RockStarPeach

Title: The First Time
Pairing: Jensen/Misha
Rating: Adult
Summary: High school AU. Jensen experiences a lot of his first times with Misha. Most of the ones that really stand out are firsts for them both. Featuring blushing virgin!Jensen and crossdressing!Misha.
A/N: Prequel to a story I wrote a while back, Another Thing To Fall, where Jensen and Misha’s relationship is tested when Jensen meets Jared.
Word count: 19800
Warnings: drug use, slight underage (fic starts when Jensen is 15, Misha is 17, no penetrative sex until they’re both over 18), underage use of alcohol

Previous


The first time Jensen thinks he’s going to actually die of embarrassment is on a Saturday afternoon in late August, almost a year after he first met Misha.

His parents sit him down to give him ‘the talk’, which would be horrifying enough on its own, but the fact that they do it when Misha’s there just pushes the whole experience those extra few notches past horrible and into mortifying.

Jensen’s in his bedroom with Misha, finishing off a package of Skittles and trying to decide what they want to do that night. Misha is lying on his bed with his hands behind his head and Jensen has his desk chair swivelled around to face him, feet kicked up on the mattress next to Misha and his toes are poking into Misha’s leg as he rocks himself slightly and tosses every other candy in the vague direction of Misha’s mouth.

Some of them even hit their target, but most are scattered around the pillow and the floor.

“Movie?” Jensen suggests and Misha winces as Jensen’s latest toss bounces off Misha’s tooth.

“We’ve seen everything,” Misha says, picks up one of the discarded candies and flicks it at Jensen, who just barely manages to duck out of the way and not catch it in his left eye. “A bunch of people are going over to Katie’s place later. Pool party, I think.”

It’s weird, Jensen thinks, that even though all Misha’s friends are really cool with him, and all his friends are really cool with Misha, that they don’t actually have any mutual friends, even after a year together. It’s not a problem, they always get enough time together and nobody ever feels awkward, it’s just… odd.

“Yeah, I guess,” Jensen shrugs, sticks his fingers into the Skittles bag to find it empty and then scrunches it up and tosses it in the garbage bin next to his desk. “You wanna grab some pizza on the way, or should I tell my parents we’re eating here?”

Misha opens his mouth to answer but he’s interrupted by a knock on Jensen’s door.

“Come in,” he calls and he frowns at the open doorway when both his parents walk in. They’re standing a little straighter than normal, their faces tight and their mouths in thin lines. For a few seconds Jensen thinks he’s in serious shit here, but try as he might, he can’t think of anything he’s done wrong lately.

He kicks his feet off the bed and sits up straight in the chair, darts a glance at Misha and watches while he sits up as well, folds one foot under the other leg and presses his back against the wall.

“Mom?” Jensen asks after thirty seconds have passed and nobody has spoken. “Dad? What’s going on?”

Jensen’s mom smiles crookedly at him, then Misha, and takes his dad’s arm to pull him next to her as she sits down on the bench seat under Jensen’s bedroom window. His dad stumbles a little, his hands clasped behind his back, but when he sits he’s forced to move them and Jensen sees that he’s holding something in one hand, and when Jensen squints he can just make out the silver embosses letters across the top of the box. TROJAN, it says, and with a sinking feeling in his gut Jensen realises his dad is holding a box of condoms.

Fucking shit.

“Relax, dear,” his mom tells him. “Nothing’s wrong. Your dad and I just wanted to talk to you. Both of you.”

“About?” Jensen’s stomach feels like it’s in his throat and he can’t keep his fingers from fidgeting with the cord his of mouse. He looks at Misha and he’s just sitting there, calm as you please. He almost looks like he’s smiling, the fucker.

“Jensen, Misha,” she starts, voice warm if slightly shaky as she works a steadying hand up and down Jensen’s dad’s thigh. “You two boys have been together a while now.”

“About a year, yes,” Misha answers for him, since Jensen just nods like a dumbass.

