Sex Lives: A Guy Who Once had a Woman Dress Him Up Like a Schoolgirl

I once had sex with three people in a 24-hour period. A girlfriend of mine had dumped me. I basically became what my friends called a hurricane of bad decisions. Someone I was on a recreational running team with had been flirting with me for about nine months and now that I was available, she wanted to sleep with me; I slept with her. And then about 18 hours later, I got a cold phone call from my ex’s best friend who had been interested in me as well, and I slept with her. And then my ex came over and initiated make-up sex. My ex never found out that I slept with her best friend. We all used protection; I was responsible. There was a time gap and everything, but yeah, it was very confidence-recovering. I felt very desirable.

I’ve only come from sex ten times; usually I have to finish myself off. I usually just can’t come, so we just continue to have sex for insert period of time. One occasion it was like twelve hours. I wasn’t hard the whole time. We took breaks. We got water. I was 19 when that happened and there was a perverse pride like, “She will never forget me.” As I’ve grown older, I’m less inclined to try to do that. Usually after two or three hours, I’m like “This is just a thing that’s a problem for me. I’m gonna finish myself off.” With long-term, more-committed relationships they usually start to push like, “What’s the deal? Why am I not enough to push you over the edge?” I can try to convince myself that this is an advantage, but really I vacillate between general acceptance, and profound insecurity about what this does to someone that I sleep with.

I’m not currently sleeping with anybody, but there are about three to five women that—how do I say this without sounding ridiculous? I write them smut. I haven’t slept with or even met up with all of them. When I was about 24 or 25 I realized that my dirty message game was pretty good. Women I was sending erotica to would continue to reach out to me, and they’d brag to their friends and then their friends would ask me to send them erotica. When I’m getting to know someone, and what they’re into, I’ll first just send a kind of boilerplate story that I have in my notes app. And then from there, get feedback and then tailored to the more it’s very direct. 

I don’t know what happened, but in the past couple years I’ve been really finding the fetish of breeding very arousing. Suddenly a switch flipped in my brain. It’s something I put in the boilerplate. And from that I’ll figure out like, “Oh, you’re not into breeding you’re more into, money shots on the breasts or you want a facial,” and then my writing will shift to fit their wants. 

One woman I dated, then we broke up, and now we kind of hook up through erotica. Another woman is a friend of a friend who was posting terminally horny pictures on her instagram stories and we got to a place where I send her erotica now. Sometimes I get to the stage where I’m sending erotica to someone I’ve been talking to on Tinder. We didn’t really work out but every three weeks they reach out for it, and that’s when I’m very apathetic. It’s like, I don’t know you, you’re not incentivizing me. You’re just showing up out of the blue like, “Tell me what you’re going to do to me. I’m alone right now.” It’s three o’clock on a Tuesday, can we not? There should be a modicum of decency. Like, start a conversation. “How are you doing blah, blah, blah. Have you seen the song? You should go check out this movie.”

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Tyler in Kansas City talked to GQ about early online dating, older men, and an unfortunate allergic reaction. 

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