Halfway through writing his final paper for his History of Mythology course, Stiles realizes that he left his source material in Derek’s loft. Stiles came home early for the summer because he only has this one paper that just needs an electronic submission, and when the whole pack was at Derek’s the other day, he had been working on it a bit. But now the paper is due in five hours and the only way it’s going to make any sense at all is if he has his text—which is how he ends up in Derek’s building at 6:30 on a Friday night, when he would much rather be having dinner with his dad or playing video games with Scott or anything else besides this stupid fucking paper.
He pulls open the door without knocking and gets half a step inside the loft before he notices. Derek—lying on his bed—face down—naked. His face is buried in his own pillow, his left hand curled under his stomach, no doubt jerking himself off, while his right hand manipulates a big, navy blue dildo that Derek is currently pushing deeper and deeper inside of himself with a low, eager moan. And he—he has no idea that Stiles is there. Derek is masturbating—quite creatively, Stiles might add—and he has no idea that Stiles is there. That Stiles is watching.
Derek’s hips pump, shoulders straining, and he sighs, soft and sweet like he’s getting a fucking massage or something, and Stiles realizes with a start that he’s staring at a grown werewolf get himself off. He turns and runs before he can stop himself, tripping over his own feet in his haste to get out, and he knows that he definitely made some squeaking noise, some desperately apologetic yelp as he turned towards the stairs and fucking bailed.
He can’t stop replaying in his head on the way home, the way Derek was arched, the way he was sweating, the noises he was making. Stiles is so fucking hard that he has to limp up to his bedroom and jerk off with his back against the door because he can’t wait another fucking second.
It isn’t until he’s cleaning himself up with tissues that he remembers he forgot the fucking textbook.
When Derek Hale drops in through his window the next night, Stiles is almost certain he’s time travelled. Derek is slightly more normal now—he comes in through the front door when he needs something, and he’s polite to Stiles’ dad and, sure, he and Stiles don’t really get along per se, but they’re not so much mortal enemies anymore. So this regression in behavior is worrying for about three seconds, before Stiles remembers.
“Oh, shit,” he says, jumping up from his bed. “Okay, dude, it was a totally innocent mistake—I needed my textbook. And you never lock your door. And seriously, I really needed that textbook, and so I came over and then you were—you were—”
“It wasn’t like I did it on purpose or anything, you know? Because you definitely should masturbate more if your mood is any indication, and so it’s a good thing, you know? To get your, uh, groove on with yourself, um, and any other objects you may choose to use—”
“Stiles,” Derek says again. “Shut up.”
Stiles bites the inside of his mouth for a second, considering. He should wait, see what Derek has to say, but. “It’s just—this goes against all of the bro rules. Like, me and Scott, I’ve seen his dick, sure, but I’ve never seen it—in action. Not that I saw your dick! Because I didn’t. I mean, not the one attached to you. The other one, the blue one, I saw that.” He laughs, a little hysterically. “Give a whole new meaning to ‘blue balls’, huh?”
Derek blinks. “Stiles.”
He glances down at where he’s bulging through his khakis. “Yeah,” he says weakly. “Yeah, that’s a reflex now. You should probably leave because in about three seconds I’m about to combust out of embarrassment and take the whole house down with me.”
“You’re saying that a lot.”
“Because you won’t stop talking.”
“What is it?” Stiles asks, sure that his whole face is pink in a blotchy blush.
“You can say no.”
“You can say no,” Derek says again, and he takes a few steps forward until he’s standing right in front of Stiles. “Okay?”
Stiles swallows. “I can say no. To—to what?”
Derek doesn’t drop his eyes from Stiles’, but Stiles can feel Derek’s hands come up and unbutton his pants, slowly, methodically, easing his fingers between the waistband and the skin of Stiles’ hips. He gets one big, warm hand into Stiles’ underwear, and Stiles’ mouth falls open as Derek takes his cock into his palm and just holds him.
“Oh,” Stiles says.
“Sit,” Derek says, and Stiles does, sitting at the foot of his bed without a second thought. Derek doesn’t lose his grip, though, falling to his knees between Stiles’ legs, left hand spread out over Stiles’ thigh. “Lie back.”
He does, collapsing with his back flat on the mattress, arms flung out to either side. He stares at his ceiling and thinks about how fucking weird this all is while Derek lets go of his dick to yank down his pants and underwear almost to his knees. He pulls on Stiles’ hips, pulls them off the bed and lets Stiles’ knees rest on his shoulders, and Stiles is so hard he’s going to lose his mind—
Derek runs his thumb over the head of Stiles’ cock. A bit of pre-come escapes and Stiles moans reflexively, wanting so badly to arch into the touch, to try to get more friction, but he doesn’t move. He can’t.
