thank you for your untiring work, excellence, and energy.

Best,
Castiel

“Well, here we go,” Meg says, with a kind of cheerful fatalism. She props her boots up on the desk of the security office, regarding Cole and Benny past their toes. “It was nice knowing you boys.”

“He has to tell him,” Benny protests. “And soon. It gets worse the longer he waits, cherie, you know it.”

Cole just eyeballs her, then looks back at the email they’ve all just read.

“You two are human,” she points out. “It’s all well and good for you.”

“So you didn’t give Castiel the okay?” Benny looks curious, not judgmental, so she sighs, and shakes her head.

“No, I did. I figure, if he’s going to come clean, I want to clear the deck, too. It doesn’t feel right, keeping something so big from him, not if he’s going to be staying around. And I hope he does, I really do. But that kid has trust issues bigger than this state of Texas, and he doesn’t exactly react rationally when he thinks that trust’s been violated. I don’t see any way this goes well, no matter what the boss hopes.”

Benny pulls a frown, then rubs his face. “Yeah,” he agrees. He sounds reluctant. “Yeah, I can see it.”

Cole sits back in his chair. “The stilettos are out of state,” he offers suddenly, startling both of them.

They nod their thanks to him.

Chapter Text

Stiff, curled against the footboard, his eyes burning but unable to close in sleep, Dean stares into the darkness of the bedroom. He cannot relax. He can’t even convince himself to rest. He can’t stop the conversation that Sir--Novak--had had with him earlier from playing over and over in his head.

It had started so innocently. Sir had taken him to one of the training rooms, after a great morning together. He’d put arm bindings and leg binding on Dean, and then asked Dean about whether he’d ever worked with friendly supernaturals.

Dean honestly hadn’t been able to remember details, if they had. Maybe, once or twice, but if so it hadn’t really stuck out to him. And then Sir had started describing the way this house had been built, with friendly magics. Protecting the inhabitants, so they could live in peace and safety, and Dean had been fascinated, sure. Until Novak had turned, and looking more serious than Dean had maybe ever seen him, had told him WHY the house was built that way. Because, he’d said, he was only mostly human. Like some of his staff, and all of his family. And that he’d had to tell Dean before things between them had gone any further. That so many of them were supernaturals, but that all of them were peaceful, nonviolent. That he wanted Dean to understand, to ask questions, to say anything he needed to without restriction. But that Dean was safe here, that no one meant him or any other human being harm.

Dean remembers going cold all over, then, but holding it together. Asking what Castiel was. And laughing a little in relief when Castiel said, “an Angel of the Lord,” because John had always taught them that angels don’t exist. This was a funny joke, or a prank, or a test, right? And then...then it happened. The great creeping black shadows behind Novak’s shoulders, wing-shaped, mind-bendingly impossible, the glowing white eyes, the prickle of electric power in the room. He flinches on the bed at the memory.

He remembers rolling off the positioning stand and to the floor, getting himself distance, muscling himself into a crouch, the cold calm clarity of it. Remembers asking Novak who else in the house had powers, was inhuman, and shuddering at the list. Meg, demon. Angelique, shifter. Claudia, were. Remembers the shock of the names hitting him, sinking into him. Remembers the nausea, turning his head so he could vomit on the floor, Novak rushing to his side to move him from the mess and him crab-scrambling away.

Remembers the anger. Shouting at Novak, cursing. The feeling of something in his chest breaking, the pain of betrayal. John has taught his sons, all his life, that nonhumans are not to be trusted. Not ever. Dean knows it to be true. His dad’s a great hunter, a great man. And at the same time, he’s lived in this house for two and a half months now. He knows these people. Now that that first blast of fear and anger and shock is past, he can remember Angelique making his favorite sticky pastries, and Meg and her no-nonsense affection, Claudia and her gentle kindness, always, and Castiel--Sir....

He shakes his head and stares burning-eyed into the dark. Novak had reached him eventually, had cleaned him up, had moved him back to the stand, but hadn’t done anything else. Just sat on a chair, looking human and tired, and waited with Dean. For like two hours. Dean had thrown a couple of banishment spells, just simple ones he could remember without a book, but Novak had told him that the house was warded against any kind of dangerous magics. And that you can’t banish an angel anyway.

Dean hadn’t fought his bindings. He’s smarter than that. He’d cursed Novak out, coldly and at length, called him a liar and a cheat and a faking bastard, and it had made him feel a little better. But he’s outnumbered, outgunned, here. And maybe, maybe they’re not a threat to him, he gets that. He’s been here for months, nobody’s hurt him, not like that. But the hunter part of him is screaming about the danger. There are demons and shifters right here in this house. So when he finally calmed down, and Novak brought him back out in the house, his whole focus was on getting to a phone.

Maybe it’s good they think he never calls for help. Maybe he didn’t put up as much of a fight as they were expecting. He was able to dial out from the office phone while kneeling by Novak’s desk in his study, mutter a quick message to the voicemail on the other end, and hang the handset back up, before anyone even looked his way. Maybe they shouldn’t have bound his hands in front of him. He won’t look at or speak to any of them, anyway. Not to ask for something, not to reply to a question, he has gone frozen, with heat or cold inside, he can’t tell.

He remembers Benny (Benny’s human, Dean thinks, thank God, unless they’re still lying) saying something to Novak, after Dean had knelt in silence through dinner, and he’d sounded upset. Something about distress. Novak had answered quietly, but Dean’s not really paying attention.

Novak had given him the option of sleeping on the couch or at the foot of the bed in their room. To make him more comfortable, he’d said, not as a punishment, but if he was on the couch, he would need to be bound, to ensure his own safety and the safety of the staff. Dean had barely been able to hold back a bitter laugh. What danger did he possibly present, naked and unarmed and without so much as a casting book against demons? But he’d nodded at the bed anyway, uneasy at the thought of being helpless in the dark.

No paddles, nothing but bathroom and then bed, and Novak’s quiet voice in the night, promising tomorrow would be easier. More lies. And now Dean lies here, thoughts flying wildly back through every interaction he’s had in the house trying to find signs he’d missed, fear and hurt and anger and betrayal running through him in waves, throat thick with questions and words unsaid, the core of him still cold and hard, brittle and sharp.

He’s in some kind of strange exhausted half-daze when quiet footsteps outside the door snap him to alertness. Novak’s asleep, but also wakes instantly when the door opens. It’s Benny, he can see the silhouette against the hall light.

“Boss,” the man says, and clicks on the room light, leaving Dean blinking frantically. “House alarms went off a few minutes ago. John Winchester’s in your office. And he’s got a gun.”

***

Castiel can’t believe he was able to sleep at all, truly. He was nearly awake when Benny had come to his room, a sense of wrongness already invading his rest, but the fallout from revealing his nature to Dean had been exhausting on so many levels, apparently the need for sleep had won out.

Dean had raged. Not the bratting, or attention-seeking behavior he’d displayed previously, but true anger, backed by true fear, and it was a shock to the gut, having a Submissive, his Submissive, hit him with such powerful emotions, visceral, and then curse him for an hour, creatively and passionately. Then, without missing a beat, attempt a very credible banishment spell on him, eyes dead serious and level on his face. Like they had shared nothing, no love, no connection, no bond of any kind.

It had taken hours for Dean’s overt anger to fade, leaving him cold and closed off. He didn’t speak or react, didn’t acknowledge Castiel or anyone else in the house much at all for the rest of the day, though he did respond to direct orders. He was giving out such powerful signals of distress that Benny was driven to say something at dinner, though, and Castiel had acknowledged how difficult it was to be around and not attempt to make it better. However, Dean was still so very angry. He had to soften, first, before any approach could be made.

And now, well. He’s not sure how the boy got word out of the house, but he’s called in reinforcements. Castiel smiles to himself, a little wryly. He’s prepared, somewhat, for this eventuality. He’s not sure entirely how it will go, but no matter what, at least Dean will know how dear he is to his father.

“Up, Dean,” he says to the boy, still a stiff curl at the end of the bed. “Let’s not keep your father waiting. I’m sure he has many questions, hm?”

Dean breathes out heavily, and stands, with a little stagger, before straightening himself proudly. He’s still in his armbands, and Castiel gestures to them. “Can I trust you not to attack me on the way to the office?” he asks, seriously.

For the first time since his revelation, Dean meets his eyes, clearly shocked. He blinks twice, then looks away, but he nods.

“All right.” Castiel unfastens the bindings, but leaves the wrist cuffs on. Just in case. “Let’s go.”

Benny has already left, and is standing by the office door. He looks ruffled and unhappy to be awake, and Castiel tips him a nod; he knows he will have roused the rest of the house, as necessary.

When they walk into the room, the lights are all on and John is sitting, clearly at ease, on the couch, a double-barreled shotgun cradled in one elbow, one ankle up on one knee, arm spread across the top of the couch itself. It could be any friendly visitor, really. He turns to look at them, and smiles.

“Dean.” A wealth of love and fear and relief in one word.

“Dad!” Dean bolts from Castiel’s side, and he lets him go. He leaves the office door open, steps inside, and settles in the armchair, watching John stand and sweep his son into his arms, hold him close, then a little away. Notes that his attention never really leaves either Castiel or the door.

He can see echoes of Dean in John’s face, now. The high cheekbones, the large eyes, straight nose, handsome jaw. Dean’s face is formed in softer, prettier strokes, but their expressions, the wary, guarded looks once their smiles of reunion are over, are the same.

