UrbanUpdate

Sex Lives chronicles the evolution of one person's sex life. This week: Tyler, 32, Kansas City

In my case, there's two virginity losses. I went to a very conservative Christian high school and middle school. I grew up in San Antonio—where I grew up you could murder somebody and as long as you weren’t gay you weren’t as bad as the homosexuals. But I knew I was totally into guys. I was a super-athlete and on all the sports teams; I played varsity football and baseball and basketball. I was a guy's guy. I knew how to do that. My very best friend knew [I was into men], but no one else did. 

There was this website—I don’t even know if it exists anymore—called XY.com. You can maybe surmise XY was a gay/bisexual teenage website, they probably attracted all sorts of older pervy dudes, but they had a chat feature and you could sort by location. I started talking to a guy who went to a private Christian school and it turned out to be my high school. After three weeks of trying to get the other person to announce who they were, he finally took the lead and told me his name. 

We both were incredibly sexually frustrated, horny-ass virgins, who didn't know anything. I was 15 and he was 14, so neither of us had a car. And we were like, “we should find out if we are actually gay.” So we went to this abandoned portable bathroom near the journalism building. So my first sexual experience was at lunch one day. We went out there and met up and just jacked off and made out a little bit and tried to feel our way through it. And that continued the rest of high school. I found out very quickly that I am totally a bottom. 

 It was never romantic, though. It never occurred to me that I could date a guy, right? I was thinking, “Oh this is fine, but of course—of course—I’m going to end up marrying a woman. This is just a phase.” That continued through high school and into college, we hooked up a couple times in college. He’s married now to a very nice woman and she’s fully aware [he is also into men]—it’s not a secret to her, which is good.

In college I dated a woman who I ended up getting engaged to. She was very prim and proper—like if you were to draw up a Christian girl stereotype. My family called her Barbara Bush because she wore pearls all the time. She didn’t know I was into men; her family hated me for a multitude of reasons. God knows what they would think about the gay thing; they hated me because I was a Methodist. 

I’m not proud of the fact that I definitely cheated once, and I nearly got caught. Someone sent me a dick pic and she found it and I lied about it. She may have suspected at the very end, but we broke up and it had nothing to do with that and everything to do with just not having compatible personalities.

I’d been dating her for a year and we hadn’t had sex yet. She wasn’t ready both for religious reasons and because she had a bad experience with a family member when she was younger. She was waiting because of that, and I was waiting because I didn’t really want to have sex. But we were out of town together doing an internship in the same city one summer and we decided to have sex. I went and bought lube and condoms at CVS and I swear to God we carried them home like they were nuclear bombs. 

For extra protection, we got condoms with spermicidal lubricant on them. We had no idea what we were doing, there was no foreplay; she was tense, she was tight. It was never going to work right. So I was like, I’ve watched porn, I’ll go down on her and maybe that will help her loosen up. The spermicidal lubricant turned my entire tongue and mouth and lips numb. My lips swelled up to about the size of a clementine, you know those little oranges. It turns out I’m horrendously allergic to that, and she was also allergic to it. Her vagina swelled up, it started like turning inside out. We were both googling and we each took like six Benadryl trying to get it to go down and we ended up going to urgent care. They gave her an actual shot in her lady bits to help bring it back to normal and they told me to just wait it out. So that was probably the worst sex I ever had.

The best sex I ever had was in Lyon, France. I was there during grad school and I went out with a friend of mine and I hit it off with this 50 year old guy—like, the most beautiful older Frenchman. I'm super into older dudes. I don't know why—I have a great relationship with my dad, everything's normal. Nothing bad there. I guess because they know what they're doing? I don't know! Anyway, he had this boat, and there was a canal system like in Amsterdam and he took me back to his boat and we sailed through the canals. We went on a few dates and then we went back to his boat one night after dinner and the canal was beautiful and we had wine on the deck and it was totally deserted so we ended up having sex on top of the boat under stars in southern France. And it was the pretty much the hottest experience of my life— the most romantic sex of my life. It was also really good sex!

I have always hated guys' underwear; it’s always black or gray and boring and terrible. I’ve always liked prettier, more feminine things. Softer things. So when I was fourteen, I was at the mall with friends and we were done shopping and I ran back in to go to the restroom and I ran through a Macy’s and they had this table of panties out for display and they were the prettiest things I’d ever seen in my fourteen year old brain. I don’t condone this, but for some reason I grabbed like three pair and put them in my pockets and walked out with them. When I put them on I was like, “Holy shit. This feels so right.” I can still see them in my head. They were white with little green and red hearts. And they were so cute. And I was like, “I'm in heaven.” I know that sounds stupid but, I can still remember that feeling. 

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I kept them a secret for a long time. Once I started driving and could pay for them and self-checkout and Amazon became a thing? Boom. The money I earned working at University Methodist Church over the summer months bought so much girl underwear my freshman year of college. I've always been attracted to more masculine guys and also older guys, and let me tell you, they love the whole panty thing as a rule. Unless I need to go to a doctor’s appointment or something I wear panties; I haven’t worn anything but in forever.

COVID has impacted dating a lot; there have been a lot of one-off dates. I tried dating women a little bit again, but it doesn’t… I dated this girl who was amazing, so sweet and I told her everything upfront. And she was like, “Yeah, I can roll with this” and holy shit the emotional bond we had was incredible. We had the best time, the best conversations and the cuddling was amazing, but the sex was terrible. I just couldn’t make it work. I tried every potion and tincture and pill I could find that would make me get it up and I just couldn’t have P in V sex. I kept waiting for her to stick it in. I feel like with women they often want me to take on this manly role and I have two dresser drawers full of the frilliest most feminine underwear you can find; I have more makeup than most people. I think we were just both waiting for the other person to “be the man” for lack of a better phrase. 

Oral sex? Great, that’s easy! Pleasuring each other? That’s fine, we were both good at that. But when it came time for P in V sex, I just didn’t want to take on a dominant role. I’m going to end up with a man if I end up with somebody, you know? That’s kind of where I’m settling. I’m still so emotionally attracted to women; men emotionally are just boring as fuck most of the time. I grieve the fact that I won’t get that with a woman because I would love it. I tried a dominatrix. I tried being pegged, but a rubber dick just isn’t as good. I mean: It can’t come! Like God help me, that’s one of my favorite parts of sex—when he comes, you know?

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