Sex Lives: A Guy Who Was a Late Bloomer and Is Now Dating Divorcées

Michael Houtz

Sex Lives chronicles the evolution of one person's sexual history. This week: Joel, 37, in San Antonio, TX.

There was a bit of a sketchy group my older brother would hang out with. One guy was like, "Hey dude, I got something for you," and then gave him a porno video—which sounds so dated—but my brother and I watched it, and I got very aroused. Later that day, I went to the restroom, and it was my first time jerking off. I think he just thought it was funny. Like he and his friends showing me a porno video and being like, "Look at this, dude. I bet you've never seen a pair of tits before, and now you're going to watch a porno of some girl getting fucked." It didn't feel in any way shocking. It was just like, "Oh, this is awesome." I didn't feel dirty or freaked out, like, "Oh my God, this is so cool."

I was very much a late bloomer when it came to sex and dating. I don't know if I was just shy or what. My parents sent us to an all-boys private school, and I had no desire to try anything that way. So it wasn't like I had a ton of exposure to girls, even though we had school dances and stuff like that. Then, I went to a university, where I was the poorest kid. I'm sure it was more in my head than anything, but when you go to a really rich school and you're the poorest kid in your class, there's intimidation in talking to girls. So even sometimes, when I would get a date or two, it wouldn't go beyond that. I didn't have my first actual sexual experience until I was 24.

My good high school friend said, "Hey, I'm going to score tonight with this girl. She's bringing her friend along. Would you like to be my wingman?" And I was like, "Sure." The friend was flirty with me and took me back to her place; I was so nervous. I don't remember too much of it, honestly. I remember she seemed very nice about everything. She gave me head for a bit and put on a condom. I don't remember how long it took me to finish or anything. And then I just had a mini freakout and was like, "Okay, I think I'm going to go home." She was like, "You can spend the night and stay." And I was like, "Nah, I should probably go." I remember calling my best friend, and I told him, "Dude, I feel kind of freaked out." He was like, "I think I felt freaked out the first time, too." But I never talked to her again; she didn't seem to care. She didn't know [I was a virgin]; I would have been terrified to say that. I mean, I was 24, so I think she just thought I was a weird guy.

I've thought about this before, and it didn't feel like insecurity or pressure to lose my virginity. But it does feel like—and this is gonna sound weird—but it really feels like it doesn't matter how many girls I sleep with, I'll always feel a little bit like I'm a prude because of how late I lost my virginity. I know that makes no sense, but I will never feel like I am a guy who gets laid easily, even though now I have way more success in the dating world than a lot of my friends who are still single or like the average guy. It just never feels that way. It never feels like, "Oh, it's so easy for me."

I got on Tinder when it was early on, near when it first came out, like 2012 or so. A lot of it is that I've had to grow out of being an introvert and being shy. I've had a lot of things not romantically related that forced me to do that, like my job. Also, my height—it's more of a thing when you're younger; now I forget sometimes that I'm a shorter guy, and when you're older, it's like, "Who gives a shit?" But I've always had a thing of, like, I think that girl's cute; there's no way she'll be into me. Once I got on Tinder, all of a sudden, I started getting matches, and I was like, Oh, these are girls who think I'm attractive. These are girls who think I'm cute. So, that was how I started feeling more confident.

I only went out with a couple of girls before I was about 27, and I had my first girlfriend. We weren't together long. She was very Type A, and in the bedroom, she had no problem being like, "I want you to do this and this and this." She even asked me the first time we hooked up: "Have you been with girls?" And I was like, "I have!" But she wasn't mean or anything. She was mean in other ways. But she said, "This is how I like to get eaten out. This is my favorite position. This is the way I like you to be more rough." There was a lot I learned from her.

Shortly after we broke up, I moved to Minneapolis for a while. I'm Hispanic, somewhat light-complected—but I don't look British, you know?—and have thicker hair. I bring that up because when you get somewhere like Minneapolis, and you look a little bit different—not a ton different, but a little different—well, I did a lot better when it came to dating. Girls wanted to go out with me, and honestly, it felt like a significant change happened for me.

I met a really pretty woman up there and we were sleeping together on our third date—you know, pretty typical. I always worried, like, "Do I finish kind of quick?". I would always go into having sex a little nervous, you know? As we were having sex for the first time, I looked up at her, and I was like, "I think I'm going to come," and I expected her to be like, "Ugh, already?" or something like that. And she just said, "Isn't that the point of having sex?" It was just such a cool answer. I think that was the next level for me in having sex, where I started feeling more at ease, and the sex got so much better with her than it had been with previous girls. It was also really my first introduction to how much chemistry matters and how much liking the person matters. We were together for a few months until I had to move back to San Antonio for family reasons.

