Stiles can’t breathe. He thinks he must have died and gone to heaven because there is just no chance in hell that this is actually happening. Stiles Stilinski, the wimpy human who tags along with a bunch of hot, badass werewolves, can’t be kissing Derek freaking Hale . That’s just not a thing that happens.
Except it is . Derek is lying beneath him, pawing desperately at Stiles’ chest and breathing heavily. He’s rock-hard, grinding up against Stiles and whimpering , little aborted noises that he can’t seem to control. This is insane. Stiles can’t believe his life.
It all started with a stupid game of truth or dare. Erica, the demon that she is, turned on Stiles with a smirk when it was her turn to ask. Scared by her expression, Stiles said truth. Little did he know, getting dared to eat mayo or hump a pillow would have been like heaven compared to what followed.
“What is your… secret sexual fantasy?” Erica asked with a drunken giggle.
Stiles knew his answer in a second. He thought about it constantly and it even graced his dreams sometimes. Not that he’d ever admit it, not to the entire pack when they were all drunk and laughing. Instead, Stiles flushed pink and stuck his tongue out at Erica. “Sleeping with your mom,” he quipped. It earned him a playful slap to his shoulder that was still hard enough to bruise, but it accomplished his goal of escaping the question. Stiles was able to brush it under the rug and forget about it, at least until later that night.
After the pack had all disappeared to the guest rooms in Derek’s newly built house, sleepy and intoxicated, Stiles heard a knock at his door. “Yeah,” he called lazily, figuring it was Scott looking for something or Isaac wanting a roommate for the night.
When Derek entered the room, Stiles fell off the bed. His sock-clad feet tangled in the blankets and he rolled off the mattress, half-dragging his bedding with him until he hit the ground. It must have looked ridiculous, with his feet still on the bed and his body bent awkwardly to accommodate. Derek, to his credit, didn’t laugh. “What do you want?” Stiles grumbled, pouting up at the wolf.
“You never answered the question, earlier,” Derek mumbled. He kept his gaze on Stiles, even though it was obvious he wanted to look away nervously.
Stiles felt the blush creeping back up onto his cheeks. Maybe it was the tequila, or maybe so much blood rushed to his head that it popped a few blood vessels in his brain. Whatever the reason, Stiles found himself spilling the fantasy that’d been bouncing around in his head for years.
“A BDSM scene… tied up, with a spreader bar… edging until they sob… spanking... overstimulation… ready to go again…” Stiles talked and talked, describing all the things he’d been too scared to say. It felt freeing in a way he never would have expected. So lost in the words, Stiles didn’t even cast a hint of a glance at Derek until he’d finished.
The alpha’s eyes were hazy, his teeth dug into his lower lip. “Would you do that with me?”
Cut to now. Stiles is lying on top of the werewolf he’s been lusting after for months, making out with him and trying to build up the courage to do something more. The younger man knows that Derek is into it--can feel the proof pressing into his thigh--but he’s still scared. Could he really be blamed, though? Derek is scary. The boner-giving kind of scary, sure, but scary all the same.
“You’re really bad at being a dom, huh?” Derek murmurs softly, smirking and leaning his forehead against Stiles’.
“Shut up!” the younger man protests. He sits up on Derek’s waist and presses the alpha back onto the bed. Slowly, Stiles tugs Derek’s shirt off and slides down until his mouth is pressed to the newly exposed skin just above the werewolf’s jeans. With feigned confidence, he starts kissing up across Derek’s abs. The werewolf moans softly, squirming desperately for more contact. It’s ridiculous how much the tiny display of dominance from Stiles seems to have turned him on even more. Stiles can’t believe this is happening.
He starts sucking a hickey into Derek’s shoulder, even though it won’t withstand his werewolf healing. “You’d look so pretty, all marked up,” Stiles murmurs against his skin. “Is the big bad alpha all mine for the taking?” he asks, feeling ridiculous.
“Yes,” Derek pants, thrusting his hips up desperately. “Please, Stiles,” he begs. “Do something, please .”
