The Ultimate Challenge

Vacation image from Kansas
by JJ Hart

I am biased but I think changing how you live to reflect your authentic gender self is one of the toughest things a human can do. 

Perhaps you noticed I said reflect your gender tastes not change them. I believe our transgender selves are already determined and we are attempting to sync them up to our extremal selves the world can see. The path varies for most of us but the final goal is always the same. Sadly we have many obstacles in our way. 

One of the main ones is trying to overcome the effects of testosterone poisoning which gives us the hated male characteristics we did not ask for. I remember hating all the changes which were happening to my body and how the changes would effect me when I attempted to cross dress in front of the mirror. All I knew was my life was changing for the worst and I did not want it. Much later on when I became much more serious about my femininized presentation in public, my goal was to hide my broad shoulders and the angles of my body with new fashion. 

It turned out, testosterone poisoning and new fashion were the least of my problems as I continued along my path to the ultimate challenge of living as a full time transgender woman. There were so many times I never thought I was going to make it. I had so much baggage to sort through as a man as I had acquired over the years. Since I had spent so long doing my best to build my life, then I needed to decide what to do about my family, job and friends. Leaving me between the gender rock and a hard place. Often I did not know how I was going to find my way out of my predicament. Was I still a man, or a woman and what about my long standing sexuality.

Obviously, the ultimate challenge was to sort through all my issues while I was still attempting to live my so called normal life as a man. I ended up trying to live a little at a time as a trans woman until it began to feel so natural I never wanted to go back. Slowly but surely I was proving to myself I had been born feminine and just forced into the wrong gender by some sort of a cruel twist of fate.

It was around that time, I found I was not alone and began to discover other challenges on my path to transgender success. I learned from others around me about their own successes and failures or triumphs and purges. Often my own feminine wardrobe would be gifted by an acquaintance's giant purge. In fact, my first set of expensive silicon breast forms were gifted to me. The breast forms were a real step forward from what I had ever had before and would help me to present better so I would not be discovered as a man.

As Paula wrote in and commented: "I don't know if we ever get over that fear of being found out, of being exposed and ridiculed. I think this is much more about how we see ourselves than how others see us, I look in the mirror and see all my history, the Dan Dare chin and the prop forward shoulders, others just see a late middle aged woman who happens to be on the tall side."

Thanks for the comment and as I am fond of saying, these days I present as old. Since the genders have a tendency to merge together later in life. I am also happy to have made it to the place I have in my life but as I near my seventy fifth birthday, I know the ultimate challenge is yet to come.  

A Genderless Journey

Image from the 
Jessie Hart
Archives

Recently I needed to take our car to the oil change place to get the transmission fluid replaced. 

In the past I have written concerning my paranoia of going to male dominated places. Since normally I am the only feminine person at the oil change place, the usual paranoia set in. The last time I was there, I was called "Ma'am" several times and had no gender problems so I did not really expect anything else this time. 

To prepare, I shaved closely, put on my foundation and contour blush with lipstick and was ready to go after tying my long hair back. Off I went to get the car serviced hoping I would not be mis-gendered. 

It turned out all my paranoia was baseless. I was treated with respect and not referred to as sir. Plus it turned out the whole process needed much more work than a simple oil change. So the manager was very much involved in the process. At times, he was so involved I wondered if he was trying to impress me. He even went as far as helping me turn off the "perform maintenance soon warning" off. Maybe I was the recipient of female privilege. Or, I needed help and he volunteered. 

Very soon the process was over and I was free to go (after I paid) and it was time to go through the drive thru of our favorite coffee place for a treat. The pressure was off and once again I wondered why I got so worried about going at all. Looking back, I have never experienced any negative feedback when I have gone to male dominated spaces. I guess I am afraid of being taken advantage of. When most of the time the opposite has happened. For the most part, men have bent over backwards to help me.

Maybe I will never change but I doubt it because the transition scars  run too deep. My gender dysphoria ran too deep as a transgender woman. It could be time to change my own oil.   

Playing the Victim as a Trans Woman

Image from Jen Theodore on UnSplash

It has always been easy for me to play the victim at times during my life.

Primarily, when times started to get rough in my male life, I could day dream of escaping into my female world .Usually I try to point out after a particular difficult day on the football practice field, I could wistfully take a look at the cheerleaders not so far away and instantly feel better. Of course, I was quickly brought back to reality by my position coach. Or by the offensive lineman who was intent of driving me into the ground. 

Over time my escapism became a habit, especially when I discovered how intense my feelings became when I cross dressed and interacted with my mirror. Suddenly I was not the victim anymore when I looked at the girl in the mirror. Which was all good until I found I wanted so much more than an image of a girl, I wanted to test my new self in the world. 

