What’s your gender? Man
How old are you? 43
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Teacher
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)? 13
How many hookup stories have you here posted before? 0

Workplace Shenanigans…

How long ago did this hookup happen? 7 years ago

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

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

How long did you know the person before this hookup? For more than 3 years

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 and I had worked together for a few years. She has a killer body (great ass, in particular), killer smile and illuminating eyes. We started chatting over Facebook in a little more provocative way, and one thing led to another….

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After chatting on Facebook and indicating mutual desire, we ended up going to an after-hours work event with our spouses and children. Spouses left with kids and we went with other friends to the bar. I’ll never forget rubbing each other’s legs at the bar in front of our friends and colleagues. I took her back to her car and we hopped in my truck. She knew I loved her pinstripe pants, whose stripes met perfectly in the crack of her ass and told me “I ha e a surprise for you,” and led my hand to her underwear and asked me to guess the color. Ended up black with stripes. We held each other and kissed, but nothing else that night….

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? As time moved on, we touched each other all over. She jerked me off, I fingered her. We made out at work (in school) often, she rode me and I can still hear her telling me “I want to fuck you so bad…” Unfortunately, that never happened. I did get a few blowjobs from her and someday hope I can go down on her.

My wife was pregnant during this adventure and immediately after my son was born, things slowed down and Michelle ended up with a much older man, which totally devastated me. I pretended to understand, but I still want to fuck her and think about it often seven years later. We remain great friends, but she and her husband moved a bit too far to allow anything to happen, which stinks.

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 felt guilty because I was married, nervous that guilt would make her tell her husband and scared to be caught with my pants down at school.

I would have left my wife for her. She’s an amazing person and very passionate.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, To feel better about myself, To feel more confident

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? 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? Nobody.

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? Very

Did your partner get emotionally hurt as a result of this hookup? Very

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Emotional connection, risk, and a huge cumstain on the floor of a classroom at school.

What was the WORST thing about this hookup? The way it ended.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. We are the only monogamous species. I’ve strayed again from my marriage, and while I’m trying to get out, the sex is amazing, and I keep lookibg for other opportunities. I’ve fucked 10 women’s and would like to get to 20 in the next 7 years (I’ll be 50 then).

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

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

Anything else you want to add about this hookup? I’d do it all over again, and push harder to penetrate her.

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? Easy to see why people stray. I don’t condone it, but understand. I had a vasectomy and will practice safe sex with future partners.

What do you think about the Casual Sex Project? Great!

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