Sex Lives: A Guy Who Started a Complicated Roommate Situation


Sex Lives chronicles the evolution of one person’s sex life. This week: Omar, a 30-year-old trans guy from Chicago. 

I had a boyfriend when I was 16 [before transitioning]. We were going to go to the movies, but the movie we wanted to see was sold out. So we went back to our car in the parking garage to hook up and he was like, “I have condoms, do you want to have sex?” and I was like, “Okay.” So I had sex for the first time in the back of his mom’s car, in the movie theater parking garage. I think we had sex maybe two more times. That was it before we broke up because he was having feelings for his best friend, who was a guy. Now he and the best friend are both out. 

I was hyper-sexual as a teenager. I had lots of boyfriends and hooked up with lots of guys in high school. Only for the thrill of it! I wasn’t having good sex as a 17 year old with 17 year old boys. It was just more like a “hahah I blew him” situation. In high school I fucked some twins. Not together! I hooked up with one twin and then later I hooked up with the other.

I went away to college and I fell in love with my roommate. We started hooking up when we were drunk and then we would hook up when we were sober and then we spent a whole summer apart without talking about it, but we’d already signed a lease to live together the next year. And then we got back sophomore year and immediately started hooking up again like… “I guess we’re girlfriends.” So I ended up dating my freshman roommate all through college. She and I are still friends! 

It got to a point where my girlfriend and I couldn’t lie to our families anymore about being just friends. So we went home for spring break and we each separately came out to our families and told them we were dating and had signed another lease together for an apartment, with a couple other people. But still, it was a whole fucking thing. Our dads both took it very well. Our moms did…not. My mom immediately left the room and threw up, which was really fucked up for someone who was always like, “I love gay people, we should all be accepting!” My mom was very, very uncomfortable with my sexuality and that kind of ruined the relationship that we had had up to that point, because we were really close. She made it clear to me that she was not comfortable with lesbians, she seemed grossed out by it. At one point she was like, “This would be easier if you were a guy,” and I guess I latched onto that.

I started experimenting with gender presentation when I studied abroad in Barcelona. My girlfriend and I were open and I started hooking up with other girls and dressing more butch. There were a lot of hot butches in Europe. I’d always been uncomfortable in dresses and skirts, so that wasn’t a huge surprise. That was the era of like, dapper butches. It was like, bowties, which is so embarrassing. That’s not who I am now, but that was me trying on a type of masculinity I could access easily. I bought a binder on Amazon from one of those companies that advertises as like “tomboy lesbian cosplay tank top.” They were so shitty and they had like clasps. But I still was like, “Oh I’m a girl, it’s cool, it’s fine!” 



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