The crunch of familiar branches and leaves under his feet. The well-known smell of old paint on even older wood. The still blinking light bulb on the porch. It’s been a while since he’s last come here in the middle of the night, he’d thought they’d have changed it by now.
The cruiser wasn’t in the driveway. He could take the door. Behave like a functional member of the society. Stiles was awake, if the dim light in his bedroom window was anything to go by, he wouldn’t mind the doorbell too much. Even if it was 1 a.m.
Standing in the middle, looking between the door and the window, Derek pondered which to choose.
Window, for old times’ sake. Even if they were past that already. Hell, he could take the door even if the cruiser was in the driveway. Though maybe not at 1 a.m.
He climbed to the window as stealthily as he could and almost touched the glass to start opening it, when he was forced to stop by the sight that welcomed him.
He couldn’t even blink, his eyes opened wide, almost as wide as his mouth. Logically , he knew Stiles did it. Everyone did it. Especially guys Stiles’ age, college students. It still didn’t stop him from having trouble breathing from shock.
Stiles had a nice cock.
It was long and darker than the rest of him, not that thick, but thick enough to fill Stiles’ hand comfortably. The hand, that was currently moving, up and down, slowly. His thumb circled the head every time it came up. Derek could clearly see the pre-come leaking from the slit.
Fuck . He should go, he should turn back right now and give Stiles the privacy he deserved in this moment of intimacy, but he couldn’t. He couldn’t force himself to look away even for a second, transfixed by the one part of Stiles he’s never had the opportunity to see before.
Even Stiles’ testicles were nice. They were tight, barely even hanging, two perfect little balls that Derek could suddenly imagine both fitting into his mouth at once. He couldn’t stop the small whine that escaped him at the thought. God, what the fuck was wrong with him, he never even thought about Stiles’ cock before, and now he was imagining sucking on his balls.
As if on cue Stiles’ other hand went to fondle them, his back arching slightly the moment he touched them. God, they must be super sensitive. The hand on his cock started moving faster and faster, squeezing from time to time, pumping with all its might, until all of it stopped for barely a second. White liquid started spurting from the tip, covering Stiles’ torso in sticky streaks.
Derek almost came himself at the sight, he didn’t even realize he was hard.
He wanted to break in and lick it all up, taste Stiles’ come, spread it all over Stiles’ torso with his hand and then eat it all up from his chest. Chest that was expanding and contracting visibly from the deep calming breaths Stiles was taking, willing himself to come down from his high.
Not daring to look at Stiles’ face, Derek slunk away slowly, his research needs forgotten. He was never going to forget what he saw that night.
It wasn’t even a full week when Derek found himself going back. He really needed help with research on the faeries. And yes, logically , he could’ve texted Stiles. He could’ve called him. Fuck, he could’ve made an appointment. But for some reason he made his way towards Stiles’ house again.
He could hear it this time, hell, he should’ve heard it the first time as well, Stiles’ wasn’t exactly quiet. He found himself climbing towards the window again, not even considering using the door this time. He was being considerate, Derek told himself. He didn’t want to startle Stiles during his ‘me’ time. And if he also felt a carnal need to see those hands on that perfect cock and perfect balls again then no one needed to know about that. Considerate, that’s what he was.
Except those hands weren’t on the cock and the balls this time. Stiles was on his side, back facing the window, one arm holding his legs to himself, while the other was thrown back, his hand stroking between his cheeks. Lubed up fingers gliding over his asshole. Asshole that was on perfect display.
It was pink, the skin around it the exact same shade of pale as the rest of Stiles’ body. He even had a mole on the inside of his butt cheek. Shit, Derek wanted to kiss that mole, and maybe even that ass too. That small little hole, barely even an opening, so tight. He felt so hot he regretted wearing his leather jacket. Fuck, he regretted wearing anything.
And then the tip of Stiles’ finger stopped over his hole. Derek stopped breathing. Was he going to…? He was, oh, he was. The tip went inside slowly, or maybe it was just a slow-mo-worthy moment of Derek’s life. He held his breath all the way through the finger going deeper and deeper inside. Top knuckle, middle knuckle, all the way to the base knuckle. It was a long finger. Derek breathed out.
Stiles’ ass seemed to clutch at his finger as he moved it in and out, spreading the lube inside himself. Sometimes he would pause with his finger at its deepest and his hand would move in a way that suggested he was moving it in a circle inside himself. God, Derek was not prepared to watch this.
Just when he thought it couldn’t get any worse, Stiles’ withdrew his finger completely and for a millisecond Derek could see the darkness behind his rim, just before it closed up again. Gulping, Derek brushed the sweat of his forehead. Why was he so sweaty.
Still not managing to force his eyes away, to leave Stiles to his private ministrations, he watched as Stiles’s hovered two fingers over his asshole before pushing them in, both at once. The rim stretched accommodatingly, and somewhere in the back of Derek’s head, there was a thought, a persistent one, that-
This wasn’t the first time.
Stiles must have pushed his fingers inside his asshole more than once to do it so expertly, to know what gets him off this well, the circling with one finger, now the scissoring with both. Derek watched as the two fingers stretched the hole even more, giving him a perfect view of Stiles’ insides when the angle was just right . Those fingers that he’s seen in other contexts before, gripping the wheel of his Jeep, toying with pens, touching Derek’s arm through his jacket, when they could’ve been buried deep in Stiles’ ass not even an hour earlier.
This time he registered he was hard. His own cock was straining against the seam of his jeans. It was almost painful, but Derek didn’t dare do anything more than cup himself through the fabric, willing the thing to go down, even though he knew it was hopeless. Not when Stiles was adding a third finger to the mix.
He was still moving them in and out when he abandoned the grip on his legs and rolled to his stomach. He started moving his hips against the sheets, humping his bed with his cock as he shoved the three fingers deep inside his ass. It wasn’t long before his movements became more hectic, aborted, and Stiles was suddenly falling limp onto the bed like an abandoned puppet, spent after his climax, fingers leaving his ass with a squelch that Derek could hear through the window, back moving up and down as Stiles tried to catch his breath.
Derek only wished Stiles turned to his side and spread his cheeks so that he could see how his asshole looked after being so thoroughly fingerfucked.
He wasn’t even thinking about faeries when he creeped towards Stiles’ house the next day. And the day after that. It became sort of a habit. Sue him.