His mom shoots Misha a smile before turning back to Jensen.

“We want you to know that we know what it’s like to be kids. To be with someone you care for and not be able to keep your hands to yourselves.”

“Mom…” Jensen starts, shaking his head, but his mom cuts him off, ignoring him.

“We trust you. Both of you. You’re old enough to start making decisions for yourself about what’s best for you but we just want to make sure you know what you’re getting into. That you’re being safe.”

“Mom.”

“Wear these,” Jensen’s dad grudgingly spits out as he gets up from the bench and crosses to Jensen in three huge strides, placing the box of condoms in Jensen’s hand. Jensen takes them, stares down at them dumbly until his dad is sitting down next to his mom again. He blinks then and looks up at his parents in utter horror.

He thinks he might hear Misha actually snicker off to his side, but he doesn’t risk looking at him to check.

“Or make sure Misha wears them,” his mom says, “if that’s how it works out.”

“Mom!” Jensen shouts, tossing the condoms on his desk like they’re suddenly on fire.

Jensen’s dad just growls and gives Misha a glare that would send a lesser man running for the door, but Misha just raises his hands in mock surrender, lips curling up in a calm half-smile.

Jensen’s parents have been pretty cool about him liking guys right from the jump, but his dad still hasn’t been able to get over some deeply ingrained stereotypes. Jensen’s a man, albeit a young one and his dad has his own ideas about what that means. Never mind the fact that Misha’s also a man, a man two years older than Jensen, because Jensen is an Ackles boy and he has to pay for dinner and hold doors open and walk his date home and, apparently, be the one in the position to wear the condom during sex.

“We’re not having sex,” Jensen says desperately, looking from his parents to Misha and back again.

“I know that, sweetie,” his mom says. “But when you do, we want you to be prepared.”

“So uh…” his dad starts, clears his throat and starts again. “If you need to talk or… anything. We’re here, Jensen. We love you and we want you to know you don’t have to hide anything from us. That uh… goes for you too, Misha. You’re older, you’re probably more experienced and…”

“I would never ask Jensen to do something he’s not ready for,” Misha cuts him off, his tone sharp and his posture suddenly rigid.

“Of course you wouldn’t,” Jensen’s mom quickly assures him and Jensen groans and sinks deeper into his chair. If he hopes real hard, maybe it will swallow him up and spare him some humiliation.

Jensen’s dad gives Misha a tight smile and says, “I know that, son. That’s not what I meant. You’re both young. There’s no hurry. I’m sure it doesn’t feel that way right now to the two of you, but you’ve got plenty of time. And if you do want to… have sex, I just want you to be aware of the risks and the possible emotional and physical side effects.”

Misha nods and relaxes again and Jensen’s dad turns to Jensen once more.

“Sex can be great,” he says and Jensen can feel his face get so hot and flushed with blood that he thinks it might catch fire. “But it’s a serious thing. You need to be careful, you need to respect each other. I’m sure you know the risks – you’ve probably learnt all about it in health class – but if there’s anything else you need, either of you, we’re here. And if you don’t want to talk, that’s fine too. Just be safe, and make sure you know what you’re doing.”

“I…” Jensen starts, blinks and shakes his head. This cannot be happening. It just can’t.

“Thank you, Mr. Ackles,” Misha says, taking some of the heat off. “Mrs. Ackles. When we decide to take that step, it’ll be when we’re both ready.”

“Yeah,” Jensen says, finally joining the conversation. He knows if he doesn’t say something now his parents are just going to ambush him later. And they’ll probably think that Misha actually is pressuring him, or some bullshit. “We’ll be safe, dad. And we’ll think it through. But I swear, we’re not there yet. So can we just… stop talking about my non-existent sex life?”

“God yes,” his dad says on a harsh exhale and his parents stand together. Well, at least Jensen can take comfort in the fact that his dad hates this shit as much as he does. For one brief moment he sort of hopes that his mom and Misha get sick off some bad seafood so he can laugh at their pain, because they both seem to be way too comfortable with this sex talk.