Really, how can Stiles say no to that? He rolls over to sit next to Derek on the bed, slowly dancing his fingers down the werewolf’s chest until he reaches his jeans. Stiles slides them down, brushing his fingers along Derek’s bare skin as it’s exposed. By the time the pants are off, the alpha is panting. His boxers are tented obscenely. “Do you want these off, sweetheart?” Stiles asks, his voice fond. Derek nods frantically. Teasing and slow, Stiles tugs the boxers down with his teeth. Derek throws back his head with a loud moan. Once the silk ( silk !) boxers are past his knees, Stiles pulls them the rest of the way off with his hands before he feels too much like a dog with a chew toy.
Derek is completely naked, sprawled out across the bed like a living wet dream. Stiles needs a minute to breathe. Derek freaking Hale wants Stiles to dominate him. “Please,” the alpha whimpers, arching his hips up and looking at the younger man desperately. “Stiles, please .”
“What do you want, babe?” Stiles asks teasingly. Though it comes across as a tease, it’s actually a stall; Stiles desperately wants to touch but he’s nervous . He’s just waiting for Derek to inevitably push him away in disgust.
“What you said,” Derek pants, squirming. “Everything you said.” Sudden heat pools in Stiles’ stomach and he whimpers quietly. Derek bites his lip harshly.
Stiles wraps his hand around the alpha’s dick and Derek yells . He bucks and his toes curl against the mussed quilt, deft fingers scrabbling desperately for purchase against the bed. “Yes, Stiles, god, please, yes, oh, more,” he babbles, voice soft and desperate.
Stiles takes his hand away. Derek growls and whimpers and pleads, all in the same stream of breath. “ Stiles ,” he breathes.
“Sorry, darling,” Stiles coos without any remorse. Derek growls softly and Stiles smacks his thigh in punishment. The alpha moans , his cock twitching. “Oh, you like that, baby?” Stiles teases, pushing away the feeling that he’s the star in a bad porno when Derek nods with a blush. Smirking, Stiles leans down and blows softly on the alpha’s red, flushed dick. Derek lets out a choked noise of surprise. Eyes wide, Stiles watches as his claws extend and slice thin scratches into the sheets. “Look at these pretty claws,” he coos, breath streaming against Derek’s twitching cock. “You’re so stunning, baby.”
It seems that Derek can’t even take a compliment in the bedroom. “Shut up,” he groans, hips making little aborted thrusts.
Stiles darts his tongue out and licks the head of his cock. Moaning loudly, Derek slams one hand against the bed and throws his head back against the pillows. Stiles pulls back an inch and returns to blowing softly on the werewolf’s now-damp skin. Derek is positively shivering. “Stiles,” he pleads, sounding increasingly frustrated. “Hurry the fuck up and touch me, please .”
Stiles sits up and crosses his arms, earning a miserable groan. “You don’t tell me what to do, sweetheart,” he says, sounding as stern as he can manage. Smoothly, Stiles slides to the edge of the bed until his legs hang over the side. He pats his lap and looks at Derek expectantly.
The alpha flushes pink and slowly crawls over to position himself. “Hurry it up,” Stiles orders, slapping the soft, pale skin between Derek’s ass and thigh. The werewolf jolts and gets pinker, quickly lying across Stiles’ lap with his ass up. “Okay,” Stiles says softly, staring at the gorgeously intimidating expanse of Derek’s skin. “I know ‘stop, ow, stop’ is kind of the implied safeword right now,” he starts, “but we need a proper safeword too. Something you can remember easily when you need the scene to stop.”
Derek won’t stop squirming. Stiles isn’t sure the older man even knows he’s doing it, subtly rocking his dick against Stiles’ thigh. It’s distracting and makes the student want to dive right into more fun activities, but he can’t spell ‘fun’ without multiple letters from ‘safeword negotiation.’
“How ‘bout moon?” Stiles asks. “We talk about the moon a lot, right? Can you remember moon? Is it okay? Don’t agree just because. Pick a better word if you want. This is important,” Stiles rambles. He rubs the werewolf’s back absentmindedly as he speaks.
