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“It was nice seeing you again Sheriff,” Derek held his right hand out to John as he wrapped his left arm around Stiles' waist, holding his boyfriend against his side.

“You as well Derek, thank you for bringing Stiles over for dinner I know he is a bit of a handful.” John chuckled as Stiles stuck his tongue out at his father playfully as his father and lover shook hands firmly.

“I think I have him well in hand by now.” Derek joked and John chuckled again as he bid the couple farewell after their afternoon together that including a painfully healthy dinner made by Stiles.

“Bye dad, see you next week.” Stiles hugged his father before lacing his fingers together with Derek’s and the two headed to Derek’s black Camaro. John waved them off as the car revved and turned down the street; he was glad that after everything those two had found each other.

“You did real good tonight baby, if I hadn’t known beforehand I would have never guessed.” Derek praised as he laid his hand on Stiles' thigh as he kept his eyes on the road.

“Thanks, Derek,” Stiles murmured and inhaled sharply when Derek tightened his grip. “Sorry, I mean thank you, Sir.”

“I’ll let that slip, for now, I know it’s hard to get back into that headspace after spending time with your dad,” Derek said patiently as he turned down the road that would lead to the preserve where the rebuild Hale house was waiting for them. Stiles and Derek were the only ones to live there, the others came by for Pack training, meetings and what not but it was Stiles and Derek’s home.

“Thank you, Sir,” Stiles settled down in the seat, after shifting his weight around a bit like he was trying to get comfortable.

“It’s a nice night, should we go for a walk down to the lake tonight?” Derek asked, eyeing Stiles and had to fight back a smile when Stiles' eyes went wide and almost panicked.

“Not tonight Sir, please. I’ve been so good, please.” Stiles gripped Derek’s hand as he spread his legs wider as he spoke. Stiles let out a shuddering breath when Derek slid his hand up and cupped his lover’s growing erection from above his jeans.

“You have been good baby, how about you go and wait for me upstairs and we’ll have some fun hm?” Derek crooned as he parked the car next to a few other cars in the overhang that acted as a garage.

“Yes Sir, thank you.” Stiles’ face lit up and he leaned over for a chaste kiss before he shot out of the car and up the steps of the porch and into their home. Derek smiled fondly at the sight, he would never get used to that. Derek cut the engine and slowly pulled himself out of the driver's seat and headed up into the house. His eyes flashed red as his inner wolf growled as the aroused scent of Stiles wafted throughout the house. Derek fought the urge to just run up to their bedroom and bury himself in Stiles and his scent; he was going to take his time.

Derek finally made it to their master bedroom and had to adjust his jeans as his cock began to stiffen at the sight that awaited him. Stiles’ was in the middle of their large bed, completely naked. His head was down, resting on a pillow and his knees parted wide with his slender fingers gripped his bare ass cheeks, holding them apart, presenting himself to Derek.

“Such a pretty sight,” Derek tossed his shirt off over his head and onto the ground as he joined Stiles on the mattress.

“Thank you, Sir,” Stiles’ breathing hitched at the praise and Derek took hold of Stiles ass cheeks and smiled when Stiles let his arms cross in the small of his back in perfect obedience. Obedience that would never fail to surprise and please Derek since the moment they had stumbled upon their shared kinks and then entered their Dom/sub relationship.

“Good boy,” Derek murmured as he took in the sight of Stiles pucker, it had closed up since before their afternoon with Stiles dad, but Derek could still see the bright red of the strand of anal beads he had worked into Stiles beforehand.

“You had all of these beads inside of you during the entire afternoon and not once did you let on. You are amazing baby, so perfect.” Derek crooned as he leaned down and dragged his tongue around Stiles’ hole, smiling at the little moan Stiles gave at the action. Derek kneaded Stiles’ ass cheeks as he sucked and licked at Stiles’ hole until it was loosening and relaxing. Derek leaned back and hook his finger through the small rubber ring that was hanging down from Stiles hole, it had left an indent in Stiles upper back thigh but neither seemed to mind it.

“Do you remember our rule when it comes to this toy?” Derek asked as he lightly pulled at the ring, applying pressure to the beads inside of Stiles body.

“Y-Yes Sir, I am only allowed to come if I come to you pulling these out if I don’t then I am not allowed to come at all tonight,” Stiles repeated, the idea had been his and Derek had been in agreement, either way, he got to see one of Stiles’ amazing faces and noises. Either if he came or when he was denied all night, both Derek adored and treasured.

“Very good baby, now relax for me.” Derek soothed as he adjusted his grip on the end of the strand of beads and sitting back on his knees he began to pull. Stiles gasped into the pillow and curled his fingers into fists and his toes into the sheets below him. His cock was aching between his thighs and he could feel a bead of pre-cum beginning to drip out of the slit.

Derek watched as the first bead slowly inched its way out of Stiles, he was going slow as he knew that if he pulled them out too fast Stiles would come just from the first bead being pulled out. Derek wanted to at least make it a bit more challenging tonight.

Stiles let out a keening noise as the first and largest bead popped out of him with a lewd squelching noise. Stiles’ skin broke out into goosebumps as he felt the next bead began to be pulled out. Stiles bit into the pillow as he closed his eyes and made a muffled noise as the next bead slipped free of him, he could feel his hole clenching and he could also feel the heat of Derek’s eyes on it making his cheeks flame.

“Last one baby, if you want to come you better do it soon.” Derek’s voice floated into Stiles’ head and Stiles’ mouth released its hold on the pillow and instead, he swallowed the salvia that was threatening to fall from his parted lips. He was so hard it hurt and he knew he had one final chance to come tonight or he would be submitted to Derek’s teasing all night while he was unable to come. Stiles let out a surprised cry as the last bead was yanked out of him and he silently praised God as he felt his orgasm wash over him intensely. His eyes rolling up into his head as he slumped down onto the mattress, panting for breath as his vision blacked out.

“That’s my good boy.” Derek murmured as he set the strand of anal beads down and cuddled Stiles limp form against his own body, holding him close. Derek took his lover’s pulse and brushing his damp hair off of his forehead and peppering his face with little kisses.

“S-Sir?” Stiles asked hazily when his eyes finally fluttered open.

“You did so well for me Stiles, now just rest okay? You had a long day after all.” Derek said lovingly as he leaned down and kissed Stiles lightly before resting their foreheads together.

“Mm, yes Sir,” Stiles smiled happily and curled closer to Derek. His scent full of love, happiness and trust that cocooned around the two of them as they lay together in their bed.

This was what Derek had been missing for all those years, in all those other relationships and he knew that Stiles was the one for him for now and ever more.

Chapter Text

“Color?” Derek asked as he lightly dragged the tips of his nails down Stiles bare chest. The younger man wiggled his wrists from where they were cuffed to the headboard above his head and did the same to the cuffs that were keeping his legs spread wide and attached to the footboard.

“Green Sir,” Stiles decided firmly and smiled happily when Derek kissed him in response.

“You’re going to be good for me tonight aren’t you baby?” Derek crooned when their kiss broke and he cupped Stiles’ cheek as he spoke.

“I’ll try Sir,” Stiles said honestly.

“I know you will baby,” Derek hummed, pleased that Stiles was past the point of quickly agreeing because in most cases he wasn’t and that ended with punishment for lying. Derek kissed Stiles lightly before he sat on the edge of the bed and picked up a small bowl that was filled with ice cubes. Stiles tracked his movements, absently licking his lips as Derek picked up one of the ice cubes. When the two talked about temperature play, the heat had been quickly discarded and Derek admitted he didn’t really feel the cold but Stiles was willing to try.

Stiles’ lips parted and a sharp exhale fell from between them when Derek dragged the cube over his lower lip and Stiles felt goosebumps already beginning to form. Derek was watching Stiles’ reactions very closely as he slowly dragged the now melting cube of ice over Stiles plush lips. Derek pushed the remaining ice into Stiles’ mouth and rolled his eyes fondly as the human sucked on it loudly.

“Just a bit of ice and it looks like you’ve been sucking cock all day long,” Derek commented as he took in the sight of Stiles red and slightly swelling lips.

“Is that a promise Sir?” Stiles batted his eyelashes and Derek patted his cheek gently.

“Maybe if you’re really good for me.” Derek teased earning a pout before he picked up another ice cube. Stiles let out a small breath of air when Derek dragged the tip down his neck and spread the cool water across his collarbone. Stiles moaned outright when Derek leaned down and followed the wet path with his burning hot tongue. Stiles tugged against the cuffs as his cock twitched with arousal as his body shuddered under the sudden contrast of cold and heat.

Derek picked up another ice cube as he watched Stiles shudder and pant from his place spread out on the bed. Derek pressed the flat side of the cube against Stiles right nipple and with his free hand; he palmed his swelling cock as Stiles let out a little mewl as his chest arched under the sudden chill of the ice.

“Nnggh,” Stiles gasped as Derek twisted the ice cube around and dragged it around the now hardened nub, it was so cold it hurt but it was a good hurt and Stiles could feel a bead of pre-cum slipping down the side of his cock. Derek smiled as he rubbed the melting cube over Stiles' chest and pressed it to Stiles’ left nipple before sealing his mouth around it.

Stiles let out a cry as his body shook under the sudden mix of cold from the ice and the heat of Derek’s mouth. His eyes fluttered and he tugged harder at the cuffs around his wrists and ankles unable to stop himself. Derek licked and sucked at the ice until it was melted before he removed his mouth from Stiles nipple.

“Color?” Derek questioned and Stiles panted for a moment before replying.

“Green Sir just was intense.”

“That’s the point baby, are you okay to keep going?” Derek asked as he drew a circle on Stiles' stomach comfortingly with his index finger.

“Yes Sir,” Stiles nodded after a moment of thought and sighed when Derek kissed him again.

“That’s my good boy,” Derek crooned and smirked at the delicate flush that covered Stiles cheeks at the praise and the increase of the younger man’s arousal. Derek picked up one of the larger cubes of ice as he kissed a path down Stiles chest and stomach until he came to the human’s fully erect cock.

Derek positioned himself so he was kneeling between Stiles’ spread legs and locked eyes with Stiles just as he pressed the tip of the ice against his lover’s slit. Stiles let out a choked out a cry as his hips jerked up at the intensity of the ice pressing against the sensitive tip of his cock. Derek rubbed the ice around the head a couple of times before he began to slide it up and down the hard shaft as he used the tip of his tongue to tease the cold skin.

Stiles' legs thrashed in their cuffs and he was hiding his face in his arm as he groaned and gave little cries of pleasure as Derek teased his cock with the ice. Stiles let out a little sob when Derek applied the ice to his balls and he felt them tighten up, his orgasm somehow coiling up in his gut.

“Sir, oh fuck, I’m so close!” Stiles managed to choke out a warning, knowing it was a rule of Derek’s for the night and he let out a sob when Derek moved away from his cock altogether. His cock visibly throbbed from its place standing tall from his groin and it was an angry red color as a new bead of pre-cum rolled from the slit.

“Look at how much you liked that baby, you weren’t sure you could come from it and you almost did. You did good for telling me how close you were, I have one more surprise for you before you can come.” Derek praised as he rubbed his large, warm hands up and down the sides of Stiles’ trembling thighs.

“A surprise Sir?” Stiles licked at his now warming up lips, but his nipples were still erect and cold as was his cock that was aching with the now dulling sensation of his almost orgasm.

“The best one yet,” Derek promised as he reached down and hummed thoughtfully as he rubbed against Stiles’ hole. The other was still loose and slick with lube and come from their quickie earlier in the day. Stiles spread his legs as wide as he could and tipped his hips up, encouraging Derek to push his fingers into him.

“Eyes closed baby, we don’t want to ruin the surprise do we?” Derek ordered as he massaged Stiles’ rim, relaxing it further as he spoke.

“No Sir,” Stiles pouted but closed his eyes anyway. His breath was catching in his throat with each inhale and suddenly his exhale turned into a cry and his eyes flew open on reflex as something ice cold and solid pushed into his body.

“Oh fuck,” Stiles whimpered when he looked down to see a smirking Derek holding the wooden stick that was attached to a blue Popsicle, a Popsicle that was half buried inside of him.

“Do you like your surprise baby?” Derek purred as he pushed the rest of the Popsicle inside of Stiles body, sending shockwaves of cold and pleasure radiating through the human’s body.

“I, uh, ah.” Stiles gasped out, jaw slack as his eyes stayed glued to the way Derek was sliding the Popsicle in and out of him.

“I know it’s not as good as my cock, but I thought you would enjoy it,” Derek spoke causally like he wasn’t fucking the melting dessert into Stiles, his fingers and Stiles hole growing stickier with each thrust.

Stiles flexed around the slender and freezing rod that was rubbing at his insides in a way he had never considered before and clawed at the cuffs around his wrists as a moan fell from his lips.

“You know when someone gives you a surprise it’s customary to thank them.” Derek reminded as he twisted the Popsicle from its place inside of Stiles.

“T-Thank you, Sir,” Stiles stammered out as his eyes rolled skyward when Derek adjusted the angle of the melting Popsicle so it hit against his prostate, sending a chill through his body. Stiles let out a noise that a cross between a sob and a wail when Derek suddenly wrapped his achingly hot hand around Stiles cock and roughly jerked him off. It only took two pumps of Derek’s hand before Stiles was coming and his body arching up off the bed as his vision blurred around him.

“That’s my good boy,” Derek repeated as he licked some of Stiles release off his hand as he looked down at Stiles who looked totally out of it now and the Popsicle still half inside of his clenching hole.

“However this one surprise does make quite a mess, don’t worry baby I’ll clean you up.” Derek purred when the next thrust had the mostly melted Popsicle slip off the wooden stick. The wolf tossed the stick off to the side and unlatched the cuffs from Stiles and tossed the still dazed man’s legs up over his shoulders before he parted Stiles ass cheeks and dove into Stiles ass with his lips and tongue.

“It’s so much Sir, ohhh!” Stiles cried out, yanking at the cuffs still around his wrists as Derek lapped at his freezing cold hole with his burning tongue, slurping and sucking at the melted remains of the Popsicle. Stiles moaned out weakly and lay there pilant as Derek ate him out before the wolf looked up from his place between Stiles shaking thighs, lips and chin smeared with the sticky remains of the blue Popsicle.

“Do I taste good Sir?” Stiles inquired weakly and gave a soft noise when Derek kissed him soundly, sharing the taste of Stiles and the Popsicle between them.

“The best baby,” Derek promised between sticky kisses.

“Color?” Derek asked as he unlatched the cuffs around Stiles' wrists and bundled Stiles up against his side, deciding to clean Stiles more thoroughly in the shower after a cuddle.

“Green Sir, add that to ‘again, but not for at least a month’ list.” Stiles decided as he nuzzled Derek’s chest as he tossed his arm and leg over Derek’s bulk in order to hug him properly.

“Whatever you want Stiles,” Derek promised as he tipped Stiles face up for another kiss.

Chapter Text

“You wanted to see me, Coach Hale?” Stiles shifted nervously in the coach’s office, still wearing his Lacrosse uniform.

“Come in Stilinski,” Derek leaned back in his chair, crossing his arms over his chest pressing the whistle into his skin below the tight shirt he was wearing.

“Is this about how I’m just sitting on the bench during games?” Stiles asked as he sat down in the school chair on the other side of the desk.

“Something like that, I’m afraid I may have to cut you from the team unless you can prove to me that you have some sort of skill that I can use,” Derek explained solemnly and Stiles ducked his head to hide the flush on his face.

“I’m not that great at lacrosse I know, but I’m sure I can think of something I can do for you, Coach Hale.” Stiles peered up at Derek through his eyelashes unable to stop his gaze from taking in the way the man's pecs were straining against the fabric of the shirt.

“I have an idea, come here Stilinski.” Derek pushed his chair back from the desk’s edge as Stiles stood up and moved into the place and squeaked when Derek placed strong hands on the younger man's thin hips.

“This is your idea Coach?” Stiles' voice dropped lower and his eyes were beginning to darken and his soccer shorts didn’t seem as baggy as usual.

“Do you have a problem with that Stilinski? I've seen the way you look at me, making sure to flaunt this perfectly round ass in my face every chance you get.” Derek purred as he shifted his hands around and down to grope Stiles mentioned ass, causing Stiles to moan in surprise pleasure.

“You’re right Coach, I think I’ll be able to show you some of my good qualities that will make you see that I can be useful to you.” Stiles tone took on a pleading tone and Derek hummed thoughtfully as he kneaded and groped stiles ass cheeks.

“Well then, you better give me all you got if you wanted to stay on the team,” Derek smirked as he gave Stiles ass playful smack that made Stiles moan lightly. Stiles took a deep, steadily inhale before he leaned down and kissed Derek square on the mouth. Derek hummed his approval at the kiss and the way stiles hand was rubbing at the front of his jeans right on his I that was swelling up under the new attention.

“Good start, let's see what else you've got Stilinski.” Derek licked his lips when their kiss broke and he took in the cute blush that was on his cheeks.

“I've got a lot more Coach.” Stiles urged as he dropped to his knees. His hands cupped Derek's thighs as the older man parted them automatically for the younger man. Stiles looked up as the Coach unzipped his pants and pulled his 8-inch cock out of its confines.

“Get to it Stilinski” Derek ordered with a lazy smirk on his face. Stiles swallowed to wet his mouth and lips. Stiles leaned down and sucked the head of Derek’s cock into his mouth. Stiles dug his fingers into the denim of Derek’s jeans too. Keep himself balanced as he slowly relaxed his jaw and throat as he took more and more of Derek’s cock into his mouth into he gagged and his eyes watered.

Stiles backed off, licking at the head again before pushing his head back down, taking Derek back into his mouth as far as he could take him. Derek dug his fingers into stiles hair to hold his head in place. Stiles choked as Derek began to thrust into his mouth, taking control of the blowjob now. Stiles hung onto Derek's thighs for all he was worth as he drooled and gaged while Derek’s used his mouth to his own contentment.

Stiles gasped for air, eyes watering as he looked up at Derek when the coach pulls his head back, cock popping free of Stiles' mouth fully.

“Not bad Stilinski, I knew your mouth would be good for something. Now bend over my desk, I’m going to enjoy finally taking this ass of yours.” Derek ordered, voice husky and full of lust.

“Yes Coach,” Stiles sounded out of it but very aroused from the obvious erection he was now sorting in his shorts. Derek released his hold on Stiles' hair, allowing the younger man to shakily rise to his feet. Stiles easily bent himself over the edge of the desk too, planting his feet wide and propping his ass up.

Derek pulled Stiles shorts down to his knees, Stiles underwear and jock followed next and Stiles let out a whimper when Derek cupped the bare perky globes and parted them wide. Stiles moaned as cool at of the office brushed over his now exposed hole and the heat of Derek's gaze on his fully exposed rear end.

“I can't wait to see this hole of yours stretched wide around my cock. Have you let anyone back here before?” Derek licked his lips as he pulled out some lube from his desk drawer.

“Not in the last few weeks but I fingered myself in the shower this morning,” Stiles admitted and Derek smacked his ass again.

“From now on the only one you will spreading your legs for is me. Understood?” Derek felt possessiveness flare up in him at the mere thought of someone else bending Stiles over.

“Yes coach,” Stiles panted as he pressed his cheek against the cool metal of the desk as he shivered when Derek shoved a slick finger into him, wiggling and curling it.

Stiles moaned helplessly to the sensations that Derek's finger was sparking inside of him. Derek slipped another finger into the younger man's hole and spread them wide, watching as Stiles pucker relaxed an open wide under the pressure Derek's fingers were applying.

“I think that you're ready for something a bit bigger don't you Stilinski?” Derek withdrew his fingers as he rose from his desk chair as he poured a generous amount of lube over his hard length. He pumped the flesh a few times to make sure every inch was coated in the lube. Derek groped Stiles ass cheeks again, loving the way they fit his hands perfectly before he yanked them apart and rested the head of his cock against the lacrosse players twitching hole.

Stiles let out a wanton moan as he gripped the edge of the desk for balance as Derek snapped his hips forward, sheathing every inch of his large cock into Stiles. Derek groaned lowly at the tight heat that was clinging to his length now and making it impossible to do anything but shallow thrusts as Stiles adjusted,

Derek hooked his thumbs into the edges of Stiles rim and pulled. He smirked as stiles rim relaxed and stretched wider, allowing Derek room to properly move.

“You better work this ass of yours Stilinski if you want to stay on the team,” Derek ordered as he removed his thumbs and smacked Stiles upturned ass, grinning at the way the soft skin was now becoming a nice shade of pink in the shape of his hand

“Mm, yes coach.” Stiles panted before he pushed himself up off the surface of the desk, gripping the edge of the table harder he began to rock his hips. His cock brushing against the underside of the metal table when he moved forward and Derek's balls slapping against his ass when he pushed backward, taking the older man back into himself.

“Yeah, just like that, fuck yourself on my cock.” Derek crooned as he smacked Stiles ass, watching as the younger man's ass bounced and flexed as stiles fucked himself on Derek's cock. Stiles’ was releasing all sorts of sinful noises as he worked himself over on Derek's cock eagerly.

“Coach, please, please I’m so close. Let me come just from your cock inside of me!” Stiles looked over his shoulder and Derek moaned at the fucked out expression on Stiles' face and paired with those pretty words who was Derek to say no?

“Go ahead Stilinski, I want to see you come on my cock like a whore.” Derek agreed and Stiles let out a weak keen as his eyes rolled up into his head as he shoved himself back onto Derek's cock one final time before he let out a cry as he orgasmed and collapsed onto the desktop.

Derek swore and started to roughly fuck himself into Stiles clenching and tightening ass before he cried out as well as he came inside of Stiles. Derek took a few shaky breaths before he pulled out and sat back down on his chair, tucking his spent cock back into his jeans and took in the sight of Stiles still bent over the desk.

His legs were trembling and he was still up on his tiptoes, ass pink and his hole gaping and oozing Derek's release. His own cock was limp between his own sticky thighs and the hem of his 24 jerseys was ruined by cum and he was half out of it from where his cheek was pressed to the desktop.

“I think I can keep you on the team a bit longer Stilinski but you have extra training with me after practices now.” Derek agreed causally,

“Mmm, okay Coach.” Stiles sounded just as dazed as he looked and Derek rose to his feet as the scene ended and he quickly gathered his love into his arm.

“How does a bath sound baby?” Derek asked as he planted kisses over stiles face as he left the office and moved towards the master bathroom where a bath was waiting for the two.

“Soo good, thanks for indulging this role play of mine and feel free to tell me any ideas of yours.” Stiles happily accepted the kisses and smiled when Derek's ears turned pink.

“Maybe next month, professor Stilinski,” Derek promised low and sultry making Stiles cock give a valiant twitch of interest,

“Mmm yes we are doing that next month.” Stiles tugged at Derek's hair lightly to make the other lean down for more kisses.

Chapter Text

“So that went well,” Stiles rolled his eyes after Isaac finally left the loft and he turned his attention to his boyfriend.

“Why did I think turning teenagers was a good idea again?” Derek moaned as Stiles wrapped his arms around him from behind and all the tension left his body.

“You handled them wonderfully Alpha,” Stiles crooned against Derek’s neck, his hot breath brushing over Derek’s skin making him shiver.

“If you say so,” Derek murmured and he felt Stiles frown against his neck.

“You have no idea, do you? You were keeping them safe and even though they verbally fought back we all know they will follow your orders. You were their Alpha and you did wonderfully today, but it looks like you could use a bit of a break now.” Stiles rubbed his thumb across the top of Derek’s jeans as he spoke and Derek felt a jolt of desire shoot through his body.

“A break would be good,” Derek hummed and Stiles kissed his neck softly as his fingers began to undo his belt buckle.

“I wonder if they had any idea what you were hiding beneath these sinfully tight jeans of yours, what their Alpha was keeping from them while he was ordering them about.” Stiles hummed as he let Derek’s jeans fall down to his ankles, quickly followed by his tight boxer briefs as Derek pulled his shirt up over his head, leaving him fully naked with his still clothed boyfriend behind him.

“It was so hot, watching you being their Alpha while I knew who you submit to,” Stiles commented as he pressed his fingers against the base of the black butt plug that was nestled between Derek’s ass cheeks, knowing full well that it was keeping Stiles cum in place from their morning shower together.

“You don’t have to keep up the act with me Derek, you know you aren’t the Alpha here.” Stiles hummed as he shuffled Derek over to the couch and smiled when Derek willingly bent himself over the arm of it just with the gentle nudge to the small of his back from Stiles' hand.

“I know, thank you, Sir.” Derek let out a shuddering breath as the cool leather of the couch pressed against his bare skin and his cock twitched eagerly.

“I can see how excited your getting sweetheart, but we can’t have you staining the couch can we?” Stiles tsk’ed as he took Derek’s large cock in his hand, making a small noise when his fingers barely closed around the girth. Stiles squeezed the sensitive organ before removing his hand and stepping back.

“Be good for me and stay put.” Stiles patted Derek’s ass playfully before jogging to their bedroom, leaving Derek naked and bent over the arm of the couch.

Derek’s legs trembled a bit before he settled himself and closed his eyes, he trusted Stiles with everything he was and this was no different. He could hear Stiles moving around in their bedroom and his scent was growing musky with his own arousal and his heartbeat steady. It was soothing to Derek and he lost himself in it a bit before he snapped back to himself when Stiles’ hand was back on his cock.

