If anyone had told fifteen year old Stiles that he would be sharing an apartment with Jackson Whittemore six years later, he wouldn’t have ever believed it. He also wouldn’t have thought it possible that Jackson would eventually be one of his best friends. Hell, seventeen year old Stiles wouldn’t have even believed that would ever be his reality. But, somehow, that’s exactly what happened. Jackson came back during winter break of senior year, still the same asshole in so many ways, but London had calmed him, and life had forced him to mature just like the rest of them. He had left his parents in England, living on his own so he could graduate high school with the rest of his class, and there hadn’t been any posturing or desire for popularity this time around.
They had become frenemies that last semester of school, possibly more friend than enemy, not that either of them would ever admit it, even now. They were able to bond over the whole being possessed and forced to kill innocent people thing that no one else could really understand, which helped that friendship develop. Everyone always seems to couple up, too, and they were the single ones, which meant they often paired up when pack stuff happened. It was surprisingly nice, getting to know the real Jackson, or as much of the real Jackson as he’d let anyone know back then. Stiles figured they’d graduate, Jackson would go off to some fancy university somewhere, and they’d possibly keep in touch via skype for a bit until it became an exchange of Christmas cards every year.
But then Stiles managed to pull out a scholarship to Stanford, of all places, which was his dream school but never a real possibility. The whole pack somehow managed to pull out scholarships to their dream schools, full rides with living expenses, and none of them even applied for any of the alleged scholarships they received. If Derek chooses to spend some of the insurance money on the pack he left behind, well, Stiles isn’t going to call him out on it. The scholarship meant the chance to actually go to college, after all, instead of just joining the academy and following in his dad’s footsteps immediately. He still wants to go into law enforcement, double majoring in criminal justice and psychology, but he’s thinking more about looking into the FBI or SFPD for a while before returning to Beacon Hills. But, yeah, Stanford became a reality, and it happened to be where Jackson was planning to attend, so rooming together freshman year made sense. That became getting an apartment together sophomore year, and now they’re still sharing a place the last semester of junior year.
Jackson’s studying biology, with the intention of applying for med school after getting his bachelor’s. He originally planned to do law, since that was what he always expected to study, but he decided freshman year to change majors. He wants to fix people, has an interest in orthopedics after being involved in sports his whole life, and that’s what he’s doing. Stanford doesn’t have a pre-med major, but he’s taking the courses he needs to get into med school, so it’s all good. Stiles thinks he’s going to be an awesome surgeon, and he tells him that anytime he gets cranky or overwhelmed with his studies. Their friendship has reached that supportive level, did back during freshman year when they shared a dorm room.
Of course, their friendship has reached other levels, too. Neither of them really has the time or energy to date, and they aren’t into casual sex with strangers, especially with the whole supernatural world to consider, so they started taking care of each other’s needs during freshman year after too many times jerking off at night and listening to each other come. It’s like a friends with benefits thing that never goes beyond making out, jerking off, blow jobs, or some grinding on the sofa. By unspoken agreement, they’ve never gone all the way. At the beginning, it was because neither of them had actually done anything with another guy before, so jumping straight to penetration would have been a bit too fast. Then it was because neither of them really wanted to be that vulnerable, regardless of their friendship at the time. Eventually, it was because Stiles developed feelings that would complicate things between them and would definitely make going all the way into something more than Jackson might want.
It’s probably ridiculous that they’re both so stubborn about changing their relationship again, so they stick with the making out and never go further than blowjobs. For all intents and purposes, they’re dating. They’ve been dating for three years. They go out to eat, they go to movies, they cuddle on the damn sofa, and they even take vacations together. They kiss all the time. He doesn’t know how many hours they spend just kissing and licking into each other’s mouths. They know how to get each other off, the right pressure or suction or twist of the wrist and the words to murmur in each other’s ears to have the best orgasms ever. They even sleep together most nights. Naked and snuggled together in Jackson’s king size bed, Jackson the big spoon and snuffling against Stiles’ neck, waking up with morning wood that they always take care of together.
