Having it All as a Trans Girl

Archived image
after Beauty Salon. 

As we negotiate difficult gender journeys on the way to becoming our authentic selves as transgender women or trans men, we find it is tough to have it all in our lives.

Many times, as we give up much of the baggage we have accumulated in our old lives, we have to give up spouses, families and even employment. On the plus side, if we have the chance, we can build back better in our new lives. In fact, I was told once by a woman I knew, I had an unique situation. I was starting all over in life where as most other humans never have the chance to do. Before I could get there, I needed to do quite a bit of work.

Early on, I obsessed on my feminine appearance, wrongly thinking it was all I needed to do to make it in the world as a cross dresser or transgender woman. Seeing as how my wife was fond of calling me the pretty princess all the time and I knew nothing about being a woman. Now, I wish I would have listened closer to her. As it was, I did listen to the point where I really began to work overtime observing women to see what she meant and it was not enough. I still didn't understand and my male ego continued to get in my way when I happened to have a successful night out cross dressing. Like the evening I went to a transvestite mixer and was carded at the door to prove I was a guy and not a cis-woman. My defense was I had to know what a woman was if I had been mistaken for one the night before. Plus, somehow I held my gender dilemma against my wife because she would not help me,  As  I always mention, it seemed my wife and my male self ganged up on me to slow down my transition. Both had a losing stake in the process if I made it.

At any rate, I said to hell with them and set out to look behind the sacred feminine curtain to see if I could survive. Quickly, I learned not only could I survive but just possibly I could thrive as a transgender woman. In order to make my way behind the gender curtain, I needed to really learn the basics of communicating as a woman, mainly with other women. I found I had a curious audience of women wondering at the least what I was doing in their world and at the most, learning I was not any sort of a threat. For awhile, my life was moving fast and I was close to seeing what having it all might mean for this trans girl. It all became tantalizingly close. 

So close, I kept moving forward as fast as I could, especially when the forces which were holding me back began to weaken and disappear.  It became easier and easier to toss my old male baggage in the trash and acquire new feminine luggage, The turmoil I experienced at once was the toughest, saddest moment of my life coupled in with a few of the most exciting times I had ever experienced. 

Even with all of my changes I was going through as a transgender woman, I still didn't think I was ever on the edge of having it all. Life is just not built that way. Primarily with the help of a small group of very accepting women friends, I was able to come close and open gender doors which were previously closed to me. I was able to never look back at a male life I never really wanted.

A Vocal Trans Girl

 

Image from Brooke Cagle
on UnSplash

The other night when we went out to eat, I needed to order what I wanted food wise loud enough to be heard above the noise of a busy restaurant. 

That meant projecting the best I could, my feminine voice to match my appearance. So many times in my past as a transgender woman and or serious cross dresser, I thought I had done a great job with my makeup and fashion only to destroy it all when I opened my mouth to talk. I could see the surprise in the other person's eyes when they discovered something was not quite right with the picture I was presenting. 

For the longest time, I tried to avoid talking to people all together. It seemed to be a good idea until I realized when I refused to talk, I was just coming off as being mean or standoffish...if I was lucky. Or worse yet, I was coming off as a bitch. So to preclude it from happening was I needed to improve my communication skills with the public. Mostly other women, since men had a tendency to leave me alone. At the least, I had only one gender to deal with as I was testing the world as far as my communication skills were tested. Initially, to sooth the panic I felt when I dealt with other women, I attempted to mimic their voices, which worked to an extent until the conversation became too intense. When it did, I was on my own to see if I could be the total package as a transgender woman in the public's eye. 

All was good, or so I thought, until I decided to go farther and farther in my femininization. I started with attempting to look close to the same as far as the wig I wore and the fashion choices I was wearing. No more trashy style as I attempted to blend in and build the woman I wanted to become. The whole process at time became too intense for me as people around me wanted to know more and more about me. Basically, what was I doing in a woman's world? To answer them, I needed to learn to communicate as a whole new person. I needed to put my straight forward often blustery male communication behind me and be more careful on how I chose my language. 

In order to aid in my vocal trans girl process, I even attempted feminine vocal lessons from an expert the Veterans' Administration assigned me. Of course my "coach" and I worked on how I formed my words but also more importantly addressed what I was saying. I learned the words women used more often to communicate what they are trying to say. During the course of my coaching, I had weekly homework I needed to work on diligently so I could do well the next time I went in for my vocal coaching. My goal was to attain all the extra communication knowledge I could from the help and move back into the world and try it all out. It has been difficult for me to judge how effective the vocal program was but I felt every little bit helped in my quest to communicate as a vocal trans girl.

Plus, I would be remiss if I did not mention the biggest gender flip of all, the switch from male active aggression to female passive aggression. The change to me meant, I needed to be more careful in how I chose any words I perceived to be negative when used with another woman. Which also meant, I needed to be on the outlook for hidden meanings when I was addressed by other women. Especially being told I was attractive...for a man dressed as a woman. 

Overall, I think being a vocal trans girl has been the most difficult part of transitioning for me. Since I was always shy, slipping back into being more or less and introvert was easy but not satisfying. I enjoyed the challenge of putting together the final big piece of my gender puzzle which was communication. Once I did, life became much easier when I could stand up again for my gender self. 

All my efforts at the least helped me to show other women who for whatever reason did not view my presence in their world as a negative and they helped me to succeed more than they ever knew. 

Down the Transgender Rabbit Hole

 

Image from Benoit Baumatin on UnSplash.

Long ago, I sought out a rabbit hole I found I did not want to escape.

In the beginning, I did not go deep into the hole so I could supposedly easily escape if I wanted to. The farther I went, the harder it was to escape even I wanted to. What happened was gender euphoria set in and the entire cross dressing experience became increasingly pleasurable as well as feeling incredibly natural. The problem I faced was how to cover the entrance to my rabbit hole so no one else in my family could discover it. Very early it was easy when I could attempt to borrow select clothes from my Mom's closet which ended when I became too big to wear them. Then I had to rely on my own limited financial resources to buy fashion and makeup accessories. 

For awhile, the pressure to go away and cross dress became so intense I needed to find a spot away from the house to establish another private rabbit hole. I found the best spot in a quiet wooded area next to our rural home. I was able to protect my secret collection of feminine clothes in plastic bags and hope they would be protected enough as well as not be discovered. I did well, because they never were and I was provided another place to go to cross dress. If even for a short period of time. 