“You can say no,” Derek repeats once more, and Stiles whines, shakes his head.
“I’m not saying no,” he says, heart pounding in his ears. “Derek—please—”
When Derek sucks him down, it’s not like it’s a surprise. He assumed, given the position Derek manipulated him into, that this is what it would lead to, but—it’s still shocking. It’s still overwhelming. It still makes him cry out and throw his hands into his hair and do his best not to fuck Derek’s face like some oversensitive teenager who’s never had someone touch his dick before. So he stays still and whines like a child and tries not to think about Derek bobbing up and down on his cock, slobbering and sucking and taking him deep into his throat. He tries not to think about Derek licking him from base to tip and sliding the point of his tongue into the slit, about Derek’s left hand cupping his balls firmly as Derek takes him all the way into his throat with one swallow.
He has no idea, no fucking clue, how this went from him explaining away his stupidity to getting his dick worshipped by Derek Hale. But he isn’t looking to question it, not now, not while he’s seconds away from coming.
He says Derek’s name when he feels his orgasm threatening him, teetering at the edge in his stomach, warning him. Derek, unsurprisingly, pulls his mouth off of Stiles and says, “Don’t.”
“What?” Stiles asks. “I won’t come on you, it’s fine—”
“No,” Derek says. “Don’t come yet.”
Stiles whines weakly. “Derek.”
In response, Derek slides his right hand along Stiles’ knee as he nuzzles against the soft skin of his inner thigh, biting gently as he goes. “You can wait; I know you can.”
“You’ll thank me later.” He continues the path of his right hand, up around Stiles’ ass cheek, which he palms thoughtfully, and under his thigh, right behind his balls, where he carefully presses his thumb against Stiles’ perineum, rolling little circles into the skin.
Stiles jerks like he’s been shocked, the little ministrations of Derek’s thumb sending waves of pleasure through him, coupled with the fact that Derek has returned to sucking him down over and over and over again. He knows, logically, that Derek’s simply massaging his prostate from the outside, that this is a thing plenty of guys do on a regular basis, and yet, to him, it feels like some kind of magic, and he never wants it to stop.
He keeps himself from coming by sheer force of will, so eager to keep feeling these crashing waves of vibrating pleasure from his core. He clings to the edge for as long as he fucking can but soon, he’s trying to shove Derek away with his last few moments of clarity. Derek doesn’t go, grips Stiles’ thigh with his left hand and sucks him down with a slurp and Stiles comes, crying out as his whole world goes white.
When he can feel his own limbs again, he hurries into a seated position and grabs Derek’s face, pulling him into a sloppy kiss. He can feel Derek’s stubble under his fingers, Derek’s soft lips under his, Derek’s tongue with the sharp taste of Stiles’ come poking into his mouth as he kisses back just as eagerly.
“Let me get you off,” Stiles insists, already dragging his hands down Derek’s chest, nearing his waistband. “I’m good at it, I promise.”
“It’s fine,” Derek says, voice thick and rough. Stiles nearly moans, wants to bask in the fact that he did that to Derek.
“C’mon, I want to—”
“I gotta get going,” Derek tells him, but he drags Stiles back in for another filthy kiss, one that he feels all the way down to his toes. “Knock next time you come to the loft.”
Stiles snorts. “Yeah, right.”
There’s a pack meeting a few days later. Stiles sits out in the parking lot of Derek’s building, sits in his Jeep with his knee bouncing up and down until Scott pulls in on his bike. He cannot and should not be alone with Derek any time in the near future. If Stiles had gone up there without supervision, there’s no telling what he might have done.
So he follows Scott and keeps his hands in his pockets and doesn’t think about the fact that, somewhere in Derek’s apartment, there is a big, blue dildo that occasionally makes itself at home in Derek’s ass. Scott elbows him sharply, standing beside him in the elevator.
“Dude,” he says.
Stiles clears his throat. “Sorry.”
The meeting is short and sweet, checking in, talking about border patrols for the week. Stiles sits there, silently, staring at a spot on the floor and thinking about Coach Finstock’s grandma skinny dipping to try to keep his head out of the clouds.
When it’s over, he jumps to his feet and nearly sprints for the door. Except Derek calls his name, and his heart lurches into his throat.