At the same time, my work was training me not to be a victim. As I rose higher and higher in management structures, I learned the buck stopped with me and I was only as good as my employees who worked with me. My problem then became carrying the same ideas over to my life as a novice transgender woman. Even though, I was still married to my second wife and was interacting with many many strangers on a regular basis, I was still extremely isolated and alone with my gender issues. Just cross dressing in front of the mirror wasn't enough and still I felt as if I was a victim. Why did I have to suffer from extreme bouts of gender dysphoria. 

The answer was always the same, I was stuck with who I was and I needed to somehow make the best of the situation. I dedicated my life to finding out more and more of what my wife was telling me when she told me I knew nothing about being a woman. I learned I did not and instead of being a victim, I needed a way to be allowed behind the feminine gender curtain. It wasn't until I made the decision to put my cross dressing ways mentally behind me and pursued ways to enter the world as a transgender woman did I begin to make serious inroads towards my dream. I know I am just dealing with labels to some but to me the distinction between transgender and cross dresser was huge for one major reason. A cross dresser to me just wanted to look like a woman and a transgender person wanted to be a woman. My ideas led to several spirited discussions on message boards as you can imagine.

As life moved on, I hated to be called a victim and did all I could to avoid it. I went to any extent possible to not going back to my former self feeling sorry for himself. In my own way, I felt proud of the fact I had been able to put all the self destructive behavior behind me. I was especially happy my suicide attempt had failed because I found I still had so much to live for if only I was able to reach out and grasp it. It was amazing when I stopped being a victim and was trying to live two gender lives was behind me. The pressure was off and my mental health improved. 

Playing the victim as a trans woman just didn't work for me. I did not have to worry anymore about what gender I would have to live as on any given day. When my dominate feminine self was finally given her chance to live, she took over and made my life worth living again. The icing on the cake so to speak was when she was able to make and flourish with a whole new set of friends which included my wife Liz. All of them never knew my old male self and I was able to build a new person from the ground up. 

Life was exciting and fun again or maybe for the first time ever. My old male self predictably knew how to be successful but never knew how to make friends and be satisfied. I was so fortunate to have been able to slip behind the feminine gender curtain and discover how the other half lived. I was accepted and loved it and never had to turn back.  

What Now? More Steps???

Image from Henri Pham
on UnSplash

As I view my progression into a transgender lifestyle, I see it as a series of steps. In other words once I arrived at one step I needed to look around and see what was coming next. 

It all started innocently enough after I discovered I could wear certain items of my Mom's wardrobe and admire myself in the mirror. After that step, I found I wanted to shave my legs, put on hose and a mini skirt I found at school and head outside to check the mail at our house. I knew I was hooked and needed to figure out what was next in my life. 

The next step was very difficult to come by as I mentioned in yesterdays post., I needed to acquire the makeup and then learn how to use it. My next step upwards did not actually come until my college days when I was able to buy a wig I loved for a girlfriend I had, then keep it when we broke up. Finally, I could complete the total makeup and hair step and I loved it. It was around that time when I became brave enough to attempt to express my feminine side at Halloween parties. Immediately I began to learn new lessons from the experience such as how I was separated from all the male friends I had when I was cross dressed as a woman. I was excluded from the club.

From that point onwards I needed to decide if I wanted to be excluded from a club I worked so hard to be a part of. It was a huge step in my life when I decided I should and would give up my male past and go forward as a transgender woman. Little did I know, when I made the decision, so many steps were to come. Such as when I began to enter the world as a woman, I needed to concentrate on so much more than just look like one. I compared the process with taking a mirror image and then putting it into motion. I needed to concentrate on femininizing my movements and then undertaking the biggest challenge of all, communicating one on one with the world. Which meant mostly women since most men had the tendency to leave me alone because their sexuality was threatened. 

My steps then came quicker and quicker the more I tested the world. Confidence came when I successfully negotiated one step after another and was ready to move on. At times the process was not easy when I thought I was moving too fast. I paused and began to consider how much I had to lose if I continued on the path I was on. I was on a collision course with the reality of my true gender. My next step just had to be gender affirming hormones or HRT. Fortunately I sought out medical and therapeutic help and was approved for the hormones. A huge step as my what now was answered. My body took to the hormones easily and I was able to flourish. 

Finally I ran out of steps and excuses and decided to give my male clothes to charity. What now became the future and it was time to live a life as a transgender woman. 