“Why are you frowning?” Jackson asks, pulling Stiles out of his thoughts with a sardonic drawl that would indicate to most people he’s merely being polite. Stiles, however, can hear the underlying note of concern.
“Just thinking.” Stiles shifts against the pillow behind him, moving his feet onto Jackson’s lap.
“You shouldn’t do that. It always leads to trouble,” Jackson mutters, arching a brow above the frame of his glasses as he looks at Stiles.
“Not always.” He sticks his tongue out, wiggling his feet until Jackson sighs and starts kneading one with his free hand. Jackson’s other hand is still holding the I-pad with the notes he’s reviewing for a test Monday. “You’re so good with your hands.”
“So you’ve told me.” Jackson smirks, the pretty bastard, but he’s digging his thumb into the arch of Stiles’ foot and it feels too good to complain. He’s grateful every day for Jackson taking that elective massage therapy class spring semester of freshman year. He lowers his I-pad and turns his head to look at Stiles. “What thoughts had you frowning?”
“Nothing bad,” he reassures him. Stiles shrugs. “I was just thinking how weird it is that I’ve had your dick in my mouth but never in my ass. Or vice versa.”
Jackson’s eyes widen slightly, and his grip on Stiles’ foot tightens. “Alright then. We’re talking about this now, I guess.”
“It’s time, isn’t it? Probably way past time.” Stiles nervously taps his fingers against his thigh. “I mean, I really like what we have, Jax, but we could have even more.”
“Could we?” Jackson pulls his glasses off, tossing them on the table before putting his tablet beside them. He looks down at Stiles’ feet, a tension in his shoulders that wasn’t there just a moment before, and a nerve in his jaw twitching as Stiles looks at him. “You really want that, Stiles? With me?”
“No, I thought I’d bring it up because it’s not something I want,” he deadpans, rolling his eyes as he moves his feet off Jackson’s lap. He crawls on his knees across the sofa until he’s right beside Jackson. “Look at me and use your words.”
“This isn’t a nightmare, dumbass.” Jackson sounds a little cranky, and Stiles wonders if he shouldn’t have said anything, after all. Finally, Jackson looks at him, and the expression on his face is vulnerable and hopeful and makes Stiles feel pretty foolish for not having this conversation months ago. Maybe years. “Are you serious or is this just you being horny?”
“I’m serious, Jackson. If I was horny, I’d go to a club and find some random dude,” he points out. “I’ve never done that, and neither have you. I don’t think?”
“No, I haven’t. You’re still the only guy I’ve ever been with,” he says firmly. “I need to know what you want, Stiles. I’m not going to jump conclusions based on your vagueness and end up..” He trails off, running his fingers through his hair. Stiles knows him well enough to fill in the blank: getting hurt.
“I want to move to that next level.” Stiles squeezes Jackson’s knee. “We’re already in a relationship, we’ve been exclusive since we were eighteen even if we never discussed it, and I want to make us official. Not just friends with benefits, but a different label. Whichever one you’re comfortable using. I want to tell my dad about us, tell the pack that it’s not just something casual, tell everyone around that you’re mine.”
“I—I need time to think.” Jackson leans in to kiss him, a gentle brush of his mouth against Stiles’, then he pulls back. “I’m going to go to my room and process all this. It’s not something I’ve really thought about before, never thought I could actually have it, and there’s a lot we could lose if it goes wrong.”
“It’s okay. I understand.” Stiles bites the inside of his cheek. He does understand. After all, he’s thought about this a lot in the last few weeks before deciding to bring it up. “Take your time. And, actually, I’ll go to my room. I have an essay to work on anyway, and my laptop’s already set up there.”
Jackson grabs his hand when he stands up, staring at him intently. “I’m not saying no.”
