First Casual Encounter With Another Man



What’s your gender? Man
How old are you? 50
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? U.S./East Central Florida
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Software developer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Very high sex drive
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? None

First Casual Encounter With Another Man

How long ago did this hookup happen? Three 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? He was stocky, average in looks, and was ten years younger than me. His cock size was on the smaller end of average. We had never met before. I met him through a Craigslist ad that I posted. We met at my home. I didn’t know anything about him except the description he sent me via email.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began in my bedroom. I always wanted to experience oral sex with another man. I was in what I call a “bi-curious stage” of my life. There was some planning involved – mostly about where to meet and what I was looking for. I instigated it.

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? The only sexual act that occurred was mutual oral sex. I gave him a blowjob first. Since this was my first blowjob, I was very nervous about technique and especially worried about scraping his penis with my teeth. That has happened to me in the past when I’ve gotten blowjobs from my female lovers and it can be painful.

At first, I was only using my mouth to please him but after ten minutes of sucking, my jaw was becoming sore and my lips a bit numb so I began stroking him as I sucked. He took longer to cum than I anticipated. He didn’t “shoot” his load but instead it felt like the cum gently flowed out. It flowed over my tongue into my mouth. The quantity was much smaller than I anticipated it would be. The flavor was also sweeter than I imagined as I swallowed it.

After I was done with him, he sucked me off while slowly stroking my cock. The oral sex felt amazing. I had a very intense orgasm and ejaculated a huge load. He swallowed my cum which really made the experience so much better.

We both had a mutually satisfying experience. He was very good at oral sex – probably better than I was as this was my first time. I didn’t talk while sucking him. While I was sucking him, he was asking questions like, “Do you like my cock?” and “You like sucking my cock?”

After it was over, we thanked each other. There was no small talk or other conversation and then he left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

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 proud about going through with my plan to have oral sex with another man but I also felt a little “dirty” and “ashamed”. I met up with him one other time several months later. I didn’t and don’t have any romantic feelings towards him. It was just a brief encounter.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Learning new things, experimenting, Thought it was an important experience to have

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? I talked to no one about the hookup.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Feeling another man’s cock in my mouth, watching him quiver, and hearing him moan when he came.

What was the WORST thing about this hookup? Feeling a little ashamed afterwards.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. It confirmed that I am actually bisexual.

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? I was very nervous.

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 have had many more casual encounters with men but only for oral sex. I wish that bisexuality was more accepted in mainstream society instead of being considered shameful or deviant.

What do you think about the Casual Sex Project? It’s a great place to read about others’ experiences. I really enjoy reading their stories. It’s terrific to have a place where people can share intimate details about their sexual encounters with others.

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