Totally Unexpected



What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 19

Totally Unexpected

How long ago did this hookup happen? 1 year ago

What was your relationship status at the time? Engaged/Married (monogamous)

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

How long did you know the person before this hookup? Just met that day

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? I’ll call her S. She was tall and slim in her late 20s. Pixie cut, with a subtle confidence. She was pretty but got prettier as you talked to her. She had small but perky breasts, milky skin, and a firm sporty ass.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at a group dinner organized by mutual colleagues and friends. No planning was involved. I was visiting from out of town for work and there was a lot of booze involved. I’m pretty sure I instigated the innuendo, but she made the first move.

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? After the big group dinner, we got beers and drank them in the park. We’d been chatting all night and ended up focusing on each other. I’m married (happily, but have different opinions in monogamy than my wife, secretly, and with some guilt) and she had a boyfriend who was out of town. As our conversation became more intimate and I became more honest and vulnerable she began to drop hints, subtly at first and then overtly, that she wanted us to hook up. We ended up kissing in the park furiously and I invited her back to my hotel room. She accepted. I don’t go outside of my marriage very often, and have never been much of one for one night stands. I think I brushed my teeth when we got back to my hotel and she was sitting on the edge of the bed. We started making out again and slowly undressed each other. It was either the booze or nervousness about being with someone so soon after meeting them but I had a hard time getting it up initially. I haven’t used condoms with my wife in years and every time I put one on I would go soft. We went back to oral and went down on each other individually and then I asked her if she was ok with 69, which I love, and I ended up coming in her mouth. My oral skills are dynamite with my wife but I’m not sure it was great for my new friend. After that, we fell asleep and I left a note telling her not to sneak out in the morning. We woke up a few hours later and crawled into bed with each other. I had no problem getting it up this time and we had some nice morning sex that started with me on top and turned into her riding me. She was very vocal, moaning, and bracing herself against the headboard, almost screaming as I sucked on her tits. She went faster and harder and I tried to hold back, but we had run out of condoms, so we were fucking raw and I lost out to my biology, pulling out and cumming in her ass. She seemed really disappointed and asked if I would go down on her, but my oral skills didn’t seem to do the trick. We got coffee and said goodbye and I haven’t talked to her since. I’d love to, but worry about getting caught.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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 got coffee in the morning nearby and walked a bit. I think we were both feeling guilty for cheating. We said a nice goodbye and haven’t chatted with each other since. I’d love to hook up with her again but don’t know when my work will take me back there or if she’d be interested.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, Condoms, I don’t know if my partner was on any (other) method

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Intoxication, To feel better about myself, To feel more desirable, I was feeling lonely, Making new friends, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

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

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

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one. Ever.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? A little bit

Why do you regret this hookup? I don’t like cheating but I also don’t believe in physical monogamy. I’ve told my wife that but she feels differently. I would be happy for her to sleep with other men as long as it didn’t jeopardize our family unit.

What was the BEST thing about this hookup? Too close to call between coming in her mouth during 69 or the sound of her moaning while she was riding me. Those two things, but also the feeling of being desired, of connecting with someone quickly, of being spontaneous.

What was the WORST thing about this hookup? Post cheating guilt and existential questioning.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Made me realize a bit more that I don’t really have a strong attachment to monogamous ideals.

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

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

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 learn from everything. Meeting, getting to know and experiencing the joy, rush and uncertainty of sex with new people is a way to learn about life and yourself.

What do you think about the Casual Sex Project? Turns me on, freaks me out, occasionally bores me.

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