Sex Lives: A 28-Year Old Guy Who Went Through a Phase With Older Men

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For Sex Lives, GQ speaks with someone about their entire sex life up to this point and how their sexuality has evolved. This week: Dylan, 28, Chicago, gay. 

I discovered [gay] porn on spring break in sixth grade. I remember I got grounded and I have no idea how I found porn—I don’t think I even really knew what being gay was at the time. I lived in a very sheltered Catholic household. My mom is very Catholic and my father is 18 years older than her and introverted. So sex wasn’t really something we talked about. We didn’t really know anyone who was gay, so I have no idea how I found this porn, but I was just like, “Oh, okay.” And because I was grounded at home alone for a week, I just threw myself into it. And from then on it was a lot of yearning and confusion, because in my household it was like, being gay is really bad.

I had come out to a couple people in high school and they pointed me to this older guy—he was the token out person who was older at our school. He helped guide me to come out to my parents. Basically, I was very afraid that my mother would kick me out because again, she was very Catholic. We went to mass every single Sunday until I left for college. And she’s very strict; I’d get grounded for a month, I’d lose my phone for a month. So she’s punitive and the church is very clear that this is wrong. So I made a plan with a couple people about where I can stay if my mom kicks me out of the house. I did it on the Monday of a three day weekend so that I had time for the buildup, I guess.

My mom actually took it really well—she said she had known since I was five. She told me during that conversation that she had actually tried to hint at it to my dad. After I told her, my mom suggested that I wait on telling my dad and said that she’d talk to him, and I was like, “Okay, fine. If you want to do it, by all means.” I told my sisters on Tuesday or Wednesday that week and she told my dad Thursday night. He stopped speaking to me for a month. He actually has a daughter from a previous marriage who is lesbian; she’s married, she has a partner. So my siblings and I talked about it and I thin the reason he took it so poorly is that there’s a way to rationalize the first queer child in a family. The second queer child from a different marriage? “It’s you.” So he kind of shut down about it, and he was in denial. That continued on for a year and then even when I would date people until fairly recently, he would still refer to them as my “buddy.” But now he loves my partner.

I lost my virginity between high school and college. I farted during it, so that was really just one of those really embarrassing moments, like “Please light me on fire. I would like to die right now.” He was my first boyfriend. According to him, I was somewhere around their 300th partner. I go back and forth on whether he was telling the truth or not. We dated for a few more months into college and then I was looking at his Twitter and I realized that he was tweeting out how to break up with me.

I then went through an eighteen-month dry spell. One of my friends was like, “if your dry spell were a child it would be talking by now.” Then I started dating older men. It’s a psychologist's wet dream: “Your father is in his 80s now and you’re into older men?” I went to a school in rural Missouri so it was very slim pickings, but when I came back home to St. Louis, I met up with a guy from Grindr. He was 28 and I was 20, so we were just in different parts of our lives. He wasn’t manipulative or anything, he was a very good person. He also had, I’m not kidding you, the world’s biggest dick. There are just some things you cannot do after an eighteen month dry spell. The first time we were making out, I thought it was his leg; I’m not joking. Between that and the different stages of life, it didn’t work out. Then I went into a real slut stage.

When I was 20, I had sex with someone who was 55. I wanted to have sex on his motorcycle because that checked a lot of boxes. But then his motorcycle was being repaired; it wasn’t available for use. Probably the best sex I had was with a firefighter. He could pick me up! We did multiple positions, multiple places in his room. Then a few years later I saw him at Pride and he turned out to be racist. So that ruined that.

My boyfriend and I, I wouldn’t describe us as open, but we’ve both made out with other people at bars and it’s not the biggest deal. A few months ago he made out with someone at a bar and we were with all his friends. One of his friends was like, “Isn’t that your man? Aren’t you upset?” and I was like, “Who is he going home with tonight? It isn’t this fucker, it’s me.” Recently, we were very drunk at some random bar and I was making out with a guy who’s a little younger than us, and my boyfriend found us and was upset that he wasn't the one making out with the guy. And then we brought this guy with us to another bar and at this point it was like 4 a.m. so everyone starts to go home and he says he’s going to get the L home, which is a 40 minute ride. So I offered to let him come back with us in our Uber and sleep it off at our place, like “we won’t do anything.” We all got home and passed out; the next morning I woke up and I found out that the guy on the couch was 18. He was like a child! I would never make out with him sober! I’m 10 years older than him! 

I’ve been in a few threesomes. One of them was in rural Missouri, don’t do that, avoid that. The other was with my current partner. That was better, but then afterwards the guy got progressively less hot. Be careful who you pick, sometimes you look back and you’re like..."what?" We’re both into it, it will probably happen again. We were about to have a threesome one time in another city, but I was being a bit drunk and jealous and the other guy was like, “I don’t know about this.” That was a good call on his part. 

I was with a guy who was into tying me up, but he wasn’t very good at knots. So I’d try that again with someone else. I was also blindfolded and it was my first time trying poppers. That was kind of fun. Drunk Me is a big fan of going to the nearest sex toy shop and buying six bottles of poppers. And then sober me is like, “Why do we have six bottles of poppers?” 

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