“There we go,” Stiles crooned as he locked the metal cock cage into place around Derek’s thick cock, making sure the key was secure around his neck before he maneuvered Derek’s lower half until the black jockstrap was correctly in place. The cup covering Derek’s caged cock and the straps artfully cupping and pushing Derek’s ass cheeks upwards, showcasing the black plug nicely.

“You know the saying, out of sight, out of mind,” Stiles commented as he began to work at his own jeans, he was aching and leaking in his boxers. He had to resist the urge to bend Derek over for the whole meeting so it was time to act on that urge.

“Stiles,” Derek blushed as he buried his face against the couch cushion and breathed heavily out through his nose. He loved when Stiles did this, it really drove home to his inner wolf who was in control in their relationship and it drove him insane with a need to please Stiles.

“I’m going to slide right into you sweetheart, you’re going to be so loose and wet from this morning. You’re going to feel so good around me, I can’t wait to fill you again and if you’re good I’ll plug you back up.” Stiles promised as he wiggled the butt plug slowly out of Derek and moaned under his breath at the sight of his cum slowly spilling out of Derek’s loosely clenching hole when the plug slipped free completely. Derek let out a broken noise as he dug his fingers into the leather of the couch; his legs parting wider as he felt Stiles cum run down his thighs.

“God, look at you.” Stiles breathed out in praise as he grasped the base of his erection and with one hand going to Derek’s hip, he guided his cock into Derek’s winking hole. Stiles sank in with a lewd squelching noise that was overpowered by Stiles and Derek both groaning at the action.

“Fuck,” Derek swore against the couch cushions and tilted his hips up, allowing Stiles’ cock to slide deeper into him right against his prostate sending stars over his vision.

“So damn good for me Alpha, taking my cock so damn well.” Stiles panted as he stared at where the two of them were connected. Stiles ran his hands over the firm globes of Derek’s ass and squeezed them in silent awe after all Derek’s ass was a work of art. Derek reached back blindly and grasped Stiles’ jean-clad thigh and tugged at it in silent need.

“I’ve got you, Derek, I’ll take good care of you.” Stiles snapped himself out of his trance and gripped both of Derek’s hips before he began to thrust in earnest, pulling almost all the way out before slamming himself back in roughly just the way Derek liked it.

Derek let out something close to a howl that was muffled in the couch as Stiles cock hit against his prostate without pause and his cock ached and strained against the cage it was trapped in and dampened the fabric of the jockstrap. The feeling of his orgasm being pushed back by the two was heady and Derek had found out early on with Stiles that he loved the feeling immensely. Derek could hear every pant, every grunt and every groan Stiles gave as the human fucked into him from behind and Derek knew that Stiles nearing his climax.

“Stiles, I want it, please come in me again.” Derek pleaded, he knew that it was a big kink of Stiles and he secretly did enjoy the feeling of being so full of his mate’s cum, even though he was an Alpha.

“Derek, fuck.” Stiles panted as he dipped his head down as he drove himself deeper and harder into Derek before letting out a cry as he came, adding fresh cum to the load he had already left inside of Derek that morning. Stiles gasped for air as he doubled over Derek’s back and panted against Derek’s bare back, absently kissing the tattoo between his shoulder blades.

The two stayed like that for a moment or two as Stiles got his senses back and Derek enjoyed the ache of his own denied orgasm and the way Stiles cum was filling him. Stiles kissed his tattoo once more before straightening up and slowly the human pulled his now spent cock out of Derek now gaping and cum drenched hole.

“Gonna put the plug back in okay sweetheart?” Stiles murmured as he picked up the discarded plug and Derek nodded against the couch and he let out a contented purring noise when the plug was pushed back into him, locking Stiles cum inside of him and keeping his hole stretched open.

“You did so well Alpha, you were perfect for me.” Stiles praised and Derek smiled dopily as he was gently eased upright and face peppered in loving kisses.

“How about we go cuddle a bit now yeah? I know you love a good cuddle,” Stiles smiled as Derek tugged him into his arms, inhaling his scent happily. His caged cock bumping against Stiles' stomach thanks to their height difference and he whimpered when Stiles stroked the front of the jockstrap.

“If you’re really good for me tonight Alpha, I’ll consider letting you come.” Stiles offered.

“Yes Stiles,” Derek agreed breathlessly and let Stiles tug him towards their bedroom for the promised cuddles.

Chapter Text

Stiles peered around his locker in the boy’s locker room, gym class had just finished and Stiles was in his personal heaven or hell, depending on how he was feeling that day. Right now he was right on the edge as his eyes caught sight of Derek Hale. Derek Hale was a year older than him and Captain of the Basketball team.

Derek was wearing low-slung basketball shorts and was getting ready for a shower, but Stiles' eyes were drawn to the sizeable bulge Derek was sporting in his shorts. Stiles absently licked his lips as his mouth watered, he had so many daydreams about seeing Derek’s cock in person and letting it fuck his mouth.

Stiles had been so distracted by Derek’s crotch and his own daydream that he didn’t notice the locker room had emptied out. It was just him and Derek now and Stiles flushed when he caught Derek catching him staring.

“See something you like Stiles?” Derek asked coyly, fingers hooking the waistband of his shorts and Stiles swallowed audibly.

“Uhh?” Stiles blinked owlishly.

“You’re welcome to join me in the shower,” Derek called over his shoulder as he dropped the shorts onto the floor and he stepped into the warm spray of the communal shower. Stiles whimpered softly as his eyes took in the firm ass of Derek and the way he could see just a hint of the teen’s cock between his corded thighs when he walked.

“Fuck it,” Stiles muttered, when would he get another chance? Stiles stripped off his clothes and shuffled fully naked into the shower, hovering next to Derek.

“Nice of you to join me, do you really think I’ve haven’t noticed you?” Derek asked, side-eyeing Stiles as he soaped up his chest, smoothing his hand downwards, smirking as Stiles' eyes followed his hand. Stiles whimpered as Derek began to stroke himself with his soapy hand and he had to lock his knees to stop himself from sinking to his knees at that very moment.

“You’re always watching and licking those damn lips of yours. It took me a minute to figure out why you want this don’t you?” Derek let out a grunt as he thrust his hips forward, his cock sliding through his wet hand and Stiles’ cock jerked in response.

“Don’t you?” Derek said harshly and Stiles jolted.

“Yes, fuck, yes I do.” Stiles panted out as he curled his fingers into a fist to stop himself from mirroring Derek and touching himself as well.

“Then why aren’t you on your knees yet?” Derek raised an eyebrow and chuckled when Stiles instantly dropped to his knees and parted his lip wide and eager.

“Such an eager little slut aren’t you?” Derek said sounding amused as he turned and with one hand curled around the base of his cock he slapped Stiles cheek with his cock. Stiles mewled and took a shuddering breath as he locked eyes with Derek as the older teen dragged his cock and balls over his face like he was marking Stiles as his.

“Gonna put those blow job lips to proper use,” Derek grunted and Stiles moaned and a bead of pre-cum dripped from his cock that was washed away by the light spray of water.

“Stick your tongue out you little slut,” Derek ordered, loving how Stiles obeyed instantly and only seemed to get further turned on by the filth Derek was spewing.

“Oh yeah, that’s good.” Derek moaned as he slapped the head of his cock against Stiles outstretched tongue a few times before pushing his cock into Stiles' mouth.

“Fucking hell,” Derek tossed his head back under the fall of water, moaning in pleasure at the sensation of Stiles’ mouth warm and hot around his cock.

“You’re really good Stiles, fuck.” Derek praised as he ran his fingers through Stiles' hair a few times as Stiles sucked and licked at Derek’s cock almost expertly. Derek looked down at Stiles who was still looking up at him with dark eyes, those sinful lips spread wide around Derek’s cock. His face was damp from the spray of water and drool was already pooling at the corners of his mouth.

“Gonna fuck this mouth of yours, make you my cock slut.” Derek decided as he tightened his grip on Stiles' hair and shuddered when Stiles moaned around his cock sending bolts of pleasure through his body.

Stiles relaxed his jaw and kept his eyes locked on Derek as the older teen began to roughly thrust into his mouth. Derek was using his hold on Stiles' hair to pull the teen’s head forward to meet his thrusts. Derek’s moaned and grunts filled the empty locker room as his balls began to slap against Stiles' chin.

Stiles took every thrust happily, mentally thanking himself for training his gag reflex away and finally, he reached between his thighs and wrapped his fingers around his aching cock. Stiles moaned and sucked the best he could as he jerked himself as he let the Basketball Captain roughly fuck his mouth. This was every fantasy Stiles had ever had coming true and he loved the way Derek’s cock felt in his mouth, leaking pre-cum over his tongue and throbbing.

Stiles let out a disappointed whine on reflex when Derek pulled his head back forcing the older teen’s cock out from his mouth. Derek was panting and cheek flushed as he looked down at Stiles who looked debauched and lips swelling from use.

“Gonna come on that pretty face of yours slut, gonna mark you as my cock slut,” Derek promised in a sultry voice that made Stiles shiver and pumps himself faster.

“Please,” Stiles gasped out and Derek just smiled as he stroked himself fast and rough. Derek let out a loud cry, body arching and cock pulsing in his hand. Stiles closed his eyes and kept his mouth open as warm streams of cum landed on his face and some even in his open mouth.

“That’s a good look on you, come on wash up Stiles. We’ll get some food and maybe if you’re good I’ll let you suck me off again before I drop you off.” Derek decided as he helped Stiles up onto his feet, rubbing his thumb through some of his own cum on Stiles' face and shoved it into the teen’s mouth. Stiles looked at Derek through his lashes seductively as he suckled Derek’s thumb clean of cum.

“Sounds good,” Stiles agreed and smiled when Derek just beamed at him and he knew this was going to be a fun year of high school and maybe more.

Chapter Text

Loud bass rocked the foundations of the club as lights flashed and bodies writhed together on the dance floor. It was masquerade night at the Jungle and everyone seemed to be there looking for booze and sex.

Not that Stiles in a different mindset, he had just recently come back to Beacon Hills and needed one last night before he faced his childhood town again so he came to the Jungle with a red fox mask firmly in place over his face only exposing his lips and chin and grabbed himself a drink before mingling with the grinding bodies on the dance floor.

Bodies bumped and ground on Stiles as he twisted and rolled his body sinfully, he had picked up a few things during his time in college and if his dancing got himself a hookup for the night then he was all for it.

Strong, large hands cupped his hips and he was pulled back against a just as large man who was wearing tighter jeans that Stiles was and a black leather jacket. Stiles didn’t bother turning around to look at the man’s face that was no doubt hidden by a mask, he simply tossed his arms up and back over the man’s shoulder and ground his ass back on the man’s crotch.

Stiles had to swallow a moan when he felt a long, hard line of the other man’s erection pressing against his ass and his own cock jerking in response to the size. Stiles rubbed his ass along the length as he rolled his torso seductively, head tipping to the side as the man’s beard brushed over his skin and soft lips pressed against the arch of his neck.

Stiles hooked his fingers into the man’s dark hair as he twisted his neck around and got a face full of a black wolf mask that seemed to be a common theme that night but Stiles only had eyes for the larger man who was still grinding on him. Stiles slowly licked his lips watching the man’s eyes follow the motion.

Stiles made his choice right then and there, this man was 100% his type and Stiles wasn’t against a quickie in the bathroom so that was what was about to happen. Stiles laced their fingers together and jerked his head towards the bathroom. The man looked at the bathroom before back at Stiles, raking his eyes over him before nodding jerkily. Stiles smirked and began to pull the older man towards the bathroom, the two had to wade through the mess of people. When they finally stumbled into the bathroom, moans, and sounds of flesh on flesh was already filling the air.

Stiles smiled cockily and dragged the man down in for a dirty kiss as the two stumbled into an unoccupied stall, the man kicking it closed and locking it behind them. Stiles didn’t waste any time, he ran his hands down the tight shirt under the jacket, feeling how toned the man was but he went directly to the tight jeans.

The man growled into Stiles' mouth as Stiles quickly undid his belt and then his fly. Stiles groped the hard length teasingly before breaking their kiss and giving a smirk at the panting man. Stiles turned towards the toilet and shut the lid before he knelt onto the lid with one knee as he undid his own sinfully tight jeans and pulled them down to his ankles, showing off that he had gone commando. Stiles peered over his shoulder as he reached back and tugged his ass cheeks apart in an obvious invitation, his hole already wet with lube as Stiles was always prepared for these things.

The man moaned lowly at the sight as he pulled his rather massive cock from his jeans, pulling a condom out of his jean pocket. Stiles watched breathlessly as the man rolled it over his thick cock, pumping himself a few times before he crowded up against Stiles.

Stiles gripped the back of the toilet as the man lifted his right leg up and rubbed the head of his cock against his hole. Stiles inhaled once before the man was pushing into him. Stiles moaned loudly unable to stop himself and clung to the back of the toilet as he was spread wider and wider as the man pushed his massive length into him. Stiles was sweating, panting and trembling by the time he felt large, heavy balls slap against his ass. His own cock was dripping like a faucet by this point and Stiles was so aroused he couldn’t think straight.

The man ducked his head down to stare at where he was buried inside of Stiles tight ass and moaned as he couldn’t resist the urge to start moving. Stiles groaned as the man began to thrust into him, first, it was slow and shallow but soon the pace changed and Stiles was howling with pleasure.

Stiles was being impaled over and over again on the man’s thick cock that hit against his prostate with each hard and fast thrust he gave. The man was grunting and groaning behind him as his balls smacked against Stiles ass each time he was fully sheathed inside of him.

“Fuck!” Stiles shouted out loudly when the man’s large hand wrapped tight around his cock and jerked him roughly. That was all Stiles needed to finish and see stars as the man kept pounding into him, chasing his own orgasm.

The man swore under his breath so fast and low that in his dazed state Stiles couldn’t hear in his dazed state, but Stiles felt the large cock throb inside of him before the man pulled out completely. Stiles panted desperate for breath, his ass was clenching and he felt so empty yet totally sated.

“Fuck,” The man muttered as Stiles reached up for him, dragging him in for another kiss. The two traded smaller kisses as they righted themselves and before Stiles knew it, the two were back on the floor and one last filthy kiss later and the masked man was gone, blending in with the crowd.

Stiles licked his lips before smiling, pleased with his hookup and merged back with the crowd, intent on just drinking and dancing for the rest of the night.

Chapter Text

Stiles banged his head black against the headrest of his car when he caught the sight of police sirens flashing in his rearview mirror and the following blare of sirens. He pulled his old Jeep into park on the side of the side road that was never used. Of course, he would get pulled over here, Stiles sighed as he dug around for his registration before looking at his window when a gloved hand knocked at the window. Stiles felt his breath catch in his throat as he recognized those large hands and the slight bulge in his uniform pants.

“You have to be fucking with me,” Stiles muttered as his suspicions were confirmed when the man leaned down just low enough to show a familiar bearded chin and full lips.

Stiles sighed and slammed the glove box shut and opened his door causing the officer to step back. Stiles slipped out of his Jeep and finally made eye contact with the man and tried not to choke on his own spit.

“Derek!?” Stiles squeaked as he leaned back against the side of his Jeep.

“Good to see you, Stiles.” Derek's lips twitched as his eyes raked over stiles body.

“Fuck, I had no idea you were back in town. Let alone a Deputy of all things.” Stiles raked his fingers through his hair.

“I came back a few years ago. I must have just missed you leaving. Your father was good to me, helped me get a job and I rose up the ranks. Parish and I are both deputy now.” Derek explained and Stiles exhaled a short laugh.

“Good for you sourwolf, the uniform looks good on you. So does that smile.” Stiles jerked his chin at the smile that was on Derek's lips. Lips he had tasted that night in the club and fuck he needed answers.

“We should talk big guy and I know that cruiser has a dash camera so maybe we should move away from it?” Stiles suggested and Derek gave a jerky nod. The two moved around the cruiser until the two were by the trunk.

“I should have known, a wolf mask isn’t subtle,” Stiles commented after a deep inhale.

“Like you should talk...” Derek snorted before falling silent and shoving his hands into his pockets.

“Did you know it was me the night in the Jungle or?” Stiles got to the point and Derek shifted looking guilty.

“Not until you shouted at the end. It had been a while and clubs always mess with my sense of smell, plus you’ve grown up a lot since I last saw you... I’m not sorry we had sex but I’m sorry it wasn’t after a date and in a bed.” Derek blurted out and Stiles leaned back against the trunk of the car.

“I do wish I knew it was you but I don’t regret how or where we had sex. It was the best I’ve ever had and I’m still feeling your cock inside of me. It’s amazing.” Stiles knew he couldn’t lie to Derek and was rewarded with an actual blush from the werewolf and the bulge in his pants seemed to grow.

“A date and a proper bed does sound good though if you're not opposed to that.” Stiles stepped forward, hooking his fingers into the belt loops of the uniform pants, pulling Derek close to himself. Derek’s hands fitted themselves to stiles hips almost on reflex.

“Definitely not opposed to it,” Derek murmured out as he ducked his forehead to rest against Stiles.

“Kiss me sourwolf, sorry deputy Hale.” Stiles purred as he ground their hips together. Derek’s eyes flashed and he greedily captured Stiles lips in a kiss, just as dirty as the night in Jungle but somehow more passionately than before.

“A bed sounds good but seeing you in this uniform is doing things to me, Deputy. Would you be against taking me right here and now?” Stiles suggested when their kiss broke and Derek began to kiss down Stiles bared throat.

“Kinky,” Derek hummed as he pulled back as Stiles chuckled.

“You have no idea sourwolf,” Stiles smirked and moaned when Derek squeezed his ass

“Right back at you,” Derek commented making Stiles raise an eyebrow before whining when Derek twisted him around and bent him over the trunk of the police cruiser.

“You’re going to feel so good around me again Stiles,” Derek whispered in Stiles' ear as he plastered his body to Stiles.

“Fuck me, Deputy Hale.” Stiles purred as he rubbed his ass back against the familiar hardness in Derek's pants.

“You can’t wait to be fucked by one of your fathers Deputy’s huh? Such a little slut.” Derek hummed and Stiles flushed as his cock jerked in his jeans.

“Do you like that Stiles, so you like being called that?” Derek smelt the sharp increase of Stiles arousal at his words.

“Yes, fucking hell just get inside of me already.” Stiles snapped, feeling foiled and his body burning with need.

“We’ll play around with that later,” Derek promised with a kiss to Stiles' neck as his deft fingers undid Stiles jeans and yanked down them along with his boxers.

“I didn’t get to appreciate it before but god your ass is a work of art,” Derek commented as he cupped the soft globes of flesh making Stiles keen and press his cheek to the cool metal of the police cruiser.

“God I did a number on you, you’re still gaping from taking my cock last night,” Derek whined as his inner wolf made a pleased noise at the sight of Stiles hole still gaping from the night before.

“Told you,” Stiles moaned out as Derek licked two of his fingers and shoved them into Stiles. “Fuck.”

“I can’t wait to watch your greedy hole take my cock again.” Derek murmured making Stiles slightly clench around his fingers. Derek wiggled his fingers before pulling them out and leaning forward to swipe his tongue over Stiles hole.

“Oh fuck!” Stiles squealed and clutched at the edge of the trunk as he parted his legs wider as Derek licked and lapped at his hole. Stiles found himself whining when Derek pulled away completely and stiles peered over his shoulder to see Derek working at his pants.

“No condom, werewolf’s don’t get diseases right? I want to feel your cum dripping out of me when I meet my dad this afternoon.” Stiles purred out and Derek made a wounded noise.

“You’re a filthy little slut,” Derek commented as he pumped his hard cock a few times before stepping closer to Stiles.

“Ohh!” Stiles cries out in pleasure as Derek pushed himself into him from behind. “So big, fuck!”

Derek watched as Stiles rim clung to his cock and his body eagerly suck down his length fully. It was an easy glide into Stiles that had both of them moaning.

“Just as tight as I remembered,” Derek grunted as he circled his arm around Stiles' waist as he began to thrust in and out of Stiles.

“God you feel like your splitting me open, I love it oh fuck Derek!” Stiles moaned as he rocked back against Derek, meeting his thrusts each time. Derek grunted and lifted Stiles right leg up to prop it up on the police cruiser to get a better angle. Stiles moaned loudly at the new angle and whined when Derek began to kiss and bite at his neck, marking him.

“Fuck I’m close,” Derek grunted into Stiles' neck.

“Come on Deputy Hale, I want to feel you coming inside of me.” Stiles encouraged breathlessly.

“Fucking slut, you’re gonna be the death of me.” Derek moaned weakly but buried himself deep into Stiles clenching hole and with a loud groan, he came, spilling his cum into Stiles accepting body.

“Fuck!” Stiles shouted when Derek gripped his cock and with a sharp tug made him see stars. Stiles panted as he lay limp still bent over the trunk of the police cruiser and he whimpered when he felt Derek pull out of him, which was followed by a trail of warm cum sliding down his thighs from his now clenching and empty feeling ass.

“So movie at my place tonight?” Stiles asked as he eyes Derek who was doing up his pants, looking just as out of it as Stiles felt.

“I’ll bring Chinese.” Derek offered and Stiles reached back blindly. Derek laced their fingers together and pressed soft kisses to each of Stiles long fingers.

“Sounds like a date, Deputy Hale.” Stiles smiled and Derek rolled his eyes with a fond smile on his lips as well.

Chapter Text

“Are you sure about this Stiles?” Scott asked, skating his fingers nervously up and down his best friend’s side as the two stood naked before each other under the full moon by the stump of the Nemeton.

“We need to seal this damn stump and it takes both the Alpha of the pack and his Emissary to do this.” Stiles shrugged, unabashed in his nakedness.

“Yeah, I know I was there when Deaton told us. I just mean we’re best friends dude and your scary ass boyfriend is right there, being forced to watch us thanks to the ritual needing a ‘witness’.” Scott’s eyes darted over to the glowing pair of blue eyes that were hidden in the trees that surrounded the small clearing.

“It’s fine Scotty, really it’s fine. Now come here Alpha,” Stiles purred as he grasped Scott’s cock, stroking it firmly as he tugged Scott down in for a proper kiss. Scott moaned at the sudden boldness of Stiles and wrapped his arms around his best friend’s waist, hands cupping his ass almost on reflex. Scott shuddered when he heard Derek growl lightly from the tree line.

“It’s fine Scott, just focus on me yeah?” Stiles soothed as he kept pumping Scott’s cock, working him to full hardness.

“Yeah, I can do that.” Scott panted as he leaned down and kissed a line down Stiles exposed neck, getting a soft sigh from his best friend whose own erection was pressing against his thigh.

“Stiles,” Scott found himself growling when his fingers ran through the wetness of lube when they grazed between the other teen’s ass cheeks.

“Thought I would speed things up,” Stiles breathed out and moaned when Scott pushed two of his fingers into him with ease. Stiles’ hand slipped from Scott’s cock to grab the Alpha’s shoulders as he moaned and rocked back against Scott’s fingers that were pressing deeper and twisting inside of him.

“Come on Alpha,” Stiles panted and he let out a groan when Scott growled lowly at him, his red Alpha eyes gleaming in the darkness and face shifting into his wolf form.

“Be a good Emissary and get onto the stump,” Scott growled out his order and an accompanying growl echoed from the tree as Stiles stepped away from Scott’s naked body and settled on the wooden stump on his hands and knees. Stiles shuddered with a soft exhale as the tips of the Alpha’s claws skimmed over his skin before human fingers gripped his hips tightly. Stiles looked up and locked eyes with Derek’s blue glowing ones just as Scott thrust into him from behind.

“Ohhh!” Stiles jaw dropped open as a cry was punched out of him as Scott impaled him on his cock. The Alpha’s breath was hot against his neck and little growls rang in Stiles' ears as the human gasped for air.

“You’re still so tight, does your boyfriend not fuck you properly?” Scott asked voice low and full of lust and Stiles knew the Alpha side of him had taken over.

Stiles could feel himself losing the battle to the magic that was now sparking up around them as the ritual began in full and the full moon shining down on them from above. Derek snarled from the tree line and Scott snarled back while pulling back just enough so the head of his cock was still resting inside of Stiles before he purposefully snapped his hips forward.

“Alpha!” Stiles cried out unable to stop himself as the roughness of the thrust and the angle against his prostate made him see stars. His own cock was hard and leaking now from between his thighs as he dug his own nails into the wood of the Nemeton. Scott kept up the steady if not a bit brutal pace, snarling and moaning the whole time. Stiles’ was no better himself, he was keening and gasping each time Scott slammed into him.

Stiles knew Derek was still watching and could clearly see Scott’s cock disappearing inside of him with each thrust and Scott’s heavy balls slapping obscenely against his best friend’s and Derek’s boyfriend’s ass. Stiles knew Derek had a thing for watching and Stiles just knew his boyfriend was sure to be rock hard by this point. Stiles arched his back and flexed his ass around Scott’s cock.

“Come on Alpha, come in me, you know you have to.” Stiles moaned as he reached down to jerk himself off, not being able to hold himself back any longer.

