It's all In the Preparation

 

Anniversary Selfie from the
Jessie Hart Archives

Anyway you slice it, crossing the gender border to your authentic self is a huge task which takes a ton of work.

First of all you have to attempt to solve the problem of securing and applying makeup and clothes.  When I started I couldn't even paint my model cars well let alone my face. More times than not I ended up looking like a clown. It took me so long to be able to take my own meager funds and then sneak out to a store to buy my own cosmetics. The whole process was one of the scariest moments of my young life. To this day, I don't know how I pulled it off with my Dad working just  a block down the street. But I did and managed to learn the preparation needed to much later on leave my closet and join the world as a transgender woman. Of course with my wardrobe, again the same was true. I needed to mix and match whatever clothing items I could to do the best I could until I could afford to do better.

Perhaps two of the most beneficial things I did to further my transition was to take care of my skin and lose weight. Little did I realize, when I completed my daily hated shaving, I was actually helping my outward appearance, including when I applied a moisturizer when I did it. I am a believer it all helped when I began my hormone replacement therapy and my skin started to naturally soften anyhow. It was similar to going through puberty again. Just reversed from when I did I as a male growing up. The harsh, hated angles I acquired started to soften which made it so much easier for me to present to the world as a transgender woman.

The other main thing I did to further my male to female gender transition was to lose weight. In fact, I was able to lose nearly fifty pounds when I began to seriously attempt to the public's eye and begin to seriously go out. Of course it made finding and wearing fashionable clothes easer to find. It turned out, it was all in the preparation as I shopped for just the right accessory to go with just the right outfit. Fairly quickly, I faced the problem of over dressing the other women around me and needed to be careful if I wanted to blend in and not cause too much attention to me. Because, even with losing the weight, I still was a fairly large bodied woman and needed to do my best to present around the fact I had been subjected to testosterone poisoning in my past. 

Through it all, I learned again what I already knew. Being a woman meant joining the high maintenance gender and everything I thought I knew about being feminine had to be re-learned. A fact my second wife tried to tell me when what was left of my stubborn male ego wouldn't listen to her. When she told me I made a terrible woman, she wasn't talking about my appearance. Which turned out to be very difficult in one sense yet was the easiest  part of my transition in another. 

Often I wonder what it would have been like if I had had the opportunity to grow up as my chosen gender. To have had the peer pressure to look and act a certain way. More than likely, the grass would not have been as green as I think it would have been. Mainly because I think my Mom would have put increased pressure on me to conform to her world. Whatever the case, I think preparation would have been the key. Having more of it at an early age would have certainly helped.

The Final Payment Became Due

Image from Blake Wisz 
On UnSplash

For fifty plus years I put off the inevitable, I was born to be a woman. 

I put it off for years by making partial payments to allow my male self to exist. Slowly but surely my gender currency ran out and I needed to make a change before the process killed me. As I made payments, I needed to decide (or try to) just exactly what it was I paying for. Similar to so many, I spent years believing I was engaged in a harmless past-time of just wanting to look like a girl. All along, deep down, I knew the process wasn't working because the problem was never solved. I would dress in front of the mirror and for a couple of days following, I would be satisfied with myself but then the satisfaction began to fade and life became hell for me again and again. My natural response was to keep making payments to put off the truth of my gender aspirations.

After awhile, even I learned how to better my appearance so I could escape my dark lonely gender closet and explore the world. In many ways, during this time, I considered myself a very serious cross dresser or transvestite. There was no way possible I was just innocently pursuing being a feminine person. I was going all out to get my money's worth by starting to interact with the public. In fact, I was beginning to feel as if I would be more comfortable labeling myself as transgender since I was making all the payments. 

It was about this time when I started to scrape together all of inner collateral I could find to take bigger and bigger chances in the world. I began to go to straight and lesbian bars and left the so called safe gay venues behind. By doing so, I met a whole new set of surprisingly accepting people I could associate with. In other words, I was getting my money's worth and I wanted more and more. To do so, I needed to become increasingly creative on how I spent my time. So, I began to do activities  such as Christmas shopping as well as doing a portion of the grocery shopping for the house. Any thing to experience more of the world as my authentic self. 

Through it all, I could finally see the end to all my gender payments. Several friends who I mention often helped me build confidence in myself. And sadly when my wife passed away, the main obstacle to transitioning into a full time transgender woman was put behind me. Even still, seeing the possibility of making the final payment was not an easy one to consider. I had worked too long to succeed in a male world for it to be cast aside easily. 

Finally, the powers to be said no more payments and with considerable help, I made the final gender leap of faith. Out went the old unwanted male clothes and I set out to take what I learned and make the most of the process. It was at once exciting as well as terrifying but I made it. All in all, the final payment was a relief when it was due.  

Day Dreamer

 

Recent PicNic. Liz on Right.

Throughout all the years of my life, I wish I could reclaim just a small portion of the time I lost day dreaming of my gender issues.

Of course I am referring to are the times when I zoned out of my reality into a world where I left my unwanted male world behind and live as a female. I vividly remember having a complete crush on the girls who sat around me during study halls in junior high as well as high school. I never had a sexual crush, I really wanted to be them. During the years which followed, my feelings towards women never really changed until I married and began to have a differing view of women after observing them close up. I found in many ways, women and men face similar challenges. Just on different stages. 

Through it all, I wanted to still be feminine and spent plenty of time thinking and worrying about the process. During the Vietnam War era, I was jealous of women since they couldn't be drafted into the military which was probably my peak of wanting to be a female. For awhile, during the rigors of going through Army Basic Training, I was able to briefly escape the even stronger stresses of living with gender problems. I say briefly,  because it wasn't very long until my old gender issues returned. In fact, one of my best day dreams was to reappear in front of my fiancé who ditched me just before I was to leave to join the military. In the worst way, I wanted to come back in a new car looking better than she did. Revenge would be sweet but it never came. You might say, as I grew into my authentic self, I moved past her altogether. 

It ended up requiring nearly a total male to female gender transition for me to mostly completely lose being a day dreamer. The more issues and even problems I encountered as a transgender woman taught me I didn't have to day dream about the transition process any longer. As I said, it is important to note not all the day dreams I felt turned out to be good. I ended up living through too many negative life experiences which for the most part revolved around my new appearance and where I tried to do in my new life. Perhaps one of the main lessons I learned was women were always on stage. Men admired them from one angle while other women did also for totally different reasons. It was quite the learning process and robbed me of any extra time I had to day dream.

Sadly, we only have one life to live and I can't go back and reclaim any of the time and energy I lost when I was a novice transgender woman. On the other hand, the experiences I gained from my life could not be traded for anything I could have ever expected. Now my day dream problem has been reversed so I don't live too much in the past.