Stiles nods. “I know. It’s okay,” he murmurs, squeezing Jackson’s hand and smiling wryly. “I should have handled this better, given you some idea that I wanted more, so I can wait for an answer.” He leans down to kiss Jackson’s forehead before he pulls his fingers free and goes to the bedroom. There’s some anxiety in his mind now, not that he expected Jackson to just agree immediately.
Jackson isn’t very spontaneous, and he values having control over his life in a way that equals Stiles’ own need for control. That aspect of their personality can occasionally lead to bickering or outright fights. They’re also stubborn and opinionated assholes, so nothing is ever that easy for them. Even their current relationship status started out a little rocky as insecurities and vulnerabilities often got the best of them during those early days. They’re solid now, though, in a way Stiles can’t really define.
That’s one of the reasons he thought it might be the right time to talk about their relationship. They’re about to be seniors, after all, and Jackson’s going to have to figure out where to go for med school, and Stiles isn’t sure if he’ll actually work in the city or just go back to Beacon Hills. Time is running out, in some ways, and he needs to know if this is ever going to become something they acknowledge and can actually build together. It’s not like he’s seeing a happily ever after for them necessarily. They’re only twenty-one, so who knows what the future will hold, but he can see enough of a possible future to take the chance.
It takes him a while to stop thinking about Jackson and focus on the essay. He gets his outline done before he hears his door creaking open. Stiles saves his document before turning his chair around to face Jackson. “Everything alright?” he asks quietly.
“I want all that shit you said,” Jackson says. “The labels and stuff. Also the sex. I want you to fuck me, Stiles. And I want to fuck you. Boyfriends, I think? Seems like a good enough label for now.” He smiles wryly. “I’ve been yours since the first time we kissed, so why not make it official?”
“All that shit I said.” Stiles’ lips twitch. “You’re so romantic.” He gets out of his chair, hearing it roll back into his deck as he walks over to Jackson. “Boyfriends is good for me.” He leans over, kissing the corner of Jackson’s mouth. “I’ve been yours since then, too.”
“Really?” Jackson pulls Stiles’ head back and looks into his eyes. “Mine?”
“How could you ever doubt?” Stiles whispers, touching Jackson’s jaw, tracing his cheekbone with his thumb. “You make me feel so many things, asshole.”
“You’re good at hiding that,” Jackson mutters, rolling his eyes. “Don’t hide it anymore, okay? If we’re doing this, I need to know…I need to see how you feel.”
“I’ll try, but I’m used to keeping things close,” he admits. “We’ll probably both have to make some effort to ensure this relationship works out, huh?”
“Maybe a little.” Jackson snorts. “We’re both emotionally stunted assholes at the worst of times.” He kisses Stiles, moving his hands underneath his t-shirt and stroking bare skin. “Will you fuck me, Stiles? We can consummate the whole boyfriend thing.”
“Now?” Stiles clears his throat because that squeak was pretty damn embarrassing, and Jackson totally heard it, judging by the cocky smirk on his lips. Stiles narrows his eyes. “Okay. We can definitely consummate things. Get that pretty ass on the bed. I’m going to wipe that smirk off your face.”
“We’ll see about that,” Jackson taunts him, reaching down to pull his shirt over his head. Stiles is momentarily distracted by the flash of silver in his nipple, licking his lips as Jackson chuckles knowingly. “You reek of arousal. I wonder if you’ll even last long enough to fuck me.”
“Big words for someone who is about to be moaning like a wanton little—“
“Finish that sentence, and I’ll be the one fucking you tonight.”
“Nope. You already asked me to fuck you. No takebacks. Anyway, we both know how desperate you are to feel my big dick in that tight ass.”
“Yeah,” Jackson breathes out, eyes dropping to stare at Stiles’ crotch. “Have you ever fucked anyone in the ass before? Not to feed your ego, but you do have a huge dick, and I’d rather enjoy this even if I can’t sit down tomorrow.”
