I'm really in awe of someone who has the courage to make this post at all!
About the second "friend".
I have a really good male friend. His childhood was kind of like mine. We each live in a similar version of reality and have an unspoken agreement to not talk about it.
He jokes about being a "sex addict",. I suspect that he thinks, somewhere deep inside, that sex is what people REALLY value him for, no matter what they say. I suspect I'm the only female he's ever been close to who HASN'T had sex with him. Not for want of temptation and there've been a couple close calls. The last time, he was engaged to someone I really like and who's been good for him. I (eventually) told him that I wasn't going to help him wreck a great relationship even if he didn't have the sense to see that that was what he was doing. I wasn't sure what to expect. We are closer friends now that ever. Maybe because he figured out that what I value is HIM, as a person. Anyway, THAT is friendship, IMO. Not exactly the same thing. Not "punishment". But the whole situation is complicated and the best thing you can do is not go there. If, after the dust settles and you're in a better frame of mind, you STILL think it's a good idea, you can always go ahead with what ever you want. Just YOU make the decision your own self. Don't let a symptom make it for you. (Thinking of you and hoping for the very best!)