What’s your gender? Man
How old are you? 49
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Architect
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Enthusiastic and monogamous
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

The Only Casual Sex I’ve Ever Had

How long ago did this hookup happen? 9 years

What was your relationship status at the time? Dating casually

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a week

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She was 17 years younger than I was, tiny, very pretty, very athletic. We met the day before at a three-day yoga retreat. I talked with her at lunch, liked her sense of humor and her nerdy love of obscure music, and was very attracted to her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On the second day of the retreat we were eating lunch together again. She asked me if I wanted to smoke grass. I don’t like grass, but I said yes because I was very attracted to her. It was an intense time in my life: one year earlier, my wife of 16 years had left me without warning or discussion, and I had just started dating a woman I liked (with whom I ended up spending 6 years: I really go all-in), and I felt really uprooted in bad and good ways. Unsettled and free. We got fairly high. Spent the rest of the afternoon doing yoga on neighboring mats. I try to be polite and not check women out at yoga, but I did get pretty much fixated on her ass and her muscles, for sure.

After supper there was a campfire. I play guitar and sing, and there were a couple other musicians there. We played into the evening. Lots of grass being smoked, but I didn’t have any. She seemed genuinely into my music. My friend was very stoned and flirted with her, but she brushed him off. People left to go to bed. For a couple of hours it was just her and my friend and I, still playing music. He finally went off to sleep. I had only ever been with my wife before that, and I admit I had very little idea what was next. I thought she was interested, but I guess I was so adrift in those days I couldn’t be sure of anything. I knew I was extremely attracted to her. She was standing there with her back to me looking in the fire and I stood behind her for a minute, then just thought Well, I’ll regret this forever if I don’t do something. I stood close beside her, then picked her hair up and kissed her neck. It took about two minutes to end up in her cabin under her sleeping bag.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I found eye contact with her almost excruciating. My marriage had been warm but almost sexless. My wife didn’t seem interested in me except as a wage-earner. I think I just got used to being ignored, though I think I’m attractive enough. But here was this woman looking me straight in the eyes and it was the sexiest thing I’d experienced in years. I had just turned 40 and my hands were shaking like I was 15. We started making out. The slowest, hottest kissing. She sat up on the edge of the cot with her back to me and took her top off. Beautiful, muscled back. I stayed under the sleeping bag and got undressed. Still facing away from me, she put her hand in her panties and stroked herself until her back arched. I started kissing her back, then sat up behind her and pushed myself against her. Everything was very slow. I nearly came the moment I pushed against her, but once I stepped back from the edge I settled down. I put my hands on her hips and she arched her back so that her ass pushed back on me. Eventually she took her panties off and lifted up and put me inside her. We sat like that, almost still, for a long time. Finally, she turned around and we faced each other, lots of eye-contact, until I came. That was the most intense orgasm I had ever had. She was much tighter than my ex-wife, and I realized, years too late, that my wife and I just were not built for each other. But this girl fit me so well.

After I came I felt wide awake, exhilarated. I kissed her some more, massaged her. I put my mouth on her and she came almost violently. She made sounds like she was suffering and had me worried for a moment, but when she calmed down a little I went down on her some more and she came again, slower and quieter. Again, all I’d had to compare was my ex-wife, who rarely had an orgasm, and when she did it seemed like an entirely private thing, no sharing, no eye-contact, I was just the cock. But this woman looked me in the eye and seemed so elated and grateful and celebratory I felt giddy.

That was the only time. We kissed for a while the next day, then went to our separate homes. I fell into a long relationship with the woman I’d just started dating. Now I’m in another multi-year monogamous relationship. Just one casual hookup in my life.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We were both a little shy the next day. I hoped to see her again, but then, when I got home, I just didn’t want to. I was very, very intensely attracted to her, and still masturbate to my memory of her, but I didn’t feel any lingering interest in continuing a relationship with her. We saw each other in yoga classes a few times. She was very sweet and kind. Then she moved away.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), I was feeling lonely

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Marijuana, hashish

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? To one close woman friend. She was very happy for me. She had always been very suspicious of, or disapproving of, my years of nearly sexless monogamy, and she told me she was happy for me.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? She was very attractive to me, had a very beautiful body. When she masturbated I was very turned on. Her eye-contact intensified the experience.

What was the WORST thing about this hookup? That I was so sex-starved that I couldn’t last longer. But it was overwhelmingly positive for me.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. It makes me wonder why I’ve been so consistently involved in long-term monogamous relationships when there’s so much pleasure to be found in spontaneous sex with near-strangers.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I think about her often and hope she’s well.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I am still largely wary of casual sex. Most of what I hear seems pretty sad and even scary. The casual-hookup culture does not appeal to me. But my one experience was lovely.

What do you think about the Casual Sex Project? I think it’s challenging to write about sex without falling into facile porno, and I admire the many stories here that keep it very human. Surprisingly poignant.

You have a hookup story to share? Submit it here!