It's Complicated

Image from John Barkiple
on UnSplash.

 
In many ways, this post is an extension of yesterday's post.

In it, I attempted to write about the connection (or lack of it) between members of the transgender or cross-dressing communities. What continues to amaze me on many levels is how complicated the outside world does not see in our world. So many in the world still think all we have to do to "solve" our gender problems is as simple as not putting on a dress for transgender women, or a pair of pants for a transgender man. Granted, it is very difficult to explain what is going on in our own gender challenged minds. How could I explain my desires to others, when I could not explain it to myself. Back in those days, there were not even therapists available who had any knowledge in the gender field to provide any help.

In the meantime, I internalized all my feelings and dreams of being a transgender woman someday, much to the detriment of my own already fragile mental health. My problem was (among many) I was naive and did not realize how complicated my genders were. I had no workbook to study from. Being completely on my own, forced me into making many mistakes I did not foresee coming as I followed a curvy gender path. The only woman I sought guidance from, withheld any significant advice, basically because she just clashed with and did not like my inner feminine self which was trying to emerge. 

What I did then was move past my wife and discover what my new world as a transgender woman had in store for me. All of it was difficult in the worst way when my old male self-ganged up on me. Both of them were losing traction on claiming my world and resented it on so many levels. It stayed so complicated because I loved my wife deeply and we had built a twenty-five-year marriage often on the ashes of my gender conflicts. When I was down and out emotionally, my wife was the first to bear the brunt of my frustrations. I knew I was wrong, but there was nothing I could do to battle my overwhelmingly frequent desires to being a woman. In fact, when my second wife was still alive, I was very actively exploring the world as a transgender woman. Primarily to discover, if I could survive at all.

My explorations proved what I suspected all along. Women lived a very layered and complicated existence and being able to join in at mid-stride would not be easy. Similar to attempting to jump on a very fast moving merry go round without it slowing down. Once I found myself on the feminine ride, I was given a chance to really learn and absorb what a woman's life was all about as my brain was rewired to survive. What amazed me was how quickly I was welcomed into a woman's world as one of their own. The worst which happened to me was when I was gently laughed at by my new cisgendered women friends when they said, welcome to our world. Which I was overwhelmingly happy to be a part of.

Ironically, if I was prepared or not, I entered a world much more complicated than the gender conflicted world I left. Plus, what happened was, the more I grew into my new world of transgender womanhood, I grew away from my wife. Before she unexpectedly passed away, it became obvious our marriage was doomed to at the worst being a total split, to at the best living as two women on their own. One-way or another, fate decided the question for me.

In many ways, I wonder if I had ever imagined such a complicated journey through life was going to be in store for me. I guess at the least, I could say, life was never boring as I suffered from being the round peg being forced into the wrong square hole. My reward was being able to say I learned how both sides of the binary genders lived, and I could choose which one I wanted to live as.

I Just Couldn't Live Without Her

 

Image from Brian Kyed
on UnSplash.

At a certain moment in my life, I had reached the point of no return where I was living with two women, the one inside of me and my wife of twenty five years.

The question remains, how did I find myself in such an untenable, precarious situation. The answer was, it was not easy, and I really had to work hard to get there. Decades, to be exact. Once I pulled myself out of the mirror, and put her into the world, I knew I could never go back to being a parttime cross dresser. I could never live without her.

Many times, I have gone through the many steps I took on my path to transgender womanhood. To provide you all with a more precise look at my actions, we need to go back to the years when my second wife was still alive. What I began to do was sneak out of the house when she was working cross dressed in the world just to see if I could. After a very rough beginning, when I was laughed at, I began to get my high-heeled feet on the ground and do better. So much better, I began to think my ultimate goal of living as a transgender woman on my own terms may actually be possible. 

From there, I began to spend every spare moment I had alone as who was to become my authentic self. I became so immersed in becoming a woman, I needed to concentrate on the times when I still had to be a man at work, or with my wife. The biggest problem I had was, deep down inside I knew which gender route I had to take to survive in the world, but I was afraid to face it. The fights between my wife and I became so bad, a couple times she just told me to be man enough to be a woman. I was not man enough to do it, but I was stubborn enough to keep trying to live a middle of the road gender life, which became impossible to maintain. My mental health suffered, and I began to be more self-destructive than I already was. All the way to attempting suicide one night.

Fortunately, I was not successful in my suicide attempt, and I proceeded down the same path I had been on before. This time taking my cross-dressing activities into my own restaurant and threatening my substantially good job. Again, deep down I felt if everyone knew of my deep, dark secret, I would be relieved of the hell I was living because I had to make a change away from the male life I was living. 

Just before my wife suddenly died, I made one last ditch effort to partially purge myself of my femininizing supplies. I went all the way to growing a beard, so at least I was telling myself I was making an effort to return to the male world. However, there was one big problem, I was miserable and about the time I needed to go back into my feminine world, my wife suddenly and tragically passed away from a massive heart attack at work. Through all of our problems, I loved her deeply and we were married twenty-five years.

I often wonder what would have happened had she lived. I think now, my internal female would have won out and I would have completed my gender transition. She would have won because I felt so natural in the world as a transgender woman. When it came down to which woman I could not live with, I would have had to have chosen the woman I should have been all along and hopefully patched up my life with my second wife. So, at the least, we could have stayed friends.

Torn Between Two Lovers

 

JJ Hart in Key Largo

For too many years I care to remember, I was torn between two lovers.

The lovers I am referring to, were my second wife and my inner feminine self. The battle was often intense as both of them decided to take no survivors or prisoners.  Plus, the problem intensified when I became immersed in the feminine world and my second wife grew increasingly resentful about it. Which meant when and if I went to her for any assistance, I was rejected. In fact, on the rare nights when she had to come to me for makeup advice, I could tell it really hurt her to do it. 

