All Hands on Deck

 

Image from UnSplash

As I progressed farther along my long and difficult gender journey, there were many times where I wished I had company to aid my path.

Even though I often whine and cry concerning the lack of assistance novice cross dressers or transgender women have early on in their progression, the fact remains we need to work our way through it and do the best we can with our fashion and makeup. Until I began to see positive results, I am sure I looked like a clown in drag. Still, I was alone with my thoughts. I am old enough to remember with "Virginia Prince" and her Transvestia publication first came to my attention. It provided me with the first real look at others who shared the same interest in being femininized and looking like a girl. I was mesmerized with more than a few of the cross dressers I saw in the publication. I so badly wanted to be like them.

For years as I worked alone to look more realistic as a cross dresser, I still yearned for feminine help. I thought any cis woman could help me because of their years of practice and interaction with their peers. When I was engaged in college, the opportunity to be dressed from head to toe as a woman by another woman finally came my way. Somehow, I begged my fiancé to do it even though I don't remember now how I did it or was so persuasive. I went all the way by even renting a motel room for all the pre-prep work such as shaving my body I would have to do. 

Once I shaved and dressed, I was excited to undergo the long-awaited makeup process. Since she wore quite a lot of makeup, I was confident she could do a great job. It was finally time for all hands-on deck in my young cross-dressing life. Back in those days, mini skirts and dresses were in vogue so I brought one I found and purchased along with panty hose, heels, and a long blond wig and started the transformation process. To say I was excited would be an understatement. Time flew by as she finished my makeup, and I headed for the mirror. Instead of the beautiful blond I thought I was going to see, I was actually disappointed. I could not see much difference in her efforts from my own. Even still, I acted as if I was really impressed with her expertise when in fact, I was impressed with how much I had learned on my own over the years. 

It took me a long time working with makeup to learn each of us has a blank face to work with and we need to learn the best way to work with it. My fiancé was doing the best she could with the knowledge she learned from her own face, not mine. She was far from being a professional such as the help I finally received from a true makeup pro at a transvestite, transgender mixer I attended years later after I was discharged from the Army. He taught me lessons about my face I had never even considered such as which features to play down and which ones to build up. To this day, I owe him a huge vote of confidence and thanks.

It turned out the opposite happened with my fiancé. Due to knowing my deepest, darkest secret about being a cross dresser, she said I should use it to dodge the draft and stay out of the Vietnam war. There was no way I was going to do that, so we split up shortly before I was to leave for basic training. Actually, it was the best thing which has ever happened to me in my life. The pain it caused immediately would have been nothing like the suffering we would have gone through if we had stayed together.  

Looking back, at my life's work as a transgender woman, for the most part, it has been a solitary experience. Not having a female peer group to interact with and learn from was a problem to be sure but one I learned to work around. The end result was, I needed to be better than the next woman to make it. 

I Never Felt so Alive

Image from JJ Hart

 
One of the main reasons I found my way into transgender womanhood was when I was exploring the lifestyle of a trans woman, I never felt so alive.

It all started when I resolved one night to change my basic mind set from just thinking I was a part time cross dresser all the way to considering changing my mind all-together to I was a woman pretending to be a man, and I was so tired of feeling that way. All of my new thoughts centering on my gender led me to what I came to consider as my second grand gender transition on the night I went out to a venue to blend in with all the other professional women who were getting off of work. The difference was I did not just want to blend in, I wanted to be them. Even though I was petrified of what I was attempting, I made it through and even was accepted by all I encountered. 

The bottom line was I never felt so alive in my life and knew my life had changed forever. The problem was, in those days, I had serious male baggage to deal with. Similar to many of you, I had a spouse, family and good job to think about even though dealing with them as a male was pulling me down. Regardless, I kept on fighting and learning more and more about the femininized life I was considering undertaking. I was naive and thought I had achieved my goal of learning everything I could about living as a woman when I was just starting my path. I put all those years of just thinking my life would be just one of appearance. As my wife kept trying to tell me, I had a long way to go to learn what the life of a woman was all about. She was right, and I resolved myself to find out what she meant. 

Primarily, what I learned was a woman's life was very layered and difficult to experience because finding women who were willing to allow me behind the gender curtain were difficult to find. I was left to learn it all by myself until I reached a certain level of transition. In other words, I needed to pay my gender dues until I earned my path to the girl's sandbox. Often the route was bumpy, rough, and unforgiving but I lived and learned. Even though (as I always mention) I found friends to help me, I needed to basically keep my mouth shut and observe how the world around me was going about their everyday lives behind the gender curtain as women. 

Through it all, I continued to feel more alive than I had ever felt before as a male. I can compare the process to being guided by a searchlight in a gender fog which was my gender dysphoria. Call it gender euphoria or whatever, I could not wait until I could take the next step towards a complete life as a transgender woman. 

Pain

Image from Tony Frost
on UnSplash

Looking back, I don't think I write enough about the pain I felt during my life which was closely related to my gender issues. 

First of all, I was living in a world where nothing was ever as it seemed. Life had wedged me into living a male pattern I never felt a part of, and I could not escape. One of the problems was I was privileged in so many ways and was told constantly about it. After all, I was white, middle classed male child and all I needed to do was find a way to fit in. The pain was considerable when I learned I just couldn't. I did not have a choice, all I really wanted to do was be a girl.

Much later in life, when information began to become more available, my problem began to be known as gender dysphoria. Having a term was good enough but did nothing to relieve my pain. The only cure was to cross dress in front of the mirror and try to imagine how it would be to be a girl. I was successful in blissfully thinking I was headed in the right direction, until I started to head out of my closet and explore the world. When I did, the public took the mirror's place, and I was judged (sometimes very harshly) by an unforgiving world. Unless you happen to be a natural as a transitioning male to female person, perhaps you have been in the same circumstance of having to learn to present well as a woman. At times, the entire journey I was on seemed to be a steep insurmountable path. 

Still, I learned from the days and nights of pain I endured and kept on trying to improve my feminine presentation. My tears finally subsided, and gender euphoria set in. Maybe I could achieve my dreams of transgender womanhood. What I did not realize was how far I still needed to go. No matter how far along I thought I was with my makeup, hair and fashion, there were still hurdles to jump with communication and interaction in the real world as a trans woman. Plus, there was the very painful life I was leading as two genders when I needed to hide what I was doing from my unaccepting second wife. I always considered myself a very honest person, so being dishonest with her about my truth caused me great sorrow and pain but at that point I could not turn back.

Before I knew it, she passed away and a new pain such I had never known set into my life. It seemed I learned again how death was forever, and loneliness would follow. What I did not realize was how life could go full circle if you are fortunate enough to live long enough as I was. Slowly but surely, the fleeting wisdom of age taught me life offered both joy and pain along the way. It just so happened in my life; gender played a very important part. 

Also, life taught me feeling gender dysphoria or pain helped me to appreciate gender euphoria or joy even more. Regardless, I need to point out my gender journey was never easy and required my utmost attention. So, I could survive all of my pain.