Logically , Stiles should’ve kept his blinds shut. He knew all sorts of creatures lurked in Beacon Hills. So what if Derek was the only one creepy enough to lurk directly outside of Stiles’ window most of the time.
Derek had his fill of all sorts of debauchery that kept going on in Stiles’ bedroom after hours.
Stiles, completely naked, lying casually on his bed, scrolling though some pages on his laptop. All the while having a twinkling red crystal butt plug stuck between his cheeks. Rolling his hips from time to time and letting out a small gasp.
Stiles, pushing not three but four fingers into his ass, this time facing the door, kneeling on his bed with ass high in the air, giving Derek a perfect view of the rim clenching around them. Of the small gape, left for but a second after he withdrew the fingers from his ass.
Stiles, again on all fours, stroking his cock as his butt plug taunted Derek, the crystal covering the rim of his asshole from view, and denying Derek his newest addiction. His only comfort was the mole he could look at. At least this time, when he finished, Stiles took out the plug with his ass still on display. His asshole opened and closed two times before settling down, missing the feeling of being full. Derek decided he liked the plug.
Stiles, trying to push the four fingers further into his ass, to go deeper than the middle knuckle that he has managed so far. Unable to. Not because of his ass not wanting it, but because his arm couldn’t twist enough, because his torso wasn’t flexible enough. He whined on the bed as he tried, fruitlessly, to achieve his goal, while Derek watched, all the while wishing it could be his fingers inside there. He’s be able to get all four of them as deep as Stiles would want them.
Derek felt anxious about the upcoming pack meeting. It was the first time he was going to see Stiles in a normal setting, with his pack mates around and he didn’t know if he’d be able to keep a poker face. What if they could tell, what if his face, or his eyebrows, which Stiles believed to be communicating in their own language, somehow let everyone know what a creeper he was. A voyeuristic pervert. He gulped down a glass of water before setting it back on the table with a little bit too much of a bang.
Isaac looked up at him from the couch. “You alright, man?” he asked, raising his eyebrow with curiosity written all over his face.
“Yeah, just…” thinking about Stiles’ perfectly pink asshole. Constantly. Without a break. “Worried about the faeries.”
Isaac seemed to accept his lie. He wasn’t as good as telling them apart from the truth as Derek. Small mercies.
Within the next minutes other pack members started crowding in through the loft doors and Derek froze at the counter, waiting to see the familiar face. It came at last, covered with moles, honey-brown eyes crinkling at the corners, smiling. He was smiling, at Derek, as their eyes met. He was gorgeous. Fuck, he was so gorgeous. Derek could only watch in stunned silence, as Stiles went on and stumbled onto the couch, more luck than grace, long limbs flailing, fingers grasping at the armrest. Fingers. In ass. Scissoring. Derek shook his head. He couldn’t afford to be distracted.
They had fucking faeries to deal with.
The pack meeting went on as usual, they brainstormed over possible courses of action with whatever scarce knowledge they had. Stiles promised to do research. Research that Derek should’ve asked him to do weeks before. The meeting didn’t last too long since they knew so little, so they started making plans to meet soon, when they knew more.
“How about this Thursday,” Derek proposed, but Stiles started shaking his head.
“Sorry, can’t Thursday, got plans already,” he explained looking directly as Derek, nothing apologetic about his expression.
“And what plans could you possibly have, Stilinski,” Jackson quipped, making Stiles look away. “Not like you’re getting laid.”
He could be , Derek thought immediately. Briefly imagining Stiles impaled on his cock as he rode him to oblivion, before shaking it off and focusing on Stiles answer.
“If you must know I have yoga on Thursdays. I only just signed up, can’t skip the first class,” he replied, rolling his eyes at Jackson, while Derek closed his mouth with a snap.
Logically , there could be a number of reasons for Stiles to suddenly take up yoga. Health, for one. He was human, he had to take care of his health. Or peace of mind, that he so deserved after everything he went through. Many normal, down to earth, completely respectable reasons for taking yoga, Derek told himself, as he tried not to visualise Stiles’ pathetic whimpers as he struggled to stretch enough to fit his hand in his ass.
He needed to leave. Now.
“I gotta go, come up with a date that suits you all and let me know,” he managed saying before bolting out of the door.
He was so screwed.
He should’ve expected Stiles to do his yoga workout naked on his bed at night. He should’ve. It was Stiles after all, it seemed he tended to lose his clothes the moment he entered his bedroom. And logically , he had the right to do so as it was his private space where he shouldn’t worry about creepy perverts watching him through the window.
Derek knew shit about yoga, so he had no names of all the poses that Stiles was doing, but he definitely did like most of them. Especially the one where Stiles stepped off his bed, standing next to it, his back to Derek, and then proceeded to bend forward, his head angling towards his knees. His thighs were close together, his cock pushed back, so it was hanging behind, fully hard and red from the pressure. His pucker was still as pink as ever, but it looked slightly different, looser than the first time Derek saw it. It was barely noticeable, but Derek spent hours cataloguing everything about Stiles’ hole to know that Stiles’ daily ministrations took some toll on it. He wished he could take a picture. He’d be able to masturbate to this image forever, without ever getting bored.
After a moment Stiles’ started straightening out. He didn’t stop when his back was in its original position, instead angling backwards. Derek retreated so fast he almost fell down the small porch roof, before Stiles could see him creeping.
With his daily exercising it wasn’t long before Stiles managed to shove more and more of his hand into his ass. Derek almost salivated the moment he finally put it all inside, down to the very bottom of his purlicue. And then he made a grabbing gesture. His thumb gripping at the top of his asscrack while the rest of his hand must have been doing the same on the inside. Derek was going to die.
While Stiles moved his hand, stroking his internal walls, his cock kept twitching between his legs, leaking so much pre-come it hang like a string from the tip, almost touching the sheets. Suddenly, he withdrew his hand from his ass completely, his gape wide enough for the light to reach inside, enabling Derek to see the pink velvet walls. So inviting. So lickable. God, he would fuck Stiles open with his tongue if he could. He wanted nothing more.
Before he could get more into his rimming fantasy he noticed Stiles squirting more lube onto his fingers, before positioning his hand at his asshole again. But this time he angled his fingers differently. His thumb… it was hidden under his palm, his whole hand shaped like an arrowhead.
