u/kar_-_

I’m a 24F lesbian and I’m thinking about trying sex with my 24M best friend

Okay so for context, I’ve identified as a lesbian for most of my life. When I was around 13 I actually dated this same friend for a little while. We tried doing sexual stuff a few times back then but it was awkward and I just wasn’t really into it. I wasn’t attracted to him like that and not long after that I realized I was a lesbian

We broke up but we stayed close, he’s still one of my closest friends now.

After that I ended up in a relationship with a woman for a few years. Sex wasn’t really an issue there. I was attracted to her, I enjoyed being with her, everything felt way more natural. We broke up eventually for unrelated personal reasons and I’ve been single for about two years now.

My friend has had some random hookups and also a long term relationship that ended a couple months ago. Through all of this we’ve always been pretty open with each other about sex, relationships, what we like, our experiences, etc. He has also had feelings for me over the years, both romantic and sexual, but he’s always been really respectful about it. He never pushed anything because he knew I wasn’t attracted to him, or to men in general

The confusing part started after my breakup around two years ago. I randomly started having sexual fantasies about him. I kind of ignored it because I was in a weird place emotionally and eventually it stopped

But recently they came back.

Which is extra weird because until recently I was falling for a female friend of mine. We were flirting for a while but the whole situation got messy and it didn’t work out. Now that I’m starting to get over her, these fantasies about my male friend have randomly come back and my brain is basically doing backflips trying to understand what is happening.

The thing is, I don’t really know how to explain it. Some of the fantasies turn me on in theory, but I’m pretty sure they would turn me off in real life.

For example, I’ve always liked dirty talking someone and knowing I’m turning them on. I like the idea of someone being really affected by me sexually. If I see a woman touching herself because of me, that would have me doing actual backflips. But with a man it’s different. The idea can turn me on, but actually seeing it happen turns me off instantly

That has happened before. It happened when we tried stuff years ago, and it happened again more recently when we were sexting. In my head the fantasy worked, but in reality seeing a man touching himself like that just threw me off completely.

I think a lot of these fantasies are like that. Things that sound hot in theory but might feel completely different in person.

But then there are other things I’m less sure about. For example, I’ve always liked penetration with toys, strap, etc.

So part of me wonders if I might enjoy penetrative sex with him because physically maybe it wouldn’t be that different. But at the same time, part of what I liked with women was watching my partner enjoy touching me, even if she couldn’t physically feel it herself. So I don’t know if I would enjoy it with him, even though I know he wants to do it and would probably enjoy it

We’ve talked about all of this pretty openly and we decided we might try having sex once to see how I feel about it. If it goes well maybe it could become a casual occasional thing. If it doesn’t then at least I’ll know

Honestly I don’t know what to expect. We’ve been talking and sexting and that part has been fun. I know I’m not physically attracted to him, but somehow the idea of having sex with him still turns me on a little, but the more I think about it the more that is throwing me off

I guess I’m writing this because I needed to get it out somewhere. I’ve talked to one friend about it but I don’t think she fully understands the weird mental loophole I’ve gotten myself into.

Has anyone experienced something similar?