Well, he's not really an escort anymore, he used to escort. I met him on rentmen several years ago, and we've become good friends. He has a job now that is not relating to escorting, but he's bad at managing his money, he spends more money than he should in clothes, out with friends, drinking, etc. So he has a lot of debts now... He's young around 24ish (I'm early 40s). At the moment he doesn't feel comfortable living with his family anymore, he lives with them a few days every couple of weeks, because his job takes him around the country, and he goes back home very couple of weeks. He wants to turn his life around and start fresh. Start making good decisions, taking better care of his money, start saving, quit drinking, going to parties that often, etc. He's a very good guy, good person, honest. I think we have a good connection.
I'm live by myself, but I always have travelers visiting, family, friends, etc. So I wouldn't have a problem with him staying with me. I don't plan on charging him rent... at least not for a few months... while he starts saving and turning his life around. I wouldn't see him as a roommate really, more like a friend that I'm willing to help for a while... Eventually my goal would be to guide him and teach him a little about money management, so he can afford to move to a place on his own, or rent with someone else.
Has anyone been in this situation before? How do you handle it? What about sex? I wouldn't feel comfortable initiating sex with him... since I won't be paying him anymore...
Edit: The fact that he'll be around only on weekends at most, makes this situation something I'm willing to do. I think having a regular roommate situation where he's at home everyday, is not something that I can do for a long time (a few weeks at best).