“Moon,” Derek repeats. Thankfully, he sounds like he’s testing it out, not speaking sceptically. “It’s kind of obvious, but it works.”
Stiles smacks him hard enough to make Derek’s left ass cheek tinge pink. “Stop criticizing my safeword suggestions,” he snaps, impressed with himself when he doesn’t come across as whiny. “Don’t be disrespectful. Do you agree that moon is the safeword, then? You’re sure?” he asks, gentling his tone. Derek nods, murmurs his assent.
“Can you touch me now, please?” he begs softly. His squirming is consistent now, quick rutting against Stiles’ thigh that has the alpha breathing shakily. Stiles lands a spank on his right cheek, digging his nails in to make the stinging last longer. Derek moans, bucking against his thigh.
“How many?” Stiles asks, pulling one cheek to the side and slapping Derek’s soft pucker. The alpha chokes and moans, his toes curling tightly. He doesn’t reply. “How--many?” Stiles repeats, accompanying each word with a slap. “Enough to break your werewolf healing so you’ll still feel it tomorrow?” he asks, leaning down to bite the back of Derek’s shoulder.
“Thirty,” the alpha offers tentatively. He groans when Stiles hits him hard enough to press his dick into the younger man’s thigh.
“Count,” Stiles orders. He slides a finger across Derek’s crack, just to watch the werewolf shiver. Carefully, the student lands his next spank to hit both of Derek’s muscled thighs and ass, all at once.
“Five,” the submissive pants.
“Don’t cheat,” Stiles growls. “Start at one,” he instructs, landing three slaps in quick succession. They’re littered across Derek’s ass, staining it pink for mere moments before he heals.
“One, two, three,” Derek pants. He’s still squirming. Stiles distracts himself by spanking him again, all power and no speed. It makes him extra aware of just how big Derek is when the alpha’s cock presses into his thigh. “Four!” Derek cries. He digs his claws into the already-ripped bedspread, making a series of happy pain noises. Stiles keeps hitting him, fast enough to make it ache even through Derek’s healing. The werewolf’s words slur into each other like melting ice cream, struggling to count fast enough. It might be the hottest thing Stiles has ever heard; enough so that he’s able to push through the ache in his tired arm to slap until Derek sobs out, “Thirty!”
Stiles pulls him up and cradles the werewolf to his chest. Gently, he rubs Derek’s sweaty back and presses gentle kisses to the corners of his pretty, pretty eyes where it looks like tears may or may not have the possibility of forming. Even though the werewolf has gone through so much pain and stood strong each time, Stiles know subbing is a completely different ball game (heh, ball game). It’s consensually letting and wanting someone to hurt him.
“Are you okay?” Stiles asks, scooching further onto the bed with Derek wrapped in his arms. “Do you still want to keep going?” Suddenly, Stiles wonders if Derek is even enjoying himself. Maybe he’s deluding himself and Derek isn’t even in mild sub-space; maybe sex with Stiles is just so awful that it’s enough to bring a glassiness to the unshakeable, badass alpha’s eyes.
Oh, god. Stiles gently lets go of the werewolf and pulls away, giving him some room to politely walk away and forget this ever happened. If Stiles ever gets over the crushing embarrassment and shame and guilt, this could make for some amazing material to jerk-off to.
Derek whimpers. It’s soft and he turns bright red afterwards, but it’s enough for Stiles to know that the older man is, in fact, in a mild sub-space. He tugs him close again, petting the shorter, scratchy hairs at the back of Derek’s head that are free of gel. “Okay,” the wolf murmurs after a few moments. “Keep going. I’m fine.” Stiles looks at him assessingly for a few moments.
“Okay,” he agrees. “You’re such a good boy,” he promises, rubbing Derek’s shoulders and gently laying him out in the middle of the bed. “I’m gonna tie you up, alright?”
The werewolf punches him in the shoulder. “Stop being so gentle with me. I’m fine.” Stiles glares.
