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Stiles had had it up to here with Derek Hale’s bullshit.
Yeah, you can’t see how high he was holding his hand up right now, so what? It was still really friggin’ high, like, dislocating-shoulder high. It was as high as his hand could possibly get without actually detaching itself from his body and floating up and away until it reached the moon.
That happening would probably be a better representation of how over it Stiles actually was, though.
So, yeah, Stiles had had it up to there—way up there—with Derek freaking Hale’s ginormous, extra-plush pile of shit. Because Stiles dealt, okay?
Oh . . . did he ever deal.
He dealt with the getting shoved against random surfaces, the embarrassing boners, the complete and utter lack of respect for his privacy, and the thick ass, sexual tension-filled air every time Derek actually managed to meet his gaze. He dealt. With all for it. For years.
He even dealt with Derek ignoring him completely, and running off to fuck the spawn of the dark lord and Freddy Cougar.
Because fucking a minor totally would have been worse than that. Totally.
Yea—no. Nope. Never worse than that. God, Stiles still had nightmares about that chick’s face.
But Stiles dealt, because he’d already managed to get Derek arrested for murder. Twice. And even though Stiles had saved his friggin’ life like, ten times that amount, he didn’t think Derek would be too happy about the Sheriff throwing him in handcuffs a third time. For, y’know, banging his son. Even if Stiles was sure that his dad would only do it to scare him . . . or just to see the look on Derek’s face.
Needless to say, Stiles decided to deal, at least until he was eighteen. Then he expected to be thrown on the bed and ravished by strong, scratchy wolf.
But when the day of his eighteenth birthday rolled around, Stiles found himself painfully unravished . . . by anything.
Especially Derek Hale and Derek Hale’s annoyingly perfect scruff.
Matter of fact, Stiles was pretty sure that Derek was actually hiding from him, because Stiles sure as hell looked. Everywhere. Spent the entirety of his birthday looking, actually.
Well, Stiles was beyond done with dealing.
Forget the fact that Stiles was about to start college . . . Stiles was an emissary in training, and Derek might not get how big of a freaking deal that was, because the first step to learning the art was learning how to keep things a secret, but it was a huge deal. Huge. Emissaries were secret keeping, Jedi mother fuckers who would fuck you up, but didn’t because they were awesome. He knew things. He’d only been training with Deaton for a few months and knew things that Derek’s werewolf brain probably couldn’t even fathom.
Stiles was totally a G.
He was a G who was over it.
Which was why he found himself knocking on the door to Derek’s loft with a pocket full of mountain ash.
--
Derek’s face.
Stiles will never get over the look on Derek’s face when he realized what Stiles was doing.
It was easy, really. Stiles barely even had to lie. He just led Derek straight to the bedroom, distracting him with pointless chatter, like he did best. Derek followed, like an obedient, sexually frustrated puppy. Scowling and pretending not to listen so hard that Stiles could practically hear Derek’s brain working behind him.
Then Stiles turned around, smiled a wide, inviting smile, let himself take in the confused, glaring beauty that his smile turned Derek into for a moment, and then shoved a hand in his pocket.
And Derek’s friggin’ face when Stiles brought the ash filled palm up to his chin and blew was priceless.
Derek didn’t stand a chance, but he tried. He looked cute trying too, Stiles thought, when Derek stumbled backwards in a useless effort to out-run the already forming ring. So cute.
Even when the circle was complete with Derek wolfed out and trapped inside, growling and tearing at his confines, looking at Stiles with an angry, betrayed expression, Stiles couldn’t help but smile.
Derek was just too cute.
“What the hell, Stiles,” Derek barked. Stiles just shook his head, smiling, and sat on the bed Indian style.
--
Talking to Derek about feelings went about as well as Stiles was expecting. Derek was acting completely irritated and unresponsive at first, ignoring him and growling at him whenever he said something especially truthful.
Luckily, Stiles never did anything without a plan B anymore.
Plan B’s were vital to survival . . .
And getting laid, apparently.