Stiles feels warmth spread over his face. “Uh, Malia and I did a couple of times. She also used a toy on me a few times after she found out I was bi. I know how to prep you, Jax. I don’t want you to get hurt.”
“Huh.” Jackson blinks at him as he shoves his jeans down. “That relationship was already through when I came back, so I wasn’t aware it was so adventurous.”
“Dude, you can’t get jealous about a high school girlfriend. You don’t hear me asking about all the people in London or Lydia, do you?” Stiles points out.
“I’m not—fine. I’m jealous. Whatever.” Jackson scowls at him before sitting on the bed. “You’re mine now.”
“Yes, I am.” Stiles pulls his shirt off before he pushes down his sweatpants. He trips as he tries to get them off his ankles, only missing a face plant on the floor because Jackson catches him. “Thanks.”
“I hope you have more finesse when your dick’s in my ass,” he deadpans, lips curving into a smirk as he bats his eyelashes at Stiles. Fucking pretty bastard.
“Fucking pretty bastard.” Stiles verbalizes his thought for once. He grabs the bottle of lube out of the bedside table and looks at Jackson. “Condom or not?”
“No. You’re clean, and I can’t catch anything. I want to get messy and sticky tonight,” he says, preening just a little. “Pretty, huh?”
“You know you’re gorgeous.” Stiles tosses the lube on the bed before he straddles Jackson. “And you’re all mine.”
“You’re a possessive little human, aren’t you?” Jackson kneads his ass as Stiles leans down to kiss him. Stiles rolls his hips slightly, nothing serious, just enough to get Jackson’s interest. Jackson’s pupils are already dilated when they pull apart from the kiss, cheeks flushed, dick hardening nicely. “I like how much you want me,” he murmurs, licking at Stiles’ lips. “Wish you could mark me and it would stay.”
“Me too.” Stiles kisses his way down Jackson’s face, licking at his neck, sucking on his skin. When he reaches Jackson’s nipple, he tongues the ring then tugs it with his teeth. Jackson makes a keening noise, shifting beneath him, and Stiles loses his balance, falling on the floor and hitting his ass rather hard. “Ouch. That fucking hurt.”
Jackson stares at him for a moment before he bursts out laughing. It’s a carefree laughter that Stiles doesn’t hear nearly often enough, and he just wishes it wasn’t caused by him falling on his ass when he’s trying to be sexy. “Want me to kiss it better?” Jackson asks when he’s finally managed to get himself under control.
“Only if you put on those scrubs you wear when you volunteer,” Stiles says, waggling his eyebrows as he moves to his knees and crawls towards the bed. “We can play doctor?”
“No,” Jackson says firmly. “It’s still no. It’s always going to be no. I’m not playing doctor with you.” He scoots back on the mattress and gives him a come hither stare that makes Stiles’ dick throb happily. “If you’re finished rolling around on the floor, maybe you could get up here and fuck me?”
“Ha! Shows what you remember. We played doctor when we were five at playschool,” Stiles reminds him. He gets on the bed, straddling Jackson’s legs and crawling up his body. “I listened to your heart, and you told me about a boo boo on your arm that I kissed better. Then you tried to steal a kiss and told me you were going to marry me.”
“Lies. Total lies,” Jackson murmurs, lids lowering as he watches Stiles. “I didn’t try to steal a kiss. I did kiss you. Right on the lips. Then you punched me.” He sniffs haughtily. “My mother refused to let me attend such a plebian playschool after that attack, and I spent the next ten years trying to make you miserable for rejecting me.”
“You just got off bullying me,” Stiles says, rolling his eyes even as he does remember their long ago friendship before that punch and, yes, kiss, but he tries not to remember that his first kiss happened at age five by Jackson Whittemore being precocious. “But the rejection thing makes sense if you actually thought a five year old could reject someone.”
“It hurt my feelings. I didn’t care if it made sense,” Jackson admits. “Anyway, that’s like fifteen years ago, so can we please focus on the whole sex thing happening right now?”