The better I became at perfecting the "art" of fashion and makeup, the more I wanted to leave my novice transgender rabbit hole and look around at the world. At first, the world proved to be a very difficult place to be. After too many public failures I was sent scurrying back to my rabbit hole to seek comfort and try to figure out what all I was doing wrong with my feminine presentation. The entire feminization process for me proved to be a difficult one as my entrenched male self fought for his dominance and kept on trying to cover up my rabbit hole with ill advised purges. Very quickly he found out the gender purges I was going through were a complete waste of time and money. 

Once I reached the middle portion of my life, my rabbit hole needed to be expanded from a crossdresser rabbit hole into one large enough to contain a full fledged transgender woman. I needed room for more wigs, shoes and women's essentials to survive in the world. As I was entering a new exciting yet scary world without my white male privilege, the sunlight outside my rabbit hole was at times blinding. Even more so when the world all of a sudden expected me to communicate with them when at the least, I had to order face to face with servers or bar staff trying to take my order. What was a novice trans woman to do? What I attempted to do was make the best of a potential destructive situation. Very early in the game, I came to the conclusion the world knew I was transgender for the most part and those who cared, could just get over it because I was just living my truth.

Of course, once I was able to leave my rabbit hole in my past and live, I had no desire to go back to it's dark confines. Each time I was successful in the feminine world, my male self lost more and more of any control he had left. 

The writing was on the rabbit hole wall when I started gender affirming hormones. I knew I had made the correct decision when my body and mind took to the new hormones so naturally. In addition to all the bodily changes which took place, I cherished the new emotions I felt. Being able to cry for the first time in my life was quite the experience. 

Perhaps, most importantly, was when I discovered the lack of predators I really had when I left my rabbit hole. Of course dealing with the occasional man was a problem but with my circle of lesbian women friends, not so much as they taught me true validation as a person. Once I learned to validate myself, I was freed from my old male rabbit hole for good and jumped into the sunlight.

Transgender Expectations

 

Picnic Image. My wife Liz on the right.

When I began the long and very difficult transgender journey I decided to take, I had many expectations.

At the time, I was still entranced with wearing all the pretty clothes a woman had access to. I could not wait to have my own wardrobe which would match any occasion from casual to formal. I was very naïve back in those days and thought a woman's life was all about how she looked. I was so wrong as I discovered as I explored more and more of a transgender woman's life. In addition to the layers cis-women went through in their lives, trans women face all of those and more. To begin with, we don't have the benefit of growing up around other girls and learning from them. Making our own way was difficult when the only input was coming from the mirror. 

Loneliness ruled my feminine side all the time my male side was trying his best to survive in the world he never really felt comfortable in. As I observed all the girls around me, my expectations of what their life was all about just increased. The problem was I had a distorted view of everything feminine. One example was I was shy and never liked having to ask a girl out on a date. I thought the whole process was so unfair just like worrying about serving in the military and getting shipped off to Vietnam. 

What I did not realize was the gender grass was not always greener on the feminine side. Was it easier to be the one asking someone out, or waiting for someone to ask you out. As far as the military went, there was nothing I could do about it, so I tried to hide my resentment and move on. 

As I did move on, I discovered many other expectations I never planned on. Communication was one of the major hurdles I needed to overcome before I could learn to live a quality life as a transgender woman. I was blindsided quickly when the public wanted to talk to me faster than I was ready to respond. Initially, before I went through vocal lessons, I tried to just talk in a soft background voice and hope for the best. Trying to match the voice to my appearance was not an expectation I planned on but it happened. It was just all a part of moving out of the mirror and into the world. 

As I matured as a trans woman and started to communicate with other women, I learned the grass was certainly not greener on the feminine side of gender. As I thought back to the Christmas envy I had because of my two girl cousins who were dressed in their new dresses and white tights. Liz ruined my illusions of pleasure when she told me stories of getting in trouble for getting her tights ruined by playing with the boys. 

Even though I found the grass was not greener on the other gender side, the more I learned of the gender differences I faced, the more I wanted to continue my journey. It seemed the more I experienced, I more I felt I had paid my dues as a transgender woman. More or less, as a rite of passage such as a mammogram. 

Since females are not born women but rather socialized into womanhood, transgender women have to go through the same process. By following all those expectations all those years, I finally arrived. The path I followed was difficult but in many ways the same as other women, transgender or not. 

A Point of No Return

 

Image from the Jessie Hart
Archives.

For nearly a half a century I considered myself a more or less serious cross dresser or transvestite. In addition, I considered the transvestite label little more than just that, a label which was appropriate just to  use around others. Even though I rarely told anyone else about my gender issues.

The only people I can remember telling would number under ten before I finally came out into the world as a novice transgender woman. The first people I ever trusted enough to share my biggest secret oddly enough were friends I had in the Army. My disclosure came after I risked what was left of my time in the Army by dressing totally as a woman for a Halloween party.  Following the party, several weeks later under the influence of great German beer, the subject of the party came up. Of course then, the conversation went to what our costumes were. 

When the subject turned to me and how good I looked, I gathered the courage and told the three others the night was not the first time I had cross dressed as a woman and in fact I was a transvestite. I ended up taking a major leap of faith telling them because I still had approximately six or seven months to go on my enlistment and conceivably I could have encountered problems if the gender information I disclosed got into the wrong hands. After making it so far towards an honorable discharge, I certainly did not want to destroy the time I had put in. Plus, what would I tell my friends and family at home when I arrived back there early. 

To make a long story short, nothing negative happened with telling my friends I was in reality a transvestite and the experience was very liberating. On the other hand, I was not going to tell the rest of the world my secret. Of importance is the fact one of the people I told that night turned out to be the mother of my child and future wife. So I did not have to worry about telling her once we became married. I see her to this day and we still get along. Sadly, the other two friends I told are now deceased and I lost track of them almost completely before they passed. 

