What’s your gender? Man
How old are you? 57
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: College degree (eg., BA, BS)
What’s your occupation? IT
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Very
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

Three Friends

How long ago did this hookup happen? 38 years

What was your relationship status at the time? Single

How would you best classify this hookup? Group sex

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 a pretty, shapely brunette with larger than average boobs and a natural bush. He was a dark-complected Caucasian, maybe of some Native American descent. She was my ex-girlfriend’s brother’s ex-girlfriend, a friend, and a former co-worker. He was a friend and former co-worker. I liked her as a friend and was a little flirty with her at times, and she was with me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My buddy and I went to the movies and saw her there. After talking a little she invited us over to her place after the movie.

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 all smoked a little weed and started playing cards. It turned into strip poker, but we couldn’t get her roommate to play with us. After we got naked, the loser of each hand had to do what the winner wanted. I lost and she won, so she said “5 minutes in the bedroom.” I had to walk past my buddy while sporting a full woody… I started to go down on her but she wouldn’t let me, so I climbed up and slid into her – my first time! Damn, she was so warm and wet, and her pussy gripped my rock hard dick so nicely! I gave her a good fuck, then we went back to the card table. Next hand my buddy won, so he took her back to her bedroom for 5 minutes. While they were back there, they came up with a plan, and when they came back out they talked me into a threesome in the bedroom. We had to ask her roommate to sleep in the other room as she wouldn’t join us.
It started off by both of us guys kissing her all over and playing with her tits and pussy. Then she put me on my back and started sucking my dick while my buddy fucked her from behind. She had me just to the point where I was gonna cum, but just then she had to tell my buddy to stop fucking her so hard. Then he and I swapped places so she was sucking his cock while I fucked her from behind. She wanted a double penetration, but at that point, neither of us wanted to go up her ass (ahh, missed opportunities…). So we decided to fuck her one at a time, and I went first. I ended up fucking her the rest of the night while my buddy waited in the other room. It turns out she had wanted to be with me the whole time we were dating our exes (the brother and sister), and begged me not to tell my ex we had hooked up. My buddy and I had zero contact with each other through the whole experience, and in fact, I think I only saw his dick once – normal, with a big mushroom head. We all called it a night a little before sunrise.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? I tried to get a relationship going with her after that, but she was not willing. I was kinda torn up over it for a few weeks – she was my first partner, after all – but a sweet thing at college made me forget about her. She turned into a full-on slut after that, but I would still like to find her and see if she turned out OK.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, 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), Learning new things, experimenting

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol, Marijuana, hashish

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

What substances did your partner(s) consume? Alcohol, 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? 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? My buddy, who was part of it. He thought it was pretty cool, too.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? Somewhat

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 would rather my first time had been just me and her.

What was the BEST thing about this hookup? She was hot! 18 years old, big tits, and she sucked my dick!

What was the WORST thing about this hookup? Missed opportunities (double penetration), it was a one-night stand.

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? Somewhat positive

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Thought about it many times since.

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 think it’s overall a negative influence. Sex should be reserved for that one special person. Back then, I was all for it and wanted as much as possible!

What do you think about the Casual Sex Project? Interesting.

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