First Time Taking A Man Anally



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? United States
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Marketing
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 1

First Time Taking A Man Anally

How long ago did this hookup happen? 1 year

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

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? I was in Melbourne for a business trip and paid a visit to a gay bath house that was across the street from my hotel. I had been there before on a previous business trip, but had never done anything. It’s an interesting set-up with lots of dark corners, a sauna, hot tub, jacuzzi, private rooms, and gay porn blaring. My first visit was a combo of young Asian men and older men. During that first visit, I sat watching porn while being stroked by younger men and they asked me if I wanted to fuck them, but I declined. I have had several encounters with men over the years, mostly mutual oral and stroking, but it never transpired to actually fucking. I am a Dom/top so were that to be the case, I would be the one doing the fucking. I do not identify as being gay, and to be honest, I don’t identify as bi. I identify as being uber sexual and finding pleasure in whatever manner I can find. The lure of the gay bathhouse was not necessarily for sexual release, but because of the taboo nature of it. The sounds, the smell…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On this last visit, I was wandering around with a towel around my waist, looking in on rooms, etc. until I went down a corridor and stumbled upon a guy on his knees sucking off another guy while others watched. It was a huge turn on, so I watched, while rubbing my own cock under my towel. Along came this smooth guy of Indian ethnicity. He was maybe around 30, and he stood next to me and started rubbing my cock. I nodded my approval, and he dropped to his knees, took off my towel and started sucking on my cock whle sniffing poppers. Meanwhile, I am watching the other guy unload into the mouth of his sucker while a third guy watched both of us and started stroking. I held the head of my partner and started fucking his mouth. At one point, he took my cock out and said “Do you want to fuck me?” and I said, sure, why not.

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 went into a private room and closed the door and he climbed up on the bed and presented his ass to me while applyinig lube to it. Meanwhile, I applied a condom to my cock and lubed it up. He asked me to go slowly as I have a thick cock. He raised his ass high and spread his cheeks apart to reveal his opening. My cock went in very easy, much easier than my own wife. It did not take long before I was thrusting inside him with my balls slapping against his ass. There was a mirror to watch. I asked him if he liked having my big married cock inside of him and he moaned his approval.

After a bit of time though, I was not that into it, and I wanted to go back to him giving me head. I pulled out and took the condom off and told him I wanted him to suck my cock. He said, in a thick Indian accent, “Do you want me to eat it?” and I said yes. I laid back on the bed and he started sucking me off. After a few minutes, I grabbed the back of his head and fucked his mouth until I was shooting spurt after spurt of hot cum down his greedy mouth, and he eagerly swallowed every last drop.

Afterward, I cleaned up, went back to my locker room and retrieved my belongings, and walked back across the street, sexually satisfied.

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? There was a small sense of guilt. I am a happily married man with a very satisfying sex life and a very sexual partner. We have had some incredibly sexual experiences over the years to include MFM, sex in public, BDSM, etc., but she would not support this side of me. So I felt bad, for a short period of time, over that. The next morning that guilt was gone as I woke up with a hard on thinking about the previous night and stroked out a huge load into my hotel room sheets.

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? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? I don’t know

What substances did your partner(s) consume? Poppers (Amyl Nitrate)

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? Shared in some online forums with tremendous jealousy.

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? I got to experience another man’s ass for the first time, and found out it wasn’t my thing.

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? Nope

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

All things considered, how NEGATIVE was this experience? Not at all negative

What do you think about the Casual Sex Project? I fucking love it.

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