All of this brings me to the next person I told which was my Mom. It happened one night shortly after I was discharged and I was living at home for a very short while. One night when I came home from partying with my friends she was waiting up for me just like back in my college days. Somehow the conversation turned to my life and what I was up to. Out of the clear blue sky I decided to tell her my deepest secret about being a transvestite. I was still feeling liberated from telling my friends in the Army and felt secure in telling her, betting she would never tell my Dad. Just about the time I was feeling good about including Mom in my world, she turned around and roundly rejected me. All she really did was offer to pay for psychiatric care to solve the problem. Very quickly I rejected her offer and said no one was going to, in essence, plug me into a socket for electro-shock therapy.  From then on until she died, the subject of my growing gender dysphoria was never brought up again. 

The last person I came out to when I was still in my gender closet was my second wife. I write extensively concerning our gender battles but the fact remains she supported me as a cross dresser until I began my transition into a transgender woman. In essence, over the span of our twenty five year marriage, we just grew apart until her untimely death. 

Once I reached the point of no return in my male to female gender transition. there was no point in worrying about telling anyone I was transgender. It was obvious to the public who interacted with me what I was and they were left to draw their own conclusion. All of a sudden, all the pressure was off of me. All I needed to do was to do my best to present to the public who I really was. Plus, I would be remiss if I did not mention the roles gender affirming hormones played in my experiences. I was so happy with the results I was experiencing, I never wanted to go back to a testosterone filled life. For once, a plan came together for me and the point of no return never had to be challenged. 

Doing the Heavy Lifting as a Transgender Woman

My wife Liz on left
from the Jessie Hart
Archives

 Even as a young novice cross dresser, on occasion I felt I was doing the heavy lifting as far as looking the best I could in front of the mirror.

Little did I know, the real heavy lifting was still to come if I ever wanted to achieve my dream of living a fulltime transgender life as a woman. All I knew at the time was I wanted to mimic all the girls  around me in their colorful, pretty clothes and fashions. I never considered how complex a woman's life really was and how much more I would have to learn before I could gain my chance to fully play in the girls' sandbox. 

During my life, at least two opportunities to grow as a transgender woman came quicker than expected. The first happened when I came to the conclusion I wanted to be more than the "Pretty, pretty princess" as my second wife called me. In essence she was referring to the correct fact I lacked the socialization in the world to earn womanhood. She resented the fact, if I put on a dress and looked attractive I thought I had arrived. To make matters worse, she did not want to lose her husband to another woman. Especially if the woman was me. 

To prove her wrong, I set out to discover what she was talking about. Through more error than trial, I found out the hard way about dealing with men from a woman's viewpoint. For awhile, it seemed everytime I turned around, I was facing a new struggle like the time I was cornered at a party by a huge transvestite admirer who was trying to move in and have his way with me. All the way to the motorcycle rider my wife started a conversation with when we were in a bar one afternoon waiting for a cross dresser mixer to begin. For the first time, in both situations I felt helpless to do much of anything about what was going on. What was I going to do if the motorcycle guy asked my wife to go for a ride and I was left behind as the "princess?" All my male power privileges' were gone and I had nothing to fall back on. 

These were the days before I found the small group of women friends who helped my socialization process and very much jump started my femininization past any point I thought was possible at the time. In addition, validation and confidence became key components of my personality. My new lesbian friends validated me and gave me the confidence I needed to exist in my new life. It wasn't so much they accepted me as another woman but did just accept me as me. Which was all I asked. 

Through it all, there were predictably good and bad times. An example came one night when my wife Liz and I went to a lesbian Valentines dance she was invited to through a group she was in. When Liz got up to get us some refreshments, I was basically attacked by a transphobic woman who wanted to know what my real name was. Like it was none of her business. Which is exactly what I told the hater. For the most part, I was lucky and escaped unscathed on most occasions. I thought I was going to have some problems one time when we all went to a women's roller derby event in Cincinnati and received a few evil looks but no one said anything and the dollar beers were great!   

The other quicker than expected moment of my trans life occurred when I needed to learn all over again how to communicate with the world. I found if I looked the part of a woman and wanted to interact as one, there were many basic differences I needed to learn. There were to be no more frontal male verbal assaults, only passive aggressive, often behind the back comments which were only the beginning. I even took feminine vocal lessons to improve my communication skills in the world. 

One of my biggest regrets is my second wife did not live long enough to see my development as a transgender woman. Even though I doubt if we could have stayed married, I hope we could have stayed friends. After I did most all of the heavy lifting away from being the "Pretty, pretty princess" as she called me.  

Saving my own Life

 

Image from the 
Jessie Hart Archives

As I began to transition into a transgender life in earnest, the more and more I knew I was saving my own life.

As I mentioned in yesterday's post, all the obstacles I conquered on the gender path I was on just made my entire life more complex. Every time I met a stranger and established myself as a transgender woman to them was a new exciting time but not one which had it's share of fear. After all, I was losing all my well secured male privileges I had worked so hard to have. As a guy, I knew how to react to almost any situation negative or not. As a trans woman, I was in a different world and still had so much to learn. When I was first confronted with losing part of my so called intelligence in a group of men I somehow found myself in, I knew then my life had forever changed. I discovered the men just wanted to ignore me and my thoughts on what they were discussing.

In order to save my life, I needed to adopt what the other women in the world around me were doing. In many ways, they ignored men the same way men ignored women and it became very evident to me why the two main binary genders had a difficult time communicating. I was lucky because after my male upbringing, I had many of the tools to understand what men were really saying. While, at the same time viewing their comments from a woman's viewpoint. Even though the whole concept seems so easy for me to grasp now, back then, I really needed to understand which side of the gender fence I was on since for the longest time I tried to live in both a female and male world.

Soon, I found myself in a gender pressure cooker. On one hand, I had all the male positives to live by which I had learned to expect. On the other hand, the new and exciting (but scary) feminine side of life was increasingly opening gender doors for me. Since I was beginning gender affirming hormones, my world became a softer more sensitive place to be in. The ripping and tearing of my reticence to make a final decision on how I was going to live was slowly but surely destroying me. I was stuck in a gender world never never land which I would not wish upon my worst enemy and I needed to get out and save my own life.

It's no secret what decision I finally made. With the help of several close women friends, I donated all my men's clothes to a thrift store and never looked back. I equate the entire process with jumping off a huge cliff, then having a soft landing in a feminine world. It was difficult, yet it saved my life by making life fun again while at the same time restoring my mental health. 

Saving my own life never felt so good.    

Making the Difficult Easier

Image from the
Jessie Hart archives.