--
Stiles nerves spiked when he started to slowly strip out of his clothes, but he forced himself to calm down and stalk the circle around Derek as he let each item flutter to the floor, mindful of the mountain ash that was trapping Derek in. Wouldn’t want to disturb that just yet.
He started with his flannel, then jeans, and ended with his shirt. Stiles noticed that Derek seemed to zero in on his overly puffy nipples before his shirt had even hit the floor. The same two nipples that Stiles had spent the entirety of high school trying to cover up, after the one incident when Jackson saw them in middle school. Stiles had the urge to feel self-conscious all the sudden, to run and hide, to play everything off like some sort of terrible joke.
But then Derek let out a low, lust filled whine, his hazel eyes flashing a bright blue and staying, like he couldn’t pull them away.
Stiles felt better instantly, and a smirk took over his face as he toed off his socks and sat on the edge of the bed. Though, the smirk fell off Stiles’ face when he palmed himself over his briefs, the sight of Derek real and whole in front of him.
Stiles took it slow, made a show of it as much as he knew how to, rubbing long lengths down his cock through the fabric as he watched Derek internally battling with his need to watch. Derek broke after a few long strokes, and his burning blue eyes snapped to where Stiles long fingers were dragging over his own hardness.
Stiles didn’t have time to feel self-conscious, because Derek’s breaths turned rough and heated fast, which encouraged Stiles to slip a hand under his boxers. The movement caused Derek to let out another whine. The noise turned into something that sounded more and more like a moan when Stiles hand wrapped up his own hard cock and gently pulled.
Stiles was getting a little too encouraged, his head tipping back as he stroked, because Derek Hale, even fully clothed, was a bit too much stimulation for a guy like Stiles to handle. He was lost in the zone and the last thing Stiles was expecting was for Derek to speak. But he did.
“You have razor burn,” Derek declared through gritted teeth, and Stiles hadn’t even noticed that Derek wasn’t focused on his cock anymore, and instead was aiming his stare at Stiles chin.
Stiles ceased movement, but didn’t let go of his own hardness. “Um, yeah, big guy, probably because I’m not a child anymore.”
Stiles pointed to his chest for emphasis, “see . . . I’ve even got chest hair.”
The absolute, last thing Stiles was expecting was for Derek to eye the few pathetic, wiry hairs that dusted his chest with a heated passion, but that was what the wolf did, and Stiles nearly lost it then and there.
Stiles laid back against the bed then and spread out. He watched as Derek swallowed, hard, and let his legs fall open even wider. Stiles might have even wiggled his ass around a bit too much, under the pretense of getting comfortable. Derek didn’t look fooled, just hungry in a way Stiles had never seen him.
Stiles took in a deep breath, and gathered up all the courage he’d found that day, he was going to need it for what he was about to do.
Stiles slipped a thumb under the edge of his boxers, and slowly started to push them lower on hips. He couldn’t help the way his heart sped up when his cock finally sprang free and bounced against his stomach with a barely there slap from his leaking precum. After all, that was the first time anyone other than himself had seen Stiles like that. Bare, hard, and ready.
Stiles risked humiliation and eyed Derek the whole time that he slid them off, he wanted to see Derek’s every reaction, and he was glad he did, because that one was his favorite so far. The wolf showed through in more than just glowing eyes as Derek watched him. His nostrils flared wide at the new scent, and Stiles swore he saw a fang poking out, even if it was for just a second.
Stiles found his smirk again when Derek absently took a step forward and hit the edge of the ring, not able to go any further. He started fisting at his own cock again, and thought about what would happen if he let Derek out now. Would the wolf come to him? Or would he find sense and leave?
Well, Stiles couldn’t have that.
He bent one of his knees up, he was trying to give Derek a better view, and from the look Derek wore, Stiles could tell that the wolf really appreciated it. Y’know, in a grumpy kind of way, but Stiles could still tell. He could still see the underlining heat that was in Derek’s gaze.
“I thought,” Stiles started, because he never could shut his mouth. “That you—ah—you didn’t want this, Derek?”
Stiles tried to find a grin when he caught the death glare Derek attempted to send him. The wolf failed. He still looked completely turned on and Stiles wasn’t buying it for a second. However, Stiles was a step past making coherent facial expressions himself, and instead of smiling, he ended up biting his lip to cover up the loud moan that tried to slip out instead of his words.
