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 ONEÂ
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 itâhe figures he pushed sam away enough as it is, so making a move couldnât have made it any worseÂ
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 doesnât 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 heâd left for stanford because of it.)Â
whoâs 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 | heâd 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 itâs just a desperate fiction, and he scoffs at himself for how sappy it is, because samâs always been an early riser anyway
who performs/receives oral more often | theyâve both thought about it
who tries new things more often | dean. he tells himself heâs just adventurous, but itâs more that it sort of fills the void, and itâs really a cycle of âwhat would sam think of this? fuck it, iâve done too much shit wrong already for sam to bother knowing me; why stop here?âÂ
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 thatâs not going to happen, and they both know it, so they donât torture themselves thinking on this more than they have toÂ

