I spent years and years admiring every aspect of how women and the girls around me conducted their lives. I was dazzled by how they moved and interacted with the world. 

On so many levels, I wished I could be just like them but for so many reasons I could not. No matter how hard I tried, I couldn't shake the shackles of my pre-ordained male existence In order to survive in a male world, I needed to copy and succeed at being a guy. All of made the dramatic gender transition I was about to make later in life that much more difficult. 

As I moved from a cross dressing mirror into the real world, I discovered the feminine gender had so many other layers to their life's than I ever imagined. So much more than merely looking like a woman which turned out to be the way I could slightly open my closet door to the world. When I worked my way past the first layer of cis-gender women I faced in clothing stores and malls, then the hard work started. 

All of a sudden, I found myself in a position where I needed to communicate with the public as a novice transgender woman. In the past, my second wife had told me repeatedly in no uncertain terms I did not know anything about truly being a woman even though I was becoming fairly competent on looking like one. She was right and I didn't understand it. 

One vicious argument comes to mind from when we lived in the New York  City metro area and happened the day after I went to a transvestite mixer. What happened was, I needed to show my identification card showing I was really a male to even get in. For the next couple of days, I was on a massive ego trip which led to a big fight with my wife. It led to her comment I still vividly remember when she said I made a "terrible" woman. I could not believe she could say it after I had almost been refused admission to a cross dresser party for looking too much like a woman. When I told her my problem with what she said, she promptly told me, she wasn't referring to my appearance. From then on, I was determined to find out what she meant. It was difficult to do because my wife did not particularly care for my feminine side, so I was on my own.

It was only easier when years later I was able to break out of my old male bonds and be able to finally play in the girls sandbox. Along the way, I had learned the power of non-verbal communication between women as well as surviving the effects of passive aggression when I had to guard my back from smiling faces. When I did, my mental health improved along with my self confidence as a transgender woman. I came to realize (with help from my friends) while I could never be a cis-gender woman, I could be a proud transgender person. I achieved my womanhood through a different path but I made it. My presence in the group just made it more diverse and nobody questioned me about my past.  

In order to do it, I needed to reverse years and years of male life. Moving like a woman needed to become my primary goal since I was never going back. Also very difficult was how I was speaking to the world. I did my best to mimic the women around me and even took vocal lessons for awhile. Eventually all the work came together and I became confident in my abilities to survive in the feminine life I had always dreamed of. 

It Was Never Easy

Image from Alexander Grey
on UnSplash

 Two things amaze me when people bring up to me when they learn I am transgender. The first is when someone thinks I had a choice and the second is the entire process was at all easy. 

Since I was never a so-called natural feminine person to begin with, I needed to struggle completely to reach my goals of surviving in the public's eye at all as a woman...trans or not. The best description of my passing struggles came when my transgender friend Racquel told me I passed out of sheer will power. I knew what she was trying to say. I wasn't the best looking woman in the room but I was going to force the issue anyhow. 

Early on, I had only the mirror to do my gender battles with. I finally learned too late the mirror often lied to me. Night after night, I would think I looked great only to be immediately stared at or even laughed at in public. It was difficult learning how to try to dress myself so my feminine fashion helped me to live a life I had only dreamed of, not hurt it. At the same time, I tried to lose as much weight as I could and take care of my skin so I could wear less foundation. None of it was easy. But it was worth it.

In order to accomplish all I wanted to do on my difficult gender journey, I needed to learn something new and different. I had to learn to be my own best friend. I never liked my old male self and was just learning all the new possibilities of my feminine inner soul. She had many problems to face as she fought for acceptance from my male self who fought completely for all of his rights. At times, it was an ugly, bloody battle I never want to go through again. It was anything but easy and never a choice to go through as I was to find out later. 

I ended up suffering so much, I almost ended my life several times from various reckless self harm attempts all the way to an attempted death by pills which failed before I decided enough was enough. In order to survive I had to make a choice, so yes I guess I did have a choice and it was a very desperate one. Self survival meant I needed to pursue what measures I could and change my life forever. The final determination was deep down I felt more natural as a transgender woman and needed to find out where I would need to end up in the new pack of women in society. It was then I learned how deeply layered a woman's life could be and perhaps even more so as a trans woman. I had all the extra baggage of my previous life as a man which I carried with me to the other gender side. I knew the male gender expectations men had of women which made me extra shy of the entire gender dance between men and women. Primarily I learned why both genders often have a difficult time communicating in their relationships and wished often I could go back and do my life different. Maybe then, my second wife would have never said I made a terrible woman. Which I did and thought it only had to do with how I looked.

The final example for this post I will use was the amount of time it took me to finally face reality and come out fully as a transgender woman. Adding up the years, I struggled with my ultimate gender issues for nearly a half century. It was certainly difficult to break out of my old male chains and live the life of my dreams. I realized I never had a choice.

Men are From Where?

 As we attempt to cross the gender border from one side to the other, we certainly suffer from a lack of much training at all.  We had no understanding of which planet we trans folk came from to begin with. 

Partially because most of us didn't have the benefit of having an understanding mother or sister who participated in our progression into the feminine world. We never were able to indulge in girls only sleepovers where clothes, makeup and other girls activities were discussed and acted upon. Thus, when we actually began to have the chance to live in the world we always dreamed of, we had no idea of how to do it. The only ideas we had were from the outside looking in. 

The whole void we stepped into all of a sudden left us (as novice transgender or cross dresser persons) in a spot which was difficult to conquer. Many of us, including me, went through my feminine teen years which I never experienced in the public's eye. When I did stuff my overweight male body into tight female clothes designed for teen agers, many times I was laughed at when I attempted to go out in public. I found out the hard way my mirror only told me what I wanted to see and the mirror only reflected what my old male self thought was appropriate to present well in public. I was very stubborn in my approach so it took me awhile to realize to survive as a transgender woman in the world, I needed to be able to communicate with all other women. As I did it, I keenly felt the problem I had having no previous training growing up as a girl. Naturally, all the time and effort I put into surviving in a male world were a waste of time.

Perhaps, the biggest hurdle I faced when I transitioned from male to female came when I tried to communicate with other women. Quickly I learned the value of non verbal communication. Which is one of the reasons men and women sometimes misunderstand each other. Ironically, it was much later in my transition when I was finally was invited behind the gender curtain to truly experience how women communicate. I was warned by my wife one time when we had a fight, she told me I made a terrible woman and it had nothing to do with just appearing as one. So I set out to learn what she meant.