“Will you boys be here for supper?” his mom asks, edging towards the door with his dad.

“Sure,” Jensen answers, not really paying attention. “Can Misha and I have a few minutes?”

“Supper will be in an hour,” his mom says, giving them each one last comforting smile before she shuts his bedroom door.

“Holy fuck, that was horrible,” Jensen says, tilts his head back and squeezes his eyes shut. Wish as he might, the world doesn’t reset to half an hour ago.

“It wasn’t so bad,” Misha tells him, reaches over to grab Jensen’s hand and tugs him towards the bed. Jensen goes willingly and ends up splayed out half on top of Misha with his face buried in Misha’s neck.

“I’m sorry, Misha. Seriously, they shouldn’t have put you through that.”

“I really didn’t mind,” Misha says.

“Yeah, I know. What the fuck is up with that? You should be even more freaked out than me. I thought my dad was gonna kick your ass for a minute there.”

Misha muffles his laugh against the side of Jensen’s head and kisses his temple.

“They care about you. They want what’s best for you. So do I. I understand where they’re coming from.”

“I’m your boyfriend, jackass,” Jensen snaps, biting down on Misha’s neck a little too hard in protest. “I’m not someone you have to look out for.”

“Of course you’re not. I know you can look out for yourself. I know you’d never do something just because someone else wanted it and I know that if I ever pushed you too far you’d kick my ass without thinking twice.”

That much is true. Jensen’s pretty steadfast in his life decisions and for all of Misha’s two extra years, Jensen’s got two inches on him in height and he’s definitely more muscular. They’ve never had a physical fight (Jensen’s never had one at all outside of football practice) but if they did, Jensen’s pretty sure he’d win.

“Yeah,” Jensen croaks, rolls so he’s on his back next to Misha. “Still, you think we can pretend this didn’t happen? Shit, I can’t believe my dad gave me condoms.”

“I noticed they were lubricated,” Misha says, and Jensen looks over at him a little slack-jawed. He didn’t know Misha was paying that much attention. As soon as Jensen figured out what was in the box, he couldn’t look away fast enough. “And ribbed. I think that’s pretty considerate.”

“Oh my God, you’re a freak,” Jensen groans. “Seriously, why do I even hang out with you?”

“Because I have an unusually large penis,” Misha answers, deadpan and Jensen nearly chokes on his tongue. “And because I adore you. It would be futile to fight me on this.”

“Yeah,” Jensen agrees. “I am pretty awesome. It’s probably easier on me to just keep letting you buy me pretty things and give me blow jobs.”

“Speaking of sex,” Misha says, even though Jensen hadn’t actually mentioned sex. “We’ve got an hour to kill and a whole box of condoms…”

“Not a chance,” Jensen says, cutting Misha off with a short shake of his head. He pushes himself up to sitting and smacks his open palm across Misha’s hip. “After that, I don’t think we can even make out in this house anymore.”

“Prude,” Misha pouts and Jensen has to fight not to lean forward and take Misha’s bottom lip between his teeth. Huh. Turns out a sex talk from his parents isn’t a total boner-kill after all.

“Whatever,” Jensen says and forces himself up off the bed. “So Katie’s tonight? Think you’ll be able to keep it in your pants with me all wet and shirtless?” he teases, before digging through his dresser for his swim shorts.

“You may be nearly irresistible,” Misha tells him, sitting up and watching Jensen’s ass as he bends over to look in the bottom drawer, “but wait until you see me in a bikini. It might be you who has a hard time restraining himself.”

Jensen just blinks at him and hopes to God he’s not serious before he flips on his television and they watch the second half of an old Bonanza rerun.

Turns out, Misha does have a bikini. And he wears it, without any shame at all.

It’s tiny and red and it looks so fucking ridiculous that it shouldn’t make Jensen as hard as it does. He spends the first hour of the party sitting in a chair on the pool deck watching Misha swim and trying to hide his erection and it’s not until he excuses himself and jerks off in the bathroom that he can actually manage to get into the pool without outing himself as a complete pervert.

