by Dave

Gender: Male
Age: 27
Race/ethnicity: Caucasian
Current location: Chicago
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Student
Relationship status: Single
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 0

Age Gap

How long ago did this hookup happen? 5 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand

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? Michelle was 33 years old, brown haired, freckled, gaunt, but not in an unhealthy way. I met her on the field at the Brooklyn Bridge Park one summer evening, where we had both gone to watch the film Raising Arizona. She was by herself. She looked alone. Not necessarily lonely, but at some place where she generally felt alone. She glanced over at me when I sat down near her. After a minute, she asked me what time the movie was supposed to start.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began in the basement bedroom of my aunt’s house, whom I was house-sitting for at the time. I was very lonely and anxious this summer. I was nearing the end of senior year in college. I had broken up with a girl the previous fall. I had been with another girl shortly after, who I had been attracted to for years. She broke my heart by deciding that I wasn’t her type and ignoring my further advances. So that summer, while doing an internship in New York, I felt sexually frustrated. I was watching a lot of porn. I would say I had some issues with women. These issues would continue for another several years, but that’s another story. 
I instigated the actual hookup, although we mutually laid the groundwork for it. After the movie–during which we’d talked a lot and drank wine, and I’d met a couple of her friends–we walked back through Brooklyn to my aunt’s place. We stopped at a bar for a beer and afterwards she was acting very tipsy. As we walked towards the house, she stopped and kissed me. Keep in mind that she was 33 and I was 22. I’d told her that I was 23, which is the most useless lie I’ve ever told (though I hadn’t expected her to say she was 33). After we made out for a little bit I asked her if she wanted to come inside. She was reluctant. Her idea had been to spend some time with me and get on the train. But I persuaded her to come home with me.

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? We lay on the couch in the living room, making out. I got her shirt off and slid one hand in her pants and fingered her. She wore a green bra. I had trouble unhooking her bra, so she giggled and did it for me. I kissed her tits and she breathed heavily and occasionally laughed, as if in disbelief that she’d allowed herself to be seduced by a guy who was so much younger than her. She got very wet, but at one point put her hand on mine and asked me to slow down and chuckled. I slowed down and sucked on one of her breasts, exploring around it with my tongue. She sort of stroked my head and let out a loud gasp. 
Shortly after this, I stopped fingering her and she put an arm around me and said, “Where’s your room?” We went downstairs and lay on my bed and kissed some more and I got her pants off. I asked if I should put on a condom. She nodded anxiously. I opened my top dresser drawer and took out my condoms and rolled one on. Seeing me at my dresser gave Michelle the idea of fucking on top of the dresser. So she sat there, now completely naked and I guided myself in to her. I held her back and her legs squeezed my waist. It was very awkward and uncomfortable. The dresser shook and I slipped out of her. I said I’m not sure if this works too well and she agreed. She lay horizontally on the bed propping several pillows under her and I have this image of her lying on her back, legs spread, her vagina red and messy, reaching towards me as she said “come here…” I got down on the bed and with her help slid my cock all the way inside her. She gasped loudly when I entered her and I remember thinking, “Jesus. I don’t even know this girl.” She moaned for a little while and I kept telling myself, “Don’t cum too soon. Make her cum.” Of course, neither of those goals panned out. I came quickly.

Did you have an orgasm? Did your partner(s)? Yes. She did not, at least not during intercourse.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did not discuss STIs. I half-hoped that she was on birth control. Maybe she was, but she still wanted me to use a condom.

What were your REASONS for having this hookup? I wanted a 1-night stand. I’d never had a 1 night stand before and wanted to prove that I could do it.

Were alcohol or drugs involved? If so, how much? Some alcohol. I don’t think either of us were ever drunk. I think her tipsy thing was an act.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I cuddled with her for a few minutes, although I felt completely weird. I remember her sort of squirming around on my bed giggling to herself, naked, while I removed the condom. Later, I walked her to the train and said goodnight. I got her number. The next day I felt really ashamed.

To whom did you talk about the hookup? How did they react? My friends who came to visit, and later, friends back in Boston.

Was this a consensual and/or wanted experience for you? For your partner? Consensual. I think she was not necessarily planning on a one night stand, but then, I didn’t expect one.

Do you regret this hookup? If so, why? I did at first, but I don’t now. I think the sex wasn’t that good for either of us, but I did call her a few days later and she was completely amazed that I had called. I felt guilty about lying and told her my real age. I don’t think there’s anything wrong with what we did, and I kind of wish I had kept it going (I think she was open to this, without seeing anything long term). But I was going through a troubled phase back then.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing was knowing that I was capable of doing this, and feeling good about being with a much older woman. The worst thing was my fearful attitude towards the whole experience. I kept watching porn in the months after. Michelle was the last woman I had sex with for a long time.

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

All things considered, how NEGATIVE was this experience? A little negative

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