Surprised Me



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? Western NY
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? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 14
How many hookup stories have you here posted before? 0

Surprised Me

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? M and I had chemistry from the start. Colleagues in a small school, chatting on Facebook led to interesting questions and conversation.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? First started after a teacher nighttime bowling event that we went to, continued to a bar and ended in my truck with her on my lap telling me about the surprise. She knew I had a thing for her pinstriped pants that cradled her ass perfectly. Lights out in the truck and she says, what do you think, guides my hand toward her pussy and says “what color?” Unsure of what’s going on…”doesn’t really matter…”. We made out and it ended there…for now.

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 continued to get closer, let ourselves go. Lots of kissing and flirting. End of the day, locked doors and more touching and kissing in our classrooms. Many days I would go home to my wife with a stain in my pants… anyway, one day she unbuckled me and goes down on me entirely unexpected. Just as I was about to cum, she said she couldn’t swallow and my load ended up on the floor. Wasn’t the last time… I would often finger her and lick her juices and cum off my hand and always dreamed of returning the favor.

She moved before we could ever fuck, but I still think of that often and hope someday we can follow through with our dream.

How sexually satisfying was this hookup? Somewhat

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? She got a little distant and smitten with an older man. Ended up fucking him, I’m quite sure. Was quite open with me about it, but hid us from her husband for a while….

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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

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? Somewhat

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

Why do you regret this hookup? I only regret that I didn’t go down on her in my truck or fuck her anywhere…yet

What was the BEST thing about this hookup? Great kisser, passionate and knows how to work my cock.

What was the WORST thing about this hookup? Ended. I felt a bit guilty being married and having an affair.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Want more.

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 fell in love with 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? Like it.

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

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