I distinctly remember one night she agreed to go out to dinner with me cross dressed as my increasingly important self. I knew at the time, if I was to have any hope of acceptance from her, I would have to make my attempt to dress like her. Which meant I needed to pick out my best jeans and blouse for the date. I even went as far to be careful to tone down my makeup. Predictably, all of my efforts were not enough. She made it clear she did not like or wanted to do anything with me. It was the last "date" I can remember. 

The gender conflict caused many rifts and giant fights between us. When the fights happened, somehow, we were able to patch up our relationship. Often with the promise I would never go out of the house into the world again. Which led to a huge problem. Deep down, I knew there was no way I could keep my promise. Because, at the time, I was so into the scary, exciting new world I was exploring, there was no way I could go back. The problem was, I felt so natural as a transgender woman. 

It turned out, the emergence of my novice transgender self-began to make my wife and male self very uneasy. After all, their very existence was being threatened. 

The whole process tried to destroy me. It was often too much to take when the battle for myself reached an all-time high intensity. Certainly, being torn between two strong women was no fun and I would not wish it on my worst enemy. 

I did not know for years how strong my inner woman was. The years she had spent being hidden away had taken their toll. She became strong on her own by default. Sadly, the battle ended without a true winner when my second wife unexpectedly passed away due to a massive heart attack. By default, my stronger feminine self, pushed my weaker male self aside and took over. 

I had lived through an unique transgender situation. I was torn between two lovers, my wife of twenty five years and my developing inner feminine self who was busy telling me she had been along for the ride for my entire life. I suffered through it all and came out on the winning end. As I said, being torn between two lovers was no fun. 

I Was Led Kicking and Screaming

 

Summer Image. JJ Hart

One good question I receive a lot is why it took me so long to finally accept I was a transgender woman and move on. 

The answer is I was literally led kicking and screaming towards my gender dreams of accepting my feminine self. I know it seems like a contradiction in terms, but it is true. Looking back, there were two things I can attribute my problems to. The first one was my male self-put up a real fight every time his territory was encroached on. He always seemed to come up with good reasons why I should not consider going any farther into my increasingly natural feeling feminine world. When I was feeling more and more secure with my decision to live as a transgender woman, a good time as a male would come along and challenge my thought pattern. It was like he was saying, I told you so and I could continue living as a weekend or part-time crossdresser, more or less as a hobby. While other men my age golfed, I wore women's clothes in the secrecy of my house.

Deep down, I knew that would never be the final solution. I knew it from the first days I looked at myself in the mirror cross dressed knowing in a couple of days I would have to do it again because merely dressing in women's clothes just wasn't enough.

The second major problem I had was my twenty-five-year marriage to my second wife. Through all the ups and downs of living together that long, I dearly loved her. Plus, I am always careful to say she knew of my cross dressing before we became married and accepted it. It wasn't until I began to embrace the idea, I was transgender did she begin to put up serious resistance to her ever living with another woman which she equated me with if I started gender affirming hormones. The whole process led to the most shameful period of my life when I began to cheat on my wife, with myself. What I mean was, I would lie to my wife about where I would be and what I would be doing as a man when in truth, I was out testing the public as my new authentic self. I was led kicking and screaming into a new exciting world mainly because it felt so natural to me. 

For once in my life, I began to feel the possibility I could find happiness and just maybe my gender issues were the problem all along. When I reached that point, I ultimately knew deep down what decision I would have to make. It would be selfish of me to give up on our marriage just because I wanted to live as a woman. Ultimately, my decision was made for me when my wife unexpectedly died from a massive heart attack at the age of fifty. Following my tragedy, I decided my resistance to entering transgender womanhood was behind me and the time was now or never to accept my ultimate gender destiny. Start HRT and begin the process to give away all my male clothes, along with all vestiges of his old life.

From then on, my male self was finished.  I went on to find a whole new circle of friends who in turn taught me a deeper meaning of what it meant to be me. There was certainly no more kicking and screaming from my old male self as he had given up to the feminine master of my soul and universe. She had won the battle and never looked back. 

 

The Rock and the Hard Place

 

Image from
the JJ Hart
Archives

Recently, I received a comment from a reader who said in essence, I was too hard on my second wife when I mentioned her.

After thinking the comment over, I can see why it was made. First, some quick history. My second wife and I were married for nearly twenty five years until her sudden and untimely death at the age of fifty. She knew I was a transvestite or cross dresser when we were married and accepted it up to a point. The demarcation line was always HRT or me pursuing  a life as a transgender woman. For years it was fine with me as she approved me going to a motel to cross dress and go out into the world. We had an uneasy gender truce and I ended up abusing it.

The problem was, I always blamed myself for our gender problems because naturally, they all originated with me. Primarily when I began to break the promise I made to never leave the house dressed as my feminine self. Of course, I eventually was caught and all hell broke lose. She was a strong woman and knew how to emotionally battle me. She was the rock keeping me from my increasingly obtainable goal of trans-womanhood and I was in the hard place of knowing deep down it was where my life was headed.

Along the way, my second wife imparted good information about being a woman but withheld other very important facts. She would just tell me I made a terrible woman and then adding in she was not implying anything about my appearance. Leaving me to wonder for years what she meant. Mainly I found my old male ego was still in the way of my gender progress to the future. It wasn't until she had passed on and I took the opportunity to really explore the world as a transgender woman, did I understand what she meant. I finally had to walk the walk and talk the talk to move my hard place along. Femininization was difficult yet exciting for me on many occasions.

My second wife also tried to tell me to follow my dreams and give up our relationship but I still tried to have it both ways which just made things worse. She knew me better than I knew myself. 

So, as you can tell, I owe her quite a bit and wonder if we could have at least arrive to a point where we could have been woman friends. I obviously don't say it enough if I am receiving comments to the contrary. I also don't praise the cis-women who stay in marriages with their transgender spouses. I know if the shoe was on the other foot, I would have an incredibly difficult time accepting a trans spouse. As my wife said, living with another woman  was something she never signed up for. 