Oh dear god. He almost fainted as he watched Stiles push his whole hand inside, all the way down to his wrist. The feeling of fullness so overwhelming, that his cock gave one last twitch before spurting come all over the bedding.
Logically , it made no sense for Derek’s cock to join in the coming-untouched party, yet his boxers were sticky nonetheless as he slunk towards his loft. His own version of a walk of shame.
“How’s your yoga class going?” Kira asked Stiles at the next meeting, making Derek’s ears almost twitch as he tuned in to their conversation.
“Awesome, I feel like a new person already. Also, I am soooo ready to try some new, more advanced poses soon. Downward Dog’s got nothing on me, King Pigeon, here I come!”
“That’s great!’ Kira enthused. “Let me know how that goes.”
“Sure, I’m sure I’ll gloat to some people after I manage to do what I have in mind,” he said cheerfully, before suddenly snapping his head and looking right at Derek.
Derek turned away quickly so that no one could see the vivid red that suddenly seemed to cover his whole body. New poses? What new poses could there be? He paused a little, going back to the way those honey-brown eyes seemed to look right through him. Logically , there was no way for Stiles to read minds, right? Then why the hell did Derek feel like Stiles knew exactly what he was doing.
Nothing could have prepared him for the sight of Stiles on his back, his legs hooked over the headboard of his bed, his cock dangling in front of his face. Mesmerised, he watched as Stiles lifted his head a little, circling his tongue around the head of his pre-come leaking cock. He already looked strained, the skin on his stomach covered with a lot of miniature folds and wrinkles, his back bent so unnaturally, that logically , there was no way in hell he could bend even more to put his cock in his mouth. There was no way.
And yet within a minute Stiles changed his position slightly, unhooking his legs from the headboard and letting his toes hit the bedding over his head. He looked like a fucking contortionist, but Derek couldn’t really focus on the current position of his body when he saw Stiles’ lips close around the head of his own cock. Within seconds he was sucking with enthusiastic abandon, cheeks hollowing as his mouth managed to move even higher up his cock. Or lower. Derek couldn’t deal with perspective right now. Stiles was letting out little hums of pleasure as he blew himself and Derek wondered if sucking someone else would be as pleasurable for him. If sucking Derek off would be.
Imagining those lips around his own cock he couldn’t stop himself and he opened his fly without even registering it. Only when his hand was gripping his own cock underneath his boxer shorts did he realise what he was doing. He was jacking himself off on the porch roof of the sheriff’s house all the while perving at his unaware son. He should be in jail. He should. He’ll even handcuff himself.
Before he could think anymore about himself in handcuffs while Stiles did whatever he pleased to him, he heard a broken moan from the window and he looked back to see Stiles’ cock twitching in his mouth and his throat working in a swallowing motion. He didn’t let even one drop escape. When he stopped coming he let go of his cock with a quiet slurp and licked his lips, looking like a pleased cat.
Derek wanted him to swallow every drop of his come too, not letting even one drop go to waste.
Logically , he knew that was going to come. It was to be expected. Stiles’ asshole seemed so greedy, there was no way in hell it would be satisfied with his fingers and his tiny butt plug alone. Derek knew that, it made sense . And yet he felt completely unprepared when he saw Stiles’ newest addition to the party. The dildo was big . Not unnaturally big or anything, but definitely bigger than what Derek would expect Stiles to start with. Then again, he had his whole hand up there at least once, so maybe Derek was underestimating him a little.
Stiles prepped himself quickly, his hole already used to being filled on regular basis before sticking the dildo on his desk chair. He angled the chair so that the back was facing the door and the front was facing the window and then he positioned himself over it, legs on either side, his chest leaning against the back of the chair. He stuck two of his fingers inside his ass and scissored for a few seconds. After that he used the same hand to lube up the dildo, before lowering himself slowly onto it, his hands spreading his ass cheeks so that the moment the head of the didlo breached his rim was perfectly visible.
Derek’s heart was beating so fast he felt as if it was going to beat its way out of his ribcage any moment. He had never felt anything like this before. The sight of Stiles lowering himself on that fake cock was so erotic and enticing that he almost couldn’t breathe. He’s watched porn before, and yet nothing he’s ever seen got him going like this. Fuck, for the past few years he thought nothing would ever get him going again. Not after… everything.
And yet here was Stiles, only in his early twenties, 147 pounds of pale skin and fragile bone, fucking himself slowly on a dildo, coming almost all the way up and then going down deeper each time. Within a minute it was sheathed all the way inside him and Stiles started gyrating his hips slowly, his arm moving in a pretty obvious way. It took maybe three minutes before his back was bending forward, head resting against the back of his chair, heavy breathing indicating he’s come already.
After a few seconds he started standing up and Derek’s eyes were glued to the dildo being slowly uncovered.
Spread your cheeks, spread your cheeks, spread your cheeks , Derek repeated like a mantra inside his head and surprisingly, Stiles did just that. He gripped both of his mole covered globes between his gorgeous hands - Derek loved those hands - and spread them lightly, just before the dildo finally exited his ass with a squelch. His ass, that was now completely open, pulsating, and dripping lube. Derek wished it was dripping come. His come, more specifically.
The faeries were finally dealt with, and Derek found himself in yet another pack meeting, celebratory this time. Pizza boxes were spread everywhere, and everyone was talking over each other. Relying the more memorable happenings of the fight to boast.
Derek stood quiet in the kitchen. Logically , he knew he should join them, act normal, be their friend, provide praise and whatnot. They all did a really good job, he knew that, but he couldn’t. Not when all he could think about was how Stiles arrived at the scene, baseball bat in hand, ready to take some faeries down, and how Derek all but froze imagining how that baseball bat would look inside his ass. He was a distraction. A distraction that on another occasion might cost them the fight. He couldn’t afford to be this distracted, not when the pack’s lives were at stake. He had to deal with this, but he had no idea how. How do you deal with something like that? He couldn’t just shut Stiles’ out, not when the human did nothing wrong. It was Derek who was wrong here, playing stalker at his window every single night.
“Yooo, Sourwolf,” Stiles’ voice came from behind him, genuinely startling him from his thoughts. He was so distracted he couldn’t even tell the object of his distraction was creeping up behind him.
“What do you want, Stiles?” he gritted through his teeth, trying not to breathe in. He couldn’t afford to smell Stiles right now, when he was so close. He’d get even more addicted to the guy, and he should be doing the exact opposite - he had to stay away.