“You need something?” Scott asks, hesitating in the doorway. Everyone else has already escaped. It’s summer. It’s beautiful outside. They all have things to do, people to see. Even Scott is trying to hurry because today is Kira’s first day off of work in two weeks.
“It’s fine,” Stiles says. “Go on, I’ll see you later.”
Scott pulls the door closed behind himself and Stiles turns to face Derek, standing in the middle of his apartment with his arms crossed over his chest. Stiles doesn’t speak. He doesn’t move. He barely blinks. So they stand in a silence so deafening that Stiles wants to put in earplugs. They stand there for a long, heavy moment—and then Derek has him pressed against the door, Stiles’ legs wrapped firmly around his waist, their mouths locked together, and Stiles has no idea which one of them moved first.
He groans, dragging his nails down the back of Derek’s neck. “Fuck,” he whines. “God—your fucking mouth.”
“You’re so easy,” Derek tells him, rolling their hips together. “Already rock hard, in fucking seconds.” He presses his weight more firmly into Stiles’, manages to grind his dick right against Stiles’ as he moves, and Stiles can’t help but moan, grinding right back.
“It’s because I can’t stop thinking about it,” Stiles confesses. Hearing the words out loud, saying them out loud sends a spark right to his cock. Derek makes a soft noise, and Stiles’ heart surges. “I can’t stop thinking about fucking you, Derek—I can’t stop thinking about spreading you open with my fingers and putting you on my cock, watching you lose it, watching you love it.”
Derek drops his forehead to Stiles’ collarbone. “Stiles.” He says it softly, lowly, like he’s asking for something. Like he’s pleading.
It fuels Stiles on, makes him bolder, more confident than he’s ever been with sex. “I would’ve been so good to you the other day, would’ve done whatever you’d asked of me. I wanted to—I wanted to see you spread out on my bed, moaning into my pillow while I fucked you slowly, left bruises on your hips from holding you so tightly.”
“That’s how you want me, huh?” Derek encourages, tilting his head to kiss the base of Stiles’ throat, wet and careless.
Stiles bites his lip, tries to think about it through the warm haze of Derek against him. “No—not the first time. The first time, I want to see your face. I want to see the way your eyes blink closed and your mouth falls open. I want to see what you look like when your breathing hitches the first time I push inside of you, and I want to see you squirm on my cock as we fuck—all—night—long.”
Derek’s breathing is faster now, his heart thudding against his chest. Stiles can feel it against his muscles, feel it in his skin, the way he touches Stiles, the way he pulls Stiles’ hips closer.
“You should come,” Stiles decides, “so that I can fuck you. You’re gonna come, right now, and I’m gonna fuck you until you’re hard again and you’re gonna come all over me again—and again. I’m gonna make you come so many goddamn times, Derek.”
Stiles doesn’t even know if Derek is listening anymore. He’s grinding against Stiles fitfully, leaning into Stiles’ throat. He’s making soft, tentative noises, and his dick is so hard against Stiles’ hip that it could practically cut diamonds.
“Derek,” Stiles coos, “c’mon, you’re gonna come for me, right? You’re gonna come right here, right against me, in your fucking jeans—yeah, Derek, c’mon.” He digs his heels into Derek’s thighs, arches against him. “So good for me, Derek, so fucking good—can’t wait to watch you lose it while I’m inside you, while I’m filling you up just like you need—”
Derek snarls when he comes, claws poking out against Stiles’ legs as he loses it, shuddering like a racehorse in Stiles’ arms, a soft, heartbroken noise escaping his throat. Stiles stays still, petting Derek’s hair and kissing his temple. When Derek lifts his head a moment later, Stiles could eat him up with a spoon.
“You should let me down now,” Stiles decides. “So that I can put my dick in you.”
Derek’s chuckle shakes his shoulders. It’s ridiculously endearing. “I like you like this,” Derek tells him. “Trapped. At my mercy.”
“Says the guy who just came in his jeans from a little frottage,” Stiles points out. “Who’s at whose mercy here exactly?”
“I’m gonna jerk you off now.”
“What about the—”
Derek kisses him quiet, unbuttoning his jeans and pulling his cock out of his boxer shorts. Stiles would protest, but he kind of loses all higher language function when Derek’s trying to make him come, so he decides it’s for the best to just sit back and let Derek destroy him.
It’s a good handjob, the kind that’s slow and torturous, the kind that makes his toes curl and his heart thud, the kind that comes with sweet kisses and soft bites on his neck. It doesn’t take long for him to come, to moan softly into Derek’s mouth as he shoots all over Derek’s hand.