He makes Misha pull his car over to the side of a back road on their way back to Jensen’s after so Jensen can blow him right there in the car.

Despite the incredibly awkward start, the day ends on a high note.

***

The first time someone tells Jensen that they love him (someone outside of his immediate family anyway) is at about three o’clock in the morning on a Sunday.

It’s two weeks after the Saturday afternoon that shall not be mentioned and his parents are away for the weekend. Misha’s spending the night; he’s allowed to do that, now. In fact, if Misha didn’t agree to stay with Jensen, his parents probably wouldn’t have left him home by himself. Which is stupid, because yes, fine, Jensen is only sixteen years old, but Misha’s only a year and half older, so it’s not like anything that could go wrong just magically won’t with him around.

He has to admit though, he does feel better not being on his own and his parents probably know that, so he’s not really going to protest. And getting to spend the night, the whole night, with his boyfriend, three nights in a row, is pretty damn awesome. Especially since in just two days he’s not going to be seeing much of Misha at all.

School is starting up on Tuesday. Jensen’s going into his junior year and Misha is leaving Monday, moving into the dorms at Ohio State. Because Misha pulled Columbus out of a hat. Seriously. One university is as good as the next, he figures and he wants to get out of the house but not go too far away.

Jensen doesn’t want him to go, he’ll miss him of course, but he gets it. It’s not like it’s so far that they’ll never see each other (Misha’s promised to come home to visit at least once a month) and they can talk on the phone all the time, but there’s still a selfish part of Jensen that wants to lock him up in his bedroom and never let him go.

Jensen doesn’t even realise he’s been staring at the ceiling instead of the television until the sound suddenly quiets and the room goes black.

“What’s up?” Misha asks him, putting the remote down on the table before rolling onto his side and throwing a leg over one of Jensen’s. Jensen’s bed is a twin, so it’s a tight fit, but they don’t mind. “You haven’t even once commented on the magnificence that is George Clooney’s ass and you didn’t seem to notice when I jerked off to the shirtless scene.”

“You did what?” Jensen asks, pushing up on his elbows as he looks Misha up and down. He doesn’t look rumpled or mussed at all and when Jensen’s gaze lands on Misha’s face in the dark he’s smirking. Bastard. “Screw you.”

“Seriously,” Misha says, smile fading as he pushes Jensen back down and leans over him. He kisses him, brief press of lips that slowly gets closer, more intimate, lets his tongue slide out over Jensen’s and by the time he pulls back Jensen is panting and dizzy. “Is something wrong?”

“Nah,” Jensen tells him, because really, it’s nothing. Nothing they haven’t talked about already and there’s nothing they can do about it, anyway. “I’m just thinking about how much I’m gonna miss you.”

“You won’t even notice I’m gone,” Misha says and Jensen snorts at that and rolls his eyes. As if.

“Let’s not talk about it. We still have tonight and tomorrow night, and that kissing was pretty damn good, so you think we could maybe get back to that, instead?”

Misha laughs then, a low, deep chuckle that vibrates through his body and into Jensen’s and Jensen doesn’t bother suppressing his shiver, doesn’t hide the way the sound always goes right to his cock.

“I think that can be arranged,” Misha says and leans over him again, presses their lips together.

It’s nice then. Warm and a little sloppy and Jensen’s getting so tired that it’s all kind of a fuzzy haze and he sort of never, ever wants it to stop. His hand finds its way down the front of Misha’s blue flannel pants and his fingers wrap around the hard shaft they find there, pump up and down a few times until the tip gets slick and Jensen spreads the wetness around with the palm of his hand.

Misha moans into his ear, lets out these tiny little gasps as he rocks into Jensen’s hand and it’s only then that Jensen feels Misha’s hand cupping his aching erection through the thin cotton of his sleep shorts.

