"Might-Have-Been" Threesomes
On a business trip to Puerto Rico I was sitting in a gay bar one late afternoon. The bar had pretenses of being "piss elegant," or was at least trying to get that way. Business was slow, and I was surprised to see a good looking young man sit at the bar and begin to strum a guitar and sing. Management had decided to provide some entertainment for the cocktail hour. I suspect this guy had shown up and offered to work for a nominal fee or even for tips. He was accompanied by a younger cute male friend. Accompanied in the sense of his being there, not that he provided any musical help.
So anyway the singer began to introduce himself to those sitting on the stools nearby, and was shaking hands, asking for song requests, joking around, etc. He shook my hand and asked my name, which he promptly forgot, since he asked it again about twenty minutes later after his set was finished. At that point he was sipping a drink and telling me about how he and his buddy had just arrived in Puerto Rico and were hoping to support themselves with his musical talent. He had made the rounds to several hotels, bars and clubs, but so far had been successful in getting work only at this small bar.
His friend was a very cute, babyfaced guy of maybe nineteen or twenty with a heavy southern drawl. He came from a small town in the rural south and was aghast at metropolitan San Juan. He loved it all. Both were very friendly but I was getting hungry and excused myself and left the bar.
Several hours later I found myself at a casino in a hotel along the Condado Strip. Losing money, of course. Looking up, who do I see but my new acquaintances, the singer and his friend. They try to bring me luck but to no avail and we repair to the bar. They hang out until I offer to pay for a drink with "my winnings" which they quickly accept. I assumed that these two guys were a couple. They had made some gay jokes earlier at the bar. For example after the singer completed a number his buddy applauded loudly. The singer said to the crowd, "That's my friend, I like to bring him along to clap. Actually I brought him to Puerto Rico because he doesn't have the clap." People laughed and everybody assumed that they were at least fuck buddies if not lovers. But now, later drinking in the casino bar, I wasn't absolutely certain that they were a couple or even gay since the younger one kept talking about how he missed his girlfriend. As he drank more, he missed her more and more and regretted the argument they had had before he left town.
"She gimme a nahs blowjob bafoe ah lef. Po gal had no eye-dear tha she warnt gonna see me agin."
His buddy, the singer, did not like the direction of the conversation at all. He had been coming on to me and was touching my arm and thigh from time to time.
"Hey, hey, hey" the singer said. "No more of these sad stories. Let's have some fun here." And turning toward me: "What hotel are you staying at?"
I mentioned one on the Strip.
The singer whistled. "Hey that one is real expensive. I guess your company pays for it, huh? Well, you know Virgil and I here need a place to crash tonight."
I took another look at the singer. Prime stuff. About twenty four or twenty five years old, thin, wiry build, with a long handsome face, perennial smile with a prominent jaw and a wispy light brown mustache. The younger guy had a round cute face with chubby cheeks, short light brown hair, slight, compact body. Tempting, very tempting.
I decided not to pick up on the offer for company, (big surprise, right?) and excused myself shortly afterward. As I walked back to the hotel, I fantasized about rolling around my big bed with these two cuties. A couple of days later I saw them on the street hanging out near the gay beach. They were beginning to look tired. The younger kid's t shirt was dirty and the older guy had a spaced out look that might have meant drugs or maybe just that he hadn't slept in a long time. But although I probably made the right decision in walking away from those two, I did think about them several times afterward. And wondered. What might have been.
Another threesome opportunity that I turned down and don't really regret, happened in New York. I was at a small gay bathhouse in lower Manhattan one afternoon. It was slow and I began to fool around with a man about my own age, who also wore a wedding band. When I left the sauna to cool off, he followed me outside, and sat next to me on a bench. He started up with me again and then suggested that I go home with him to fuck his wife.
"Fuck your wife? Are you serious? What would she think of you suggesting that?"
"Oh, she would love it. She would really get turned on by you. I know she would. We've done this sort of thing before."
"You bring guys home to fuck your wife? Do you have sex with her?"
"Well, yeah, we have sex. But it's much more exciting for both of us when I bring somebody home. I mean, I screen them very carefully. I don't bring home any old scuzzy guy. You would have a great time. We live in Staten Island. My car is nearby, I'd drive you there and back."
"You know, this sounds exciting. And I'm really flattered that you want me in on your scene. But I'd never do anything like that. I mean I do fool around with men, of course. But I feel that that's really okay, because I've come to accept the fact that I'm gay or bisexual or whatever. And I need male sex, and I'm entitled to express that part of me. But it feels like having sex with women would be cheating on my wife."
"Yeah, I understand. You're not the first guy that has said that kind of thing to me. That's cool. I have an understanding with my wife, and we are in agreement that it spices up our sex life for me to bring home another man once in a while. But I completely understand if you're not okay with that. If you change your mind, I'll be up in the video room."
And so ended the second Might-Have-Been Threesome. Years later, I saw an ad in the personals for a threesome with a woman and a guy, and I thought back on the sauna offer that I let pass. It was tempting at the time, but again I think that I did the right thing for me.
The third missed threesome opportunity that I'm remembering today happened in Washington DC. An older married guy from Chicago, Roy, tried to set up a threesome with me and another guy. What happened is that I had run into this guy Roy two or three times on earlier business trips. We were both in DC for work meetings fairly often, and had met at a hotel bar. So we knew each other fairly well.
This evening, as we stood near the bar, nursing a drink and bullshitting, Roy started to tell me what he would like for me to do for him up in his room.
"You know what I'd do is to lie you down on the bed with your head hanging over the side and then I'd stand next to the bed and just slowly, slowly, feed you my cock. Gently I would slip it into your mouth and down your throat. Fucking your face upside down. Really turns me on to think of it."
"Oh, yeah. Forget it. I don't like the sound of it. How about me? How do I get off?"
"Don't worry. Don't worry. I'd treat you right. I'd make sure you got your nuts off."
As Roy and I continued to banter in this way, it became apparent that a third guy was listening to our conversation.
"Sounds hot to me," he interjected at one point.
Roy picked up on his interest immediately and drew him into our conversation. He was a younger guy. Slender, brown hair, pleasant face, about 35 years old. He was wearing a suit. He seemed to like Roy's take-charge manner very much. The two of them began talking among themselves as I went for a drink refill. Several minutes later, Roy approached me and said that he had arranged a threesome with the young guy in the suit. I looked over at the third guy. He was looking over at us and smiling. Talk about temptation! I hesitantly agreed. Roy told me his room number. He would go up first and then the other guy and I were to go separately to the elevators and meet up in Roy's room. OK, so what happened? Well, you know. Tony chickened out on the way to the elevator.
The following evening I met Roy in the same bar.
"Hey what happened to you last night?"
"Oh, man, you know me. I'm always hesitant to take chances with strangers."
"Too bad, too bad. That dude was fantastic." Roy followed with a salacious account of their encounter. "He was real disappointed you didn't show. He kept saying: 'Where's the other guy? Is the little guy coming? I thought you said it would be the three of us.' You nearly ruined things for me, man."
And so I again tasted the bitter taste of missed opportunities. But planted in the back of my mind was the idea, that somehow, someday I would take part in a threesome.