“What’s got you all broody and stressed, huh? We won. This is a celebration. Ce-le-bra-tion. Happy thing, Derek. Happy thoughts,” he said, his honey eyes twinkling in the light. Derek wanted to grab the back of his neck and smash their faces together. He couldn’t deal with this.
“I am celebrating,” he responded, nodding at the plastic cup he was holding so tight most of his drink ended up on the counter, while the cup remained crumpled in his hand.
“... Right.” Stiles looked at the drink dubiously, before stepping even closer to Derek. “I’m worried, is everything ok?” He asked, before putting his hand on Derek’s shoulder, his fingers lightly digging into Derek’s shoulder through his henley. Fingers. Digging. Shoulder.
He took a deep breath, trying not to lose control of himself. Bad idea. Stiles’ smell went right into his nostrils, his usual honeysuckle and coffee mix, but underneath it there was something more, lube, silicone, ass. Fuck. He noticed some of his betas giving him curious glances. He needed to fucking control himself.
“Fine,” he finally managed to let out. “I’m fine. How’s… yoga?” And what on earth pushed him to ask that question? Did he have absolutely no respect for himself? No mercy?
While he berated himself internally, Stiles’ features did a complete one eighty. Worry was gone from his face, a mischievous smirk taking its place. “Fantastic. I have all my forward bends down to a T,” he said, eyes boring into Derek’s. Forward bends… oh. Stiles, sucking his own cock with enthusiasm flashed before his eyes, and he felt himself grow harder in his jeans. Fuck, he was sporting a semi with all his pack present. At least Stiles couldn’t smell it on him. “Now I just need to work on my stamina, you know. Stretching’s all good, but, ah, it would be even more fun if I could do it longer. I seem to not last as long as other people when I’m doing poses. And yoga’s all about endurance,” he said, winking. He winked. What the fuck? Derek was seeing things, he had to be seeing things.
“That’s really cool. Sorry, but I- I gotta go,” he said suddenly, all but running from his loft once again.
If any of his pack members ever stumbled on a come stained tree in the preserve they’d be able to tell it was him immediately, but he couldn’t even find it in himself to care as he jacked off in the middle of the forest, Stiles’ name on his lips.
Even with shame pouring out of his every pore, he still couldn’t keep himself away from Stiles’ window that night. He was an addict. He needed help, but instead he just let himself fall deeper into his addiction. One day the sheriff was going to find him, handcuff him, and throw him in jail and then he will get his penance. Until then…
Stiles was already fucking himself with the dildo when Derek came. He was lying flat on his stomach, ankles crossed, thighs close together while his hand moved the dildo in an out of his ass as a rather fast pace. His other hand was gripping his sheets, not venturing down to his dick, that was currently hidden within the sheets. He was obviously stopping himself from humping his bed as he worked the dildo deeper and deeper into his ass. Working on endurance , Stiles had said. And then winked. At Derek. Derek still remembered that wink.
Logically , there could be many explanations behind that wink. Stiles got something in his eye. Stiles had a tick. Stiles genuinely liked winking? Maybe in his mind Stiles was saying something funny? And it required a wink at the end? But then, maybe, Stiles winked because he was trying to say something to Derek. Something that Derek couldn’t quite grasp yet.
It still didn’t take that long, but significantly longer than last time, before Stiles couldn’t stop himself from moving his hips at last and coming. His whole body was flushed as he rolled over, sliding the dildo out of his ass in the process. But this time he didn’t immediately drop it. Instead he brought the dildo to his face and sniffed at it minutely, before shrugging his arms in a whatever sort of gesture and putting it right into his mouth.
Derek was having a heart attack. Or at least he was pretty sure he would be having one if he wasn’t a werewolf.
The dildo was thicker than Stiles’ own cock, so his lips stretched around it more than they did when he was sucking himself off. It still fit quite comfortably or at least that’s what Derek’s assumed from watching Stiles fucking his mouth with it. He tried getting it deeper at some point but he immediately gagged and withdrew it, licking at the side before shoving it into his mouth again, careful to not fuck his throat on accident. He was going at it with so much enthusiasm that at least Derek felt his previous question has been answered. Stiles just liked giving head, not only to himself. Which shouldn’t really be surprising considering his oral fixation and tendency to put just about anything within reaching distance into his mouth.
Derek’s cock will one day be within that reaching distance.
A few days later Derek found himself watching as Stiles sat cross-legged on his bed, dressed this time, a box in his hands. He couldn’t quite see what was inside, but he was certain Stiles would unpack it if the look of awe on his face was anything to go by.
Soon, Stiles nimble fingers were tearing the lid from the box and grabbing at whatever was inside with such reverence that Derek was half expecting a Batman action figure made out of pure gold. Logically , it should have been something like that. Siles had no right to look at the big canine cock dildo, complete with a knot at the base, with such devotion. It was doing things to Derek’s head.
Surprisingly, instead of getting right to it, Stiles bent over the other side of his bed and came up with another box. Two dildos? No… This time he didn’t spend as long to open the box, and within minutes he was taking out a bottle filled with something white, a long, thin, transparent tube connected to a spray head, that connected to another tube. What the…?
Stiles jumped off his bed, his treasures in hand and left the room. Derek listened intently and heard the water running in the bathroom. Right, it was a new thing, it had to be cleaned.
Within minutes Stiles was back, putting the dildo, now connected at the base to the tube, on his nightstand. Surprisingly, he took his time undressing. His movements were slow, but deliberate. His fingers lingered on his own skin, gliding across it as he took his shirt off. Derek found himself unzipping his pants again. It was so sensual. He’s seen Stiles’ naked countless times but it was the first time he had to wait for it, to watch his beautiful skin get uncovered inch by inch. Teasing. Tempting. Oh how Derek wished he could be the one doing the undressing.
His cock was now out of his boxer shorts and he was stroking it lazily as he watched Stiles strip with half-lidded eyes. Before long Stiles was kneeling on his bed, fingers working his ass open quickly, the dildo positioned at his hole still connected to the contraption, that Derek only then realised the purpose of.