When I moved back home, I met someone through online dating, which turned into a two-year relationship. The sex was great with her. She was the type of woman where the way she touched me and grabbed me was very much a turn-on. Like she was physically signaling to me how much she liked me. I have this memory of it. It felt like every time we would have sex, she would almost dance into the bedroom, just like excited for it. She's probably the closest bond I've had with someone I've been with, so sex would last longer. We were pretty open about how we talked about sex, so we learned each other's bodies a lot more. She wasn't someone where coming would happen fast or easily, so we'd take a lot of time. It was really good. Obviously, it wasn't a perfect relationship; it ended.

She was probably the best sex I ever had. It wasn't that there was one time; I think it always felt great because of how close I felt to her. Like, we talked about getting married, and that fell through, but there was a strong emotional bond. It always felt different being that close to somebody. I know it sounds weird, but all of our sex almost blends together. It just always felt great.

I'm very light on my kinky side. I've got a list of stuff I've done with a few women, but it just boils down to do they like it—toys, bondage, anal. But it's only if she's like, "This is what I want." I've never been like, "Oh, trust me, you'll like it," or "Let's try it and see how it goes." I don't know if it's the women I end up attracting, but it feels like every woman I've been with has been much more on the submissive side. Generally, I'm a very chill, go-with-the-flow guy. I can't imagine myself with a woman in the bedroom who is like, "Do this right now!"

I think with my ex, the only regret I have is that we had talked about getting more kinky. For a good bit of our relationship, I wasn't in the most mentally healthy place. I was dealing with family loss, and work was stressful, and then COVID started. Looking back, I think she signaled that she wanted to try more stuff, which I've probably done with other girls. I don't know why I didn't jump more at it at the time. When I look back at it, I feel like I was probably too depressed, which is part of the story of why we're not together anymore. We were still having sex; it just felt different. I wasn't taking care of myself the way I should have. And with COVID, we went a couple of months without seeing each other because we weren't living together; she was locked up in her apartment. I would say that weighed heavily on it.

After that, when I started dating again post-vaccine, I met a lot of women who didn't want a relationship. They were like, "I want you to take me on nice dates, treat me well, and have sex." One of the women I met—it is silly that this should play a part in it, but—she was Swedish and had this very attractive accent. She also had a body type that I'm very attracted to. It was probably the fastest I've just hooked up with someone. We met for coffee, and I needed to go back to my apartment to drop something off, and she came with him, and so, like, two hours after meeting each other, we were already having sex. It felt like we were supposed to if that makes sense. It was just insane chemistry. She had an amazing ass, and after a couple of times of having sex, she was like, "Oh, by the way, I really like anal." And I mean, I wasn't gonna say no. Later that day or the next time we hooked up, we did it, and she orgasmed from anal. It was very hot. I think we just had a lot of chemistry.

In some ways, it's beautiful, and in some ways, it's frustrating because it's like, "Oh man, I have this with someone I'm not gonna be with." We had this almost movie-esque last night together. I took her to this Airbnb. She'd been through a ton of bad relationships, and she had this moment that night where she was upset that we couldn't be together. It came from the fact that she was finalizing her divorce. She didn't want any more kids; I still hope to have kids. You know, things like that. She'd already been twice divorced, so she didn't know if she wanted to be serious with someone again. She was going through a lot; she ended up getting back together with her husband for like the fourth time. Of course, that didn't work out.

I've been with several single moms and divorcees, and that doesn't bother me, but the scheduling becomes part of it. Also, you gotta know that the single mom needs to vent about their ex being the worst person ever. But yeah, scheduling is the hardest part of it. It becomes interesting if you're one of the first new people they've been with. I was with one woman who was 33, and she was like, "You're the only person I've ever been with other than my husband." It's not different to me, but it just highlights how important it is to create a space where the other person feels comfortable.

As I've gotten older, I've realized that most people come with hang-ups about their body and their past and how that compares to others. Good, healthy sex requires you to just be so grateful that they're sharing it with you in this moment. It's the best thing ever. Maybe this is another late-bloomer thing, but when a woman is down to have sex, I still get excited about it. 20-year-old me would never believe this was happening.

Originally Appeared on GQ