“Fuck, Stiles!” Scott let his head fall back, fangs extending as he basically howled out his release once he was fully buried inside of Stiles’ clenching ass. Stiles let out his own cry as his cock spurted cum over his hand and dripped down onto the surface of the Nemeton. Stiles whimpered as he felt Scott’s cum rush into him, giving him an odd warm sensation. Stiles and Scott panted in unison and Stiles mewled unable to stop himself when Scott pulled out and gently flipped him onto his back and stared down at him with those glowing Alpha red eyes.

Stiles lay there, chest heaving and legs sprawled wide as he relaxed his lower muscles and shivered when he felt Scott’s cum run out of his sore ass and pooled on the surface of the Nemeton. Suddenly the whole area was bathed in light and the cracks and crevices in tree stump glowed at the same time Scott and Stiles' eyes did.

As fast as it appeared the light disappeared and Scott was slumping onto Stiles' chest, both appearing unconscious and Derek was by their side in a moment. He could hear their hearts beating steadily, but he made sure to take their pulses just in case. He dropped the bag he had over his shoulder and fished out some clothes and a washcloth, he gingerly wiped both teens down before easing them both in a pair of loose sweatpants.

Derek was rock hard in his jeans from the sight of the two rutting like animals in heat but he had to take care of their pack’s Alpha and his own mate. He knew Stiles was going to be insufferable for the next while after all he was now officially proven right about Derek being into watching and would no doubt take advantage of it, but Derek found himself excited to see what Stiles would think up, until then he would make sure they both suffered no ill effects of this damn ritual.

Chapter Text

Stiles sipped slowly at his martini, his colored wristband shining in the low light of the club. He had chosen one that signaled that he was single but not looking for anything, he had been in need of stress relief so he headed to Club Onyx that was a rather supernatural creature filled BDSM club. People were enjoying themselves all around him, some in pairs, some in groups, some by themselves but nothing seemed to catch Stiles attention.

“You look a bit bored, if you want I have an idea.” A pretty woman with glittering fairy wings sank onto the couch next to Stiles, cheeks flushed and breasts bare.

“An idea?” Stiles asked curiously.

“Totally, since you don’t want to hook up with anyone tonight,” the fairy nodded at his wristband and he absently touched the colored fabric. “Head to the next room, there is a show that is going on there that may catch your interest.”

“Thanks,” Stiles smiled and his eyes fluttered as the fairy pecked his lips before bouncing off to a vampire who smiled with his fangs on display as she tugged the pretty fairy close. Stiles finished his drink, setting it down to be taken away later and rose to his feet. Stiles weaved through the room and into the next room and his breathing hitched.

There was a raised circular platform in the middle; a black leather-breeding bench occupied it with a muscular man with black hair and stubble strapped to it. Stiles moved closer and his eyes were drawn to the sculpted ass that was currently being pounded into by a werewolf male. Stiles noticed a worker of the side of the platform, talking with the growing line of men that seemed to be waiting their turn with the man on the bench.

Stiles slowly made his way around the platform, his pants becoming tight as the werewolf pulled out, showing those on that side of the room the sight of the other’s man’s gaping, puffy, cum sloppy hole. Stiles palmed himself at the sight and kept slowly walking even as a new man took his place and slotted his cock right back into the man’s open hole.

Stiles found himself stopping as the new action caused the man attached to the bench to moan and head lift up, eyes closed, cheeks flushed and mouth open. Stiles gripped the bulge in his jeans and swallowed down a whimper, the man being fucked by all these men was Derek Hale. Fuck this was something out of Stiles dirties fantasies but it was real and happening before his eyes.

Stiles’ knees went weak and he sat heavily into an empty chair, just out of Derek’s line of sight but gave him the best profile sight of Derek’s firm body propped up on the bench and the man fucking into him from behind. Stiles unzipped his jeans and tugged his cock out into the warm air of the room.

Stiles let out a little moan as he began to stroke himself as his eyes stayed glued to the platform before him and bit his lower lip so hard he was worried it may bleed soon. Stiles’ hand was tight on his cock as he roughly stroked himself unable to stop himself from doing so as he imagined what it would be like to slip into Derek’s hole after the man took this many cocks and loads of cum. Stiles suddenly found himself coming harder than he had in a very long time as the man fucking Derek finished and stepped back, giving everyone the sight of Derek’s fucked loose hole again, more cum dripping down Derek’s thighs and over his own cock and balls that were restrained by a rubber cock ring.

Stiles sank back in the chair, breathing heavily as he kept pumping his softening cock as he watched as the next man stepped up and easily thrust into Derek. Derek’s head turned to the side and Stiles’ breath caught in his chest when his and Derek’s eyes locked. Derek’s lips curled up into a smile before his face went slack with pleasure and head resting down against the headrest of the bench. Stiles let out a breath and made a mental note to talk with Derek and maybe next time he came to Club Onyx he wouldn’t be alone.

Chapter Text

“Now you are okay with this? I mean you’re going to watch as I suck off any number of anonymous guys?” Derek raised an eyebrow as he looked down at his Dom who was seated on the toilet inside of the special bathroom stall in Club Onyx. It was special in the way it had a cushion on the floor and just above that was a hole in the wall, the other wall mirrored it but Derek was planning on just using the one tonight.

“I’m positive Derek, remember we got together because I got off watching you being fucked by a literal never-ending line of other werewolf’s and I think there was a vampire and fairy in there at some point.” Stiles waved his hand near the end before hooking his finger and Derek knelt down, hands flat on Stiles' thighs.

“You are mine and I’m yours, Derek. I’m not going to change my mind okay?” Stiles cupped Derek’s face in his hands, bestowing him a sweet kiss. Derek all but melted into the kiss, loving how Stiles can all but destroy him with a simple kiss and a few words, it was dangerous but Derek loved it.

“Now put on a good show for me baby,” Stiles winked when their kiss broke and he leaned back on the toilet, getting comfortable. Derek felt his cheeks flush but he shuffled over to the hole, adjusting his caged cock in his tight jeans. They showed everything off and many people had noticed as he and Stiles walked through the club that night. The red leather collar and a silver dog tag around his throat also helped but Derek loved it even if Stiles had bought it from a pet store with Derek present. Asking him his opinion with that sly look in his eyes that Derek discovered always brought him pain or pleasure, sometimes both.

“Yes Master,” Derek breathed out before Stiles smacked his hand against the wall in a signal for the others on the other side. Derek inhaled the sharp musky scent as the first cock was pushed through the hole, right at eye level for him.

Derek placed his hands on the wall and lifted his hips, moaning as he greedily swallowed the unknown cock. Stiles gave a quiet moan at the sight and slowly unzipped his own pants, fingers wrapping around his own length while the weight of the remote in his pocket became obvious against his hip. Derek was bobbing his head now; Stiles watched as the unknown man’s cock disappeared in and out of those sinful lips that Stiles used daily. He never would have guessed Derek for being so cock hungry but here they were.

Derek let the man’s cock slid from his mouth and used his right and to jack the man off the rest of the way, moaning happily when spurts of cum jetted from the tip of the penis in his hand, covering his lips and chin with the warmth. Derek released his hold and made a pleased noise when the moment the now spent cock was pulled back a fully harden one was pushed in, balls popping through the hole as well.

Derek looked at Stiles from the corner of his eyes as he stuck his tongue out and let the hard cock glide into his mouth. Derek’s eyes fluttered shut as he sucked, twirling his tongue as he did. He loved the weight and taste of a cock on his tongue and the way his jaw always ached afterward as a reminder when all the cum had been washed away. Derek swallowed around the cock a few times before pulling back and lifting up the man’s length in order to lick down the underside and he began to mouth at the stranger’s balls.

Stiles was rubbing his thumb over the tip of his cock as he watched Derek used his mouth expertly, lips slick with salvia and cum already as he brought the owner of the cock he was playing orgasm, this time his release painted Derek’s right cheek before it was gone and a new one was pushed in. Derek dove back in with gusto and his face blissful as he worked the new cock over.

Derek had just had a third load of cum painted his left cheek when he let out a cry as the plug Stiles had put into him suddenly buzzed to life intensely. Derek leaned his forehead against the wall, curling his hand around the newest cock as he tried to regain his breath. Derek looked over at Stiles who was looking smug as he waved a small remote at Derek while he fondled himself. Derek shuddered as the plug nudged against his prostate making him leak a bit in his cage before he took the man’s cock between his lips again.

Derek felt his attention waver and sucked down the hard length a bit more sloppily than he normally would have but with a hard suck here and a prodding tongue there, Derek's face was coated with another load of cum. Derek found himself shuffling onto his hands and knees to alleviate the pressure of the vibrating toy, but all it did was making him hotter and ache as it settled firmly against his prostate.

Derek took the lull period to push his face against the wall, lips spread around the hole and he stuck his tongue out there the empty area in a signal that he was ready. Stiles let out his own moan as he watched Derek do this, relax his jaw completely and keenly debauched as the next cock was thrust into his waiting mouth. Derek was ready and willing to let these strangers fuck his mouth the way they wanted now and that was how Stiles knew the toy in his ass was affecting him.

Stiles let out his own keen as he came, watching as Derek’s Adam’s apple bobbed and cum trailed from the corners of his mouth as he swallowed the man’s seed. Stiles wiped his hand clean on some toilet paper before he tucked himself away and shifted off of the toilet seat.

Stiles knelt behind Derek, tangling his fingers in his hair in a silent show of telling Derek he was there. Derek just moaned around the new cock in his mouth and choked around it a moment later when Stiles pulled his jeans down and began to wiggle the base of the buzzing plug.

Derek let out a muffled noise that could have been a sob when Stiles began to stroke his caged cock with light fingers and roughly started to fuck him with the vibrating plug. Derek automatically swallowed the rush of cum before a fresh cock was shoved into his mouth while Derek pushed back against the plug Stiles was fucking into him. His mouth was full of stranger’s cocks and their cum while his Dom fucked his ass with that damn plug, Derek was in heaven and the throbbing of his cock did nothing to stop that feeling.

“Jerk the next few off, I want to see you covered in their cum while I fuck your tight little ass open on this toy.” Stiles suddenly ordered and it shot through Derek like fire. Derek pulled his cum soaked mouth and chin away from the hole and used both hands on the next few cocks that came through the hole, making sure to give sinful moans and when they came he made sure it hit his face, neck or t-shirt so it was clear what he had been doing.

Stiles checked his watch, as the last cock was pulled back from the hole, limp and satisfied. Stiles pushed the plug back into place and Derek gave a confused whimpering noise when Stiles pulled his jeans back up into place.

“You did good baby, you took so many cocks tonight and when we walk out everyone will know it. If you’re good for me on our way home I’ll consider replacing that plug with my cock, but only if you’re good.” Stiles ordered as he rose to his feet and Derek peered up at him, face and shirt drenched in unknown cum feeling wound up as his cock pulsed in its cage and his hole clenched around the still vibrating plug desperately.

“Yes Master, thank you,” Derek said respectfully as the dog tag on his collar jingled reminding him that he was Stiles’.

Chapter Text

Stiles’ footfalls echoed through the forest, twigs crunching under his bare feet. Stiles twisted his torso around, eyes wild as he heard the cries of Alphas behind him. He hated being an Omega during this time of year, hated that he was forced to take part in this mating run. Stiles didn’t want to be the Omega to any of these Alpha assholes so he refused to be caught.

Stiles was too focused on evading the Alpha’s chasing him that he didn’t notice the way the ground dipped into a downward slope. Stiles yelped as his feet tangled under him and he pitched down the slope, rolling and gasping until he came to a standstill at the bottom in a heap.

Stiles lay there dazed as he felt blood roll down the side of his face, his vision dark as he tried to steady himself. Stiles froze, barely breathing as he heard the Alpha’s approach the top of the slope. Stiles risked looking up and his breath was taken away when a new unfamiliar snarl echoed through the forest and a naked man in his full beta shift landed in front of the Alphas. The man growled, flexing his claws and Stiles watched in amazement as the other Alpha’s backed off. They snapped at him but took off in the other direction.

Stiles pushed himself up onto his elbows before freezing when the new Alpha skidded down the hill and stared down at Stiles with glowing red eyes, fangs on full display. Stiles whimpered as he felt his eyes flash omega gold in reply, a strange calm surrounding him and something just clicked inside of him.

“Alpha,” Stiles breathed out as he realized that this was the feeling every love song and book described when true mates met.

“Omega,” The Alpha rumbled in reply, Stiles shuddered as he lifted himself upright. The Alpha towered over him and Stiles felt his body twinge in excitement as his mate’s scent engulfed him.

“Omega, my Omega,” The Alpha murmured and Stiles found himself backed up against a nearby tree. Stiles bared his throat in submission on reflex and shivered when the Alpha shoved his face into the Omega’s neck. Stiles whimpered when he felt the Alpha’s fangs graze at his unbroken mating gland and he felt slick begin to slip down his bare thighs.

The Alpha pulled back, nose flaring and sharp ears twitching as he took in the scent of the Omega’s arousal. Stiles traced the Alpha’s sideburns and let out a shaky breath.

“My Omega,” The Alpha rumbled as he ducked his face back into Stiles' neck, large rough hands cupping Stiles naked ass.

“Whoa, there big guy!” Stiles squeaked when he felt the Alpha’s claws nearing one of his most sensitive areas.

“Claws are a no go, yeah?” Stiles said and the Alpha pulled back to give Stiles a confused look.

“…Okay, here let me do this part big guy,” Stiles wondered absently if this Alpha was feral, then decided it didn’t matter because feral or not they were mates. The Alpha huffed but relented and began to run his clawed fingers over every inch of Stiles naked body. Stiles settled into the touches as he reached behind himself the best he could with the rough bark of the tree against his back. Stiles whimpered as he pressed two of his fingers into his slick hole. Stiles twisted and hooked his fingers in a familiar movement from his many nights alone and had to grab onto the Alpha’s bicep for balance when he brushed over his own prostate with a whine.

The Alpha rumbled at the sight and sounds of the Omega fingering himself, readying himself for the Alpha’s cock. Stiles breathed out as he withdrew his wet fingers and looked up at the Alpha’s face, his own eyes still shining golden.

“Alpha,” Stiles keened and the Alpha brushed their faces together in a tender movement. The Alpha gripped Stiles' thighs and easily lifted him up and pressed him against the tree behind him. Stiles wrapped his legs and arms tightly around the bulky Alpha and let out a keen of pleasure as the Alpha pulled Stiles down onto his erection without pause.

Stiles tossed his head back with a cry at the sensation of being impaled on the feral Alpha’s thick cock, being opened up so wide and at the same time being so full. It was intoxicating in the best way possible and Stiles was enjoying it completely. Stiles dragged his fingers through the Alpha’s hair, clinging to the werewolf tightly.

The Alpha let out a content purring noise against Stiles collarbone, obviously enjoying being inside of his Omega. Stiles let out a keen when the Alpha tightened his fingers on Stiles' thighs and began to move him. Stiles gasped with his eyes rolling up into his skull as he was bounced up and down on the feral Alpha’s cock. Stiles moaned and mewled as the Alpha’s cock pressed against his prostate each time he was pulled back down onto the Alpha’s length.

Stiles all but screamed out as he was impaled hard on the Alpha’s cock one final time forcing his orgasm out of him hard and fast. Stiles’ cock spurted cum over the Alpha’s chest as the Alpha’s knot began to swell inside of the Omega’s wet, fluttering hole.

Stiles leaned his head back against the tree behind him, greedily gasping in air as the Alpha’s cock pumped him full of cum. Stiles absently put his right hand on his stomach, feeling it began to distend with his Alpha’s knot and cum.

“I’m Stiles,” Stiles said still dazed from his orgasm and the satisfaction of having the Alpha knotted to him.

“D-Derek,” The Alpha forced out, eyebrows furrowed together.

“Derek,” Stiles hummed as his eyes fluttered shut as Derek nuzzled their cheeks together.

“My mate, my Omega.” Derek crooned happily and Stiles let out a soft mewl of pleasure.

“My mate, my Alpha,” Stiles replied just as happily. They would figure everything out later even if Derek lived with actual wolves, they would make it work.

Chapter Text

“Has the Omega’s training been completed yet?” Peter asked the director of the clinic he had been coming to for years, but this time he wasn’t there for himself.

“Oh yes, Alpha Hale, Stiles will meet all your requirement’s. He’s rather greedy if you don’t mind me saying, he never seems to be stated and we had to start locking him chastity just to get him to engage in the classes.” Mr. Brenner said as he slid a file across his desk allowing Peter to pick it up and open it.

“Oh, he’s perfect.” Peter purred as he took in the photos attached to the file. The Omega was young and pretty, freckles dotting pale skin and whiskey-colored eyes. In the photo he had his pink lips stretched around a fake wolf cock, the bulge in his throat showing how deep he was taking it and a fucking machine was shoving another fake wolf cock deep into his wet hole. His omega cock was locked tight in a metal cage that went around his balls as well and his face was showcasing pure bliss.

“He’ll make an excellent breeding bitch, prepare him for me. My nephew will be quite pleased with his new Omega.” Peter closed the file and Mr. Brenner beamed at how the transaction went.

“Of course Alpha Hale, it is a pleasure doing business with you.”

An hour later Peter was entering the loft that belonged to his nephew. Stiles’ was standing naked save for his chastity cage and collar, head bowed by Peter’s side, but the wolf could smell his excitement and arousal.

“Do you know why you had been trained using fake wolf cocks and not normal human or werewolf ones?” Peter asked as he tugged on the leash that was around his hand connected to Stiles’ collar.

“No Alpha Hale,” Stiles murmured.

“That is because my pack’s breeder is my nephew Derek but he rarely shifts out of his wolf form. I needed an Omega who would be able to be bred by a full wolf and you dear Stiles are that Omega now.” Peter explained and Stiles’ arousal spiked up in excitement.

“Oh yes you are perfect, now present yourself for the pack’s breeder,” Peter ordered, watching as Stiles easily obeyed and dropped to his knees.

Stiles’ went into the classic face down ass up position by Peter’s feet and felt slick slip from his hole and he whined lowly when he heard the telltale clicking of wolf paws on the hardwood floors and the heady scent of a breeder enter the room.

“Ah nephew, I see you are ready to meet your new bitch,” Peter said smugly as he nodded at the large black wolf whose blue eyes were trained on Stiles’ naked and presenting body.

Derek padded closer and inhaled the Omega’s divine scent and swiped his long, rough tongue over Stiles hole, tasting his slick. The Omega keened at the feeling and gasped when the wet appendage shoved into him without hesitation.

“That’s good Derek, taste the Omega, enjoy it,” Peter said, eyes glowing Alpha red as he watched the large wolf spear the Omega’s hole open on with his tongue.

Derek pulled his tongue free and huffed warm air over Stiles soaked and clenching rim, the Omega giving little gasps as his body shook. The wolf nudged his furry head against the small of Stiles back in something like comfort before he shifted his forelegs so they were on either side of Stiles’ body and he shoved his large, dripping wolf cock between the Omega’s cheeks. Stiles whimpered at the feeling of the wet length against his skin and he ached for the real deal instead of the cold plastic toys he had been using before.

“Go ahead Derek, make the pretty Omega your bitch.” Peter encouraged as he began to palm himself at the sight below him.

Derek snapped his teeth at Peter before his furry body shifted forward and Stiles let out a high-pitched cry as the wolf’s cock penetrated him fully. Stiles’ eyes glowed Omega gold as his head snapped up, face slack in bliss and mouth opened lewdly as Derek began to roughly fuck into him from behind.

“Feels good doesn’t it Omega? Having a proper wolf cock inside of you?” Peter knelt down in front of Stiles, pulling at the leash as he spoke forcing Stiles’ head to stay upright.

“Yes, oh God yes Alpha Hale.” Stiles’ gasped out as Derek began to pound into him from behind, his furred and heavy balls slapping against his ass and his own caged ones obscenely.

“You’re the Hale pack’s breeding bitch now, you will only service Derek and myself and on occasion anyone else I decide to lend you to,” Peter said firmly.

“Yes, Alpha Hallllee!” Stiles’ cried out at the end as the wolf cock inside of him hit against his prostate making him see stars.

“Open up bitch,” Peter ordered as he unzipped his pants, jerking himself off right above Stiles’ tipped head. Stiles kept his eyes on Peter and opened his mouth wide, his body being forced forward with each hard thrust Derek was giving into him from behind.

“Such a good little bitch, taking that wolf cock so well,” Peter grunted as he watched as Derek’s wolf form shifted and twisted as he fucked into the Omega’s messy hole with growls falling from his mouth and glowing eyes trained on Stiles’ from below him.

Stiles rocked back to meet the wolf’s thrusts as he kept his mouth for Peter. Stiles moaned as warm cum dropped into his mouth as Peter climaxed, making sure to fill Stiles mouth with his release.

“Swallow every last drop, ah there’s a good Omega,” Peter smirked as Stiles’ Adam apple bobbed and he opened his mouth again to show the Alpha of the Hale pack that he had swallowed all of his cum.

Stiles suddenly choked and dropped his head back onto the floor as he felt Derek roughly shove his swelling knot into him from behind. Stiles’ keened and gasped, it felt so good inside of him, spreading him wider and wider, locking them together.

“Now you’ve been properly bred by a Hale,” Peter was smug as he watched Stiles mind leave him and his stomach begin to extend as Derek flooded Stiles body with his cum.

“Mmm, thank you.” Stiles hummed, completely out of it as he enjoyed the feeling of loads and loads of hot cum being pumped into him. This was something he could get addicted to and he was finally stated even with his own orgasm denied and he wanted this again and again.

Chapter Text

Stiles' eyes fluttered open, he had no idea that he had even passed out. The last thing he properly remembered was being held against a tree in Derek’s arms, impaled on the feral Alpha’s knot.

Now he was flat on his back on a cot made of soft moss that was surprisingly comfortable, but he was still fully naked and his thighs and hole sticky with dry cum. Stiles inhaled sharply when his gaze fell on what surrounded him.

“Oh my god, he actually lives with wolves. What the fuck.” Stiles whispered as he took in the wolves milling about him, two males getting closer to him looking a bit too interested.

“Oi, get away.” Stiles protested when the wolves sniffed at him, teeth bared as they took in his Omega scent. Stiles let out a breath of relief when a familiar snarl echoed out and Derek was standing between Stiles prone form and the two wolves. His eyes glowing a bright Alpha red and his fangs snapping at the wolves, the animals snapped back for a moment before whining and sauntering away. Derek growled lowly one last time before he faced Stiles and fell to his knees by the Omega’s side.

“S-Stiles, o-okay?” Derek stuttered out, face set in determination as raspy words came from his lips.

“I’m okay big guy, just a bit confused.” Stiles couldn’t help but beam at his mate who was trying so hard to talk again just for Stiles benefit.

“D-Don’t smell c-c-claimed.” Derek huffed out in frustration as he got the words out.

“I’m literally still leaking your come big guy, how can I not smell claimed?” Stiles asked in confusion as he racked his brains for why the wolves might not think he was Derek’s. One thing at a time and maybe Stiles wouldn’t go crazy considering his Alpha was officially feral and living with a wolf pack in the woods.

“N-Not f-fully c-claimed.” Derek ducked his head, cheeks and ears turning a nice shade of pink that had Stiles silently cooing before a fact he had learned from a nature documentary smacked him upside the head.

“Oh…Oh! Marking your territory, ahem, right…” Stiles felt his own cheeks burn even as his cock twitched at the idea.

“So you want to knot me full of your cum and piss? Show the others that you’ve claimed me?” Stiles lowered his voice as he pulled himself up onto his knees, pressing himself flush to Derek’s chest.

Derek whined in the back of his throat and he ducked his face down against Stiles mating gland again. Stiles ran his fingers through Derek’s hair with one hand and caressed the Alpha’s shaft with his other.

“Go ahead Alpha, claim your Omega.” Stiles crooned in the Alpha’s ear unable to stop the fresh wave of slick that dripped from his flexing hole. Derek growled loudly and Stiles gasped as he found himself suddenly face down on the moss. Derek’s claws dug into his hips as the Alpha forced Stiles knees up so his ass was presented perfectly.

“Derek! Alpha!” Stiles moaned out as the Alpha sank his cock into the Omega below him. Stiles clawed at the ground, his own smaller claws and canines extending as his eyes pulsed Omega gold as his body opened up for his mate’s cock.

Derek didn’t wait long once he was fully sheathed inside of Stiles tight, wet heat. The need to claim his mate in the way of the pack he had been a part of for years drove him as much as his instincts did. Derek started to rough thrust in and out of his Omega, his heavy balls smacking against the younger man’s upturned ass lewdly as more slick from his Omega eased the way.

Derek snarled out as he flashed his Alpha eyes at the watching wolves that were unclaimed, he wanted to make sure they knew who the Omega below him belonged to. Stiles was writhing and crying out below the Alpha as he took every rough thrust beautifully, claws leaving marks in the dirt and sinful noises falling from his plump lips. Derek preened at being able to turn his perfect Omega mate into this much of a mess with just a few thrusts.

Stiles cried out Derek’s name when the Alpha adjusted his angle and hammered against his swollen prostate. Stiles saw white as his balls drew up tightly and his cock spurted out his release. Soon Stiles’ was limp on the ground, only being held up by his Alpha’s hands on his hips as he was driven into.

Stiles turned his head to the side and keened when he felt Derek’s throbbing length pause deep inside of him and a slowly growing familiar sensation of cum being emptied into him overcame Stiles senses. Derek massaged the lower part of his stomach once he had emptied a load of his cum into his Omega and made a noise of content as his cock twitched and the scent of semen and urine filled the air.

