First Gay Experience



What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? United Kingdom
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Retail
What’s your current relationship status? In a serious relationship (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)? 42
How many hookup stories have you here posted before? 0

First Gay Experience

How long ago did this hookup happen? 13 years ago

What was your relationship status at the time? Single

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 had been speaking online to a gentleman who was desperate to try gay sex for the first time. I as a virgin, was also dying to lose my cherry. He was older (by a lot) but I found the age difference a turn on. It was all 100 percent consensual. He had a holiday house we met at. I was very nervous.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I told him how I wanted him to be my first time. We agreed to meet up. However, I chickened out the first time. A week later I tried again and we finally met.

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 am a massive cross dresser and wore my favorite dress. We met and chatted for a bit, then I went to the bathroom and came back just in my dress. I was shaking but it felt so right. I pulled down his trousers and began sucking his pulsating cock. It was about average size but tasted amazing. After ten mins of ecstasy for me, he began sucking my cock and I nearly came there and then because it felt that good. Then, we went upstairs to the bedroom. He lubed his cock and my ass up. I had been using toys for weeks in preparation. He put it in and it felt great. He fucked me for about twenty mins until shooting his load up me. It felt great. Then he jerked me off till I came over the both of us. It felt amazing. We laid there for ages just kissing. Afterward, we got dressed and he drove me home.

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? Felt amazing wanted to do it again but sadly never did.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, Making new friends, It was easy / convenient

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? Told a few. They were shocked over the age gap but was all consensual.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? That was both our first times.

What was the WORST thing about this hookup? Never seeing him again.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Made me very casual about sex

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

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

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 would like less taboos about casual sex especially around females. It annoys me that guys can see who they like, and be called a player but girls would be a slut. It seems a bit unfair.

What do you think about the Casual Sex Project? It’s great.

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