Top 5 bottom!Dean headcanon ?
He only bottoms for Sam. Okay, so it’s not like Dean hasn’t had sex with other guys; he and Sam have definitely had their share of issues over the last decade or so, and Dean is only human. He likes sex, and he’s never been particularly picky about who he has it with. But bottoming for someone? It’s personal. Letting someone at his unprotected back or spreading his legs for them, it takes a certain amount of trust. Without the trust, the entire process is pretty fucking unpleasant. He knows; he’s tried it before.
The first time goes something like this: They’re in some moldy motel room just off the New Jersey turnpike, the thruway so close that all the windows shake every time an eighteen wheeler goes by. Dad’s passed out in the other bed, snoring so loudly he’s giving the eighteen wheelers a run for their money, and Dean is fucking horny. It’s just about three in the morning. Sam’s practically radiating heat behind him, and the last time they swapped hand jobs was fucking Tennessee. They hadn’t yet established whether dry humping when one of them is asleep is acceptable practice, but Dean’s seriously considering doing it anyway. Except when he goes to turn and face Sam, Sam is right behind him, and all he ends up doing is grinding his ass against Sam’s crotch and elbowing him in the side. Sam grunts and mumbles something that could be ‘what the fuck,’ his heavy exhale brushing the hairs on Dean’s neck. There’s a few moments of absolute silence where Dean can feel every inch of Sam’s cock pressing against him through two layers of flannel, then Sam thrusts his hips forward, his hand latching on to Dean’s hip bone, and they’re off.
They’ve done it like that before, although their positions were always reversed, Dean grinding against Sam’s ass until they both come in their shorts. But when Sam hooks his fingers on the waist of Dean’s boxers and pulls them down, Dean squirms out of them without a word. Sam’s cock is hot against his skin, pushing in between his thighs, and Dean doesn’t think about where this is going or what it means, he just knows he’s so fucking hard it hurts. He can’t work his own cock the way he wants to, not if they’re trying to be quiet, so he’s reduced to shifting and squirming until he can get Sam’s cock somewhere where it’ll get him off. Except the next thing he knows, Sam’s cock is pressing against his hole, pushing inside of him with nothing but pre-come to smooth the way, and it fucking hurts but it feels so good he feels like he’s gonna lose his damn mind. He cries out, forgetting they’re trying to be quiet, and Sam’s hand clamps tightly over his mouth. The snoring stops; they both freeze again, holding their breaths. The head of Sam’s cock is buried in Dean’s ass, painfully stretching him open, his fingers digging into Dean’s jaw. Dad shifts and grunts, as if he’s about to get up, and with startling clarity, Dean can see exactly what happens next. Dad sitting up, turning the light on, and seeing Dean impaled on his brother’s cock, puddle of pre-come underneath him, panting into Sam’s hand. He comes so hard he blacks out for a moment, mewling into Sam’s palm. From somewhere far away he can hear Sam swearing softly into his neck, can feel Sam’s cock twitching and spilling inside of him, but it’s all secondary to the aftershock thrumming through his body. He only knows that he wants to do that again.
After that Sam does research. He buys lube and condoms. He fucks Dean with his tongue and his fingers. They don’t talk about it because they’ve never talked about swapping hand jobs either, but Dean does plenty of talking when they’re going at it because Sam won’t have it any other way. If Dean wants Sam’s tongue in his ass, he has to ask for it; he has to beg for each finger individually, until he’s writing on all four and begging for cock. Sam never says no; not even when Dean wants it with nothing but spit for prep, hard and fast and painful, so he can’t sit down for days. All Dean has to do is ask.
His favorite position is sitting in Sam’s lap, back arched like a bow and hips grinding back slowly, his face hidden under Sam’s jaw. Sam knows to wrap one hand around Dean’s throat and slow his thrusts until they border on torture, until Dean is sobbing for release. It’s a vulnerable position; impaled to the hilt, knees splayed wide, Sam’s arm wrapped around his waist. Each time feels like that first time, Sam’s solid weight at his back, Sam’s hand trapping his head in place, feeling so full it verges on painful. He imagines someone walking in on them, seeing him spread open and begging, trapped in place and unable to move, and it pushes him over the edge each time.