An Opportunity or Challenge

Image from Dylan McLeod 
on UnSplash

If you are similar to me and if you had a quarter for every time you heard a so called problem was no more than an opportunity to improve, you would be wealthy.

As I moved forward down my gender path, I found an increasing number of opportunities. As I mention often (or all the time), I had a difficult time adjusting to how I should try to present myself as a novice cross dresser. All outfits which included too short mini skirts or shorts were out. In place came a more conservative wardrobe which I found I could blend in with the other women I encountered. The challenge or opportunities I encountered were exciting yet terrifying. 

I had many firsts to deal with in my wide wonderful new feminine world. Many of the firsts I encountered, did not go smoothly and I went home sobbing. When I did, in the safety of my own home, I took ownership of the damages and attempted to build a plan to do better in the future. I went through every opportunity to improve such as better makeup, wigs and wardrobe as examples. I was very focused on the entire process. To the point, I had a difficult time when I still had to function as my old male self. I experienced a new challenge to stay in cross dressed mode when I flipped my gender script. Slowly but surely I was spending more physical time as my feminine self. It took me years to realize I was a woman cross dressing as a man. Not the opposite. 

Then, when I really started to seriously cross the gender frontier and deal one on one with the public, other opportunities or challenges became important. By this time, I was becoming very courageous in how I lived my life. I sought new venues to see if I would be challenged as a transgender woman. Some worked out and some didn't, so I crossed many off of the list. Many of the opportunities became challenges back in those days when I first began to seek access to women's restrooms. The whole process was an overall success with some notable failures when I had the police called on me. Still I persisted and earned my rest room privileges the hard way by learning the etiquette involved with using the women's room. Such as always looking other women in the eye, not putting my purse on the floor and pausing to wash my hands (no matter how much attention I was creating) among so many other nuances I was learning. To go into it all would entail a whole different blog post.

Another huge challenge or opportunity I faced was when I decided to begin gender affirming hormones, formerly HRT. There was no way I could anticipate the changes by body would go through. Both externally and internally as I was suddenly seeing the world in a softer version of it's former self. My sense of smell heightened and my thermostat changed as I became colder easier are just two examples. All in all, my body took to the changes easily and I felt as if I should made the change years before I did.

If I had utilized all the time and energy I needed to overcome the challenges of changing my gender and put the energy into my male self, how much farther could he have gone. The end result was so powerful, there was no way I could ever look back and change my reaction to anything.  

The Ultimate Obsession

 

Image from Brett Jordan
on UnSplash

As I recall, the ultimate obsession I had with being feminine began with explorations into my Mom's clothing and makeup. Once I started I couldn't let it go.

Little did I know, I would need to follow quite the winding and rough path as I crossed the gender border from male to female. As soon as I conquered one of my goals and escaped my very dark and lonely closet another wall or barrier would crop up to challenge my obsession. An example would be how I imagined just improving my outward feminine appearance would be enough to help me live in the world as a transgender woman. All the process really did was set me up for other huge challenges.

Challenges such as how I would or ever could learn to communicate with other women in their world. Nothing in the process was easy and often terrifying. The old "no pain-no gain" saying proved to be all too true. Just attempting to modulate a feminine sounding voice to match my appearance was the ultimate challenge. Plus I needed to learn to always make eye contact with other women as we engaged in conversation. A simple statement saying I loved another woman's ear-rings often proved to be the ice breaker I needed to survive in my new gender world. 

Through it all, my male self was fighting me all the way. Every move I made to try to enable me to be more feminine was a problem to him. Deep down he knew he was fighting a losing battle because when I was pursuing my authentic self I felt so natural. So everytime I was questioning the path I was taking, the bottom line was if it all felt so natural, it was the right thing to do. Somehow I needed to conquer my fears and temporary setbacks and follow my own personal ultimate obsession. Follow it I did.

