Jack experimenting with boys, bringing them back to the bunker in the middle of the night - -
Sam and Dean have no idea until they walk in on him getting eaten out.

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Jack experimenting with boys, bringing them back to the bunker in the middle of the night - -
Sam and Dean have no idea until they walk in on him getting eaten out.
One thing Dean doesn't expect to walk in on is Jack getting rimmed by one of the apocalypse hunters.
Jack loses his virginity to some apocalypse world rando, and honestly - -
Sam and Dean don’t like that.
Not one bit.
Jack gave his virginity to one of apocalypse world people, and he's goddamn upset about it.
what about a v dark version of dean pimping out jack - the first time jack does it willingly (after dean talks him into it, but jack would do anything for dean) but hes so loud and squirms so much dean knows they wont make shit that way, so he eventually starts drugging jack before customers, not enough to knock him out, but enough that he just lays there and moans a little, eyes glossed over while he gets roughly stuffed full of burly trucker dick
Oh, fuck.
They're gonna wreck him.
ok but jack tied face down to a bed, duct tape over his mouth, his hole gaping so wide with some of the several loads that have been fucked into him oozing out and down his taint onto the bed
JESUS, ANON. HNG.
Dean would still protect him, if they try anything Jack would not like, he immediately threatens them and if they try to do it again, it’s a quick punch to the face. When they get back home, Dean fingers the come out of Jack’s sore hole and gives him warm bath, then makes sure to cuddle him and telling him how he’s so good.
OH, GOSH.
ok but jack tied up and gagged with his ass through a hole in a wall as a free hole for use and he just gets stuffed with big dick after big dick and all he can do is just sit there and take it
*YELLS*