What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? CT
Highest education received: Some college (not currently in college)
What’s your occupation? Manager
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Jewish
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)? 16
How many hookup stories have you here posted before? 0

Business Trip One Night Stand

How long ago did this hookup happen? 12 years ago

What was your relationship status at the time? In a relationship (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 had just met her 2 days earlier at a conference in Michigan. Let’s call her S. She was shorter than me (I’m 6ft) had big round breasts, a very nice ass, dirty brown hair, blue eyes and a nice smile. She was very attractive, had a great smile and some sort of southern or Midwestern accent that I really liked.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The conference started on a Monday and a bunch of us went out on Wednesday night to a local bar to drink and play pool. We met a bunch of Canadians in the bar (who could drink) and we drank with them. At the end of the night, we all caught the last shuttle back to the hotel the conference was in. I was traveling with my assistant, let’s call her B. She was attending the conference as well. After the bar one of the conference attendees, S, invited us up to her room to watch a movie. B reclined on one bed and S and I on the other to watch a Disney movie. I think I fell asleep. When the movie was over B left and S and I cuddled up, spooning. I’m not really sure who instigated it. I guess she did.

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 put on some hotel porn and I started getting turned on. I started rubbing my junk up against her ass and fondling her breaks over her shirt. As we kept watching, she reached back and started rubbing my dick with her left hand. I started to kiss the back of her neck and unbuttoning her shirt. While still in the spooning position, she started to unbutton my jeans and take my cock out of my underwear. Then she got up, took off her shirt and bra and pulled down my jeans and underwear. She got between my legs and put my cock in her mouth. I have I slightly above average sized penis and she took all of it into her mouth. I took off my shirt and then started to unbutton her jeans as she kept sucking my dick. She got up and took her jeans off and slid off her thong. Before I even had the chance to play with her, she climbed up and slid herself down on my cock. Had I not had some booze in me (and been really tired), I probably would have cum immediately. Instead, she rode me like crazy. First up and down and then back and forth grinding into my pelvis. When she came, she grabbed and squeezed her boobs which caused me to explode inside of her.

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? We slept naked together and woke up late. I RAN to my room and showered and got dressed and she did the same in her room. We called each other so we didn’t walk in together making it totally obvious that we had hooked up. When I slipped in to the meeting room my assistant could totally figure out what happened. I spent the next 2 nights of the conference trying to get it to happen again but I just couldn’t put it together.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Not at all

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? I didn’t tell anyone. This is the first time I’ve ever “said” anything about it. Ever.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex was really good. I didn’t expect it at all. I think about it still from time to time when I’m masturbating.

What was the WORST thing about this hookup? I cheated in my girlfriend at the time. (We eventually broke up).

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m glad I did it. I had a good amount of casual sex between relationships. I think they helped me become a better lover.

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

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

Anything else you want to add about this hookup? I REALLY wish we could have done it again during that trip.

What do you think about the Casual Sex Project? Cool website.

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