What’s your gender? Man
How old are you? 55
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Professional
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? Like gay sex best, but straight when it comes to relationships
How many sexual partners have you had in your life (including oral sex)? 60?
How many hookup stories have you here posted before? 2

Three Guy Surprise, Two Submissive, One Dom

How long ago did this hookup happen? Three days ago

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

How would you best classify this hookup? Group sex

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? I had hooked up with one of them, Ed, about 3 or 4 times before. I first connected with him on Craigslist. The other guy I had not met until I entered Ed’s house, where the other guy was being fucked.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Well, Ed and I had hooked up before. Ed is Asian and a total, aggressive top. When I have gay sex, I’m a total bottom. We had arranged for me to come over to his house at 9:00 AM last Friday. When we correspond about sex, Ed always likes to talk to me in a very dominant, aggressive way. I’m not usually submissive, but with Ed, I enjoy totally submitting. That morning he told me to come over and asked me if my boy pussy was dripping in anticipation. That’s the sort of thing he says.

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? Ed’s house is about 20 minutes away, and while I was driving over I got two emails from Ed on my iPhone. The first one said I should just let myself in and come up to his bedroom. Since we’d fucked several times before, I knew my way around his house.

The second email was two sentences long. It said “Sophia is here. We may get started without you.”

I had no idea who he was talking about, but it certainly peaked my curiosity! When I got to Ed’s house, I let myself in the front door and went up the stairs to his room. There on the floor, on his hands and knees, was a guy dressed in a thong, bra, and frilly silk slip. Ed was fucking him, doggy style when I entered the room behind him. Ed stopped and said, “Sophia, this is Kevin. Kevin, this is Sophia.” Sophia just whimpered a bit. (I found out later that Sophia is married to a woman, but has for years been undergoing “training” by Ed to dress and act like a woman.)

OK, well I could see this was going to be more kinky than my usual encounter with Ed. Sure enough, Ed pointed at the bed and told me to change into those, pointing to a pink thong, fishnet stockings, and a frilly pink teddy. So I did, though it took me a while to figure out how to get things on right. Ed laughed at me and told me I was putting things on backward. He said he was naming me Karen. When I finally got everything on, Ed asked Sophia what she thought. “She’s pretty,” she said, looking me over.

Well, Ed and Sophia turned their attention back to sex, only now Sophia was sucking Ed’s cock. Ed asked Sophia whether she was willing to share his cock with Karen. Sophia whispered yes, and moved over to let me get closer. I got on my hands and knees and started sucking Ed’s cock, which was still wet from Sophia’s mouth. Ed said we should suck it together, one on each side, so we did. Sophia ran her mouth up and down one side of Ed’s cock, while I ran my mouth up and down the other. Every once in a while, Sophia’s lips would touch mine, and then, at one point, we both ran off the end of Ed’s cock at the same time and were kissing one another.

This was my first three-way, and you can imagine how excited I was getting. At that point, Ed asked me whether I would like to fuck Sophia. Well, as I said, I’m a bottom, and I haven’t had much success fucking other guys in the past. But I said I’d try. Before I could, though, Ed took over and started fucking Sophia again. Then he suddenly stopped and commanded me to lick Sophia’s asshole. So I spread her cheeks and started licking her ass. The more I did it, the more excited I got, and pretty soon I was sticking my tongue as far in as I could. Ed asked me if I could taste his cock in her ass, and I said yes, I could. (Though I really couldn’t tell the taste of his cock from the taste of Sophia’s clean, thoroughly fucked ass.)

Sophia moaned and whimpered while I licked her asshole. Then I stopped and asked if I could suck Sophia’s cock. Sophia said “If Ed says it’s ok.” Ed consented, and then Sophia turned around and let me fish her cock out from the front of her thong. Her cock was even nicer than Ed’s. It was thick and hard, and I started sucking it with gusto. Now, I’m a good cock sucker, but Sophia never came, because she said she felt strange having both Ed and me watching. So then we changed places and Sophia started sucking my cock. I don’t usually let people suck my cock — I like to suck theirs — but this was such a novel situation that I just submitted. Ed once again started to fuck Sophia, and after a while, both he and I were on the verge of cumming. I told Sophia, and she moaned in pleasure. A few seconds later, both Ed and I came at about the same time, Ed in Sophia’s ass, and me in her mouth.

That was the climax of the kinkiest sex I’ve ever had. Wow. There were so many “first times” in this encounter. First 3-way. First cross-dressing. First rimming. First total submission to a dominant male. First cock sucking followed by kissing another guy.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? Well, Sophia cleaned up and I jumped into the shower. By the time I was done, Sophia was gone. I said goodbye to Ed and headed off to my first meeting of the day. Talk about weird.

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, Learning new things, experimenting, Submission / Relinquishing power

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? Are you kidding? 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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? It was so kinky.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Well, I have to say that the cross-dressing was fun.

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

All things considered, how NEGATIVE was this experience? Not at all negative

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