Sex Lives: A Former Football Player Who Likes Wearing Women’s Underwear

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 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.

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