“John,” Castiel nods to him.

“Novak,” he replies, coolly. Sets Dean away, a little, resettles his gun. Castiel is not so foolish to think it’s his only or even primary weapon. It’s just there to draw the eye. John turns back to Castiel, cocks a hip on the couch, and his voice drawls out with a touch of the South, deep and smooth, like they’re discussing the weather. With threats of violent thunderstorms. “What is this I hear about you exposing my son to demons, in a place where he was supposedly safe?”

“Why, I thought you’d been here and checked it out yourself?” Castiel leans back. “More than once, even, so surely, you would have detected any sign of danger. Especially demonic danger. Dean is perfectly safe in this house, and has always been.”

“A demon, a shifter, and a were,” Dean says, cold and firm, standing beside his father, who hasn’t shown even a single twitch of discomfort so far. “And Castiel Novak claims to be an angel of the Lord.”

Castiel enjoys the way John’s eyes go wide a little more than he should, perhaps. In fact, he’s enjoying all of this a bit more than he should. But this man has invaded his home, and is his Submissive’s former Dominant, to boot, so he forgives himself his less merciful impulses.

“Angels do not exist.” John’s deep voice is so certain about that, and Castiel’s grin widens. “A delusional demon, maybe.”

“Former angel, technically. And former demon, as well,” he says, nearly cheerful. “We have all severed ties with our former allegiances, so to speak. It’s a very long story, and probably not one appropriate for this moment. Dean, step over to the desk, if you would. I’d prefer you be a bit further from the line of fire while I speak to your father.”

“Absolutely not.” John’s hand snaps out and holds Dean’s wrist. Dean, for his part, looks wildly conflicted, and Castiel feels a stab of remorse. “You will stay right here by me, boy.” John opens his other hand, and a gleaming silver cord unfolds. With a flip, he opens it in a circle over both of them, settling it around them and letting it fall to the floor. It gives them a good ten feet inside of it, together.

Ah. Protection, no doubt. Castiel hopes he didn’t pay too much for it.

“Benny, could you come in, please?” he asks politely, and Benny comes in the door. “Dean, I’ll ask again, please go stand with Benny.”

“I don’t believe I was unclear,” John tells him, a growl in his voice, now, and Castiel stands. Paces towards him, watches him tense. Watches his lips firm into a thin, bloodless line as Castiel steps over the cord as if it were not there, and walk straight to his face. Right against the gun, shoving it back flat against John’s own chest as if it didn’t exist.

Finally, he can let some of his own anger show. Just a tiny bit, just a flare, a trickle of his true voice, a hint of his real wings, but he lets them out now, surging up to the surface. Black feathers brush the ceiling behind him as he looks John Winchester straight in the eye.

“I am an Angel of the Lord,” he says, feels it shudder through the room, the floorboards, the windows. “You should show me some respect.

John doesn’t so much as flinch, just stares into his eyes. They’re nearly of a height, like this, and John has a kind of power of his own. Steel in him, like there’s steel in Dean, but John’s is tempered in time and wisdom and tragedy and loss. Castiel can see the bitter rot of rage and despair in his soul, too, but it’s small, limited, the love for his sons and his friends so much greater, the sacrifice and accomplishment and honor and dedication counteracting its spread. He looks deeper, his true eyes flaring, and sees stubborn will, tamped-down desires, anger and joy and hope and pride and fear, the full spectrum of a human soul, and a righteous one, and a powerful one.

“Dad, let go,” Dean’s voice breaks the impasse, and John jerks away. There’s sweat standing on his forehead. He drops Dean’s wrist, like he’s startled. “Benny’s a good guy. He’s human.” Dean's voice is a little shaky, and he's looking at Castiel with big eyes, but he's steady on his feet, and steps away from John and over to Benny's side as soon as he's released.

“Plenty of good non-humans here, cher,” Benny chides him a little, ignoring the two men in the center of the room as he slings an arm around Dean’s waist, over by the desk.

“You don’t know what you’re talking about,” Dean bites out, and Benny shakes his head. Castiel can’t let himself be distracted. John steps back and sits on the couch again, almost sprawls, casual and comfortable, and he’s the most dangerous thing Castiel has ever seen on this plane of existence. This man killed the Yellow-Eyed Demon, he reminds himself. Do not become cocky.

“So maybe you’re an angel,” John says after watching Castiel pull himself back into his normal, human frame. “Maybe. But my boy said demons, and weres, and shifters, and all of that right here in this home. Unless angels are also extremely stupid, I can’t see an angel letting monsters wander around unchecked like that. I’ve read my Bible. Angels are warriors of God. You should be slaughtering demons, not babysitting them."

There’s a little growl from the doorway, and everyone’s eyes but Castiel’s snap there as Meg saunters in. She’s dressed for the occasion, he notices. Black leather, skintight, her blond hair sleek and coiffed, eyes lined dark, lips blood red, a boned corset accentuating every curve and heeled boots lifting her up even taller than she normally is.

“We don’t need babysitting,” she scoffs. She prowls over to the couch, trails her fingers over John’s shoulders as she walks behind him, then comes around and struts to Castiel’s side. “We’re partners, after all.” She bares her teeth at John in something that might barely be called a smile, and when she blinks at him, her eyes are ink-black.

Castiel swallows a sigh.

“And that meat-suit you’re wearing, she a partner too?” John returns her snarl, not even bothering to straighten up out of his casual sprawl. He’s so clearly unconcerned that it’s obviously an insult.

“Oh, she was dying, and offered it up,” Meg answers brightly. “Stomach cancer, what a way to go, you know? The boss says she went to heaven, but I’m not really in on that kind of thing.” She flutters her eyelashes at him. “I’m more interested in the earthly delights these days, big boy.” Her voice is a sultry purr.

John’s actually startled into a laugh at that, it looks like.

“Oh my god,” Castiel hears Dean groan behind him, and hears Benny hush him.

“John,” he says, needing to redirect this conversation before it gets any more out of control. “Look at Dean. Really look at him. Has he come to harm, here? We all live by human law, in this house. No harm comes to humans by our hands. No murder, no supernatural harm, either. Our were has a spell and potions to control her shift. Our shifter is constrained by bindings and sigils by her own request. And yes, our demon is voluntarily working on the side of...not light, but humanity.” He leans forward, intensely. “I know it can be hard to believe. But it is the truth. And Dean himself is the proof.”

John looks at Dean. Looks at Meg, at Castiel.

“Bobby,” he says into his shoulder, maybe a hidden microphone, and then appears to be listening. There’s a scuffling sound near the door, and then Cole and the man Castiel remembers meeting, Bobby Singer, come through, both looking ruffled, but not injured.

“Sorry, Boss,” Cole says, looking at Castiel. “Tough old bastard.”

“It’s all right, Cole,” Castiel waves it away.

“Place is warded to Jesus come,” Bobby tells John, ignoring the rest of them. “Like you found before, not a single dark sign.”

John hums thoughtfully, and looks back to Castiel.

“I would never put a Submissive, or any of my people, in danger,” he says simply, imbuing the statement with all the truth it holds.

“Your people ARE the danger,” John claims bluntly, surging to his feet, Meg tensing beside Castiel, Cole jumping to attention.

“Only if you ask nicely,” Meg parries, eyeing John from across the room. He flashes her a terribly insincere grin and just prowls around the couch, eyes flicking from one to the other of them, assessing, calculating. Castiel thinks again, dangerous. It’s putting Cole on edge, for sure, and Meg starts following John, not closely, just moving with him, equidistant, making sure he doesn’t get too close.

“Not even in your wildest dreams, sweetheart,” he drawls, voice thick with southern honey.

“But think how satisfying those dreams would be,” she purrs, licking her lips, and he huffs, sounding surprisingly like Dean.

“Meg,” Castiel reproves. “Enough, please.” The man is objectively gorgeous, but really, the timing. She rolls her eyes, but makes her way back to his side.

Castiel glances at Dean. He’s standing very still, arms crossed across his chest, shoulder bumped against Benny’s, neither of them relaxed, but neither looking all that worried, either.

“You had any magic worked on you, Dean?” John asks, one hand trailing over the spines of Castiel’s books.

“No, sir,” Dean answers promptly. Something in Castiel winces to hear the honorific, and he has to remind himself that he’s probably been calling his father that his entire life, that it probably has nothing to do with dynamics. “Nothing I can tell.”

“That’s something,” John muses, and heads to the window, tapping the glass gently. “Any reason my Devil’s Trap wouldn’t close on your floor, Novak?” He changes the subject so quickly Castiel might get whiplash if he weren’t prepared.

“I guarantee all my people safety in this house,” he answers calmly. “Meg is not affiliated with Hell anymore, but she has some of the powers and weaknesses, and I forbid any traps and magics that would harm her, or any others. Any other questions?”

“I want to know how you did it,” John demands.

“No,” Castiel answers, simply.

At an impasse, they stare at each other again.

“I am taking him home with me,” John says suddenly, silky-smooth, the promise of violence in every word. Behind Castiel, Dean makes a little noise, and Castiel would like very much to know what that sound means, but he will not look away from the threat in front of him.

“You will not,” he stands up.

“I will not leave him in a house with demons. The others, I can countenance, barely, given the evidence. Demons, no.” John’s eyes are glittering. He steps around the couch again, all menace.