“Shit—ah—I—shit,” Stiles said, “from where I am it looks like you want it—ahhh—pretty bad, big guy.”
Derek actually growled at Stiles words, but quickly softened again, because the noise only made Stiles hotter, and Derek could tell, Stiles knew he could. Damn werewolf senses. Stiles wasn’t supposed to give away all his kinks on the first go.
Stiles couldn’t stop the moan that time and was already absently pushing his leg up further, fucking into his own fist with some strength. Stiles subtly whispered a spell under his breath and the lube he had stored in his jeans appeared in his free hand.
His strokes barely faltered when he popped the cap open and let a steady stream trail down his dick and onto balls. It wasn’t like Stiles practiced for that moment for years, or anything. But, honestly, he kind of had been.
Stiles started using both of his hands, one still on his dick, the other reaching down and foundling his balls, the lube warming up and spreading around.
Stiles gave his dick an almost painful squeeze when he realized how close he actually was, and then let it go completely. His cock fell heavy against his stomach, and Stiles never took his eyes off Derek as he did it. Realization spread over Derek’s features, and he clawed at the barrier when Stiles used both of his hands to spread his own legs wider, his cheeks further apart. Stiles kept watching Derek the whole time as he started playing with his own hole, not wanting to miss a thing that flashed over the wolf’s face. Derek growled long and possessively when Stiles finally pressed a finger in.
It seemed as if Derek was in the same boat as Stiles was, not wanting to miss a thing, his eyes were glued to the sight if Stiles fucking himself with his own finger. Stiles lost all prowess as he added another finger, but if Derek’s moan was anything to go by, then Derek thought he looked even better so debauched.
Stiles lifted his hips and started scissoring himself open with a slew of profanities. Stiles wasn’t even touching his dick, but he knew he wasn’t going to last much longer either way, so he grabbed up his cock again, and whispered under his breath, “I’ve thought about this for—ah—for years, Derek. You fucking me. Opening me up—ah god—I need you.”
Stiles was past the point of making sense of Derek’s reaction, but he knew Derek had heard every word of it.
Not two seconds later, Stiles was crying out as he came, painting his own belly with stripes of seed. Derek moaned loud and long as he took in the new scent. Stiles listened, stroking himself until he was a twitching mess, then opened his eyes from where they’d pinched shut to look at Derek with hooded lids.
The room was silent besides their breathing, but neither one of them looked away.
Eventually Stiles sat up, he was suddenly uncertain of what to do, because if he let Derek out now, and the wolf still ran away, or told Stiles to leave, he didn’t think he could handle it.
“Do you get it now?” Stiles asked.
Derek nodded, but didn’t explain further, and Stiles’ gut twisted.
Stiles scooted to the end of the bed and toed at the mountain ash. He couldn’t look as he did it, Stiles wanted to give Derek a choice now, but he couldn’t watch if Derek didn’t choose him.
Stiles nerves were short-lived, though, because as soon as the ash broke, Derek was leaping over and pressing Stiles flat against the bed.
And finally, finally, Stiles knew what it was like to get nuzzled by that warm, scratchy face.
Derek pulled back, and looked Stiles in the eye, serious. “Can I kiss you?”
Stiles snorted. It was probably very unattractive, but Stiles didn’t give Derek a chance to so much as raise an eyebrow before he was crashing their lips together.
Derek’s clothes were getting stained by the cum on Stiles’ stomach, but he didn’t seem to care. It certainly didn’t stop the wolf from cocooning Stiles in his strong limbs and rubbing their bodies together at every angle. Stiles shivered when Derek’s hips snapped forward, the hard line of his cock rutting against Stiles’ leg.
Derek suddenly stopped and pulled away, but before Stiles could say anything, the wolf was shuffling down Stiles body to lick at the smeared lines of cum on his belly. Stiles moaned, and then groaned, and then moaned again.
