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. 

Transgender Inspiration

The late Lynn Conway.

 In my formative years growing from a beginning cross dresser into a novice transgender woman, there were very few inspirations for me to follow. One of the few I knew about was the very accomplished and talented Lynn Conway, a computer scientist and electrical engineer.  

Deep down I knew I was not on the same level as Conway and the very few I did know about followed the same path as most transsexuals face when they transition into a feminine life. We were expected to leave our past behind, have all the needed operations and relocate ourselves to start over. Since I was my usual stubborn self, I could not see me going down all of the same roads as well known transsexuals. In fact, I knew a couple trans women nearby who were ready to go down the surgical road and change their lives forever. 

As in most cases each of their lives were totally different than mine. So they were more of an interest to me than an inspiration. By getting to know them closer, I had hoped to gain more knowledge of what I would face if I decided to go further with my own gender transition. I did learn, as I went on, everything was different when I was living as a transgender woman. I had my own preconceived ideas of how it would be to live as a woman from all the years I had spent closely observing the women around me. However I found most of my conceptions were wrong as I slipped behind the gender curtain. The prime example was how I was presenting myself as a woman. I wasn't dressing to blend in and was drawing unneeded attention to myself. My efforts came from my old male ego dictating my fashion and wardrobe. I had no inspiration to guide me the correct way.

I think I tried to use my second wife as inspiration but I was just not in the proper mental space to accept her criticism. In other words, my feminine self had not had the chance to grow up past my adolescent years as a trans woman. During those years, happiness was looking very lonely as my wife and I constantly fought over my appearance among other things. I think she knew she was fighting a losing battle as my internal feminine self fought with her all the time. Every now and then, I did talk her in to going out to eat as two girls and I really tried to dress down for the date. As a matter of fact, if I dressed down any more, I might as well just have gone as my male self. 

I was getting nowhere fast in my quest to learn more about being a quality transgender woman, so I was forced out on my own. Which added in it's own set of problems. Primarily, here I was sneaking around behind my wife's back to see if I could live as a woman. In doing so, I found I could create another life. Furthering the divide between my wife and I.

The divide widened until her death and inspiration or not, I continued on with my search for my feminine self. What I discovered was, she was with me all along. Just waiting for a chance to live. When she did, she became my own inspiration and I never looked back. In many ways I found she adopted many of the mannerisms and personality of my Mom, who was very outspoken and not shy. I admired her so much, I took her first name as my middle name when I legally changed my gender markers. 

These days, with all the internet and social media access transgender inspiration is much easier to come by and we need the inspiration with all the negative coming our way from politicians. We have to do all we can to keep the positives coming.

I Am I Said

 

Archive Image, JJ Hart

One of my favorite Neil Diamond's songs is "I Am I Said". I particularly was drawn to the line saying I was lost between two shores. Neil was referring to New York and Los Angeles and I adapted it for me to signify being lost somewhere between being male and female.

The song's lyrics go on to say "I am, I said to no one there " I again felt the same way because I had no one to discuss my gender issues with other than the occasional therapist who went quickly through my life with little or no benefits until I reached a point much later in my life. In addition, the pressure to conform to the successful male life I was leading was intense. One of the few positives of my job was I was named a managerial training manager so I was able to take medium ranged business trips from my home in Ohio (yes I am from the much maligned Springfield) and travel by car to Lexington, Kentucky. Usually, I was asked once every six months to make the trip which I quickly saw as an opportunity to pack a few of my feminine items and cross dress. 

I usually worked it out with my second wife I was taking a second night at the company headquarters so I would not have to drive back at night. When I did, I was able to either cross dress and head out to one of the Lexington gay bars. It turned out, there were several back in those days, since the University of Kentucky is there. When I went out, at the least I didn't have to tell the chair or mirror I was actually someone feminine. On one occasion, I hit the jackpot and my training seminar just happened to coincide with Halloween. I thought ahead and when I packed away from my wife's prying eyes, I added a few slutty outfits to put together a Halloween "costume." The difference this Halloween was I was going to try my luck at going to a big straight club and not a gay venue. After a few wrong turns, I found the place and gathered my courage to go inside. Here I was dressed in an all black mini-dress with black heels, hose and blond wig doing my best to ignore all the guys pinching my behind as I walked across the dance floor, Since I needed to be up and fresh early the following morning, I needed to be back early to go to bed.