It took awhile but lessons were learned. An example was when I knew I had arrived as a trans woman when I was approached by a man in a venue. Instead of looking at him, I looked at the bartender (woman) who was looking back at me in essence to leave the guy alone. It was the first of many communication lessons I learned when it came for me to communicate with other women.

Other painful lessons came when I was involved with other women who I thought accepted me. They smiled and were overall nice to me until when I turned around and they had their claws in my back. Learning the new world of passive aggressiveness would prove to be difficult for me to adjust to. Of course I was used to the more forward aggression men deal with when engaging each other. I had no training in any of this public interaction as a transgender woman so I had so much to learn. 

Perhaps you remember the book "Men are from Mars-Women are from Venus". In my gender explorations I found the book to be true on many levels. Starting with and including communication. As a trans woman, I brought a totally different outlook to the binary gender standoff. I was flattered when women friends of mine asked me to explain what their men were thinking. 

At that point I wondered if the binary genders had a planet, why didn't we transgender people because we occupy such an unique position. Many ancient societies used to recognize us as special. We need to find our way back there again. We just have to be trained to do it. 

Shopping 201

Image from Brett Jordan
on UnSplash

Over the years I did quite a bit of shopping in clothing stores and malls, mostly successfully.

It took a while but I finally learned much of my success had to do with the fact my money was more important than my gender to the average store clerk. Many I think worked on commission and anything they sold was added to their paycheck. Even still, the experience was valuable in building my confidence as a novice cross dresser in the days I was running from the idea I could be transgender. I was paying my way to people so they would be nice to me. Only one time did I run into any problems when an older clerk told me my skirt was too short. In response, I left and never returned since there were plenty of clothing stores to go to.

In a short period of time, I grew tired of the same old shopping I was doing and started to expand into stopping for lunch where I needed to interact one on one as a woman with servers. The entire process opened a whole new gender world to me and for the most part I was treated politely with respect. Overall the process took me to a whole different level of Shopping 101. I grew bored and was ready for a new course I called Shopping 201. 

The new course ended up providing me with endless possibilities to expand my horizons as a very serious cross dresser. At the time, I was searching for ways to do different things in the feminine world. One way to sneak around behind my wife's back was to start doing part of the grocery shopping. I would pick times I knew the grocery store we went to would not be busy and out I went. The women's fashion trends back in those days fit me well. I could wear one of my oversized soft sweaters along with a mini-skirt and flats and look like any other fashionable woman without going overboard. One morning in particular was memorable. 

On the day, I carefully shaved my legs and prepared my wig. After dressing and putting on a light amount of makeup I took off to the grocery when my wife was at work. I arrived at the store, grabbed a cart and proceeded to pick up a few needed items. Then I headed up to the register line to be checked out. This was back in the days before self checkout so there was only one way to go. At the register there was one older cashier and one kid bagging groceries. When he saw me, his eyes immediately went to my legs and when he noticed me watching him, he blushed and stammered something about helping with my groceries to the car. Never before and rarely since have I affected a male such as that. The cashier just gave me a knowing smile. 

From there, I couldn't resist reverting back to Shopping 101 and made a quick stop at a nearby big box store to pick up another pair of panty hose and shop for new makeup. By doing so, I was able to hide my expenditures along with what I spent at the grocery store. 

I was able to negotiate the morning as my feminine self and learn so many new things so I could graduate Shopping 201 and move on towards life in a transgender world.   

Doing the Right Thing

 

Image from this Thanksgiving 
and the Jessie Hart Archives

At the most successful restaurant management job I ever had in my life, the company's main training point was to do the right thing.

Early in my life, I felt dressing as a girl or woman in any way was not doing the right thing. I suffered tons of guilt as I embarked along what turned out to be a long winding gender road. At certain roadblocks I found I needed to do the right thing again and again. Early examples came along when I needed to learn to dress my age and begin to blend in with the world. Often, doing the right thing for my inner feminine self came during the times I was soundly rejected by the public and came home in tears.

Perhaps the next step came around when I needed I had to finally leave my love affair with my mirror and begin to let the public be my mirror. It turned out it was one of the best moves I had made to that point in my journey. The whole process forced me to communicate with the world as a novice transgender woman and prove to myself the path I was on was the right one and it was leading me past the idea I had entertained for years I was simply a weekend, part-time cross dresser. Mainly because I felt so natural when I was living as a trans woman. 

Undoubtedly, I was doing the right thing with my life but there were so many challenges ahead. The more gender doors which opened, the more doors were still closed to me. A prime example was until I totally committed to living as a woman, I couldn't secure my permission to go behind closed gender doors and play in the girls sandbox.

Finally I arrived at the point where I needed to decide if I would subject myself to life changing hormone replacement therapy. After much soul searching and securing a doctor's approval, I decided to stay on the femininization road I was on and keep going. By doing so I knew I would be giving up what was left of my old male life. All male privileges I fought so hard for were gone and I was still searching for any female privileges which were still to come. The important point is I was still exploring my gender world to make sure I was still doing the right thing. After all, it was a major move. 

Perhaps the final chapter of if I really did the right thing won't happen until my final chapters are written, How will I be treated if or when I have to be admitted to an assisted living  situation. And finally will I be mis-gendered when I pass away. My only younger brother as already said he will never refer to me as my new legal name so that is that. 

In anyone's' life, doing the right thing is often the most difficult road a person can take. Especially when your life involves being transgender.

Increased Anxieties

Image from Sydney Sims
on UnSplash

When I reached the point where I considered coming out of my gender shell and pursuing a life as a transgender woman, my anxieties went up considerably. 

Possibly, the main issue was just surviving in a new world. Everything was different than I supposed it would be when I experimented as a cross dresser or transvestite. The main difference was I was attempted to insert myself into a new world without the benefit of my old male privilege's I had worked so hard to acquire. When my status was in doubt, I couldn't just bluster my way through and had to finesse it. Especially when I found myself in conversations with other men. When my car broke down one day, I found out the hard way how dramatic the gender change could be when the sheriff who responded along with the tow truck driver refused to listen to me regarding how the best way it would be to get the car back to my house. I finally had to just shut up and play the dumb blond. Even to the point of asking ridiculous questions about how the wrecker worked to the driver when we were heading back. 