He had never seen anything so fucking hot, and Derek’s tongue was insanely warm and soft against his skin, licking delicate patterns until Stiles wasn’t as sticky, just slick with Derek’s spit. Stiles was more turned on than he’d ever been in his whole life, but his spent dick didn’t seem to get with the program until Derek started lapping at his nipples.
Derek licked, then sucked, even gave each one a small bite, and Stiles couldn’t help but preen under the attention, his cock twitching with interest again.
Derek felt the movement and stilled, mouth going slack over Stiles’ chest for a few seconds before he looked up at Stiles with a raised brow, then down at Stiles’ growing length, then back up to Stiles’ face again.
He was smirking. The bastard.
Stiles didn’t have time to comment, because Derek flipped him over like he weighed nothing, and pulled him up onto his knees. Stiles looked back over his shoulder and found Derek smiling for real, before licking his lip and—oh Jesus Christ.
Stiles was just not prepared for that. How did one even get prepared for that?
Derek just dove right in, with what seemed like his whole face pressed against Stiles slippery ass, and Stiles cried out with pleasure. Derek wasn’t even doing anything, really, just nuzzled all up against Stiles’ junk. He just seemed to be breathing the scent in, but Stiles was rock hard again from the feel of it alone.
Stiles swore he almost died when Derek took one of his balls into his mouth, but then Derek let it drop and sucked at the other one, and Stiles was reminded of just how very much alive he really was.
Stiles wasn’t sure what was going on. All he knew was that he was out of control, moans leaving his throat without any sort of permission.
But if he thought that was amazing, it had nothing on Derek’s tongue. God, Stiles wasn’t exactly sure when Derek started licking his way around Stiles’ underside, but Stiles couldn’t help but push back against it, wanting that tongue everywhere all at once. Then Derek paused, tongue leaving his skin, and Stiles whined. He was about to protest when Derek finally leaned back in, and gave Stiles a tentative lick across his hole.
And scratch that. Scratch it all. Stiles knew where he wanted Derek’s perfect tongue and it was right friggin’ there. He couldn’t help but push back into it, and the movement seemed to give Derek some kind of reassurance, because he didn’t falter again. Just lapping over it and around it, before grabbing Stiles cheeks and pulling them further apart so he could push his tongue inside.
Stiles didn’t know how long they stayed like that, with Stiles on his knees, whining and begging as Derek undid him with his tongue, but Derek seemed content to stay down there forever. Derek didn’t even stop when he started to open Stiles up, just moved his head over a bit and slid in a finger next to his tongue. Stiles felt worshipped as Derek continued to open him up, never pulling his face even a fraction away from Stiles’ ass, and from the sounds Derek was making, Stiles got the feeling that Derek physically couldn’t make himself.
It was only after he got three of his fingers into Stiles did Derek pull his head away. Leaving Stiles’ ass stretched around his fingers with small licks around his hole. Derek growled at the loss, but flipped Stiles over onto his back, his fingers carefully twisting with the move, like Derek couldn’t make himself pull them out, but didn’t want to hurt Stiles with the strange angle.
Then Derek just fucking watched. Just fucked three fingers into Stiles and watched Stiles, sweating and writhing, as he ruined him. Stiles must’ve said please fifty times before Derek final broke with a loud growl, and pulled his fingers out long enough for him to strip out of his own clothes. Stiles wasn’t at the top of his game, but he was pretty sure that he heard a significant amount of ripping and tearing.
Stiles was ready when Derek loomed back over him on the bed, popping the lid of his lube once more to pour some on his hand. Stiles bit his lip and eyed Derek’s cock. He was pretty sure it was the best cock he’d ever seen; and Stiles wasn’t just saying that because Derek actually wanted to fuck him with it. No. It was nice. Stiles had to touch it. He did, and Derek’s mouth fell open and yep, those were definitely fangs. Stiles tightened his grip and gave Derek a few strokes, the wolf’s eyes squeezing shut as Stiles got him nice and slick. It was strange and intriguing, really, Stiles had never touched an uncircumcised cock before, but for once in his life he didn’t let himself get distracted. He probably couldn’t have even if he wanted to, Derek was sucking Stiles in. Figuratively speaking—and wow.
