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This post is sponsored by The T Bar.

What’s your gender? Man
How old are you? 63
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Regina
Highest education received: High school diploma
What’s your occupation? office manager
What’s your current relationship status? Engaged/Married (monogamous)
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)? 12
How many hookup stories have you here posted before? 0

One Night Stand

How long ago did this hookup happen? 23 years

What was your relationship status at the time? Single

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? A bit chubby.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In the days before internet. We had chatted periodically on a ‘BBS” (Bulletin Board System). I had just broken up with my girlfriend of 11 months, when I received a message from this other woman saying I sounded ‘interesting’. We messaged back and forth that night. I offered a massage, and around 3 am, she gave me her address and told me to come over. I wondered if it was a setup, but I was horny, so took a chance.

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 greeted me at the front door, and returned to her computer. I sat on her living room couch and we chatted for a while. I raised my hands, flexed my fingers, and suggested the massage. She smiled and nodded, but remained at her computer.

I stood behind her, massaging her neck and shoulders. After a bit, I slid my hands down her side, feeling the swell of her large breasts. I could tell she was bra-less. She took this as her cue, stood up, and said come with me.

We walked into her messy bedroom, with unmade bed. She turned away from me, tore off her sweatshirt, and laid down on her stomach. I didn’t even get to see her breasts, at least not at that point. I massaged her back, and slowly made my way to her ass, then up and down the backs of her legs, which were still clad in blue jeans.

She mentioned that she was wearing silk panties, and I said I’d like to see them. Still with her back to me, she stood, and pulled off her pants, then went back onto the bed. However it didn’t take long for me to pull off her panties, and she continued to lay on her stomach, but this time with legs spread. I could clearly see her pussy lips. It didn’t hesitate to slide my hand up the inside of her legs to her pussy. She raised her hips slightly to give me better access. She was soaking wet.

I took off my clothes, and straddled her ass, continuing with the massage. Finally I turned her onto her back. Her breasts were saggy, with large brown aureolae. Her pussy was covered in thick black hair.

I fished into my wallet for a condom, and put it on. She re-adjusted herself on the bed, and took my full length into her pussy. She was wet, and loose, and my cock isn’t very big. Still it was great to be fucking a stranger this way. She was really into it, grinding her hips furiously.

I came after a few minutes, and went to the bathroom to get rid of the used condom. By the time I returned, I was ready for more. I put another condom on..this time she sat on my, an with her large breasts drooping down, began sucking on my cock. With hindsight, I should have been bareback at this point, as I don’t think she really cared.

I was good and hard again, and I put her back down, and shoved my cock back into her pussy, and pounded furiously until I came.

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? We met at a gathering of other people. She was very cold toward me. I wanted nothing more than friendship, but she wanted nothing to do with me. This didn’t bother me at all.

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, Learning new things, experimenting, To cheer myself up, I was feeling lonely

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? Nobody

Did you 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? Duh. I got laid.

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

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

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

What do you think about the Casual Sex Project? Love it

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