Best Night Of Sex In My Life



What’s your gender? Man
How old are you? 55
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Province of Québec
Highest education received: College degree (eg., BA, BS)
What’s your occupation? IT Consultant
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
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)? Around 100
How many hookup stories have you here posted before? None

Best Night Of Sex In My Life

How long ago did this hookup happen? 11 years ago

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? She was a semi-cute woman in her young 40s; I think she was about 42, and I was 45 then. She had a well-maintained slim body, perky chest, and a nice butt. We met on a dating site, had a few chats prior to the first in-person meeting, and then came our first “date.” We went to a coffee shop first and then to a pool room, where we had a couple of drinks, but not too much.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I cannot say that there was much flirting between Celine (her real first name) and I. It was mostly cerebral during the evening. I knew, talking to her, that she was not really my type, intellectually. But it was okay. Eventually, it got to the point that it was getting a bit late. Since I was living not too far from the pool room, I offered to go to my home for a last coffee. I had nothing to lose anyway; I figured the worst case was she would decline. But she accepted. When we got to my home, I decided to open a bottle of wine instead of serving coffee, which she accepted gladly. That’s only then I thought that I might have a real chance.

We sat on the couch, and I turned the TV on to a music channel. The wine started to kick in for both of us. I put my left arm around her shoulder, and she did not react. Then, peeking at her chest, I realized that she had nice tits – not big, but perky, a good B cup. I slowly let my left hand down from her shoulder to her left tit. I thought that if she did not like it, then she would say so. When I reached her left tit, I gently started massaging it. That’s when she turned her face toward me with a kinky smile.

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? It took a minute or two before I removed all of her clothes, but then I went down on her. Her pussy was perfectly shaved. She came in 5 minutes or so. After that, I undressed and sat on the couch again. It was her turn to go down on me. She sucked my dick. Her blowjob technique was not the best, but I came in her mouth nonetheless and she swallowed all of my cum, to the last drop. After, we went to my bedroom. We started making out, and I got hard again. I fucked her missionary at first, then we went doggy. She came again in that position. That’s when I thought that this woman was quite naughty. So I said to myself, let’s fuck her in the ass; I’m sure she’ll accept. And so I did. I removed my dick from her vagina and slowly pushed it up her Hershey alley. She didn’t say a word. Obviously, I came in two minutes.

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? Nothing, we never saw each other again. I was not really interested in her, and I know she could feel it. I think she was fine with just having sex that night.

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? 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? 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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Well, I got a full blowjob and I fucked an ass on a first date. How can I ever beat that again?

What was the WORST thing about this hookup? That it has never happened to me again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really. I was lucky, and I knew it.

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

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

Anything else you want to add about this hookup? I wish I could repeat. There were a few instances after that when I got a complete blowjob and engaged in anal sex on the same night, but it was with a regular GF that I was with for 6 years. It happened 3-4 times with her.

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 don’t see it that often. I have had multiple partners in my life. But in almost all cases, sex would happen on the 2nd date (if the 1st date went well). I think I had sex on a first date only during the experience I described here. So my “score” is something like (finger in wind kind of estimation):
– Sex on the first date: 1%
– Sex on the second date (if the first date went well): 94%
– Sex on the third date or more: 5%.

What do you think about the Casual Sex Project? Very cool, very exciting.

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