Complacency

 

Summer Image with padding.
JJ Hart

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

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

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

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

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

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

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

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

It is NOT a Choice

Image from Alexander Grey 
on UnSplash

I still get aggravated when someone says being transgender is a choice.

Realistically, why would I have ever chosen to live the life I am living. Would I have made the choice to give up everything I worked so hard to achieve just to put on a dress, makeup and heels and attempt to live a feminine life. All the material benefits I had acquired as part of my life as a white male privileges disappeared for good, if I wanted them to to or not.

Suddenly, I learned the hard way what it was like to have my personal security threatened as well as being mansplained when I attempted to insert my feelings on a topic I knew quite a bit about. Quickly I discovered many examples. I nearly found out the hard way, if I dressed too provocatively at a mixer, I would be cornered and harassed by an over bearing transvestite admirer. In an instant, I learned how it would be to be a helpless woman being overwhelmed by a much larger man. Not a pleasant experience and it was not all of my lessons. One night when I was blissfully minding my own business on a dark city sidewalk, I was approached by two sketchy men wanting a handout. Fortunately, I still had a lone five dollar bill for them and they went on their way. From then on my new feminine common sense began to grow and I started to develop the gender protective sense all women acquire as part of their life experiences.

None of what I was experiencing was a choice and not part of me being validating  myself as a woman. All I needed to know was I had no choice but to follow my path if I was able to look myself in the mirror and know I was doing the right thing. Coupled with the natural feelings I was experiencing, my supposed choice was made. 

I knew over a span of time, I would learn to deal with being mansplained was something I just had to deal with as a transgender woman. I will never forget the day I had to sit in a tow truck and be subjected to being bored when the driver was telling me how the truck worked. Finally, I gave him my best blond act until he finished all his rock bottom explanations. On one of my few dates with men, quickly I found I knew nothing about subjects such as sports and politics.

Why would I choose to be something as difficult as being a woman? My entire life became dedicated to proving the world wrong. I could carve out and experience a new life as a transgender woman and thrive. But again, I needed to prove all the naysayers wrong. The only natural feminine attribute I started with was my brain. Which for some reason, kept telling me I was doing life completely wrong because I was living it as a male instead of my more natural female. Finally, all the pressure to change and all the stress to explore the world as a trans woman. I was living in a world of alternate facts which was increasingly too complex to handle. I came to the point where I felt as an impostor when I went out of the house as a man. Can you imagine that? Feeling as an impostor when you attempt to live as your birth gender. It happened to me.

All the process proved to an outsider is gender issues are not a choice. During the process none of us understands, we are born into system we never asked for. The path is often a bumpy one with plenty of curves and stop signs. We have to wait our turn before we move on. 

For any number of reasons, the true number of transgender women and trans men may never be known. One thing is for sure, there are many more hidden transgender individuals waiting to take their turn and enter the world. Regardless of all the negative publicity we receive, transgender people have been around forever and will remain a part of the human experience. After all, we don't have a choice.

Opening New Doors

 

Ohio River image.

It took me over a half a century to open all the possible doors I could before I decided to begin gender affirming hormones and transition into a full-time feminine life.

For any number of reasons. I over-reacted and resorted to excessive experimentation  before I quit knocking on so many doors. Such as, behind door number one was a wife who did not approve.  Other doors had the usual questions such as what would I do with my friends. extended family and employment. 

Before I could make it to the other main doors, I needed to prove to myself beyond any shadow of a doubt, I belonged in the world as a transgender woman. What took me so long was I needed to live my male life at the same time as my new femininized life. Switching back and forth between the male and female genders took a toll on me but I kept slowly finding new doors to knock on and walk through. What I did was single out a door to go through and then judge the reaction. If I was successful, I would look for another door and if I was not, I would go back to the drawing board and attempt to figure out what went wrong. Often I found out the hard way that even though I was accepted in many venues, in others I was not. Mainly when I pushed the envelope too far and journeyed into the wrong redneck venue just to see if I could. 

Other doors I attempted to open and was successful is when I went to very small diverse mixers at an acquaintance's house in Columbus, Ohio. During the parties, I was able to meet all levels of the transgender community and see how I measured up. Especially with one of the transsexual women who I admired so much. Even though I did admire her, I learned her life was not applicable to mine and I had to keep looking for my own door. Since her path would not work for me. She was a soon to be retired Columbus fire person and was looking forward to a good pension to support her as a single woman. Plus she had good insurance, and I had none of them, I wondered how I was ever able to make it to my dream. 

On occasion, I grew frustrated with the number of doors I needed to go through. It seemed just when I thought I was successful, I was met with a dead end and needed to turn back. I did purge a few times and tried to put my male self in total control but deep down inside I knew the purge was only temporary and my girl self would re-emerge. She always did, stronger than ever searching for the mysterious, magical next door to go through. Sometimes it seemed as if I was stuck in a huge gender maze trapped and looking for a way out. 