Looking back, perhaps the only thing which was really hurt was my male ego who all of a sudden was shut out of my life. 

Through it all, my anxiety continued to build along with the pressure. As it increased for me to be successful on the stops I made on my new gender journey. By stops, I mean  the times I tried to slow down my male to female gender transition to reflect on all that I had learned. It was difficult because I was so eager to attain the next step I was seeking. I shouldn't have worried because huge changes were looming ahead which would make me terrified to go forward yet so excited not to. As the cis woman (born female) friends I began to know, told me so knowingly, welcome to their world.  Any time for reflection I had earned had to be learned on the fly.

As I added layer upon layer of experiences when I went public, adding communication was the one I write about the most. Learning how women uniquely communicate among  themselves was a challenge. I discovered women use a whole different form of talking when men are around or not around. Also, non verbal cues became more important to me as I found myself without the old male privilege of safety. As a man, I could take my personal safety for granted, as a woman the opposite was true. In fact, on several occasions pure eye contact with other women kept me out of possible trouble with men. It certainly took me awhile to learn the new nuances of communicating in the world as a transgender woman. 

The other issue which caused me extreme anxiety was the decision to begin HRT or hormone replacement therapy. I knew before I even considered starting the medications, I would need approval from a doctor which wasn't a given due to my age since I was in my sixties at the time. Plus, if that wasn't bad enough, I knew the changes I would go through would make it impossible to ever go back in my world to my my old male self. Since I was already diagnosed with high anxiety and was on bi-polar meds, this did not make my life any easier at the beginning.

Once I started the hormones though, I knew I had done the right thing. I calmed right down, developed in all the right places and went all out to establish a new life. In addition, as I started to feel at home adjusting to female privilege's, I earned my right to play in what I called the girl's sandbox.  

These days of course I still have anxieties and worry too much but I can say none of my problems come from my solved gender issues. A welcome relief.

Insistence

 

Image from the Jessie
Hart Archives

I found out long ago, living my desired lifestyle as my authentic feminine self would involve tons of insistence. 

First of all, I needed to insist I needed all the practice I could come by in front of the mirror as I attempted to perfect any sort of a new gender appearance. It meant sneaking around the prying eyes of an inquisitive younger brother as well as hiding from my parents who I knew would never understand. Slowly but surely my insistence paid off and I improved my appearance. Little did I know, it was only the beginning of an extremely long life time journey.

Through it all, I needed to insist on continuing my journey no matter how difficult the process was. If I was ever discovered, the push back would have the potential to be tremendous. I could lose my friends, family and job, almost immediately. As the pressure mounted, I still needed to move forward down my path to move from a part time transvestite or cross dresser all the way to living fulltime as a fulltime transgender woman. 

Insistence was also the key during my early days of exploring the world as my true self. I needed to face all the stares (and even laughs) I was getting from the public. I ended up learning the hard way how the mirror could and was lying to me. I needed to repeatedly go back to my wardrobe and makeup drawing board until I achieved more of a success. 

Then, I learned the hard way, how my successes would lead to needing more insistence for success on my part. I was petrified the first several times I was forced into one on one conversations with other women. How was my voice going to sound and what would I say were my primary worries. At the beginning, I resorted to trying to attempting to mimic the pitch of the woman I was talking to and as far as what I would say, I would simply just respond to whatever questions were asked of me. I don't know how well it worked but it was all I had. Finally I was forced to improve and began to develop who I would be as a transgender woman as I began to interact with the world.

Even still, whatever was going on, I needed to insist with some people I was feminine, not masculine. To this day, I have to correct the pronoun usage used with me by strangers. I am fortunate because I have two powerful gender allies with my wife Liz and my daughter Andrea (who also has a transgender child). Often either of them will lead the conversation for me calling me "she".  That way strangers who may question my gender have an idea of who I am. 

What makes everything so difficult these days are the continuing attacks on the LGBTQ and primarily transgender community by a certain political party not called Democratic. In fact, the party has outlined a platform for 2025 which would be the beginning of the end for trans women and men everywhere in this country. A prime reason all of us have to unite against the gender bigots now and in the future.

One of the positives is our tribe has been trained to be insistent and will survive in the future.

Planning Ahead

Image from Mohamed Nohassi
on UnSplash 

At some point in my transgender MtF transition I was forced to plan ahead.

The point I am referring to is when I came to the point I knew I was going to attempt to go "all the way". When I did, I needed to seriously consider first of all how I was going to be able to support myself. I worked at a job which was very male dominated and relied on serving the public, so I knew my company would resist my gender changes. Plus I couldn't even imagine how a kitchen crew would react to a transgender manager. 

I ended up taking the easy way out and was able to retire early on my Social Security benefits and augment them by selling the houseful of antiques and collectibles my wife and I had obtained over the years. Between the two, I managed to support myself as a novice transgender woman. Perhaps what I didn't plan so well for was the experience of actually living as a trans woman. Once I threw away or donated all of my male clothes, acquiring an everyday women's wardrobe proved challenging. I learned very quickly I couldn't be the "pretty pretty princess" I was for most of my transvestite or cross dressing years on a daily basis. I needed to fall in line with the women around me and dress for comfort when they went about their normal life's. Blending became my word of the day when I faced the reality of dressing feminine on a daily basis.

Once I conquered dressing the part, I then needed to adjust to going to places I may  have felt uncomfortable in as a transgender woman. Examples included places such as auto parts stores all the way to junk yards when Liz and I searched for a hard to find part for our old car. Through it all, I tried to keep my head up and deal with situations (which for the most part) never came up. What I didn't realize was  dealing with other women on a daily basis would prove to be the most challenging experience for me. All of a sudden, I was forced into deeper communication other than I love your ear-rings. Specifically from women who wanted to pry into who they were communicating with. Some were gentle and calculating while others were more blunt and to the point. Similar to how a man would attack. The most important point was I learned quickly how to  protect myself when I began to be out on a daily basis as a transgender woman.

I learned all the planning in the world all of a sudden didn't do me any good. I was making good on a lifetime gender dream and there was no turning back. I just can't say enough how big the changes were when I finally had the courage to go full time. I will never forget the experience and how fulfilling it was for me. 

