Unexpected Roles Lead to Memorable Results



What’s your gender? Man
How old are you? Late 50s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? San Francisco
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Current relationship is “somewhat” monogamous – no sex outside the relationship, but I sext strangers
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Gay/lesbian
Any other term(s) that describe your sexuality or sexual identity? Everlasting
How many sexual partners have you had in your life (including oral sex)? Hundreds
How many hookup stories have you here posted before? None

Unexpected Roles Lead to Memorable Results

How long ago did this hookup happen? Early 90s

What was your relationship status at the time? Dating casually

How would you best classify this hookup? One-night stand

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? Described elsewhere

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? See my description of what happened

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? Years ago, in my late 20s and early 30s, I was sexually active with a series of partners, lots of them, most of them anonymous and most of them one-time encounters.

One day, I headed (back) to a gay porn theater in San Francisco, one that featured male strippers and encouraged cruising and hookups in private booths, even during the daytime. It was Fleet Week, and I thought it would be exciting to hook up with one or more of the thousands of soldiers and sailors from somewhere in the world. I engaged in my normal cruising prep, which included an enema, soapy shower to make certain I was ready for anything.

When I wasn’t cruising the booth area — where guys would watch porn and masturbate in their booths, waiting for company — I was in the theater part, watching the strippers. The audience members were more interesting to me than the buffed-up pro performers because I usually preferred hookups that didn’t involve money changing hands. The dancers would eventually get “in your face” for tips, and some of the guys in the audience would rub themselves through their clothes, get partially undressed, and sometimes masturbate openly when the almost-naked performers approached them.

The audience was international, and there was no doubt in my mind that some guys were horny soldiers or sailors. Part of the thrill was that some guys seemed amazed that such a place existed, and they were definitely ready to take advantage. I happen to be tall (6’4″), and my sense of curiosity made me zero in on a much smaller (5’3″ or so) guy in the audience — pale, jet-black hair, smooth-skinned, Latin-looking, probably 19 or young 20-something — with an awestruck expression on his face and his hand on his clothed crotch bulge. A handsome dancer gave him an eyeful of bulging underwear package for a minute, but my guy couldn’t/wouldn’t tip the performer’s sweat-sock stash, so that ended quickly.

I remember giving my smaller friend a determined look in the eye, then slowly made my way out of the theater and headed for the booths. In the unlocked booths were a few different guys — including a young, middle-American “straight” dad with his pants down and his cock standing straight up whom I masturbated for a minute — but I was looking for my beautiful dark-haired “prey”.

Eventually, I found him standing in an unlocked booth, his clothes on and a porn video running. The lose quarters, his relatively slight build and our height difference made me seem like a towering giant. I sat on the bench and kissed and nuzzled him gently while he stood; he closed his eyes in the moment and we rubbed each other’s clothed crotches. His lips seemed cold but there was no cold soda with him, which only made him seem more nervous. I tried some conversation, and he knew enough English to say that he was from Ecuador and a merchant marine. In between make-out moments, I said, “Welcome to America,” and with hand signals and English asked if he wanted to walk to my place. I looked in his brown eyes, he looked in my blue eyes, and I got a “Yes” in English, despite the fact that he was (understandably) making mental calculations of risk factors.

We walked to my apartment together. Part of my excitement was the challenge of letting him know — without a common language — that I might look imposing but there was no need to be wary. I remember thinking that his courage was a big turn-on, and I was half-hard because of that alone. I stopped a few times on the way, to point out landmarks and make him feel more safe and less lost.

In my apartment, there was no pretense of being on a date. I showed him where the bathroom was and he said “No,” and we each began to strip right away. His strip seemed awkward and not purposely erotic, which I found sizzling hot. I began to plan an approach, with the intention of making an almost wordless hookup memorable and exciting for my partner. I wanted to focus as much as I could on his needs and wants and looked in his eyes for clues. I decided that I would use my masculine powers to make him feel utterly in control as if I couldn’t help adoring him and submitting to his every need. As soon as I knew that I wanted to fuck him, I mentally turned the tables and knew that I would beg him to fuck me instead.

Once we were naked, every part of him was smaller by comparison — his cock, his feet, even his lips. Yet, everything was beautifully in proportion. I sat on the bed while he stood, both of us with erections, and I rubbed him all over his chilly body (like it was a lifesaving thing), but he ran cold and I ran hot. His face communicated raw need. I was his bodyguard and masculine concubine, and offered him my mouth and ass with pleading eyes. His cock tasted clean and salty, and I made the tightest possible suction with my mouth as I got him to pre-cum.

I was so proud when the eyes rolled back in his head, especially when I positioned my ass sideways on the bed — right by the edge — so that he could stand by the bed and see everything: His cock entering my furry ass, my hard-on, my hairy chest, one of my legs extended straight and the other bent submissively at the knee, and the look of adoration on my face. He had the condom, I had the lube, and I think he couldn’t believe his luck and the power of his uncut cock. He excitedly pumped my ass, and his dick felt really good inside me. I jacked off, and made all kinds of sounds but made myself wait to cum.

He came in the condom as he fucked, and I helped him find the wastebasket. I literally picked him up off the floor and kissed him on the way back to the bed — he wrapped his legs around me for 30 seconds — and it didn’t take him long to get hard again. I let my cock go soft (!) in between fuck rounds, but (during Round 2) the thrill of being fucked with my long legs in the air made my cut cock hard again and made me jack the big load I’d been denying myself until then. He shot another load in his 2nd condom of the day, inside my butt.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We did not exchange contact information, but I felt that we exchanged spiritual greetings beyond the bounds of language. I walked him to the front door, he smacked me on the butt, and off he went into the early evening.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Proper lube

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Emotional intimacy, closeness, connection, To feel more desirable, I was feeling lonely, Submission / Relinquishing power, Making new friends

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 didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Just kept this between me and my one-time hookup friend

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? I learned a new level of sexual and emotional fulfillment, subtle but profound. I had bottomed many times, but this was about learning to give joy to my partner in unexpected ways.

What was the WORST thing about this hookup? I always feel a sense of regret (among other things) after sex, because sex has a tendency to push lots of emotional buttons. That doesn’t mean I don’t feel other things, but I think it’s healthier to admit this part too.

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? In my mind, I guessed this was his first time with a man, or maybe another kind of “first time”.

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? One trusted (bi female) friend screwed up her courage and started a conversation with me about physical and emotional health, with regard to my anonymous hookups. We hadn’t talked about such things before, but the conversation helped me feel more empowered to make multi-dimensional decisions about sexuality and relationships.

What do you think about the Casual Sex Project? Casual sex needs to be further demystified, so I’m in favor of CSP.

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