Now that was a distraction Stiles could allow.
Derek didn’t suck anything, though, but Stiles wasn’t put off in the least. Not when the alternative was Derek pushing away Stiles’ hand and manhandling him in quick werewolf roll, so Derek was underneath him on the bed. Stiles saw a chance and he took it, nuzzling himself into Derek’s neck.
“God, I can’t believe this is really happening,” Stiles moaned into Derek’s neck. He probably looked like some kind of spider-monkey, latching on to Derek like he did, his lanky limbs spreading and grabbing any part of the wolf they could find.
“Are you sure—“
“I swear to God, Derek,” Stiles warned. “If you ask me if this is okay, I will fuck you up. Because this is fucking perfect.”
Stiles meant to lean back to look at Derek, meant to gauge his reaction, but the movement caused him to slide back, and Stiles eyes fluttered closed and he moaned.
Because that was Derek’s cock. Derek Hale’s perfect cock that was lubed up and rubbing against Stiles’ ass. Touching his hole. The one that he was about to fuck. Stiles rubbed back against the length, and whined.
“Please.”
Derek gave him a sort of lost look that Stiles couldn’t decipher, but he guided Stiles’ up, and lined up his cock, flicking the tip against Stiles’ hole a few times, before gently pressing into it.
“There,” Derek gasped. “Don’t hurt yourself.”
Stiles thought that was ridiculous and sank down a little too fast, the head popping in all at once. The feel of it was nearly stunning, and every muscle in Stiles’ body tensed up. He didn’t understand how it could possibly have burned that much. Stiles had just had three of Derek’s fingers in him, and he was pretty sure that had been a wider stretch. Derek did have giant manly, werewolf fingers, after all. But the feel of his dick, hard as a rock, thick and full inside Stiles, was different somehow. All new levels of penetrating. Below him, Derek was growling out, “damn it,” and murmuring something about Stiles never listening, but Stiles wasn’t really hearing it. The buzzing was too loud. It started in his ears and traveled down his spine and pooled in his ass.
“Fuck,” Stiles breathed. He was faintly aware of Derek’s tight grip on his waist, keeping him from sinking down any further.
Derek growled out his name and Stiles’ eyes snapped open.
“That’s the worse part, I promise, do you want me to keep going?”
Stiles nodded. He’d felt pain worse, the sensation really just stole the breath out of him. He felt so full. So stretched.
Derek lifted an arm and petted Stiles’ hair, then let his hand trail down Stiles’ body until he reached Stiles’ cock, wrapping it up and slowly stroking.
“Relax,” Derek said and Stiles nodded again, trying to do just that.
He focused on the full feeling in his ass, and the large hand on his cock. The burn soon faded, and Stiles loosened his muscles. He trusted Derek not to let him hurt himself again.
Instead of thrusting up into him, Derek slowly eased up the hold he had on Stiles’ waist, and guided Stiles down a little at a time. That was not how Stiles expected that to go. Ever. All Stiles fantasies were much rougher, Derek all needy and anxious.
Stiles didn’t have time to be put off though, because before he knew it he’d bottomed Derek out, his stretched out hole resting against Derek’s trimmed pubes.
“Oh my god,” Stiles breathed. He couldn’t tell if he was relaxed and only being held up by Derek, or if every muscle in his body was wound tight. It was like nothing existed besides Derek’s cock, Stiles’ ass, and the rushing feeling washing over Stiles neck and back.
Stiles was faintly aware of his own cock too, which was somehow still hard, thanks to Derek continuously stroking it. But all true awareness Stiles was capable of gathering was busy focusing on the feel of Derek inside him.
It still burned, but it was never really the pain that had Stiles concerned. The feeling was so foreign, so strange. It was nothing like having fingers inside him. Derek was so hard, and Stiles swore he could feel Derek’s heartbeat in his ass . . . or maybe that was his own. All Stiles could do was give the hardness an exploratory squeeze.
Derek fucking whimpered, and Stiles was thrown back into reality. The sight of Derek underneath him, eyes squeezed shut, his hand like an iron grip on Stiles’ hip. Now, that was more like it, Stiles thought as he rocked back, and the sound that the movement ripped out of Derek was satisfying, but the angle had Stiles burning in a whole new way.