Gender in Layers

Image from Monika Kozub
o UnSplash

Quite early in life I thought being feminine was just looking like a girl/woman.

It wasn't until much later on, I discovered how wrong I was. Even though I was an avid follower of everything feminine I could find, it seemed everything I did wasn't good enough. Everywhere I turned cis-women gate keepers were keeping me out. As I did manage small steps on my gender journey I came to a point where I collided with my second wife. All along she was very outspoken in that she didn't want to live with another woman. Especially if the woman was me. So I counted her out when it came to me acquiring any new feedback from her. I was completely on my own.

Since I was on my own, I did make mistakes and sadly my biggest gender strides came after she unexpectedly passed away from a massive heart attack. It was then I was free to explore my feminine self in the world. Very quickly I learned my deceased wife was right, I had a long way to go. I needed to advance from she called the "pretty, pretty princess" stage of my life, gather myself and attempt to move forward into a world I found I knew very little about. If I was going to advance, I needed to interact one on one with the world as a transgender woman.

I started with looking at the different layers of life a woman faces which were different from a man. Of course the easy ones were family driven. Since women birth the children, often the kids were more central to their lives. No big surprise. I didn't have much problem when I communicated the fact I was a parent too when I was communicating with another woman. It was from there when the communication became a little more difficult. I was petrified the next question would be why was I dressing like a woman anyway. That question never came and often we moved on to less important topics such as jewelry, hair and clothes.

About the time I thought communicating with other women wasn't so difficult someone would come along with a passive aggressive thought which would send me back to the communication drawing board. Men were so forward when they communicated in my male world, I got burnt several times when I didn't adjust fast enough to the women's way of speaking. What was she really trying to say. Was I truly pretty or just pretty for a man cross dressed  as a woman. Finally I decided to leave all the paranoia about communication behind. Instead of what could go wrong, I adopted what could go right as my inner slogan.

Other layers in my new life as a transgender woman came along mainly after I began hormone replacement therapy. Fairly quickly my emotions were released as the world around me became softer, My sense of smell even became more intense. The entire HRT experience helped to add layers to a life which was increasingly becoming more feminine. 

Through it all, delving into the deeper layers of a woman's life helped to make mine so much more meaningful.   

A World Class Observer

 

Image from the Jessie 
Hart Collection

For years and years I needed to be satisfied with merely observing the women around me hoping to see clues on how the women dressed and interacted in the world, among other things. All along, I thought I was doing the best I could in my observation  techniques without coming off as creepy. 

All along, I was doing all the easy things right. I noticed fashion trends and also observed which women seemed to have conquered the fashion world correctly. Some of whom managed to take fashion to an art form. As hard as I tried, I was unable to go any farther than being a more than casual observer of everything feminine. I was always stopped at the door by gate keepers who wouldn't let me into the inner sanctum of what being a woman was really about. While I was stuck on the outside looking in, I needed to sit back and concentrate the best I could on clothing and makeup. So at least I was doing something positive. Or so I felt. 

As the years went by, I worked hard to perfect my feminine image. My peak of acceptance was the night I was refused admission to a transvestite mixer in New York because I was a "real" woman. The experience was all well and good until my second wife and I became embroiled in a huge fight about it. To make a long story short my still strong male ego got the best of me in a fight and I told my wife what had happened. At that point she told me I made a terrible woman. I was deeply defeated at that point when she backed off and said she wasn't talking about my appearance, she was talking about my inner knowledge of what a woman went through in life. From that point forward my life changed as I knew I needed to discover what she was talking about. 

The path I chose was very difficult and little did I know I would spend the next decade (at least) to learn what she meant. The biggest problem I found was I was automatically excluded from entering the inner workings of how women actually communicated and interacted with each other. Even though I worked in a woman dominated industry, the basics I learned such as the dominance of women in cliques and the passive aggressive nature of such cliques was new to me. In fact, it wasn't until after I began to transition in earnest into being a full fledged transgender woman did I understand totally the basics of how women communicated without men. Quickly I learned how feminine conversations could be built on silence with just a look of the eye. I needed to toss aside the old male patterns such as full frontal attacks when life came to confrontations and aggression. 

Naturally the more time I spent in the world as a transgender woman, the more I became a world class observer of cis women everywhere. In order to survive and make myself into a better person, I needed to step aside from all my old male ways and accept the direction my dominant inner feminine self was taking me. After all, she had spent years waiting for her chance to shine. As I always write about , I was fortunate to have strong cis-woman friends and role models to help me along. They embraced me when so many others wouldn't. My observation techniques with them most certainly became world class because they allowed them to happen. I finally was learning what my wife told me concerning making a terrible woman. I found out the hard way what a terrible woman was and made sure I didn't make that mistake again.   

Trans Boomers

 

Without really trying to do so, I believe the blog has settled into having an older clientele, so to speak. Very rarely do I receive a comment from a younger transgender person or even a parent of a trans youth desiring to transition. By far the number of comments I receive come from other trans women of age. Meaning my age. I also have feedback from many other transgender veterans. Where ever the feedback comes from , I completely appreciate it. Here is my latest comment from a reader who prefers to keep her name private:

"When I look back, as I often do these days, I often feel that sense of regret for things done and things left undone. But, then I try to remind myself that my life has been remarkably good in comparison with the billions of sentient apes that have ever lived and is arguably better than most of the billions of humans who presently inhabit this planet. I do wish I had transitioned earlier and more gracefully, but imagine how many never had the chance at all."

Thanks for the comment! I like the parts about your life being arguably better than others who never stepped out of their comfort zone to live their dreams. Plus having the ability to have transitioned earlier with more grace really struck a chord.

I find the main things I have in common with other readers, is what we went through when we started to question our gender to begin with. The main problem we all had was the lack of internet communication with our peers. I remember distinctly the days when I communicated with other transvestites by writing letters, remember those? I believe my first experience with another "friend" on line was on an old "AOL" dial up chat room. All was proceeding past my expectations until my wife caught me one day. Then my brief experiences in chat rooms came to a halt. Until I could find a more secure way to do it.  Those were dark and lonely days in my closet but I was still desperate to get out and sample a more feminine world. 

