Online Hookup

by Just havin fun

What’s your gender? Man
How old are you? 50
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? Professional
What’s your current relationship status? Engaged/Married (open)
Religious affiliation:
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)? 50+
How many hookup stories have you here posted before? 0

Online Hookup

How long ago did this hookup happen? 5 years

What was your relationship status at the time?

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

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? We met online on a dating site. She was attractive but a bit plain looking. Not really my type since I prefer a bit “trashier” look. I did tell her this so there were no surprises. We did a lot of online chat so we knew quite a bit about each other. She was a very sexual person, but as I said, a bit plain for my taste.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had no real plans to meet her in person, but she insisted on meeting. We did live a distance away from each other, so I agreed to pay her travel costs as well as hotel bill. I told her that I would meet her at the hotel bar the evening she arrived and would take her for dinner and drinks.

I was quite surprised to see her as she looked completely different, and almost didn’t recognize her. Apparently she took my likes to heart as she was dressed in a very short miniskirt, stiletto heels and a low top. In all honesty she was a real head turner.

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 had a nice meal and proceeded to the bar for drinks and flirting. I put my hand on her leg and she slid it up so I knew she had nothing on under that skirt which I of course liked and it gave me an instant hard on. I slipped a finger in her and saw she was literally dripping. She pretty much knew how hard I got from this. It turns out she loved exhibitionism so this just turned her on more.

I asked for the check and we went to her room. We did everything from oral, to nearly every position including trying anal for her first time which she wasn’t sure she liked too much but was a trooper. She did let me know before hand she was a massive squirter and believe me nothing in that room was dry when we were done!

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? She stayed or a few days and we basically did nothing but drink, eat and have sex

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Withdrawal, Sterilization, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more

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? 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? Friends…I was going through a rough time and they all felt I needed it

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

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? Amazing sex

What was the WORST thing about this hookup? She turned out to be a little crazy, and if she wasn’t it might have lead o something more.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all

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? I’ve always been a proponent of casual sex having been in an open marriage.

What do you think about the Casual Sex Project? I think it’s a great outlet and love reading others experiences

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