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What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? Southeast Asian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Engaged/Married (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)? 50+
How many hookup stories have you here posted before? None

Cub….

How long ago did this hookup happen? 19 years

What was your relationship status at the time? In a relationship (monogamous)

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? Let’s call her L. I found L on an online “dating site”. I was browsing and came across her profile. She was 52 at the time and had a nice G-rated picture on her profile. I message her, not expecting her to write back. Instead we ended up having a long conversation – what started as a casual “hello” ended up with her planning to come over to my apartment later in the evening. L was an average looking woman, brunette and on the heavier side. I was a 21 yr old horn dog – ready to fuck anything that moved.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? As mentioned, the seeds were sown in the chat session. She was very horny too. I asked her if she was okay with the age difference and she said she didn’t care. So we decided to move ahead. I gave her my address.

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? L knocked on the door around 7pm. I was nervous, had showered and shaved (even my pubes) and was ready for her. I opened the door and saw a short woman of about 5’1″ or so, short brownish hair, wearing a shirt and trousers. She came in and I offered her a glass of water. After she was done drinking, I asked her if I could hug her. She gladly embraced me and I could feel her breasts press against me. She didn’t let go. I took that as a cue and kissed her. She responded passionately and we kissed for several minutes as our hands explored each others bodies. I unbuttoned her shirt and saw her nipples straining against her black lace bra. I pulled down her bra and sucked on her nipples. That got her very excited and she quickly undid her pants and mine and started stroking my cock through my underwear. We had both had it with the courtesy and quickly undressed and jumped into the bed going at each other’s bodies. She wasn’t shaved but was freshly showered and I enjoyed eating her pussy. After 2 orgasms she took me in her mouth and we did 69 for a while. I loved her pussy and ass sticking into my face and she came a 3rd time.

I quickly flipped her over and shoved my cock inside her wet pussy. We fucked in a couple different positions till I finally came.

We lay in bed for some time. Didn’t talk much – mostly small talk and how great it was.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We exchanged our good byes. I contacted her a couple days later. She was nice to chat with but said she felt awkward fucking someone around her son’s age. It ended well. We never connected after that. But still today I remember L fondly and the lovely sex we had that evening.

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

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? Very

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. I don’t share my sexual activities with anybody I know.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Eating her lovely pussy and feeling her pussy pulsate as she had her orgasms

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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? Wish I could meet her more often. She was my first older woman. For a while I went through a phase of only having sex with women much older than me.

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? Casual sex is necessary in everybody’s life. Humans are not built for monogamy.

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

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