Sex Lives chronicles the evolution of one person's sexual history. This week: Theo, 31, in Providence, RI.
I remember going to summer camp after sixth grade, and a kid who was older kept talking about jacking off. I just played it cool because I had no idea what he was talking about. I also remember—I’m sure this is a very familiar experience for a lot of people—stumbling on HBO's not-quite porn. The first few times, no come really came out, but I knew it was supposed to. And then, the first time I really tried to orgasm, I was watching something OnDemand, and I tried to stick my penis in a Gatorade bottle. It didn’t do that much for me, but I’m shocked at how instinctive doing that was—like, some come came out, and I was like, “Okay, I’m on the right track here.” I was home alone, and there were boobs on the screen, and it was like my body just knew to put my penis in something.
I thought I was the only person who knew how to Google Image Search in my family. I’m a school teacher by day, so I’m qualified to say that young people are dumb. I think I looked up the word “boobs” or something, and then someone—I think my mom—was like, “Hey, by the way, don’t do that.” When I watch porn [even now], I don’t usually watch people having sex; I watch girls alone—in part because guys are always saying stupid things. I don’t like watching blow job videos, either. I remember early on, my mom called me out for watching porn. She wanted to know what I was watching because there was so much damning stuff out there. She was like: “What are you searching? Blow jobs?!” And I remember being really embarrassed by that, even though I wasn’t. I wonder if that’s the reason I still don’t like watching blow jobs in porn.
In middle school, I was making out and doing second-base stuff, and then I got a hand job in eighth grade, and I remember being like, “Well, only like three people are on the record as having gotten hand jobs in eighth grade.” I was off to the races from there—being horny is a big part of my life.
There was a girl that I would sext with a lot, and I’d take pictures on a digital camera and upload them and email them to her because that’s how you did it back in the day. Having sex was very much this thing we wanted to try. We weren’t dating, though. It was just like two horny people coming together to try it. I don’t remember it being much of anything; she didn’t bleed much. I think she was surprised that that wasn’t even a thing. I’m sure I finished quickly, but later in high school, I was having more consistent sex. As a high school teacher, I shudder to think about my students getting up to no good, but I guess that’s what you do at that age.
I had a lot of sex during my senior year of high school with miscellaneous people. I had a car and had a lot of sex in the backseat of that car. But college… this is less about sex and more about my personality. I was good at being a big fish in a small pond. I understood the social levers in high school well. So I was like a cool, charismatic person. Then college was big, and there were completely different rules of engagement, so I had less sex in college, I think. I didn’t know how to meet strangers at parties or things.
Quite frankly, by using dating apps after I graduated, I started to have a lot more casual sex because it was easier for me to engage with people on their own terms. Then I moved to Australia for a bit, and that was a lot of casual sex because of the dynamic of being an object of interest. I also got hotter in my mid-twenties, and I think better at sex (or at least more chill about it). When you’re a teenager or a college kid, even if you’re able to have consistent sex, it’s still the biggest thing in the world. I feel like I just hit a good stride, I suppose.
I dated someone on and off for three years after that—off mostly—and that was monogamous. I’ve had a few monogamous relationships, and I’ve been in a relationship for a while now. I’ve explored buying people's nudes a lot, which is permissible in my relationship. That’s been an interesting shade of gray. We’re monogamous, but she knows I’m on Onlyfans as a buyer, not a seller. I really like sex, but the validation of nudes gets me off. Like, I don’t need sexting for my soul or anything, but it’s hotter than masturbating alone. The act of having one partner, I feel like there’s an occasional itch I’m not scratching, but I understand that there are other things that are as important or more important than getting off to my heart's content. So, it wouldn't be a deal breaker if a partner asked me to stop buying nudes.
There are some flashbulb sex memories that stick out; I don’t know if they’re for any particular reason, but it’s like if you start masturbating to something, it becomes canon. Like, I have a memory of a girl I dated in my twenties; I got such a great look at her asshole while we had sex. That’s just like a good memory in my mind. It wasn’t the first time I’d seen an asshole or anything; it’s just part of the library. It seems to me like there are two types of squirting. Like one where there’s just so much pressure they just pee on you. And then there’s others where there’s like a reflex, like you hit the right button. This one woman, just like every 30 seconds, if I flexed my finger or my hips the right way, she would squirt everywhere. It was so surprising and fun and different.
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Something that I’ve recently toyed with is piss play, but I don’t think I like it. I think I want to like it more than I do. Pee is really hot—like temperature-wise—in a way that’s hard to ignore. I have brought it up a few times, and every person I’ve been with has been like, “Sure, we can try that, I guess.” And it’s a little shy and a little funny. And then it's really hot temperature-wise, and now we have to clean up pee. I keep coming back to it when I’m sexting with someone or in porn, but in real life, it’s not as exhilarating. I don’t really want to pee on anyone. One time a girl wanted to hold my penis while I peed, and she thought that was really hot, but it’s not as much of a two-way street for me.
The only time I had a threesome, I was super stoned, so it wasn’t that fun; that’s a craw in my side. There was a girl I hooked up with a few times and a girl I had sexted with a bunch, and I forgot how it came up, but everyone was in. They came to my apartment, and the girl I’d sexted with was like, “Oh, we should smoke a joint!” I feel like when I was a teenager, I could smoke pounds of weed and be fun, but now I look at a joint and get nonverbal. So we smoked a joint and watched The Office, and like we did it, but it became clear that we were too stoned. It didn’t seem like anyone had chemistry, even though we all had chemistry individually.
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