He can barely keep his eyes open afterwards, even as Derek licks a few of his fingers clean and wipes the excess off on Stiles’ shirt. He grumbles in protest, but he has to cling to Derek a second later as he pulls them off of the wall and carries Stiles into the apartment to deposit him on the bed.
“I can’t stay,” Stiles says. “I’m supposed to have dinner with my dad.”
“Uh huh,” Derek says, pulling Stiles’ shirt up and over his head.
“I mean it. I can’t stay.”
“What time do you have to be home?”
“Okay.” He kneels at Stiles’ feet, grabs onto his shoes and tosses them towards the door. Stiles watches, too tired to tell Derek to cut it out. “Take a nap,” he says, and he shoves Stiles’ shoulders down. “I’ll wake you in time to get to dinner.”
“Where are you going?” Stiles asks, even as he curls up with one of Derek’s pillows.
“I’m gonna take a shower. Remember—I’m the one with come drying in his underwear.”
Derek should probably feel a little guilty about jerking off in the shower right after having sex with Stiles. It’s not like it was bad sex. It was good sex—Stiles has a way with words, especially filthy ones, and it was easy to get roped in by the way he was talking, the things he was saying about fucking Derek, about making it good for him. It was easy to come. It was good sex.
But only a few minutes after dropping Stiles in bed and getting into the shower, he’s half hard again, leaning into the hot spray as he thinks about Stiles’ ridiculous mouth, about Stiles’ cock in his hand, in his mouth, the way it felt in Stiles’ room the other day, to take him apart like that.
He’s a mess. He’s a mess over a teenager with long fingers and a pretty dick and a complete inability to keep his fantasies to himself. He probably would’ve gone his whole life without putting his dick anywhere near Stiles Stilinski—he would’ve stayed away until the kid had grown up and moved on, found other people, found other obsessions—and now. Now that’s ruined.
He leans against the cool tile in the shower, a stark contrast to the heat of the water. He has his lube already out because he needs this. He hasn’t fingered himself in a week, ever since Stiles barged in on him. He’s been too nervous, too on edge, but he needs it. So he leans, and he sighs softly as he presses two fingers into himself, his cock throbbing for attention already.
“Fuck,” he says lowly, moving his fingers carefully to start. There’s no use rushing, not when he has all the time in the world.
He can picture it with Stiles. If he’s being honest, he’s been picturing it for a lot longer than anyone would guess, but now… Now it’s so much more real, and that makes him simultaneously terrified and thrilled, because he doesn’t have to feel like a creep when he imagines that it’s Stiles beside him, fucking him open with two—then three—fingers, breathing against his neck as he opens Derek up just to feel the heat of his body, just to watch him come.
He teases himself for a little while, works at his prostate until he’s moments from coming and then backs off. He repeats that, again and again, milking that oversensitive gland until he thinks he’s going to explode—and retreating, just before he can lose it, because it’s so worth it. The buildup makes him achingly hard, makes how tight his balls feel and how lightheaded he is so worth it because when he finally does let himself come, he sees stars.
He sets an alarm for five-thirty and crawls into bed beside the snoozing Stiles, spooning him without a second thought. The boy huffs in his sleep, leaning back into Derek’s chest, and Derek presses his face into Stiles’ hair and falls asleep almost instantly.
The thing about Derek is that he likes cock. He wasn’t sure that he did in high school, and then his family died and he didn’t think about sex at all for a long time. Sex was only a punishment, only a thing that reminded him that his family was gone, and that his relationship with Kate was the reason why.
But then, after that, after he got over his fucked up notions about sexuality and his dick being cursed, there was Jeremy. He was funny and kind and he lived next door to Derek and Laura in New York. He went to NYU. He checked in on them, brought them coffee most mornings. He was twenty-one to Derek’s eighteen and it didn’t matter because Derek didn’t like him, not like that, but when Jeremy kissed him on New Year’s Eve, Derek knew he didn’t have to like Jeremy to like his body.
He got his first vibrator from a shitty sex shop on the corner of his block. He couldn’t use it while Laura was in the apartment, had to wait until she was at work and he had moments alone. There were other toys, other dildos that he played with, that he tried. He spent an entire month’s paycheck from working at the used bookstore across the street on various penis-shaped items. And he loved it.
Then he forgot, again, because he moved back to Beacon Hills with nothing but Laura’s Camaro and his dad’s old leather jacket. He had money, but he didn’t need anything. Except a pack.
He forgot, until hooking up with Jennifer had made him remember.