When Stiles started fucking himself on the dildo Derek felt his mouth go dry. The dildo was deep red in colour, just like a wolf’s cock, and it was sliding in and out of Stiles’ ass with ease. As usual Stiles took time to take it deeper and deeper, still not reaching the knot, which Derek found himself anticipating as he grasped his cock in his hand and pumped it, not even caring that he was doing it where anyone could see him. He just couldn’t stop himself any longer. This was too much. Stiles was slowly killing him. That’s what he was doing.
Stiles played with the dildo more than he usually did, he let it go out completely, before stabbing his asshole with it again. Teasing Derek with his gaping hole, showing him how it gasped open and close at the loss. Sometimes he’d hold his ass open with two fingers and try to wiggle the dildo inside despite the added digits. He was stretching himself that way. Preparing himself. That knot was wider than anything he took so far. Derek could barely take it any longer. If Stiles didn’t shove that toy all the way now, he would not be responsible for his actions.
But Stiles decided to accommodate him, finally. He pushed the dildo inside almost all the way, stopping at the knot, and then he took a deep breath, before applying more pressure. His rim stretched around the silicone, no longer pink but red almost as much as the dildo itself. Stiles stroked at the stretched muscle with his fingers, trying to relax it a little more before giving the dildo one last push, and sheathing it fully inside. Derek yipped at the sight.
Derek was pumping himself faster and faster, when he saw Stiles go for the spray head. He saw him giving the trigger a few pumps. And then a few more. He kept pumping for about thirty seconds, and Derek could see the level of the fluid in the bottle decreasing significantly. Fuck, Stiles was filling himself with so much come it was downright debaucherous. When he was finished, he let out a pleasured sigh and wiggled his butt a little. Slowly, he reached behind himself and took the dildo out, a spray of white liquid following behind it. His hole was clenching once again while the liquid dripped from it, smearing his crack and his thighs with the sticky substance.
Derek was coming at the sight, unable to stop himself, even when he realised he was spurting it all over the sheriff’s roof. For fuck’s sake, he didn’t even have anything to clean it with, not to mention the noise that would be bound to make. He could not let himself be discovered. He hid his cock in his underwear and zipped up his pants as soon as he was done.
In the meantime, Stiles threw the dildo on the covers, the silicone completely covered in white as well, but he didn’t mind. Instead he stayed in this position, airing his ass out, and letting the fake come exit his asshole. Derek couldn’t take it anymore.
He didn’t even know what was going on at the next pack meeting. He knew there was some news about a new maybe-threat approaching, but he really just couldn’t care less. Stiles was sitting opposite of him, splayed all over the couch, half-hanging off the armrest, and he kept looking . Derek wanted to tell him something, tell him to stop, ask him what the hell he was looking at. And logically, he should’ve. But he couldn’t help it if in some twisted way he liked Stiles’ eyes on him. Maybe Stiles appreciated what he saw too. Maybe he even liked Derek, despite all of his fucking baggage and inability to voice any of his thoughts or emotions. Maybe he’d even forgive Derek for watching him in his bedroom, one day…
His phone buzzed in his pocket and he took it out.
Did you like my new toy?
Derek was suddenly attacked by a violent cough. “Derek, man, you alright?” Scott asked and Derek quickly nodded his head, trying to find his breath.
“Wrong hole,” he managed to gasp out, nodding at the bottle of water in his hand. No one commented on the fact that he wasn’t even drinking it.
I bought it for you .
The second text had him staring at his phone, completely frozen, unable to breathe.
The synthetic semen has its perks, but…
I wished it was real come.
Hot, filling me completely, while a real cock was pulsing inside me.
He couldn’t believe what he was seeing. It made no sense. It defied all logic. When he didn’t respond, more texts came his way.
I’m tired of waiting, Derek.
I gave you so many ins already.
It’s been two months.
I’d prefer your come in my ass instead of on my roof.
Was not fun to clean btw. Dad wondered what the fuck I was doing.
Had to make up shit about bird poop.
Derek noticed his hand was shaking, the texts bombarding his phone, reality crashing in. Stiles knew. Stiles knew he was watching and Stiles wanted him despite that. Stiles put on a show for him, specifically. God.
I got myself all ready for you.
Stretched my hole so you can fit without trouble.
Worked on my stamina so I don’t come the minute I have your cock in my ass.
Get it through your thick skull already.
You’ve always been the reason I left my window open at night.
Derek took in a shuddering breath, heart beating wildly in his chest. Always. You’ve always been the reason… Always? They’ve known each other for years, surely…
I want you, Sourwolf.
And I hope I’m not making a giant fool out of myself here…
If you want me too...
Come in tonight.
“Derek, man, are you really alright?” Scott asked again, obvious concern in his voice. “You’re behaving really weird. Got some intel from a mysterious source?” Scott nodded at the phone Derek was still gripping like a lifebuoy. “Are we in danger?”
“No,” he rasped, voice hoarse all of a sudden. “I just got some, personal news.”
Scott looked at him with slight disbelief, because right, what personal news could Derek get. It stung a little, but then Stiles came to the rescue.
“Give him a break Scott. Okay, I think we’re all done discussing the maybe, maybe-not dangerous pixies, I say we wait and see how it unfolds. In the meantime, I believe we can all just leave and give Derek some space, yes? I for one can’t wait to get reacquainted with my bed. It was a helluva day,” he announced standing from the couch and stretching, the hem of his shirt riding up enough to give Derek a glimpse of his pale, delicious skin.
They all started standing up slowly and heading towards the door, while Derek got stuck on thinking about Stiles reacquainting himself with his bed.
Come in tonight , Stiles had said. Derek couldn’t turn down this invitation.
When Derek climbed to the window Stiles was sitting on his bed, fully clothed and looking down at his fingers, twisting them together. He was nervous, Derek realised. He thought Derek wouldn’t come. But Derek was done being oblivious.
He gripped the edge of the window and pulled it up, the noise startling Stiles and making him look up. Honey-brown eyes looking right at Derek.
“You came,” he said, voice light and hopeful.
“I did.” Derek nodded, pushing his fists into the pockets of his jacket, not knowing what the hell to do with them. This was new for him.
“I’m glad.” Stiles smiled, his gorgeous face lighting up even more. It was enough to relax Derek, if only a little.
“How long did you-” He started to ask, but didn’t know how to finish the question. How long did you know I was creeping on you? How long did you know I was a voyeuristic, perverse stalker? None of it sounded too good in his head, but Stiles seemed to get his meaning, even when he couldn’t voice it. As always. But Stiles had always boasted being well-versed in eyebrow.