Stiles crossed his arms and buried his face into them as he felt his Alpha’s piss join the mess of cum that was inside of Stiles ass. It was humiliating yet primal in a way Stiles hadn’t expected. Stiles whimpered when Derek thrust into him again, forcing some of his cum and piss out of Stiles’ ass and down his thighs. Stiles wailed into his arms when Derek’s swelling knot caught on his rim before they were tied together again.

“Mine, my Omega.” Derek crooned happily as he kissed up and down Stiles spine as his knot kept his claim firmly plugged up inside of the Omega below him.

“Alpha,” Stiles relaxed knowing the Alpha’s knot would last a while and wondered if this was going to be a usual thing, being fucked hard and then knotted full of piss and cum. His inner Omega was crooning in contentment in a way it never had before so Stiles just enjoyed it as he was pumped full of his Alpha’s cum once more. At least the wolves would leave him alone now that he was properly claimed in their eyes.

Chapter Text

“Are you sure you want to go through with this?” Derek asked as carefully tied the black blindfold securely around Stiles' eyes, caressing his lover’s cheek once the fabric was in place.

“I’m sure Sourwolf,” Stiles said fondly, placing his hand blindly over Derek’s that was still resting on his cheek.

“They all know the rules, what is good and what isn’t. They know your safe word and motion, we’ve thought of everything.” Derek said aloud mainly for himself as he and Stiles had gone over this repeatedly before coming to stand outside of the room where a bunch of Derek’s werewolf friends were waiting inside.

“We have, now let’s do this.” Stiles leaned forward for one final kiss that Derek happily gave. Derek took a small breath as he held up the O ring gag and Stiles willingly parted his mouth, allowing Derek to fasten it in place before Derek laced their fingers together and led Stiles forward into the room.

“My, my Hale you weren’t kidding about how pretty he is.” Was the first comment that reached Stiles’ ears while a low mummer of approval rang out from the others in the room. Stiles shivered at the feel of many eyes trained on his body, he hadn’t been told the number of werewolves in the room at his own request and his body was reacting to the unknown.

“Why would I lie about that?” Derek huffed and Stiles could just tell his mate was rolling his eyes and Derek’s hand nudged him forward a bit further until their fingers dropped free and Stiles was standing blindfolded, mouth open around the gag and alone in the middle of the room.

“So you’re offering this pretty thing up to be our little breeding bitch for the night?” Another voice asked as Stiles startled a bit as rough fingers tweaked his nipples making him give a small mewl at the pinching sensations.

“That’s right, he needs to learn his place,” Derek stated firmly and Stiles let his head fall back when another hand gripped his hair and a hot tongue licked a strip up his now exposed throat.

“Oh don’t worry, he’ll know it very well by the time we’re all through with him.” The man holding his hair purred and Stiles keened when the wolf’s teeth grazed over his neck just enough to tease the skin into goosebumps.

Stiles went willingly to his knees when the hand in his hair began to push him down and soon Stiles found himself on all fours before his head was pressed to the floor by the foot of one of the men. He was now in the perfect presenting position and he heard growls of approval from the others in the room as large hands groped his ass and parted his cheeks wide.

“Look at that men, the bitch is wet like it’s in heat.” The man holding his ass cheeks apart laughed as he shoved two fingers into Stiles hole without any presumable and Stiles moaned wantonly at the rough treatment. Derek had spent tender hours working him open so he was loose and wet, ready to be mounted and bred by the others in the room.

“Tight little thing, don’t you fuck it open enough Hale?” The man was pumping his fingers in and out of Stiles as he spoke.

“I like it’s pussy tight,” Derek said unbothered and Stiles whimpered against the carpeting of the room, his cock was hard and beginning to strain against the cage Derek had locked onto him. That was one of his conditions of this, Stiles wouldn’t reach his full orgasm until it was all finished and Derek was the one to give it to him.

“Good call, but sorry to tell you, Hale. This bitch’s pussy is gonna be a loose, sloppy mess of cum by the time we’re finished here.” Another wolf called out and the others made pleased noises of agreement.

They all fell abruptly silent when Stiles let out a loud cry from behind the strict gag sounding very much like an actual bitch in heat when the man who had been fingering him replaced his fingers with his cock. Stiles dug his fingers into the carpet as the unfamiliar cock slammed into him from behind. It was rough, thick and unknown and Stiles loved it. He opened his legs wider for the wolf slotted between them and moaned as the man began to fuck into him with abandon, grunting as his balls smacked lewdly against Stiles upturn ass with each forward thrust.

“Is the bitch’s pussy good?” A man called out and Stiles shuddered at the reminder that there were many others watching them, including Derek and his cock twitched in its restraint.

“So fucking good, you brought us a good one Hale.” The man grunted from his place behind Stiles, never wavering in his thrusting. Stiles keened when the man suddenly stilled, cock buried inside of him and he felt the wolf’s cock pulse once, twice and soon the man was spilling into him.

The man pulled his spent cock out of Stiles ass with a wet pop and Stiles let out a small breath when he felt some of the man’s load drip down his thigh and low groans were heard from around the room as they all stared at the sight.

“Who's next?” Derek asked lazily and that snapped the others out of their haze.

Stiles let out a gasp as a hand gripped his hair and pulled him up so he was on his knees, he barely managed to gather more air into his lungs before a long cock was being shoved between the gag. His tongue instantly began to swirl around the hard flesh and he began to breathe through his nose as he sucked eagerly at the cock.

“The bitch’s mouth is damn good,” The man Stiles was sucking off commented as he let Stiles suck at him at his own pace.

“A cock in its mouth is the only way other than a gag to keep it quiet.” Derek agreed and Stiles hummed around the wolf’s cock knowing Derek wasn’t wrong about that. The man gripped Stiles hair tighter at the action and Stiles found his hands being lifted up and wrapped around cocks. He had one in each hand and he began to stroke and pump the hard cock’s, even as large mans gripped his legs, pushing them apart.

Stiles kept sucking and stroking as another man settled below him so Stiles was straddling his lap backward. Stiles swallowed around the cock in his mouth as the head of an unfamiliar cock nudged at his hole and with a swift jerk of his hips, the werewolf was sheathed inside of Stiles. Stiles moaned around the cock in his mouth unable to stop himself as he was bounced quickly up and down on the cock that was now inside of him.

The lewd sounds of flesh on flesh sounded out, Stiles could feel the first load of cum inside of him being pushed both deeper into him and out of him at the same time by the new cock. Stiles began to get a bit lost in the way the cock in his ass felt, the men he was stroking began to fuck his slacken grips, not willing to lose their own releases.

The man in his mouth used his hold on Stiles' hair to take control now and was rapidly thrusting in and out of the ring gag, using Stiles mouth for his own pleasure. Stiles closed his eyes behind the blindfold, feeling drool slipping out of the corners of his mouth as he gagged around the hard length and moaned as the man fucking up into him hit against his prostate.

Stiles caged cock was bouncing against his stomach as he was fucked; pre-cum leaking from between the metal bars and Stiles felt the cage pushing back his own release. Stiles suddenly choked as a flood of hot cum rushed over his tongue and down his throat as the man in his mouth let out a howl of pleasure. Stiles tried to swallow the best he could but some still spilled out of his mouth and down his chin and neck. Stiles felt warm splashes of cum hit his cheeks on either side as the men in his hands came as well with their own cries of pleasure.

Stiles coughed the best he could from behind the gag when the now limp cock was pulled out from his mouth and his dirtied hands fell to his sides as the three cocks shifted away from him. The man whose cock Stiles was seated on gripped Stiles' knees and held them up, spreading them wide for the others to see where the two were connected. Stiles let his weight fall back on the man who was growling lowly as he roughly thrust up into Stiles now and Stiles mewled as the man snarled out his orgasm and added his own load into Stiles body.

Stiles was lifted up off of the man’s cock and laid out flat on his back, his legs wide so everyone could see the small puddle of cum that was forming under his ass. His cock was angry and dripping against his stomach, his nipples erect and puffy from his own arousal and his face coated in three loads of cum.

“You’re not properly bred yet, this pussy needs at least a few more loads of cum before that can happen.” A man commented as hands lifted up Stiles legs, resting them over a pair of shoulders and Stiles arched up off the floor as a hard cock was shoved into his cum slick hole. His eyes rolled up into his head as he clenched his fingers in the carpet as the new man began to pound into him ruthlessly, cock hammering against Stiles prostate over and over until Stiles was writhing uselessly on the floor and cock straining even harder against the cage.

“Open wide bitch,” A man ordered as Stiles felt a pair of balls drag over his face obscenely before a different cock was shoved into the ring gag and Stiles choked around the girth. The man gripped Stiles hair, lifting his head up off the ground for a better angle and he began to jerk his hips forward, using Stiles’ mouth like it was just another hole.

Stiles sucked and twisted his tongue the best he could but soon even that was too much for him as the man roughly used his mouth and the other man fucked deeper into his ass. Stiles made a muffled noise when the man in his mouth, drove his cock right to the back of Stiles' throat and emptied his load down Stiles' throat. Stiles swallowed over and over again before gasping when the cock slipped free of his mouth and he felt at least two spurts of cum hit his chest and neck when the man shifted off of his chest. Stiles arched again when the man inside of him throbbed and added his own release to the two other’s inside of Stiles. It was hot and messy and everything Stiles had hoped this would be.

Stiles gave a weak keen when four fingers easily thrust into his sloppy hole and hooked at his rim making him spread his legs wider.

“The bitch’s pussy is ready for two I think,” Derek commented and Stiles jerked as he realized it was Derek who was between his legs and had his fingers inside of his cum drenched hole that was sure to be a gaping mess now.

“Fucking finally, we’ve been waiting for this.” A new voice commented and Stiles shuddered realizing there were at least two more men who had been watching but hadn’t taken part yet waiting for him.

“Go on then,” Derek said as he withdrew his cum covered fingers and cleaned them on Stiles right thigh making Stiles for some reason blush, he hadn’t blushed at anything else but that action made his heart beat faster; it had to be because it was Derek who did it.

A few sets of hands were now touching Stiles body and Stiles allowed them to move his prone form wherever they wanted him. Stiles figured he was facing one of the two men who had been waiting when their chests connected. Firm hands were holding his ass cheeks firmly and Stiles fumbled as he scrambled to grab onto the wolf’s shoulders. Stiles' head tipped back when he was lowered onto a thick cock, pushing some of the cum from the others out of him and down his thighs as Stiles took each inch of the man’s cock.

“The bitch’s pussy is fucked open all right, should be no problem fitting two of our cocks into it.” The man who was now fully inside of Stiles commented as he tugged Stiles ass cheeks apart, showing everyone the sight of them connected.

Stiles whined from behind the gag as two rough fingers pushed into his mouth, just giving him something to keep his mouth busy as the head of another cock rubbed at his already full hole. Stiles exhaled through his nose as hands that were rough only mere moments ago became tender as they caressed his body, rubbing his nipples and stroking his hair as a second cock was eased up into him.

Stiles sucked absently on the fingers in his mouth as his eyes stung at the extra stretch and pressure. His cock was aching something fierce but the feeling of being so, so full was overpowering and Stiles couldn’t focus on anything anymore.

“Now you’re a proper breeding bitch, taking two cocks at the same time.” The man Stiles was straddling crooned as he kneaded Stiles ass cheeks once the second cock was snugly seated inside of Stiles body. Stiles let out a wounded noise around the fingers in his mouth as one of the men gave a shallow thrust, it was like every nerve in his body was on fire and Stiles wanted more.

Stiles gripped the wolf’s shoulders and bounced a bit just to get the message across and new hands held his hips in place.

“Greedy bitch you have here Hale,” The man behind Stiles stated breathlessly.

“You’re telling me,” Derek said sounding fond if not breathless himself making the tips of Stiles' ears burn. Stiles moaned wantonly around the fingers and gag when the two men inside of him began to move, the stretch and slide of their cocks were sinful and Stiles lost track of everything. Stiles just clung to the man he was straddling for all he was worth as he found himself being rocked forward by the force of their now fast and hard thrusts or being pulled down to meet their thrusts, he couldn’t tell anymore in the haze of pleasure and the light burn of the stretch.

Stiles was snapped out of the haze when one of the men cried out in his ear and snapped his hips up against Stiles ass, adding his own load into Stiles before the second man with a howl followed. Stiles whimpered when he was lifted up off both cocks a few moments later and settled between someone’s legs, he nuzzled the man’s thigh and relaxed when he picked up Derek’s familiar scent and heavy hand in his hair.

“Go on, show them all your bred pussy while you get me off. Then I’ll get rid of that cage for you.” Derek crooned as he petted Stiles' hair. Stiles lifted his head towards Derek’s voice and worked his jaw when Derek removed the gag. Derek guided his head forward until the head of his cock bumped against Stiles' mouth. Stiles happily parted his lips, ignoring his sore jaw and began to suck at Derek’s cock in the way the werewolf liked it.

Stiles shifted onto his knees before reaching back and gripping his own ass cheeks, relaxing his slightly clenching hole as he spread himself wide showing off his cum dripping, gaping hole. It made his cheeks burn but the noises and words of approval made that disappear fast enough, he felt proud that he had taken every single one of them, that he had made them all feel good and made Derek proud of him. Stiles swallowed down Derek’s release a moment later, which was how he knew Derek was proud of him, Derek’s cum was a reward and a reclaiming.

“Thanks for the good time Derek, see you next month for drinks?” The first man who had spoken that night asked as clothes rustled behind them as Stiles nursed at Derek’s softening cock, still holding his ass open for them all to see.

“You got it,” Derek agreed as he threaded his fingers through Stiles' hair.

“Thank your pretty little mate for us later when he’s more aware.” Another called out and Derek hummed his agreement and soon the room fell silent after a door opened and shut.

“You did so well for me Stiles, you were so good for all of us. You made me proud you know that right?” Derek crooned as he eased Stiles up onto his lap, deftly unknotting the blindfold and smiled widely when hazy whiskey-colored eyes blinked at him.

“Yeah?” Stiles asked dazed, voice hoarse and rough from taking so many cocks.

“Yeah, let’s give you a proper reward before we get you into a bath okay?” Derek cupped the cage and Stiles bucked into the first touch he had there all night. Stiles clutched at Derek’s hair as the pressure was slowly relieved as Derek unlocked the cage and slipped it off. Stiles let out a sob when Derek rubbed his thumb over the wet slit and his orgasm exploded out of him in such force that Stiles world went black, Derek’s strong arms around him and soothing words of praise in his ears.

Chapter Text

It wasn’t something that Derek ever thought would be something that would appeal to him. Being with Stiles had changed a lot of things and Derek’s view had expanded beyond the horizon and was, in fact, trying things in and out of bed he never thought he would do.

That was being shown right now as Derek gently eased his cock out of Stiles’ ass, he had just knotted Stiles for the first time since they got together. Stiles’ was half asleep from where he sprawled out on his stomach on their King sized bed. Derek wasn’t focused on that right now, instead, his eyes were stuck on Stiles hole.

His knot was not small and it showed in a way that had both Derek’s human and wolf side preening and glowing with pleasure and arousal. Stiles’ hole was gaping. Derek had seen photos online but nothing in real life and it was stunning. Stiles’ rim was fluttering like it was trying to clench back to its original shape but couldn’t.

Derek’s knot had stretched him open so wide and loads of cum that he had pumped Stiles full of moments ago was slipping out of him and down his thighs and onto the bed below. Stiles’ hole couldn’t keep it all in and it was the lewdest and beautiful thing that Derek had ever seen.

Derek couldn’t resist as he lightly traced Stiles’ gaping rim with his index finger and watched as more of his cum gushed out of Stiles open hole.

“Mm? Derek?” Stiles slurred roused slightly by the touch on his hole and he peered over his shoulder to look at him.

“What’s wrong?” Stiles blinked slowly as he took in the sight of awe and arousal on Derek’s face.

“You’re so open, you’re just gaping Stiles.” Derek murmured as he hooked his finger against Stiles rim and tugged, whining when the muscle stretched wider still.

“I know? I gaped so many times while I training to take your knot. By the end, I could take a soda can and that’s when I knew I was ready.” Stiles hummed as he closed his eyes, snuggling his face against the pillow below his head.

“Fuck,” Derek breathed at the mere thought of Stiles hole stretched wide around a soda can.

“I can show you if you want?” Stiles suggested sounding half asleep and Derek’s eyes widened and his cock gave an interested twitch.

“Yes,” Derek breathed and Stiles opened one eye to look at Derek before a lazy smile crossed his lips.

“Once I’m tight again I’ll show you, it would be too easy if I took it after I got gaped by your knot,” Stiles promised and Derek growled at the words as pride surged up at the reminder he had knotted his mate and caused him to be this open.

“Come here sourwolf, I’m exhausted and cold,” Stiles whined as he lifted one arm weakly. Derek plastered himself around Derek and kissed over his freckled face while Stiles sighed happily.

“Promise you’ll show me?” Derek asked unsure suddenly.

“I promise Derek,” Stiles said with a kiss to Derek’s chin before he fell asleep in the wolf’s embrace.

It was a month later that Stiles had bounced into their flat with a cocky smile on his lips and pinned Derek the counter in their kitchen.

“Are you ready sourwolf?” Stiles asked as he planted kisses over Derek’s throat.

“For?” Derek raised an eyebrow in question.

“I made you a promise that night after you knotted me, meet me in the bedroom.” Stiles winked before sauntering towards their bedroom. Derek stood stock still for a moment before the image of Stiles gaping and soaked in his cum and their conversation flashed into his mind. Derek’s cock swelled instantly and his eyes flashed blue as he took off towards their bedroom.

When Derek arrived Stiles was already naked and had an unopened but full soda can resting on the bed next to a bottle of lube.

“Take a seat and watch the magic happen sourwolf.” Stiles winked as he twisted his body so he was bent over the edge of the bed. Derek sank into a chair that was directed at the bed and his cock twitched as Stiles slowly pulled a fat butt plug out of his ass with little groans falling from his lips.

“Had to do some prep work beforehand,” Stiles admitted as he tugged his ass cheeks apart to show Derek how his hole was already beginning to be stretched and Derek had to clutch at the arms of the chair for balance as a shot of arousal went through him.

“Now this is going to be slow going so have some patience okay?” Stiles settled himself up onto the bed, his legs draped over his own arms as he inserted the tip of the bottle of lube into his hole. Derek nodded as he swallowed hard at the sight of the bottle disappearing into Stiles. Stiles shuddered as he squeezed the cool lube into his ass and tossed bottle aside before picking up the can.

Derek leaned forward onto his knees, eyes glowing blue in the room as he watched with bated breath as Stiles rubbed the bottom of the can against his wet hole.

“This is the tricky part,” Stiles admitted breathlessly as he reached down with his free hand and tugged at his rim. Derek inhaled sharply when Stiles moaned loudly as the rounded end of the can slowly begin to sink into his hole.

Stiles let out a shaky breath as he ever so slowly edged the can deeper into him and Derek was an inch from falling off of his chair as he watched entranced.

“Fuck,” Stiles panted as he took a break the moment he got half of the can buried inside of himself.

“You’re perfect,” Derek whispered in amazement as he finally gave in and approached the bed, laying his hand on Stiles' stomach as he stared at the way the can was obscenely sticking out of Stiles.

“Derek,” Stiles’ eyes fluttered before moaning loudly when Derek gently nudged the can a bit deeper.

“Help me, make me gape around this can.” Stiles latched onto Derek’s arm, eyes hazy and lips parted wide as his tongue flicked out and wet his lips.

“You are perfect,” Derek repeated as he throbbed in his pants as he got a good grip on the can. Stiles arched with a whine when Derek slowly rocked the can, pushing it deeper each time. Stiles’ rim clung to the metal desperately and it only spurred Derek on.

“How does it feel?” Derek whispered as he slowly twisted the can making Stiles cry out and clung harder to his arms.

“So full, stiffer than your knot and almost as wide.” Stiles babbled as he writhed when Derek gave a final nudge so the can was almost fully inside of him, the furthest Derek was willing to push it into him.

“You’re so open around the can, fuck Stiles you have no idea.” Derek knelt down on the floor by the end of the bed so he was eye level with Stiles’ stuffed hole, tracing the soft skin of his rim again. Stiles clutched at his quivering legs and mewled at the touches before shouting outright when Derek flicked his tongue over his hole.

“Fuck me with it, Derek, fuck me with the can.” Stiles panted, sweat plastering his hair to his face and his cock heavy against his stomach, already leaking pre-cum.

“Fuck,” Derek swore as he got his fingers around the end of the can and slowly began to pump the solid can in and out of Stiles. Stiles cried and squirmed as his hole was forced open wider with each movement of the can.

“I wanna see you gape, Stiles, I need to see it.” Derek panted as he used his free hand to palm his tented pants.

“Take it out, fuck I want you to see me gaping Derek.” Stiles lifted his head up to look at Derek with hazy eyes and flushed cheeks.

Derek tugged the can out and tossed it to the side before parting Stiles ass cheeks wide so he could get a good look. Stiles’ was indeed gaping again, it wasn’t as large as the gape he had when Derek had knotted him but it was easier to see. Stiles’ rim was still twitching and loosely clenching around the empty air and Derek had an urge to see Stiles loose hole drenched in his cum again.

“I’m going to cum in your gaping hole Stiles,” Derek decided as he rose to his feet, hands scrambling at his pants as Stiles keened high in his throat.

“Please Derek, oh fuck.” Stiles reached down with shaky hands and held his own ass open as he watched as Derek pulled his cock out of his pants. Derek kept his eyes locked on Stiles’ loose hole as he grunted as he roughly jerked himself off, his climax easy to attain this time.

“Put the head inside of me, come in me properly Derek,” Stiles demanded and Derek hurried to comply. He had just pushed the head of his cock into Stiles gaping hole when his cum spurted from the head and flooded into Stiles. Some already began to drip from his open hole but most stayed inside even after Derek pulled back.

“So filthy,” Derek mused at the sight of Stiles’ filled and leaking gaping hole.

“You love it,” Stiles said breathlessly before crying out when Derek jerked him off with quick motions. Stiles went slack on the bed with his legs parted wide as his cum cooled on his stomach and more escaped from his gaping hole.

“I love you, Stiles,” Derek said as he dragged his fingers around Stiles rim again.

“Love you too sourwolf, you and all your kinks.” Stiles smiled as he closed his eyes content to let Derek take his full.

Chapter Text

Stiles moaned happily as Derek kneaded his ass as the two kissed passionately.

They were sitting on the couch in the living room of Derek’s home, Stiles straddling the older man and the movie playing in the background forgotten about completely. Stiles was raking his fingers through Derek’s dark hair as they kissed, Stiles pulled away to gasp for air while Derek nuzzled at his neck, kissing and nipping at the freckled skin almost lovingly.

“You know, this is our third date.” Stiles started sounding breathless as he kept petting Derek’s hair as he allowed the Deputy to suck at his neck, leaving his marks behind.

“I think the third date sex rule doesn’t apply to us,” Derek grunted out making Stiles laugh.

“Yeah not so much, but I do have something to ask… I didn’t really get a good look the last two times, so will you let me see you?” Stiles asked once Derek looked at him and Stiles smiled softly when a light pink spread over his cheeks at the request.

“On your knees then,” Derek decided and Stiles made a noise in the back of his throat as he slipped off of Derek’s lap and onto his knees in front of the werewolf. Derek caressed Stiles jawline for a moment before he lifted his hips up as he unzipped his pants and pushed them and his boxers down to his knees. Stiles made a weak noise as he stared at his lover’s erection.

“You’re so big Deputy Hale,” Stiles crooned as he leaned forward, wrapping his fingers around the man’s girth. His fingers barely touched when they closed, Derek was at least 8 or 9 inches, he easily had the biggest cock Stiles had ever seen and his balls were large and full making Stiles mouth water.

“Do you like that?” Derek asked lowly as Stiles began to stroke him slowly, Stiles lips already parted and Adam’s apple bobbed as he swallowed down the salvia that was pooling in his mouth.

“Yeah, fuck I really do. I was gaping for days after you fucked me, I love how big you are.” Stiles admitted as he dragged the flat of his tongue up the underside of Derek’s cock, moaning at the taste of him on his taste buds while Derek let out a low growl at the wet touch.

“Someone is a size queen,” Derek mused and Stiles’ cheeks flushed as he flicked his tongue over the tip of Derek’s cock.

“I’m not denying it, Deputy Hale.” Stiles purred as he looked up at Derek who was flushed and a bead of sweat was rolling down his temple.

“Let’s put that pretty mouth to work hmm?” Derek suggested as he tangled his fingers in Stiles' hair, holding him firmly.

“Mm, yes Deputy Hale.” Stiles winked as he parted his lips and kept eye contact as he took Derek into his mouth. Derek moaned as the warm, wet heat engulfed his cock and God the sight of Stiles’ lips spreading out around his cock was something to behold.

Stiles’ eyes fluttered as his mouth was filled and lips stretched out as he took Derek into his mouth. Stiles choked a bit before backing off so he didn’t gag around Derek. Stiles was pleased he couldn’t fit all of Derek’s length into his mouth and curled his fingers around the bit that he couldn’t fit, stroking it slowly as he sucked at the hard flesh.