After Jennifer, there was this guy named Keith. They met at Jungle, went back to Keith’s apartment and Derek rode him on the floor in front of the couch. It was slow, tense, because as much as Derek had experimented in his youth with things made of plastic, flesh was an entirely different animal. They saw each other a few more times, but Keith didn’t get it. He wasn’t willing to just sit there while Derek bounced on his cock for an hour, wasn’t willing to wait while Derek angled himself properly to get his prostate. He was impatient and a boring lay, and Derek had gotten what he needed anyway: experience.
He’s picky. He needs someone who smells good, who isn’t too overbearing, who lets him do what he wants and isn’t scared of him. He needs someone who’s willing to try the things he likes, who’s eager to participate when asked and just as happy to standby otherwise. He needs someone like Stiles.
Stiles comes over on Wednesday afternoon with a pizza and a bottle of Jack Daniels that he obviously stole from his father. “I got Satomi’s beta to give me his method of diluting wolfsbane in alcohol so that you guys can feel the effects, and since you’re the biggest masochist of the group, I figured I should bring it over to you to try.”
“I don’t drink whiskey,” Derek says, standing from where he was lounging on his bed to join Stiles on the couch. “I’ll eat the pizza, though.”
“This is primetime pizza, Derek,” Stiles informs him, flipping open the lid. “Domino’s, every kind of protein you could possibly want, extra garlic in the crust seasoning because you secretly love it, extra large because you’re a fucking werewolf. I’m expecting so many blowjobs in return for this.”
“Okay,” Derek says easily, and he kisses Stiles’ jaw affectionately before grabbing a slice. “What’s the occasion?”
“Why the pizza? And the booze?”
Stiles chews thoughtfully. “I thought maybe me coming over and then, you know, coming might have made you feel like a cheap date. So, pizza.”
“I don’t feel like a cheap date. And if I did, the fifteen dollars you spent on this pizza would not be the thing to turn it around. Besides,” he continues as he takes a huge bite, “it was one time.”
“That you came over and came on my hand and fell asleep in my bed,” Derek says, chest warming at the simple memory. “And I liked it,” he adds. “But I appreciate the gesture.”
“Sure it happened once,” Stiles says, “but it’s gonna happen again.”
“Right now, probably. And probably later in the week. And probably after the next pack meeting. And, you know what, I’m gonna put some money down on the full moon actually, because I’ve seen Scott on full moons, and he clings to Kira like a literal puppy.” He leans back against the couch, puts his feet up on the coffee table. “I’m gonna turn on the TV.”
Derek nods distractedly. His wolf is currently preening at the attention from Stiles—Stiles brought him food; Stiles wants to have sex with him; Stiles wants to be in his home. He could howl with satisfaction right now, but instead he eats pizza and watches some brightly colored Cartoon Network program.
When the pizza is three-fourths of the way gone and Stiles’ fingers are sticky with grease and Derek is full, he brings Stiles a damp paper towel and knocks the boy’s legs apart, falling to his knees on the hardwood floor.
“Whoa, hey,” Stiles starts to say, but Derek ignores him, unbuttoning his jeans, pulling out his cock. He’s cut, a good length, soft and silky and pretty. Derek likes watching him fatten up in his hand, watching him get hard as Derek strokes him. He presses his thumb right under the head and Stiles moans softly, says, “Fuck.”
“You can fuck my mouth,” Derek tells him, tilting his head so he can put his tongue against the base of his cock, drag it up over the shaft. He tastes like salty skin, like sex, like Stiles. “Okay?”
“Yeah,” Stiles says shakily. “Yeah, okay, I—yeah.”
“Don’t get pizza grease in my hair.”
It’s not slow. Stiles stays still for a few minutes, clean fingers combing through Derek’s hair, clinging every once in a while. His breathing is rushed, his heartbeat fast, but he doesn’t move. Derek does his thing—he enjoys this, loves taking Stiles apart like this, breaking him down and building him back up again. He loves taking Stiles’ cock into his throat, holding him at the base while he tastes every last inch of him, dragging his tongue along the length, teasing the slit, stroking him while he catches his breath.
When Derek takes him in again, Stiles’ hips roll tentatively, thrusting further into Derek’s mouth. Derek takes it easily, opening up his throat to accompany the extra length, and Stiles releases a shuddering breath.
“Fuck, Derek,” he says, and his hands in Derek’s hair tighten. “You’re so fucking hot. You know I can’t stop jerking off—every time I have a few minutes alone, I can’t keep my hand off my dick, thinking about how goddamn hot you are, how good you feel against me, how hot and wet and perfect your mouth is.”
