Bob The 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? Everything goes
How many sexual partners have you had in your life (including oral sex)? Many
How many hookup stories have you here posted before? Several

Bob The Virgin

How long ago did this hookup happen? 30

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

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

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, stocky, slightly chubby, married, good looking, clean, round larger butt. We became good friends, we and the wives socialized.
At first, he was not on my list to have sex with, I am totally in the closet except with those I am 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. We often went to lunch together as well as happy hour after work.
We had to visit our employer’s job sites around the country at times and often together. 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 & 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’ assholes and also 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 pussy then eat them out, he said he liked the taste of his cum. I asked if he ever ate his cum when jacking off, he said he did. I started my seduction planning at that point.
So one night after work, we went to a bar and started drinking. I pretended to, wanted a clear mind. He got a buzz on and I then started to hit on him.
I told him I had the same desires. And did he ever fucked or suck a guy? No, he said. I said that I did. He got very interested. I told him that I did it often with several friends that I had.
I said let’s leave, it’s late. We got out to the parking lot and I asked him into 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, swallowed his load. He thanked me and said it was the first from a guy. I said would you like to fuck a guy’s ass. Yes!

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 to a motel. As we undressed, I notice 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. 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 & started riding. After a few humps, he stopped it because he wanted me on my belly, 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. 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 is a full-fledged bisexual leaning towards gay. On our 3rd date, and the 1st on my back, as he was plowing me, I pulled his head down for his 1st 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), Hoping or expecting it would lead to something more

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

How intoxicated was your partner? A little tipsy/high

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? I don’t know / I’m not sure

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

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 new cock & butt

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? Be discreet

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? Great

What do you think about the Casual Sex Project? Interesting, furthering my education. Would like to eat the doctor’s pussy.

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