What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Scientist
What’s your current relationship status? Single
Religious affiliation: Agnostic
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)? 65
How many hookup stories have you here posted before? 0

Two in one day

How long ago did this hookup happen? 2 years

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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 50, and dating a 23 year old Caucasian girl I’d met on Craigslist. She was a bit of a head case, a bit chubby, nice full breasts, waxed, fairly tight pussy, fun wild child. We’d been dating about two months and were planning to go out Saturday night (I thought – apparently we had actually planned for Sunday). Come Saturday night I couldn’t reach her so I felt angry (silly of me) and went back to Craigslist. I met a 32-year old Korean woman and we met in a bar.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She walked in the door and I was smitten. Maybe 5’4″, beautiful slender body, great smile. We had drinks and chatted. She let it be known she didn’t go to bed on the first date. This of course was a challenge to me. I played it cool, became pals, shared life stories, touched her arm (and she mine). Eventually she said I could sleep over but no sex.

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? At her place I caressed her (clothed) body for about an hour, slowly got us both undressed. She was totally hairless, slender, with b/c cups that had been enhanced. Beautiful face and long black hair. After about an hour of foreplay and my giving her oral, she became more and more aroused and receptive. Eventually I put on a condom and fucked her missionary. In the morning (maybe 9 am) we had a long mutual oral and touching session followed by her riding me cowboy. When I got home I was still so excited that I jerked off thinking of her.

That day (Sunday) my 23 year old girlfriend called me and said ‘hey, what shall we do tonight?’ That’s when I realized she hadn’t stood me up the night before. We had dinner and somewhat bland but satisfying sex consisting of mutual oral and cowboy.

I was stunned that at 50 I could fuck two girls and orgasm four time between midnight Saturday and 9 pm Sunday. Honestly didn’t realize I was still able to perform at that level – although of course these two young sexy girls were great stimulants!

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 kept dating them both without telling them about each other for about two months. The white girl was fun but the sex was a little bland. The Korean girl loved multiple positions, submission, spanking and just generally being sexy as hell. Both relationships ended because they wanted something more serious.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), To cheer myself up

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? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I told the story once at a dinner party when we playing a confessions game

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Finding out I could seduce and please two much younger women in one day

What was the WORST thing about this hookup? Wish we were still FWBs but that isn’t realistic

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

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

All things considered, how NEGATIVE was this experience? Not at all negative

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