“You know you’re getting punished for hitting me,” the student says. He gets to his feet, walking to the closet where he’s been hiding his kinky online purchases from his dad. Derek’s decision to give each pack-member their own room and key to the house, doors open whenever they needed a place, is turning out to be the saviour of the night. Even though Stiles is single and had never even voiced his BDSM fantasy until tonight, he owns an embarrassing amount of sex toys made for two. He pulls out padded handcuffs and a spreader bar, quickly binding Derek to the headboard and buckling the bar between his feet.
Once he’s bound, Stiles turns back to the closet for another tool. The sight of it makes Derek’s cock jump .
Derek is shaking. Even with wolf healing, he swears he can still feel the burn in his ass and it hurts so good. The cuffs are solid around his wrists; padded and comfortable but strong enough that he would have to half-turn to break free. In this state, with his rock-hard dick swaying as he squirms uncontrollably, Derek isn’t sure he’d be able to manage enough control to do it. The powerless feeling is something that should strike fear in him, enough to make him go soft. If it was anyone else except for Stiles, looming above him with that in their hands, Derek would probably be about as far from aroused as he could get.
But it is Stiles looming above him. Derek is so turned on he might pass out or choke or something equally embarrassing.
“This is a Wartenburg wheel,” Stiles informs, holding up the small metal tool with blunt spikes protruding from a spinning circle attached to a handle. Stiles spins it and glides it across his palm to demonstrate.
“I know,” Derek replies softly, feeling his dick jerk excitedly. He knows it’s a punishment. The spikes gliding along his erogenous zones is going to hurt and he shouldn’t be this excited for it. The werewolf might regret it when Stiles starts, but right now all he can feel is his arousal ratcheting up impossibly higher.
When Stiles runs the spinning, spiky wheel across his abs, Derek jumps. His stomach twitches and the cuffs rattle noisily in sync with his low groan. It hurts more than he expected but it tickles, too. Stiles rolls it up his stomach, in long lines up and down his pecs until he hits Derek’s nipples. There’s hardly any teasing, no torturous slow build that Derek has quickly learned to expect from Stiles.
The alpha arches with a yelp, testing the absolute limit of his cuffs. His body can’t seem to decide whether it feels mainly painful or ticklish or erotic. He moans and whimpers and grunts, writhing and occasionally panting out Stiles’ name. Stiles lifts the pinwheel from one nipple and moves it to the other, lowering his mouth to soothe with smooth laves of his tongue. It’s torturous how amazing it feels; amazing how torturous it is. Derek isn’t sure how long it goes on, the slow drags of the wheel and soft licks. What he does know is that, by the end of it, he can’t stop making noise. Moans and cries and pleads and babbling; he isn’t sure whether he’s grateful or not that Stiles doesn’t seem to be a fan of gags.
Finally, the younger man stops. With one last assessing look at Derek’s chest, he leans over to the cluttered nightstand and drops the pinwheel on it. If he was blindfolded, Derek wonders if he would still think the Wartenberg wheel was touching him. Everywhere the spikes touched him, he can still feel it. Even under the ministrations of Stiles’ tongue, red hot lines of painful bliss feel like they’ve been pressed into his skin.
“Still okay?” the human asks softly. Derek nods. “Okay. I’m going to put a vibrator up your ass and suck your dick while you wear a cock ring,” he says simply. Derek shivers. Stiles walks back to the closet and grabs a large silicone toy. It’s a vibrator, attached to two rings-- presumably to wrap around Derek’s balls and the base of his dick. “Prostate massager,” Stiles says, pointing at the vibrator. Next, he points at the rings and continues, “To help keep you on the edge, desperate and wanting.” The way Stiles says it is positively obscene. Derek’s dick jumps.
“You’re unfair,” he groans.
