by: D

Gender: Male
Age: 28
Race/ethnicity: Hispanic
Current location: California
Highest education received: Some college (not currently in college)
How religious are you? A little
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? No.
How many sexual partners have you had in your life (including oral sex)? 17
How many hookup stories have you here posted before? None.

California Cougar

How long ago did this hookup happen? Two years ago.

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Short fling.

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? Sexy cougar (mature woman) with a nice body. The first time we met was at my favorite bar. I was shy to start talking to her at first, but once I did I knew something good would happen.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went out for drinks at my usual bar, and I saw her sitting there. She was looking good. She was wearing a tight little top with a small jean mini-skirt. I knew I wanted to try and get something going. I went up to her, and we started talking for a little while. I noticed that the bar was closing soon, so I waited outside to see if she was leaving with anyone. She left alone. As she walked by we chatted for a bit, and I asked if I could walk her to her car. She said “Yes” and we went down the street for a few blocks. She was parked in the dark corner of some parking lot under a tree. She invited me to smoke some weed with her, and I took her up on the offer.

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? We sat in the car for a while, just talking and getting to know each other. She told me that she was very open-minded. I asked her what she meant by that, and the put her legs on my lap, smiled and said “Sexually.” After that we started kissing. I put my hand up her skirt and started rubbing and fingering her. After a short while, she invited me back to her place for the night. When we got there, she asked me if she could suck my dick without a condom. That made and nervous, so we had regular, protected sex for a while. First was missionary. She felt amazing. She also squirted a lot. I’d never experienced that before. It was strange but it turned me on at the same time. After that it was doggystyle. She encouraged me to try anal with her, and I did. That was the first time I did that. After that, we stood up. I bent her over her bed and started fucking her from behind. She loved that. She kept squirting so much that it was running down her legs. I felt an orgasm coming on. I asked her if I could cum on her, and she said, “You can cum wherever you want.” A few minutes later, I pulled out, took my condom off and came all over her back. She went to the bathroom to clean up. She came back and we fell asleep on her bed. The next morning we woke up and started talking. I wanted to have sex with her again but I didn’t know how to instigate it. I started touching her and she said, “You can fuck me whenever you want.” That was all I needed to hear. She laid face down and we had sex for about half an hour. After that she turned over and masturbated for another 15 minutes or so. We took a shower and spend the day together. About a month later, I saw her at the bar again. We both had too much to drink so neither of us could drive, so we ended up having sex in her car. I was nervous that someone would notice, but I kept checking outside of the window and no one was there. The sex lasted almost an hour. I came inside her, and it was one of the most incredible orgasms I’ve ever had.

Did you have an orgasm? Did your partner(s)? Yes, both of us.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I wore condoms the first two times we had sex, but not the third. We both get regularly tested. I got tested a month after we last hooked up and the results were clean.

What were your REASONS for having this hookup? I honestly only went out for drinks and usually only hang out with my friends and people that I already know, but I was alone that time and felt strangely attracted to her even though I’d never seen her before.

Were alcohol or drugs involved? If so, how much? We had a few drinks and smoked a little weed as well.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I moved out of state a few months after our last hook up. I still have her number, and we talk from time to time. She gave me an open invitation to stay with her whenever I’m in town, which is pretty cool.
To whom did you talk about the hookup? How did they react?: I’ve never told anyone. I don’t talk about my sexual history, even with my closest friends.

Was this a consensual and/or wanted experience for you? For your partner? Yes, it was consensual for both.

Do you regret this hookup? If so, why? I don’t regret it at all.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about this hook up was the sex, of course. Also I should mention the level of comfort I had with her.

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

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

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