Derek moaned loudly as his hips bucked slightly as Stiles’ tongue pressed at the slit of his cock and Stiles pulled his head back. His lips parted wide and slick with saliva, giving him a debauched look that had Derek’s cock leak a bead of pre-cum. Derek swallowed down a whine when Stiles eagerly dragged his tongue over his pre-cum and moaning wantonly at the taste.

“You taste good Deputy Hale,” Stiles batted his eyelashes at Derek as he began to lap at the wet slit of Derek’s cock.

“Such an eager slut you are,” Derek praised and Stiles whimpered as his cheeks burned. Stiles ran his tongue over the wet flesh of Derek’s cock before turning his attention to the Deputy’s balls. Derek bucked his hips again as Stiles sucked at his sensitive ball sac and grazed his teeth lightly over the skin there. Stiles dragged his tongue over Derek’s balls and sucked them hard as he pumped his hand up and down the werewolf’s shaft.

“I’m close,” Derek warned, tightening his fingers in Stiles' hair. Stiles pulled off of Derek’s balls with a parting lick to the hard length.

“Come on my face Deputy Hale, I want it so bad,” Stiles whined as he tipped his face up, mouth open wide and eyes closed. Derek made a wounded noise at the sight and gripped his cock, grunting as he roughly jerked himself off. He needed to see Stiles face dripping in his cum, he needed to see Stiles marked as his.

Stiles groaned as warm cum hit his skin, covering his cheeks, chin and some falling into his mouth. Stiles swallowed what he could and he slowly opened his eyes to look up at Derek. Derek was panting and looking spent, fingers curled tightly around his softening cock that was slowly oozing some cum from the slit still. Stiles slowly licked his lips clean of Derek’s cum, moaning at the taste, it was so much better than he had hoped and he wanted more.

“Clean me up slut,” Derek ordered in a hazy voice and Stiles all but lunged forward, taking Derek back into his mouth. Stiles sucked and twisted his tongue over the wet skin, moaning wantonly as he swallowed more of Derek’s cum.

Stiles licked and sucked at the soft cock as his eyes closed and he felt a strange calm settle over his whole being. Stiles let out a soft sigh through his nose as his body all but slumped forward as Derek petted his hair. If Stiles had looked up he would have seen the thoughtful look that appeared on Derek’s face.

“You liked sucking my cock didn’t you slut?” Derek asked as he gently pulled Stiles off his now over-sensitive cock.

“Yes Deputy Hale,” Stiles said in a haze, his own cock hard and leaking in his boxers.

“Get up here,” Derek ordered and Stiles quickly straddled his boyfriend again.

“Ohh!” Stiles cried out when Derek shoved his hand down the front of his pants, groping his erection with a rough hand.

“Look at how hard you got just from sucking my cock,” Derek smirked as he roughly jerked Stiles off, digging his thumbnail into the wet slit of Stiles’ cock earning a cry and an arch of his back.

“One day I’ll have you come just from that,” Derek promised as Stiles scrambled for a hold on his shoulders.

“Please, please, please!” Stiles chanted as he rocked into Derek’s grip needily. Derek took pity on him and twisted his wrist just right and watched as Stiles came with a cry of his name. Stiles shuddered and gasped through the effects of his orgasm with his lips swollen, jaw aching and the taste of Derek’s cum in his mouth. It was mind-blowing and Stiles slumped against Derek, half-consciousness.

“You did so good Stiles, so damn good for me.” Derek crooned into Stiles’ ear making the younger man smile and nuzzle his face into Derek’s neck contentedly.

Chapter Text

“I can’t believe we forgot the beer, I’ll be back in a few minutes okay?” John huffed as he grabbed the keys to his car on his way out the door.

“Okay Dad, we’ll be here when you get back!” Stiles called out from his place curled up next to Derek on the couch, a football game showing on the television. The minute the door shut behind John, Derek had Stiles’ chin in his hand and was tipping his boyfriend’s head up to face him.

“Derek?” Stiles breathed out and Derek just sighed like he was disappointed.

“Oh baby, you promised me that you could handle it and not be a brat,” Derek said sounding disappointed and Stiles let out a soft whine as his body tensed up.

“I’m sorry Sir,” Stiles averted his eyes from Derek and Derek just patted his cheek gently before rising to his feet.

“You know my rules baby,” Derek held his hand out to Stiles who slowly took it.

“I know Sir,” Stiles murmured as he allowed Derek to pull him into the bathroom near the kitchen and close it behind them when they were both inside.

“Do you Stiles? You swore to me if I plugged you up before we came here you would be fine. Yet you have tried to grope me a few times and don’t think I didn’t notice how you were shifting and wiggling against the couch like you were trying to get the plug to move inside of you. You’re lucky your dad was focused on the game,” Derek scolded as he placed his hand on the small of Stiles back and applied pressure until Stiles was bending over the countertop of the vanity.

“I tried not to Sir, but it was against my prostate and I couldn’t help it.” Stiles tried to explain as Derek undid his belt and pulled his jeans and boxers down around his thighs just enough to expose his rear end fully.

“I should have known better than to plug you up with my cum before coming here. You know my rules baby.” Derek balled up a washcloth and fitted it between Stiles' lips. Stiles rested his forehead against the mirror and gripped the edge of the counter in preparation.

“10 right now and I’m afraid when we get home I’ll have to cage you for the night,” Derek repeated their agreed upon punishment for when Stiles disobeyed an order and Stiles nodded mutely.

Derek rubbed his hands together in an attempt to warm them before he raised his right hand and the smack of skin hitting skin echoed in the powder room as Derek struck Stiles’ right ass cheek. Stiles made a muffled noise around the washcloth, digging his teeth into the soft fabric when Derek quickly landed the second hit on his left ass cheek.

Derek rubbed over the spot he had just hit, trying not to get turned on at the way Stiles’ skin was already turning pink in the shape of his handprint. This was not about any of their pleasure and he quickly landed the third smack across both Stiles ass cheeks. Stiles jerked forward at that hit and his knuckles were turning white as he clutched at the edge of the counter, on the next hit that overlapped the stinging spot on his right cheek made his knees buckle against the cabinet and make a noise around the washcloth.

Derek smoothed his hand over the pinking spot before he pressed his fingers against the base of the red plug that was visible from between Stiles’ ass cheeks. Stiles whimpered behind the makeshift gag and his body jerked sharply when Derek brought his hand down on the end of the plug, jolting it deeper into Stiles body. Stiles sobbed around the cloth when Derek followed that hit up with two more in quick succession.

“Almost there baby, 3 more.” Derek carded his free hand through Stiles hair in an attempt at soothing him even as he brought his hand down on the middle of Stiles upturned ass again.

Stiles made another weak noise behind the cloth and squeezed his eyes closed tightly. They were tearing up at the sharp pain that was starting to emit from his ass and the plug only too obvious now. Stiles pressed his cheek to the mirror again, a single tear slipping down his cheek when Derek hit the base of the plug again. Derek finished off Stiles’ punishment with his hardest blow that made Stiles yell out in shock and have another tear escape.

Derek was quick to remove the now sodden washcloth from between Stiles’ lips and he cupped his lover’s face gently between his palms.

“Color baby, check in with me.” Derek used his thumbs to wipe away the stray tears and tipped Stiles’ flushed face upwards, locking eyes with Stiles whose were half-lidded.

“Green Sir, just give me a moment.” Stiles murmured as he allowed Derek to put his boxers and jeans back into their proper place with just a hiss of displeasure.

“Do you know why I had to do that?” Derek asked as he tugged Stiles into his chest, petting Stiles hair as the younger man clung to him.

“Yes Sir, I understood I broke a rule and I had to be punished. I’m sorry Sir it won’t happen again.” Stiles’ words were muffled by Derek’s shirt but the werewolf heard every single one nonetheless.

“That’s my good boy, okay baby your Dad is almost back, let’s go back to the game hmm?” Derek guided Stiles out of the bathroom and back into the living room.

When John walked back in with the needed beers, he couldn’t help but smile at the sight of Stiles still curled up against Derek’s side but sleeping peacefully with Derek’s arm protectively draped over him. John was glad he had accepted his son and Derek’s relationship; they were good for each other.

Chapter Text

“Are you sure you’re okay with this?” Derek asked Stiles in their afterglow, fingers lightly dragging up and down the younger man’s arm.

“Totally, I mean our schedules don’t always match up and I get that. We both have needs and urges and now that we are together it seems kind of pointless to just jerk one off quietly in the bathroom while the other is asleep. Plus you know I like dripping your cum and god I can’t even imagine waking up already wet and full of your cum.” Stiles explained his reasoning from where he was sprawled out over Derek’s chest, fingers tracing around one of Derek’s nipples.

“Well if you’re sure, then alright.” Derek breathed out, cock valiantly twitching at the image Stiles’ words painted.

“Alright, feel free to mount me whenever you get home and I’m asleep.” Stiles leaned up and kissed Derek’s properly.

“Feel free to do the same, I wouldn’t mind waking up with your pretty lips wrapped around my cock or stained with my drying cum.” Derek rumbled against Stiles' lips earning a whimper.

“I’m too exhausted for another round Derek,” Stiles flopped down onto Derek’s chest, settling there to fall asleep.

It didn’t happen until a week or two after that conversation and Derek stepped into their bedroom to see Stiles fast asleep. Stiles’ was sleeping on his stomach and was wearing nothing but a pair of tight red boxers. It was showcasing his ass and Derek felt his cock jerk in his uniform pants.

Derek stepped up to the foot of their bed and stripped off his clothes, tossing them onto the desk chair until he was naked and his cock was standing proud and erect. Derek crawled onto the bed and tested the waters by parting Stiles legs wider so he could settle between them.

Stiles snuffled against the pillow before falling silent again. Stiles’ breathing was deep and even, his heartbeat was steady in his chest and showed no signs of waking. Derek focused and let one of his claws elongate and he delicately sliced open the back of Stiles’ boxers before letting his human nail reshape. Derek tugged the gape wider until he could clearly see Stiles hole, he pushed his thumb against the wrinkled skin and hummed quietly when it was eagerly swallowed in.

Derek hooked his thumb, rubbing at Stiles inner walls. Stiles let out a quiet noise in his sleep that had Derek pausing before pushing his thumb at Stiles’ rim and watched as it expanded.

Derek grabbed some lube off the side table and quietly slicked his aching cock up. He removed his thumb and straddled his lover’s hips, tugging those perky cheeks apart and he pushed the head of his cock into Stiles relaxed rim. Stiles inhaled quietly in his slumber and Derek exhaled as he watched his cock sink into Stiles ass.

It was a beautiful sight and had Derek getting turned on even more. He leaned forward, smoothing his hand down Stiles' spine before planting his hands on either side of Stiles’ body as he began to roll his hips, shallowly thrusting into Stiles.

Stiles nuzzled his face into his pillow and let out a content sigh as his body reacted to having Derek fucking him like a reflex as his legs parted wider.

Derek smiled pleased at the reaction and began to move a bit faster and bit rougher. Derek was panting as he drove in and out of Stiles’ ass that was bouncing and jiggling with each one of Derek’s thrusts. Stiles slept on uninterrupted, only making soft snuffling noises every so often when Derek’s cock brushed over his prostate.

Derek turned his face into his own arm to muffle his cry of pleasure as his orgasm washed over him. Derek quickly slotted his cock back into Stiles’ ass in order to make sure every drop of his release was emptied into the younger’s ass.

“Love you, Stiles,” Derek whispered as he pecked Stiles cheek before he carefully withdrew from Stiles ass and rolled onto his side of the bed. Derek was pleased with the sight of his cum slowly trickling out of Stiles loosened hole and wrapped his arm over Stiles' waist and tucked his face into Stiles side, inhaling his scent as he fell asleep.

Chapter Text

Stiles sighed contentedly as he raked his fingers through Derek’s hair. The feral Alpha’s head was settled between his thighs, mouth hot and wet on Stiles inner thighs, fangs grazing and nipping at the tender skin.

“You know I have to go back soon… The time for the mating run is almost up, if I don’t show up they’ll send a search party for me.” Stiles said carefully causing Derek to look up at him, eyes still glowing Alpha red. Derek let out a huff of air as he nuzzled Stiles protruding hipbone.

“Don’t… Leave… Me.” Derek gritted out, eyebrows furrowing as he tried to understand what Stiles was saying.

“I don’t want to big guy, but I have to go back home. I’m all my father has left, he lost his mate, my mother when I was young…” Stiles explained, shuddering when Derek dragged his claws over his stomach.

“Mate, stay,” Derek said firmly as he ducked his head down and sucked hard at Stiles right thigh causing the Omega to keen.

“Come with me Alpha,” Stiles suggested as he tugged at Derek’s hair, slick beginning to drip out of his hole when Derek flicked his tongue over the head of his cock. Stiles train of thought was derailed by the Alpha taking his cock fully into his mouth, it was wet and hot and perfect.

“Ohhh!” Stiles moaned, arching up off of the forest floor as he used both hands to grip Derek’s hair. The Alpha pinned his hips down with strong hands as he let Stiles’ cock slide in and out of his mouth, the Omega’s cock was small enough that Derek could take his Omega fully into his mouth without issue.

“Alpha,” Stiles whined breathlessly as Derek swallowed around him and dragged his claws over Stiles' thighs, leaving light red marks in their wake. This added to the mess of darkening marks and bite marks that decorated the Omega’s freckled skin.

“Fuck me,” Stiles panted out, his arousal high with his hole flexing and soaking with slick.

Derek growled at the words and lifted Stiles up so his Omega was straddling his waist. Stiles dug his fingers into Derek’s shoulders, cheeks heating as the feral Alpha’s cock nudged at his hole.

“Alpha,” Stiles whined impatiently as he wiggled against Derek’s erection, aching to have it back inside of him again. Derek ducked his head down, mouth moving over the Omega’s collarbone making sure to leave a line of bruises and bite marks in his wake. Derek lifted Stiles up just enough to push the head of his cock into Stiles’ slick rim.

“Oh fuckkkk,” Stiles moaned out wantonly as the Alpha pulled him down into the V of his lap. Stiles dragged his own claws over Derek’s bare shoulders and upper back as he writhed from his place impaled on the Alpha’s thick cock.

“So… Good, my Omega.” Derek crooned as he sucked a dark mark onto the side of Stiles' neck as he enjoyed the feeling of his Omega tight and hot around him.

“Derek, Alpha, oh fucckkk!” Stiles groaned out as he rocked his hips, mewling as the action shifted Derek’s cock to push against his prostate.

“Good Omega,” Derek praised between grunts as his fingers left bruises on Stiles thin hips as he held his Omega tightly. Derek’s own hips jerking upwards, fucking up into the pretty Omega who was seated on his cock. Stiles babbled nonsensically and raked his fingers over every part of the Alpha he could as he was bounced up and down on Derek’s shaft.

“Mine, my Omega, my mate.” Derek panted as his fangs pressed against Stiles mating gland.

“Yes, yes, please Alpha. Make me yours.” Stiles pleaded, he wanted to be bound to his Alpha, his true mate forever. Derek tangled his fingers in Stiles' hair, pulling the Omega’s head back exposing his throat fully.

Stiles’ eyes flared golden as he screamed out his release the moment Derek’s fangs sank into his mating gland, sealing their bond. On instinct Stiles sank his own fangs into Derek’s own mating gland, claiming the Alpha as his. Stiles whined when h felt Derek’s knot swell up inside of him, locking them together properly.

Derek was making happy noises as he nuzzled and lapped at Stiles' neck, at the mark he had left on him. Stiles was lazily drawing shapes over Derek’s skin, content to stay like this for a while. He would have to leave, but right now he would enjoy the way his Alpha was pumping him full and how their bond sang brightly between them.

“My Alpha,” Stiles said hazily.

“My Omega,” Derek preened as he cupped Stiles' face and kissed him.

Chapter Text

“Are you absolutely sure about this Stiles?” Derek asked as he inspected the red dyed rope he held the coils of rope.

“Yes Sir, I know logically that I won’t wander off anymore but… I want to be sure, I want this Sir.” Stiles wet his lips as he looked up at Derek with wide eyes.

“I’ll take good care of you sweetheart, color system tonight?” Derek rested his palm on Stiles’ cheek tenderly.

“Yes Sir, thank you,” Stiles whispered as he pressed a kiss to Derek’s palm.

“Of course darling now arms straight down behind your back.” Derek settled himself into his proper headspace as Stiles obediently followed Derek’s instructions and exhaled slowly as Derek began to loop and knot the soft rope around his straightened arms until they were tied together in strong, intricate knots that were making sure Stiles couldn’t move his arms.

“Color?” Derek asked as he tested the ropes as he took in the way they laddered up Stiles skinny arms.

“Green Sir,” Stiles said while wiggling his fingers and Derek watched as his whole body relaxed when the rope didn’t so much as shift.

“Easy, easy,” Derek murmured as he lowered Stiles down onto their bed so the younger man was settled on his side. Derek made sure Stiles’ head was on a pillow comfortably before wedging a smaller pillow under Stiles’ wrist that was pressing against the mattress below him. Stiles let out a sigh as he closed his eyes as Derek’s large hands caressed his stomach all the way down to his ankles. The touch was grounding and it settled any nerves that had managed to cling to him from before.

“Your legs are next okay sweetheart?” Derek rumbled softly not wanting to break Stiles out of his descent into his headspace that he so obviously needed.

“Yes Sir,” Stiles whispered and his body slumped as Derek began to loop the rope around his legs, locking them together in the same style his arms were.

“How do you feel now?” Derek asked minutes later when he finished off the last knot of the ropes.

“Green Sir, thank you.” Stiles’ voice began to slightly slur and his eyes were closed and face relaxed. Stiles didn’t even bother to test the strength of the ropes this time.

“You look so beautiful like this, so peaceful.” Derek praised as he rubbed his thumb over Stiles lower lip, his inner wolf content that his mate was here and safe with him and finally relaxed in the knowledge his own body wouldn’t betray him again.

“Sir,” Stiles’ lips parted under the touch of Derek’s thumb and his eyes slit open and Derek inhaled quietly at the sight of Stiles’ hazy eyes.

“You need something else don’t you sweetheart?” Derek picked up on what Stiles was trying to communicate with him. Stiles’ head bobbed slightly and his mouth stayed open in a silent invitation.

“How about you keep me warm with this pretty mouth of yours sweetheart?” Derek’s cock twitched at the idea and his arousal scented the room.

“Yes please Sir,” Stiles’ head bobbed again and his mouth opened wider.

“I’ll take care of you sweetheart, don’t worry and if you need to tap out just lightly bite me, you know I can take it.” Derek chuckled softly as he pulled back from Stiles.

Derek wiggled out of his sweatpants and settled on the bed, moving both of them until Stiles’ head was between his thighs still on the pillow. Derek carded his fingers through Stiles' hair before gently guiding his cock into Stiles waiting mouth.

Derek groaned out while Stiles sighed as Derek’s half hard cock filled his mouth. Derek took a few deep breaths as he willed himself not to get fully hard; he focused on Stiles as he stroked his hair soothingly.

“You’re so good for me Stiles, so amazing and perfect.” Derek crooned and felt Stiles relax even further.

“We’ll stay like this for a while longer,” Derek promised as he reclined against the headboard allowing himself to relax a bit as well. Stiles was safe and tied up between his legs and his mouth warm and soft around his cock. This was all either of them needed for tonight.

Chapter Text

“Do you like my new gloves Alpha?” Stiles asked curiously as he dragged the soft leather covered fingertips down Derek’s cheek to rest on his throat just above his collar.

“Yes Sir, they feel nice on my skin.” Derek murmured as he closed his eyes and enjoyed the feeling of the leather from his place curled up next to Stiles on their bed. He was sore and aching pleasantly as he felt Stiles’ cum slowly trickle out of his ass and down his thighs, cheeks heating up slowly at that sensation. He had already come once that night so he was back in his cage.

“I took my time picking them out for you Alpha, I had to make sure I got the best leather out there,” Stiles said voice tinged with pride as he trailed his fingers back up Derek’s throat and rubbed the leather over Derek’s lips.

“Thank you, Sir,” Derek whimpered out, lips falling apart at the feeling of the leather. Stiles just smiled and pushed his thumb into Derek’s mouth, pressing down on the Alpha’s tongue with just enough strength to make the man keen softly as his cock gave a valiant twitch in its cage.

“So pretty,” Stiles hummed out the words, smile only growing when Derek’s cheeks flushed and he opened his mouth wider. Stiles withdrew his thumb and slowly pushed two of his leather-clad fingers into Derek’s mouth. Derek’s eyes fluttered as the soft leather stroked his tongue and coated his taste buds. Derek absently began to suck on the digits, clenching his ass as he did almost on reflex.

“That’s it Alpha, so good for me.” Stiles murmured as he used his other hand to stroke Derek’s chest, leather rubbing deliciously against Derek’s skin and nipples.

Derek blushed when Stiles removed his fingers and held up the wet leather to show how wet and sloppy Derek had gotten them. Stiles just kissed him as he used his dry hand to pull one of Derek’s legs up over his waist. Derek whined into the kiss when the wet leather fingers sank into his messy hole with ease.

Derek moaned, head falling back when their kiss broke as the leather rubbed against his sensitive walls in firm strokes that had him growing hard in his cage again.

“Sir, oh that feels good.” Derek mewled, breaths coming in short pants now as he rocked back against Stiles' fingers as his body burned with arousal again. Derek moaned and rubbed himself against Stiles body when Stiles added a third finger and rubbed his thumb against his stretched rim.

“I already let you come once tonight Alpha, don’t be greedy,” Stiles warned as he stilled his fingers from their place inside of Derek.

“Y-Yes Sir, I’m sorry.” Derek swallowed as he stilled his body, cock throbbing in its cage uselessly.

“Open,” Stiles said simply and Derek opened his mouth wide. He stuck his tongue out without being told, shuddering when the leather-clad fingers were tugged out of him and he stared at how Stiles white cum had coated the black leather digits.

“Make it up to me,” Stiles said with a smirk on his lips as he placed his cum covered fingers on Derek’s waiting tongue. Derek nodded silently as he closed his lips around his Dom’s fingers and suckled them. He twisted his tongue around the digits, swallowing down Stiles’ cum as he cleaned them.

They repeated this for a while, Stiles scooping his cum out of Derek’s ass with his fingers before watching as Derek cleaned them with his mouth.

Derek’s eyes were hazy and his body pleasantly sore with the taste of Stiles and himself on his tongue as he waited with his mouth open. Instead, Stiles just laid his wet leather gloved hand on Derek’s ass, squeezing gently as he nipped at Derek’s neck.

“Go to sleep Alpha,” Stiles instructed and Derek suddenly felt exhausted and his heavy eyes closed as he cuddled closer to Stiles.

“Good Alpha,” Stiles’ voice crooning was the last thing Derek heard before he fell asleep.

Chapter Text

“You smell odd, is there something wrong?” Derek placed his book down to look at Stiles who had been hovering around the other side of the island in the kitchen. He had been working on some dinner prep while Derek sat on one of the barstools to read and keep him company.

“Well kind of, but not anything bad, at least I don’t think so?” Stiles rambled and Derek smiled, he did love listening to Stiles when he rambled but he also knew a trick to get him to get to the point. Derek slipped off the bar stool and wrapped an arm around Stiles and brought him in for a sound kiss. Stiles all but melted against him and clutched his waist in turn.

“You know you can tell me anything baby, just talk to me,” Derek said quietly, rubbing at Stiles lower lip once their kiss broke and he was pleased that a kiss from him still rendered Stiles to a silent blushing mess.

“I’m trying something, but I don’t know how you will react to it is all…” Stiles worried his lower lip and Derek smiled in spite of himself, Stiles was always worried about him.

“Show me,” Derek let some of his Alpha voice slip into his tone and knew that Stiles even as a human could not resist the order and it helped that Stiles was such a good submissive for him.

“Okay,” Stiles agreed and stepped out of Derek’s grasp, he looked at the floor before meeting Derek’s eyes briefly before he tugged at the strings of his sweatpants and they dropped to the floor around his ankles. Derek felt his mouth go dry and his cock take an interest. Stiles’ was wearing a pair of red lace panties with tiny little black bows that sat on his hipbones. He was obviously enjoying the feeling of them as he was half hard inside of the panties and a small patch of dampness was spreading near the top where the head of his cock was sitting.

“What do you think Sir?” Stiles' voice was shy as he shifted on his feet, fingers curled in the ends of the sleeves of the shirt he had stolen from Derek.

“I think you’re even more beautiful with those on if that is even possible.” Derek praised as he stepped closer and ran his fingertips over the soft fabric and Stiles’ flushed deeply when his cock twitched against the feather-light touch.

“Yeah?” Stiles sounded unsure still and Derek couldn’t have that, he liked it when Stiles was confident and sure.

“Yeah, let me show you.” Derek’s eyes were dark as he gripped Stiles' hips, Stiles yelped when he was suddenly spun around and bent over the edge of the island and Derek was down on his knees behind him.

“So pretty, like a little gift all wrapped up for me.” Derek praised as he cupped Stiles perky ass that somehow looked even better in these red panties. Stiles clung to the edge of the island as he spread his feet wider apart and as blood rushed to his cheeks and down to his cock. Derek reached around and traced the bulge in the lace, as Stiles got turned on further. Stiles moaned prettily when Derek palmed his cock, rubbing the lace against Stiles’ sensitive skin.