The words spread heat throughout his body, make his balls tighten. He leans into Stiles’ hands on his head and is rewarded by Stiles thrusting again, deeper this time, more confident. After that, Derek doesn’t have to move, can just keep his head still while Stiles does all the work, arching his hips over and over again, panting as he fucks Derek’s throat.
Derek is rock hard in his jeans—he likes giving blowjobs, knows that it turns him on, but this is so much more. The asphyxiation combined with Stiles’ scent, with Stiles’ moans, with the heady knowledge that Stiles has never done this, that Derek is getting to see Stiles in a way no one else has ever seen him before—that’s what’s made him so hard he could burst through his zipper.
Stiles fists up Derek’s hair when he comes, head falling back against the cushions, groaning from deep in his chest. Derek swallows all of it, licks Stiles clean until the boy is pushing him away from oversensitivity. Derek mouths at his thighs instead, basking in Stiles’ afterglow, rubbing his nose and cheeks into his hairy legs while his chest glows with contentment.
“Stand up,” Stiles says, pushing at Derek’s shoulders halfheartedly. “C’mon, stand up.”
So Derek does, knees popping as he rises. Stiles tucks himself back into his jeans and grabs onto Derek’s hips, making him take a step forward so that his crotch is right in front of Stiles’ face.
“You’re gonna be patient with me, okay?” Stiles asks, unbuttoning Derek’s jeans. “Because I’ve never done this and it will probably suck a little.” He laughs quietly to himself, and Derek can hear him mutter, “Suck a little. Classic.”
Derek rolls his eyes, palms the back of Stiles’ neck. He wishes they could be on the bed, wishes Stiles would finger him open while he did this, but that might be too much for his first time. If he hasn’t blown another guy, he definitely hasn’t fucked one, and trying to get him to do both at once would undoubtedly result in some kind of Stiles-shaped disaster.
Stiles makes a weak, broken noise when he pulls Derek’s cock from his boxer briefs. Derek had forgotten, until this moment, that Stiles hasn’t actually seen him naked yet, didn’t know what he was signing up for.
“You don’t have to,” Derek tells him, and Stiles’ wraps a hand around Derek’s dick without saying a word.
Derek forgot what it was like, being in someone else. It’s been a long time—Jennifer was the last, and he still doesn’t like to think about it. With Stiles, it’s the same and different. The same in that his pretty pink mouth is soft and hot on Derek’s dick, a little unsure but eager to please. Different because Stiles is Stiles. Different because Stiles is gripping Derek’s hip hard, just like he likes, is trying so hard to keep Derek in his mouth that he’s slobbering down his chin, is moaning while he sucks Derek’s cock because he likes it, and Derek can feel his knees weakening just at the sound.
Stiles lifts his mouth away after a few minutes, peppers Derek’s hips with kisses as he yanks his waistband further down, down over his ass, halfway down his thighs. He doesn’t say anything, but his cheeks are red with a blush, and instead of resettling his hands on Derek’s hips, he grabs the globes of Derek’s ass and takes him back into his mouth, fingers pressing so tightly against the skin that there will be ten little bruises for a few minutes afterwards.
Derek loves the imagery, loves that Stiles is silently telling him how much he loves Derek’s body. He feels wholly appreciated, understood on a level he doesn’t think he’s ever reached with someone else before.
When he feels himself on the edge of coming, he pulls his cock from Stiles’ mouth and thumbs Stiles’ lower lip. He looks disheveled, hair messy, mouth swollen and pink, pupils huge, drool bathing his chin. Derek tucks his thumb into Stiles’ cheek.
“I’m gonna come down your throat,” he says, and Stiles’ hips make a small jerking motion. He doesn’t give the boy any time to respond, fits himself into Stiles’ mouth again and lets him continue his attention to Derek’s cock. He’s floating in that heavy space right before coming, where he knows it’s an inevitability, any fucking moment—and then Stiles’ right hand releases Derek’s ass and Stiles presses a dry finger right against his hole—and he comes with a cry, digging blunt nails into Stiles’ shoulder.
Stiles isn’t really an overachiever. He’s always kind of done the least amount of work necessary to get him where he needs to be, and while he works hard within his role as a pack member, it’s not like he ever put unending hours of work into his academics or his summer jobs. He’s smart and competent, stubborn but understanding, and he will often consider other viewpoints and opinions once he’s been bothered enough to do so. So for the past few days, all Stiles has been thinking about is putting his fingers up his butt.