Complacency

 

Summer Image with padding.
JJ Hart

As I did my best to transition from male to female there were many times I experienced moments of complacency.

It happened slowly enough as I kept throwing lifelines to myself so I could survive a life burdened with gender dysphoria. To add insult to injury, I was not gifted with feminine external attributes to help me along as I initially tried to make it in the world as my authentic inner self. Disguising my testosterone poisoned body was a total learning experience. Angles needed to be changed into curves using everything from pads to balloons to foam. Anything it took to perfect my image and avoid complacency. 

The main problem I had was I could not avoid all the years I had lived as a man. The male trip was never easy for me to learn and even a more difficult time to forget. I had survived and even flourished and now I was trying to give it all up and for what. To live as a woman which became an all encompassing goal. I would practice the best I could walking and moving as a feminine person. Even to the point of being called "Ma'am" when I was at work as a man. I figured it was because I projecting a feminine "aura" to the world and resolved to add the idea to my accessories when I was out in the world as a novice cross dresser or transgender woman. 

I started to project very strongly that I was a woman to any stranger I was interacting with. Along with looking them in the eye, I was able to be accepted for the first time as the person I wanted to be but I still had to guard in not letting up my guard and not slipping back into any of my old male ways. Just one time walking like a linebacker or not paying any attention to my new feminine communication skills could essentially ruin my whole day. It did not matter how much time, effort or money I put into my appearance, if I forgot who I was, nothing mattered. For years, my entire existence was still so fragile until I put in the years and work to tip my gender balance.

I can't say, even today I don't experience moments of complacency. It is easy when the cis-women my age and younger are for the most part very casual in their appearance. Ironically, when I see a woman in heels and hose in the grocery store dressed to the nines, my "trans-dar" goes up and I want to take a closer look. Perhaps the person could be part of the transgender or cross dresser sisterhood. 

Through it all, complacency or not I have never forgotten how the differences in female fashion is and was one of the fun parts of transitioning. No longer was I confined by the drab and boring male fashions. I had forever admired how the woman around me had the freedom to express themselves through fashion and now I could also.

On another topic, I attended two other LBGTQ support group virtual meetings recently. The groups moderator is a trans man and does a good job of keeping everyone involved. The group is very diverse and I was surprised to see a couple of the transgender participants seemingly have partially de-transitioned over the years. Plus I learned the Veterans Administration has finally approved electrologist visits under their care and my mammogram was approved after four tries. The main problem was the hospital I wanted it done at still had an old chart on me with my dead name so getting a new one was the problem. The VA needed to approve the process and did so my dead name information has been changed on yet another document. Progress is progress I guess.

At least I was not being complacent and stayed the course until I saw results.

Sitting Pretty

Image from JJ Hart.

It never took me being a genius to figure out my appearance as a woman would cost me much more than my male self ever did. 

I started out my feminine life innocently enough as I began to save my meager allowance to buy a few articles for my girl wardrobe. I even took on a rural newspaper route to add a few dollars every week to spend on whatever I wanted. The problem was, finding my way to a store where I could attempt to spend my hard earned money. 

Our family home was actually in a rural area outside of town and I needed to figure some sort of an excuse to make it into town by myself because all I had was my bicycle. I figured out the answer which came to me when I was asked to go in town and visit my Grandma. She just happened to live very close to the downtown area and probably would not resist any attempts on my part to go downtown alone. I knew also, there were several stores downtown which sold makeup as well as other feminine accessories. So close but so far.

Predictably Grandma didn't and I had free reign to go shopping on my own. Then, the next biggest hurdle came along when I had to actually go into a store and shop for any makeup I found that may be suitable. The first time I was brave enough to shop for my own makeup, I was panicked and just wanted to buy something and get out of the store. Another problem was my Dad worked a short distance from where I was shopping and if I was caught, I would have no answer to why I was buying makeup. He never did catch me and the only hurdle I needed to face was the clerk who would be checking me out with my purchases. 

I was able to visit Grandma and do my shopping with no problems except for my extremely limited financial resources. Even though I managed to buy appropriate makeup, panty hose and even shoes, there was no way I could ever afford a suitable wig. For years, the wig of my dreams was just a fantasy of mine. Even so, time flew by and I managed to survive, even with my gender issues. It wasn't until I was out of the military did I realize how much sitting pretty would cost me. 

