Sex Lives: The Guy Who Cheated on His Girlfriend With Two Guys in a Bar Bathroom

Sex Lives chronicles the evolution of one person’s sexual history. This week: Jesse, 45, in Chicago, IL.

I’m somewhat embarrassed to say this: Do you remember the movie Clue? Yvette, the French maid. I know this makes me a man of refined taste, but I remember thinking: “Oh, I’m looking at her bouncing around everywhere, and that’s why I’m having this feeling. I grew up Catholic, and we didn’t really talk about sex; it just never came up. I knew I liked being aroused, but I didn’t have any language for it or anything. So I remember thinking, “Oh, when I’m looking at a woman, it feels good down there. That’s interesting.” I actually remember that connection.

Figuring out I was bisexual came later. I think the first time I thought: “Oh my gosh, I have a crush, I want to have sex with this man,” was— and I’m aging myself here—Kurt Cobain. I remember thinking, “Oh my god, he’s so beautiful.” Not only that, but I admire this musician more than anything—typical late Gen X. I had a poster of him over my bed. He definitely embraced queer culture; I don’t think we were calling it that, or at least I wasn’t in eighth grade. I don’t think I explored it very much until I was a little older. When I was in my early twenties, I had sex with men, but it wasn’t really until the last three or four years that I’ve been like: “Oh yeah, I am definitely, definitely bisexual. I have a lot of desire for men.”

Like most people, I lost my virginity in Delaware. I think that’s probably the virginity-losing capital of America. It was with my college girlfriend. We briefly started dating, then I studied abroad for a while, then I came home, and we slept together that summer. It was late; I think I was 20 at the time. We’d talked about it for a while and made out and done other stuff. I remember her asking, “Is there ever a time when you’re not hard?” I was anticipating it so much. And then we got started, and because I got so nervous, it went away. For the past 48 hours, I’d had a nonstop erection! It did work after a little bit. It was amazing for me; I doubt it was for her. It was exciting but also, like everything else you’ve built up, a little disappointing.

We had a really good sexual relationship, I think. We were together every day, and we talked all the time and explored different positions. She was more experienced than me, which made me insecure. I wanted to be like: “Oh, I’m gonna be the best, biggest, and most awesome.” And I’d get frustrated sometimes that she didn’t come—not quite connecting that maybe I might have had something to do with that.

We broke up after college ended, and I was serial dating, but often with overlap. Which I guess is a nice way to say “cheating.” I was with a bunch of different women. I had some relationships for some periods and some random hookups. Sometimes, I dated people for a few weeks and then went back to the last person and then to the other person. The numbers weren’t huge, but there was a lot of recursion and overlap. Some people knew about the overlap; some didn’t. Some also were dating other people; some thought it was exclusive. There are definitely some people who were very hurt by me. Well, people who I hurt. Let’s get rid of the passive construction.

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