359 - relationships - Sweet Sixteen (Never Been Kissed) - alakewood - Supernatural

[alakewood.livejournal.com]

Title: Sweet Sixteen (Never Been Kissed)
Fandom: Supernatural
Prompt: 359 – relationships
Warning: Pre-series. Underage Wincest. Mentions of past Dean/OFC.
Rating: NC-17 overall.
Word Count: ~2200
Summary: Based on this prompt from the spnkink_meme. Sam looses his virginity to Dean in the Impala.
Disclaimer: As always, I own nothing.

oxoxo

Sam stands from the library steps when he hears the rumble of the Impala's engine down the block.

“Don't know why you're bothering,” Dean says as soon as Sam climbs into the car, dropping his backpack at his feet.

Sam rolls down his window in an attempt to dissipate the smell of grease, cigarette smoke, and cheap perfume when Dean pulls away from the curb. “I've got a project due Friday that's worth half of my grade for the semester,” Sam tells him. “Whatever school I end up at next is gonna get my transcripts and-”

“I get it,” Dean interrupts loudly, throwing on the blinker to turn onto the main street that becomes the highway that'll take them out of town to the ramshackle house they've been staying in for the past two months their dad's been off chasing something with a hunting ground that covers the whole eastern half of the state. “Jeez. You're such a nerd, Sammy. You need to get out and live a little instead of spending all your free time at the freaking library.”

“What?” Sam starts with a sneer. “Like you?”

Dean grins. “Hell yeah, Sammy! Like last Saturday. This hot, little blonde that'd been coming into the bar all week, wearin' this short, little skirt and a low-cut top.” He sighs and glances over at Sam in the waning daylight as the sun slowly sinks to the horizon in the west. “She'd been droppin' hints, finally worked up the courage to talk to me, asked me to go back to her place. Hell, we didn't even make it out of the parking lot. Took her right up against that door.” He tilts his chin towards Sam.

Sam glances at his door and shifts a little in his seat, feeling his body respond to the mental picture of Dean having sex with some girl right there. “Yeah, well, maybe I had plans with a girl,” he finally says, not looking at his brother.

Dean sits up a little straighter. “Yeah?”

“Yeah. I asked Alyssa Healy to the homecoming dance this weekend, but...”

“Alyssa,” Dean repeats. “Is she that the redhead that's been coming over lately?”

Sam nods. “I've been tutoring her.”

Dean cackles. “Is that what you crazy kids are calling it?”

“No,” Sam says quickly. “We weren't doing... that.” He flushes, feels himself get even harder in his pants at the thought of what Dean's implying. It's not like he hasn't imagined it – actually thought that, maybe, after the dance... Well, he hoped he'd at least get to kiss her.

“So, you were going to take her to the dance?”

“Yeah. But we're leaving Friday, so.” Sam shrugs. “Doesn't even matter.”

He must give something away in his voice because Dean's laughing again. “Poor Sammy. Did Dad cockblock you?” A glance over at Sam gives him his answer. “He totally did!” Dean crows.

It's not like their life and the constant moving lends to enough time to build friendships, much less relationships. “I just- I wanted to get it over with. And now-”

“Whoa,” Dean says, looking at Sam as he slows down to turn onto the county road that leads to their driveway. “Are you saying that you've never had sex?”

“Haven't had sex,” Sam confirms frustratedly. “Haven't even kissed a girl. In case you haven't noticed, I'm not like you. Like, at all.”

“Aw, Sammy.” They're still a good five or so miles from their two-story, two-bedroom house when Dean pulls over onto the side of the road where a rutted track leads into an overgrown pasture. “There's nothing wrong with being a virgin. And not being like me isn't exactly a bad thing.”

Sam huffs a breath and slouches down in his seat. “Whatever. I just wish I could get it out of the way. Not like it's a big deal or anything, right?”

“It can be,” Dean tells him, feeling slightly uncomfortable and out of his element. “It never was for me, but sometimes it's better to wait until you're in love with somebody before you have sex.”

Sam snorts at that. “Yeah. 'Cause I'm gonna get a girl to fall in love with me in the week or a month that I know her.”

“I could always help you out, you know,” Dean says, turning in his seat.

“Help me-” Sam's not sure if Dean's offering what it sounds like he's offering or not. Yeah, he loves and trusts his brother, but... to let Dean do that. “You would-”

“What?” Dean suddenly seems to hear how what he said sounds a proposition. “No, that's- that's not what I meant. I could introduce you to a girl or something.”

Oddly, Sam's not entirely opposed to the thought of letting Dean help him out. And his first time would be with somebody he loves. “Would you, though?”

“Introduce you to a girl? Yeah. Absolutely.”

“No. Would you, you know... have sex... with me?”

“Sam. No. We can't. We're brothers.” There's no way Sam knows what he's even asking for. “We can't.”

“It's not like it'd mean anything. I just. I want to get it over with.”

Dean shakes his head, can't believe Sam's serious about this. “Even if I... Even if I said yes, it's not like we've got anything to, you know, do it.”

“There's gun oil in the trunk,” Sam argues.

“Sam-”

“Please? Come on.” Now that the idea's in his head, he's kind of committed to it.

Shaking his head again, Dean sighs. “And how would we... Who would... Somebody's gotta take it.”

“Oh,” Sam says. He hadn't quite thought of that. But the way Dean says it makes it pretty clear to Sam that he doesn't want to be the one taking it. “I could, I guess.”

“Sam,” Dean says again.

“Yeah. Come on. Let's just.” He throws off his seatbelt and gets out, climbing into the backseat. “Get the gun oil,” he tells Dean as he starts on the fly of his jeans. He looks up at his brother as the dome light slowly dims. “What are you waiting for?”