No matter how complex my life became as I ended up attempting to share a life between the two primary genders, until the pressure became too intense to survive, I did my best to live my life. My male self kept resorting back to what he had always done...internalize his feelings and hope for the best. His best never came as I continued my path towards my ultimate obsession. Even then, I had no idea if I could make it to my ultimate goal of living a life as a transgender woman. Fulltime with no interference from my old male self. 

As I always point out the struggle nearly killed me and I would not wish it on my worst enemy. I was one of the lucky trans women or trans men who all of a sudden found the doors opening which would allow me to finally follow my obsession which had followed me my entire life.  Destiny showed me the way around life's setbacks such as close friends and family dying. It all allowed me to have very little resistance to living my own life as I saw fit. Also near the same time, the Veterans health care system I was part of started to provide help with hormone replacement therapy, which I was fortunate enough to be healthy enough to be a part of.

In short, my life which was very much in shambles faded away and I was finally able to achieve my ultimate obsession. To lead a feminine life and even to become remarried again to my wife Liz who accepted me all the way. 

The path I took was never easy but on the other hand, my trip was never boring and provided me with a unique look at life others never have.  

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.

How New Was It?

Photo from Civil War Cemetery. The
Jessie Hart Collection

 During my transgender journey, I considered each hill I climbed and every blind curve I conquered as being a new part of my life.

Looking back at it now, I wonder how new it really was. Through it all, as I learned from all the ups and downs of transitioning I was just being me. The sad part was how long it took me to arrive at the point of my life when I could put my old male self behind me and move on. It was at once so exciting yet terrifying to put all my male privileges away and explore what a feminine life had to offer.

The more I explored the world, the more I learned much of it wasn't new at all. If you are a believer in reincarnation somehow I felt I had been there before. In other words, my transition to a transgender woman felt so natural. I felt as if I should have always been living this way.  Even though I felt more and more natural, my old unwanted male self still stubbornly hung on thinking he could make a come back and reclaim my life. I even tried to live between the two main binary genders until the stress became to much to bear and I needed to make a decision. Finally I made the right decision to begin hormone replacement therapy and try to adopt a fulltime life as a transgender woman, without any of the major surgeries some trans women undergo. I just didn't feel the need to subject my body to any major gender surgeries seeing as how I was reaching my mid sixties by that time in my life. I considered myself fortunate in that my body was in good enough condition to accept the rigors of the changes I went through. 

Since my main premise through the years was gender was between the ears and sex was between the legs, I opted for more work between the ears. The final straw which broke the camels' back in my transition was when I met my wife Liz going on twelve years ago. Before I met her, I thought the chances of having anyone accept the new me would be nearly impossible. I couldn't believe it when  one day, Liz told me why didn't I just go all the way in my MtF gender transition because she didn't see any male in me at all. At that point I knew somehow I could make it another relationship with another person. Let alone another woman. The concept was very new because my previous two wives accepted the fact I was a transvestite but never adjusted to any of the concept I could be transgender. The unexpected turned into reality. 

From then on, the adjustment was immense as Liz and I needed to learn to live together as I was adjusting to living in a totally new gender. Ironically the easiest part probably was the gender adjustment I needed to make. When my feminine self was finally freed up to live out of the closet, she took to it completely and without reservations. She proved I should have been listening to her all along.  As far as my male self went, he quickly faded into the background and was rarely missed except for situations when I found myself in highly testosterone laden places such as auto shops. In those places, I learned quickly what "man-splaining" was really all about. 

It turned out, completing my gender transition wasn't new at all. I had been working my whole life to do it.

No Cure for the Transgender Person

 Most of us learn the hard way there is no easy cure for our gender issues. Marriage, kids and the military are a few of the most common so called "cures" Of course we all found out adding the responsibilities of a spouse and/or family just complicated our lives. Here is a comment I received from Sara:

Photo Source
Sara

" I wish I had known more back before the pre internet days! Like getting married WOULD NOT CURE ME! I wouldn't have put the wife and kids through all tis mess, mine comes from the fact that my mom was given something to stop the many miscarriages she had, or something went wrong/right and here I am today, or was it something else?" 