“Oh my god,” Stiles groaned again. “It feels sofuckingweird.”
“I know,” Derek answered and Stiles could tell it was through gritted teeth. “But it will be fine . . . it will be good, I swear. Do you trust me, Stiles?”
Stiles could not fathom having that argument verbally right then. With like, all eight inches of Derek’s cock in ass. God, Stiles didn’t even know if Derek was that hung, he couldn’t remember, but it felt like so much more.
Stiles tore Derek’s hand free and braced himself, hands reaching behind him, gripping onto Derek’s thighs.
After the first time that Stiles lifted up and sank down, everything changed. Derek was a mess underneath him. Honestly, Stiles had never seen the wolf so debauched. He was furry, then not. Fanged out, then not. Back and forth as Stiles’ kept working himself up and down on his hardness. Derek’s hand left his cock after a few bounces to grip the sheets with clawed fingers. Stiles’ was grateful, because he was rapidly learning the appeal that was anal sex. If he rolled forward Derek’s cock dragged along his back wall, if he rocked backwards, it would slide down the front wall. Each alteration scratching something inside of Stiles’ that wasn’t exactly an itch.
Wherever Derek’s cock was, warm and heavy and pressing, relived a pressure in Stiles, stopped the burn. Somewhere in the back of his mind, Stiles’ knew that his logic was fucked up, and he was probably going to be sore as hell afterwards but he couldn’t make himself stop.
Then Stiles’ learned, really and truly. He thought he figured it all out, thought he knew, thought that that was what it was like to ride a cock . . .
Stiles didn’t think he’d ever been so wrong in his entire life.
Because then Derek moved. Just a small, tiny readjustment of his hips, sliding down, then pressing up into Stiles’ when Stiles sank downwards.
The movement had Stiles’ seeing stars, and he mewled, whined, whimpered, everything. A string of continuous noises left his throat, because he needed that. Needed Derek right there, always. Again and again.
Stiles knew that nothing that was coming out of his mouth made sense, but Derek seemed to register his pleasure still, and angled his hips even more. Stiles’ couldn’t stop, he was bouncing. There was no other name for it. Stiles was bouncing up and down on Derek’s cock as fast as he could. The hardness rubbing that spot inside him over and over again, the friction felt like it was starting a fire inside him that had flames made of pleasure and all around awesomeness.
They only warning Stiles had before he came was a sudden hot weight that pooled in his belly that felt like it needed to be shoved out, so Stiles went even faster, pushing at it. Then the muscles in Stiles’ ass were clenching so tight around Derek’s cock that it felt like it might disappearing inside him. But Stiles had no time to worry about Derek before his orgasm was ripping through him.
Stiles cried out, his cum shooting out across Derek’s belly. Every single one of his muscles was involuntarily stiff again, but this time it was with pleasure. There was no pain, only a glowing high, Stiles’ pulsing dick, and Derek’s hard cock that was still somehow slamming up into him.
Stiles only had a second to revel in the fact that Derek was finally, finally fucking back up into Stiles, before the wolf was letting out a low, guttural sound and pumped his own orgasm out in Stiles’ ass.
Stiles smiled at the feel of wetness inside him when he absently fell unto Derek’s chest, with the wolf still jerking up into him a little bit.
Stiles wasn’t sure how long he’d stayed like that, but Derek seemed to content to stay like that way forever. It was only when Stiles’ high finally faded, after his breathing slowed back down, did Stiles notice the slight pain in his ass and slid off Derek and on to the bed next to him with a slight hiss.
“You really messed up now,” Stiles declared, and snuggled against Derek’s side, thinking how the burn was the best kind of pain he’d ever experienced. One of his over-worked legs fell heavily on top of Derek’s waist. “You’re never getting rid of me.”
Stiles meant it as a joke, but Derek surprised him by growling and flipping on to his side so that he could nuzzle into Stiles’ neck again.
“Good.”
Yeah, Stiles felt thoroughly ravished. Finally.