Sex Lives chronicles the evolution of one person's sexual history. This week: Jackson, 30, from Chicago.
The first time I jerked off, I think I was in fourth grade. My friends had bought some Girls Gone Wild tapes—had to steal money to get it—and I went home and I masturbated in the shower. I remember it vividly because there was blood in my semen when I came, and that freaked me out! I didn’t do it again for like a year.
Also, I went to Sunday school that weekend after masturbating and the sermon the teacher was giving was about masturbation and I was pretty sure I was damned to go to hell.
I realized I was queer in around sixth grade because girls would ask me out to dances and I just wouldn't have any interest. It actually made me angry or nervous when they’d ask me to dances in public. I remember talking to my reading teacher and asking her, “Why do I feel nervous about this?” and she was like, “Maybe you don’t like girls.” And when she said that, I did think back to the Marilyn Mason videos of him having fake breast implants and how I felt [turned on]. And that was one of the first times I realized that I wasn’t attracted to only women.
I lost my virginity when I was a freshman in college and my girlfriend at the time—she’d been my homecoming and prom date from high school— came to my dorm room and my roommate was in the room. It was a very small dorm, so we were like eight feet away from each other, and it was late at night. She was like, “I want to have sex right now.” I didn’t because my roommate was in the room. Also, my roommate was kind of weird. Looking back, he was kind of incel-y. He also never talked to anyone and just watched Adult Swim 24/7. I remember my girlfriend started putting her hands on me and we started to have sex and I turned my head and I just saw my roommate watching us. It was so awkward and extremely off-putting for me. I pulled out and I was like I have to stop, I cannot do this. She took that as “I don’t want to do this with you.” And so then she and I didn’t talk for a while—That was the end of things.
In college I would hook up with guys I’d meet on OKCupid or Tinder. Tinder came out my junior year of college. So I had random hookups with people. I joined FetLife around that time and I’d meet people that way. When I was in college most of the women I’d see were very bottom-y and never wanted to reverse the roles in any way, shape or form. I did see someone who was 37—16 years older than I was. We met off OKCupid, and they were very comfortable being dommy. I also had sex with a trans woman who was in the English department and we had a couple classes together. They asked me and I said yes and we hooked up in our school’s student center, right across from the financial aid office. And then we moved to the top of the university’s parking lot.
I’m single now; I actually just dumped someone last week. So I’m back on the apps now. It was a three-month-long relationship. I was in Berlin for a while and there’s the whole Berlin thing with all the techno clubs, and S&M clubs, and dark rooms.
Then I went to Paris, and I met someone off of Hinge and I thought it would be just a hookup. But we spent every passing moment together. Every day. I actually pushed my trip back a few days to spend more time with them. I actually ditched my friends I was there with. The person I was seeing back here in Chicago—the three month relationship—was very boring and they wanted a more domesticated life. Picket fence, stuff like that. I’m not that type of person; I’m a Sagittarius, I have a Scorpio moon. That stuff freaks me out. So boring. I was like, I do not want to be in a relationship with this person when I go back. I finally had this relationship model of what I actually want with someone in Paris. I came back to Chicago, tried to make it work with this person, and I was like, no, I’m bored out of my mind. So I stopped seeing them. I still talk to the person in Paris every day. We’re sexting. I’m going to fly them out here next month.
I’m not out in my professional life. I work with people who are out, but my field is very, very white, and I feel as a Black man, that if I were to tell someone who worked with me about my sexuality, it would almost betray their image of me. Or they would hold it against me in some way. Or, some people I work with get paraded around [because of their identity] and that is not something I’m comfortable with at all. They’ve done that with the job I’m on and I don’t want any part of that. There are times when I’ve gone out with people from work who are gay or queer or trans and I would like to pursue something, but I’m just not comfortable enough to be out. I feel like I’d like to be more established.
The image of a Black man is so often hypermasculine, and I’m totally not that, especially in the bedroom. There have been people where it was a huge shock to them, or a disappointment to them. Whenever I see someone who isn’t Black and I begin talking to them, I’ll ask them if they’ve been with Black people or specifically Black men before to make sure they aren’t fetishizing me. Because there have definitely been instances where I have been.
When I see women, I love to bottom or be very subby. I saw an older woman once and she actually bought me a shirt and hat that said “pillow princess.” When I see people with penises, I do like to be the dom in that scenario.
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The best sex I ever had was a threesome with two trans masc people. I was seeing one of them and we’d have sex and exchange nudes. They were non-monogamous and they were like, “I showed some of your nudes to my partner and they’d love to see you.” I’d never had group sex before and it was something I was very against. It was actually very upsetting to have my nudes shared with another person. So we didn’t talk for a while, but then one time they were like “I’m out with my partner, come meet us.” And I met with them at a bar and it was phenomenal. The chemistry was so good between us, especially between me and their partner. The person I’d been with before knew I was kind of subby, so they both took my clothes off and ran my face into the partner’s crotch—things just started off pretty hardcore from the jump. It was also my first time double penetrating someone.
When I was in Paris with the person I met there, we were hooking up in the shower. And they were joking, asking if I’d ever peed on someone during sex. I was like, “No I haven't crossed that bridge yet. No golden showers for me.” And they were like, “Do you want to do it?” I was like, “We should probably have a much longer conversation about this before we actually do it.” And they were like, “Just do it.” I did it and I thought it was very hot. They couldn’t stop smiling after I did it. I don’t know how I’d feel about it if they hadn’t really enjoyed it.
I matched with someone in Milwaukee on Hinge, and they said they were solo poly— seeing multiple people, but not in an actual relationship. I drove to Wisconsin, we had an amazing time, I went back to their palace, we hooked up in this small room that was off to the side of their living room. I asked, “Isn’t your bedroom upstairs? Why are we hooking up here?” And she was like, “Don’t worry about it.” So we were hooking up and everything’s going amazing and then there’s a knock on the door to the room. It was her husband and he was holding their baby in his hands and asking her how much longer it was going to be because the baby wouldn’t stop crying. I immediately put on my clothes. If she would have told me, hey I have a husband and we’re polyamorous and I have a baby, that wouldn’t bother me at all. Bu—the shock of that revelation in that moment! Even worse, the husband made weird eye contact with me the whole time—he didn’t even look at his wife! She texted me the next day asking if everything was all right and I was like, “Absolutely fucking not—that was horrible!”
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