Wincest (for the headcanons thing)
CAN I DO WHAT IS AND WHAT SHOULD NEVER BE ALT UNIVERSE WINCEST BECAUSE I JUST FINISHED WATCHING WIAWSNB AND THE TRAGIC UNRESOLVED WINCEST POTENTIAL IS STRONG IN THIS ONE
what was their first kiss like | they never had one, but dean always thought about the opportunity he missed to kiss sam even once before sam left for stanford, and he regrets not having done it—he figures he pushed sam away enough as it is, so making a move couldn’t have made it any worse
where were they their first time having sex | for a long time, sam was all twisted up about seeing himself in a sexual light because he almost exclusively had thoughts about his brother and it made him feel guilty as hell. it took him a while to sort of realize that was just how it was going to be, and try to ignore it instead of beating himself up. he had his first time his freshman year of college, with a girl he chanced to meet because he sat next to her during orientation, as you do. a little later in the year he ended up running into her at a party that he got dragged to by some floor-mates. her name was deirdre, and she went by dee for short, and sam doesn’t like to reflect on that much. (as for dean, he channeled his feelings for sam into lots of casual sex, but he always worried that sam had somehow known anyway and that he’d left for stanford because of it.)
who’s louder | nothing complicated about this one. sam is louder during sex, but dean can be loud jerking off, and in the months leading up to leaving for college sam thought it was gonna drive him insane. (after he got to school, he realized that overhearing dean touching himself, no matter how much inner turmoil it caused him, was still infinitely preferable to overhearing his suitemate having sex)
who wakes up first | he’d never admit it, but if he were ever given the chance dean would give anything to wake up next to sam and stay in bed instead of getting up. he knows it’s just a desperate fiction, and he scoffs at himself for how sappy it is, because sam’s always been an early riser anyway
who performs/receives oral more often | they’ve both thought about it
who tries new things more often | dean. he tells himself he’s just adventurous, but it’s more that it sort of fills the void, and it’s really a cycle of “what would sam think of this? fuck it, i’ve done too much shit wrong already for sam to bother knowing me; why stop here?”
if they had to choose a third+ person to include who would they include | having each other would be enough, but their lives have already unfolded in a way that that’s not going to happen, and they both know it, so they don’t torture themselves thinking on this more than they have to