It wasn't until I discovered Virginia Prince and Transvestia magazine, did I finally have a way to see there were actually others who shared the same desires as me. I was very excited when I learned the "Tri Ess" cross dresser organization  (which was somehow connected with Prince and/or Transvestia had regular meetings in my native Ohio. The first transvestite mixers I ever went to were a three hour drive away in a location up near Cleveland. Even better than that, I learned other organizations were planning get togethers in Columbus, Ohio which was only an hour away. I can't remember for certain now how many of the mixers I needed to attend before I began to feel more comfortable. I mostly was so dazzled to be around other people with similar gender pursuits to mine, I just came to view and judge the proceedings. 

The first thing I discovered was how layered the group really was. It seemed everybody quickly formed their own little cliques. Almost everything on the female stereotypical spectrum it seemed was there. And perhaps most dramatically, the rule that everyone had to be a heterosexual man was quickly thrown out the window. Too many people were disappearing behind closed motel doors to be totally innocent. Then there were the "mean girls" or the attendees who were often impossibly more feminine than the rest of the crowd and knew it.  I so wanted to look as good as them but without the attitude. The best part about knowing the mean girls was being able to go out with them and party after the mixer was supposedly over. That's where the true feminine action took place. Usually, a group went out to a large gay dance venue in downtown Columbus. Just being able to tag along and watch everyone else was my favorite part of the evening. Mainly because I was finally having the chance to live out my dream of living femininely. I felt I could never look as good as the mean girls but I could still enjoy myself.

Today I feel much has changed for the younger transgender population and that is mostly the reason for the "boomer" niche I find the blog to be in. These days (in at least many larger metropolitan areas) there are special LGBTQ organizations to reach out to. I can't imagine though the extra fear and even panic a younger person has these days when they consider coming out as transgender. I guess it proves no one gets a break, young or old, when it comes to being trans. 

I just wish as a trans boomer I could have helped provide a clearer and safer path for the younger generation today.  

Benefits of Crossing the Transgender Divide

Quite often it seems our journey across the gender divide is perceived  as only being a negative experience. Equally as often, our early coming out experiences add to our overall thoughts about breaking out of our dark gender closets. Every time we are completely rejected by the public, it reinforces the negative ideas we may have had which led to the many purges we went through of all of our feminine possessions. 

Jessie Hart in the Ohio State
Student Union

Still we endured as we walked down a lonely path to gender discovery. So much frustration and even tears led us to risk much if not all of our lives. For the fortunate ones, we were blessed with enough gender euphoria to move forward. For each time we were rejected and belittled for showing off our feminine selves, there was another time we were embraced by someone else in the public's eye. The best part was, gender euphoria felt so natural. So much so if I could sing, I would have since I felt that good. 

Looking back, I think the first time I felt the benefits of spending time on both sides of the binary gender fence was when cis women began to ask me for advice on how to understand their husbands, Even though I did my best to help them, I still had to explain (regardless what they thought) most all men were not all alike. The majority of their problems came from communication. It wasn't so much that men didn't listen, it was more as if the men just didn't comprehend what women were saying. An important part of my learning process came when I realized women did communicate vastly different than men. I learned the hard way to look for non verbal cues when talking with another woman.  Before I was allowed to play in the woman's sandbox I suffered many claw marks and back wounds before I learned how to play. 

All in all, my gender wounds were worth it because once I gained access to the sandbox, I didn't ever want to go back. I see the process now as a real benefit in my life. How many other humans can say they experienced such a deep process as living a life experiencing both sides of the gender divide. A recent experience which could have caused me to be mis-gendered at the VA may have been caused by how I answered a question by one of the nurses. She asked me who my driver was after my colonoscopy . I said my wife when maybe a better term to use would have been partner or spouse. I am a believer in how the smallest details can help me get along in the world. 

Even though I had to give up so much of a male life I never really wanted, the work of learning the feminine gender was a work of pleasure because mainly I felt so natural. The topic for an entire other blog post. 

Now I am happy to say I have made it to a place of gender understanding. However, I think I am far from knowing it all. I don't think I will ever know why I was chosen for this gender journey. Hopefully when I pass on, I will find out the answer. 

Toxic Masculinity and the Trans Girl

Over the years when I was trying my best to exist in an ultra masculine world, I encountered too many men who would have been described as being toxic masculine. In essence they were the ones who tended to dismiss women as basically only emotional people who were only good for sex and/or having kids. 

I can truthfully say I wasn't an active part of their mentality but on the other hand was ashamed when I went along with their childish actions. I had two excuses. The first was in the business I was in I had to manage to the best of my ability a group of macho redneck cooks in a kitchen. I had to appear tough. The second was on the other hand I had to manage a group of mainly female servers, hostesses and bar tenders. Even then I was studying women intensely to learn how they really maintained in society so in many ways it was a labor of love. I learned my guys in the kitchen worked better when I could manage them as a team and the women worked better when I understood they were going to form their cliques anyhow, so adapt to them and hope for the best.

Further more I had to watch for frontal confrontations from the men and passive attacks from the women. Lessons which would serve me well later as I transitioned genders.  

Lessons I wish I had paid attention to didn't take long to happen. One night very early in my transition I found myself with a group of men discussing a topic I considered myself to be well versed in. Very early they shut me totally out as if I was never there at all. I thought it was one of my first opportunities to learn first hand what my life was going to be like as a transgender woman. I was right and on the other hand, my lessons learned from my work world worked well too. 

I also learned quickly the amount of  non verbal communication women use. It is no wonder most men say they can't understand women when they can't pick up non verbal cues. 

Photo by Icons8 Team on Unsplash

Ironically I had to change my stereotype of what a toxic man even looked like. When I began to explore the world, I attempted to stay clear of any man who looked like the macho type. not unlike my former self. It got so bad I couldn't even try to buy tickets for a sports event from a street "scalper" because they thought I was a cop. Slowly but surely I learned many of the "macho" men didn't seem to care much about me at all and weren't going to verbally attack me. My theory was they were more secure in their sexuality than the normal man. 

Of course recent political activities have made it possible for toxic masculinity to come out of the shadows and even thrive in some areas. Unfortunately the trans community, women and men, has been potentially the hardest hit. The attacks aren't just coming from cis men, they are coming from cis women as well.    

The future is not a given for anybody. Especially not the trans girl.  As always we are going to have to be better and fight for what we have.