All along, I was learning what I was and was finding out the hard way what could happen if I dressed the wrong way. One night, I decided to stop at the halfway point on the way home which was Cincinnati. I got a hotel room and proceeded to seek out one of the more infamous gay bars in town for hookups, I thought since my black outfit worked so well before, I would try it again. This time, a very drunk guy at the bar tried to pick me up...until his wife showed up. I was embarrassed and was trying my best to back pedal from the whole situation when he made things worse by telling her why did she not have legs like mine. By this time, I headed for the restroom to hide and when I came out they were gone. As was the black outfit.

Through it all, all the lying I was doing to my wife was wrecking my moral code and when I asked who I was, I did not know. Which made the Diamond song so important to me. 

Finally, I did climb out of the pit I was in and was able to learn who I was but sadly was never able to reconcile my transgender life with my wife before she passed away. All along she was urging me to find myself and by the time I did, it was too late. I was no longer stuck between two gender shores. I had found myself and she was feminine. 

It Was Never Easy

I am amused when anyone thinks my gender journey has ever been an easy one. 

To begin with, I was born into a very male dominated family. Being the oldest son of two, I had heavy male expectations forced on me. Very early on, I learned I was in the wrong place at the wrong time. I did not belong in the male world at all. The problem was coming to the knowledge I did not belong as I was sneaking around my family's back to cross dress as a girl. As I remember, I had two hiding places for my small collection of feminine wardrobe and makeup. 

The first place was up in the attic of our family garage and the second was more creative when I discovered a hallowed out tree trunk in a woods next door to my house. What I did was use plastic trash bags to protect my precious belongings from the elements and it provided an extra way I could be alone and dress which relieved (for a day or two) my gender tension. So none of my drastic measures were easy but I survived without anyone detecting my secret, to my knowledge. 

As years went by and my life as a girl began to be more complex, I was pressured to do more and more to protect my life. Sneaking around became more intense as my wardrobe increased, along with my knowledge of the makeup arts. In all fairness to me, I attempted to ease my gender pain, I told my first and second wives ahead of our marriage I was a transvestite or cross dresser which I thought would help my world. My idea worked for awhile, until I essentially out grew the idea I simply wanted to wear women's clothes and makeup. More and more I wanted to be a woman.

Making the jump from cross dresser to transgender woman often was brutal. Partially because I still had my male life to contend with. It probably would have been easier on me if I was not involved in such a male intensive job which automatically would completely throw me totally and publicly back into a world I never wanted. Ironically, my life as a man I worked so hard to build was now in direct competition with a feminized life I was growing into. 

At the same time, my biggest challenge became was deciding if I was transgender at all, Could I continue a life where I lived in both binary genders temporarily or would I need to choose between being a man or a woman. I ran from the decision for years before I grew so tired of running I could go no farther. Making a decision was never an easy one but one I needed to make. Finally, one night I had yet another soul searching discussion with myself and decided to live a life as a transgender woman. The world as I knew it was showing me the way. For the first time in my life I was single and did not have to worry about a spouse to deal with when I changed.

I went even further and decided to go to a doctor to see if I was healthy enough to begin gender affirming hormones. I was and my body took to them very rapidly, making my decision to give away what was left of my male wardrobe to charity and add to my feminine wardrobe. It was not easy to make the decision but it was easy to live with the results. I only knew my new feminine life would never be easy but still would so much better than the life I had lived,

It was never an easy life and my gender dysphoria certainly did not make it any easier. Waking up in the morning after dreaming if I was a boy or a girl never got my day started on a good foot. All of it became some sort of a daily routine I never wanted. With all the highs and lows, somehow I learned to live with it all. 

Options or Paradise

 

Liz on Left, out to eat! 

During our gender transitions, many times we have the choice of options or paradise. 

Often, options come about as not being a choice. Examples include all the days we had to rush around and hide our feminizations from our family and friends. We had no option but to hide our truths. For some if us also, our cross dressing options never became any better when we had to pursue stints in the military. Certainly, the military provided every roadblock in the world for pursuing any route to paradise for gender conflicted individuals. 