“I’m going to suck your dick and use my fingers to stretch you. Then I’m going to fuck you. Sound good?” Stiles leans down to mouth at the bulge in Jackson’s underwear.
“Yeah. Good.” Jackson bucks up, his fingers already gripping the blanket beneath him as Stiles teases his dick through his underwear. And Stiles does tease. He licks until the fabric is soaked and clinging, mouthing at Jackson’s dick, tasting pre-come against the fabric as he licks at the head. Then he mouths his balls, using more spit than usual just to make his underwear cling so nicely.
Stiles finally hears him growl, feels fingers in his hair, tugging just enough to get his attention. He looks up and smirks, wiping saliva off his chin. “What?”
“You know what, smartass.” Jackson pouts. “Take off my underwear and suck my dick.”
“Manners, Jax. Say the magic word,” he teases, pulling the waistband of Jackson’s boxer-briefs down lower, licking his happy trail and tonguing the light brown curls revealed as the underwear gets lower.
“Now,” Jackson growls, reaching down to shove his underwear around his thighs. “Or I’ll just do it myself.”
“No touching,” Stiles says, slapping at his wrist lightly when Jackson tries to stroke his hard dick. He tugs Jackson’s underwear down, tossing them on the floor before grabbing the lube. He squirts a little into his palm, warming it up before coating his fingers. Then he moves back between Jackson’s legs, sucking on the head of his dick as he rubs his fingers over Jackson’s hole. Jackson is making quiet noises, just grunting and breathing raggedly as Stiles teases his hole. When he starts to press a finger inside, it’s clenched so tightly that he can’t even get inside. “Relax. Push like you need to, uh, you know.”
“Your fingers are ridiculous,” Jackson accuses, but he takes a few breaths before his hole starts to unfurl. Stiles presses his finger inside, sucking more of his dick into his mouth. “God, that feels weird. I’ve used my fingers before, but it isn’t the same.”
While Jackson talks, Stiles slowly fucks him with his finger. He licks the underside of his dick, sucking on his balls as he adds a second finger when Jackson feels ready for it. He hears a low gasp, his pointer and middle fingers going deep inside his hole as Jackson starts rolling his hips, pressing down for more and fucking his dick into Stiles’ mouth. A few times, Jackson starts making noises like he’s close, so Stiles pulls off, gripping his balls and letting him come down before starting again. When he adds a third finger, Jackson clenches and makes a noise he’s never heard before. He looks up, watching Jackson’s face as he fucks him with three fingers. He’s not loose enough, not for Stiles’ thick dick, so he keeps sucking and stretching him with his fingers.
“Stiles, please,” Jackson whines softly, the words almost broken from his desperation. Stiles pulls his mouth off his dick, licking pre-come off his lips as he stretches his fingers. Jackson stares at him, pupils dilated so much that he can only see a ring of blue, lips swollen and bitten from where he’s trying to keep quiet. Stiles loves when Jackson makes noises, but it’s still one area where Jackson has trouble letting go and just being loud if he wants to be. “I’m ready. Fuck me.”
“Okay, babe. I’m gonna make you feel so good.” Stiles pulls his fingers out, wiping them on the blanket before grabbing the lube. He coats his dick before warming some and dripping it down Jackson’s hole. “Knees or back?”
“Like this,” Jackson murmurs, sitting up to kiss Stiles, sucking on his tongue before he falls back against the bed. His abdominal muscles look fucking amazing, and Stiles gets distracted ogling this gorgeous man that’s his, his! It’s unbelievable. He shakes his head slightly, focusing on making Jackson feel good. Jackson licks his lips. “I want to watch your face. Babe.”
“Hush. I’m brainless right now, and, anyway, you liked it,” he mutters, shifting to his knees. He rolls Jackson up, moving between his legs. “Slow or hard?”