“Be quiet,” Stiles replies, crawling onto the werewolf’s waist with the toy. “Suck,” he orders, pressing the massager between Derek’s lips. It’s humiliating, but it’s even more embarrassing how much harder the humiliation makes the alpha. He moans softly around the soft silicone. “So pretty,” Stiles murmurs, gently stroking the stubbly sides of Derek’s face. “Hold this,” he instructs, unlocking and guiding the werewolf’s hand to the vibrator. Derek’s gaze follows the younger man as Stiles slides down his body, licking tantalizingly around the base of his dick. A whimper falls from the werewolf’s lips. So distracted by Stiles’ soft pink mouth, he doesn’t notice the pretty boy grabbing a bottle of lube until the cap clicks open. “ ‘M gonna finger you.”
Stiles hits his prostate almost immediately. Derek has to pull the vibrator out of his mouth to let out a screaming moan without choking. “Hey,” Stiles snaps, smacking his ass. “Did I give you permission to do that?” It takes the werewolf a moment to catch up; Stiles is still rubbing his prostate gently. When he does, Derek is quick to slide the vibrator back between his lips. The younger man stares at him for a moment, before landing another slap on his ass.
He doesn’t remove the toy until Derek’s jaw is starting to ache and Stiles has four fingers comfortably scissoring him. It feels amazing, the occasional bumps against his prostate like a quick trip to heaven, but it’s not enough . Derek can’t stop moaning, even around the prostate massager.
“Ready?” Stiles asks, taking the toy. He locks the handcuffs back around the werewolf’s wrist. A thin line of saliva connects Derek to the silicone. Before the werewolf has a chance to respond, Stiles dribbles a tiny amount of lube on the cock ring and slides it down with an ease that’s just not realistic at all.
“Have you done this before?”
“I switch,” Stiles says, focusing intensely as he slides the second ring around Derek’s balls and rubs teasingly at his perineum. “Like, between dom and sub and top/bottom. So I use my toys on myself.” Derek doesn’t get a chance to reply.
In one smooth slide, Stiles presses the massager in. He switches it on when the toy is three quarters of the way in, and Derek lets out a yelp that quickly evolves into a moan. Stiles sits next to him on the bed to watch, rubbing at his clothed dick absently.
The vibrations are a constant, insistent buzz against his prostate. It feels like pure heaven for the first few minutes. Derek moans and bucks into the empty air, babbling curses that could make a sailor cry. It’s the most intense pleasure he’s ever experienced in his whole life . Soon, he feels his orgasm starting to build. It’s a delicious curl of warmth in his lower stomach that builds until he can’t even speak, it feels so good.
“God, you’re beautiful,” Stiles mumbles. He speaks soft enough that Derek is almost positive he wasn’t meant to hear. However, it’s enough to make him realize that he’s sprouted claws and fangs. Before he has the chance to draw them back in, Stiles changes the setting on the vibrator. The insistent buzzing turns into quick pulses that feel like they’re shaking Derek down to his core.
His orgasm builds even faster, until he’s on the verge of coming--except he can’t . Stuck on the edge, pleasure is quickly edged with overstimulation as Derek writhes on the bed like a man possessed.
Stiles wraps his lips around the werewolf’s cock and sinks down to the base until he’s deep-throating him like it’s nothing. For half a second, Derek chokes on his whimpers and moans and feels like he can’t catch a breath. Then Stiles swallows and hums, and Derek wails . He’d always thought himself to be the type of person to swear through his pleasure, at least until he got into bed with Stiles. All he can feel is Stiles’ mouth on his cock, the vibrating prostate massager in his ass.
Derek is growling . His claws are out and his teeth protrude from his mouth and Stiles really shouldn’t be finding all this so fucking hot. However, he’s doing a BDSM scene with an alpha werewolf who’s nearly ten years older than him. Stiles doesn’t even know Derek’s middle name . Burning arousal fuelled by a few wolfy reactions is pretty low on the fucked up totem pole of Stiles’ life.
It takes him a moment to realize that he’s humping the edge of the bed. The low position, lying between Derek’s legs, places Stiles’ torso and groin on the bottom half of the bed, bent at the waist with his toes touching the floor. The friction is perfect at first, just enough to satisfy himself until he can get inside Derek. Really, the clank of the alpha’s handcuffs and his low, desperate growls, along with his cock in Stiles’ mouth is enough to keep the younger man rock-hard. He’s harder than he’s ever been in his life. For a horny teenager who spends all his time with attractive werewolves, that’s saying a lot.