The rock and the hard place cost me dearly over the years. The pressure of attempting to maintain a relationship and a male life with the increasing knowledge it was all a lie built up an enormous amount of pressure and all but ruined my fragile mental health. I resorted to trying to drink away my problems to no avail and just became more depressed. I was not freed until I basically had nothing else to lose after her death. Once I was freed, I could look back on our relationship for what it was and all the good times we had and how I basically hurt it all.

Transgender Cheating

Image from Club Diversity 
Columbus, Ohio.

 I can safely say, I never cheated with another person during my twenty five year marriage to my second wife.

Before I put myself up on some unneeded pedestal, I have to temper my statement of cheating with saying I only cheated on my wife with one person, who was me. Why I say it is because the more I grew as a transgender woman, the more I grew apart from my wife. When I did, I started increasingly to leave the house as my feminine self to see if I could make it in the world. 

Of course, I did and when I was successful, I wanted more and more and I simply could not turn back into my male world. The more I celebrated my new world, it was done completely away from my wife. Which was a shame. I also define cheating as me going against the basic agreement we made which said I would never leave the house cross dressed as a woman. In fairness to her, she bent over backwards to make it happen. Even to the point of letting me go to a motel a couple times a week, so I could safely cross dress and explore the world. 

Even the motel agreement was not good enough for me. Very soon going out anytime my wife was working became the norm for me. My life suddenly became exciting and way too natural for me to ever return. 

The closest I ever came to really cheating came was with an encounter one night with a lesbian in a venue I was a regular in. She bought me a beer and told me she should take me home with her, which was flattering but scary since I needed to beat my wife home from work. There were a few other times my flirting almost got me into trouble mainly with other women but I never went forward with any personal contact.

Since my wife passed away very unexpectedly at the age of fifty from a massive heart attack, my vow never to cheat remained secure. Even my male self managed to never pursue any of the impossibly attractive servers he hired in his restaurants he ran. I was very proud of all of it but never was I proud of needing to lie and try to tell my wife to her face I was not going out on her with another woman. Which happened to be me. If I would have been truthful with both of us, I would left my male self behind long ago and set out to live a feminine one as a transgender woman. I was selfish and wanted to try to preserve what I had earned as a guy. The upside came when my girl self had been put into a brief submission and I enjoyed my time with my life more deeply. The downside came when the friction between my gender issues made my life nearly unbearable. 

I guess, deep down I knew my wife was ill and for the six months before she passed, I grew a beard and purged some of my feminine wardrobe. The final six were some of the most miserable I had ever faced but little did I know, it was going to get much worse before it was going to get better. Basically, through death and loss, the only strong influence on my life I had left came from my feminine self. She wrapped me in her soft arms and let me know everything was going to be alright. Her influence and my overall belief in what was right, tiding me over until my current wife Liz came into my life and reaffirmed my idea I was stubborn enough to live through my issues. Liz told me all she had ever seen in me was female and it was all it took for me to go wholeheartedly into doing away with my male self. 

I will forever be proud of the time I spent being faithful as my male self to my second wife and, on the other hand, be totally ashamed of myself of how my feminine self handled her life with my wife. Non unlike two strong women locked in a struggle. 

My excuse is I was learning my new life as a transgender woman and until I fully understood it, I was petrified of moving along.

   

Stuck on Me

 

Image from Monika Kozub'
on UnSplash

My second wife used to be fond of telling me, my gender issues were all about me.

Looking back, I think she was right. In so many ways I was single handily attempting to cross the gender frontier with no help from anyone else, including hers. Among many other things, she just did not care for my inner feminine self. She always called me the "pretty, pretty princess." Even though the comment always hurt my feelings, I knew I was too immersed in my appearance and then lacked the actual experiences in the life of a woman to prove her wrong. Plus, I was selfish in my pursuit of a better feminine cross dressed experience. Not to say very frustrated when I was only getting out into the world very infrequently to explore and learn to explore what she was talking about. Just going out on Halloween and very infrequent transvestite mixers was not enough to relieve my gender tension or dysphoria. 

Since she passed several years ago, I will never know for sure but I think she never did want me to survive as a transgender woman and return to my full-time male self. I know I came off as being selfish and I was. I couldn't wait for the next time I could cross dress as my authentic self who at the time was really learning how an intense a time it was going to be. It was an incredible time in my life of learning and I was extremely disappointed my wife could not or would not come along. On the other hand I understood when she told me she never signed up to live with another woman, which I could not disagree with. I was stuck between my transgender rock and the hard place many trans people find themselves in. Either discontinue my gender journey I was on to become a transgender woman or at the same time I give up on my twenty five year marriage.  To a woman I loved very much. 

Along the way, I learned I was so much more than the "pretty, pretty princess." I am sure if my wife had lived, sooner or later I would have had to follow my true gender path and we would have needed to separate. My fondest desire is we still could have remained friends and she would have liked the new feminine person I became. After I paid my dues.  As it was, when she passed so unexpectedly, she left me on my own. Which meant relying on the gender basics I had come to trust over the years. It was then, there was nothing holding me back to going forward towards a gender transition. Even as stubborn as my male self was, he finally gave up the effort to maintain his place in the world.

So once again I was stuck on me and this time, it was the true me. The me I always dreamed of becoming with the help of my wife Liz and other lesbian women friends I had made. When I gave of myself, they gave it back to me. So, in many ways, I was stuck on them. There was no more princess in my future. I had paid my dues and applied to play in the girls' sandbox. Even though there were plenty of times I had sand thrown at me or suffered claw marks, I survived and earned my right to be there. At my age (sixty-ish), I thought I was too old to start over again but found out I was not. 

Through the miracle of gender affirming hormones and life experiences, I was able to reboot my life and live a dream I never thought possible. I guess you could say I became stuck on life. The princess was gone and she was replaced by a secure public transgender woman. Buh-bye!

