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. 

Role Model

 

Image from Averie Woodard
on UnSplash

I have a close acquaintance who is taking a giant step forward in her transgender world.

She is stepping out of her comfort zone and will apply for a new job as her authentic feminine self. I was fortunate to be at one of her first attempts to explain why she was coming out of the closet which was tormenting her so much. I remember thinking at the time how far she had to go on her journey as I wished her the best.

During the following years, she has faced the same issues as other transgender women and trans men face, from marriage issues to kids and family decisions to decide upon. She has been very open on social media about her struggles. Including public pushback when her wife and her go out to eat. She lives very close to me and I know the venues she has had problems in and I understand why. In fact, I have had some problems also in one of the venues and we never went back.

Even with all of that, she pushed on and is now trying to take her transgender life to another level. Her current job is a truck driver which of course presented it's own level of challenge at every stop she made. She transitioned on the job and literally changed  her outward appearance overnight. I really respect the courage it took for her to take on her work world the way she did. Now the challenge she is seeking is to apply for another job (in the same industry) but in a whole different job as her feminine self as a logistical scheduler of sorts. 

If she gets this job or not, she is a true role model for others in the transgender community. To step out of her old gender comfort zone and sever ties with her old life as a man is remarkable.  It's a giant step forward. 

I am far from an expert in finding a job in todays' world. But from what I am reading in Cincinnati alone there are a few companies who are LGBTQ+ inclusive and offer employment possibilities to aid in a person's transition. It's good for both parties as the company can hire a good employee and the trans person is able to take a giant leap forward and support themselves financially in their new world. 

As I circle back to the person I know who is applying for the new job, I am sure this is just the beginning one way or another for her to step forward into a life she has always dreamed of. I hope she gets the job on the first try! 

Even though I am retired and don't have to face the work world as a transgender woman, I can still see a role model when I know one. 

The Good Fight

Image from Fred Moon 
on UnSplash

Often, our biggest enemy we face when we transition from one binary gender to another is ourselves. 

In the case of male to female gender transitioners the male ego never wants to give up his control. In my case it was a fight to the bitter end. A fight which nearly killed me. As along the way my old male self seized upon every means possible to preserve his existence and furthermore, he never fought fair. He felt he carried all the cards and only played any when he was pressed to do so. 

Through it all, what he never counted on was the inherent strength of my inner feminine self. Along the way he was ego driven to the point where he thought dressing as a transgender woman was simply a hobby he had to relieve the stresses of the world. When in reality, the opposite was true. She was letting him continue to express his masculine self while she bided her time and waited for her chance to shine in the world. 

As I continued to explore the world as my feminine self, it became clear to me who the winner of my gender struggle would be. Every step of the way in my brave new world felt so natural. Before I knew it my so called even split living life the best I could as a male and a female became more and more female and when I was spending life as a male, all I did was dream of what my next step would be as a woman. Where would I go and what would I do?

Of course the biggest problem I faced was my male self held the power cards such as family, friends and finances. The most powerful card he held was the influence he had with my wife of twenty five years who I desperately loved. She wanted nothing to do with my female and created the ultimate catfight between two women. In the meantime, in protest to having less and less influence in my life, my male self made my existence miserable, ruined my mental health and led me to try a suicide one night. He was prepared to risk my entire life just to maintain his. In addition, he pushed me into more and more alcohol abusive situations. Happily, I was able to end his influence when I transitioned before I seriously damaged my body. 

None of any of that mattered to my male self as he fought the good fight and slowly but surely was sliding down a very slippery gender slope. Deep down he knew every successful moment my novice transgender self experienced, the fewer chances he would have to claim his existence.  In typical male fashion, he moved ahead fighting change at every turn without thinking of the final outcome. In the process, he was making himself and everyone around him miserable. 

Finally he knew enough was enough and with the help of a few very close cis-women friends I took the leap and transitioned into a new life as a transgender woman. The slope I mentioned abruptly ended and I went into a gender free fall. Little did I know at the time how strong my inner female was and how much she appreciated finally being free and having the chance to run my life. 

It turned out she really knew how to fight the good fight since she had been fighting her entire life to live an authentic life. There are days, I wish I would have intervened in my gender fight earlier in life but as it stands now I have to live with what I did.