When Derek roars with frustration and tapers off into pathetic, pleading whimpers, it’s nearly enough to have Stiles coming in his pants. Cruelly, he pulls of the werewolf’s dick with one long suck, tonguing around the head for a few seconds. It’s enough to make Derek rattle the padded cuffs until Stiles is worried that, even though he reinforced them, the metal is going to snap. “Break the cuffs and I won’t let you finish until I’ve come at least ten times,” he threatens, dragging his lips along Derek’s inner thigh as he speaks. He decides not to tell the wolf that, in high school, Stiles once came seven times in two hours when his dad was caught at work and he’d been granted a blissfully homework-free weekend.
Derek’s arms falls still. He doesn’t relax--broad shoulders still tense, thighs still quivering under Stiles’ touch and hips bucking uncontrollably--but he’s not full-out writhing, at least. Stiles rewards him with a quick lick across the crown of his dick. Ironically, it makes Derek arch and squirm wildly for thirty-seven seconds (Stiles counts). “Are you mumbling numbers while fucking edging me?” Derek asks. There’s really nothing Stiles can say that in some way re-establishes his position as the dom in the-- is it a relationship? Instead, he slaps Derek’s ass.
“Want me to fuck you?” Stiles asks, intentionally schooling his voice until he sounds like he’s merely asking if Derek wants him to pick up a pizza.
The alpha is babbling yes and pleading desperately before Stiles has finished speaking. “Stiles, please, yes, I need it, need you right now, in me, please, Stiles, please .”
Finally, finally , Stiles starts removing his clothes. Derek might be salivating, but he’s too drunk on pleasure and frustration to know for sure. The ridiculous hoodie-flannel-t-shirt combination goes first, hitting the floor in a heap. Already, Derek finds himself hoping Stiles will forget something here so he can creepily smell it later; he already knows everything will reek of honey-sweet arousal. Half-shifted, he can smell the scent triple in strength when Stiles slides out of his jeans. Derek can’t stop himself from groaning, not that he was exactly trying all too hard to stifle himself.
When Stiles pushes his boxers down his thighs, his cock slaps up against his stomach and sends a wave of thick, syrupy arousal in Derek’s direction. The werewolf squirms and tugs at his wrists until the clatter of the handcuffs remind him of the younger man’s threat.
Stiles, thankfully, doesn’t tease any longer. He hurriedly rubs some lube on his cock and grabs Derek’s knees to drag him to the edge of the bed, rapidly removing the spreader bar and throwing the wolf’s legs over his shoulder. Honestly, Derek doesn’t understand where the younger man got the strength from but he’s quickly distracted when Stiles removes the prostate massager and slides home in one smooth motion.
Of course Stiles would hit his prostate on the first try because, as much as he refuses to admit it, the younger man is ridiculously good at practically everything . If not for the rings, Derek just knows he would be coming already. He groans, a mix of intense pleasure and unbelievable frustration. “Fuck, Stiles, let me come, please,” the alpha pleads, digging his feet into Stiles’ shoulders. The beautiful freckled boy doesn’t reply, at least not verbally. Instead, he thrusts harder, pounding into Derek until the werewolf can hear the bed rocking against the wall. He can’t even bring himself to care ; everything in his life narrows down to Stiles’ cock in his ass, the younger man’s hands on his thighs.
“You can come now but I’m not going to stop,” Stiles threatens. It takes a moment for the meaning to click in Derek’s brain. He can choose to come now or later, but Stiles is going to keep pleasuring him either way.
The alpha doesn’t even spare a second to consider his options. “Now, now, Stiles, please, fuck, let me come, babe, please,” he begs, toes curling against Stiles’ back. Smirking, like he was expecting that answer, Stiles leans over to share a sloppy, delicious kiss with Derek. “ Please ,” the alpha groans. Stiles removes the rings, topping it off with one brutal thrust that hits Derek’s prostate dead-on.