Un-Common Risks as a Trans Girl

Liz on left. Date Night. 

Most people undertake a risk or two as they make their way to the undertaker in the end. 

When you come right down to it, which person you chose to marry is a risk as well as which profession you choose. Transgender women and trans men seem to have an added layer of risk in their lives. Along the way as we pursue a gender transition, we have to make many difficult choices which aren't really choices at all. They are paths we have to follow or face devastating self harm to ourselves. Which results in extremely high suicide rates in the transgender community. 

When we are growing up in a world where our families often don't accept us, the entire process makes the risk factor even more important. I am so blessed to have a daughter who completely accepts and supports her transgender child and I am proud to have been a role model for my grandchild to follow but it wasn't easy. 

When it came to my marriages, seemingly destiny has led the way into several different areas of acceptance. Acceptance of course led to risks being taken. My first wife was very easy going and knew of my cross dressing desires before we were married and had our daughter who turned out to be my only child. My first wife accepted without question my desire to cross dress as a woman and venture out on Halloween adventures. I often thought if I came home from work one day and told her I was checking into a hospital for gender alignment surgery, she would have said that's fine, just be careful. As it turned out, I was not ready for that sort of surgical risk and would never be.

Then destiny threw me a curve ball with my second wife. The moment I saw her for the first time, I knew I wanted to be with her in the worst way. Even though she too knew I was a cross dresser, she still restored feelings I long ago had forgotten when I was ready to compete with another man for a woman. In order to win the competition I needed to divorce my first wife and move on to a totally different strong woman who knew somewhat of my gender issues. I say somewhat because back in those days I was just learning myself how deep my transgender feelings ran which were to cause strong problems in our twenty five year marriage later on after the newness wore off. From the start, I always thought she would be the one who would help me to break through in my cross dressing world and help me to be successful in my dreams. As it turned out, she wasn't that person and always drew the line if I suggested at all I wanted to go further into the transgender world. By the time she had passed away, our relationship had deteriorated into an ugly cat and mouse game of me taking risks and seeing what I could get away with.

Another main risk I took was with my job. Slowly but surely I had been promoted through the managerial ranks to a successful position as an executive general manager of a big popular casual restaurant chain. A position with a company I knew would not accept me transitioning into a transgender woman. In my haste to destroy myself anyhow, I began to go to my competition as a woman thinking no one would recognize me. Well, I was wrong and the roof began to fall in on me. It was tough but I denied all the rumors and kept on going.

By this time, my second wife's life was coming to an end and she suddenly without warning passed away from a massive heart attack. By this time I had purchased my own restaurant and was somewhat in control of my own financial destiny until a recession in the Rust Belt where I lived wiped out the population. I ended up losing my restaurant as well as my inheritance by taking a major risk and losing nearly everything I had. I finally was able to find me a fast food job to hold me over till I could take an early retirement from Social Security and sell vintage items my wife and I had collected over the years. Between the two I survived.

I then found myself in a period of wonderful gender discovery, when with the help of new women friends everyday seemed as if I was reborn. Specifically Kim and Liz helped me the most. Liz lived in nearby Cincinnati and we met on line. After corresponding by email  for months, I finally became brave enough to talk to her in person and our first date was at a drag show. That date was nearly twelve years ago and we are coming up on our second anniversary of marriage. Liz cemented her place with me when she told me she had never seen a man in me and why didn't I finish my transition into a feminine world with her.

Finally, after a half century of wondering and suffering over my gender dysphoria, someone else recognized my truth and wanted to accept it with me. My un-common risks were over. I accepted her advice, gave away my male clothes and never looked back.

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.  

Gender Truth

 

Ripley, Ohio Image from
the Jessie Hart Archives

Following years of living a huge lie, I decided to live my gender truth. All along, I should have never been a male and felt so natural and alive when I was being feminine. 

As with any lie, you need to be more and more skillful to keep the ball rolling and not be discovered. The process all started when I was a kid and was carefully hiding away my small collection of girls clothes and makeup. Some of the items, I "borrowed" from my Mom when she discarded them and others I was able to purchase myself with funds I earned doing odd jobs around the house and from my newspaper route. I will never forget the first trips I had made to stores in nearby downtown Springfield, Ohio to buy makeup. I was scared to death since my Dad worked close by and I thought for some reason he might catch me there. Even though, it was my money and I was spending it the way I saw fit, I still felt guilty. The truth of my life still escaped me as I did my best to live in the male world. 

Somehow I was able to hide away all my clothes and makeup and even managed to shave away the hated hair which appeared on my legs when I became a little older. Probably, I was shaving my legs earlier than some of the girls I knew with strict Mom's who wouldn't even allow them to use lipstick. Looking back, I am sure I would have had the same problems with my Mom had I been born female. I just know she would have tried to restrain me the same way she did when I was her oldest son. All she really accomplished was enabling me to be more skillful in hiding my truth. I think. At the least, nothing was ever said to me by either of my parents.

As I cross dressed my way through college and my post military days, hiding my gender truth became increasingly more difficult. Primarily because I was slowly doing more and more in the public's eye as I left my closet to explore the world. The new truth I needed to face was how or if I was going to tell potential spouses who crept into my life. Even then, it seemed to be extremely unfair to both of us to not come clean from the very beginning. Except for my first fiancé, none of my future wives held my gender truth against me. Primarily because of a Halloween party, my first wife attended also, she was around when I confessed to a very small group of friends my costume was more than a casual fling to dress as a woman. As the years progressed and I became more assured of my gender truth, I decided I needed to tell my second wife also before we became married.

The problem became with my second wife was when I though I was telling her my gender truth about being a cross dresser, I wasn't. All along I was lying to myself and I was really transgender, not a cross dresser. Which was always a major problem for my second wife. She didn't care about the cross dressing but drew her line in the gender sand when it came to any idea or discussion of beginning any gender affirming hormones. Which, had she lived, would have probably ended our relationship.

