Romping On My Gay Side

by Callum

What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Africa
What country and/or city do you live in? Johannesburg
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Executive
What’s your current relationship status? Dating casually
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Experimental
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? None

Romping On My Gay Side

How long ago did this hookup happen? 10 years

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Group Sex

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 had been sent to another city for a three-month secondment and as soon as I found out I realized that there would be a chance to experiment and I was determined to chalk up as many male lovers as possible. I’d scoped out the gay clubs after I arrived wearing a tight pair of jeans and a shirt that I left unbuttoned to the waist. I was determined to fuck get fucked. It was about 6pm and the evening crowd had just arrived. I felt nervous and stood near the bar nursing a drink. There were two nice looking guys sitting together and I saw them look at me and whisper to each other. One pulled a bar stool in between them and waved at me to join them

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was a bit nonplussed at there being two of them but I felt a rush of heat to my genitals and didn’t hesitate to accept their invitation. They introduced themselves as Daryl and Gerrie and told me I looked a bit lost. I explained I was new in town and had gone to the bar looking for company. Darry said, “well you’ve found some.” They explained that they were long term lovers, versatile and totally non-monogamous though they always told each other about their hook-ups and when possible shared new partners.

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 found them easy to talk to and after two more rounds we headed back to their flat. In no time we were in a cuddle huddle and I felt their hands undressing me. Their clothes also disappeared and before long we were on a double bed and Darryl was guiding my head to his rampant cock. Gerrie was fondling me and kissing my buttocks. The cock in my mouth excited me and I got even more excited when I felt Gerrie lube my ass and explore my virginal hole. I felt totally relaxed, strangely enough, and concentrated on keeping Darryl close to cumming without letting him actually let fly. I felt Gerrie’s weight on me and knew I was about to enjoy my first fuck. I yelped at the slight pain as he pushed into me but as soon as he was inside and his cock head was massaging my prostrate I knew this was for me. Gerrie fucked me slowly at first and I took Darryl deeper and deeper and began thrusting back at my first lover. I felt Gerrie arch his back and felt the heat of his cum in the condom he wore. I was just moaning “so good, so fucking good” and It seemed quite natural that they swapped places and I had Gerrie’s limp cock in my mouth. I was rock hard but amazingly had no desire to cum at that point. As soon as Gerrie had cum I wanted one of them desperately. I didn’t mind which but I had to feel what it was like to plunge into another man’s body and to feel his muscles under me. Darryl lay on his back and pulled Gerrie on top of him and said urgently “fuck him Callum”. I moved to them and my cock seemed to find its way to his hole as if I had been fucking men for years. I loved its tightness and found it far easier to fuck a man hard for a long time without cumming than it was with a woman. We spent the night naked together and I finally went back to my hotel sore but very, very happy.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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 of myself and delighted that I had opened up a whole new world of pleasure. We not only met and played together several more times but they also introduced me to their friends in a very promiscuous circle.

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, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Power / Dominance, Submission / Relinquishing power, Making new friends, Everyone else was/is doing it

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

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? Others in the circle whom I met later. We all discussed our experiences at great length.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Gerrie’s first thrust deep into my body

What was the WORST thing about this hookup? Flying back home.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’m no longer embarrassed about being 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? Because I was introduced to a promiscuous group I was able to share my experiences and this has led me to seek out similar people in my home city.

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 recreational sex is wonderful.

What do you think about the Casual Sex Project? As I have explained, sharing is important.

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