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What’s your gender? Man
How old are you? 35
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? California
Highest education received: Some college (not currently in college)
What’s your occupation? Brewery
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 3m 8f
How many hookup stories have you here posted before? 0

First time catcher

How long ago did this hookup happen? 15 years

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? He was about 55, about my height, grey hair, glasses. I originally met him at my work and we became good friends. I didn’t know he was gay at first, but it helped my decision to ask him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had just had dinner at a nice Italian restaurant and he dropped me off at my place. I was recently single, horny as hell, and curious about gay sex. I called him. He told me to come over.

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? I got to his place. We shared a bottle of Capt. Morgan. Needless to say, I was fairly intoxicated. I asked him again to screw my ass, meanwhile, standing up and dropping my pants, presenting my ass to him. He stopped me and said we should go to his bed. He had me bend over his bed while standing. I loved exposing myself to him. He was very gentle, fingering me with copious amounts of lube before I finally begged him to shove his cock in my butt. Again, he was very attentive, and slowly his cock entered me. Finally, he slowly started to screw me, and eventually, I was getting pounded into his mattress. I kept begging for it “Pound my ass, I want your cock!” With one last shove, his cock erupted into the condom. He was a great lover. He wanted to suck me off after, but I couldn’t get erect.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? Yes, one

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? My butt was sore the whole next day. Otherwise I probably would have loved a round two that night. I didn’t have any expectations of a future with him, though he and I shared more nights later on.

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

How intoxicated were you? Drunk/high but not wasted

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? 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? No one for a good long time. I had a girlfriend up until about a year ago that loved hearing about me bottoming for men.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? I wish I hadn’t been so drunk.

What was the BEST thing about this hookup? I lost my gay cherry.

What was the WORST thing about this hookup? The pain of the initial penetration.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It really did, though I still consider myself straight. I would hook up with a guy again if the cards were right.

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

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

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? For me, sex with men is casual, and very infrequent. I prefer my relations with women to be geared more toward a relationship.

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