“Ever since that first time. At least I think it was the first time. Your face was so shocked that it couldn’t have been anything else. I jacked myself off looking at your face. Your eyes were so glued to my cock, you didn’t even look up once. So I got my fill of your jawline. It was the best handy I’ve ever given myself,” Stiles explained, a dreamy look on his face, as if remembering jacking off to Derek watching him.
“The first time?” Derek felt light in the head. He gripped the back of Stiles’ desk chair and slid down against it to sit. He tried not thinking about what Stiles did on this chair once, instead focusing on the matter at hand. Talking to Stiles about this thing , between them. “God, I feel like such a-”
“Derek, don’t,” Stiles stopped him. “I liked it. I wanted it. Fuck, I even changed my usual habits so that everything would be more… on display. I thought you’d realise at some point, but god, you were so fucking oblivious. I nearly opened the goddamn window myself at times.” Stiles moved towards the edge of the bed, closer to Derek, hand grabbed his hand. Long fingers winding around it completely. Those fucking fingers.
“I thought you’d hate me,” he let out a little laugh, filled with shame and self-deprecation.
“And logically , I probably should? But under these circumstances? I loved it, dude. And I would love it if I could stop getting myself off alone, only to the thought of you.”
“You thought of me?”
“Every. Single. Time. I bought a fucking wolf dildo, you doofus. What did you think was going through my head?”
“You do realise that werewolves don’t have a knot…” He said, not really a question. He was stiff with anticipation, with hope that Stiles wouldn’t find that disappointing, that he wasn’t in this only for some fairy-tale fantasy of cocks with knots.
“I do, Jesus. I don’t care, I’ll worship your cock as it is,” Stiles assured with vehemence while standing from the bed. He took a step towards Derek, a lot less sure of himself, before stopping in front of him, Derek’s face level with his stomach, looking down at him. “You’ll let me, right?”
And Derek felt himself deflate, muscles relaxing, finally letting go of any residual anxiety. “I will, fuck. Of course I will. But only if you let me worship yours.”
“I’ll even let you taste my ass. I know how much you want that,” Stiles said with a smile, looking into Derek’s eyes as his hands came up to stroke his stubbled cheeks. He bent down a little, angling Derek’s face up, stopping when their faces were only inches apart. “Can I?” he asked, and Derek could only nod.
Kissing Stiles wasn’t like kissing anyone else before him. He’s only ever kissed women before, most of whom only did it as a means to a nefarious end. Their perfume always kept hurting his nostrils, making them burn on the inside, making it impossible to really focus on the kissing alone. But with Stiles, surrounded by the familiar scent of honeysuckle and coffee as well as the pungent smell of his bedroom that hid no secrets about what exactly was happening in it every night, he felt safe, relaxed and giddy with anticipation for what was to come.
Stiles moved his lips against Derek’s slowly, his fingers massaging Derek’s jawline, stroking up and down with tenderness. Derek responded with lifting his hands to Stiles’ hips and guiding him to sit on his lap. No matter how much yoga Stiles took, bending down like that to kiss couldn’t be comfortable, and Derek’s legs felt too much like jelly to even attempt standing up. Stiles let out an undignified squeak when his ass landed on Derek’s lap, but it wasn’t even a second before he returned to the kissing with more vigour.
He licked at Derek’s lips, coercing him to open them, and when he did, Stiles’ tongue immediately entered his mouth, almost vibrating with excitement at this new place to explore. He was good at it, Derek thought, before allowing himself to get lost in the sensations. He met Stiles’ tongue with equal interest and curiosity as he explored his mouth in turn.
All the while his hands massaged Stiles’ hips, his fingers venturing below the hem of his shirt, to touch the expanse of skin that he’s wanted to touch since the moment he saw it in all its glory. He could fill the little bumps on Stiles’ skin where his moles were, the protrusion on his backbone, the rise and fall of his back as he breathed. Derek needed that shirt off. He broke away from their kiss, ignoring Stiles’ unhappy whine, and rolled up the fabric all the way to his armpits before nudging him to lift up his arms.
Once the shirt was out of the way Derek wasted no way angling Stiles head to the side and putting his nose right on the uncovered skin of his neck clavicle, inhaling deeply before kissing it with open mouth, tongue dragging across it, and all the way over his collarbone. Stiles hands moved into his hair and gripped it tightly before angling Derek’s head back towards his neck.
“That’s it Derek,” he gasped, out of breath. “Scent me and mark me. Let everybody know. I want it. I want them to know,” Stiles babbled feverishly and Derek complied, wondering just how much into exposition Stiles’ was, if he didn’t mind voyeurs outside his window, and then wanted to advertise their new found situation to everyone. He didn’t mind. He wanted everyone to know too. Stiles was taken. Derek wasn’t going to let him go. He sucked on his neck with abandon, kissing and licking over the smooth skin while Stiles kept whimpering above him, grinding his hips up and down on Derek’s hardening cock, still covered by his pants.
Satisfied with the swollen redness his lips left behind Derek moved down to lick and suck at Stiles’ nipple. There was a faint dusting of hair around it, but Derek found he didn’t mind. God, he didn’t mind anything about this situation at all. Except maybe the amount of clothing they had on them.
As if reading his mind, Stiles said “I feel it’s a little unfair that you get to get your fill while I’m being cockblocked by a henley.” He didn’t even wait for Derek to respond before grabbing at the hem and taking it off in a matter of seconds before pausing to appreciate the view. “Dude, I saw you shirtless like a million times, but damn. It never gets old. And now, I can finally tell you. Not waxing? Only like, the best decision ever.” He looked at Derek’s chest hair with almost as much awe as when looking at the wolf dildo, and Derek felt himself puff with pride, pecs tensing at the attention. “Holy fuck, do that again,” Stiles gasped and hovered his hands over Derek’s pecs. “Again,” he whined as he let his hands fall against the muscles to feel them move below them as Derek flexed. “Ungh. Definitely adding pec flexing to my kink list,” Stiles moaned before he leaned down and rubbed his face all over Derek’s hairy chest. “Wanted to do that since the first time I saw it peeking out of your shirt,” Stiles confesses and Derek lets out a little laugh.