“And how will you accomplish that?” Castiel lets menace color his own words. “I hold his responsibility papers.”

“It just needs a word in a few ears, and hunters from all over the Southwest will be coming at you in waves,” John growls, and there’s no smoothness left, just threat.

“Attacks on an upstanding member of society? Will you tell the authorities about the demons, John, when you’re arrested? I’m sure that will go over well with them.” The threat is making him angry, he knows. His wings are flickering in and out, his fists clenching.

“HEY!” Dean’s voice, clear as a bell, has them both snapping around in shock. He’s standing with his hands on his hips, a step ahead of Benny. He’s scowling at them, and it’s such a relief from the blank, cold stillness Castiel has seen since their conversation he reflexively smiles.

“I’m not a fucking bone to fight over,” he says, angry in his own right.

“Your safety is my responsibility,” Castiel states, even as John argues,

“I’m your father, Dean,” and then they stop and look at each other, and at him.

“I didn’t call you to come and kill everybody, Dad,” Dean says evenly. “I didn’t, I haven’t...Nobody here has hurt me. I didn’t even guess, and neither did Sam. Everybody here’s just. Normal.” He runs his hands over his face, looking sad and young, suddenly. "I've seen you fight monsters before, Dad. A lot. Seeing you here, this ain't that. I guess I needed to see that. I just. They didn't tell me." Castiel gets another, gut-deep pulse of that instinctive drive to fix it, solve it, help this Submissive in distress. He takes a half-step forward without even realizing it. He can explain again, how they could not tell Dean, earlier. How it was unsafe, unfair to the staff, unfair to Dean himself, who was not ready--

“Son,” John says, voice suddenly gentle.

“I can’t stay here right now,” Dean says abruptly. Castiel freezes. The whole room goes still, waiting. “I’m too pissed off. I got a lot to think about. I called you because I need your help figuring it out, how to make that work.” He turns to look at Castiel, carefully. “I can’t call you Sir right now. I gotta be away from here. I, please.”

Through the static in his mind, Castiel hears Meg say, “Boss?” And realizes he has perhaps been standing silent for too long. He forces himself into motion, activity, thought and action again. He nods. Dean’s waiting face is all he can see.

“I will only ask this,” he manages, wanting to be absolutely sure. “I am still the holder of your responsibility papers, and before you leave this house, I will absolutely make sure that whoever I sign them over to has all the knowledge and experience you need, and is your own choice, as I promised. Are you sure--”

“What?” Dean interrupts, looking wildly worried, and confused. “What? No. I mean. I don’t want a different Dom. Cas, Sir, I just need time away.”

That sends Castiel reeling all over again, and even John looks baffled.

“Dean, son, are you sure?” He steps closer to the boy, talking softly. “These...people, they’re dangerous, and you’re compromised--”

Dean cuts him off with an impatient wave of his hand. He looks to be gaining confidence by the minute. “I just need to have some time. I want to do some research on my own. I gotta...I gotta figure it out, without being your, your Sub, at the same time.” He glances around the room. “And I’m still pissed off. At all of you.”

“Dean,” Benny says, and Dean just shakes his head.

“You still need a Dominant, even if a temporary one,” Castiel points out, gently. “If this lasts weeks, even months, you must be in hand, you know that.” Dean lets out a ragged sigh.

“I have some friends,” John interjects. “Dominants. Patrick. Gordon. They’re more than willing--”

“I’ll do it,” Bobby gruffs, from where he’d parked himself by the door, with Cole. Dean starts, and looks at him in surprise. “Boy knows me, trusts me. I’d be happy to step up to it, it was killin’ me a little watching him suffer at work, before he came here.” He looks at Castiel, then the rest, nods a bit grudgingly. “You may be a smidge odd, but you do good work. I won’t mess it up. Won’t be my first rodeo with a troubled Winchester, anyway.” Piece clearly spoken, he settles back against the wall.

Castiel truly does forget that John is a Switch, the man is so Dominant in his manner and ways, but looking at him now, the red high on his cheeks, it’s clear which Winchester Bobby’s referencing.

“My my,” Meg murmurs, hopefully too quietly to be heard, and Castiel shakes it off.

“If that’s acceptable to Dean, it’s acceptable to me, with a few further conditions.” He walks back, settles in his chair, suddenly exhausted. Dean himself looks surprised, but not upset, so he forges on.

“What?” John follows him though, and with them seated, the tension in the room drops sharply. Dean sits too, on the edge of a seat by them all, watchful and alert. Castiel can’t look at him directly. Soon, he’ll be gone.

“John, Mr. Singer, even Sam, you’ll all visit here on the weekends, meet with the staff, hear their stories. Learn about us, including the nonhumans.” He sighs. “Sam will continue his training at the Center. And if Dean starts showing signs of illness, regression, you’ll notify the Sublime Submission training school and myself immediately. In two months, if this is not resolved, we sit down in a room and revisit where we all stand, Dean included.”

“I don’t have to visit?” Dean asks, curious.

“You said you needed time away, sweetheart,” Castiel answers, aching. “I’ll do my very best.”

“Thank you. Sir. That’s okay with me. With Bobby.” Dean says, slowly. He even tips his head a little, a tiny gesture of respect. The pounding signals of distress are calming down, slowing, and it’s easing the pressure in Castiel’s chest.

“That sounds acceptable,” John allows. He’s watching them both closely. “Anything else?”

“I have a temporary Dominant guardianship contract for Mr. Singer and Dean to sign. And a profile for Dean, for Mr. Singer, with a few of Dean’s things to take with,” Castiel makes himself say. “Other than that, no.”

“Right then. I’ll get the car.” John stands, and Castiel realizes Dean is leaving, now, soon. He watches that knowledge hit Dean too, in the way his hands clench on the chair arm. “I’ll be about twenty minutes,” he tells Dean, settling his gun back in his arm. “And the rest of you, I guess I’ll see you on the weekend.”

“Drive safe!” Meg calls cheerfully as he leaves. John’s shoulders shift, but he doesn’t respond.

“Sir,” Dean starts, but Castiel shakes his head carefully.

“Fetch your paddle, and stimulators, and your favorite dresses and panties, Dean. There’s a suitcase in the wardrobe you can use. Your chastity cage is in the night table by the bed, pack that as well.” He reaches out and touches Dean’s hand. “Hurry now, go ahead.”

With a little nod, Dean heads out of the room. Meg and Benny and Cole clear out soon after, leaving Castiel with Bobby. Castiel heads to his desk, looking for the profile he’s created for Dean. He hadn’t expected to hand it over to anyone, and certainly not so soon.

“Your Dominance style is your own, but this is Dean’s profile from his nearly three months here,” he starts without preamble, handing the stapled sheets over to Bobby, who’s waiting watchfully. “It has everything you should need, what works and doesn’t for him, his preferences, his fetishes so far, and his no-go’s.”

“Hmm.” Bobby sits in the chair, scans the sheets briefly, and glances at him. “Some of these are intense.”

“He’s a very high-level Submissive,” Castiel answers levelly. “One of the highest I’ve worked with. You may be able to get away with not giving him high-intensity domination as regularly, but he does need it.”

“Hmm,” Bobby agrees, and continues reading.

“If you have any questions, or run into problems, you can call,” Castiel offers, suddenly desperate. “I know it’s not customary, but for Dean’s sake. I would be happy to assist, or advise.” He looks down at his desk.

“I can tell you’re in love with the boy,” Bobby says gruffly, after a moment’s pause. “I don’t want to twist the knife.”

“I will just be glad to hear he’s well,” Castiel admits miserably.

“Can’t you just use some angel magic or somethin’?” When Castiel glances up, there’s a twinkle in those sharp blue eyes.

“It doesn’t actually work that way. But if it did, I might,” he admits.

“Don’t fret too much, angel,” Bobby says, folding the profile and putting it in his pocket. “These Winchesters, they’re stubborn as sin and twice as nasty when they’re riled, but give them some time to settle down and they’re too sensible to give up on a good thing. Hell, John himself walked out of here without firing a single shot. Think it was the sight of his boy all healthy and proud is what threw him off his game, honestly.” He winks at Castiel, then taps the desk. “Where’s that contract?”

“Oh. Right.” Reluctantly, Castiel fishes a boilerplate temporary guardianship contract out of the filing drawer. Filling in the names and dates takes only a moment. There’s some comfort in still having Dean’s permanent papers, but he knows how fragile that bond truly is. He and Bobby both sign, and there's a spot for Dean to sign at his leisure.

Dean’s arrival with the filled small suitcase has both of them turning. He’s talking to someone at the door, Benny, it sounds like. They can hear a back-pounding hug, promises to call, and then Dean’s carrying the case into the room.

“I’ll get this out to the car while you sign that and say goodbye,” Bobby says, with what looks like gruff tact, as Castiel just looks at the boy. “Novak, I’ll be in touch.” He shakes Castiel’s hand, and then he’s gone, with the suitcase.

Dean signs the contract, steps back, fidgets where he’s standing, then looks at Castiel defiantly.

“I’m not sorry,” he says.

“You shouldn’t be,” Castiel answers him. He stands up and comes around the desk, slowly. “I want to tell you why I’m proud of you. May I?” Right now, Bobby Singer is Dean’s Dominant. It is only polite to ask.

Dean nods, a small, almost shy motion.