It’s not like he has to. Derek likes it enough that Stiles will probably never have to bottom. But if Stiles ever hopes to make Derek come his brains out, he should probably understand what he’s working with. How can he know the best way to finger him if he doesn’t have a little experience already? How can he understand what Derek is really feeling?
He has lube already—he fucking should, or else he’d be so chafed that he couldn’t put on underwear. It only takes a quick Google search to confirm that he can use that stuff for more penetrative purposes, and then he just needs an afternoon with his dad out of the house and Derek distracted with other things.
He showers—thoroughly—and he has a towel on the bed and one sitting on the floor too, just in case. He’s not hard at all when he locks his bedroom door and crawls onto his mattress. He’s maybe a little nervous, unsure, but determined all the same. His plan is to lie back and think of Derek, think about Derek’s mouth and his big hands and his pretty eyes.
He strokes himself first, tugging on his balls and letting his cock fill, jerking himself slow and simple, imagining that Derek is beside him, whispering to him all the terrible things Stiles is going to get to do to him as soon as he figures it all out. It’s easy to get hard then, but what’s difficult is stopping himself before he comes, stopping so that he can do what he’s here to do.
One finger feels weird. It’s an intrusion, and it’s a pain to focus on his overall bodily feelings rather than what it is his one little finger is feeling. He breathes, kneeling in his bed, hand tucked behind himself. He breathes, eyes closed, and start to squirm in his middle finger as well.
Two feel twice as weird, but in a different way. It’s not good exactly, not yet, but it’s a more balanced weight, a better pressure, and it’s easier to breathe now, moving his fingers slowly in and out of himself. The fiction is something at least. It makes his cock twitch and his body shudder, but his dick is barely hard anymore.
He has to focus on thoughts of Derek. He’s doing this for Derek. So that he can make Derek lose his mind as he comes, make Derek see other fucking universes just from grinding on Stiles’ cock. If he can enjoy this, he can make sure that Derek will.
He adds more lube to his fingers, takes some time to circle his hole and relax, explore the sensations. By the time he’s riding two fingers, his dick is bouncing against his thigh, pre-come beading at the slit. Three fingers feels easier. His body swallows them up, and it burns at first, but he’s proud of himself because something clicks. He feels full. He feels like his body is buzzing with some new kind of pleasure, and he gets it. He understands why Derek would like this.
He’s taken science classes, understands biology and anatomy. He’s read plenty of articles in his research for this moment and so he knows where his prostate gland is. Preparing himself for what to do with it is an entirely different matter. It takes him long, awkward minutes and a painful wrist rotation to even figure out how to get at it, and by then it feels—strange. Good, but in a way that doesn’t match the rest of the sensations ringing through him. It feels too heavy, in a way he doesn’t know how to appreciate. He panics at the last second, pulling his fingers out.
He doesn’t see Derek that night. Derek doesn’t call and Stiles doesn’t go over.
The next morning, while his dad’s at work, he tries again. He goes a little slower, keeps his left hand on his dick the whole time, and he gets a little farther. He explores a little bit more, tries to play with his prostate.
He does it again the next day, and the day after that. And then, the morning of the day of the pack meeting, he rides his fingers in his bed for no less than a half hour, comes so hard while he’s milking his prostate that it splashes against his chin. He has to shower and scrub at his hands so Derek doesn’t know what he was doing, and he shows up to the loft fifteen minutes late.
By the end of the meeting, Derek has taken to staring at a spot on Stiles’ left ear like it’s the most interesting thing in the world, and Stiles’ stomach is twisted into knots. When the apartment clears, Stiles is standing in the kitchen, drinking from a water glass, waiting until the door slides closed.
Derek walks towards him slowly, hands stuck in his pockets. Stiles watches, patiently, until Derek comes to stop in front of him. For two seconds, neither of them moves. But Derek lifts a hand, cups Stiles’ jaw, and then they’re kissing, softly, Derek pressing him against the counter.
Stiles lifts his arms to wrap around Derek’s neck while they kiss. Derek tilts his head away, towards Stiles’ neck, and licks across his Adam’s apple.
“Der,” Stiles says.
He had been planning. He had plans, honestly, but right now… Right now Derek is holding him so gently, kissing him so slowly, that he doesn’t want it to stop. The fast and hard, the sloppy blowjobs, the intense orgasms—yeah, those are all very, very good things. But right now Derek feels like a puzzle piece against him, and Stiles wants to bask in that for a little while.
