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? none
My Asian Cougar Experience
How long ago did this hookup happen? 9 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? Helen (not her real name) had messaged me out of the blue on a dating website. She made it very clear that she wanted to hook up. Being in my 20s and horny, I wasn’t about to say no. She was mid-40s, Asian, short, overweight, with fairly large breasts. One day she said she had gotten a hotel room for us before we’d even met. I decided not to go (had a weird vibe), but she kept pursuing it. She insisted she’d never gone down on a man before and wanted me to be her first. I didn’t believe her, but I also wasn’t going to turn it down. Finally, a night came when I knew my roommate wasn’t coming home and I invited her over.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met her at the door of my apartment building. She was shorter than I had imagined, wearing a red suit-like thing with a short skirt. She had fairly nice legs, toned and freshly shaved. We went inside, sat on the couch, and talked for a little while. Since it was out in the open what we were there for, I put my hand on her thigh and kissed her. She didn’t waste any time putting her tongue in my mouth and my hand went higher. After a few minutes of this, she wanted to take it into my bedroom. I wasn’t saying no.
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? Once inside my room, she immediately stripped down to bra and panties. I laid back and true to her word, she pulled my dick out and started sucking. It didn’t seem like her first time, but I wasn’t complaining. After a couple minutes of her giving me head, I took her bra off and got a look at her big tits. She laid on her back as I started sucking on them, positioning myself between her legs, pushing my still-hard cock against her.
She asked if I had a condom. SHIT! I wasn’t prepared. Idiot! She said, “You don’t have to use a condom, just don’t cum in me.” I nearly blew my load right there. I’d never had unprotected sex before and as tempting as it was, I wasn’t about to start with someone I met an hour ago. So I went into my roommate’s room and found one. Even ribbed (for her pleasure)!
I came back with the condom, put it on, slid into her, and pumped away. This was my first time having sex in a couple years, so it didn’t last long. I came after a couple minutes of thrusting (I know! but I was 26 and in a dry spell), and finished. She seemed happy at the time, even if she didn’t cum.
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? We ended up hooking up 2 more times. Both times she came over when no one was home. The second time, she blew me until I came in her mouth and said, “next time, it’s my turn.” I was happy to oblige. The third time she came over, I went down on her and she said she wanted to come with me still in her. She rubbed her clit and came hard while I fucked her, which was super hot.
I never saw her again after that. I think she wanted more than to just get together and fuck every once in a while, but I wasn’t into it, since she was 15-20 years older (never did find out exactly) and not the best conversationalist. A few months later I sent her a text late one night trying to hook up (I never said I was a good guy in all this) and she was like, “Who’s this?” I realized she’d deleted my number so I just wrote back, “Sorry, wrong number” and that was that.
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, I was feeling lonely, Boredom, 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? I don’t know / I’m not sure
Did your partner(s) consent to this hookup? They gave enthusiastic consent
To whom did you talk about the hookup? How did they react? I’ve never told anyone. Weeks later my roommate asked me if I had taken the condom. Being very single at the time and only having this hookup in private, I answered with, “No, who would I have used it with?” Little white lie, but there were other roommate-related issues with him. That’s neither here nor there, though.
How would you best summarize people’s reactions about this hookup? I didn’t tell 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? Not at all
What was the BEST thing about this hookup? I’d always wanted to have sex with an older woman, so I fulfilled that fantasy. She’s also the only Asian woman I’ve had sex with to date, and not to treat intimacy as a score card, but I can check that off a list of experiences.
What was the WORST thing about this hookup? I would have liked to gotten more experimental, since she seemed game. The sex was fairly vanilla.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Years later I thought about her in a new light and felt some remorse since I think she either thought we had something, or was hopeful for it. But since I didn’t really know her that well outside of sex, I can’t say for sure.
All things considered, how POSITIVE was this experience? Fairly positive
All things considered, how NEGATIVE was this experience? Not at all negative
Anything else you want to add about this hookup? I do think about her sometimes while masturbating. I wouldn’t mind reliving that experience somehow. Like a time machine!
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 wish I hadn’t felt like it was so taboo. My roommate at the time, and other friends I’d had, were a little judgmental when it came to casual sex, so I felt like I had to have hookups in secret.
What do you think about the Casual Sex Project? I love this site!
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