“You were angry, and in a situation that felt out of control, so you reached out for help. You spoke your mind, you realized what you needed, you made it happen. All without a single outburst. You accepted compromise. You stood up for yourself, respectfully and with maturity. Dean, I have never been more proud, more pleased, more impressed.” He reaches out, then pauses. “May I give you a hug, before you go? Because I will miss you, very very much.”

“Sir,” Dean chokes out, and flings himself into Castiel’s arms, staggering him a little. He wraps himself around the boy, holding him tight and close, burying his face in Dean’s neck as he feels Dean do the same. He can feel the hard anger still written in every line of Dean's body, but the sheer affection and even love of the embrace is clear, too. Hope and pride and sadness tangle in his heart, and he crushes Dean even closer.

“Be my good boy, darling,” he breathes into soft skin. “No matter what, make the best decisions for you.”

“I’ll miss you, Sir. Say goodbye to Angelique and Claudia and Ash and Crowley and, and Meg for me, okay? And Charlie, I don’t have her email, oh god,” Dean is breathing hard against his chest, and he strokes calm into his skin.

“Shhh, shhh. You’re only going to Austin, lovely. I will send that information to your father via email. All right? And you may call the house here any time you want. You’re always welcome to reach out, but we will give you your space and not do the same, until you tell us you wish otherwise.” He pulls back when he hears Bobby clear his throat at the door.

“Goodbye, Dean. You are a wonderful Submissive and it’s been an honor to have you in the house.” He dredges up a smile.

“Bye, Sir.” Dean’s eyes are wet but his face is resolved. He shakes himself all over, like a horse settling its skin against flies, and straightens up. “Thank you, for everything. I’ll see you soon.” he nods firmly, and follows Bobby out the door.

Castiel stands where he is and listens to the silence in the house for a long time after the door closes behind them.

Chapter Text

Dean opens his eyes to his familiar bedroom, and for a single, blurry moment, has to wonder if it’s all been a dream. Then he hears the door slam downstairs, rolls to his side, sees his own small suitcase from Castiel’s house there by the bedroom door, and it all floods back. He lies still, just breathing, not letting himself think for a long few minutes, before heaving himself off the too-small bed and stumbling to the bathroom.

Washing his face. Brushing his teeth. Taking a piss. He feels strange, alien, doing it. He stares down at the toilet bowl, tired mind trying to process why it feels wrong. He’s alone. He’s holding his own dick. He could...he could jerk off, if he wants. His sub brain, small and quiet and bruised-feeling, tight with panic since last night, recoils at the thought, and he shakes it off for now. Still wearing the cut-off sweats and ancient t-shirt he'd gone to bed in, he pads down the stairs silently. It's still really early, the house and outside quiet.

Dad’s standing at the kitchen sink, obviously just back from a run, shirt stuck to his back with sweat, gulping water.

“Dean,” he smiles, when he turns and sees Dean standing in the doorway.

“Hey Dad.” Dean shifts on his feet, feeling strangely out of place. “Morning.”

“Glad to see you up and talking, you were pretty beat last night. Why don’t you get a pot of coffee going? I’ll grab a shower, you make two cups, meet me in the living room in ten?”

Happy to have a goal--and coffee--Dean nods. Everything’s right where he remembers it. Strange that nothing here has changed, when he feels so very different. But the routine of filling the coffee maker, getting down mugs, brewing, black for Dad and a little sugar for Dean, it’s familiar and soothing, and he walks into the comfortable, battered living room at the same time as his Dad, who’s toweling wet hair.

“C’mere.” Taking the two mugs and setting them on the coffee table, he tugs Dean right into another hug, sitting them down on the couch without a pause, and Dean heaves out a huge sigh, returning it, squeezing his dad tight around the ribs.

“Ooof. Glad to see you haven’t been slacking on the PT while you’ve been gone.” There’s a smile in that deep voice, and Dean finally finds his voice again.

“Daily runs, with an Army Ranger. Martial arts training. You would’ve loved it,” he grins into John’s shoulder.

“Sam told me some’a that. I was real pleased.” He holds Dean tighter for a moment. “Missed you, son.”

“I missed you too, Dad.” It’s true, and heartfelt. For all Dean’s confusion, and fear, and anger, it’s so good to be here, to see Dad, to be home. When his dad pulls back from the hug, they’re both smiling.

“I’m glad you’re up. We didn’t get much of a chance to talk, last night. I took today off work, too, to catch up, help you settle in. Sam’s not going to school, either, that was the deal, since I didn’t let him come with me and Bobby last night.” John rolls his eyes, and Dean laughs a little.

“Yeah? He drives a mean bargain.”

“Like you don’t even know. Bobby’s coming to dinner after closing up the shop, so you two can figure some things out, too.” Dean pulls back a little, looks down at his hands. It’s one of the things that’s twanging at his nerves, now that he’s not in the moment, in that study, surrounded by on-edge Dominants and standing his ground. Bobby as his Dominant, even temporarily. Uncle Bobby.

“I gotta ask. Dad. Bobby’s like family to you. To us, too. You okay with...with all this?” Even apart from whether Dean himself will be.

“Well, that’s a whole story.” Dean looks sideways at his dad, who’s leaning back and smiling a little. “I’ve been reading some of Sam’s books, did he tell you?” Amazed, Dean shakes his head. “It’s true. I figured, I got High Sub and High Dom kids, I should start learning more about this stuff. Better late than never.” His smile twists in a way that makes Dean want to give him another hug. “Turns out, back when people used to live in extended families, uncles and aunts and cousins, distant relatives like that, they were pretty important to young Subs and Doms. They would take them under their wing, teach them the ropes, let them practice and learn before they were ready to have real relationships.” He looks at Dean. “If I hadn’t had my head up my ass about you, Bobby could’a been that for you years ago.”

“Dad, no!” Dean protests, sitting up.

“Dean, hear me out.” John raises his hand, and a lifetime of training has Dean quieting, if reluctantly.

“I ignored what was right in front of my eyes for way too long. It was pretty clear you were struggling, and I didn’t do right by you, not soon enough. I know I can be bullheaded, but I try not to let that fall on you boys too much, and this time it did, and I’m sorry.” He looks right in Dean’s eyes, and Dean can see sorrow there, guilt. “Never should have got that bad, son.”

“It wasn’t your fault,” Dean chokes out, his throat suddenly thick.

“Sure it is,” John says, sturdy in his sense of responsibility. “I’m your father, and I was your Dominant, too. Both ways, I let you down. You let me own that. I’m going to try to do better.”

It’s maybe the most Dad has talked about this kind of stuff with Dean, all at once, ever. And from the look on John’s face and the way he slugs back his coffee, they might just be getting started. Dean drinks his coffee too, and nods.

“Okay. Okay. I accept your apology, then. Nobody knew, and I wasn’t exactly opening myself up for any kind of help, either. But okay.”

“All right.” John shakes the arm around his shoulder, only a little roughly. “Good. I might not have your papers anymore, and that’s fine, but I’m your father forever. Don’t you forget that.”

“Not much chance of that,” Dean vows.

“Good,” John repeats. “Me and Bobby, we chatted some while you were sleeping in the car. We figure with some routine at home, and spending some time with him, we should be able to keep things squared away for you. Novak gave us a pretty big profile about your time there, but how about you tell me, too? Before your brother gets up,” John adds, hastily.

“Dad,” Dean protests.

“Nothing you’re not comfortable with,” John tells him. “You can share that with Bobby, if you need to. But I want to hear about my boy. How you got healthy, the things you did. What you enjoyed. Tell me about the people. Make it a field report, if you like.” He grins at Dean. “After all, I’ll be seeing them again on Saturday. A little extra intel wouldn’t be a bad thing.”

Dad and his ‘knowledge is power,’ again. And he’s genuinely interested, maybe.

“You hate the...the subby stuff,” Dean protests again, more weakly this time, staring into his coffee cup.

“Dean, kiddo.” John’s hand is warm on his shoulder. “That’s some of what I was apologizin’ for, before. I was wrong, some of the old fashioned ways I had, the things I said. My momma, your Grandmother Winchester, she was a high-level Dominant, and she always held that Submissives belonged in the house, in obedience, that Subs and Doms were mostly to be kept apart unless they were in relationships with each other. She was real strict about raising us that way. And with your mom and me both Switches, well, we just didn’t get a lot of chance to live different. But I’m learning that wasn’t right, and you’re proof standing in front of me. Bobby’s already tore a strip off me with his tongue, and your Aunt Ellen, too. Give your old man a chance, here.”

Jesus. Is the sky falling? Is the sun purple? Are pigs currently flying past the windows? Dean knows his mouth is hanging open as he stares at his father, but seriously. Who stole his dad and replaced him with this pod person? Is he on drugs?

John winces at his expression.

“Like I said. Bullheaded. I know. But a soldier who can’t learn and adapt in the field is just a dumb weapon to be pointed and aimed by a smarter hand. I try not to be too stupid, if I can help it.”

“You’re not stupid,” Dean says automatically. He takes a deep breath. Then another. “Fuck,” he breathes out. Puts his coffee cup on the table, and his face in his hands. It’s like the world, so recently shoved askew, has been yanked out from under his feet yet again.

“You...I worked at Bobby’s,” he says into his palms, his voice shaking. “I hunted, with you. You never made me feel helpless till we found out I might be a higher level Sub.”

“And I’m sorry for that.” John says steadily. “That wasn’t ever what I meant to do.”