Thanks Sara! I felt the same way even though my two wives knew of my cross dressing desires. The difference was though no one, including me understood my feminine desires went far beyond the occasional desire to put on a dress. 

Sara also refers to the DES drug which was given to Mother's with history of problem pregnancies. Although I can't prove it, I believe my Mother took the medication which flooded the uterus with extra estrogen.  

As far as the military went, I would have never served except when I was drafted into the Army. I just didn't understand how I would ever adjust to being away from my feminine self for three long years. Adjust I did though and was rewarded more than I could ever say. I can't write enough how my daughters support helped me over the years. 

Over the years also, along with the advent of the "information" age, an amazing amount of information is available to help spouses who need it with extra help dealing with a difficult gender transition. This week I encountered both sides of spouses who accepted (or not) their spouses desire to cross the gender border. The first I experienced came on a very sad post from Kira on how she was giving up after ten years of rejection from her spouse. Sadly she was going back to her male life. Mainly after her wife's threats to "out" her to her work and friends. 

On the other side though came a very nice/inspirational comment from Anne: "I am going to share your courageous story with my husband. He/she has been cross dressing since age 12. Looking and feeling feminine was very important but always controversial when parents or siblings discovered cross dressing activities. During Covid my husband has finally felt safe enough to dress as a female at home and occasionally in public away from our community.

He also started over the counter feminizing supplements and herbs last year with some positive results. He is undergoing M2F counseling before formally beginning the HRT protocols.

Your writings are very helpful for both of us as my husband proceeds further."

Thanks to you Anne! I already responded praising her positive response. It is so sad many transgender individuals never have had a chance to take advantage of such a positive outlook from a spouse. Anne also brought up a good point when she pointed out her spouse was seeking professional counseling before undergoing HRT. It's very important to do so!

A transition is never easy and the only cure for crossing the gender border is realizing you have no real choice. For whatever reason. Just accepting your desires and yourself is a giant part of the solution. As I think back to when I finally decided to start hormone replacement therapy (HRT) and begin my femininizing process, I felt a huge weight off my shoulders.

I was on the way to my cure.  

Sports and the "Big T."

 As football season winds down, for the first time in over three decades the Cincinnati Bengals are playing the Kansas City Chiefs for a chance to play in the Super Bowl. Kansas City is a tough talented team so they will be difficult to defeat

None of that hurts my enthusiasm. In my long life of 70 plus years, I have witnessed only two visits to the Super Bowl by the Bengals and both were heartbreaking defeats. On one occasion I even suffered a broken bone in my foot trying an ill advised leap during a touchdown run. I have written before how I had to make up a weak excuse for my boss why I worked the next several days on crutches.    

During todays' game you can bet I won't being trying any leaps. In fact with my testosterone levels so low and my estrogen so high, I'm definitely aren't so passionate anymore. I used to be so competitive I had a difficult time playing any sort of a game because I hated to lose. On the other hand, I am a better fan. I watch the games with more nuance. Maybe why there are so many more women these days who are sports fans.  

On another topic away from football, I received several great comments on my post "What's in a Name". The first is from Lisa :

"I completely understand. I went through several names before settling on Lisa, but it is a diminutive for Elizabeth, which is what I plan to use on my birth certificate, if I ever change it. I too have the grandkid issue, and have thought of putting my current first two initials as my middle name so they can use that. Not too different from your solution. "Great minds think alike!"

Thanks Lisa! And, another from Paula:

"It is a revelation to many that anyone can change their name, like you I went through a lot of names, more or less exotic. But when I realised that this was for keeps I went for the pragmatic answer, and the one that meant I didn't have to change my signature!

We grow up with the name our parents gave us and it becomes a part of our identity, so when we choose a new name we have to make sure it is one we are going to be happy taking as part of our identity. A while back my name was printed in a concert program as "Pauline" I was horrified as I though "No, I could never be a Pauline!"

As always thanks Paula! 

Finally GO BENGALS!!!!!