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.
I think at the time, I would have said I was just in love with everyone and liked having sex, but now that I'm older, I think it was the validation of someone wanting to have sex with me. I don't know if it was a product of being late in losing my virginity or just basic insecurity or what. I think the validation of someone wanting to fuck me has been—for most of my life—more important than the fucking itself. That second where you realize, "Oh, we're gonna fuck," is often way more exciting than the actual sex. I mean, I love sex; it's incredible. Don't get me wrong.
In my early twenties, I remember talking to a friend, and they were like, "Jesus, you have more sex than the rest of my friends combined." I realized I liked men; I realized I enjoyed talking about it. But I think I liked the idea of it more than I was interested in actually having sex with a guy. Possibly, that's because of a lack of knowledge about the particulars of doing it. I was pretty good at having sex with women. Or at least I was good at being able to have sex with women. And I could be like, "That guy's super hot," or "Look at that dude." But it wasn't until recently that I would jerk off thinking about men or anything like that.
I was in a gay bar in Chicago; I'd gone to some before to see what it was like, and I was talking to two guys, and they invited me to the back room. I was pretty drunk, and I was like, "Yeah, let's do that." One of them fucked me while the other one sucked my dick, which was very exciting. It is weird, though, because it's very blurry. I was very drunk. I didn't think about it too much afterward. It was like—well, that happened, or I'm 99% sure that happened. I wasn't embarrassed, but I was dating someone who expected me to be monogamous. I got tested afterward and everything, but my girlfriend and I weren't having much sex, so it didn't come up.
I was in a long-term relationship with her for a few years, in which, to be honest, I cheated relentlessly. We just stopped having sex. I was traveling a lot for work, which was an exciting time. I also had an ex-girlfriend who would go through phases of threatening to kill herself if I didn't come over and fuck her and then threatening to tell my girlfriend that we'd have sex if I didn't come over to fuck her again. It was pretty awful. But the woman I was in a long-term relationship with and I broke up. I essentially forgot how to have good sex with her. Then, there was a cycle where she wasn't getting anything out of it, and so she kept getting further and further away, and then we had less sex. I started dating someone else and was married to her until last year.
We worked together and then started dating, and until recently, it was the best sex I've ever had. It was really good; she was adventurous, we had a really good connection, and her body felt amazing. She was much more sexually knowledgeable than other people I'd been with about her own body. Even when things were bad, we had a really good sexual connection.
Things were getting bad, and I was getting bored, I think—that's more psychology than sex, though. I spent a lot of time trying to be like: "Alright, I'm moving into the phase where I'm going to be a good husband." Not in terms of sex or monogamy but more in terms of being responsible and doing things right. Then, sex just started to diminish based somewhat on a medication she started taking, and I was stressed with work, and she was going back to school, and we didn't have any time for each other. And once the sex crumbled, sort of everything else did, too.
We didn't ever hook up after we separated. We talked about it. She was like, "Here's what we could do." But she was also exploring her own sexuality; she's currently in a throuple. I started seeing someone shortly after we separated, and I still am. So, we did not hook up anymore. It was rough for a bit, but we're finally friends again, which is good. Last Saturday, we hung out for the first time and actually had a nice time, which was great. But there's no attraction or sexual connection—just a reminder that I still like this person.
I started seeing someone with whom I've been friends for years. She was the only person I was ever really honest with because she lived far away. We would write long emails to each other, so we knew almost everything about each other because we figured we'd never meet. She separated from her husband last year, and when my wife and I started to separate, we were just like, well, let's give it a whirl. She moved here for a bit, then moved back to sell her house, and is now moving to California. I might move there. I'm a Midwestern guy, but there's no reason I have to be.
I'd jerked off to her like a billion times. She's just a beautiful woman—really incredible. And then we connected after we'd separated, and I felt like I'd never had sex before. Our sex is exactly what I hoped it would always be like—actually, even more than that. She was driving across the country, and I met up with her in the most romantic city in America, Toledo. It was just where our paths intersected.
We'd fucked a few times before then, and then we had a month or two where we didn't see each other, and we poured out every fantasy that either of us had ever had. The second we started fucking… it was perfect. It was intense and rough. She was slapping me, and I was holding her down, and we were just being violent and intimate. We were on the bed. Against the wall. At one point, there was a full-length mirror, and I was fucking her from behind and holding her up by her tits, and she was the most beautiful fucking thing I've ever seen in my entire life. I've thought about that a billion times. Just the way she looked and the passion and intensity on her face. I've never felt anything like our sex or her.
We're long-distance, so we send each other pictures a lot, and we tell stories to each other, fantasies, and things we want. Sometimes, it's pretty tame, like "You come into the room, and I come in…blah blah blah." She's really into jealousy, so she enjoys me watching porn and jerking off or fantasizing about me fucking someone else. Although not in real life.
She likes stories, especially ones where I'm a much older man, and she's younger. I want to watch her suck someone off. She's back and forth on the idea. She's very into it in stories and was into it a lot when we first got together, but now, not so much. It's not like it doesn't turn her on— it turns her on a lot to think about, but she's also very mindful of the dynamic. Like, this could fuck us up.
I'm very into ballbusting, so I would like to see her do that to someone else. I think that'd be really hot. I never wanted it before. I never wanted to watch my partner do something to someone else before. I think it's just that her beautiful fucking body and face and the way she thinks about sex. I'd love to have her do things to someone else so they could be like, "Holy fuck, this is the best thing I've ever seen in my life."
Originally Appeared on GQ