What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? UK
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 30

First Time Gay Anal Sex

How long ago did this hookup happen? 10 years

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a week

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? Met on a gay discussion forum (well, really a place to hookup). He was an older (mid-50s) married male working away from home in the city where I lived and had his own flat. After talking back and forth for a few days I agreed to come over to his flat late at night. He was medium height, a bit stocky, middle-aged man; I found myself strangely attracted to him, something about him being older and confident perhaps.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been curious about bi sex and met a couple of guys for mutual wanking and tried oral a bit, but nothing more. I wanted to try to receive anal, as I fantasized about it a lot, but fear of contracting HIV made me very reluctant and careful. When I met him online he seemed very safe, married and stable, and so I thought it would be the right person to have my first experience with.

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 turned up at his flat and he opened the door wearing a t-shirt and casual trousers; I had come straight from work having worked late (it was around 9 pm). We chatted a bit and then he hugged me and I hugged him. St the time I didn’t fancy kissing men so we didn’t kiss but he held me tightly and stroked my bum which turned me on. I don’t really remember how it happened, but quite quickly we got undressed and he was feeling my cock, and I his; it was very large and I got slightly worried about whether it would fit. I kneeled and started sucking him, it felt very natural, and I loved the taste. We quickly moved to the bed and sucked each other in a 69, I had been sucked before a bit but this was far more intense. Eventually, he asked me if I wanted to be fucked and I said yes. I laid down on my back and he lubed me up and put on a condom, and then began to enter me. I hadn’t expected it would be so difficult, but it was quite painful at first; he had to go very gentle. It took quit e long time before he managed to penetrate me fully and for the pain to subside, but once he was in all the way I started to enjoy it. He was on top of me and I wrapped my legs around him, feeling his very large cock inside me and holding him I felt a wonderful sense of fulfillment I hadn’t expected. After a while of fucking, it started to hurt a bit so I told him he had to come, and he did quite quickly – it was very exciting to see his face as he climaxed inside me and playing with myself I came very quickly myself. Afterward, as he pulled out I felt a bit weird as if my intestines had been pushed around and I had to go to the toilet for a while. We got dressed and chatted a bit, and then I went home.

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 a bit weird about the whole thing as I now had fully crossed the line into gay sex, but at the same time, I felt very excited about it. Unfortunately, it turned out he had crabs and I got them too so a few days later he called me to tell me about it – he was mortified as it had never happened to him. I wasn’t upset about it but it was a bit awkward to go to a pharmacy and buy the treatment – the salesperson clearly guessed I was gay and was a bit snotty – but it was simple enough to treat so didn’t bother me too much, but it did put me off the whole thing for several months. Eventually, we hooked up again and it was better, I slowly began to learn how to relax a bit when he entered me so it was less painful. We met every few months on and off for a couple of years until I moved away. I’m glad I had that experience with him, he turned out to be a decent and gentle guy and it made me realize I was fully bi, and I’ve had multiple bi or gay partners since and would do so more if I weren’t married. Still trying to come to terms with being a bit submissive and liking to receive anal while at the same time enjoying heterosexual sex where I’m the active partner.

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

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

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? It made me realize and appreciate my bisexuality and that I am more passive when it comes to gay sex

What was the WORST thing about this hookup? The initial pain and that I got crabs!

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

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

What do you think about the Casual Sex Project? Great idea

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