My First Gay Virgin



What’s your gender? Man
How old are you? 60
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Florida
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Engineer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Horney
How many sexual partners have you had in your life (including oral sex)? Many
How many hookup stories have you here posted before? Several

My First Gay Virgin

How long ago did this hookup happen? 30 years ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 3 years

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? Bob was a coworker. He was stocky, slightly chubby, married, good looking, clean, round larger butt. We became good friends and we and the wives socialized. At first, he was not on my list to have sex with and I was totally in the closet except with those I was or would like to have sex with. There was no indication that he liked gay sex. As we got more comfortable with each other, he liked to tell me about his sex life. He liked straight pornography and slutty women. So often had a new story of his latest to tell and would show me some personal photos, of him and his woman sluts. We often went to lunch together as well as happy hours after work. We often had to visit our employer’s job sites around the country at times together but before the hook-up, we took separate rooms.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Later on, he confided about his Cum and Butt Fetish. This got me to change my opinion of him and started my lust for his body. He liked to play with the girls’ ass holes and also to eat and fuck them in the ass. His choice of sluts allowed that. His wife was strictly chaste in that type of sex. He would cum in their pussies and then eat them out. He also said he liked the taste of his Cum. I asked if he ever ate his cum when jacking off, and he said he did. I started my seduction planning at that point.

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?

So one night after work, we went to a bar and started drinking. I pretended to drink and actually wanted a clear mind. He got a buzz on and then I started to hit on him. I told him I had the same desires. He asked if I ever fucked a girl in the butt and I said yes and also guys, actually. I then asked him if he ever fucked or sucked a guy before and he said no. But I said I did and of course, he got very interested. I told him that I did it often with several guy friends that I had and I said it was time to leave because it was late. We got out to the parking lot and I asked him in my car. It was winter. We sat there and I asked if he had a hard-on? Yes! Pull down your pants. He did. His hard cut cock was out, so I went down and started sucking him and swallowed his load. He thanked me and said it was the first from a guy. I asked if he wanted to fuck a guy’s ass and he answered yes.

We went to a Motel. As we undressed, I noticed he was nervous. He was never with a man before. He was not comfortable with all the ways of gay sex. No feeling each other up, no kissing. I can live with that, for a while.
He wanted to fuck my butt badly. I got on my back, legs up and got him into position, then fed his dick into my hole. He fucked me for a few humps, but it was too close for him. So I put him on his back, climbed on, straddled his cock and started riding. No, after a few humps he stopped it. He wanted me on my belly, just like the girls he fucked. OK, I did that, and he gave me a good fuck.
After a recovery recess, which I spent with my hands playing with him, we got into the 69 position and sucked each other off. He swallowed. He likes the taste of Cum. And a little later, with him on his belly, I fucked him. After a few later episodes, he got over his male on male fetish and was a full-fledged bisexual leaning towards gay. On our third date, and the first on my back, as he was plowing me, I pulled his head down for his first French smooch with a man.
30-years of everything goes. And I have shared him with others.

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? Never said anything to anyone, at work or elsewhere. But, on his own, he later hooked up with another guy at work, which of course I eventually did. That’s for another story. Tom & Bob & Me. Later.

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)

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? A 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? Somewhat

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’ but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Nobody

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? A straight guy becomes gay.

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? He goes to places for gay sex, like Baths & glory holes etc.

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? It is great

What do you think about the Casual Sex Project? Interesting

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