Dressing head to toe as a woman still proved a challenge for me to afford. Most of my needs would be met by going to thrift stores in our area. By doing so, I was able to find fashion "treasures" which were added to my growing wardrobe. While the thrift stores were cost effective for me, so many other aspects of cross dressing myself were not. Due to the size of my feet, thrift stores were out and I needed to shop retail. The whole process of adding new makeup, accessories such as purses and jewelry was a challenge because for the most part, my wife had control of the family finances. Through it all, going to a wig shop and buying a wig was still very difficult and frustrating. What I mean is, once I was able to put together a quality outfit, I was still struggling with having a wig to finish off my look. 

Finally, my financial situation improved to the point where I could afford a quality wig but then I needed to figure out which wig I could buy. Initially, I was like a kid in a candy store and picked out the wrong wigs which made me look like a clown. Through all my fashion errors when I was out in public for the first time, I finally was able to buy the correct wig which fit me well and framed my face correctly. It turned out the wig was the final piece of my presentation puzzle. 

For the first time ever, I was able to do my best and sit pretty as a novice transgender woman. 

Staying in the Present as a Trans Woman

Outreach Image. JJ Hart, Cincinnati 
Trans Wellness Conference 

Throughout my life, I  have experienced difficulties with staying in the present. 

Perhaps it all started when I started to raid my Mom's wardrobe and makeup and then briefly feeling really good about it. Then when the warm feelings began to fade, the day dreams began to set in. I could not wait to get in front of the mirror again.

As my life as a cross dresser grew more complex, so did my efforts to day dream my time away until I could attempt to enter the feminine world again. As I always say, I wish I could get back just a small portion of the time back I wasted on day dreaming of my gender issues.

Plus, all the day dreaming in the world could not keep me in the present as far as my ongoing life as a male was going. The more I needed to learn about successfully navigating a world I did not want to be in, the more I wanted out. Especially when I hit puberty and was facing all the changes testosterone was doing to my body. I did not want all the new angles to my body as well as the extra hated body hair which I had no choice over. I wanted all the curves the girls around me had. Changes I fight to this day through my gender affirming hormones or HRT. 

Ironically, I still struggle with my overall concentration as evidenced in my answers given to the nurse practitioner at the VA who monitors my depression meds and blood work. She always asks how my concentration is and I always answer fair and we move on. We have never really explored my answer and how I equate it with my life as a transgender woman. I guess it is our own version of don't ask, don't tell. She in fact has always known I am trans and has never held it against me.

For the longest time, the only person holding transphobic thoughts about me, was me. As I played the victim in my own life, I had an even harder time staying in the present. The main problem was I was attempting to lead a life with feet firmly planted in both binary genders. Being a man one day and a woman the next just was not a good way to live. In fact, my life was ripping me apart and causing me to mentally run. So I was increasingly not staying in the present as I played gender favorites in my head. My life as a transgender woman was so exciting and wonderful, my man self finally could not compete anymore. 

Then there was the anxiety of how my sexuality would play out if I transitioned into trans womanhood. Since I had never been sexually or emotionally attracted to a man, how would I survive if a man approached me after I had transitioned. Could I take myself out of the present and satisfy a man when I had no experience. I quickly found I did not have to worry when all of the sudden I was surrounded by women when I jumped the gender border. I gladly stayed where I was when it came to my sexuality and began to identify with the lesbians who were friends of mine.

I can't really say I can stay in the present any better at this time in my life than ever before. Hormones or not, I feel I am more in tune with the world around me. Which counts for everything.        

What Would Mom Say

Image from Jenna Norman
on UnSplash

This week my question to answer on the year long bio I am writing for my daughter and family as well as my wife Liz involved what parent I learned the most from.  

As I compared my Mom and Dad, easily I learned the most from Mom. Outside of the usual circumstances, I found I could find many more opportunities to spotlight Mom's influence on me. For example, I remember at a very early age watching Mom put on her makeup. Being a product of the "greatest generation" she was not shy about dressing up. However, I don't think watching makeup being applied led me to being a transvestite or even a transgender woman really mattered. Somehow the gender issues I faced went much deeper. Perhaps as deep as the medication Mom took during her pregnancy (DES) which was offered to women at the time to prevent problem births.

It turned out, I was successfully delivered just before my parents had decided to give up after three still births and adopt a child. I think because of all of that, my Mom put an extra emphasis on raising me and my brother who came along two years later. So much so, I wonder now what would have happened if Mom would have realized she had a daughter rather than a son. In all fairness to her, the fifties during my youth had very little information on gender issues. When it was available, gender issues were known as mental illness. 

Throughout the years, I always mistakenly thought girls had all the benefits in life I always wanted. Girls were able to wear the pretty clothes I wanted, be gifted the dolls I wanted and even never had to worry about being drafted and serving in the military. Male privileges were not known to me in those days because I had not yet earned any. As a side note, once I did earn the benefits of being male, I learned some of them were automatic and I did not want them anyhow.

