The first time they fuck, Sam's not a virgin, but he's never been with a guy before.
Dean has, though he doesn't exactly admit it, his experience is evidence enough. He guides Sam through it in a way that manages to be both filthy and informative - yeah, like that, spread your fingers, fuck, gimme another one, curl them, oh God Sammy. Sam doesn't question how easy Dean takes it. He doesn't have any baseline to measure it against. Dean barely needs any prep most days because he's that eager for it, even though Sam's proportionally big enough that Dean sobs his way through sex half the time, all while insisting he likes it, loves it, loves the way Sam splits him in two and leaves him hollow and aching afterwards.
It isn't until they reunite after years apart that he realises something wasn't right about how easy it had been for Dean to take Sam's cock.
The first time after a long time, Dean squirms and pants and winces his way from start to finish. They barely bothered with prep before, usually because they were short on time or just that desperate for each other, and this time is no different. Sam slicks himself up and drives his cock into his brother and for the first time ever, it's hard getting into him. It's a fight for every inch, and Sam feels like Dean's gonna cut off the circulation to his cock. Dean goes soft before Sam coaxes him back to hardness and that has never happened before. Dean whines about how it feels like Sam is shoving a baseball bat inside him, and this time, the tears aren't good ones. They barely manage to finish, and afterwards, Dean lays there trembling.
"Been a while," Dean says by way of explanation that only raises more questions.
"Who were you screwing, back then?" Sam asks later.
Dean lifts his head up from where it's pillowed on Sam's chest. Two weeks later and Dean takes it a lot easier now. He just proved how back in the saddle he is by riding Sam like some demented incubus cowboy.
"When we first started fucking. Who was he?"
Dean looks confused, and then that blank expression Sam remembers from when they were young shutters his eyes, and then that falsely light-hearted, joking look replaces it.
"Nobody. Why, you getting territorial?" he teases, but his voice has a nervous edge to it.
Sam can't stop thinking about it. Even when they didn't get a chance to fuck for weeks because Dad was always around, always needed Dean for something, always had his attention, every time they fucked it was like Dean was already ready for it, like he'd--
Like he'd just been fucked.
But the only other person Dean was every around was Dad. He barely left Dad's side. If they went drinking, they went together and returned together. They hunted together. They did the damn groceries together. They were always together.
When the hell did Dean find time for a secret boyfriend? Or even casual hookups?
It isn't until they find Dad again that it clicks. The way they rush into each other's arms, the tearful way they look at each other, the way Sam swears they're about to kiss but Dad's eyes flick to Sam and suddenly they're pulling apart.
He's wrong. He has to be wrong.
Then Dad's leaving again, so quickly after their reunion. As they're saying their goodbyes, he sees the dark marks left by Sam's mouth on Dean's throat and he touches his fingers to them, eyes going dark as his expression becomes something almost terrifying.
"War wounds," Dean tries to dismiss.
Dad locks his eyes with Dean.
"Don't lie to me, boy." His eyes snap to Sam. "I need to talk to your brother."
Then they're driving off and Sam's left holding the keys to the impala and questioning is own sanity. He questions it right until the moment Dean returns to their room, and Sam knows the shape of the bite marks covering the bruises he left on Dean's throat.
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