First Hookup Long Ago



What’s your gender? Man
How old are you? 56
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? Process engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
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)? 11
How many hookup stories have you here posted before? First one

First Hookup Long Ago

How long ago did this hookup happen? 27 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? 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 traveling for work a couple times a month to the same plant. After work, I’d head out for a few beers and get to know the local nightlife. One night I visited a new place. It was packed with an older crowd. A DJ was playing and there was some dancing. After sitting at the bar all night, near closing time, a woman I noticed through the night, but haven’t given much thought to, was suddenly tapping me on the shoulder. She asked me to dance.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She introduced herself as being 49 and divorced. She was slender with short blond hair, not all that pretty. However, she had a really nice little ass and cute little b-cup breast. I gave her a brief background on me including the fact I was married and a couple hundred miles from home. Before the second dance ended she gave me a big kiss, gazed into my eyes and asked if I wanted her to be my fantasy for the night.

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? I was very new to this scene and a bit awkward, not to mention I had a few beers. She, on the other hand, knew what she wanted.

We left the bar quickly and she followed me to my hotel. Once in the room, we were all over each other. She asked if I wanted to get naked and we proceeded to take each other’s clothes off and crawl between the sheets.

We engaged in some foreplay and I don’t recall if I went down on her then or not. I got on top and fucked her good in missionary and came hard in her after about 5-10 minutes. Considering how much I had to drink and the time of night I felt pretty good and she seemed satisfied. We then fell asleep.

We woke in the morning and she was smiling. A good sign. I was in much better shape after sleeping and proceeded to play with her tits and pussy getting her all hot and wet. This time I did go down on her much to her delight. Then we fucked in a couple different positions. She was really getting into it and after doggy style, she wanted to be on top which I complied with promptly.

To my surprise instead of straddling my on her knees, she squatted over me and guided my penis into her. She sat and ground away on me until we both came hard. At times having her weight on me like that was almost painful, yet exciting and pleasurable. I know I was getting deep into her tight pussy and she was loving it.

Once we finished we jumped into the shower and played for a while. Then she got dressed and I walked her to her car.

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 felt good. It was always something I wanted to do. She was at least 19 years older than me if she gave me her true age. I kind of always had a desire for older women so this was a plus.

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

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Intoxication, It was easy / convenient

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? Somewhat

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? No one

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The woman had an awesome body and wanted to get laid. It’s always great if your partner is enthusiastic and wants the same thing.

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No. I’ve always thought casual sex was separate from a romantic relationship. Sex is part of both, but casual sex can be purely for physical pleasure.

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? You may not be able to tell from my experience described above, but I am selective. I’ve hooked up a number of times since, but it’s not common for me. Everything from a few one night stands to a fuck buddy I had for five years.

I think casual sex between two or more consenting adults is fine and should not be stigmatized.

What do you think about the Casual Sex Project? I enjoy reading about the different situations that trigger casual sex. It’s good to know it happens more than people think it does and between unlikely partners.

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