I have forever wondered what my life would have been with Mom had I been born a biological female. Being as similar personality wise as we were, we fought quite a bit as mother/pseudo son and I have to think it would have been worse as a daughter. Mom was very headstrong and I am sure we would have had battles over fashion styles in the 1960's as well as when I could begin using makeup. In fact, when I was sneaking around using her makeup, I was probably younger than I would have been had I been her actual daughter.  I am sure too, Mom would have tried to influence me into going to her college and joining her sorority. She would have done her best to push me down a certain path which was certainly going against my generation's rules at that time in history during the upheaval in the later 1960's.

By this time, you may be asking where was Dad during all of this. It was not like he was not an influence in my life but he was not as hands on as Mom was. He was long on providing and short on emotions which I struggled with for most of my life. One thing I remember most about him was how desperate I was to never disappoint him and since I rarely if ever heard a positive from him, I never knew what he really thought of my life. He was blessed with excellent health and outlived my Mom by ten years and I never came out to him before his death from Dementia.

I did try to come out to Mom but it was a dismal failure for both of us. Predictably, when I told her I wanted to be a woman, she offered up mental health counseling. The conversation took place just after I was finished with my military duty and was never mentioned again until her death fifty years later. I used to hold her thoughts against her and was quite bitter but I gradually mellowed with age and came to realize she was just a product of her generation. 

To honor all her sacrifices, I used her first name as my middle name when I legally changed my gender markers nearly ten years ago. Had I had the opportunity to be accepted as her daughter from the beginning, it would have been interesting how our lives would have intersected. Way past the pushback I would have received for wearing my skirts too short and wearing too much makeup when I was a teenager. I know what Mom would have said. You aren't leaving the house looking like that. Maybe I should have thought of that when I tried and failed to dress that way later in life.  

 

Feeling the Pain

 

Image from Eugenia 
Maximova 
on UnSplash.

Learning on the fly all I needed to know concerning my authentic life as a transgender woman often resulted in pain.

The pain, early on mainly materialized when I rushed the process of going out in public as a novice transgender woman or cross dresser. Many times I was reduced to tears following being stared at or even laughed at when I was simply out walking around. I felt the pain for years until I finally realized I was the problem and sought out the reasons why. The main reason was (as I always mention) my male ego was dictating my femininized fashion sense. He was thinking attempting to dress sexy would somehow validate myself as a woman. Of course, it didn't and just made me look ridiculous. On the other hand, when I dressed to blend in with other women, they validated me as a woman.

My frustration and pain increased until I became fed up with the entire process and changed it. My thrift shopping adventures began to change to reflect my new fashion sense. I was held back in many ways by my budget and knowledge of what fashion I was trying to buy. Sizing was an example, as I struggled to find what looked best on my testosterone poisoned body. I did not have the benefit of having any feminine characteristics to begin my journey so trial and lots of error is what I went through. Every time I learned a fashion choice I made  just would not work, I felt the pain return again.

My situation improved when my overall confidence improved to a point where I was able to use the women's changing rooms. When I could afford to go to a mall clothing store, I always checked with a clerk first to see if I was to be accepted so as not to feel the sting and embarrassment later. In the thrift stores I went to, the changing  rooms were not monitored anyhow, so I never had to ask. As I said, when I had the opportunity to try on clothes ahead of time, my improvement rate went way up and my fashion pain way down.

After conquering most of my fashion pain, next up came my paranoia over communicating as a transgender woman in the world. Of course I quickly discovered I had no idea of how women communicate between themselves. I found myself on several different levels when I dealt with the world. Once I figured out I was not "fooling" anyone else and just resorted to being myself, my life improved. One level of woman just did not care and basically ignored me while another level was curious and wondered what I was doing in their world. Overall, I was learning on the fly and had my share of pain such as the one transphobic woman I encountered at a party Liz and I attended many years ago. She was actively harassing me about what my dead name was. She was so evil, the experience still causes me pain to this day.

Overall though, when I compare my transgender journey to others I read about, I suppose I have had it lucky. Even though I had suffered a lifetime's worth of pain when I lost my wife, several close friends and my business in a span of five years, I was able to find new friends and rebound. Mainly because the friends and Liz accepted me as my authentic feminine self. I guess karma was paying me back for a lifetime of wondering what I was doing about my transgender self. All the years of doubting my gender existence came back to be a strength when I quit being a victim in my own life. 

Sure I was transgender but suddenly it became a strength not a weakness and the pain was behind me.