Years later, at the age of sixty, I thought I was done with anymore serious relationships and wives is when several other friends came along, including my current wife Liz. With them, I basically had the opportunity to go full circle with my gender truth. Specifically, with Liz who told me at the time, why didn't I just leave the rest of my male life behind because she didn't see any man in me at all. 

Her push was all I needed to throw out what was left of my male clothes and concentrate on living my gender truth. The only problem I had with how it all worked out is why I waited so long to see it and live my gender truth. 

Who Do You Love?

Image from Freestocks 
on UnSplash

Along my lengthy transgender journey I learned the hard way I had several love affairs. 

The main one I want to refer to is the love affair with my wife and  the one with myself. Or should I say my feminine self, since I had never really liked my old male side I never asked for. I think the worst part of having two love affairs was the guilt which came with it. I think my major problem came from how much I threw myself into the process of being feminine. If I wasn't cross dressing in front of the mirror, I was spending my time studying all the girls or women around me. I am sure along the way, my wife caught me daydreaming too much and wondered why I was not paying more attention to her and our marriage.

Along with the daydreams came the frustration I felt when my wife was able to do all the things a woman does in her life. Plus, she wouldn't let me in to her world very much and she infuriated me when she wouldn't. The entire process led me to try even harder to improve my makeup and fashion ideas since at that time I was far away from realizing looking like a woman was only the very beginning of my long gender journey. At the time also, since I was putting so much time into myself, I am sure my wife felt unloved and I am surprised we made it through twenty five years of marriage. 

Much later, after she passed away, did I learn to love myself. I learned then the fact you needed to love yourself before you can love someone else was so true. Once I started to complete my transgender transition, I did start to love myself. Or, at the least, I started to have more respect for everything I had achieved in my new world I had chosen to live in.   

It was about that time I was feeling deep frustration because of the way my life was headed. Although I did enjoy the small social group of women I was apart of, I still felt I was doomed at the age of sixty to live my life alone. I found I was still a social creature and did the best I could to change the situation. Fortunately for me, my attempts at dating when I was still a guy were miserable short term failures which led me to believe I was on the right path to living as a trans woman...even if that meant living alone. As a stop gap measure, I still had my friends to hang out with.

For the most part, my experiences in the on-line dating world were failures too. I tried every combination on the sites I could afford to list on. One month I would try "man seeking man" as a transgender woman, then the next time try "woman seeking woman". Again always being up front I was transgender. The only men who responded for the most part wanted me to dress them up as a woman or let them wear my panties, so they were out. 

There was a happy ending to my on line dating woes after sifting through tons of rejections and trash, my wife Liz responded to one of my ads. She lived fairly close to me in a city I had always loved (Cincinnati) so I was interested in knowing her more. After corresponding by text initially, I finally became brave enough to talk to her on the phone. I was so insecure of my voice. From there, our first date was a local drag show at a gay venue midway between our homes. From then on we became a couple for ten plus years until we decided to get married. 

I guess the moral to my story is, the darkest moments of your life can turn around if you continue to put yourself out there. Sure it hurts and is painful to be rejected but often there can be a light at the end of the tunnel. The sad part is, you went through a transition to find your authentic self and you discovered self love and now there is no one to share it with. 

On the positive side, I am seeing an increase in wives staying with their transgender spouses when they transition. I have the utmost respect for the love expressed by these women and wish we could all experience the same. 

Supporting Casts

 

Girls Night Out. I am on the Left.
From the Jessie Hart Archives

One aspect of my gender journey, I don't mention enough is the importance of the supporting cast I had around me to help me along.

They clearly helped me during the times of my life when I was down and almost out when it came to me going any farther as a transgender woman. A prime example was when I started gender affirming hormones and was wondering if it was the right move to make. By just being a part of my life and understanding what I was going through brought about a significant need for moral support. Another example was when I began having hot flashes and my women friends (cis-gender) just smiled and said welcome to their world. Which is exactly where I wanted to be. 

Over the years, there was only one woman who held my gender issues against me. She was my first fiancé who in the past, one time cross dressed me head to toe as a woman. The whole process turned out to be a bittersweet experience. For the first time in my life I had tried to share my deepest secret with another person and turned out to be less than impressed with the entire outcome. When she had finished with my makeup, I saw no real improvement over my efforts which ended any ideas I had that women had an edge over cross dressers when it came to makeup applications. So, the sweet part was limited and doomed to fail to begin with. The bitter part came later on when my fiancé broke up with me after I refused to say I was gay in order to not be drafted into the military during the Vietnam War. Lesson learned and I went back into my deep dark gender closet for years until I met my first wife. Even though she always knew I was a cross dresser or transvestite, she never made a big deal about it. 

Around that time of my life the biggest support I received ironically came from a man. A stranger who was doing makeovers at a cross dresser mixer I attended. I put on my big girl panties, removed all my makeup and let this stranger work his makeup magic on my face. When he was finished, I couldn't believe the transformation. Plus, I was actually able to understand and redo the makeup steps and repeat them. The entire process takes me to my experiences with my second wife. Similar to my first wife, she knew I was a transvestite from day one in our marriage and even supported me...to an extent. Keep in mind, we were married for twenty five years and during this time, I was slowly transitioning more and more into the transgender woman I am today. Before my wife's untimely death, we had numerous fights over my desire to be a woman and begin gender affirming hormones. Her stance until the end was she didn't sign up to be with another woman. To make matters worse, I don't think she ever liked my inner feminine self and the two women battled continually.

After she passed on, it took me a few years for me to recover from the shock and get on with my life. One positive I carried with me was how affirming the presence of my feminine side turned out to be. As it turned out, destiny led me to other groups of women who essentially adopted me into their tribes and helped me to flourish. 