The werewolf comes with a scream. A loud crack! vaguely registers at the back of his mind, hidden away behind a thick wave of pleasure as his orgasm strikes him gloriously, hitting him with pleasure that reaches down to his toes. He moans and curses and growls, babbling sweet, overwhelmed nonsense at Stiles. Jizz hits his own stomach and Stiles’ chest, a small drop even landing on the human’s lush lower lip. When Stiles licks it into his mouth, slow and lascivious, Derek feels his dick twitch weakly.
Stiles doesn’t even slow his thrusts, even going as far as reaching between them to jerk Derek’s sensitive cock. “Fuck!” the alpha shrieks, embarrassingly high-pitched as he squirms desperately. “It’s too much, uh, Stiles, fuck, fuck, ah,” Derek whimpers, nearly breaking his damn legs as he struggles to push himself away from Stiles.
“Stay still,” the younger man growls, slapping Derek’s sensitive inner thighs. Softly, he murmurs, “Remember your safeword?” The alpha nods, groaning softly.
He can’t stop squirming, no matter how much he wants to be good for Stiles. The pretty boy keeps rutting into him and jerking his dick insistently until Derek is screaming from it. “You make such pretty noises,” Stiles murmurs fondly, his voice starting to sound shaky and uneven as his climax builds.
“ ‘M gonna come,” he warns, giving Derek one firm stroke before he’s slamming into him with a long groan. “Fuck, Der, so good, so good for me,” he pants, collapsing on top of the muscular werewolf. It presses Derek’s thighs against his stomach uncomfortably; he groans his complaint, kissing Stiles’ pretty mouth anyways. The dom pulls up and adjusts Derek’s legs until they can both comfortably sprawl across the bed and exchange lazy, open-mouthed kisses. Even though his dick is pressed between their stomachs in a way that’s over-sensitive, Derek is able to distract himself with the sleepy makeout session. At least, until Stiles wraps a callused hand around his dick and starts jerking him, sudden and fast.
“Fuck!” Derek cries out, arching away from him and into the bed. The few times he’d tried to overstimulate himself had lasted all of a few seconds before he gave up. Stiles, on the other hand, jerks him brutally fast and without mercy. It hurts so good . “Too much,” he whimpers, although he carefully slots his safeword in the back of his mind without using it.
“Sorry, babe,” Stiles murmurs. Contradictory person that he is, he accompanies the apology by sliding the prostate massager back into Derek’s ass. He switches it onto the highest setting, because Stiles Stilinski is cruel . Derek might love him anyways, just a little bit.
“It’s too much,” he yelps, pawing at Stiles’ back. With a jolt, Derek realizes the crack he’d distantly heard while coming was the snap of his handcuffs. Shit. Stiles gives him a shark-like smirk, jerking Derek rapidly with one hand and thumbing at his slit with the other. “ Stiles ,” the alpha gasps, writhing desperately. He’s hard enough to cut diamonds and it hurts like heaven. Thankfully, Stiles doesn’t slide the rings back on.
“Since you decided to break the cuffs, you can use your hands to jerk yourself without coming,” he orders, releasing his hold on Derek’s shaft. “Or I’ll grab the Hitachi wand.” With a full-body shudder, Derek manages to retract his claws and slide a shaky hand around himself.
“Fuck!” he groans, loosening the grip until he’s barely touching himself. Stiles rubs at the head of the wolf’s cock until Derek yells louder than Lydia’s banshee-scream. Thank fuck, Stiles releases his grip after less than a minute--although it feels like a damn lifetime. He doesn’t even need to speak before Derek is grasping his own dick, desperate to avoid anymore overstimulating torture. Stiles sits back to watch, rubbing his own nipples as he slowly recuperates. Derek’s breath catches. The wolf in him desperately wants to roll them over and lick the pretty younger man’s chest until he screams. Absently, he thinks back to Stiles admitting that he switches. “Stiles, please,” he groans, desperate to get off from something other than the oversensitive hand on his cock. “Need you inside me.”
