First Bisexual Affair



What’s your gender? Man
How old are you? 68
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Arizona, USA
Highest education received: Some college (not 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? A little
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 2

First Bisexual Affair

How long ago did this hookup happen? 5 years

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

How would you best classify this hookup? Fuck-buddies / Booty call

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? We met online at C.L. when it was wide open. His brief ad asked for a J.O. partner; I sent my info and he responded with ‘come on over’. He was quite a bit younger than me, (10-15 years) which is not really my thing, but in this case, it worked out well. He was small & trim; I’d describe him as an aging twink, quiet, and a bit reserved.
We played at his apartment; it was a daytime hook-up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I responded to his ad seeking someone to stroke off with. We both wanted the same thing.

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? While I was pretty nervous waiting at his door, he was friendly (if a bit reserved) when he welcomed me inside. At his suggestion, we sat on the little sofa in his living room. There wasn’t much talking at all, we just sort of started touching and caressing. We were dressed in loose, light clothes, so exploring was easy. He was soon obviously hard under his shorts, without even being touched – a huge turn-on for me.
After a bit, I slipped my hand inside the waistband of his shorts to touch a large, very erect penis.
I was hard by this time as well, and he rubbed me through my shorts. We undressed, lifting up to slip out of our clothes. He had a truly gorgeous cock; perfect.
We moved to his bedroom, where we continued to make out. We kissed – I’d tried kissing a man once before and found it distasteful. My new friend kissed ‘like a girl’ I guess you’d say; soft and easy.
He knew I liked to watch & be watched, so we stroked off side by side, using the coconut oil he kept on his nightstand. Eventually we moved to mutual masturbation and as usual, it was very exciting, if a bit awkward.
After a few minutes, he told me he was going to cum, and he did (immediately) as I jacked him. It was an incredible orgasm, unlike anything I’d ever seen. His semen squirted onto his face and chest, covered his belly, and my hand. I have a cum fetish and couldn’t believe his ejaculation! I came just a moment later as he jacked me. I’m pretty talkative during sex, but he was pretty subdued. Other than that he was a lovely, sexy playmate.
After cleaning up a bit (I took a shower) and chatting for a while back in the living room – he was far more talkative after we’d had sex – I was hard again and he sat close to me on the sofa as I masturbated to a second, very intense orgasm.

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? We said goodbye at his door, and I was completely delighted. I felt fine the next day, and couldn’t wait to hook up again. I was married of course (to a woman; 30+ years) so we had no plans for a ‘future’ together, but we made tentative plans to meet again, and we did a few weeks later.
We saw each other on & off over a 2 year period. Maybe a dozen times, always at his place. He’s moved on, but I miss him and am still VERY fond of him.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, Making new friends

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

What substances did you consume? Marijuana, hashish

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? 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? His warm, if reserved intelligence, welcoming home, trim smooth body, and beautiful penis. My bi experience is limited. I’d been with 5 or 6 guys before this hook-up and none since. He is the only man I’ve played with that I would have considered spending the night with. Although we kept it ‘safe’ sexually, he could have had me anyway he wanted me. Within reason.

What was the WORST thing about this hookup? He was so quiet during sex! He moved around and was physical enough, but seldom spoke. In the dozen or so times we were together he rarely (maybe twice?) told me that he was getting close, or was about to climax. Of course, since we didn’t suck bareback, it didn’t really matter, but I really like dirty/sexy talk.

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

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? It was so sensual and hot! I wish I’d been less concerned about absolutely safe sex, and experimented more. As the only guy I’ve met that I would consider a ‘lover’, it (he) was the perfect opportunity.

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? All good. I rarely feel even fleeting guilt, mostly because I’m quite cautious and won’t take chances with unsafe sex. My wife knows that I’m bisexual and is good with that; I don’t have to lie. What would I like changed regarding casual sex? As a well known gay author of humor recently said, a cure for cancer and AIDS would be nice, so that a person could enjoy a cigarette after a steamy bit of anal sex. I couldn’t agree more.

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

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