“Goddammit Dad,” Dean’s breath catches a little. “Why we gotta talk about this stuff? Can’t we just go to the range and shoot things like we usually do?”

“That’s tomorrow. Today we clear the air.” Now John’s smiling again, Dean can hear it.

“It’s pretty clear now,” Dean grumbles, and scrubs his face, finally looking up. “Okay, I guess I can tell you about the house, if you want.”

“I want.” John settles back into the couch, bringing Dean with him, slinging his arm over his shoulders again. “What rules did they give you when you got there? Bet that was a shock to the system, huh?”

“Holy crap, like you wouldn’t believe,” Dean nods, suddenly enthusiastic. He turns a little so he can see his dad’s face, and starts listing out the surprises of his first day at the Novak house.

By the time Sam stumbles downstairs, bleary-eyed and his hair wild, Dean has already talked about his schedule, the training area and the rooms, the different Submissive positions, and is describing leash and tether training, urged on by an occasional interested question or comment. He had been a little shamefaced, admitting to a panic attack, but John had waved it away, and been fascinated by how Meg had handled it right away, and then the change to the rules.

“Meg, the demon?” He asks, pointedly, and Dean’s eyes go wide, he’d actually forgotten, and then,

“Dean!” Sam’s face lights up, and he only stumbles over his feet once getting to them, and engulfing Dean in a massive hug. It’s only been about a week since Dean saw him and he’d swear the kid’s grown another inch.

“Oof, Sam, off,” Dean grunts, smothered, and shoves at him until he can breathe again.

“What the hell happened? Dad and Uncle Bobby got some message and armed up and flew out of here like the house was on fire...did someone attack Mr. Novak’s house? Is everyone okay?” He looks between them.

“Uh,” Dean says slowly. “So...about that.”

Sam is beside himself once it’s all explained. He can’t believe he hadn’t seen or detected it, and over breakfast, bugs Dean until he goes through what he knows about the supernaturals in the house again. Except Castiel, Dean won’t talk about him, beyond the basics. Not yet, anyway. Dad disappears into his office while Sam washes and Dean dries the breakfast dishes, the familiar rhythm of it soothing the itchy weird feeling in Dean’s skin. He looks around when they’re done and realizes he has nowhere to be. No schedule, no structure, no one expecting him. He shakes it off, and follows Sam back into the living room for some good old-fashioned day off lazy time, if he can dodge the million-and-one questions.

***

Dinner starts out awesome. Bobby blows in after work, and Dean was kind of worried it would be awkward, but it isn’t at all. He’s just normal Uncle Bobby, teasing Sam about missing school, dumping his work boots by the door, offering to help Dean out with the potatoes. Dean’s super fucking tired, he can feel it behind his eyes; after all, he’d gotten like four hours of interrupted sleep last night, total, so he’s happy for the help. And once they’re all sitting down, everything’s good for a while, too, until Sam starts asking questions that aren’t his business.

“So you going to be going back to the training school, Dean?” He’s eating the chicken pretty quickly, Dean notices. Needs the calories for all that growing, probably.

“Nope,” he shakes his head. “All done with that training stuff.”

Sam narrows his eyes at him. “You said you were taking some time off from being with Mr. Novak, but you have to have a Dominant, Dean. At the school they could set you up--”

“Sam,” Dad says warningly. “Dean’s going to be Submitting to Uncle Bobby on a temporary basis, while he figures things out. And that’s all you need to know about it.”

Sam turns to him, now wide-eyed with worry. “Uncle Bobby’s not high level enough! It’s important, Dad, it means the intensity won’t be there, it won’t line up right--”

“Sam,” Bobby tries to interject, but Sam actually starts getting his Dominant voice on.

“It’s not fair to Dean, not when the school is right there.”

“That’s enough, Samuel.” Now Dad’s voice is rumbling. Dean’s head hurts.

“This isn’t any of your business, Sam,” Bobby chimes in, and Sam rounds on him.

“He’s my brother, of course it’s my business!”

“Guys, please.” Dean is too tired to hide his distress, the headachey miserable feeling of them battling about his stupid high-level Submissive needs, and somehow, like a miracle, they all go quiet, turning to him almost in sync. Their faces change, too. Sam’s falls, Dad’s is worried, Bobby’s goes soft around the edges. Somewhere in the back of his fuzzy mind, he is amazed.

“Sorry, Dean,” Sam says quietly. “I’m just worried.”

“Bobby and I have talked about it, Sam, we understand the challenges and we’ll work it out with Dean, and make sure he’s all right,” Dad assures him, though he’s still watching Dean. “You all right, son?”

“Why don’t Dean and I go take a break, and John, you can join us after dinner’s cleaned up? Bring his case with you,” Bobby suggests. It sounds great to Dean, whose ears are still echoing, whose skin feels too tight and aching, and who is too damn tired to argue about it.

“Yeah, okay,” he mutters. It’s easy enough to follow Bobby to the small front room that nobody ever uses. Usually it’s got a bunch of hunting gear and other stuff piled in it, and sometimes they use it as a guest room, but someone’s been busy today because it’s all cleared out and sparkling clean, a new area rug down over all the hardwood floor. There’s a couple of chairs and a kneeling pillow by one of them, and a bench beside the daybed.

“Strip right down, kiddo, and go kneel on the pillow,” Bobby orders him quietly, and it IS an order. His sub brain, dizzy and off-balance, latches on to it with gut-wrenching relief. Dean gets his clothes off, fast, and his skin feels so happy to be bare again, like it’s breathing free. He rolls his shoulders, comfortable and loose, and pads to the pillow, and sinks down into Wait, feeling the familiarity of the position ground and settle him. He feels Bobby looking at him, all over, and pulls his shoulders back just a fraction.

“That’s very good, Dean. Real pretty.” Bobby sits in the chair next to him, and runs fingers through his hair. Sighing, Dean breaks position enough to tip his temple against Bobby’s thigh.

“Good boy,” Bobby praises, and something thirsty in Dean drinks it in. “We wanted to give you a day to just settle in, but that was a pretty sharp change from what you’re used to, I reckon.” Dean rocks his head against his thigh in a nod. “That’s all right. We’ll set some rules and a schedule for you tonight, get you all set and sorted out.”

“Sorry to be a pain,” Dean manages to get out. He’s high-needs. He keeps hearing it. Bobby signed up for it, but does he really know what he’s getting into? Dean can’t even get through a free day without needing this, now that he knows how it can be. What if it’s too much? What if Bobby decides he can’t do this, and Dean’s left alone, without a Dominant after all? His breath speeds up a little at the thought.

“None-a that,” Bobby scolds gently, the hand in his hair gripping lightly for a little shake. “You kiddin’ me, boy? This is a treat for me. Getting to be a family Dominant for you like this, it’s a great thing.”

“You sure?” Dean manages to look up at him, sideways.

“Absolutely. And don’t you mind that brother of yours. We’ll get you what you need and make sure you have the time you want to figure yourself out.” Bobby nods decisively, and Dean breathes out heavily, relieved, and actually relaxes. “There you go,” Bobby approves. “That’s better, now.” Dean nods again. And then another, different worry starts to grow.

He startles a little when John opens the door and steps through, carrying his case from the house, but Bobby just pulls him back, and John smiles at them, sits in the other chair with the case between his feet.

“Think it’s time we laid down a few rules,” Bobby starts, without any preamble. “And John, he’s your father, not your Dominant, but he’s my proxy since you’re living with him and not me. So he needs to know ‘em as well as you do.”

“What’s that mean?” Dean asks, puzzled.

“Means I give him leave to enforce the rules when I’m not around, just like those other Dominants in your training house,” Bobby explains. “And none of those little spankings you were used to, either. Proper punishments. We’ll get into that later.”

“Oh man,” Dean groans. John smiles again.

“First rule is, you tell one of us right away, you start feeling sick, or off, or not-right. I know you remember how it felt before, when you were out of balance? You start feeling that again, you let us know right away.” Bobby lifts his chin up to meet his eyes, and he’s dead serious. “That one’s critical.”

“Yessir,” Dean replies, automatically.

“Good boy. Up and on your feet, in front of me, at attention.” Dean goes instantly, confused but obedient. “Thanks for bringing that down, John. Can you fetch out the chastity, please?”

Dean goes instantly hot as fire in his face, he can feel it. He barely notices his dad handing over the familiar cage and a bundle of keys. Bobby’s gentle fitting it onto him, cool and heavy and calming in its presence. He can feel the rules settling around him again with it, beautiful in their solidity, in the way they give his sub brain the freedom to stretch again, and that feeling distracts him enough that he’s almost startled when he feels the click of the lock.

“John will have a key, I will have a key, and since you may be home alone, there is a key in the gun safe,” Bobby says seriously. “You are on the honor system to never use it unless there is an emergency. The second rule is, no masturbation, no pleasure touching of any kind, and no orgasms without permission.”

Dean nods.

“You’re a grown man, and I expect you’ll want to see friends and go out and have fun. I certainly won’t stop you. Third rule, I expect a phone call before you go out, and a text message when you get home.”

Dean opens his mouth to protest that, and is pinned with Bobby’s stare.

“I’ve heard a few too many stories about bar brawls and arrests for this to be just a timewaster, young man.” It’s the ‘young man’ that does it, and Dean wilts.

“Yessir,” he mumbles.

