Yes, and I've seen a number of fics that I wouldn't really classify as "hookerfics" but in which Dean turns the occasional trick to help them get by and it seems more plausible than Sam doing it. Dean's the one who's always been about doing anything for his family, and given the way Dean in canon has such a skewed idea of his own worth, it seems to make sense that he wouldn't consider himself above whoring himself to make a few bucks.