I can never say enough how much I learned from all our girls nights out together. Without all of them I can never imagine how much longer and which direction my transgender transition would have taken.  

Empty Houses

Photo from the Jessie Hart
Archives

 As I grew up in a male world, I naturally adopted many male dominated activities and hobbies which I stored away in my house I had to build as a guy. 

Mainly because I was frantically chasing
my desire to be feminine, I sometimes jumped from activity to activity rapidly. Plus none of this was accounting for the traditional male things I was doing such as building a family and trying my best to provide as good of a house I could. As far as actual house goes, I was trying to follow in my Dad's shadow and come as close as I could to either remodel or build my own house. He built his own house while I worked hard to renovate an 1860's era brick tavern in the town I was from. I came close but I don't think he understood why I did it. 

Bu it wasn't easy. I needed to teach myself the basic's of plumbing and electricity among other important things associated with remodeling an old structure. The end result was my second wife and I were able to live comfortably there in the years before her death. Then, I was all alone with a couple dogs and a cat in this huge empty house. At that point, I needed to decide which direction my life would take physically and mentally. What I mean was, was I going to continue to try to live in the house I remodeled with all it's memories or try to move on. With all the animals of course. What I decided to do was make the house even emptier by selling all my wife and I's vintage collections on line and using the money to augment my Social Security money I was making. In doing so, I managed to keep the house going for awhile as I sought out the possibility of taking an early retirement. Eventually, years later, I was able to move us all in with my current wife Liz in nearby Cincinnati, Ohio. 

As it turned out, the physical aspect of having an empty house was much easier than the mental part. Since during my life, even though I started out shy, I became a rather social person with deep ties to my home town. Sadly, those ties had nothing to do with my increasingly dominant feminine self. With no one to stand in my way, I was actually able to pursue if I was indeed transgender or not. Or just a serious crossdresser who wanted to their best to look like a woman. Since I had the options and inspirations to discover my true self further, I finally gave in to my inner female and set out to attempt to build a new life.   

Surprisingly, leaving behind my old male life was easier than I anticipated. Destiny (and effort) led me to meeting a new group of cis-gendered women friends I could be social with and learn about a new house at the same time. Plus, all the years I dreamed about decorating a new empty gender house came to pass as I adopted relatively easy to my new gender affirming hormones and life as a fulltime transgender woman. Then my relationship with Liz, who I met on line flourished, and we were married years later after my daughter suggested we finally do it. She made sense, we married and moved on to a new chapter of building my feminine house and making it much less empty.

I am sure, when one discusses genders, not many humans get the chance to empty one house and start all over again in a new one. It is a scary yet exciting journey. 
 

The Audacity of It

Image from the
Jessie Hart Archives

When you view the transgender community from the outside, I'm sure more than a few people, other wise known as transphobes, think we are nothing more than a group of people asking for audacious demands. 

I know with me, I often felt audacious in my demands on my wives as I transitioned towards being a transgender woman. After all, my wives were seemingly making all the sacrifices in the relationship as their man faded away. Through it all, yes I did feel guilty but at the same time, there was nothing I could do. Gender change was impossible as I journeyed along the path to eventually leaving my male self behind. Since deep down I knew there was nothing I could do about my gender issues (and or cross dressing), I knew my wives would eventually have to get over their misgivings and I would get my way. 

Also, I need to say both my first and second wives knew I was a cross dresser before we were married. I don't think either woman really cared until it came to me becoming more serious about living increasingly fulltime as a woman. My first wife was very easy going and never really pressured me before we broke up. My second wife was much more opinionated and did participate somewhat with my transgender self but never really liked my feminine self for whatever reason. From the beginning and all the way until she passed away, she drew the line at me starting hormone replacement therapy and taking another giant step along my gender path.

The audacity of it all came when she said she didn't sign up with me to be with another woman and she was right. There was nothing I could say. I will forever wonder if she ever would have come to get along with the woman I always was before she died. Of course I will never find out.

Then there are all the transgender haters or transphobes who have the ability to change our lives in the real world or as keyboard cowards (as I call them.) The audacity of all of them to intrude upon our lives speaks for itself. The only defense I can think of is, the transphobes can't and won't take the time to understand trans women or trans men. The unfortunate part of it is that just consider how long it takes most of us to understand our own gender issues. I know in my case, it was a real struggle to come to any understanding of what was going on in my life. 

The biggest audacity for me now is the fact I don't care what the world thinks of me. Especially transphobes and/or TERFS. Now I can face the world as my authentic feminine self with a tight knit group of family and friends around me. Plus I am a role model of sorts for my transgender grand-child. 

Being audacious all those years when I was struggling to learn the world as a transgender woman left me with so many scars. I learned the hard way to develop a thick skin and keep learning all the important lessons I needed to discover. The whole process was terrifying but all so satisfying.    

We Met in a Mirror

Image from Laura Chouette 
on UnSplash

Along the way I have vivid recollections of how I met most of the memorable cis (or natural born) women in my life. As it turned out, I married several of them. 

Perhaps the most important woman I met was myself when I glimpsed her for the first time in a full length mirror we had at home when I was growing up. All I really remember is the feeling of gender euphoria I felt. Something clicked mentally and I knew somehow, someway I needed to try to cross dress again and even do my best to perfect the image staring back at me. 

Over the years, the problem became I became too addicted to what the mirror was showing me. For as much as I loved playing in the mirror, I was to learn the hard way the whole process was a one way street. As I broke out of my gender closet and into the world, the public did not see me the same as the mirror did. Stares and laughter all too often followed me around during my earliest gender adventures as a novice cross dresser. 

Still I persisted and learned without the help of the women in my life. The only one who tried turned out to be a dismal failure. She was my fiancé from my college days and I talked her into dressing me head to toe as a woman. I say failure because after she was done, I did not see much improvement over my efforts. Plus, over time, she held my gender issues against me and even wanted me to tell the military I was gay to stay out of the Vietnam War. Something I never did and went off to serve my three years, away from her. Which was a real blessing from many angles. 