“You’re certainly something,” he says, stroking Stiles’ head as he rubs his cheek against his torso. Stiles moved his head up and bit Derek’s nipple as a response. Derek gasped at the feeling, even more blood rushing into his cock.
“You like that, huh?” Stiles smirked, and moved to bite the other nipple.
“Yeah,” Derek breathed out, not able to make his voice chords work.
“I can promise more of that in the future. But now, I want to see my prize,” he said with a wicked smile, before sliding off Derek’s lap to kneel between his legs.
Derek watched him through hooded eyes as Stiles’ fingers worked his pants open. “Lift your glorious butt for me,” he said, urging Derek to move, and quickly sliding both his pants and his underwear down to his ankles. He untied and slid off Derek’s shoes and socks, the rest of his clothes following right after. Completely naked, cock hard and leaning against his stomach, pre-come leaking onto his dark happy trail, Derek waited for Stiles’ next move.
But Stiles was completely transfixed by his cock. Mouth gaping slightly, his teeth not showing, as usual with Stiles, eyes watching with wonder as if he was faced with a miracle. Derek preened under the attention. Finally, Stiles woke from his little trance, put his hand on Derek’s hairy thighs and massaged them, as he leaned forward, breath ghosting over the sensitive skin at the base of his cock, where his balls were hanging. Then, as if he were a wolf himself, he pushed forward, nosing at the skin and inhaling deeply, before letting out a happy sigh. “Mhmm, you smell so good, I just wanna eat you up,” he whispered, but Derek heard it as loud as if he was screaming. His cock twitched at the idea of Stiles eating him up. He’s wanted it for a while.
Before moving to his cock, however, Stiles leaned closer and took one of Derek’s balls into his mouth, sucking on it like it was the sweetest lollipop. Derek couldn’t take it, his hand moved to grab his cock, but Stiles’ slapped it away, moving his fingers from left to right in a ‘no’ gesture.
“Stiles, if you don’t stop I’m going to come before you even touch my cock.” That seemed to get a reaction and Stiles let go of his ball with a pop.
“Oh, no no. That won’t do. No coming anywhere outside me.” And before Derek could even react to that statement, Stiles had his mouth on him, and was sucking all coherent thought out of Derek, through his cock. His lips were stretched deliciously around him, cheeks hollowing just right, while his tongue was working magic on the underside of his cock. His mouth was warm, and wet, and Stiles seemed like he was absolutely loving it, humming happily around Derek’s cock, the vibrations adding more to the experience. One of his hands came up to fondle his balls while the other kept stroking his thigh. The feeling was amazing, easily the best blow job he’s ever had. He could feel his climax building within him. The pleasurable tingling in all his nerves, the added tension to his cock.
“Stiles, I’m gonna-” But Stiles only let out a stronger hum, sucked with more force, and when Derek started to come, swallowed every single drop that hit the roof of his mouth and the back of his throat. And when it was done, he licked his lips, a pleased smile on his face. Just like Derek had imagined. “Fuck, Stiles…”
“Oh we will, don’t worry. But I think you need a minute first, even with your werewolf refractory period. Don’t worry though, I have something for you to eat while we wait.” He smiled again, standing up. “Undress me,” he commanded, standing in front of Derek, tented pants leaving nothing for the imagination. Derek wasted no time getting his fingers on that damned button and pulling the zipper down. He was thankful Stiles wasn’t wearing any shoes and slid the pants down, only to discover Stiles wasn’t wearing any underwear either. “One less piece of fabric to worry about,” he explained at Derek’s questioning glance.
Stepping out of the pants he moved towards the bed and kneeled on it, facing away from Derek. “Come on, Sourwolf.” He beckoned Derek with his finger and bent down, leaning his head against his crossed arms, sticking his ass out into the air. Derek’s nostrils flared as the most intense concentrate of Stiles’ natural scent hit his nose. Fuck, he’s wanted to smell that since the first time he saw Stiles’ asshole through the window.
He moved towards the bed, getting on it on his knees and shuffled towards Stiles’ waiting pucker. Before he could second-guess himself he smashed his face between Stiles’ cheeks and inhaled, revelling in the way it twitched when he breathed out. He kissed Stiles’ asshole softly, but before he abandoned himself into worshiping it properly, he angled his head slightly to the side and kissed the mole that he’s had on his mind for the past two months. Licking over the little bump of skin, he hummed happily, and let his mouth close over it as he sucked.
“Dude, My asshole’s not there, what are you doing,” Stiles whined, wiggling his butt impatiently.
“Just give me a moment,” Derek sighed against the mole, hand coming up to massage Stiles’ ass cheek in order to placate him a little.
“For fuck’s sake Derek, what could possibly be more interesting than my asshole at this moment,” Stiles whined again, but he wasn’t wiggling impatiently anymore, clearly giving in to Derek’s weird wants.
“You have a mole here,” Derek admitted. “It’s been driving me crazy.”
Stiles laughed at that. “Of course I have a mole on my fucking ass. Only me, I swear to god. Also, your mole kink has been noted, just so you know, but please, please , move on. Or I’m gonna die of blue balls.”
“Mhmm, don’t want you to die.” Never did. They had a penchant for saving each other. Always had.
With one last kiss he let go of the mole and went back to Stiles’ waiting asshole. He licked at it fervently, using his hands to spread Stiles’ cheeks apart. It was getting more vibrant in colour under his ministrations but still nowhere near as ready and open as Derek wished it to be. Gathering some spit in his mouth he spat on the hole, watching the semi-transparent liquid cover the little wrinkles and creases before sliding lower over Stiles’ perineum.
“Fuck, that’s hot,” Stiles gasped into the pillow.
It was only going to get more hot, as Derek put his face closer, opened his mouth, ans stuck his tongue out. Spreading Stiles’ cheeks as far apart as he could, he hovered over the hole, until the tip of his tongue was finally at Stiles’ rim. He pushed it in as deep as he could, the taste stronger than ever as his tongue went inside Stiles’ ass. He let it wiggle around a little enjoying the velvety texture around it, before moving his face away. And then moving it back in. He moved his face back and forth with intent, fucking Stiles’ ass with his tongue as Stiles moaned against his pillows with no inhibitions. The sounds he was making went right to Derek’s dick, which was already waking up, ready to participate again. He loved being a werewolf.
