A Night with the Boys

 

Image from the 
Jessie Hart Archives

Way back in the early days of going to what were known then as "transvestite" mixers, I ended up having a very special experience, In essence, I was still out with the boys, without my wife, it was just they were all dressed as women. 

The evening started innocently enough, with the usual sizing up of those cross dressers around us. A little bit of everyone was there from those cross dressers who were desperately trying to hold on to their masculine selves, all the way to the glamorous "A" listers who formed their own cliques. What I didn't know was during the evening, the group organizers were providing a few makeovers from professional makeup artists. 

I was intrigued by thinking I could be chosen for a makeover if I could fight through my fear to do it. Somehow I managed to land a makeover spot and then had to remove all the makeup I had spent so long to apply. Plus my ego thought I looked pretty good. I was to find out I was wrong.

There were several artists working, of both genders. It turned I was lucky and got one of the guys who were working diligently trying to do the impossible. In my case, he did do the impossible and I went through a magical transformation. To make matters better (or worse), along the way the make up guy was trying to explain all the techniques he was using to transform my face. I did my best to remember everything he told me and in the end run, he helped me to understand things such as the power of using a small amount of blush to highlight certain areas of my face. 

All too soon he finished his work and told me to put my wig back on. I could not believe the transformation and in my mind I was so excited  to show off my new look to the rest of the group. I did receive several compliments which cemented my desire to do more when the "A" listers went out on their own after the mixer was over. They normally went to some sort of a gay or lesbian venue to continue the party. To be able to go, I needed to be invited, so I began to seek out the one of the small group I knew and essentially invited myself along. I succeeded and managed to tag along for a night with the boys, all cross dressed as very attractive women. 

On this night, I was able to continue my own "Cinderella" experience when the group decided to call a taxi cab and go to an even smaller venue which to me looked as if it was a neighborhood tavern of some sort. It was somewhere in Cleveland, Ohio, which is all I remember now. This all happened during the pre-video game era and the place had two pinball machines. After I ordered a drink, I was able to find a couple quarters in my purse and started to play one of the games. Before long, a man approximately my age came up and wanted to play the same game with me so I had a decision to make. 

The rest of the group was wanting to leave and if I stayed, I would have to either call another cab or somehow depend upon this guy I had just met to get me back to the hotel. I made the split second decision to take the safe way out and leave with the "A" listers I came with. Before I did, to rub it in,  I made sure they knew I was approached by a guy and they weren't. 

From then on, I was more or less accepted by the group although I never had their privileged negative attitude which was so judgmental to others. However, from then on I was always searching for another "Cinderella" moment when I was able to spend a night with the boys without my wife. Partly because she normally always came along.

 Sadly, it never came again.