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What’s your gender? Man
How old are you? 53
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Montréal
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Dating casually
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 50 – 60
How many hookup stories have you here posted before? 0

She Agreed to Everything I Wanted

How long ago did this hookup happen? 8 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

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 was newly separated from my children’s mother. I was on this dating website. It was a Friday evening. All the women I was really interested in (my “A” list) on that site were not available to go out. I went to my “B” list. There was that woman, living not too far away from me. I contacted her. She was available to go out. We met for a coffee a few hours later. We then moved to a bar. After that evening, I took her back to her car (that she had left in the café’s parking). I kissed her goodnight on the cheeks after we agreed to meet the following evening, at my place. She was physically ok. Not pretty, not ugly. A nice little body, for a women who was around 42 YO then.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Next evening at around 6:00PM, she arrives at my home. I had set-up a nice dinner (I’m a rather good cook). We ate, had a bottle of wine. I had bought a DVD to watch afterward, because I wasn’t sure how it would go. As we sat on the couch, she gave me a look. What did it mean? I put my arm around her shoulders, she gave me that look one more time. I let my hand go down on her breast. She smiled at me then. And it was “Fuck the movie!”

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 unbuttoned her shirt, removed her bra and started to kiss her nice perky tits. I removed her pants and panties, kneeled and went down on her. She was perfectly shaved so it tasted wonderful. She wanted to undress me as well but I wouldn’t let her. I made her cum with my mouth. I stood up and let her undress me then. We switched position: I sat on the couch and she kneeled in front of me. She took my hard dick in her mouth. Where would she stop? Well, she didn’t. Her BJ technique was not the best, but good enough to make me explode in her mouth. And she swallowed all my cum, perfectly clean, as a real lady should do all the time.
We then moved to my bedroom for another round of fun. We 69 for a little while before I fucked her hard. After a few minutes, she came again. I could feel her pulsating vagina around my dick. But I hadn’t cum. I thought this lady was such a hotty, that I should try my luck. I turned her around, on her 4, and I gently inserted my hard dick in her ass. She let me, but not too deep (she put her right arm behind her, on my stomach, to prevent me from going in too deep). Even if only the head of my dick was in her ass, it was good enough and in her ass I came for the second time.

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 saw her again the following evening, in my home. We had sex, but nothing worth remembering. And I never saw her again after that. I have had my fair share of great sex in my life, I cannot complain. But, still to this day, 8 years after it happened, I can say that this Saturday evening of sex is the most memorable I’ve ever had.

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

What were your motives for this hookup? Hoping or expecting it would lead to something more

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? A little bit

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

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? She would not say no to anything. I had gotten a complete BJ (cum in mouth) on a first encounter before. But never had anal sex on a first date.

What was the WORST thing about this hookup? None

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. It’s just a very good memory.

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’m not too much into casual sex. On that particular occasion, I was really looking for a girlfriend.

What do you think about the Casual Sex Project? Good idea.

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

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