by

What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: College degree (eg., BA, BS)
What’s your occupation? writer
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)? 16
How many hookup stories have you here posted before? 2

My First Cougar

How long ago did this hookup happen? 15 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

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? Brenda (not her real name) was in her early 30s. Me being 23 at the time, she was a cougar to me. I don’t remember her exact age, but there was 8-10 between us. We’d met on Adult Friend Finder, the only success I’ve ever had (and maybe anyone ever had) on that site. She was a heavy-set gal, with nice tits, and to this day, the horniest woman I’ve ever met.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We’d been messaging for a little while, and she had told me about her many hookups. It seemed like she’d fuck anyone. Being fresh out of a relationship that ended badly and in my early 20s, when she told me, “I can’t wait to have a 23-year-old penis inside me,” I wasted no time getting over to her place. Once there, we hung out and talked for a long time. She had a graveyard shift gig at a newspaper, so her hours were weird. I think I went over around 11pm and left past 4am.

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? Not much happened at first. We talked and talked, which was a little disappointing, since she had indicated this was a sure thing. Not wanting to leave without making it worth my while, I told her she’d gotten me really horny and that I was going to masturbating in the car on the way home (23-year-old me was not the suavest). She said I could do it there, so I undid my pants and started jerking off sitting on a chair in her living room. That’s when it finally happened. She asked if she could give me a blowjob, as watching me had turned her on. I wasn’t about to say no, especially considering the state my dick was in. She gave great head and I came in her mouth.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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 went home happy. Brenda and I saw each other a few more times. Her apartment wasn’t too far from my school, so I went over one day between classes. She wanted to watch me jerk off again, so I obliged. In retrospect, I could have made an attempt to make it sexier, but hey, this was her thing.

The third time I saw her, it was a rainy afternoon. She put on some porn, we made out, and she was horny almost instantly. She stood up, said “let’s get naked” and we did. She went down on me, and then positioned herself for doggy on the couch. Two things happened here: 1) I caught wind of a smell I didn’t like, and 2) she said it was okay to go in raw, since she was on the pill. Given the sexual history she’d described, I insisted on a condom. She got on, laid on her back on the couch, and I got on top of her. We fucked for a couple minutes before I came way too fast. She was disappointed, and asked if it was my first time. Jesus, the humiliation.

After that, I didn’t contact Brenda for a while. She texted me a couple months later, saying she was in a bind and needed a ride to work. I was reluctant, especially considering what had happened the last time I saw her, but then she said “I’ll make it worth your while” and that was all I needed. I headed over to her place, and we sat and talked for a while. She said she’d had a sunburn, and asked me to put some lotion on her back. This got her going, and as soon as I was done, she asked “Wanna fuck?” Remembering what happened last time, I said, “How about you go down on me first?” and she begrudgingly obliged, sucking my dick until I came in her mouth. I don’t think this was what she had hoped would happen. She got up, got ready for work, I drove her there, and that was that. Never saw her again.

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, Thought it was an important experience to have, To feel better about myself, To cheer myself up, I was feeling lonely, It was easy / convenient

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? 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? Until now, I’ve never told 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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? If I’m being honest, I wish we would’ve fucked as she wanted that last time. Also, this woman was more of a freak than I’d been with, so I feel like I could’ve experimented a little. But I was still hung up on my ex, and just not experienced.

What was the BEST thing about this hookup? The ease with which it happened; getting to experience an older woman.

What was the WORST thing about this hookup? Not taking full advantage of it.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I think in all honesty, this did not improve my attitude toward sex. I’d only slept with two women before her, and one was a serious relationship. Had I not had sex again until I was with someone I cared about, I feel that I could’ve been more mature in later sexual situations. Instead, I feel like I almost expected it to be this easy and was disappointed when it wasn’t.

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

All things considered, how NEGATIVE was this experience? A little negative

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

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

Story Views: 3,728