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What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? Black
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Information Technology
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? 0

First time bareback

How long ago did this hookup happen? 1997

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Friends-with-benefits

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

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? Let’s call her Mary, 20 at the time. She was a Canadian white female from a well to do. Short brown hair with a “boy cut” style. Dark brown eyes. Slightly above average height at about 5’7″. Average build, about 125 pounds. D cup breasts. Average “standard issue” booty. Trimmed but hair covered muff. I knew her from her working at an upstate NY University student center and a class we shared at said university. We had good casual conversations for months, but nothing more than that until the hookup.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was living off-campus in my own place. She lived in her apartment across the Canadian border. I had no roommates at the time. She wanted to stop past after her shift ended to “hang out”.

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? She jumped in my shower and emerged from the bathroom wearing one of my t-shirts and nothing else, leaving no doubt about her intentions. We go right to my bed and after some deep french kissing, I went to her impressive natural boobs, sucking her nipples. At the same time, I used my hand to gently rub her pussy. After a few minutes of this, she was dripping wet, and I was a rock hard 19 year old bull. I reached over to my dresser to grab a condom (this was the 90s, AIDS then was a very serious concern, for me, more so than getting someone pregnant, so up until this time I was tested often and religiously used condoms) she then tells me she’s clean and on the pill and desperately wants to “feel me”. My Alpha bad boy won out over the careful gentleman, so I obliged. She gets on top of me and slides my rock hard bare cock inside her. At this point, I’m not going to lie that I performed like a porn-star. I didn’t. I was totally unprepared for the heightened sensations from unprotected sex vs the safe sex i had been having with only one partner prior to this. So, I blew my load inside her less than 2 minutes later. I did make up for that by recovering quickly and getting her off a few minutes later. The feeling though of shooting rope after rope of your seeds inside a wet, tight, bare pussy for the first time is a wonderful memory that is as clear now as it was nearly 20 years ago.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? After the hookup, she stayed the night, showered, had breakfast together and later I had sex with her a couple more times at her place across the border. She even introduced me to my first experience with (her receiving of course) anal sex and deep throating. Unfortunately, it turned out she had a boyfriend on campus, so I wanted no part of that rodeo, and we parted ways. I can’t judge her too badly though, because I was in a long distance thing at the time as well. I think about her from time to time. Unlike a lot of my friends and associates from college, she seems to have vanished after transferring to another university, even in an era of social media. I hope she’s doing well, wherever she is.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Everyone else was/is doing it

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? 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? I didn’t talk to anyone about it. Even then, I kept my personal life personal (when we guys brag, it hurts your chances for future fun, just saying…) Although, some friends suspected I hooked up with Mary.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Cumming inside a woman for the first time.

What was the WORST thing about this hookup? My early explosion in round one.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This gave me the experience of sex the way nature intended, not far after I started having sex just a year earlier. Still, throughout the years, with very few exceptions, I remained very careful using protection, especially casually.

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? Casual sex for me is exploring to find what you enjoy and training for serious relationships (the sex part anyway).

What do you think about the Casual Sex Project? Its a good place to talk about past experiences that would otherwise be uncomfortable to talk about with a current spouse.

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

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