From there I stayed mostly single until my last year in the Army when I met my first wife who was in the Women's Army Corps, also stationed where I was in Germany. We stayed together after both of us discharged all the way to when we had my only child, a daughter. My first wife knew of and mostly accepted the fact I was a cross dresser before we were married and was never really bothered about it. During this time I was beginning to learn my new life was everything but living in a mirror. I was beginning to take on the world as my authentic self when I met my second wife.

I was working at a radio station in Ohio where we met and I just knew I had to divorce my first wife and be with her. She was so full of life and strong willed, I thought she might do me good and went all out to be with her. Through it all, she as my first wife knew I was a cross dresser and accepted it also. We were married for twenty five years until she passed away from a massive heart attack at the age of fifty. Till the day she died nothing changed about how she viewed my cross dressing but she firmly drew the line at no HRT hormones or for me going towards being a transgender woman at all. 

As I wrote in my post yesterday, I was between the rock and the hard place when if came to my transgender issues. I had taken the steps to firmly move out of the mirror and into the world. The mirror became the place where I just checked myself out every morning to see if I looked masculine or the least bit feminine. Most of the time setting off my gender dysphoria or despair. I finally came to the conclusion nothing was as bad as it seemed or as good as the mirror tried to tell me. I had come to the middle point I needed to meet in the mirror.   

Gender Pilgrimage

 

Gender Pilgrim Troye Sivan

At the age of seventy four I often look back at my life and wonder how I was able to navigate the ups and downs of a gender pilgrimage. 

The way I have been able to separate my path is to roughly divide it into three segments which over simplifies the process but at the same time, makes it easier for my noggin to grasp. 

The first and most foggy time of my gender life was my early childhood. I don't remember exactly when I had a concrete idea of wanting to be a girl. I finally came to the conclusion it was around the age of ten. It was about this time when I started to explore the delights of feminine clothing from my Mom's wardrobe. From then on I started to save my allowance money as well the meager funds I earned from delivering newspapers to the rural customers we lived around. I had a powerful motivation to earn my own money and purchase makeup or clothes depending on what I could afford. 

The whole process set me firmly up for a nearly half century of cross dressing. As you can guess I had plenty of time to try different things while I experimented more and more deeply with being a woman and leaving my male life and privileges behind. I write often how I went about meeting other transvestites for the first time all the way to being approached by men. I was on cloud nine for weeks following an adventure I had after being made over by a professional at a cross dresser mixer I went to. Afterwards when I tagged along with the group I called the "A" listers, in a bar we ended up at, I was the only one approached by a guy who wanted me to stay and have a drink with him. The entire evening validated my desire to be a woman more often and at the same time made me hell to live with.

Sadly, I was destined to live this way for years, twenty five to be exact as I punished my wife for how I felt. I drank too much and tried to outrun my gender problems by changing jobs and moving to different states such as New York from our native Ohio. Instead of making my pilgrimage easier, I was attempting to make it ever harder. It almost killed me in the process as my mental health declined. The ripping and tearing of living between the two primary binary genders was just too much. I had to decide which way to go and made the choice to live in the future as a transgender woman. The problem was I was in my early sixties when I decided to leave my cross dresser phase and begin HRT or hormone replacement therapy. 

Of course now I am in the third phase of my gender pilgrimage and feel so relieved to having left all the turmoil of my male life behind. I know I did not make the wrong choice because I feel so natural with my life now. Out of an extreme level of caution, I certainly did well but on the other hand, I don't regret the male life I was able to live. Among other things, he gave me a wonderful accepting daughter and helped open the door to a relationship which led to a marriage to my wife Liz. 

I look at it this way, I was fortunate to have earned a dual gender citizenship by living on both sides of the border. An often long and difficult pilgrimage made it all possible.    

Coming Out to Employees?

 

Halloween Witches Ball Image
Liz on Right 

As we rapidly approach Halloween and my wife Liz's operation coming up, I thought it was time  for another Halloween experience while I still had time. 

This one happened when I was managing a fast food restaurant just outside of the New York City  metro area. More precisely, very close to the Bronx. As Halloween rolled around, once again  I was stressing out about what I was going to wear. The pressure was on since it was nearly impossible for me to leave the house we lived in dressed as my feminine self. I was back in the mode of waiting another year to escape from my mirror until the next Halloween rolled around.

As I faced the pressure head on, I decided to go all out as I decided what my "costume" was going to be. I put together what I thought would be a potentially a sexy look without crossing the line into being trashy. I pulled out my shortest dress, along with my highest heels. Most certainly, my wife's most hated outfit on me. In this case, I used her motivation of me to spur me on. For once, since she wasn't going anyhow, I decided she would have to get over it. I would have to put up with her displeasure with me for the next several weeks but it was worth it for me to pursue my dreams.

As I said, my outfit was going to be short and sexy as I to the best of my ability fool the world to what my true gender was all about. Little did I know, I would be able to find a situation where I was able to blend right in. 

As it turned out, one of my assistant (woman) managers was going out to one of her local taverns to celebrate Halloween with her friends and she invited me along. After I dressed, did my makeup and hair and was ready to go. When I arrived at my manager's house, it turned out the friends she was going with turned out to all be tall and beautiful . As it turned out, by pure accident, At least in the height department., I fit right in. When I first saw all of them, as the room grew silent, you could have heard a pin drop. Time seemed to stop for me as they examined me from head to toe. Of course I could only guess what they were thinking as we left for the short walk to the venue where we were going. Thank goodness for me (in my heels) it was not a long walk.

