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What’s your gender? Man
How old are you? 41
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Missouri
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Military
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 200+
How many hookup stories have you here posted before? 0

First Anonymous Guy

How long ago did this hookup happen? 11 years

What was your relationship status at the time? Engaged/Married (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? He was a white guy, 6ft+, dressed casually, but probably a white collar professional by day; not heavy, but not muscular either, very clean. We had never met before. Before the hook up I didn’t have any thoughts. I was horny and just wanted to fuck.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began on AFF (before Grindr). We chatted for a couple of hours, teasing and sending pics. My ad was for bottoming and he was a top. Our roles were clear.
I played with guys from my teens into my twenties, but never considered myself ‘gay’. I would have been closeted at the very most. Before this actual meeting, I hadn’t played with a guy for 5 or so years. I wanted it bad.
We decided to meet on a back road between our two cities. He was older (50-55) and did most of the guiding and suggesting when it came to the meeting. When we met it was about 11 at night.

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 met in our vehicles and the drive to a more remote location but not far. We got out, exchanged greetings and within 10 seconds he unzipped his pants, took his dick out and pushed on my head in a gesture to suck him. He was soft – which I loved – and thick even then. I knelt on the ground on both knees and took him into my mouth. He was hard very quickly. He told me then and several times throughout that I gave great head. After a short time of me sucking him, he started fucking my mouth. He was thick while soft and thicker while hard. His dick was fucking my throat, but I continued.
He then told me to stand up because he wanted to see my ass. I dropped my pants to my ankles, and he pushed me against his truck but bent over. He then started eating my ass. This was the first time this had ever happened to me. It was incredible. After doing this a bit, he stopped and asked if I brought the stuff (condoms and lube). I got the stuff, applied everything and he made it clear where my place was – which was bent over the tailgate of his truck. He wasted no time placing his very hard and very eager dick at the opening of my ass. He was very gentle during the initial insertion phase and once I had relaxed I told him to ‘fuck me’. And he did.
I’m certain he was married but wasn’t getting something he needed or wanted at home and I was able to fill that role for him.
He fucked me for quite awhile, was very vocal throughout; telling me how dirty I was, how much he wanted to fuck me, how I should be ashamed of myself, and on. I loved it.
When he was closed to cumming he asked where I wanted it and I said on my face. He pulled out, tore the condom off, I sucked him again, and he shot onto my face.
He forcefully kissed me, said ‘thank you’, and left. I never saw him again.
This started me on a journey I continue today.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even 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? I felt great. I was excited. I tried contacting him again but he deleted his account. I would have enjoyed playing again. I have no feelings about them today other than nostalgia.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Submission / Relinquishing power

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? No one

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? The excitement of anonymity coupled with the sexual pleasure.

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? It gave me confidence that it’s ok to not only want sex but the kind of sex I wanted /still want.

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? No.

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 think sex is great, I think more people should embrace their sexual fantasies and desires. Be open to new experiences – safely and securely, of course.

What do you think about the Casual Sex Project? I think it’s interesting and probably very helpful to many people.

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

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