“Are these the only pair you have?” Derek asked as he focused and let the claw of his right index finger grow.

“Y-Yes,” Stiles’ voice was hitching as Derek was still palming his cock with his left hand.

“We’ll have to get you some more then,” Derek decided and slit the back of the panties open with his claw before letting it recede and he ripped the back open further to expose Stiles’ hole to him fully.

“Sir!” Stiles’ yelp in surprise at the ripping sound and he knew what had happened. Stiles cry turned into a moan and he pressed his cheek to the cool marble of the island when Derek’s tongue flicked over his hole.

“You’ll look so pretty, all dolled up in red lingerie for me… How would you like if I got you a full set? Would you like to be pretty for me?” Derek purred as he took his time, rubbing his tongue over Stiles hole, relaxing the muscles there.

“Y-Yes Sir, I want to be pretty for you.” Stiles agreed, his cock aching as it strained against the lace panties as Derek inched his tongue into his ass, working him open with that sinful tongue of his. If the panties got him this worked up, Stiles could only imagine what a full set would do. After all if a full set got to Derek more than these panties then it would be worth it.

“Such a good boy for me,” Derek crooned as he cupped Stiles’ ass and spread the cheeks apart before shoving his tongue into Stiles’ twitching hole with gusto, sucking at the rim and twisting his tongue around. Stiles let out something close to a wail at the sensations and pushed back against Derek’s face, feeling the werewolf’s beard rubbing over his skin, he knew he would have beard burn there tomorrow but he didn’t care right now, he needed Derek to hit his prostate instead of just grazing it.

“Please, please, please Sir,” Stiles managed to beg between little cries and he swore he felt Derek smile against his skin but it all faded out when Derek shoved his tongue against his prostate at the same time he ground his heel down against his lace clothed cock. Stiles let out a cry, his whole body arching as cum soaked his panties completely and he slumped against the island, completely boneless and senseless.

Derek took a satisfied look at the red marks on Stiles ass cheeks from his beard and how his hole was open and wet with his saliva. Derek settled the ripped panties back into place the best he could before he rose up and wrapped Stiles up in a hug, kissing at his face and neck.

“So, green for lingerie huh?” Stiles muttered, still dazed.

“Very much so,” Derek nuzzled his mate, pleased he had such an amazing and kinky mate. Stiles’ was perfect.

Chapter Text

“How do I look, Sir?” Stiles asked shyly as he slowly turned in a circle for Derek. His lips were painted a bright red and cheeks already flushed with arousal as Derek stared at him hungrily.

Stiles had a tight red lace bralette, his nipples already hard and sticking out from beneath the thin fabric. His stomach was bare save for a new but familiar pair of panties that clung to his hipbones along with the curve of his cock and balls that were obvious from their place inside of the clingy fabric. Thigh-high stockings were covering Stiles legs and feet, showing off his lean and rather shapely legs and little bows were placed at the top of the stockings.

“Good enough to eat,” Derek said, eyes flashing Alpha red as he obviously licked his lips, as he looked Stiles up and down slowly.

“Isn’t that the idea Sir?” Stiles asked innocently and Derek hooked his finger at Stiles. Stiles swayed his hips as he walked over to where Derek was sitting on the edge of their bed and straddled the werewolf’s lap, wiggling against the older man’s crotch.

“You’re so pretty in this set, with that lipstick on you look like a girl,” Derek admitted as he nosed up the length of Stiles' neck and his lips turned upwards as he detected a spike in arousal, Stiles breathing and heartbeat hitching.

“Do you like that? You want to be my good girl tonight baby?” Derek leaned back; eyes still Alpha red as Stiles wiggled from his place on Derek’s lap. Derek gripped Stiles hips in a warning to stay still, which was obeyed.

“I… I want to be your good girl tonight Sir.” Stiles stammered out, cheeks as bright as the lipstick on his lips.

“That’s what I thought, don’t worry Sir will take good care of you tonight baby girl.” Derek crooned and Stiles whimpered as his arousal spiked higher.

“Now be a good girl for me and let me play with your cute little tits,” Derek ordered as he cupped Stiles chest, rubbing at the erect nipples.

“Yes Sir,” Stiles shuddered, back arching and breath catching in his throat when Derek licked at his right nipple through the lace, doing the same to the left nipple before he tugged the bralette off to the sides to expose Stiles nipples.

Stiles tangled his fingers in Derek’s hair, moaning happily as Derek lavished his nipples. The wolf was licking, sucking and tugging at the little nubs until they were puffy and red from Derek’s mouth and beard.

“Do you like it when Sir plays with your little tits girl?” Derek rumbled when he pulled back from Stiles' chest, grinning at the state Stiles was already in.

“Yes Sir,” Stiles nodded, lips parted wide as he panted for air.

“Well, you should thank Sir properly baby girl. Do you know how my good girl can thank me?” Derek asked as he traced the top of Stiles panties.

“N-No Sir?” Stiles swallowed as Derek let a predatory smile cross his lips as he leaned up to whisper in Stiles’ ear.

“My good girl thanks me from her knees.”

“Oh, yes Sir,” Stiles breathed out, cock twitching from the confines of the panties before he slipped off of Derek’s lap.

Derek leaned back on his hands, watching as Stiles knelt between his legs and unbuckled his pants, obviously eager to get to his cock. That would never change about Stiles, he was always so eager for Derek and Derek loved it. Stiles swallowed when Derek’s cock sprung from his jeans and he wrapped his fingers of his right hand around the girth, giving it a quick pump.

“No, good girls use their mouth and nothing else,” Derek warned and Stiles dropped Derek’s cock quickly before darting a look up at Derek before he leaned forward and those painted lips made a bright red ring around the girth of Derek’s cock as Stiles swallowed him down.

Derek let out a moan, not allowing his eyes to stray from Stiles and his red lips, it was a sight he hadn’t thought he would enjoy but on Stiles, it worked very well. Stiles closed his eyes as he sucked and flicked his tongue over every inch of Derek’s cock that he could reach as he bobbed his head. He moved up and down Derek’s length, sucking hard at the tip and hollowing his cheeks out as he took the wolf’s cock down to the root.

“You’ve got quite the mouth on you baby girl, maybe you aren’t a good girl after all. Maybe you’re a dirty cock slut, is that what you are girl?” Derek didn’t know where this filth was coming from but Stiles seemed to only get turned on further by this if the way he moaned around Derek’s cock and his arousal flared high in his scent was anything to go by.

“I should have known,” Derek cupped the back of Stiles' head to hold him place as he began to thrust into his lover’s mouth and he caught sight of the front of Stiles panties becoming damp.

“Is your pussy getting wet just from me fucking your greedy mouth?” Derek asked and Stiles nodded around Derek’s cock and whimpered when the head of Derek’s cock bumped against the back of his throat.

“Don’t worry slut, I’ll get to your wet cunt soon enough. For now, just remember that cock slut’s always swallow.” Derek reminded with a wolf-like smirk on his lips and that was all the warning Stiles got before his mouth was flooded with Derek’s cum. Stiles’ Adam apple bobbed rapidly as he did his best to swallow down the rush of hot cum, but some spilled out of the corner of his mouth and down his chin.

“Dirty fucking girl,” Derek commented when he pulled his spent cock from between Stiles’ lips and took in the wrecked state of his face and cum staining his chin and painted lips.

“Go on slut, show me that wet pussy of yours,” Derek ordered as he looked down at Stiles whose cock twitched at the order. Stiles scooted back before sitting on his ass, planting his feet on the floor and he tugged his panties to the side to show his pink and wet with lube pucker to Derek.

“You still want to be my good girl don’t you slut?” Derek crooned sweetly.

“Please Sir,” Stiles nodded, eyes wide and cock fully erect in his panties.

“Then work that slutty cunt of yours open for my cock. That’s right I want to see you fuck open your eager pussy on your fingers.” Derek ordered as his cock began to get hard again, thanks to his werewolf abilities.

“Yes Sir,” Stiles whimpered as he reached down between his legs and easily slipped two of his fingers into his hole with a throaty groan. Stiles’ head dropped back as his chest rose up and down as he twisted his wrist and worked his fingers deeper inside of himself. Stiles spread his fingers wider and rocked his hips down against his hand, feeling the dampness on his panties spread further as his body reacted to his fingers brushing over his own prostate.

“Such a slutty girl,” Derek crooned as he stroked his cock, smearing the pre-cum over the tip of his cock as he gazed hungrily down at Stiles trembling body.

“Enough, I don’t want you to make a mess of yourself. That’s my job after all.” Derek grinned as Stiles stilled his fingers and tugged them out of his now slightly gaping hole that began to clench around the empty air greedily.

“Do you know how I want to fuck my dirty girl tonight?” Derek asked as he once again took in the sight of Stiles on the floor below him clad in the red lingerie set.

“No Sir, will you tell me?” Stiles’ tongue flicked some of Derek’s drying cum off his lips as he spoke, eyes hooded and cock straining against the thin fabric of the panties.

“I’m going to fuck you like the little slut you are, on your hands and knees girl.” Derek stood up off the bed; he buckled his jeans and the flush on Stiles' cheeks deepened when Derek just unzipped his fly and tugged his erection free once again. Derek knew Stiles loved being fucked by a fully clothed Derek; he said it made him feel dirty and extremely horny.

“Oh yes please Sir, I love it in this position.” Stiles quickly flipped onto his hands and knees, swaying his hips back at Derek. Derek knelt behind Stiles and swatted Stiles ass in a silent warning before he dug his fingers into the younger man’s hips, snapping the waistband of the panties.

“Such an eager slut aren’t you, I can’t believe I ever thought you were a good girl.” Derek scoffed as he took hold of his cock and dragged it teasingly over Stiles rim.

“I’m sorry Sir, I just can’t help it. I need your big cock so much Sir, I’m desperate for it.” Stiles breathed out, voice hitching over the words as his desperation seeped into his tone. Derek just hummed knowing he should stop tormenting Stiles so he gave his cock one last pump before he snapped his hips forward, sheathing his cock into Stiles’ waiting hole.

Stiles clawed at the floor below his fingers as his back arched as he cried out as he was impaled on Derek’s thick cock, Derek moaned out his pleasure at being inside Stiles’ tight heat once again. He was wet and soft around his cock thanks to the lube and Stiles working himself open on his fingers beforehand.

Derek dug his human nails into Stiles’ hips before he began to roughly thrust in and out of Stiles. The younger man keened and groaned helplessly to the sudden onslaught of sensations that came from Derek pounding into him, hitting against his prostate with each thrust.

“Your pussy is so fucking tight and wet around my cock girl, you fucking love this don’t you? I can tell by how excited your little clitty is getting, do you want me to rub it? Do you want me to fuck your hot little cunt and play with your clit?” Derek breathed into Stiles’ ear as he draped himself over Stiles back, hips still moving rapidly, never letting Stiles have a moment of emptiness.

“Fucccckk, please Sir! Please make me come!” Stiles wailed as he rocked backward to meet Derek’s thrusts, his cock was achingly hard and his balls were painfully tight and heavy from their confines in the lace panties.

“Or maybe I just need to play with your tits again and you will come on my cock like a proper slut.” Derek mused and moved his hands from Stiles' hips and cupped Stiles’ chest from behind, thumb and index fingers pinching the puffy nubs harshly.

Stiles screamed out Derek’s name in surprise as the added sensations of pleasure and pain exploded through him and his cock spurted cum, soaking his panties completely.

“Like a proper slut,” Derek panted as he drove his cock into Stiles tightening hole before his eyes flashed red as he howled out his own completion and flooded Stiles with his cum.

Stiles collapsed onto the floor completely, eyes hazy and large gulps of air were being pulled into his lungs as Derek ground deeper into him, emptying the last bit of his release into Stiles body. Derek kept himself upright and watched as he pulled his spent cock out of Stiles’ now widely gaping hole that was overflowing with the Alpha’s cum.

“Your little pussy is full of my seed now baby girl, you look like a properly bred slut.” Derek praised before he stood his head and scooped Stiles prone form up into his arms and transferred the two of them onto their bed and plastered himself around Stiles in a protective movement.

“How do you feel Stiles?” Derek asked as he tenderly raked his fingers through Stiles' hair and smiled when he scented contentment and his own scent wafting from the man in his arms.

“Amazing, the role play was a bit of a surprise but definitely into it.” Stiles hummed as he turned his head and let out a sigh of happiness as he buried his face into Derek’s neck, his whole body relaxing.

“Definitely into it,” Derek repeated in agreement and let his free hand trace over the now ruined lingerie set that was still clinging tightly to Stiles body and felt Stiles smile against his neck.

Chapter Text

“Come on Derek, faster please!” Stiles begged as he fisted his fingers in the pillow that his head was resting on. His legs were up over Derek’s shoulders and the Deputy was tortuously slowly thrusting in and out of him.

“You’ll take what I give you slut,” Derek said firmly as he inched his cock back into Stiles body. His hole was loose and messy with at least half a bottle of lube; his cock was heavy against his stomach and steadily leaking pre-cum.

“Deputy Hale, please!” Stiles batted his eyes up at his boyfriend and let out a shudder when Derek’s cock grazed at Stiles prostate before he began to move back out of the younger man.

“You want me to fuck you faster? Fuck you harder? Want me to fuck you like the slut you are?” Derek’s voice dropped to a lower tone that had Stiles whimpering.

“Please,” Stiles let out a high-pitched noise when Derek suddenly slammed into him roughly. Stiles arched and dug his heels into Derek’s shoulders, pulling him closer.

“That’s it, fucking take my cock you little slut,” Derek grunted as he began to rapidly thrust into Stiles, heavy balls slapping against Stiles pert ass.

Stiles gasped and keened at the roughness before peering up at Derek in confusion when the man stilled, balls deep inside of him.

“Phone,” Derek said as he snagged his cell from the bedside table that was indeed vibrating and Stiles closed his eyes and decided to enjoy the feeling of being stretched wide open around the Deputy’s cock.

“Hello Sheriff,” Derek said smoothly making Stiles blink up at him in shock. Derek had his phone pressed to his ear and a wolfish grin appearing on his face as he stared down at Stiles with dark eyes.

Stiles smacked his hand over his mouth to muffle a sudden groan when Derek rolled his hips, dragging his cock out of Stiles.

“Yes Sheriff,” Derek said conversationally as he began to thrust into his boss’s son. He kept up the rough pace that he had going moments before and Stiles had to bite his tongue to keep himself quiet. Derek obviously had no issue fucking him senseless while talking with his father on the phone.

Stiles used his free hand to cling to the bed sheets next to him as he lifted his hips to meet Derek’s thrusts, allowing the Deputy deeper into him with each thrust.

“I left it under the file name Project Iris,” Derek said as he pushed himself into Stiles’ sloppy hole, driving into his lover hard each time. Stiles felt his cheeks burn as he heard the sounds of their skin slapping together lewdly and Stiles wondered if his father could hear it from his side of the phone.

“Yes Sir, not a problem at all Sheriff,” Derek said as he used his other hand to reach down and he dragged his fingers over Stiles length. Stiles couldn’t help the cry that escaped from him as he came from the single touch on his cock just as Derek ended the call with his father.

“Naughty little slut, coming while I talk with your father.” Derek scolded with a mocking smirk as he fucked into Stiles, chasing after his own climax.

“Only for you Deputy Hale,” Stiles purred as he clenched up around Derek, eager for him to orgasm as well.

“Damn right,” Derek grunted as he drove into Stiles and with a cry and his eyes flashing bright he came. Stiles mewled pleased as he felt Derek empty his load into his ass and it was so much that he could already begin to drip out of him.

“My own personal slut,” Derek crooned lovingly as he withdrew from Stiles fucked open and messy hole.

“Mm, yes Deputy Hale.” Stiles leaned up for a kiss, which was happily given.

“Want to clean me up?” Derek offered and Stiles eyes all but lit up. Stiles let his legs drop to the bed and made grabby hands at Derek who laughed. Derek shuffled up so he was straddling Stiles' chest.

Derek palmed the back of Stiles head ass he guided his spent and sticky cock into Stiles' mouth. Derek sighed pleased as Stiles began to give his soft cock little kitten licks and soft sucks, making sure to get every inch of Derek’s cock clean of cum.

“So good for me, my own personal slut.” Derek praised as he let his now clean cock slip from Stiles' mouth and Stiles gave him a lopsided smile up at him.

“So knowing I was talking with your dad while I fucked you really got you going huh?” Derek teased as he spooned Stiles from behind, arms protective around the younger man.

“Oh my God, shut up.” Stiles moaned in embarrassment and Derek just ducked his head down and kissed at Stiles freckles with a stupid smile.

Chapter Text

“You know Derek when you first brought this up I had no idea that your slutty boyfriend was actually Stiles, our boss’s son.” Jordan chuckled as he reached down to stroke Stiles hair.

“It just makes it better doesn’t it?” Derek said smugly as he lounged on the other side of the couch, palming himself through his jeans as he watched his boyfriend suck his coworker’s cock happily.

“Little bit,” Jordan admitted before he groaned bucked his hips up making Stiles gag a bit before he adjusted and started bobbing his head.

“That’s enough slut, we don’t want Deputy Parrish to come too soon,” Derek ordered and Stiles obediently let Jordan’s cock pop from his lips. Stiles licked his wet lips and looked up at the two Deputies’ with lust blown eyes.

“Fucking hell,” Jordan swore under his breath that just made Stiles smile like the cat who had gotten the cream.

“Go to the bedroom and ready yourself for us slut,” Derek ordered and chuckled as Stiles all but ran to the master bedroom.

“I figured we both fuck him, he’s been begging me for some DP action recently,” Derek explained as he and Jordan shed the rest of their clothes, leaving them on the couch before following Stiles into the bedroom.

“Sounds good to me,” Jordan agreed as he pumped his cock at the sight of Stiles sprawled on the bed. He was holding his legs at the knees and had them parted wide to show off his wet and loose hole and hard cock resting on his stomach.

“Guests first,” Derek said and Jordan easily slotted himself between Stiles' legs. He took hold of Stiles' legs by the ankles and he held them wider apart. Stiles tossed his arms up over his head and lifted his hips with a moan as Jordan’s cock brushed over his hole.

“Beg for it,” Jordan said huskily and Stiles whimpered at the tone of voice, it never failed to get him going.

“Please Deputy Parrish, I want your fat cock inside of me, fucking me, coming in me, please, please,” Stiles begged as he kept rubbing himself on Jordan’s cock. Stiles’ hole clenching with need each time the head of the Deputy’s cock nudged at it.

“You’ve got a real slut here Derek, you lucky son of a bitch.” Jordan chuckled as he snapped his hips forward, sheathing his whole length into Stiles. Stiles cried out and arched up off the bed, fingers curling into the sheets and his body began to be forced up the mattress as Jordan pounded into him.

“Oh I know he’s quite the cock hungry whore,” Derek said as he slowly stroked himself as he watched his fellow Deputy’s balls slap against his boyfriend’s ass, rim clinging to Jordan’s cock desperately each time he pulled out.

“Fucking tight too,” Jordan grunted as he held Stiles ankles tighter and looked down to watch his cock disappear and reappear from inside of Stiles ass. Stiles was moaning and writhing as he met each of Jordan’s thrusts, his cheeks flushed and drool forming at the corners of his lips as every other thrust brushed over his prostate.

Stiles let out a whine of displeasure when Jordan suddenly pulled out of him completely and tapped the head of his cock against his clenching hole.

“Time for the main event I think, come sit on my cock.” Derek settled at the head of the bed, holding his cock straight up.

“Mm, yes Deputy Hale.” Stiles purred as Jordan released his grip on his ankles and sat back on his heels, gripping his cock tight as he watched.

Stiles shakily straddled Derek’s lap, holding his ass cheeks open giving Jordan a good view of his loose and clenching hole that he had just been fucking a moment ago. Derek held onto Stiles' hips in a familiar motion and guided Stiles down and Jordan tightened his grip on his cock as he watched Derek’s massive cock be greedily swallowed up by Stiles body.

“Ohhh Deputy Hale, I love your thick cock.” Stiles moaned wantonly as he settled himself on Derek’s lap, the Deputy’s balls pressed against his ass. Jordan could see how full Stiles looked and how wide his rim was stretched around Derek’s cock and wondered how they both would fit.

“Gonna open you up some more okay?” Derek rumbled as he nosed up Stiles extended neck.

“Mm, yesss.” Stiles slurred, body jerking when Derek rubbed at his rim and eased his index finger inside of Stiles alongside his cock.

Jordan moved closer, swallowing as he stared entranced at the way Derek slowly added a second finger and Stiles let out a keen as he relaxed and his hole expanded under the pressure.

“Add more lube and you can start entering him,” Derek said as he pumped his fingers and cock in and out of Stiles. Stiles who was clinging to Derek’s shoulders and gasping for breath with each movement.

Jordan spotted the lube and quickly slathered his aching length up with the liquid until it was dripping off onto the bed sheets below as he shifted until he was pressed against Stiles back and hands holding onto Stiles ass cheeks.

Stiles turned his head and gave the Deputy a sloppy kiss that was returned as Jordan rubbed the head of his cock against Stiles stuffed hole. Stiles whined into Jordan’s mouth before their kiss broke as Jordan began to enter him, cock sliding into Stiles alongside Derek’s.

Stiles let out a cry as his body trembled and arched. Jordan grunted in surprise as he watched Stiles’ cock spurt cum over his and Derek’s chest. Stiles collapsed against Derek, panting into his boyfriend’s neck and Jordan easily sheathed the rest of his cock into Stiles now overly stuffed hole.

“Amazing isn’t he, my slut?” Derek crooned as he stroked Stiles hair as he locked eyes with Jordan.

“Understatement,” Jordan panted and began to shallowly thrust into Stiles who keened at the sensation.

Derek grinned as he held Stiles hips tighter and when he felt Jordan push back into him, he lifted Stiles slightly up off of his cock before dropping him back down. Stiles moaned and dug his fingers into Derek’s shoulders and shuddered as the two Deputies kept up that rhythm.

“Do you like having both your father’s Deputies fuck your greedy hole at the same time?” Derek growled out and Stiles’ cheeks burned as he rocked back against the Deputies, loving the stretch of their cocks inside of him and the way they rubbed at him. It was like nothing he had felt before and his mind was emptying.

“Yes, oh fuck yes!” Stiles babbled as he let his head fall back as he was bounced up and down on their cocks.

“Of course you do, such a dirty little cock whore.” Derek smacked Stiles ass as he spoke earning a whimper and a useless clench around their cocks.

“Fuck, gonna come,” Jordan muttered through gritted teeth as he felt his orgasm coil up in his stomach.

“We’re gonna make a mess of you slut, you’re gonna be feeling our cocks and dripping our loads for days.” Derek purred and Stiles’ whole body gave a shudder and his cock a valiant twitch.

“Thought you’d like that, what a dirty slut you are.” Derek chuckled before he grunted when he felt Jordan’s cock pulse next to his own. Jordan let out something close to a roar as he emptied his release into Stiles; prompting Derek to growl and to do the same while Stiles’ shuddered and gasped between them.

Stiles let out a weak noise when Jordan pulled out of him and then he was lifted up off of Derek’s cock before he was laid down on his stomach.

“You did good Stiles,” Derek crooned as he stroked his hair while Jordan couldn’t resist looking.

“Fuck,” Jordan hissed as he parted Stiles’ ass cheeks apart and stared at Stiles’ gaping and cum-drenched hole. They had properly wrecked him and Jordan felt pride flare-up in his gut and he just smiled.

“Really good Stiles,” Jordan agreed and followed Derek’s example and curled up on Stiles’ free side.

“He likes to bask in the feeling for a while, then we’ll get him properly cleaned up,” Derek told Jordan as he petted Stiles hair while Jordan drew patterns over Stiles freckle dotted back.

“Got it,” Jordan murmured slightly sleepy but he was going to stay awake to help Derek clean up Stiles, it was the least he could do after all.

Chapter Text

“I bet you’re confused Alpha,” Stiles said, voice gentle as he cupped Derek’s cheek. The Alpha was kneeling completely naked in the middle of their bed, his usual jockstrap and cock cage were gone and only his collar remained.

“A bit Sir,” Derek pressed into the light touch, eyes flicking down to the bulge in Stiles loose grey sweatpants.

“I know I’m not a werewolf and I can’t give you something I know you’ve been craving,” Stiles explained as Derek’s mind whirred for a moment before his cheeks heated as a memory flashed in his mind. It was one night in their afterglow, curled up together and Derek was dripping Stiles’ come and Stiles’ hand on his stomach as they cuddled.

“Oh,” Derek breathed in realization before curiosity set in.

“I’m not a wolf but I’m going to have you hang off my knot nonetheless,” Stiles promised, eyes glinting as he untied the drawstrings on his sweatpants and let them fall to his ankles. Derek’s cock sprung to full hardness as he stared at what Stiles had between his thighs.

“Go ahead Alpha, feel it.” Stiles breathed out and tugged lightly at Derek’s collar. Derek swallowed as he reached out and curled his fingers around Stiles’ cock and slid his hand down, breathing hitching as his fingers were forced to open wider at the base. The whole thing was already slick and wet with lube.
Stiles had a transparent cock sleeve on, the head was exposed but the base, the base was full and thick and looked just like a knot on a wolf would look like.

