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What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Portland
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Hospitality
What’s your current relationship status? Engaged/Married (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)? 20
How many hookup stories have you here posted before? 0

Manager Training

How long ago did this hookup happen? 6 years ago

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

How would you best classify this hookup? One-night stand

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

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 was in town for 3 days for a company training meeting with all the other hotel GM’s. Every day, the owners would change the seating arrangements, so we would meet new people. The last full day of training, I was placed next to Mary. She never really caught my eye the days prior. She wasn’t my type except for giant boobs. She was almost 40, tall, wore glasses, and was almost in the plus size category. She was receptive to my jokes, and we hit it off immediately. We kept each other laughing the entire day.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In the evening, we all went out for dinner. She kept close, and we kept the laughs going. It was the night before we headed home. After we got back from dinner, the company held a reception for the managers where the alcohol flowed freely. Again, she stayed nearby, and I finally started rubbing her leg underneath the table. The party then went to the bar across the street. More alcohol. Around 1 am, a bunch of us went back to the hotel. She invited me back to her room, and I quickly accepted.

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? In her room, she went to the bathroom, while I headed towards the bed. I immediately stripped off all my clothes and laid there. When she came out, she laughed, and removed her dress. She performed oral on me. Then, it gets slightly fuzzy. I don’t recall if I performed oral on her, but I do recall her pussy being extremely wet when I entered bareback. In my state, I lasted a long time. We did a bunch of positions. She liked to be choked slightly, and I pulled out before I came. I cleaned up. We talked for a bit. Then, we had sex again. She was a bit dryer this time, and I didn’t cum. I headed back to my room around 5 am.

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 felt guilty because she wasn’t my type and because I didn’t wear a condom. It has been 6 years since, and any STD concern has been tested and I’m clean. It was just amazing drunk sex.

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

What were your motives for this hookup? Fun, pleasure, horniness, Intoxication

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not 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? Just her. We still talk to this day. She wants me to come visit.

How would you best summarize people’s reactions about this hookup? Relatively negative

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? A little bit

Why do you regret this hookup? Her best years were behind her, and um, cheating.

What was the BEST thing about this hookup? It was spontaneous.

What was the WORST thing about this hookup? The hangover and the early meeting the following day were the worst.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. Moments like these are fleeting. You have to seize them.

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

All things considered, how NEGATIVE was this experience? A little 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 wish I had more experiences.

What do you think about the Casual Sex Project? A fun read.

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