“Make me feel it.” Jackson is tugging on his nipple ring, lips parted, looking so damn sexy that Stiles has to kiss him. So he does. He licks into his mouth, sucking his tongue as he rubs the head of his dick against Jackson’s hole. It’s the first time either of them have done this with a man, first time Jackson’s had his ass fucked, so Stiles goes a little slow at first despite Jackson’s choice. Jackson whimpers into the kiss when Stiles’ thick dick starts to stretch him, and Stiles is glad he chose to go slow at first.
He fucks in gradually, getting more of his dick inside Jackson’s tight hole with each thrust forward. When he’s finally completely inside him, he takes a moment to just enjoy the tight heat squeezing his dick. “Feel so good, Jax,” he whispers, kissing Jackson’s neck, just lying there with his dick fully seated in Jackson’s ass. “So good for me.” He sucks a mark that won’t last, but he knows how much Jackson gets off being claimed and marked, being wanted.
“So full,” Jackson breathes out, raspy against his ear. He starts to wiggle eventually, slapping Stiles’ ass cheek. “Move. I want more.”
“Bossy,” he says, moving his mouth down to lick Jackson’s nipple as he pulls out then slams back in. He tongues the ring, giving the right amount of pressure to make Jackson drag blunt nails down his back. Stiles fucks him hard and deep, but doesn’t go too fast yet. He wants to savor this, wants to make it special. They kiss again, Jackson rolling his hips, pushing down to meet Stiles’ thrusts. Stiles starts to move a little faster, hips snapping harder, balls tightening up. He pulls out completely, gripping the base of his dick, squeezing his balls and staring at Jackson.
“Damn it, Stiles. Stop making me wait!” Jackson growls as he moves suddenly, pinning Stiles against the bed, eyes flashing blue and claws growing before he ducks his head and calms down. But then he’s sliding down Stiles’ dick, gritting his teeth and panting as he starts to bounce up and down. Stiles reaches for Jackson’s dick, stroking him with a firm grip as Jackson rides him.
“That’s it, Jackson. Take what you want. Make me come in your greedy hole.” Stiles bucks up, thumbing the head of Jackson’s dick, jerking it with a twist of his wrist. It doesn’t take long before Jackson’s keening, his body shuddering as ropes of come spill onto Stiles’ hand and chest. That’s what he’s been waiting for. What he wanted to happen first. Jackson is still moving, bouncing and rolling his hips, his muscles clenching as he moves. Stiles stops trying to hold back. He thrusts up erratically, staring at Jackson as he feels his body starting to tense.
“Fuck yeah. Come in me. Make me yours, babe,” Jackson urges, staring into his eyes as he takes Stiles even deeper. Stiles snaps his hips up a half dozen times until his eyes roll back and his body tightens then shudders as he comes with a grunt. His dick pulses in Jackson’s ass, his come spilling inside, dribbling out onto his dick as Jackson keeps riding him until he’s totally spent. Jackson leans down and kisses him, come smearing on their chests and lower abdomens as they roll onto their sides.
They kiss for a while, laughing softly, just looking at each other and kissing more, touching and stroking, being complete dorks, not that they’d ever admit it. Finally, he eases his dick out of Jackson’s ass. “You okay?” he asks softly, stroking the curve of Jackson’s jaw.
“Sore, messy, kind of gross, but it’s all good.” Jackson moves his leg over Stiles’, tugging him closer. He puts his fingers against Stiles’ lips and smiles slightly. “No talking, Stiles. Not now. Just shut up and hold me.”
“Alright. We’ll just snuggle,” Stiles murmurs, stroking his fingers through Jackson’s sweaty hair and kissing him lightly. They are messy and gross, but Jackson gets off with them being sticky with come and slick with sweat, so no shower until later. Stiles smiles when he feels Jackson stroking his back and holding him tight, tightening his own grip on Jackson so he’ll know that Stiles doesn’t plan on letting go anytime soon.