Key West

As we walked into the club I was a little bit apprehensive. Here we were in Key West, which appeared to me to be the gay capitol of the world, going to see a show where all the performers were transvestites or . . . well I didn’t know what else but the thought made me a little uneasy. My wife was clearly happy to be there – it was something she had wanted to do for years. Once in San Francisco she had tried to talk me into going to a similar show but I had flatly refused. Over the years I found that my views had mellowed, and to be truthful I was more than a little curious about what we were going to see.

The club was already crowded although the show wouldn’t start for nearly an hour. The host escorted us to an empty table in the back, but of course Sandy protested. She wanted to be closer to the stage, and when he looked the host told us we would have to sit with another couple. She agreed quickly and while I was not keen on it, I thought it might be a good distraction for me to interact with another guy while our wives watched the show. I couldn’t believe it when our host stopped at a table near the stage where two men were sitting. They were obviously a couple and I immediately felt uncomfortable. Sandy had no qualms at all of course, and when I surveyed the surrounding tables I saw that these were the only two seats left near the stage so we sat down.

Introductions were made and I tried my best to be cordial, even friendly but I’m sure my nervousness came glaring through. Our table-mates seemed comfortable enough as my wife chatted easily with them. We ordered drinks and as we engaged in small talk I was glad that neither of these guys were the feminine type.

After the drinks arrived I quickly drank about half of mine and started to relax a bit. Jack and Arthur were transplants from Philadelphia, which gave Sandy a good start on conversation since her family was from Philly. I tried to chime in wherever I could but as usual she carried most of the conversation. Jack was in his mid-forties, with close cropped hair that was graying slightly at the temples and a dark complexion that hinted of a southern European lineage, perhaps Greek or Italian. Arthur was younger, perhaps late thirties with fair skin and brown hair that was probably blonde when he was younger. Both guys were good looking, a fact that didn’t escape my lovely wife.

By the time the second round of drinks arrived I was started to feel better. Jack must have sensed my earlier nervousness because he seemed to make more effort to chat with me about “guy stuff” – work, sports, etc. Indeed I was feeling comfortable; he seemed like a pretty regular guy. He was obviously well educated and informed and was very easy to talk to. Sandy was engaged in conversation with Arthur and for me it seemed that a bump in my evening had been smoothed out.

The show started and we all turned to watch. I have to admit it was better than I ever thought possible. Most of the performers were quite talented and I found my self thinking that more than a few of them were very attractive. I couldn’t believe that these were guys up there – they looked so much like women. I even found myself being aroused by one who performed a very sexy routine.

Whoa Lance, I said to myself. That’s a guy! Under that dress is a dick just like yours so stop thinking like that! But I couldn’t help it she/he was very sexy! At one point I looked away and saw that Sandy was watching me. She flashed be an impish grin, with a look that said “I told you you’d like it”. Damn, I thought, she’s always right about these things.

The guys seemed to be enjoying the show and the combination of alcohol and sexual innuendo was definitely getting everyone loose, including me. When the show was over I expected we would leave but Jack suggested we have another round of drinks so we sat and talked some more. Of course we talked about the show and the performers, comparing notes about the talented ones, and which ones we found attractive. By this time I didn’t really care anymore and was freely expressing my opinion about the particular artist that made me tingle a bit. Jack and Arthur got a good laugh out of it and my wife smiled at me slyly.

The performers came out from backstage still in their costumes and began circulating amongst the tables. I must have still been emitting some look of discomfort because the sexy one came right over to me, and put her (I mean his) arm around my shoulders. It was embarrassing of course but to be honest I was having a hard time remembering that this was a guy. His skin was soft, his motions so feminine that he certainly fooled my little head – my cock was starting to stiffen in my shorts. “Hello Sweetie” he/she said in a voice that was a little deep for a woman but still not really masculine. I felt her face close to mine as she spoke and my entire body stiffened, almost in a fight or flight response. “Relax, I’m not going to bite you – not yet anyway, I don’t know you that well.” My obvious discomfort made Jack, Arthur and especially Sandy laugh heartily. The performer picked up on it and reached her hand under the table and stroked my thigh. “Ooh you’re so tense”, she said,” maybe you need a massage.”

I felt her hand (his hand) shift on my leg and her fingers run up the inside of my thigh. When they reached the growing bulge in my shorts she cooed, “Hmmmm I think someone is VERY happy to see me.” I turned red with embarrassment and she drifted away to another table, leaving my companions in tears of laughter at my expense.

We finished our drinks, with the others still ribbing me about what had just happened and enjoying my obvious discomfort. We all rose to leave about the same moment, and Jack said “We know a little place down the street that serves fabulous desserts – would you like to join us?”. I was feeling pretty comfortable and nicely buzzed but I still surprised myself when I blurted out “Sure!” Sandy looked at me with a bit of surprise and perhaps puzzlement but she was definitely enjoying herself so she had no objection.

The walk to restaurant was a bit longer than I expected. My wife walked with Arthur, the two of them chatting like old friends while Jack and I followed along. He was really quite charming, and his stories about various places on the island set me completely at ease. We arrived at the place and were greeted warmly by the hostess – obviously they came here often – and she seated us at a table in a quiet corner. The review of the menu took some time but we finally settled on a pair of desserts to share and then examined the drink menu.

I knew exactly what I wanted: espresso and black Sambuca, my favorite late night indulgences. Arthur proclaimed his love of the black ‘Buca too, and we decided to order a round for he table. The waitress returned with the bad news that they had only white Sambuca. Seeing my disappointment Arthur volunteered that they had a bottle at their place and would love to have us come over after dessert. So we ordered coffee and espresso drinks to go with dessert and enjoyed them as a group. I was amazed at how much fun I was having being out with my wife and a gay couple but to be honest I had stopped thinking of them as “gay” and was now just thinking of them as a couple.

We finished dessert and exited the restaurant, and followed Arthur as he led the way to their condo. It wasn’t very far, perhaps a half dozen blocks located in a beautiful part of town. The surrounding homes were all beautifully restored and maintained and it was obvious that we were in a very affluent section. As we entered Sandy literally gasped “Oh what a beautiful home! You’ve done such a wonderful job of decorating!” This was obviously Arthur’s domain as he smiled proudly and asked “Would you like the grand tour?” My wife loves touring other people’s homes so off they went with Arthur describing all the work they had done to the place and Sandy gushing about the curtains and such.

Jack suggested to me that we get the drinks so I followed him to the dining room where there was a small bar.