Going Out For Forbidden Sex

I have a high school friend who is a habitual one night stand girl. She has three or four bars she goes to, gets picked up and goes home the next day, or when she is thrown out. The more humiliating the sex the better, she's not a whore for money so she will go if the guy picks her up regardless, but she also whores herself for money. She wants to be my friend but I find her whoring around impossible to tolerate or understand.

A friend of mind, my confidant and mentor, says she has very low self esteem. But that is not my problem, don't go out with her, that's about all I can do. What I didn't tell him is that I've been out with her a couple of times and she made arrangements for a two girls one boy experience. The two girls were us and we had sex while he decided on which one, and he grabs one of us to fuck and the other one is there to suck his dick when he's done.

I have this professional reputation at work and especially with my mentor. He has no idea that I have girl sex with her and much less that I've gone on a whore date with her. We don't care about the money, actually we've left the money on the counter of a diner for a woman who obviously could use a hundred. In my book we aren't whores, but I'm sure that's not how anyone else looks at it. If in the world someone close to me found out, I would be terribly embarrassed and disappointed, but if my mentor found out I'd be undone.