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. 

     

A Spectator in my Own Life

 

Image from Author JJ Hart

There were many times in my life when I felt as if I was a spectator in my own life.

From the first glimpse in a mirror when I cross dressed as a girl, all the way to when I first went out determined to be a woman rather than just look like one, often I was on the outside looking in. Being on the outside was certainly not a great place to be. I literally spent decades of my life worrying about where I actually stood with my gender issues.

Along the way, I grew tired of being the spectator and wanted more inside information on how the feminine system I so admired worked. I discovered the hard way, I was not going to be allowed to learn more until I made the drastic step of increasing my transitioning efforts. Naturally, it was very difficult to do when I was totally immersed in leading a male life which I had become quite successful at doing. Overall, I was becoming the victim when it came to my life as a whole. I kept wondering why me when it came to my desire to live as a transgender woman. I finally had to shake it off and move forward with my gender transition before I lost everything I knew in life. 

It turns out the real culprit was myself.  I was afraid to face my truth and it cost me. I even tried to out run my desire to live as a woman by moving and switching jobs. Once I talked my wife into moving from our native Ohio to the New York City metro area. Then back again a couple years later. Living in different parts of the country was certainly an eye opening experience but did very little to help my gender issues. On the rare occasions it did like the night on Long Island when I went to a transvestite mixer and the hosts thought I was a cis-woman was flattering but did me no good the next morning when I crashed back into my male life. Then my poor wife had to put up with my mood swings.

Still I was a spectator in my own life when I walked down the long hallway in heels to get carded for my true gender to the times I did the family grocery shopping in sweaters, mini skirts and flats, I wondered who was that? It took me years to come to the conclusion the other feminine person was me and she had a right to be here in my life. Slowly but surely, I was building the life experiences needed to cross the gender border but it kept taking me so much time. I kept running into so many road blocks, I thought I was some sort of a gender construction engineer. 

Regardless as time flew by, it was time to put my gender cards on the table to finally determine which gender was going to be the primary provider in my life. What I attempted to do was live as much as I could as a novice transgender woman to see if the lifestyle was for me. Even though initially I did not attempt to do it, the trans life rapidly snuck up on me. Before I knew it and maybe before I was ready, I began to carve out a brand new life as a woman. Quickly I needed to develop feminine communication skills which was difficult for me to do since I was overwhelmingly dealing with other women in my life.

Through it all, slowly I grabbed total control of my life and became a spectator any time I was forced back into my old unwanted male life. In other words, I finally faced my own truth and flipped the ultimate gender script in my life.    

Luck or Destiny?

 

Image from Jan Tinneberg 
on UnSplash 
 

Is transitioning successfully across the gender frontier a matter of luck or destiny? 

I would argue a blend of both when it came to me. When I first started to explore the world as a novice transgender woman, I knew very little of what I was doing. Primarily in how I was attempting to present myself in the world as a woman. I was wearing what no other women would think of wearing as my male ego was sending me false messages. During this learning time in my life, I was lucky I only was laughed at or stared at. Sometimes I am surprised someone did not sneak up on me and attempt to pull my wig off.

No one did and I moved on finally learning how to better blend into the feminine world I was seeking to be a part of. Maybe, destiny was on my side for a change and even in my darkest hours of being a rejected transgender woman, I always thought there would be a future. So I pursued the sliver of hope I felt when I cross dressed and went out into the world. Just the smallest amount of gender euphoria kept me going towards my gender dreams. 

It took awhile of finally being lucky and being at the right place at the right time, when I started to actually began to build confidence in what I was attempting to do with my gender. Maybe I could put all those self doubts behind me and carve out a new life as a transgender woman. In some sort of a deep dark way in my mind, destiny was still pushing me forward. Especially in the times when I was out doing Christmas shopping for my wife as a woman and taking the time to enjoy all the holiday decorations in a way I had never had before. In fact, as my male self, I always wondered if I would feel any different with the decorations if I could ever view them as a transgender woman. My answer was a resounding yes, I could.

Luck and destiny did not end with holiday celebrations as I was just learning how to adjust to my new feminine life. Destiny showed me what it would be like when I began to lose my white, male privileges. The first time I obviously felt I was losing my intelligence stands out when I was mansplained over the simplest of topics as well I was shocked when I lost the personal security men enjoy. It was probably more luck than destiny which led me through unscathed and wiser. 

It wasn't until much later in life did I realize I was always destined to lead a feminine life. All my lucky escapes and experiences had combined to guide me ahead to my goal which sometimes I fought completely from happening. I did not know how much destiny was guiding my life. So much so, it was like a huge cloud lifted after tragedy of my second wife's passing. Suddenly I was free to pursue any gender life I wanted. At the same time, the US Veterans Administration health care system I was part of began to administer gender affirming hormones to veterans such as me.   And finally I was close enough to retirement age, I would not have to worry about working as a trans woman to support myself when I transitioned. 

There was no luck involved. Suddenly destiny had opened its door wide and showed me the path forward to a new feminine life I gad only dreamed of. All I needed to do was take the opportunity and run with it. 

Staring Down the Transgender Cliff

Image from Jimmy Conover
on UnSplash

 As I transitioned from my very active male self into an accomplished transgender woman, there were many times I found myself staring down a cliff on my gender path.

The more I walked on and was successful, the more scared I became. The cliff I was looking at, increasingly appeared to be steeper and riskier than I ever imagined when I first put on a dress and makeup so many years before. After all, I was risking so much such as a spouse, family and a job to name just a few. To add more pressure, I was becoming increasingly more and more successful in my choice of occupations. I had worked years to arrive at where I was and now I was risking it all to try to be a successful out transgender woman. By successful, I mean I was able to increasingly move about in society as I carved out a new life.

Mixed in with all the life changing experiences I was going through were many failures as I would sneak up to the cliff and look over. The entire process was scaring me more and more and threatened pushing me back into the gender closet I had worked so hard to leave for all of those years. 

Finally, I could take it no longer and began to gather the courage to take a leap of faith as I approached jumping off my personal cliff into a risky world I thought I knew something about. Before I did, I tried to come up with a survival plan when I jumped into the sometime snake pit which was the feminine world. I needed to learn the basics of the indirect passive aggression. Slowly but surely I learned to fasten my seatbelt and learned to ready myself to jump. I had conquered so much on my journey and it was time to quit staring down the gender cliff. 

Ironically, the women friends I had made like Liz and Kim helped me to a soft landing. They taught me what it would take to for me to become a transgender woman on my own terms. More importantly, all the fears I felt concerning my fear of gender heights proved they were like new gender guardian angels to me. Certainly, I found there were transphobes who would never like me but on the other hand, I found most people just didn't care. I was left alone to make a soft landing around my friends and enjoy my new life. 

I have always tried to be a proponent of the idea that something you are proposing to do will not be as bad as you think it will be or as good as you think it will. The same happened to me with I took the chance and gave up my male life and undertook the biggest adventure of my life. 

The soft landing off of the cliff coincided with my softer life as a transgender woman. When I did land, I wondered what took me so long. My excuse was I was afraid of heights, when in reality, I was just afraid of losing what was left of the white male privilege's I enjoyed. But it turned out, I could not have my gender cake and eat it too. It became too much pressure to attempt to live part time as a trans woman and a man. 

I closed my eyes, hoped for the best and jumped. It did not matter how intimidating the cliff seemed to be, the steep gender cliff proved to be the least of my problems.