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



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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?” 

Sex Lives: A Guy Who Decided to Stop Having Sex With His Wife on OnlyFans When She Got Pregnant 

A 34-year-old straight man in London breaks down his entire sexual history. 

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