“In that same line, fourth rule, your bedtime on work nights is ten-thirty pm. No arguments, no exceptions.” Too used to that from Castiel to even flinch, Dean nods. “Last rule. You want to make an argument, you can do that, but do it respectfully. When you’re submitting, you use your manners. No cussin’ or yelling, least when we’re like this. That last rule’s are pretty much set aside when we’re in the shop, but for now, those are it. We’ll test them out, and see how they work. We’ll adjust them if we gotta, so you let me know if you think one just doesn’t feel right.”

“Yes, sir,” Dean agrees.

“Good boy,” Bobby praises, warmly, and Dean’s knees betray him and he sways a little. Bobby smiles and gives him a tug, and he ends up right in his lap. Bobby smells like home, like clean laundry and a little like motor oil and the tang of gasoline, and Dean happily leans into his shoulder. “Sweet boy,” Bobby adds, softly. Dean just about melts right there.

“The reason your bedtime is so early is because you’ll be running with me in the mornings.” John’s deep drawl doesn’t jar either of them. He’d been present in the periphery, watching quietly, just a little apart, but there in Dean’s consciousness. “I’ll get you up in the morning, we’ll run, shower and have breakfast, and I’ll drop you at Bobby’s before work.”

“We set this room up for you,” Bobby continues. “This is your room, for Submission. If you need to kneel, be quiet, you can come here. Alone, or with one of us. I saw how nice it was for you to be bare, in here you don’t wear clothes. Sam isn’t allowed in here, and no houseguests. This is just your space. I have a room like it at my house, too. A lot bigger, though.”

“Why bigger?” Dean glances around the room. It seems fine. He likes it. Loves the idea, actually. His own room is pretty cool.

“I got a bigger house, and just me in it. Plus it needs more stuff. When John drops you off in the morning, you’ll go right there, strip, and wait for me. We’ll have an hour or so, and then go to work. After work, we’ll spend some time together again, if we’re not too tired, and I’ll bring you home, except every Monday when the shop is closed, you’ll spend the day and night at my house.” He rubs the top of Dean’s neck, and soft, gooey warmth floods him. God, those glands are magic. “Once you get home and shower, and have dinner, you’ll spend a couple of hours naked in the house. You can spend them however you like, within the rules, until bedtime.”

“In the house? Not in here?” Dean’s curious. Weirdly, not freaking out. He feels like he should be, but...Sam saw him naked for days in the training house. Dad’s seeing him naked right now. He really likes not wearing clothes, it feels right, and good, and he’s still just really tired.

“In the house,” Bobby confirms. “John will give you bedtime spankings, and then you’ll go to bed on time.”

“Uuuurgh,” Dean groans, turning his face into Bobby’s shoulder.

“I can’t tell if he’s more upset at the bedtime, or the spankings,” John’s amused voice chimes in.

“I’m giving you your morning discipline at my house,” Bobby tells Dean, and he sounds amused too. Freaking Dominants, always think smacking Dean’s butt is so funny. “Because running with a freshly spanked bottom ain’t fun. That’s how nice I am.”

Dean just looks at him, outraged, and Bobby chuckles.

“Speaking of discipline, though.” John’s voice is serious now. “Bobby has told you that I’ll be administering punishment if needed when he’s not here.” Something in his voice makes Dean sit up and look, and he has a wicked-looking holed wooden paddle in his hand, with a leather strap laid over it. “I’m sure you’ll be a good boy, but if not, these are the punishment implements, now. The evening spanking is just for maintenance and won’t be severe.”

Bobby nods. “They’re similar to the ones at my house. I don’t know exactly how Novak disciplined, but I’m pretty strict.” There’s no nonsense in his voice. “There’s also a switch and a cane, and I’ll pull those out if I need to.”

“I am very good,” Dean declares, sitting up straight, and looking at them both. His sub brain is in the forefront, now, and is making every promise to be the best, most obedient boy. “You’ll never have to use those, for sure.”

“Hmm,” Bobby cocks an eyebrow at him clearly dubious. “Well, I hope so. We’ll see. Now, boy, I can see how tired you are, just lookin’ at you. Why don’t you ask me any questions, and we can get you sorted out for bed.”

It’s a simple schedule and set of rules compared to what he’d had at the house, but feels kind of satisfying anyway. Still, there’s that one nagging concern, from before. He shifts self-consciously on Bobby’s lap.

“You said it’d be a great thing, to be a family Dominant, for us, for me?” Dean confirms, just to be sure.

“Yep,” Bobby nods. His hands are firm on Dean’s waist, his hip.

“Does, uh. I know I’m wearing the cage, but. If you’re a family Dominant, does that mean, is that a no-sex thing?” Afraid he’ll hear laughter, he doesn’t look up.

“Dean, no,” Bobby says, firmly. He nudges Dean’s chin up again. “Just because it’s not anyways romantic, because it’s more family-like in nature, doesn’t mean it will be chaste. That kind of thing wouldn’t satisfy me, and I know you’re a very sexual Submissive, so it wouldn’t work for you either. We’ll get our dynamic all settled tomorrow, when you get dropped off.”

“Oh,” Dean breathes, relieved. He’s still tired, sure. But with every answer, some of the thick, heavy anxiety that had been muffling him, weighing him down is lifting away. “What about hunting,” he asks them both. “That schedule, it’s really full. What about if there’s a hunt? Can I...” He looks at his dad again, hopeful.

“I’ll be thrilled to have my best partner back with me,” his dad nods, seriously. Honest to god, Dean feels tears almost start in his eyes.

“If he’s been eating and sleeping right, and at least mostly been a good boy,” Bobby interjects. “All signs you’re healthy and in good balance,” he says, to Dean’s wounded look.

Dean has to concede that point. He’d have been wendigo chow if he’d gone out like he was before.

“Thanks, Dad, Bobby. That is, yeah. Awesome. Can’t wait,” he beams at them.

“Okay then, boy, time for bed for you, before you fall down where you’re standin’,” Bobby orders firmly. “John, you’ll discipline him here, or in his room?”

“Here, I think,” John says thoughtfully. “Come on, Dean, let’s get this done so you can get some sleep.” He pats his thighs. Dean stares at him, then at Bobby. Suddenly, this doesn’t seem like a great idea. It won’t feel like his paddles at Sir’s. It won’t be the same. He doesn’t want his dad spanking him anyway. His dad isn’t his Dom anymore. It’s all too different, too much, all at once.

“I don’t need a spanking,” he tells his dad. “I just need to sleep. It’s my day off, Bobby said.”

“Dean,” his dad says, and there’s a little bit of warning in it. Dean feels a prickle of tears in his eyes. Stupid, stupid.

“I don’t want it,” he insists. “It’s not the same, it won’t work anyway. Everything’s different here, why do you guys have to make this one dumb thing try to be the same? It won’t work!” He jerks up off of Bobby’s lap, tense and nervous.

“Dean,” his dad says again. “It won’t be the same. We ain’t using that paddle, it read in the report like that was a special thing you had there. But it also sounded like something you really needed, so we’re gonna go ahead and keep it as part of the routine.” He looks all gentle and understanding, and it’s making Dean kind of crazy.

“Go on. No fussing,” Bobby warns, and it’s definitely a warning. He stands up behind Dean and gets his hands on his shoulders and marches him right over to where John is sitting. Dean doesn’t fight it, not really, though he’s stiff and unhappy about all of this. He doesn’t want to make Bobby regret his decision. He hauls himself over John’s knees, scowling, feeling stubborn and silly, his butt up in the air.

“Nobody’s mad at you, kiddo.” His dad’s deep rumbly voice is kind of nice, he guesses. And it’s not like this is an unfamiliar position. A big warm hand pats and strokes and soothes over his bottom. “This is just the end of the day. We’re gonna do twenty, and they won’t be hard, since you got some bruises here. Just relax and settle.”

Dean refuses to nod, and just huffs against the chair, where his chin is propped a little awkwardly.

The first smacks are light and stingy, peppered over both cheeks. They make his skin warm and tight but don’t really hurt. Gradually though, they get harder, more direct, and before too long Dean’s crossing his ankles up behind him at the sharp, hissing pain. He sniffles, turns his face, clears his throat, and then he can’t hold it in and he’s crying quietly, his sub brain letting go, relaxing into soft ease, relief, calm. His dad has him, Bobby has him, they’re both right here. Spanking him through the tears, steady, until the last one comes down and there aren’t any more. Then his dad’s hand is on his back, rubbing it, and down to the base of his spine, thumb digging in hard, and he’s flooded with relaxation, ease, Submission, he almost gasps with it, the relief.

“Good boy,” Bobby’s Dominant voice is rougher, higher pitched than Castiel’s, not as intense, but Dean still thrills to hear it, to know he’s pleased with Dean.

“That was real good,” Dad agrees. That’s even better. Both of them are happy with him, and he breathes a big sigh. The world’s still off balance, he can still feel the anxious nerves, but they’re milder, in the background. He sits up carefully, with Dad’s help, and clears his throat again.

“Head up and brush your teeth, wash your face, and right to bed,” Bobby orders gently, reaching out to brush a tear off his cheek. “I’ll see you in the morning, boy.”

“Yessir,” Dean nods gratefully. “Thank you.”

“You’re welcome. Now git.”

Dean goes, bottom nice and warm, and hurries up the stairs. He gets through everything quickly and crawls under the covers with relief, eyes so heavy he can barely blink, and he’s out before he can even think about it.