“Oh God,” Misha pants, bucks once sharply and squeezes Jensen’s cock so hard it almost hurts. “Oh, God, Jensen.”

“Mmmm,” Jensen agrees, wriggles his own hips forward to try to settle more firmly in Misha’s grasp but Misha just pressed his palm forward, mashing Jensen’s cock up against his belly and then lets go. He grabs Jensen’s wrist instead, stops the movements of his fist up and down and it takes a few seconds for his breathing to get under control.

A few seconds that, Jensen’s not gonna lie, make him a little nervous.

“You know,” Misha says, going for his typical calm, cool and collected, but missing the mark by an enormous margin, “we do have those condoms. And if I recall, your dad did give me permission to fuck you.”

Jensen takes his hand out of Misha’s pants and laughs a shaky laugh.

“Did you see his face? I’m pretty sure any permission he gave was for me to do the fucking. And even that was pretty grudging.”

Misha lifts his hand then, places it on Jensen’s cheek. He looks into Jensen’s eyes with so much honest affection and intensity and suddenly it’s not even a little bit funny anymore.

“I’m good either way,” Misha tells him seriously and Jensen swallows down around the lump in his throat. He honestly hadn’t expected this to come up tonight. Maybe he was being naïve, but he’d thought Misha wanted to wait, too. He really should have known better. Misha’s eighteen, he’s starting college in two days and they’ve got the house to themselves for another thirty-six hours or so. Of course he wants to get laid.

“I’m… I’m not,” Jensen finally says, the words coming out cracked and quiet. “Sorry, baby. I’m really sorry. I know you’ve been waiting a long time, but…”

“Hey,” Misha says sharply, cutting off what could possibly turn into some idiotic babbling. “It’s okay. I mean it. I haven’t actually been waiting that long. I wasn’t ready at first either. I am now, but if you’re still not… Jensen, I get that. And honestly, you should know that about me.”

“I do,” Jensen tells him fiercely, his hand moving to Misha’s hip and gripping tight. “Of course I do.”

And he does. He knows Misha isn’t going to get fed up and leave him because Jensen doesn’t put out. Misha’s not that guy, never has been. And now Jensen feels totally awkward, he’s ruined the mood and here they are, in bed together with half-wilted erections and he doesn’t know if he should try to go back to the touching or if he should just call it a night.

“So,” he starts, relaxing his grip on Misha’s hip to rub his hand over his thigh. “You wanna just go to sleep then, or…”

“I love you,” Misha tells him, completely out of the blue and Jensen freezes. His hand stills on Misha’s leg and his eyes open wide, every muscle tensed as he holds his breath, ready to hightail it out of there. This is new. This is something he saw coming even less than the request for sex.

“Don’t freak out,” Misha goes on, smiling softly as he places a kiss to the corner of Jensen’s tense mouth. “I’m not just saying it to hear it back, or to get into your pants, though both would be nice.” He pauses for a moment while Jensen lets out a short burst of laughter before he continues. “I’m saying it because it’s true. It’s been true for months. I love you, Jensen. I fell in love with you a long time ago and I was right; it was easy.”

Jensen honestly has no idea what to make of that, except for the vague notion he’s got of throwing Misha down on the bed and kissing him until they both pass out. He doesn’t though, which is probably a good thing.

“If it’s been so long,” he asks, instead, “why’d you wait until now to tell me?”

Misha just closes his eyes for a moment, opens them and looks over at Jensen with an easy grin.

“The same reason you’re still waiting to tell me,” he says and Jensen frowns.

“What makes you think I love you?”

“I didn’t say you did,” Misha doesn’t quite answer and Jensen decides that a monster make-out session ending in mutual hand jobs is a better way to spend their second last night together than arguing semantics over feelings.

When Misha pulls out of Jensen’s driveway at 4 o’clock Monday afternoon with a car full of clothes, books, movies and a mismatched set of dishes, there’s an unsettled feeling in Jensen’s stomach he can’t quite identify.

NEXT