I think we can entertain each other in this sub by telling stories about our casual sex lives. (Also, I'd like to see other kinds of discussions than "advice for men for getting laid". So here's one.)

So let's tell stories about charity sex. That is, having sex with somebody who you wouldn't normally have sex with, just to help them out. Have you done it? Was it a good idea? Was it helpful? Or did it backfire? Would you do it?

My story... I met a guy on OkCupid, I don't remember who messaged first. Physically, he's not my type, but whatever, he reminds me of somebody I used to know. We start writing to each other, and wow, that message exchange picks up. We write long messages, we really get to know each other, we speak directly and honestly about all kinds of areas of life. He's intellectual and writes well. He has had bad luck with women and has low self confidence regarding sex. But he's trying to change his attitude and his life.

So, I decide to help him out, and suggest no-strings-attached sex, with the purpose of getting him over his sex-related hangups. He accepts the offer, knowing perfectly that it'll be charity sex. He says it's fine. We meet up. Yeah, he's really not my type, but whatever, just once, can't hurt... so on the second date, we have sex. I don't really enjoy it, I enjoy it less than I would've thought. He's putting in a lot of effort though, it's not bad sex or anything. He says "I know you're helping me out, so I wanted to make this about you, not about me". Sweet. But just... I don't find him attractive enough.

Then afterwards, we cuddle and he gives me the "I'm in love" look. Nope, nope, nope. I tell him we shouldn't meet again. He's mad at me, he says "you fuck like a guy" in a disgusted tone of voice. But then he gets his act together rather quickly. We part in friendly terms and never meet again.

After that, we've messaged once-twice a year or so. I ask him how he's doing, and hear that he found a fuckbuddy. Great! Next update, she's kinda his girlfriend. The next update, they're in a long-term relationship, and everything's going great! I'm happy for him and secretly think that some part of his success is because of me :)

Anyhow, moral of the story, I decide to never have sex with somebody who's not my type or who I'm not attracted to physically. It's just not fun and makes me feel bad. Attraction on a mental level doesn't seem to be enough.

If there's any part of my sexual history I could undo, this would be it. But, slightly contradictory to this, I think charity sex is a good thing in general, especially to help out a friend. Kudos to everybody who has done it.