Sex worker!Dean opens up so many options in headcanons and it would explain how he managed to always get gas money in canon besides ya know gambling and doing scams.
Like imagine Dean in one of the roadhouses and the other hunters knowing what Dean does as a side hustle to get money and one of the fat, burley hunters that looks like John fucks Dean behind the roadhouse
ugggh yeah. yeah! bcuz like it doesn't make a whole lot of sense getting a majority of their money from hustling, scams, gambling, and some odd jobs here and there. they need money for those motel rooms and food and clothes and especially fucking gas omg the impala HAS to be a gas guzzler
and i think dean wouldn't necessarily feel ashamed of it but would also definitely try to hide it from sam, and from john if john doesn't know. but he and sammy gotta eat and john will sometimes leave him with only a few twenties for a week. and fuck, you know what maybe he DOES want to get sam that comic book, and he DOES want to get that 12 pack of soda that they technically don't need. so the money has to come from somewhere and robbing is riskier (though he'll do that too from time to time) so sex work it is
but besides from all of that, i think sw!dean is so interesting to me bcuz i think he would have so many conflicting feelings over it and it'd be a big secret to keep from sam (and again, john if he knows). and thinking about either or both of them finding out in one way or another and imagining the fallout is sooooo </3 uWu ya know