Stiles’ hole was red and glistening with spit, but Derek knew that he needed lube if they were going to proceed. Days of watching Stiles’ masturbate ensured he knew exactly where to look for it. He took the bottle from the nightstand and squirted a generous amount on his fingers. He didn’t even bother with one finger, pushing two inside, knowing that his tongue fucking was enough to prep Stiles for them, even though they were thicker than Stiles’. Stiles gasped into the pillow as Derek scissored the fingers inside him, finally enjoying looking at the stretched walls of Stiles’ hole from up close. He added the third finger soon after, knowing that Stiles was well prepared for it. He even admitted it himself. He got ready for Derek.
Deeming Stiles stretched enough, Derek removed his hand and positioned himself at Stiles’ entrance.
“Fuck yeah, I’ve been ready for months. Get on with it already,” Stiles snarked from below. Wiggling his butt again.
Derek couldn’t do anything but comply. He massaged Stiles’ cheeks, spreading them apart again and aimed his dick at Stiles’ hole, positioning the tip against the entrance. He started moving in slowly, only to hear Stiles growl dangerously. And then he pushed his butt back with force, swallowing Derek’s dick completely in one swift movement. Derek had to dig his fingers into Stiles’ hips in order to stop himself from losing balance, or coming. He didn’t want to come just yet.
Stiles was impatient and started moving back and forth on his own, not waiting for Derek, fucking himself on his dick as if he was yet another dildo. While hot as fuck, Derek needed to remind Stiles that this was no dildo. It was real. They were together, fucking, naked, both wanting it and wanting to make the other feel good. He used some force to keep Stiles in place and started moving himself, pushing his thighs against Stiles’, rolling his hips so his dick could explore as much of Stiles’ ass as it could, and hearing his balls slap against Stiles’ perineum with each deep push. All the while he watched his dick disappear into Stiles’ hole, failing to think of anything hotter than that.
“Fuck,” Stiles gasped. “This feels so good, fuck. No dildo, ever, could even compare. Fuck, Derek, fuck my ass. Fuck it. And then come inside me. Come inside my ass, please,” he nearly sobbed and Derek picked up his pace, feeling the tension building again. How was he supposed to last after hearing Stiles basically begging for his come.
He leaned over Stiles back, pressing his chest into it, arms holding Stiles tight against himself for balance, and he moved his hips with uncoordinated force, like a crazed dog mounting a bitch in heat, burying his cock in Stiles ass as deep as possible. Stiles whined, one arm coming up to stroke the dark hair on Derek’s arm as he let himself be plowed from behind.
Feeling himself nearing climax, he reached for Stiles’ cock and started tugging at it, wanting them to come together. It was the first time he touched Stiles’ cock. Hot in his hand, pulsing and ready to spurt. Derek quickened his movements and soon he felt himself releasing inside Stiles, his come colouring his insides white. The feeling of it inside him must have been enough of a trigger for Stiles to start coming too. He kept spurting come into Derek’s hand as Derek rode out his orgasm, breathing heavily against Stiles’ mole covered back.
When he thought he had enough strength not to fall on his face, he straightened himself and slowly pulled his cock out of Stiles’ ass. Enjoying as it squelched and quivered as if calling him to come back, to not leave it open and alone. It gaped open a little, his come flowing out of Stiles’ ass. Before he could think about it, he caught the droplet with his clean hand and pushed it back to Stiles’ hole, wanting to keep his seed inside him.
Stiles finally rolled on his back, and looked at Derek through hooded eyes, looking completely fucked out. His face and chest were flushed, cheeks red from exertion. He smiled at Derek and looked at the hand he was still holding up, completely covered with Stiles come. Derek didn’t really know what to do with it, he couldn’t spot any tissues, and despite everything that usually goes on in that bedroom, he thought wiping it against the sheets was rude.
“Wipe it on your chest,” Stiles said, eyes looking intently at his sticky fingers.
“What?” Derek asked stupidly.
“Wipe it on your chest, do it for me,” he said with more command to his voice, and Derek found himself obeying, wanting to see Stiles’ reaction to it.
He wiped the sticky hand on his chest, come sticking to his chest hair, leaving white gunk all over it. It felt weird, but as he saw Stiles’ eyes go dark at the action, he found himself continuing, almost completely ridding his hand of the spunk.
“Jesus, Derek,” Stiles sighed, pulling himself up and hovering his face over Derek’s chest. “You should be illegal,” he moaned before sticking out his tongue and lapping at Derek’s chest, licking him clean. Derek swore he could feel his dick twitch already. It was one of the hottest things that has ever happened to him. He flexed his pec as he felt Stiles lick over it and he felt Stiles huff out a mirthful breath. “Illegal! I’ll ask my dad if that would be possible. You are a danger to the society’s sanity after all.”
“So are you,” Derek admitted, smiling down at Stiles as he looked up at him.
“You should smile more, fuck. Your smile is like, terrorist level of threat.” He sighed against Derek’s chest and let his arms wind around him. Hugging him. “Cuddle with me.” Not waiting for Derek’s response he angled them to the side and laid them both down. Not that Derek would object to it. They lay facing each other, smiling, Stiles’ hand stroking the side of Derek’s face.
“I’m glad we’re finally on the same page, Derek,” Stiles said, before leaning in and kissing Derek lightly on the lips.
“So am I,” Derek admitted. And he wasn’t lying, even if he only discovered his sexual attraction to Stiles not too long ago, he knew that the affection he felt now, the giddiness inside his chest, they’ve been building up for a long time. He just needed a little incentive to realise what they meant.
“Turn around,” Stiles said, and Derek looked at him in question. “Turn around, I wanna spoon you”
“I’m a big boy Derek, I can be the big spoon.”
“Okay,” he agreed, and turned around slowly. Stiles immediately pressed his chest against his back, arms winding around Derek, knees bumping against the back of his thighs until Derek took the hint and bent his legs as well. Stiles fit against him perfectly, pressed against his whole length, breathing quietly onto his neck, before laying a small kiss at his nape.
Logically , it made no sense to feel this happy, this complete after a single night. To feel like he suddenly had a future with Stiles. Fuck, they haven’t even talked about their relationship status or anything like that yet. But honestly? With Stiles’ arms around him, his quiet, regular breathing indicating he already fell asleep, with his own eyes closing on their own accord, lulled by the sense of security from being hugged like that, all Derek could think was-