As a whole, back then, paradise was very difficult to achieve. In fact I can now refer rare paradise as gender euphoria. For many years and even decades my gender balance never changed. I was still sneaking around risking life as I knew it to momentarily express my true inner gender. Fortunately, I had the time to work on perfecting my femininized presentation. When I finally was able to pursue paradise by going out in public, I was closer than before to achieving success. In fact, once I learned to blend in with  other women in the world, I was more likely to find a fleeting sense of paradise. 

Usually, my paradise did not last long because I needed to quickly return to my male world which I was increasingly feeling uncomfortable in. I was desperately seeking other options to find more gender euphoria other than the annual Halloween parties I was going to as a woman. The parties and the transvestite/ transsexual mixers I started to go to helped me to understand the gap I was facing when I considered the ultimate outcome of where I wanted to go with my life. Instead of just embracing the usual male attributes in life, I needed to include the very real possibility I would have the option to live life out as a transgender woman. The reason I thought this way was I encountered paradise when I was experiencing the world as my true authentic self. I felt so natural and wondered why I had waited so long to do it.

What if I had experienced paradise a decade earlier than I did when I went to a TGIF restaurant and bar determined to mix with other single women. Maybe I was just waiting for the world to catch up to me but more than likely the opposite was happening. I had the options to catch up to the world and I took the chance. By the time I ventured out into the world, I had certainly paid my dues and was  ready to reap the benefits. 

Still I was frustrated when the benefits of my new life were just out of reach. Such as the times when I was so comfortable in my new feminine world I actually forgot where I was and caught myself slipping back into a male mode. I still did not have the full closure from my old male self I so desperately needed. I kept running into unexpected roadblocks and stop signs on my gender path such as a spouse's death which changed my ideas of where I was headed but not for long. Soon with fewer and fewer options to consider as well as a solid new life I was building, paradise was closer than ever before. 

As transgender women or trans men, we often experience periods of options or paradise as we follow our difficult, unique gender paths which separate us from other humans. The whole journey hopefully makes paradise worth it.  

Just Weary

 

Image from Harry Quan
on UnSplash

Following a lifetime of doing my best to maintain a male lifestyle, I grew weary of living a lie.

Similar to many transgender folks and/or cross dressers I grew impatient with the progress I was making with my gender transition. I had two main problems, the first of which I did not know where I was going and the second was I had no basic idea if I was ever going to learn the basics of what I was doing. Very quickly, I tired of just looking at myself in the mirror and wanted more. I wish now I would have seen my feelings as being transgender but all of this occurred well before the term transgender was invented and became popular.

At the time, my frustration level was rising to an all time high. I was doing my best to learn the basics of feminine presentation but rarely had the chance to try my efforts in a public setting. Those occasions just happened to be Halloween parties which I learned many new basics from. Such as what happened when I dressed slutty compared to when I dressed in feminine professional attire. As Halloween rapidly approaches, I will try to be more in-depth on what I learned which helped me along on my journey to be a transgender woman.

As I went along, my femininization lessons just increased my weariness of being male. I grew extra tired of all the games guys play when they size each other up in the world and I wanted out. I could not wait until I could head home and escape into the safety of my woman's world, The whole problem was, my world was still so isolated and I needed to get out. To enter the world, I dreamed up ways to do it and began by going shopping where clerks had to accept me for my money, not my gender. I also started out by going to gay bars thinking I was safe there. In the long run, I discovered neither did me much good as I was not challenged to build a better feminine self. As I said, acceptance was a given in the clothing stores I went to and not a given in the gay or lesbian venues I went to. Through it all, with the ups and the downs, I learned I was on the right track to my gender discovery. Even though I needed to make sure the light up ahead was not another on-coming train.

My salvation turned out to be being myself, as I ended up going full circle and enjoying the sports venues I enjoyed going to as a guy. Sure I was scared at first, but I followed my instincts of being friendly to the staff, dressing to blend in with the other women and tipping well. Before I knew it, I became a regular at several venues as I enjoyed myself. During this point of my life, even though I was still intensely lonely, I still was increasingly weary of any idea I was still a man. 

To do away with any of my masculine traits became a primary goal of mine. I worked hard to lose weight and take care of my skin to do my best to improve my femininized appearance Plus the addition of the gender affirming hormones I began very much improved my confidence and outlook on life, I finally had arrived at my gender tipping point when all the male clothes had to go and it was time to consider coming out to the closest friends and family I had left. 

It was time to leave my weary life behind and open the doors to an exciting new life as a full-time transgender woman.  .