“Can we lie down?” he asks. “And just—kiss for a little while?”
In the back of his mind, he almost expects Derek to ask him to leave. That wasn’t what Derek signed up for after all. They’ve been building up to something, building up to something pretty intense, and there’s no reason Derek should want to slow down so that Stiles can have a lazy afternoon of kissing in a big bed with the sunset glowing from the big wall of windows.
But Derek doesn’t ask him to leave. His eyes are soft and the corner of his mouth twitches up, almost like a smile, and he nods. “Yeah,” he says. “C’mon.”
They settle into bed easily, Stiles half on top of Derek, both of them curled together with their heads on pillows. Derek kisses him, pulling him close, and Stiles lets himself revel in being close to Derek, lets him feel all warm and fuzzy about it. They kiss for a long time, alternating between shallow, sweet kisses, and deep, eager ones that have Stiles’ dick straining in his jeans.
Even though they’re both hard, even though they can both feel that they’re hard, neither of them move to do anything about it. Stiles just wants to kiss him, and Derek seems more than willing to participate. For over an hour, they just lie there, holding each other, and kissing.
Eventually, Derek dips his head to kiss Stiles’ neck and his stomach twists up pleasantly. He drags his beard along Stiles’ throat as he says, “Do you wanna stay?”
Stiles nods. “Yeah. Yeah—please.”
Stiles gets up to shower a few minutes later, tiredness already sinking into his bones even though it’s only late afternoon. Derek knocks softly on the bathroom door just after Stiles has stepped under the spray, and Stiles tells him to come in, leaning his head back so he can wash his hair.
“I ordered a pizza and a salad,” Derek tells him. “It’ll be here in a half hour, but you can take a nap if you want. I promise not to eat it all.”
Stiles hums. “Okay.” He pulls open the glass door, blinking at Derek. “Join me?”
Derek mostly just stands close to him while he washes, dragging the loofa down his chest, between his thighs. Derek stands pressed against his back, hands on his hips, mouth on his neck. He’s perfectly patient, unmoving, and eventually Stiles hands him the soapy loofa and says, “Do my back.”
He’s slow, methodical, still kissing Stiles’ neck but now dragging his hands all along his body. His touch is electric, even to Stiles’ exhausted senses, and he can’t help but lean back into him, reaching a hand around to tangle in Derek’s hair.
A shift in his weight causes Derek’s cock to press between Stiles’ ass cheeks, hot and firm against him. Derek is quick to pull back, but Stiles whimpers.
“You can,” he says quietly, wrapping a hand around his own cock. “You can do—do whatever—touch me—”
Derek drops the loofa to the shower floor with a wet thump and his hands come back to Stiles’ ass, thumbs pulling apart his cheeks. Stiles bites his lower lip, exhales shakily as Derek takes a half step closer and slots his cock right against Stiles’ hole, slick with soap and hot to the touch.
“Fuck,” Stiles says. “Do you like that?”
Derek nods against the back of his neck and thrusts his hips forward, sliding up the crack of Stiles’ ass. “Yeah,” he chokes out. “Yeah, Stiles, you’re—you’re so good.” He speeds up his movement, fucking against Stiles’ hole over and over again, and Stiles can’t help but jerk himself off, breath caught in his throat because this is something so far out of his comfort zone but also exactly what he wanted.
He comes too fast, crying out weakly as he shoots against the wall of the shower, shuddering. Derek is just as quick to follow though, gripping Stiles’ hips almost painfully tight as he covers Stiles’ lower back with his come.
He turns around immediately, wrapping his arms around Derek’s shoulders and kissing him fiercely. Derek returns the favor, even grabbing Stiles’ thighs and lifting him, pressing him back against the tile and keeping him close.
“I’ve been practicing,” Stiles finally admits, lust still thrumming through his veins. “Fingering myself. I wanted to know what it felt like so that I could understand what I was doing to you—so that when I open you up, I can make you feel so fucking good, Derek.”
“Yeah?” Derek croaks, biting into Stiles’ mouth. “You’ve been fucking yourself on those long fingers—I bet it felt fucking amazing. I bet you came so hard that you couldn’t move after, just sitting in your come, stuffed full of lube.”
Stiles moans. “Derek.” The other man ducks his head, sucking a mark into Stiles’ collarbone. “Let me do that to you. Let me show you I can make you feel good.”
Before Derek can respond, the sound of his cell phone buzzing insistently against the bathroom counter distracts him. “The food,” Derek says, and he sets Stiles down carefully before he darts from the bathroom, towel tied around his waist.