As we arrived, I learned a valuable lesson about being with other single women who were attractive. The first thing the women did was essentially split and worked the room. They left me on my own which was an experience in itself. After I bought a drink and found a seat at a small table, I settled in to try to enjoy my evening in the world as a novice transgender woman or even a transvestite. And it turned out, the night was far from over. As I tried to sit by myself, I attracted attention from an older guy who kept bugging me to dance. Which I refused although deep down I was flattered. Finally, the night was over, the group of women broke up and headed their own ways. 

I ended up back at my restaurant which I knew was closed by then. What I didn't count on was, the closing crew would just be getting done and they would see me in my "costume." Surprisingly to me, the response was positive even to the point of one of the guys saying I had good legs. 

More importantly, the backlash from me dressing as a woman for Halloween was a non starter for most of my crew and life went on. The only variable was my assistant manager who I think couldn't wait to tell my boss who smiled at me differently for awhile. However it was New York and there were bigger issues to deal with than me dressing as a woman for Halloween. Which was one of the reasons I wanted to move there from our native Ohio to begin with. 

As far as my second wife went, she finally made me pay my dues as only a woman knows how to do. I learned from it and moved on. Knowing I had been able to experience a truly wonderful evening to think about and remember forever. 

Gender Walls

 

Image from Marcus Loke
on UnSplash

One of the reasons I waited so long to transition into a fulltime feminine world was when I tried to escape the walls which were forever threatening to close in around me.

Little did I know, each successful move I made came back to haunt me. Ironically, success just showed me perhaps I could live my dream as a transgender woman. Before I arrived at my final conclusion, I needed to seemingly transition more and more on my gender journey. My prime example has always been the time I decided I needed to change my mind set when I went out into the world cross dressed as a woman. Somehow it occurred to me I needed to reverse my thinking and decide I was going out as my authentic self  and all this time in my life I had been crossdressing not as a woman but as a man. When I realized my gender truth, I began to feel increasingly uncomfortable in the male world I worked my entire life to be successful in.

Very quickly when I went down this new path, deep down I knew I could never go back. I was suddenly sliding down a very slippery slope to a new life. A life I felt very natural and excited to be a part of. I had no idea if the outside world perceived me as being any different and I may have just been playing with semantics but as I said, the feelings were much different for me. I had crossed the line in my mind from being a cross dresser all the way to being a transgender woman. The first night I tried to change and was successful was when I went all out to dress to blend in with a group of professional women who always gathered after work at a nearby "Fridays" venue for an after work drink. Even though I was scared to death, I was able to relax and enjoy myself to the best of my ability. The best part was, no one gave me a second look. The bartenders were nice to me and I knew I was changing forever. 

Following all of the excitement and gender euphoria, ironically the walls began to close in on me again. What would I do with all my new found freedom to cross the gender border. I still had a wife I loved of twenty-five years, friends and family plus a very good job to consider losing. The pressure was intense. With the pressure I began to do all the wrong things. Primarily when I began to emotionally cheat on my wife by going out as my feminine self as much as I could. Of course, I was caught on numerous occasions which led us into massive relationship straining fights. While I never cheated on her physically, the emotional cheating was bad enough to put extra strain on me which I didn't need. All the pressure eventually led me to another self harm (suicide) attempt and my wife finally telling me why I wasn't man enough to be a woman. She passed away before she was able to see how prophetic her words finally became.

The end result of all her criticism became, I re-committed myself  to learning more and more what my life would mean to me if I took the final steps to living as a fulltime transgender woman. My steps included being cleared by doctors to begin HRT or hormone replacement therapy. At that point I knew there could never be any turning back as eventually I changed my legal name and settled into a new life with my wife Liz. 

Of course my final wall to overcome will be if and when I need to face what will happen to me when I have to go into assisted living or face being mis-gendered by part of my family when I die. It seems there are always walls to face when you are transgender. 

What If?

Picnic picture from the 
Jessie Hart Collection. Liz on right.

Often I think about what my life would had been like if my wife had been transgender and I was the one trying to deal with it.

What if she wanted to become a he and started to date other women? Of course the easiest answer would be I would be the accepting one but would I have been if I had never been trans. Then I think of the amazing spouses which have come to acceptance of their former husbands new gender. The wives who come to understand the internal self is the important part of the total person are so special and in so many instances so rare.

My second wife, as well as my current spouse are prime examples. My first wife was a very much go with the flow person and I often thought if I told her I would be gone for a few months to complete gender reassignment surgery, she would have not missed me. Second wife was very much against me being a transgender woman at all and Liz, my current wife encouraged me to follow my gender dreams. I guess you could say I covered almost all the aspects of being married when all my spouses knew I was at the least a cross dresser or transvestite from the very beginning of our relationships. The only feeling I hid was the fact I was so much more than just a relatively harmless cross dresser just pursuing a hobby. My excuse is the whole time I was hiding the truth from myself as I tried my best to live a lie as a male person.

Looking back at my second wife a little deeper, I think she was suffered from a little paranoia of her own sexuality. We were members of a very active civic organization which did an incredible amount of good in the community. Within the group were several women whom I considered to be lesbians as well as a couple gay guys. All were in the closet and nothing was ever said, I think. What I wonder is if my wife ever was attracted to those other women and was in fact some sort of an embedded lesbian. It is all speculation on my part because she passed away in 2007.  Sometimes I think she protested my gender dysphoria too much.

 The exact opposite happened with Liz, my current wife. When we met, I was still trying to live a life which straddled both of the two main gender binaries. Within a very short period of time, she told me I should shed what was left of my male self and live entirely as my feminine self. As it turned out, she was the final push I needed to come out of my closet and live as my authentic self.

For all of you who are fortunate and have an accepting spouse, you have an understanding of what I am attempting to say. Gender is such a basic need and to change it is such a big deal. Often the road to acceptance for wives takes years. If you have the power to do it, try to understand all the dynamics which are going on. Plus, if you can do it, try to put the shoe on the other foot and what if your spouse was considering changing their lifestyle in such a dramatic way. 

What if you could change or not.