Stiles huffs and reaches out a hand to rub Derek’s pecs. “D’you want me to keep jacking you until I’m ready for another round or do you want to wear nipple clamps?” The werewolf can’t help himself from the low moan that drops from his lips.
“Clamps,” he replies, soft and growly. Stiles smirks, clambering off the bed with his usual lack of grace and grabs a set of clamps with a chain connecting them. Wearing a half-smile all the while, he carefully attaches the small clips. They’re pure metal without the latex tips that Derek had expected. Thin screws allow Stiles to control the tension; the clamps must be on their loosest setting but it still burns .
Derek is still jacking himself, gentle and loosely now. Oversensitivity is slowly leading into red velvet pleasure that slides across his skin deliciously. The pain has lessened, from excruciating to bearable to something on the verge of exquisite . “Since you’re enjoying that now, I guess I’ll just have to make the clamps extra tight,” Stiles murmurs, sliding the pads of his fingers across Derek’s hand and thumbing the head of his dick. It’s enough to make the wolf arch with a long, breathy noise.
True to his word, Stiles spins the screws in three full rotations without allowing Derek a moment to adjust. “Fuck!” the alpha growls, writhing wildly and curling his toes into the bed. The movement makes the chain swing and only serves to increase the pain. Quickly, Derek learns to lie still on the bed, although the chain still sways gently. The burning slowly eases into a deep ache and his breathing evens out into a steady pattern. Breathe in, out. Swing forwards, back.
Time passes surprisingly quickly, or maybe Stiles just has an incredibly impressive refractory period. Either way, the younger man soon crawls to sit on Derek’s waist with his dick half-hard. “Wanna suck me?” he asks.
“God, yes,” Derek breathes out immediately, resisting the urge to grab Stiles’ soft thighs and edge the boy close enough to wrap his mouth around him. Thankfully, Stiles repositions them until Derek is comfortable. Immediately, even though he feels like he should ask for some sort of permission, Derek sinks down around Stiles’ cock. Using every last trick and technique he’s picked up over the years, Derek gives him the sloppiest blow job he can manage.
“Fuck, Der, you’re so perfect,” Stiles hums, tugging at the alpha’s hair. “That feels amazing , babe,” he moans, with a stream of pleased noises. Already, Derek can feel Stiles getting harder. The harder he sucks, the more Stiles relaxes into him until the pretty boy is still, save for the rapid praise falling from his mouth. (“Such a good boy, so good for me, baby. Just like that, you’re so good, so perfect, babe.”) Whenever Stiles isn’t still, rocking gently into Derek’s mouth, he bumps the clamps and makes the chain swing. It’s enough to drive a man mad--even a man that’s half-wolf.
Thankfully, just as Derek’s jaw is starting to ache and he’s wondering if it’s possible to strain a tongue muscle, Stiles crawls off him. With quick precision, the dom slides a condom on and removes the prostate massager that only half-registers in Derek’s hazy mind. He moans anyways. “Fuck me, please, Stiles, please, fuck me,” he babbles, arching and bucking.
“Shh, sweetheart,” Stiles hums, soothingly rubbing Derek’s thigh. He’s all too good at taking Derek apart and putting him back together. As soon as the alpha is relaxed enough to breathe normally, Stiles thrusts into him in one smooth slide. Derek throws his head back with a yell, toes curling. Stiles’ cock hits all the places that the toy didn’t, stretching the werewolf in a way that feels amazing .
“Fuck!” he cries, quickly devolving into unintelligible moans and whimpers and grunts. Stiles fucks him through it all, alternating between hard, deep thrusts and short, quick ones. Somehow, he manages to nail Derek’s prostate almost every time. It’s inevitable when the wolf can feel his climax building shortly. Based on the way Stiles starts to rut more desperately, grunting praise into Derek’s ears, the dom is close too. “Fuck, yes, I love you, so good, Stiles !” Derek screams, pawing desperately at Stiles’ shoulder as they both come in sync.
“ Derek ,” Stiles groans back, falling next to him on the bed.