“To wake up from this crazy-ass dream,” Dean says to himself. Before Sam can ask him to hurry up, he climbs out of the car and pops the trunk, easily finding the gun oil. He can't believe he's going to do this. Sam's sitting in the backseat in his underwear when Dean climbs in beside him. “Are you sure you want to do this?”

“Yeah,” Sam nods. “How should we...?”

“Um... I don't know. Maybe if you got on your knees...”

“Okay.” Sam shifts into position, ducking his head down and sitting on his knees.

“And you need to... you know. Take off your underwear.”

“Oh, yeah, right.” He awkwardly shimmies out of his briefs, embarrassed that he's half-naked in the backseat of the Impala with his ass practically in Dean's face. “What now?”

“I guess I should...” Dean makes a face, wrinkles his nose, “finger you open.” He uncaps the bottle of gun oil and coats his fingers liberally, hesitantly pressing one against Sam's hole.

Sam jerks away from the touch before taking a deep breath and trying to settle down. “Sorry. Kind of wasn't expecting that.”

“We don't have to.”

“I want to. I'm ready. Do it again.” Sam holds still as Dean slowly pushes a finger into him. It's weird and uncomfortable but Sam closes his eyes and imagines doing this to Alyssa or another girl, pushing his fingers into her, getting her ready to take him.

Dean works Sam open, gets a second then a third finger into him, finds that bundle of nerves buried deep that makes Sam's thighs spasm. “Is that okay?”

“Yeah,” Sam gasps, nodding, pressing back onto Dean's fingers because, yep, that's definitely okay. Better than.

“You ready for me?”

“Uh huh.”

Dean pulls his fingers free and wipes them on the leg of his jeans before digging his wallet out of his back pocket and fumbling for the condom he keeps inside it. He works his belt and fly open, gets his pants and boxer-briefs down his thighs before taking himself in hand, thinking about Tanya and how tight and wet she was to get himself hard. He tears the condom packet open and rolls it down his dick, slicks the latex up with more gun oil before kneeling up behind Sam. “Okay. I'm gonna.”

“Okay.” Sam braces himself on his shaking arms and tries to relax when he feels the hot, slick blunt head of Dean's dick press into him. He grits his teeth against the pain and keeps breathing deep. The burn is nothing compared to the time he was attacked by that ghoul last summer. When he can feel Dean's thighs against the back of his own, he shifts experimentally, flexes his muscles around Dean.

“Fuck,” Dean grunts, feeling Sam clamp down on his dick. “Christ, Sammy.”

“Sorry, just...” He circles his hips and rocks forward, back, electricity zinging up his spine as Dean's dick glances across that place inside him Dean's fingers found.

Dean grips Sam's hips because, “Jesus,” that feels so much better than it should. Almost too tight and... He thrusts back in tentatively, listening to the ragged breath he pushes out of Sam. “Tell me- tell me if you need me to- to stop. Okay?”

“Yeah,” Sam nods vigorously. “Keep going. Keep going.”

Dean sets up a slow rhythm that Sam quickly matches, arching his spine and rocking back into Dean's hips. God, he shouldn't be doing this. Shouldn't be doing this. But he can't stop, now.

Sam's orgasm catches him by surprise, stripes the vinyl of the seat with thick, milky ropes of come as he bites his bottom lip bloody.

The feel of Sam's muscles rippling around his dick sends Dean right over the edge after his brother embarrassingly quickly. Sam's shuddering under his hands while Dean pumps the condom full of jizz. When he pulls out, carefully holding onto the condom, Sam collapses onto the seat and what they just did – what he just let happen – hits Dean harder than his orgasm. The sight of the shiny, puffy rim of Sam's hole is like an accusation. He never should've let it get this far. “Sam,” Dean says, sitting back on his knees, folding his hands in his lap to keep from touching his brother.

“Hmm?” He doesn't want to move yet, bones still feeling like jelly from the rush of heat that burned through him.

“You okay?”

“Uh huh. Great.”

“You sure?”

The uncertainty in Dean's voice finally forces Sam to move. He sits up and looks over at Dean. “I'm good.”

Dean shakes his head. “I shouldn't've-”

“Hey. I asked you to. I wanted it.”

“Still. I never should have let it happen.”

“Dude,” Sam sighs. “It was good. I liked it.” He can see the guilt on his brother's face, doesn't know what else to say to convince him. “It's not like it's gonna happen again. I wanted to get the whole sex thing over with and I did. So it's fine. Okay?”

Dean shrugs a shoulder and glances up at Sam before pulling up his pants.

“I'm not gonna... ask you to hold my hand and go steady or anything, jeez. It was a one-time thing.”

Dean cracks a half-smile at that. “Whatever.” He tilts his chin towards Sam. “You're cleaning that up.”

Sam glances at the drying smear of come on the seat and wrinkles his nose, swiping at the mess with his underwear. “Yeah, tomorrow.”

“You better.” He shoves open the door and does up his fly, buckles his belt, then climbs back into the driver's seat

Sam pulls his jeans back on and slides his feet into his shoes before joining Dean back up front. He looks at Dean out of the corner of his eye when he sits up straighter and feels the ache inside him, little shocks of pleasure trembling in his belly that only intensify with the rumble of the engine when Dean starts up the car. He's glad to have gotten that over with. Of course, having sex with a girl is going to be a whole lot different. But now he kind of knows what to expect. Well, not really. If he were a girl he'd maybe kind of know what to expect.

“We've still got pizzas in the freezer, don't we?” Dean asks as he pulls out onto the road.

“Yeah. Sausage and pepperoni, I think.”

“Awesome. I'm starving.”

Sam's stomach grumbles. “Me, too.”

Dean laughs and reaches for the volume knob on the radio, cranking up Skynyrd. And just like that, things are back to normal.

Well, mostly.