“I’m going to knot your greedy ass and breed you full Alpha, just the way you want,” Stiles said when their eyes locked.

“Thank you, Sir, thank you.” Derek rose up higher on his knees and planted a kiss on Stiles' lips in a silent thank you. Stiles cupped the Alpha’s face with his own hands and took control of the kiss; Derek easily fell back onto the mattress as Stiles led them downwards and slotted between his strong thighs.

“Are you ready?” Stiles asked as he sat up, placing Derek’s legs on his hips as he took his cock in hand and nudged the exposed head of his cock against Derek’s entrance.

“Yes Sir, I want your knot so badly.” Derek panted as he clutched at Stiles shoulders, eyes wide and dark with lust.

“I know you do Alpha, you’re just so desperate for it aren’t you?” Stiles crooned as he pushed into Derek in a familiar movement and moaned as Derek opened up for him as per usual. Derek tossed his head back against the pillow below his head and Stiles leaned down to kiss and nip at the exposed skin above and below the collar that claimed Derek as his.

Derek whined in displeasure when Stiles stopped just shy of pushing the knot into him but was soothed by Stiles’ tongue flicking over his nipple just the way he liked it.

“I know Alpha, I know but I have to work you open first.” Stiles rubbed his thumb over Derek’s hipbone as he began to give long, languid thrusts into Derek. Derek sighed as he settled into the familiar, filling rhythm but the larger bulge of the knot bumped against his rim each forward thrust Stiles gave into him.

“More Sir, please I can take it!” Derek pleaded, his patience was about to snap as he clenched around Stiles cock in need.

“If I knew my Alpha was this greedy to be knotted and bred then I would have looked into this far sooner.” Stiles chuckled as he straightened up and lifted Derek’s slightly shaking legs up off his hips and guided them up to Derek’s chest.

“Hold yourself open for me Alpha,” Stiles commanded as he added more lube to his cock and the knotted base of the cock sleeve.

“Yes Sir,” Derek whispered, a shiver making its way over his body as he held his legs up by his shoulders, wide apart so he could still see Stiles.

“That’s a good Alpha,” Stiles crooned as he pushed back into Derek with ease, this time he hooked his thumbs into Derek rim and with one nod from Derek, Stiles began to push the fake knot into him.

Derek let out a cry his body arching and hole clenching. He forced himself to relax as the plastic knot pushed him open wider and wider than ever before. Derek let out a moan when the full size of the knot popped into him and settled against his prostate firmly.

“You took my knot so well Alpha,” Stiles peppered Derek’s face with soft kisses as he stayed still from his place buried deep inside of his mate.

“It feels amazing Sir, I can’t describe it… Thank you, Sir,” Derek felt a bit overwhelmed from the full feeling and the way he and Stiles were locked together.

“Anything for my Alpha,” Stiles said as he shallowly began to thrust into Derek. Derek moaned as his eyes fluttered as the movement only pushed the knot against his prostate.

“I’m close,” Stiles warned and Derek suddenly wrapped his legs around Stiles' waist, both moaning loudly as this action pushed Stiles and his knot deeper into him.

“Come in me Sir, please breed me.” Derek whimpered and gasped when Stiles bit at his neck with surprising force as he emptied his load into Derek, the fake knot keeping the cum inside of Derek.

Derek let out a cry, eyes rolling up into his skull when Stiles’ hand touched his cock and he was spilling his own cum between their stomachs. Derek’s orgasm made him clenched up around the knot and milk all the cum out of Stiles he could get.

“Can we stay like this for a bit Sir?” Derek asked when the two got their senses back and Stiles was leaving mark after mark on his neck and collarbone absently.

“Yes, we can Alpha, after all, we have to make sure I bred you properly. If not I’m afraid we’ll have to keep trying.” Stiles winked as Derek flushed.

“Yes Sir,” Derek said with a pleased smile as he settled down content to stay full of Stiles warm cum and stretched wide in a way that settled something deep in his soul.

Chapter Text

“Are you excited Alpha? It’s your favourite day of the month after all.” Stiles said as he planted kisses over the Alpha’s face.

“Yes Sir,” Derek hummed happily when their lips finally made contact and Stiles fondled his caged cock.

“I have everything set up for us in the other room, are you ready?” Stiles asked as he lightly squeezed the caged cock in his hand, watching as Derek squirmed a bit at the pressure.

“Yes Sir, I’m ready.” Derek’s eyes shone with excitement and Stiles gave him another kiss before releasing his hold on the Alpha’s cock. The two rolled out of their bed and with their hands laced together they walked down the hallway to a locked room only the two of them were allowed into.

“Do you need any help getting situated Alpha?” Stiles asked as he cupped the back of Derek’s neck possessively, loving how the simple touch made Derek all, but melt.

“No Sir,” Derek said after eyeing the waiting machine. Stiles squeezed the back of his neck once before walking over to the machine to finish some last-minute things, allowing Derek to go at his own pace.

Derek took a steadying breath as he propped his leg up on the foot of the bed they had in this room. Derek couldn’t help but whimper when he reached behind himself and tugged the black plug free, his hole automatically clenching at the empty space and he blushed as he felt some of Stiles cum slip out of him.

Derek set the plug down on the bed before sinking to his knees, straddling the waiting machine. Standing straight up and glistening with lube was a thick red dildo, one of their favourites because it was textured and thick. Derek held his own ass cheeks apart and with a deep breath, he lowered himself downwards. He hissed as the dildo glided easily into his cum lick hole before Derek had to wiggle and relax further when the thickest part of the dildo pressed at his rim.

“Fuck,” Derek panted when he was fully seated on the toy attached to the Sybian. The head of the dildo was nudging against his prostate already and his cock was straining against his cage as he adjusted to being full again.

“Good job Alpha, you did wonderfully.” Stiles praised as he caressed Derek’s cheek, rubbing his thumb over Derek’s lips as he spoke.

“Color?” Stiles asked as he held up two small pumps and Derek’s eyes widened at them.

“Green,” Derek breathed out as he pushed out his chest. They had talked about adding suction to his nipples during this but this was the first time they would try it.

“Easy,” Stiles murmured as he set the pumps on Derek’s chest, one over each nipple and he hit a switch on the small machine and Derek let out a gasp as his body jerked. The pumps began to apply suction to his nipples, they felt like they were being pinched and it was just the right amount of pain and pleasure.

“Green Sir,” Derek panted out before Stiles could even ask and was rewarded with a soft kiss.

“Let’s get you out of that cage then Alpha,” Stiles pulled a necklace chain out of from under his shirt and used the key at the end of it to unlock the cage. Derek hissed at the sudden return of blood flow and his cock bobbed from his groin as he became fully erect.

“So full,” Stiles hummed as he cupped the Alpha’s heavy balls, weighing them in his palms making Derek blush.

“We’ll be fixing that won’t we Alpha?” Stiles smiled as he curved his fingers around Derek’s cock, holding him in place as he held up another larger pump in his free hand. This one had two tubes running from the top of the cylinder, one running to a cylinder and the other attached to another machine.

“Color?” Stiles asked once he had the pump settled in the correct place on Derek’s erection.

“Green Sir, I’m ready.” Derek wet his lips and Stiles flipped the switch and Derek saw white. His body arching from his place sitting on the dildo keeping him full and the strong suction on both his cock and nipples had him coming instantly.

“That’s it Alpha, that’s a good boy.” Stiles praised pleased as he watched Derek’s cum drip through the first tube and fall into the waiting cylinder. Derek panted as the suction kept his wet cock hard. Stiles smoothed his hand down Derek’s back and over the swell of the Alpha’s ass before Derek was crying out as another orgasm was pulled out of him when the machine he was sitting on buzzed to life and the dildo attacked his prostate.

“Fuck,” Derek panted when he got his sight back, his head leaning against Stiles' thigh and the younger man’s hand threading through his hair carefully.

“Color?” Stiles asked as he watched intensely.

“G-Green Sir, so intense, but so good.” Derek knew his words were slurring a bit. They had agreed to a month of denial and then at the end of the month, they would have him milked by these machines. It was something Derek wanted and god he adored it every time this day rolled around.

“That’s good to hear Derek, you’re doing so well for me.” Stiles praised in a soft voice as he kept stroking Derek’s hair and Derek nuzzled Stiles thigh in return.

Derek had begun to grind down on the machine, forcing the vibrating dildo to press directly against his sensitive prostate and it was all Derek could do to keep his eyes open as every part of his body was played with.

“How does a higher-level sound Alpha?” Stiles suggested when the machines drew another orgasm out of Derek.

“G-Green Sir,” Derek hummed, eyes closed fully now as his body slumped against Stiles' leg fully.

“That’s my Alpha,” Stiles purred as he hit a few switched and watched as Derek all but screamed and body jolted like he had been shocked as the higher suction on his nipples and cock dragged another weaker orgasm from him.

“Soo goooodd,” Derek slurred against Stiles' thigh as his body rocked on reflex as the pressure on his body kept steady.

“Almost there Alpha, you’re so close to being fully milked,” Stiles promised when he gave the cylinder a glance and saw it was almost full already.

“Want you, want you, Sir.” Derek pleaded in a weak voice as he left open-mouthed kisses to Stiles' thigh, wetting the fabric of his sleep pants.

“How about you give me one more load and I’ll come on your pretty face Alpha. I’ll claim you as mine, how does that sound?” Stiles suggested and smiled when Derek nodded quickly.

Stiles watched as Derek began to bounce himself on the dildo that was vibrating inside of him, eager for his reward and he even flicked the pumps attached to his nipples. Stiles watched amazed as the actions quickly brought out his final orgasm, it was weak and little new cum came out but Derek still moaned and shuddered like it was his first time coming that night.

“That’s my Alpha,” Stiles praised as he eased down the pressure of the pumps on Derek’s nipples and cock before switching off the Sybian completely.

The pumps fell from Derek’s puffy and sore looking nipples while the one around his cock stayed in place but the inside was a mess of white. Derek blinked slowly as he tilted his head back up to look at Stiles and parted his lips wide.

“Greedy thing aren’t you?” Stiles chuckled fondly as he unzipped his pants and took himself in hand. He had been hard for the whole process but was intent on giving Derek all the pleasure that night.

“God, look at you,” Stiles grunted as he began to quickly jerk himself off, keeping his cock aimed at Derek’s flushed and blissful face below him. It wasn’t something he ever would get used to and was proud that he was always the reason it was there nowadays.

“Fuck, Derek!” Stiles exclaimed as his balls drew up tight and he watched with his chest heaving as his cum painted Derek’s face. Staining his flushed skin, getting in his open mouth and in his bread and hair, causing to look utterly debauched.

“Thank you, Sir,” Derek sounded hazy and Stiles swallowed hard.

“Of course Derek,” Stiles murmured and allowed Derek to lean against his thigh again, fingers still in his hair as he allowed Derek time to calm down from the intensity of his milking before the two would begin the proper aftercare but for now they were enjoying the moment fully.

Chapter Text

Stiles hooked his leg over Derek’s waist as the two of them traded lazy kisses under the sheets of their bed, sunlight filtered into the room as it rose in the sky.

“As much as I love this, you know I have that meeting today,” Derek said between kisses and Stiles held back an annoying growl. That stupid Omega woman always flirted and got too close to Derek and it made the Omega in Stiles angry to no end.

“I know Stiles, I hate working with Kate Argent too but it's needed for now.” Derek knew how much Stiles hated Kate Argent, Derek hated her too but he had to make it work.

“You still have time right?” Stiles asked as an idea flared in his mind.

“Some?” Derek raised an eyebrow as he took in the devious glint in Stiles' eyes.

“Good, just enough time for you to eat me out,” Stiles said simply as he rubbed their erections together.

“Fuck,” Derek whispered as his cock twitched as the scent of Stiles slick filled his nose. “Come here,”

Stiles grinned in triumphant as he rose up and straddled Derek’s face, he made sure he was facing out towards the rest of the room as he settled himself against Derek’s mouth.

“Fuck!” Stiles cried as he reached behind him with both hands to grab at the headboard for balance as Derek shoved his tongue into his slick wet hole. Derek grasped Stiles thighs to keep him in place as he worked his tongue deeper into his Omega.

“Yes, yes, oh God, Alpha!” Stiles panted as he began to lift himself up and drop back down onto Derek’s waiting tongue. God, it felt amazing and Stiles just knew his slick was smearing over Derek’s lips and chin, his scent would stick with him for the rest of the day and that should help ward Kate off. That may not be enough though and the ache of his cock brought him another idea.

Stiles reached between his legs and began to jerk himself off as he rode Derek’s face, pleased his Alpha was letting him set the pace. Moans spilled from Stiles' lips as enjoyed the sensations that came from Derek’s tongue in his ass and his own hand on his cock. Stiles arched his back, eyes flying wide open as his cock spurted out ropes of cum that thankfully landed on Derek’s chest and stomach.

Derek gently licked at Stiles clenching and flexing hole, fingers kneading Stiles quivering thighs as Stiles came down from his high.

Derek helped Stiles off his face and curled his Omega close, his own cock was throbbing between his thighs but he was overpowered by Stiles scent that covered both of them.

“You’re going to go to that meeting smelling of me, that should help,” Stiles explained quietly as he purposely rubbed his cum into Derek’s skin and body hair.

“I love you my possessive Omega,” Derek kissed Stiles careless of the slick that was drying on his lips and chin, he had known what Stiles was planning to start with but he didn’t mind it one bit.

“I love you my silly Alpha,” Stiles smiled, pleased that his Alpha was fine with his marking.

“But when I get back I’m going to make you reek of me for days,” Derek promised in a husky voice before dropping one last kiss on Stiles' lips before rolling out of bed to get ready for his meeting.

Stiles’ slick and cum was drying on his skin and kind of sticky, he only brushed his teeth before pulling his clothes on overtop of Stiles release and thought of the shock that would grace Kate Argent’s face and he couldn’t wait to see the realization that she would never get him.

Chapter Text

“Let’s stop here,” Derek eased his bike to a stop in the middle of the trail surrounded by dense trees.

“Why?” Stiles asked tilting her head to the side as she tugged her skirt down, she had no idea why Derek had insisted she wear this short of a skirt when they were going to bike in the forest.

“You’re going to put on a little show for me, after all, you haven’t edged today yet.” Derek lowered his voice as he parked his bike and leaned against the closest tree trunk.

“Here?” Stiles squeaked with her cheeks burning as her pussy throbbed at the mention of edging.

“Here and with that,” Derek’s lips turned up into a smirk as he nodded at the bike seat between her thighs.

“The bike?” Stiles asked her eyes wide as she looked down at the seat.

“I want to watch you fuck yourself on it,” Derek stated and Stiles bit her lower lip as she looked around. Stiles swung herself off the bike seat and then straddled it backward so the narrow part of the seat was inches away from her groin.

“Show me,” Derek ordered and Stiles understood why he had her wear this skirt. She tugged the hem up and pulled her damp panties to the side. Using her left hand she gripped the back of the seat and pulled her crotch closer, whimpering when the leather brushed against her sensitive folds.

“Yeah, like that.” Derek’s voice was full of arousal as he watched with dark eyes as Stiles rocked her hips, letting the edge of the seat rub along her pussy lips, wetting the fabric with her juices.

“Take it like you take my cock,” Derek ordered and Stiles let out a high-pitched keen as she pushed forward, allowing the bike seat to enter her.

“Oh fuck,” Stiles moaned, head falling back as she began to fuck herself on the bike seat, it barely filled her but it still sent sparks of pleasure through her body. She gripped the seat tighter and ground against the leather harder, feeling her climax building up as her natural juices slickened the fabric.

“Enough,” Derek’s voice cut through the haze that had descended on her but she stilled instantly with the bike seat deep inside of her aching pussy.

“Let’s finish our ride,” Derek said as he kicked up the kickstand on his bike and smirked at the wounded noise Stiles made. He watched her pull back from the bike seat, her pussy soaking wet as she settled her panties and skirt back into place. She winced and let out a soft noise as she settled back onto her bike and looked at Derek through her eyelashes.

It took a little while but they finally made it back to Derek’s place and Stiles’ approaching orgasm had disappeared completely. She was still wet and achy but she was used to that sensation by now.

“You looked like something out of porn out there today,” Derek commented once they were inside of his room, his hands cupping her breasts greedily as he nuzzled at her neck while her hands settled on his perfect ass.

“You’re still so wet,” Derek commented as he pushed his hand under her skirt and rubbed his thumb over her damp panties.

“Please Derek,” Stiles whined as she rocked against his thumb needily. Stiles let out a gasp when Derek suddenly spanked her pussy and her legs shook as his teeth dug into the skin of her neck.

“You haven’t finished edging for the day yet,” Derek reminded Stiles as he spanked her pussy again before stepping away.

“Strip,” Derek palmed his crotch as Stiles pulled her shirt up over her head showing her small breasts and pink nipples before letting her skirt and soaked panties drop to the floor around her ankles.

“I want to see you rub your desperate little cunt against that,” Derek kicked down a stool he had brought into the room; the legs were wood and rather thick. Stiles licked her lips as she straddled one of the legs. She flicked her eyes up at Derek as she dragged her pussy along the wooden leg, a moan falling from her mouth at the friction it caused on her aching cunt.

“That’s it,” Derek unzipped his pants, pulling his cock out into the open and Stiles’ eyes locked onto it. Derek stroked himself as he watched as his girlfriend humped the leg of the stool, desperation in her actions as she smeared the leg with her pussy juices.
“You’re close aren’t you?” Derek gripped his cock tightly as he took in the flush and hazy eyes that Stiles was sporting now as she ground her pussy against the wood.

“Yes, oh fuck, please let me come, Derek!” Stiles moaned as she cupped her own breasts, twisting her own nipples in the way she knew Derek liked to see.

“Come over here,” Derek ordered and chuckled as she shifted off of the stool leg eagerly and lay on her back at his feet, holding her own legs apart for him.

“So eager,” Derek mused as he knelt between her spread legs and pushed the head of his cock into her offered pussy. Stiles moaned and clenched around his cock greedily.

“Such a good girl, giving me a hole to come in,” Derek said aloud as he jerked himself off.

“Derek, please, please.” Stiles’ eyes flew open at the realization.

“I never said I would fuck you or let you come, sweetheart,” Derek said as he kept his cock still from where it was inside of her cunt, still working his shaft over.

Derek let out a cry as he orgasmed, emptying his load into her clenching, wet hole. Stiles shuddered at the sensation and the way it slipped out of her pussy when he pulled the head of his cock out of her. She was throbbing and drenched now, she let out a cry when he spanked her pussy again.

“There is always tomorrow,” Derek reminded her as he tucked his cock away.

“Yes Derek,” Stiles murmured as her building orgasm faded back as per normal.

“That’s my good girl,” Derek hummed as he helped her to her feet and kissed her firmly.

Chapter Text

Stiles tossed and turned as he tried to get comfortable on his bed. He was back home without his Alpha, Derek he had to leave behind in the forest when the weekend was up. Everything inside the Omega was aching for his mate, his Alpha. By law he didn’t have to tell anyone who his Alpha was, he only told his father. The Sheriff wasn’t pleased but accepted it and was looking into Derek and figuring out how they can bring the feral Alpha back into town so he and Stiles could be together.

“Alpha,” Stiles muttered into his pillow as his cock twitched and he felt slick beginning to form as he remembered the past weekend with Derek. Stiles sat up, tearing his shirt and pants off so he was lying naked on his bed.

Stiles fumbled around in his bedside table until he pulled out a bottle of lube and his old knotted dildo. It wasn’t as big as Derek but it would have to do until he could be with his Alpha again. Stiles leaned against the wall behind his bed and planted his feet wide as he slicked up a few of his fingers with the lube.

“Ohh,” Stiles moaned as he reached between his legs and sank two of his fingers into his slick and relaxed hole.

“Alpha, Derek,” Stiles whined as he closed his eyes, toes curling into the bed sheets below him as he twisted and hooked his fingers just right. Stiles panted as he curled his free hand around his leaking cock, he thrust himself up into his own fist before dropping his hips back down onto his fingers.

Stiles sobbed as his eyes stung, as it did nothing to quell the flames of arousal that had built up in him. His fingers were too slender and too soft, he ached for his Alpha’s rough, thick fingers that had opened him up many times once Stiles managed to get him to pull back his claws.

Stiles found his prostate and stabbed his fingers against it desperately as he almost painfully jerked himself off. Stiles let out a loud cry when he pulled an orgasm out of himself. Stiles sank back against the wall, panting and head lolling to the side as he shuddered through a rather unsatisfactory orgasm. Stiles never thought he would say that but Derek had blown his mind over and over again so now anything less was disappointing.

“You’re not Derek, but let's hope you work in the meantime,” Stiles muttered as he picked up the dildo, adding coats of lube to the toy. Stiles balanced himself on his knees, facing the wall where he rested his forehead. Stiles let out a slow breath as he pushed the head of the toy against his slick soaked hole and moaned as he pushed the fake cock into himself.

Stiles let out a strangled cry as he pushed the cold, stiff and unyielding dildo into himself fully. It filled him in a way that was different to having Derek inside of him, it would have to do for now. Stiles twisted his wrist around so he had a better grip on the toy and began to rapidly thrust it in and out of himself. He had grown used to the fast and rough thrusts that Derek tended to use and he craved it now, Stiles whined as the bulbous knot brushed over his hot, wet hole each time the Omega pushed the dildo into himself.

Stiles knew he should wait, try to draw it out a bit longer as his cock became fully erect again up against his stomach, but he couldn’t wait any longer. Stiles spread his knees wider and pushed back when he thrust the dildo back into himself. Stiles’ mouth fell open as he keened desperately as he shoved the fake knot into himself. Stiles braced himself on the wall in front of him with both hands as he clenched around the knot to keep it in place.

“Alpha,” Stiles mewled as he rubbed at his puffy nipples, sending sparks over his body before he cupped his small cock and rubbed his thumb over the wet head with just enough pressure.

“Derek!” Stiles cried out as his head fell backward in ecstasy as he pulled another orgasm out of his body, his mating bite on his throat throbbing like a heartbeat.

Stiles panted as he slumped down onto his mattress, legs curled up to his chest as his hole fluttered around the plastic knot. Stiles decided to keep the toy inside of himself as he closed his eyes; it reminded him of Derek, of being full and knotted to his Alpha. Stiles couldn’t wait to see Derek again, to be with his mate.

Chapter Text

“Stiles,” Derek warned lowly as Stiles kissed at his neck, hands groping his chest from behind.

“Please, Sir? I need it so bad,” Stiles whined from his place, Derek. Derek was sitting in his office, trying to get some work done but Stiles was distracting.

“I fucked you on my fingers this morning, how are you still this horny?” Derek asked, swallowing down a moan when Stiles plucked at his nipples through his shirt.

“I’m always horny Sir, you know that,” Stiles said as he ground his hips against the back of Derek’s chair.

“I don’t have time right now Stiles, but if you’re that desperate… I have an idea,” Derek offered and Stiles moved around to face him, his sweatpants tented obviously and eyes alight with arousal.

“Anything Sir, please.” Stiles pleaded as his fingers twitched at his side, but not touching himself.

“As I said, I don’t have time right now but, you can use my foot,” Derek said with a smirk sliding across his lips as he moved his right booted foot forward. Stiles looked down at the shiny leather boot that was covering Derek’s foot and calf.

“Oh, yes Sir,” Stiles wet his lips as he stepped out of his sweatpants and sank down to his knees.

“If you make a mess you have to be a good boy and clean it up.” Derek instructed, “Oh and no hands, it’s my boot or nothing.”

“I understand Sir,” Stiles wet his lips as he settled himself against Derek’s leather boot, shuddering when his cock and balls settled against the warm leather.

Derek hummed at the sight of Stiles naked and straddling his foot before directing his attention back to his laptop, content to let Stiles get himself off. Stiles glanced up and a bolt of lust went through his body when he noticed Derek wasn’t paying any attention to him.

Stiles placed his hands onto the ground behind himself, arching his torso backward and rocked his hips. Stiles gasped at the delicious friction that the leather against his cock and balls caused. Derek was onto something and Stiles rocked his hips again.

Stiles couldn’t help but whimper and he switched positions so he was leaning fully against Derek’s leg, fingers curled around the back of Derek’s jeans. Stiles’ head fell back, mouth parted as he panted and whined as he humped Derek’s booted foot like a bitch in heat.

Stiles rested his forehead against Derek’s knee as his body moved on autopilot. He couldn’t stop, the feeling of the smooth leather rubbing up and down on the underside of his cock and balls was too good, too addicting.

“Sir, Sir!” Stiles chanted under his breath as he felt his balls draw up tight and familiar fingers dug into his hair.

“Come,” A growled word reached his ears and Stiles was gone.

Stiles body arched like an electric current had zapped him. His cock spurted white cum over the black leather of Derek’s boot. Stiles slumped against Derek’s leg, completely out of it and focused on the feeling of Derek’s fingers steadily stroking his hair. A quick glance up showed that he was still focused on his laptop but he was still putting effort into showing Stiles he was right there for him.

Stiles felt a smile appear on his lips before he shuffled back away from Derek’s foot, wincing at the stickiness that covered his groin and he blushed brightly when he saw the mess he had left on Derek’s boot. His blush only deepened when he remembered what Derek had told him about what to do if he made a mess.

