First Gay Sex

by Robert

What’s your gender? Man
How old are you? 67
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Some college (currently in college)
What’s your occupation? Retired (construction)
What’s your current relationship status? Engaged/Married (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)? 14
How many hookup stories have you here posted before? None

First Gay Sex

How long ago did this hookup happen? 6 years ago

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Short fling

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

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? He was husky, but strong and toned and around my age, early 60’s. He had a belly but no fat rolls and a robust and barrel-like body with some tattoos. We’d never met in the flesh but had emailed back & forth including soft-core photos of each other. We met at his home; I was nervous and very excited to meet.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had met at a classic car show, and I asked him about his ride which was for sale. We exchanged email addresses there, and over the next month realized we were both interested in having sex together. I drove across town to his place, late in the morning. I took a Cialis on the way.

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 was nervous but very excited at the same time. I was shaking actually, as I stood at his door. As a much younger man, I’d been picked up and gently seduced by an older guy, who sucked me off. I never touched him, but fantasized about it (and masturbated to the fantasy) for 40+ years.
I liked him immediately; he was quite forward but pleasant. We chatted for a few minutes in the living room before moving to his dark, cozy bedroom where we stripped. He knew I was married (he was separated from his wife) and that safe sex was critical for me; oral with condoms and no anal.
He and his wife were swingers, and during their years in that lifestyle, he’d sucked many men off which was a great joy for him. But he assured me that as a newbie, my limits would be respected and that this was my morning to do as much or as little as I liked. We hugged as we stood naked next to his bed, and I sat on the edge as I admired his big penis. It was 7″ and very hard without being touched and a strong upward bend. His belly and balls were shaved; I’d trimmed for him as I knew he liked it. I’m pretty sure I moaned aloud when I first took his erection into my hand, and soon I was pumping away on his dick, massaging his balls, and getting up the nerve to taste him. My first taste was the bottom of his hard-on as I ran my tongue from base to tip, and then I quickly swallowed his cock, wild with the taste and texture. He laughed easily over my extreme enthusiasm and fed me as much of his erection as I could get down my throat. I choked a couple of times, and soon we laid down in bed, where I continued to suck him (I don’t think I ever let his penis go as we moved) and where we eventually moved into a 69 position. We lay on our sides, and I nearly came with the first warm touch of his mouth on my cock. It was quite likely as sexy a thing as I’d ever done, like a snake eating its tail, and I couldn’t get enough! After a bit, I told him I couldn’t hold off any longer, and he turned around to slip between my legs, taking me deep into his mouth again. My orgasm lasted a long time, very intense as he kept me on the edge until I bucked against him and came in his mouth. He didn’t work too hard at it, just kept my penis deep in his throat as I came, holding my balls as I growled and moaned in pleasure. He slowly licked me clean as I caught my breath, and I asked him if he still wanted to fuck my mouth, something we had discussed earlier. He moved on top of me, (I was propped up on pillows) and slipped a rubber on his still hard penis. He had agreed to wear a condom for me – as much as I wanted to taste his cum I was concerned about keeping it entirely safe. His cock bounced and danced in the air right in front of my face as he slipped the rubber on, and then he moved up onto my chest as he slipped into my waiting mouth. I was so into it I was getting hard again already, slobbering and gurgling on his cock as I sucked him, and as he fucked my mouth with ever-increasing power.
I never could deep throat him, but I used my hand to control his penetration and after some time (5 minutes?) he told me he was going to cum, and I pulled the condom off to watch him ejaculate. His semen pumped out onto my chest and neck, and while I was hoping for a lot of jizz there wasn’t that much; oozed-out rather than ‘pumped’ is probably a more accurate description. Still, I could feel his semen running down my neck onto the bedding, and I was so fucking hot again it is indescribable.
We cleaned up a bit in the bathroom, and he laughed as I came back to his bed hard again. He lay next to me and watched as I stroked off, and using a bit of lube I climaxed quickly again.
He had to get back to work, and we hugged goodbye standing in his driveway.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 pretty good. It had gone better than I expected but I felt a little guilty that he had sucked me to climax while I basically jerked-him off, but I got over it.

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, Emotional intimacy, closeness, connection, Thought it was an important experience to have, To feel more desirable

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

To whom did you talk about the hookup? How did they react? No one.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? That we were a good fit, and that we responded so fully to one another. A very good random coupling!

What was the WORST thing about this hookup? That it didn’t go farther into gay experimentation. But I’d set the limits, which he cheerfully agreed to.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes.

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? I’ve hooked up with a few other men since, as ever for safe sex only. This 1st guy was the only one I sucked bareback; generally, I’ve tried to keep these playtimes to mutual masturbation and outercourse’ (once)

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’d love to be more daring, but I won’t take chances with my wife’s health. I would also enjoy meeting another married, cautious man for more intimate play. Someone that knows he’s HIV neg., and that I could trust completely. I see the attraction to casual, and/or anonymous sex, but am not in a position to practice it.

What do you think about the Casual Sex Project? Excellent work!

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