***

The deal is, on the four days a week Dean is scheduled to work and runs in the morning with John, Sam doesn’t have to run with them, but he does have to get up and make breakfast. That first morning, stumbling back in after a fast eight miles, Dean realizes it’s totally worth it, since the house smells like bacon and coffee.

“First shower,” Dad calls it, and Dean shrugs it off. He can get a whole cup of coffee down him before it’s his turn, and that’s good enough for him.

Sam’s in the kitchen, finishing up some basic eggs, looks like, and Dean swings a sweaty arm over his shoulder, grinning at his scowl.

“Man, I didn’t even see you last night,” Sam complains. “You were in bed before I even got back from the library.”

“Yeah, I was beat. Didn’t sleep much at all the night before, plus, everything’s kind of crazy right now. Getting it all settled with Bobby and Dad was kind of a long talk.” Dean pours coffee, gulps some down.

“You know I wasn’t trying to be a dick, right?” Sam looks so earnest, even his pointy little nose is almost twitching. “I just worry about you.”

“Bobby’s got it,” Dean assures him. “And look. I’m gonna be going hunting with them, too, as long as things stay steady, so I’m going to be trying extra hard, so it’ll be fine.”

Sam looks at him, skepticism all over his face as he scrapes the eggs onto a plate. “I don’t think it’s really a willpower thing, Dean.”

“Don’t let Dad hear you say that,” Dean points a finger at him cheerfully. He hears the water turn off, and dashes out of the kitchen to take his own quick turn. Nothing worse than cold eggs.

The ride to Bobby’s is strange and familiar, all over again. His eyes keep catching on things he’d never have noticed before. There’s a lady kissing a guy goodbye for the day in a doorway; he can tell the guy is naked. There’s a girl in a collar, walking a dog. She looks pretty happy, Dean guesses. And there’s a billboard, an ad for the new Dominant Training Center, with Gabe’s giant face on it.

Suddenly struck, Dean freezes.

“Dad,” he says urgently, and his dad glances over at him, concerned. “Dad, Castiel’s brother’s name is Gabriel. His other brother, the one in New York? Michael.”

John blinks slowly at the windshield.

“Well. I was planning on taking you boys out to the range tonight after dinner, but I think we’ll be doing some research into the angelic hosts, instead,” he says tightly, not looking away from the road. “You think hard today, remember everything Castiel Novak might have said about his family, names, anything. And we’ll loop that in.”

“Yessir,” Dean nods, and then they’re pulling in to Bobby’s driveway. Dean resolves to put the whole angels and demons thing out of his mind until later.

Deep breath, drying his sweaty palms on his jeans, and Dean jumps out, waving to his dad as he pulls away. Then heads into the house. Be good, he reminds himself. Don’t disappoint Bobby. Don’t make him regret taking you on. Time to put on your big boy pants, Dean Winchester. Make Bobby and your ‘Sub needs’ happy while you figure out this stuff with the angels, while you get your feet back under you and try to understand how you feel about Castiel and all that stuff he didn’t tell you, and that’s all that needs to happen.

“Third door down on the left, Dean,” he hears Bobby call from somewhere in the house when he walks in. “Strip down, and wait on a kneeling pillow, I’ll be right there.”

Right, okay.

The room is a lot bigger than his room at home. He vaguely remembers it as some kind of formal parlor, but now it has all kinds of stuff. A bed, a breeding stand, a spanking bench, a couch. There’s a big wooden cross against the wall that Dean looks away from, and a couple of cabinets, a small fridge, and there’s a bunch of pillows on the floor. Dean folds his clothes up and kneels down on one with relief.

“Morning, boy,” Bobby says from the door, and Dean cranes around to look. He’s just wearing soft looking sweats this morning. He’s big through the shoulders, a little soft in the middle, gray hair on his chest matching his beard. His hair’s still damp. “Got here a little earlier than I was expecting.” He walks over, settles in one of the chairs, and beckons Dean over. “Move that pillow over here.”

“Okay, yeah. Morning, Bobby.”

“That’ll be Sir, or Master, while we’re here,” he orders firmly. “And we’re skipping your morning discipline today, because we’ll be doing a full scene, and I want time to talk, first.

“Right, yes, sorry. Sorry Sir.” Dean winces. And then has to bite his tongue, because Sir never skipped his morning paddles. It was a ritual, it happened every day. That’s what made it what it was. But this is different, he reminds himself. Be good for Bobby. Don’t think about Novak House, he’s not doing that today.

“It’ll be a little tricky, moving back and forth like we’re gonna do, between work where we’re Dean and Bobby, and in here where we’re boy and Sir. So I’m gonna insist you’re real careful with your language,” Bobby goes on. He draws Dean between his knees when he has the pillow settled, just touching his neck and shoulders. “Let’s talk a lil’ bit about how we’re gonna be together in here.”

“Yeah. Yes, sir,” Dean says, eagerly. It’s only been a couple of days, sure, but his hole clenches a little. It feels empty, neglected, and his cock pushes at the inside of the cage.

“Now, your papers say you ain’t a masochist at all. That true?” Dean nods. “All right. I’m just cross-checking, here. But you’re a sacrifice and objectification Sub, you like bein’ used for the pleasure of your Dominant, even if it doesn’t feel good to you physically.” Cheeks flaming, Dean nods again, this one smaller. “You’ve got some issues with bondage, but not all kinds of bondage. You enjoy feminization, medical, age play, lactation, urine and desperation play, and spanking as well as other light impacts.” Biting his lip, Dean has to nod.

“That’s a good list, boy,” Bobby’s voice is warm, and Dean looks up, and he’s smiling. “Think we can do a lot with it. I’ve got some sadism, enjoy bondage and discipline, desperation, orgasm control and denial, and feminization and medical are two of my big fetishes. We’ll bring some of your pretty things over tomorrow, and maybe go get some more, too.”

“Thank you, sir,” Dean breathes out, relieved.

“Today we’re gonna keep it simple. I want to see what you know, we’ll do a little flogging session, and then I’ll fuck you nice and rough to make sure we’re imprinted nice and solid.”

Dean gulps, and nods. His cock cage is almost painful, now. Bobby reaches down and holds it, weighing it in his hand, and Dean squeaks a little, swaying on his knees.

“This is gonna stay on pretty much full-time. Including today.” He meets Dean’s eyes seriously. “I don’t want you getting any false expectations here. I like my boys horny and desperate. Keeps ‘em mannerly.” For the first time, his grin is sharp, hungry, sexual, and Dean sucks in a little breath. “On your feet, now. I want to see your positions, see what you learned at that fancy training house.”

Head spinning, Dean rises. No orgasms? For now, or like, ever? His sub brain is torn between ecstasy and terror at the thought. Be good for Bobby, he reminds himself, like a mantra. No fuckups, no acting out. Schooling himself into silence and obedience, he stands ready, at attention.

“Hmm. All right, good. Down and Wait.”

Bobby takes him through the positions, and as always, it feels almost like a dance to Dean. He moves smoothly and easily, body sliding from one pose to the next without his mind having to be much involved at all. When he finally finishes, in Rest, he feels a hand on the back of his neck.

“Guess there’s a benefit to formal schooling after all,” Bobby muses, like he’s talking to himself. “That was beautiful, Dean.”

“Thank you,” Dean smiles into his hands, preening a little. Strong hands urge him up, then, and he goes willingly, and follows when he’s led to that big wooden cross.

He has to fight the urge down savagely to hold his arms down stiffly and ask what it is; Bobby already told him, there’ll be flogging. Sir had done that to him before, so this is just a thing to hold him up for it. And sure enough, Bobby puts his hands on some rings, and tells him to hold on.

“You move your bowels this morning, boy?” It startles him so much he jumps a little.

“Uh, yeah, after we went running.” The sharp slap on his butt makes him jump higher. “Sir! Sorry, sorry.”

“You mind that,” Bobby warns. “Few more of those gets you a punishment.”

“Yessir,” Dean hurries out, flustered. Dean’s all off kilter, still. He’s not feeling that warm, loose, anticipation like he’s used to. He’s wired, edgy, forcing himself to be in position, instead of Bobby putting him there. It’s strange and he almost feels cold, and like the wood is too sharp against his body where he’s leaning his weight on it.

Then Bobby steps up close to him, front to his back, pressed up tight.

“Relax,” he says in his ear, quietly. “I know it’s new. It’ll be different from what you’re used to. Just remember, what I say goes, boy. You’re here to please me, and right now, you’re gorgeous. Your backside is just as pretty as your front, and I’m gonna pay it some attention now. Your job is just to relax, and be good, and take what I give you.”

Dean breathes deep. He knows this. He feels his shoulders ease down, a little. Bobby’s hand dips between his cheeks, slides down his crack and nudges under his balls, his thumb presses on his hole, and Dean gasps and hitches forward, then back.

“Mmm,” Bobby hums, then steps back. “This is just a flogger, boy. Nice and heavy, no cut to it. It should warm you right up.” The trails tickle when Dean feels them running over his back and shoulders and bottom and thighs, and he squirms.

The first strike is almost gentle, diffuse. The different tails patter down like rain. Then again, across his shoulders. Again, harder, on his hips. Back and forth, one, two, one, two, a steady rhythm that starts to rock him a little against the cross. It’s almost soothing, and the burn builds in his skin before he even realizes it. The harder strokes begin to fall and pull a little cry out of him that he can’t catch, but it’s not pain, not really; like a massage, it’s sore-deep-hurt-good. Over and over, concentrating on his hips and thighs, the tails come down, and then too soon, they’re lightening, easing, and then stopping.

