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What’s your gender? Man
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? NYC
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Self-Employed
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? 3

A Moment

How long ago did this hookup happen? 10 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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

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 K. She was a good looking older woman. Blonde hair, nice skin. We met at a low key bar. My friend was DJ’ing and I was sitting by myself and all of a sudden this woman comes over and asks if I wanted to talk. I was a little taken aback, but went over and we started chatting.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were flirting for a most of the evening. She knew I was young (I looked it to), but she was amazed at how young I was (19 at the time). As the drinks kept coming we went back to her place and made out for a while. Had fun. We planned to get together a week later for maybe something more

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 went back to her place a week later. We ordered pizza and were just hanging out watching a movie. I instigated us drinking shots of vodka and we both got quite drunk. and were making out. It got a little more physical and I started to take her pants off. I picked her up and took her to her bedroom. We put on Cheap Trick and I stripped her down. She had a trimmed bush and very perky nipples. I went down on her and she was very wet. I was quite aggressive with my fingering and quickly got three fingers inside her. I put one in her ass for a little bit, but she wasn’t enjoying ti so much and playfully told me to “get out of there.” I pulled her up and made her kiss me. She was a little shy about kissing me after I had just gone down on her, but she quickly enjoyed it. She sucked my cock for a while and played with my balls. She had great technique and we then switched to a 69. as soon as she plated herself, her pussy just opened and presented itself right in my face. I started to lick her again as I gazed at her beautiful and natural white asshole. I spread her cheeks apart and started eating her ass. She told me beforehand she wasn’t into anal play, but I could tell she was really enjoying this. I turned her over on her back and fucked her in missionary. Her pussy was being very responsive to my cock and we switched to a few different positions and I finally came on her tits and mouth. It was a hot moment.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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? I woke up early in the morning around 7. Fingered her again and she blew me one more time and again I came on her tits. We had a lovely shower together and we were both a bit hung over. It was odd. She told me a few things during the evening that stuck with me. Her husband had died less than a year beforehand and I believe I was her first physical contact since him. She appeared lonely and probably wanted to be with me for my youth and company. I was a bit crass about a few things as me only being a sexual hookup. I told her to call me, but I never heard from her again. I deleted her numbers from my phone soon after for whatever reason. I think well of her and hope she has found happiness.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Intoxication

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

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? Very

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.

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? Not at all

What was the BEST thing about this hookup? great oral sex from her and the absolutely beautiful pussy and asshole I got to eat. I wish I could see it again.

What was the WORST thing about this hookup? Not pursuing it further.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? no.

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

All things considered, how NEGATIVE was this experience? Not at all 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 enjoyed it when I did it. The early days were the most fun and it got old after a while. I’m happy I did what I did when I did it. I have no desire to cheat on my partner as I did everything I wanted to do before I got to her.

What do you think about the Casual Sex Project? It’s great and wonderfully informative.

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