Stiles swallowed before he lowered his upper body down and tentatively dragged his tongue through a glob of his own cum. It was an interesting mix of his seed and the leather from Derek’s boot. Stiles blinked as he repeated the action on another part of the boot and softly moaned as the taste exploded on his taste buds.

Stiles felt his cock give a valiant twitch but he was spent, so Stiles let himself relax and float a bit as he dragged his tongue over the leather of the boot. He repeated the action over and over until he only tasted leather, his cum completely cleaned off of Derek’s boot.

Stiles knew he should get back up, but being here at Derek’s feet had something inside of him calm and give off a wave of contentment. Stiles shifted his now tired body until he was on his side and cheek pressed to the damp leather. He closed his eyes and let out a content little sigh.

“That’s my good boy,” Derek murmured and Stiles dozed off with a smile on his cum stained lips.

Chapter Text

“Are you sure about this Stiles, don’t feel pressure just because the others are doing it.” Derek’s voice was low in Stiles’ ear as the two cuddled together on the couch in the lounge area of the conference hall the North American wolf packs were gathered for an annual meeting. It was just the Alpha’s and their mates if they had them.

“I know Sourwolf, trust me I don’t mind. It’s sort of a power play here, showing off their mates and how well they all are together. We are the best together and if this is the way of showing them, then fine.” Stiles hummed back, absently tilting his head to the side in submission to Derek who was kissing and nipping the freckled dotted skin.

Stiles took in the lounge area; some mated pairs were cuddling with a lot of heavy groping involved. Some had their mates kneeling between their legs, some even were sucking their Alpha’s off and even some were fucking in nearby hallways but their noises and scents were known by every wolf in the conference center.

“If you’re sure,” Derek didn’t sound convinced, mainly because he didn’t want to put Stiles on display, his possessive nature kicking in there but it faded when Stiles gripped his knee reassuringly.

“I am, now how about we do it like we did that one rainy night Alpha.” Stiles purred as he easily straddled Derek’s lap, nuzzling Derek’s neck for courage. Derek groped Stiles ass as he allowed his human to scent mark him, Stiles was a little shit and knew exactly what he was doing and Derek trusted Stiles completely.

“That was a good night.” Derek agreed as he shifted his hands around and swiftly unbuckled the front of Stiles’ tight pants and tugged down the zipper. Derek knew the action had caught some of the nearby wolf’s attention. Derek smirked as Stiles let out a little moan when the Alpha shoved his pants and boxers down so they were around his thighs, his cock pressed against the front of Derek’s shirt and his round ass exposed to the room now.

“Such a good mate for me,” Derek crooned lovingly as he gripped Stiles plump rear end and squeezed a bit. Stiles let out a louder moan and shuddered when Derek sank two fingers into him without warning.

“Still so loose and wet from this morning.” Derek hummed his approval as he began to slowly pump his fingers in and out Stiles in the way he knew would have the human squirming and whining within minutes.

“Alpha,” Stiles mewled mainly for show because he only ever calls Derek that in the bedroom is when he wants something or wants Derek to fuck him with his wolf strength.

Stiles looped his arms around Derek’s shoulders and pressed himself closer to his mate, back arching to nicely present the curve of his ass and draw attention to Derek’s fingers that were inside of him. His head was tipped up to showcase the mating bite on his throat; his eyes were closed in bliss. His cheeks were turning a nice shade of pink and his lips were parted wide as he mewled and keened as Derek rubbed at him in all the right ways.

“Nice mate you have there Alpha Hale,” A nearby Alpha commented and others voiced their agreement causing Stiles’ cheeks to burn as he remembered their audience but his cock just leaked a bead of pre-cum in response and Stiles mentally swore as he remembered this was on one of his kink bucket lists.

“He is perfect, my little red.” Derek praised as he kept a steady pace of fingering the squirming human on his lap but soon he was deep in conversation with the nearby Alpha’s. Stiles hot around his fingers and breath hitching in his ear did keep him well aware of how his mate was doing from his place on his lap.

“Looks like the break is over, we better get back in there.” One of the Alpha’s sighed annoyed and Stiles gave a weak whine when Derek slipped his damp fingers out of Stiles’ ass.

“I’ll give you what you want when we finish for the day, okay baby?” Derek cupped Stiles cheeks with his hands, smearing leftover lube and Derek’s own cum over Stiles right cheek.

“Mm, yes Alpha.” Stiles nodded hazy from being so close to his orgasm yet being denied it.

“That’s my mate,” Derek said pleased as he swept Stiles into a kiss, which Stiles melted into. He knew he would be rewarded with a mind-blowing orgasm when the day of meetings was over and he could wait until then. Maybe putting on a show hadn’t been the worst idea in the world and it seemed to put the Alpha’s in a chattier mood with Derek, which was always good for relations in the future.

Chapter Text

Stiles’ was running again, he was just as naked as he was during the mating run but this time it was different. He was running towards his mate through the forest, not caring about the small cuts that littered his skin from branches that caught him as he moved. Stiles was sweating and aching as his heat coursed through his body. He needed Derek; he needed his Alpha before he lost his mind to the heat.

Stiles let out a loud whine when he caught Derek’s scent and veered towards it. It didn’t take long for his Alpha to come into sight and Derek bared his fangs when he caught sight of Stiles. Stiles launched himself at the Alpha, smashing their lips together in a kiss as he wrapped his limbs around his just as naked as his mate.

Stiles melted into the kiss happily, rubbing his body against Derek’s as the Alpha held him up by his thighs and walked him over to the same patch of moss that they had spent their weekend together on. A few wolves milled about, scenting an Omega in heat but when their kiss broke and Derek snarled and flashed his eyes at them they scattered.

“Alpha, please, please. I need you so badly, please Derek!” Stiles babbled as he rubbed his aching cock against Derek’s stomach as the Alpha laid him on the bed of moss.

“Stiles, mate, Omega.” Derek lapped at their mating bite and dragged his hands over every inch of Stiles naked body.

“Breed, want to breed you.” Derek panted out, fully aroused by his mate in heat below him.

“Oh hell, yes, yes!” Stiles’ breath caught in his throat and slick all but gushed out of him at the idea of his Alpha breeding him full. Derek gave a predatory grin at Stiles’ reaction and hooked Stiles trembling legs up over his hips. Stiles locked his ankles together in the small of Derek’s back and wiggled in excitement at finally being with his Alpha again.

Stiles cupped Derek’s shifted face and dragged him down for another kiss as the head of the Alpha’s cock pressed at his slick hole. Stiles moaned into Derek’s mouth as the Alpha shoved his cock into Stiles. Stiles clung to the Alpha, body shaking and hole clenching and fluttering around the real cock that was inside of him.

“So good,” Stiles moaned out, head falling backward when their kiss broke and Derek began to move his hips.

“Derek, Alpha, oh right there!” Stiles cried out when Derek adjusted the angle of his hips and began to hammer against his sensitive prostate. Stiles clawed up and down Derek’s back as he dug his heels into the small of Derek’s back as he pushed up to meet the Alpha’s hard thrusts.

“Mine, my Omega, Stiles.” Derek groaned out as he nipped at Stiles’ mating bite, possessiveness obvious in his action and the way he drove himself deeper into his mate. Stiles rubbed his cock up against Derek’s stomach and cried out weakly as his orgasm was pushed out of him, coating his mate’s stomach with his release.

“Knot me, fuck, fill me Alpha, Derek please!” Stiles begged, basically in tears as the need to be locked to his Alpha overwhelmed him as the heat that had cooled thanks to his recent orgasm roared back to life rather quickly.

Derek howled as he couldn’t help but obey his mate who was in the thralls of his heat and his knot swelled. Stiles sobbed in relief and pleasure as Derek knotted him properly, locking them together and the heat was quelled when he felt the Alpha begin to pump him full of cum.

“I missed you,” Stiles murmured when Derek collapsed on top of him, nuzzling at his neck and face lovingly. Stiles threaded his fingers through Derek’s hair soothingly as the two stayed tied together.

“Me too, missed mate,” Derek said into Stiles' neck, all but purring at being with his mate again.

“Soon we’ll be together properly Alpha, I promise,” Stiles swore when Derek pushed himself up off of Stiles.

“Stiles is… Beautiful,” Derek said slowly and Stiles blushed as he placed his hand on his slowly swelling stomach, the Alpha still flooding him full of cum.

“You’re breeding me, of course, you’ll say that.” Stiles flushed before falling silent when Derek nuzzled their noses together.

“No. Stiles is… Beautiful.” Derek said firmly and Stiles melted again.

“Oh big guy, you’re such a sap.” Stiles pulled Derek back down for another kiss unable to stop himself. Derek kissed back and placed his hand over Stiles' stomach, purring contently at the way it was growing with his cum, properly breeding his Omega mate.

“Love… You.” Derek stated and Stiles beamed up at his mate.

“I love you too Alpha,” Stiles purred back, his heat stated for the time being and contentment filling his heart in a way he never had before.

Chapter Text

Derek crossed his legs as he reclined a bit further in his armchair; the large television displaying the latest football game and Derek was enjoying the peace and quiet of it all.

Derek didn’t take his eyes off the screen as he reached down towards the floor next to his chair and wrapped his fingers around the neck of his beer bottle. He had to wiggle it a bit before it came free of its coaster and he took a swig from it, enjoying the coolness on his throat.

Derek cheered for his team when they made a touch down before settling back down and taking another gulp from his beer. Without looking he lowered the bottle down and wiggled and twisted the base before it sank back into its proper place.

Derek cocked his head to the side when he heard a soft whimpering noise and looked down at the floor next to his chair and couldn’t help but smile at the sight that greeted him.

Stiles had a red ball gag between his lips, keeping them spread apart and thin lines of drool were already dripping down his chin. His nipples were erect nubs on his chest but what Derek focused on next was the way his legs were bent up by his face. His wrists and ankles were cuffed together so Stiles was immobile and his ass was on full display. His cock was hard and forming a little puddle of pre-cum on his caved inward stomach from where his cock was covered in a tight leather sleeve. This was so Stiles didn’t get any ideas about coming while he was like this.

What really made Derek get hard in his pants was Stiles ass. It was coated in copious amounts of lube and Derek’s beer bottle was sticking out of Stiles’ hole. The thickest part of the bottle was deep inside of Stiles, forcing his hole wide and to act as a coaster. Derek flicked his eyes at Stiles’ fingers, which clearly formed his ‘green’ safe movement at his look and Stiles’ eyes were still trained on his own ass, dark with arousal.

Derek couldn’t resist wiggling the beer bottle, chuckling when Stiles rim clenched up around the bottle and Stiles' eyes rolled up into his head with a muffled noise. Derek pushed the bottle in a touch deeper before settling down on his chair, directing his attention to the football game. After all, Stiles was nothing but his beer coaster for that afternoon and he would be treated as such so Derek settled in for his quiet afternoon and to enjoy his beer.

Chapter Text

“You know Professor Stilinski when you first gave me detention I was really angry, but now I’m glad,” Derek smirked as he placed both his hands on either side of Professor Stilinski’s head. Derek had the smaller man pinned to the wall of his office with one of his thighs slotted between the Professors.

“This is highly inappropriate Mr. Hale.” Professor Stilinski stammered out, his cheeks flushed a nice shade of pink while he was pressing himself to the wall behind him, as not to let the student in front of him realize his pants were growing tighter.

“I’ll stop if you tell me to Professor, but I really don’t think you want me to stop.” Derek rubbed his thigh against Professor Stilinski’s groin as he spoke, lips twitching up when the Professor swallowed back a moan.

“Do you Professor Stilinski?” Derek gave a predatory smile when Professor Stilinski looked up at him with dilated pupils and parted lips.

“…No,” Professor Stilinski breathed out, cheeks burning with the realization. Derek tugged at Professor Stilinski’s tie until it came loose in his hand before he looped the strand of fabric around Professor Stilinski’s in a makeshift collar and tugged. Professor Stilinski gasped as he was pulled up off the wall by his own tie and his mouth was taken over by Derek’s. Professor Stilinski scrambled for purchase on Derek’s shirt before his fingers settled on the belt loops of his sinfully tight jeans.

“Even better than I thought,” Derek mused when their kiss broke and Professor Stilinski slumped against his chest, completely out of breath and properly flushed.

“Now be good for me Professor Stilinski and get on your knees.” Derek decided after a moment of thought and how he always daydreamed about those pouty lips.

Professor Stilinski swallowed but sank to his knees in front of his student, the tie going tight around his throat for a moment before Derek loosened his grip on the fabric. Derek used the tie to force Professor Stilinski’s head up so they could lock eyes.

“Let’s put that pretty mouth to use, shall we? Surely you’re better at sucking cock than you are at lecturing.” Derek grinned as he used the tie to pull Professor Stilinski’s face in against the bulge in his jeans. Professor Stilinski gasped as his cheek rubbed along the hard line in the denim.

“Hurry up Professor, you may want to hurry before someone comes by.” Derek reminded his Professor where they were. The Professor nodded and quickly unbuttoned and unzipped Derek’s jeans, inhaling sharply when Derek’s cock sprung free, obviously not expecting the student to have been going commando.

Professor Stilinski swallowed before he wet his lips out of habit before parting them and taking the wet tip of Derek’s cock into his mouth.

“Mm, God that’s so good.” Derek moaned as he dug his fingers into the Professor’s hair as he pushed his hips forward, shoving his length fully into Professor Stilinski’s mouth. The man on his knees gagged at the sudden action before quickly breathing through his nose as he swallowed around Derek’s cock.

Derek looked down and breathed out through his nose loudly at the sight of Professor Stilinski’s head at his groin and those pouty lips stretched wide around his cock. It was like a wet dream and Derek tightened his grip on Professor Stilinski’s hair to ground his senses.

“I’m gonna fuck your mouth now Professor,” Derek warned before angling Professor Stilinski’s head just right and began to drive his hips forward. The Professor gagged a few times to start with before he got used to the rough pace Derek set and just relaxed his jaw and allowed Derek to fuck his mouth, as he wanted.

Derek grunted as he fucked into Professor Stilinski’s wet, warm mouth, loving the way his balls slapped lewdly against the Professor’s chin and how the Professor was basically drooling as he took Derek’s cock into his mouth over and over.

“We can’t leave a mess behind Professor or everyone is going to want to fuck this pretty mouth of yours.” Derek mused as he swallowed a moan down.

“You’re gonna swallow my load when I give it to you aren’t you Professor?” Derek crooned; tugging Professor Stilinski’s head back and dragged the wet head of his cock over Professor Stilinski’s swelling lips.

“Y-Yes,” Professor Stilinski’s tongue flicked over Derek’s leaking slit.

“Very good Professor,” Derek smirked and fed the Professor his cock once more. It only took a few more jerks of his hips and Derek was burying his cock as far back into Professor Stilinski’s as he could go as he moaned out his orgasm.

Professor Stilinski grabbed at Derek’s thighs as he did his best to swallow the sudden flood of warm cum that was being spilled into his mouth. It was hot and filthy and he was aching in his own dress pants as he swallowed his student’s cum.

“Oh that was very good Professor, I think we’ll both be enjoying detention from now on,” Derek smirked, voice breathless as he tucked his spent cock back into his jeans and took in the sight of the Professor at his feet, lips swelling and stained with his cum and the obvious bulge in his pants. It was an arousing sight to be sure.

“I’ll see you next week Professor Stilinski,” Derek said innocently as he grabbed his jacket and left the office.

It wasn’t even a moment after the door shut that it swung back open and Derek was gathering Stiles up in his arms, kissing him soundly.

“God Stiles,” Derek murmured as he peppered Stiles face with kisses making Stiles giggle at the feeling of his bread on his skin.

“Did you enjoy that?” Stiles asked, voice hoarse from taking Derek’s cock.

“So much, god Stiles, I love you so much.” Derek breathed as he rested his forehead against Stiles.

“I love you too, now are you gonna get me off or am I on my own?” Stiles asked, wiggling his eyebrows as he flicked Derek’s ear teasingly.

“Let me return the favor,” Derek said simply before laying Stiles down on the desk. Stiles let his legs fall open and watched Derek with half-lidded eyes as his lover settled between his thighs and slowly unzipped his pants. Derek worked Stiles’ erection out of his pants and boxers before easily swallowing him down.

Stiles used to be embarrassed by how fast he came apart under Derek’s touches but he got over it a while ago. It only took a few firm sucks and a twist of his tongue and Stiles was coming with a cry into Derek’s mouth.

Derek gently suckled Stiles cock, not wanting to over stimulate him before letting Stiles’ fall from his lips and he lifted himself back upright and leaned down to kiss his out of it boyfriend.

“Mm, love you sourwolf,” Stiles murmured as he locked his weak arms and legs around Derek who carefully lifted him up and walked out of the office and towards the bathroom where a bath was sure to be waiting.

“I love you too... Professor Stilinski.” Derek winked making Stiles laugh and blush.

Chapter Text

Stiles wiped his sweating palms on his jeans from where he was sitting on Derek’s bed. He was watching nervously as Derek set a bottle of lube on the sheets next to him before standing in front of him.

“You don’t have to be nervous Stiles, you came to me remember?” Derek said softly as he tilted Stiles chin up so they could make eye contact.

“I know, it’s just… My first time with a guy you know?” Stiles admitted and relaxed when Derek planted a reassuring kiss on his lips.

“I’m glad you came to me instead of bending over for some random guy at a club,” Derek admitted, he looked after those in their frat but Stiles was special to him.

“I wanted it to be you,” Stiles admitted shyly as Derek helped him up onto his feet.

“I’m glad, now let’s get you naked hmm?” Derek hummed as he began to unbutton the front of Stiles shirt. Derek loved the cute blush that spotted Stiles cheeks as Derek pulled his shirt off and fingers began to work on his pants. Stiles let out a soft noise the moment he was fully naked and half hard in front of his crush and head of his Frat.

“Very nice,” Derek hummed as he curled his fingers around Stiles cock and gave it a solid pump, loving the way Stiles' eyes fluttered, head falling back and moaning as he rocked up into Derek’s hand.

“You’re so responsive to me,” Derek praised making Stiles whimper and his hips chased Derek’s hand when the older man pulled away.

“We’ll start off at your own pace okay? How does a blow job sound?” Derek asked as he lowered Stiles down to sit on his bed, tugging at his own belt as he spoke.

“Me or you?” Stiles asked, eyes tracking Derek’s movements and gazing at the bulge that was growing in the crotch of his pants.

“We don’t want to overwhelm you just yet, so how about you suck me off so you can go at your own pace?” Derek suggested as he pulled his cock out of his pants, stroking himself until he was fully erect.

“Y-Yeah that sounds good,” Stiles agreed and Derek hid his smile that he just convinced Stiles to blow him. Derek used his free hand to cup the back of Stiles' head and guided his head forward. Stiles licked his lips nervously before opening his mouth wide enough to let the head of Derek’s cock slip past his lips.

Derek moaned at the moist heat that was slowly engulfing his cock. Stiles let out a surprised moan as the taste of Derek settled on his tongue and he couldn’t stop himself from taking more and more of Derek into his mouth. He only stopped when he gagged around Derek and was pulled back just an inch or so by the hand on his head.

“That’s good Stiles, just take what you can without gagging. Just like that,” Derek crooned as he began to shallowly thrust in and out of Stiles' mouth, pleased with how well Stiles was taking to giving head.

Stiles let Derek set the pace and just focused on relaxing his jaw and the feeling of Derek’s cock sliding over his tongue and the bitter tang of pre-cum that was wet on his tongue. Stiles made a disappointed and confused noise when Derek’s cock was suddenly gone from his mouth and he looked up at Derek with wide eyes.

“We don’t want me to come too soon do we?” Derek had his hand tight around the base of his cock to prevent his orgasm. Stiles felt pride go through him that his mouth alone had brought Derek so close to climaxing.

“No, I guess not?” Stiles’ voice was hoarse and a bit rough that made him blush.

“Now let's get you comfortable,” Derek suggested and guided Stiles back onto the bed further. Stiles happily settled on his stomach and let Derek push soft pillows under his chest and under his hips. Stiles wrapped his arms around the pillow under his chest and rutted his aching cock against the pillow under his hips.

Stiles let out a startled cry when Derek smacked his ass and his head jerked up to see himself in the mirror across from the bed. Stiles saw his flushed face, plumping lips from sucking Derek off and looked halfway to pure pleasure.

“None of that Stiles, we can’t have you trying to get your own pleasure just yet.” Derek scolded.

“Yeah, I’m sorry.” Stiles bit his lower lip as he watched as Derek knelt down behind him, large hands parting Stiles legs wider.

“You’re not going to get naked?” Stiles blurted out before ducking his head away from the mirror.

“Not tonight, this is about you, remember?” Derek cupped Stiles ass cheeks, kneading and groping the soft globes.

“Okay,” Stiles agreed and let out a shaky breath when his ass cheeks were parted wide and cool air brushed over his pucker.

“Now just relax, remember to breath and bare down,” Derek advised as he coated his fingers in lube. Stiles’ body was trembling and Derek placed a calming hand in the small of the younger man’s back and waited until the tremors had stopped before he began to rub his wet fingers over Stiles virgin hole.

“Never had a virgin before,” Derek muttered to himself and distracted Stiles from hearing by pushing his index finger into Stiles hole.

“Ohh! Derek!” Stiles cried out, arching up off the bed at the penetration.

“Relax Stiles,” Derek soothed as he curled his finger and began to pump his finger in and out of Stiles hole. Derek watched as Stiles adjusted and his hole began to slacken and relax. It didn’t take long for Derek to be inserting his second finger into Stiles who moaned loudly and wiggled his ass back against Derek’s fingers.

“Eager aren’t we Stiles?” Derek asked and Stiles let out a soft noise as he nodded in agreement.

“Just wait, this is only prep for what is next to come,” Derek promised as he laid a wet kiss to the slope of Stiles back.

“Please, Derek,” Stiles panted out as he peered over his shoulder, eyes blown wide with lust. It was a good look on him Derek decided.

“Just a bit more, so, so eager.” Derek smiled kindly as he pressed a third finger into Stiles; smile widening as the younger man’s hole swallowed his third finger greedily. Derek pumped them in and out rather roughly before pulling them out and smacking Stiles ass just to watch the flesh bounce a bit and to hear the high-pitched noise Stiles made.

“Now I have one thing I want you to for me, I want you to watch everything in the mirror,” Derek ordered as he slathered his cock in lube with one hand and fisting Stiles hair with his other. Stiles whined in the back of his throat as his head was pulled up and he looked at them in the reflection of the mirror.

Stiles moaned and spread his legs wider and he lifted his ass up to rub against Derek’s cock that he could see reflected in the mirror. Stiles watched as his jaw dropped and eyelashes fluttered as Derek slowly sank into him. Stiles moaned and gasped as he clutched at the bed sheets below him as Derek filled him in a way he had only dreamt about. It was head spinning and only slightly painful before Stiles felt Derek’s balls settle against his ass he knew he was going to become addicted as the pain had been replaced with mind numbing pleasure.

“You feel so good around me Stiles, so damn tight and hot.” Derek praised as he gripped Stiles ass cheeks, pulling them apart to watch his cock slide in and out of Stiles ass. Watching as the rim clung desperately to his cock as he pulled out and spread wide when he pushed back in.

“Derek, Derek, oh fuck, please!” Stiles pleaded as he started pushing back against Derek needily. Stiles cried out when Derek suddenly fisted his hair, yanking his head up and slammed hard into him.

“Damn you look so hot taking my cock. See how happy you look getting fucked. This is where you belong Stiles,” Derek panted in Stiles' ear as he began to rapidly fuck into Stiles who took it happily.

“I love it, please fuck me harder Derek!” Stiles begged as he watched himself being literally fucked into the mattress in the mirror, it was sinful and Stiles loved it.

“So fucking eager for it,” Derek grunted as he reached around Stiles and roughly jerked Stiles off. It wasn’t surprising that Stiles came only after two or three strokes and that caused Stiles to cry out in unfiltered pleasure and squeeze Derek almost painfully tight.

Stiles collapsed limply onto the bed, gasping for air and hips lifted high before they too fell onto the bed when Derek pulled his still hard cock out of him. Derek grunted as he quickly jerked himself off and with his own cry, he came making sure to paint Stiles upturned ass and back with his release.

Derek panted as he grabbed a tissue to clean himself up; he checked the mirror to see Stiles had his eyes closed, looking totally out of it. Derek snagged his phone and silently took a photo of Stiles cum-coated back and ass for personal viewing later on.

“You did so well for being a virgin Stiles, so damn good.” Derek praised once he set his phone down and he laid on the bed next to Stiles who turned his head to look at him. He had a blissful expression on his face and was smiling dopily.

“Thanks, Derek, really I mean it.” Stiles reached out and Derek gave each fingertip a soft kiss.

“Anytime, really Stiles. I don’t mind teaching you everything about sex and then some, only if you want.” Derek offered, not wanting to see Stiles go off with some random guy and instead stay in his bed and be brought pleasure over and over by Derek.

“I’d like that, thank you.” Stiles closed his eyes contently and snuggled closer to Derek who draped his arm around Stiles' waist possessively. Derek’s mind a whir with ideas of what to show Stiles next.