“Real good,” Bobby tells him, rough and quiet and close. “You took that so nice, you’re all loose and relaxed now, hm?” The hand is back between his legs, testing. “Still not real soft for me, but that’s okay. We’ll get there, boy.” The pop of a cap and cool lube pushed inside him by a probing finger has him up on his toes, such a contrast with the snapping-hot skin of his bottom, and Bobby chuckles darkly.

“Breeding bench now. Get right on up there.”

Letting go of the rings, Dean turns, only a little stiff and shaky. Bobby’s naked too, and he’s hard. His cock isn’t long, but it’s much thicker than any Dean has seen before. He gulps hard, looking at it, then moves to the breeding bench. He’s going to be a good boy.

The breeding bench is low, so Dean has to crouch down a little to get himself onto it. It has supports for his hands and knees, and a brace for his body, with padding. Once he’s on all fours he feels himself relax again, his head dropping.

“There’s a good boy,” Bobby approves. Dean’s sub brain, which is so confused right now, running in circles, trying to sink into the feeling of the flogging, jerked back by the strangeness and abruptness of it all, trying to be good for Bobby, yanked into wired alertness by nerves, relaxes a bit at the praise. “I can tell you ain’t settling, not really. Didn’t expect you to, not right away. But we’re just getting started here this morning. I’m gonna get in there and get your body started in recognizing me. Ain’t gonna be brutal, but I ain’t gonna hold back either.”

Dean shivers all over, and his sub brain calms, easing. Finally something he really knows, can anticipate, he thinks. He nods.

“Yes sir. Thank you,” he says, genuinely.

“All right. You just breathe and settle.” Dean startles a little when he feels fingers again, and more lube. Bobby’s prepping him, two fingers now, lots of lube. An itchy, unfamiliar stretch, and when he brushes Dean’s angel gland, his prostate, Dean groans and squirms his hips at the sudden, painful bondage of the cage. Three fingers follow, and Dean would hump the bench if there was anything under him, if his cock wasn’t so tightly bound. He can’t even get hard, and it’s maddening and frustrating.

“Hnnnng,” he moans, as Bobby’s fingers rub and stroke over his glands yet again.

“Please,” Dean hears himself beg, but it’s to take the cage off, and he knows that’s not happening.

“There we go,” Bobby’s voice is rich and pleased, and then he’s pressing slowly, carefully into Dean. It’s a deep stretch, nothing too rough, and Dean opens to it easily. He sighs, and puts his face down again. When Bobby starts to move, smooth in and out, slowly going deeper and deeper until he’s got a hard, steady rhythm, Dean can feel all his glands releasing calm, relaxation, feel-good ease, and he lets himself ride it. Looking for that sweet, flying, blissful place. He can’t even see the edge of it though, much less get there, so he just lets himself be rocked, lets the pleasure curl up through his pelvis and fizzle with nowhere to go, moans as it gets sharper, more intense as Bobby speeds up, really fucking him hard now.

“Good boy,” Bobby growls, and grips the back of his neck hard, and that gives Dean a lurch of sweetness, lets him drift just a little as Bobby comes, hips jerking against him, then going still. He pulls out slow, and strokes Dean’s back for a long moment, and that feels really good, really nice. Then eases Dean up from the bench carefully, looking into his eyes.

“Didn’t even come close to subspace, did you, boy,” Bobby doesn’t really make it a question, and his smile looks a little wry. Dean is suddenly worried, almost panicked, the nice warm floating feeling banished in an instant.

“I’m sorry, sir!” He babbles, frantic to make it right. “I’m really sorry, I didn’t mean--”

“Hey, hey, what’s all this?” Bobby takes his hands, then pulls him into a hug, voice concerned, face matching it. “No, boy, no. Don’t apologize. You were perfect, you did just right. That was very good, Dean, I’m well pleased with you. No, it just means we’ll need a little more practice, I’ll need to get to know you a little better like this, that’s all. Don’t you fret. Come here.” He grabs a cloth and pulls Dean down to the couch with him, not letting go as he cleans them both up, and his warm, solid presence is calming enough that Dean can convince himself Bobby’s right. He just needs more time, is all.

“For a first time, that was fantastic. You were perfect, such a wonderful boy,” Bobby keeps praising him. “So good and obedient, so sweet, I couldn’t be more pleased.” Dean relaxes, feeling himself smile. He can’t help but preen a little, hearing that. “There you are. That’s better.”

It’s surprisingly easy, after that. Bobby holds him for a while, then gives him a gentle kiss and has him go get dressed. And they go to work together, more or less like before he left for training. It’s a slow day, too, so Dean gets to find his way around the shop again, nod and say hey to the guys, figure out where everything is again. In fact, most of the day is just weirdly normal, even to the part where after dinner, he and Sam and Dad get together in Dad’s office and grab a bunch of dusty old books and start flipping through pages.

Sam just has to wreck it, of course. He pops his head up out of the book he’s reading, looking half-gleeful, half-appalled.

“Dean, oh my god. Your angel isn’t the angel of fire, or the voice of God, or the protector of the Holy Gate. Oh no, yours is the angel of THURSDAY.

Chapter Text

Sam gets it. Dad had explained that this will hopefully be a temporary thing. That a family Dominant or Submissive is really just a stop-gap, that a lot of times they were pretty low-key, short term things, historically, for youngsters to learn with, and who needed a dynamic to keep them healthy and balanced before they found a partner. Kneeling and service and some discipline, that kinda stuff. That Dean’s special circumstances are just that, and that he and Bobby are on top of it. But still, Sam’s kinda concerned. Everything in his classes talks about how important it is to find a match on your level. And Sam’s pretty sure from what he saw at Dr. Novak’s, how Dean was there, that Dad and Bobby together aren’t at Dean’s level.

So he’s pretty excited Sunday to be heading back to Dr. Novak’s with Dad and Bobby for their weird outreach-learning-whatever trip. He gets why Dad is tense, even, but mostly, Sam wants to ask Novak some questions, and see his friends.

“Sam, I want you to be quiet and stay close to us,” Dad says, for like the fourth time, and Sam rolls his eyes again.

“I played pool for three hours with Meg last time I was here, Dad,” he complains a little. “I think if she was gonna take me out, she’d have done it then.”

“Don’t you sass me,” John says, severe and cold, and Sam slumps back in the back seat of the car with a sigh. He gets it, demons are dangerous. But he’s never been allowed to go on a demon hunt, and he was still really young when they settled in Austin, after Dad’s big last hunt. And he doesn’t even remember Mom, not really. Maybe he just doesn’t know, he guesses.

“You got Dean’s notes with you?” Bobby asks, and John nods. They’d picked his brains last night for an hour or two, and written everything down. It’s astounding to imagine, but as far as Sam can tell, angels really are walking around on earth, and at least here in Texas, they’re hanging out with demons and shifters and whatever else. Sam thinks it’s fascinating. Even Dean hadn’t seemed all that freaked by it, not now, anyway, but Dad and Bobby had been all stern-faced and worried.

The familiar big house shows up in front of them, and Sam bounces a little, excited. Seriously, an angel. The metaphysical ramifications alone, when it comes to research and stuff, it’s crazy.

“Sam,” Bobby warns again, as they pull up. The short quiet guy, Crowley, Sam thinks, gets the door for them, and Sam grins at him. Bobby and John thank him absently, and they head up those long steps to the door. It’s weird to be here without Dean to welcome him, Sam realizes, just as Dr. Novak himself opens the door. Castiel, Sam reminds himself, he’d asked Sam to call him that last time.

He looks okay, Sam guesses. Maybe a little pale. But then, he’s an angel, so how would Sam know.

“Mr. Singer. John, Sam.” He nods at them all, doesn’t offer to shake.

“Call me Bobby,” Bobby insists, and gets another nod.

“As you know,” he starts right in, “the house is warded against harm to all the residents and staff. That extends to guests. But I’ll ask you to leave any weapons in the entryway, just for courtesy’s sake.” It’s polite enough, but it’s not really a request, even Sam can tell that. Dad and Bobby drop their guns without much fuss.

“Probably wouldn’t work anyway, huh?” Sam asks him, standing and watching them, and he actually smiles at Sam.

“You’re not wrong,” he admits, and oh my god, Sam wants to ask him everything. But they’re getting led through the halls off to Castiel’s office. Sam thinks he sees Benny in one of the rooms, but doesn’t even get to stop and say hello. But at least Meg is waiting for them in there, chilling on one of the couches, and Sam grins at her.

“Meg! Hey!”

“Little Winchester! How are you, how’s your big brother hanging in?”

“Sam,” Dad hauls him back, he was about to head over for his hug. He scowls.

“Come on,” he complains.

“Last warning before you wait in the car,” and that’s Dad’s all-business voice, for sure, so Sam subsides.

“Oh my.” Meg fans her face with a hand. “Masterful. Why, if I wasn’t the kind of girl who wants to take you down a peg or five, I’d be swooning right here.”

Sam snickers a little, and then snaps his mouth shut, because holy shit, is his dad blushing? Oh my god, he is! He can’t wait to tell Dean! He’s definitely not going to point it out right now, because he doesn’t want to spend the next hour or two in the car waiting, but this is the best thing ever. Dad just grumps over to the chair by Castiel’s desk and sits in it, next