Finally, I knew it was time to put my maze, doors and gender past behind me and do the right thing. I found the way out I was always looking for and she was with me all along. All I needed to do was admit the truth. All those years of looking behind all those doors made me aware of one main thing, don't wish for what you want because you just may get it. 

I wished for a full time transgender existence and kept opening doors until I got it. 

How I Became a Lesbian

Image from V T on UnSplash

Looking back, perhaps I have always been a lesbian. 

When I had to live as a guy, I intensely studied everything female and I never considered having sex with another man until I transitioned much later in life. At that point, I was wondering if my sexuality would change when I started living as a transgender woman. It was a highly intensive personal topic I put off questioning until I could not put it off any longer. 

Then I had help from other women such as Amy who instructed me to buy bananas to practice with, without becoming too graphic. She left little to the imagination. Plus, the problem was, I still did not know if I wanted to be with a man sexually or not. The only thing I did know was, since I had started going out in public as a transgender woman, I was totally embraced by more women than men. Probably for two reasons. The first being many women were just curious what I was doing in their space. The second is that generally women are less uptight about their gender than men. Who are very insecure. I just knew, for a change, I was enjoying my life much more and I was much less lonely. 

Still, I was not interacting with card carrying lesbian women and still did not understand the layers of their society. I knew nothing of femmes, butches and even super butches not to mention baby dykes. There are probably more than I can remember such as soft studs. Slowly but surely, I began to learn all about this when I began to regularly frequent two lesbian bars in Dayton, Ohio. Sadly, they did not exist for a long period of time and before they had closed I had moved on to mainly big sports bars where I could watch the games. 

By pure coincidence in the sports bars, I ran into two lesbians. One was the Mom of a bartender I knew and the other was there to pick up a to go order and slid a note down the bar to me. Over time and amounts of beer we became friends and met often. Plus, at the same time, a super butch I knew asked me out for dinner before he actually transitioned into a transgender man. It was my first date with a man and I was very nervous as he was fond of telling me later. 

With all the lesbian interaction I was having, I had the chance to go to lesbian mixers they were going to. My confidence rose when I gained acceptance at most of the mixers. Even to the point of joining up with my future wife Liz and going to a roller girl event in Cincinnati. And, I forgot to mention, Liz and I met up on an on-line dating site under a woman seeking woman category. So yes, she is a lesbian too and our first date was to a drag show. 

Sadly now, most of the lesbian clubs and bars have closed and gone away, leaving a big gap in the LGBTQ world. Personally, through my interactions, I learned so much. Including my validation as a person did not have to come from a man. Plus I was entertained and made friends when I needed them the most. Liz and I are going on over a dozen years together and happy. Proving I was a lesbian all along. I was just waiting for my male self to get out of the way so I could totally express it.

It turned out my sexuality was never in question and I only kissed a few men to know the direction I wanted to go. I owe a debt of gratitude to all the women who accepted me.    

The Lifelong Question

Image from Shifazz
Shamoon on UnSplash. 

During my life, I have had several burning questions. One of which of course was how I ever made the determination I was transgender.

Before we get to the main question, we need to examine several of the other issues life threw at me and possibly you also. The first direct non gendered question I encountered was the Vietnam War. Or, how was I ever going to negotiate serving time in the military, as I risked my life. As it turned out, me serving my military time turned out to be a gender question too because the closer I came to being drafted into the Army, I began to resent the fact women did not have to face the draft also. All in all, a waste of time, so I gave it up. As it turned out my service in the military had far reaching positive consequences for me because among other things, I met the mother of my daughter there. 

Another question arose when I was not so blissfully cross dressing parts of my life away and I wondered if I was the only one with similar gender issues, I was stuck in the pre-internet dark age of having very little public information available to me. It wasn't until I served my time in the Army did I discover there were indeed many so called males who wanted to be femininized into women. The problem became was what was I ever going to do with my new family. Certainly, fathering a daughter had not made me more of a man, No matter how macho I acted. 

The older I became, it seemed the more complex my problems became. In fact, my thirtieth birthday was the most difficult for me to negotiate of all my birthdays. At the place I was in then, I was in deep despair over what decisions I would have to make to survive. What I determined was I needed to find better employment, stop drinking as much and resolve to be a better father. I was a success at finding better employment but a dismal failure at curtailing any of my party life, which included the Halloween parties I was going to dressed as a woman of course. All I really did was procrastinate further on the major question I had which were my gender issues. 

When I began to complicate coming out into the world as a transgender woman, I first had to determine in my own mind if I was indeed trans. Once I did, I needed to figure out who I would tell. Since most of my immediate family and closest friends had passed away, the list I had accumulated was very short. First to tell was my daughter, my only child and I suffered long and hard with if I should tell her at all. My reticence was rewarded with relief as she accepted me without question and still wanted me to be involved with my grandchildren's lives. I also questioned coming out to my only brother because I knew his in laws were religious right-wing bigots of the first degree. We both went our separate ways over a decade ago. 

The more life progressed, the tougher decisions seemed to be because there was more to lose. Another primary example was my job which I had worked very hard to be successful. I knew the company I worked for would never accept a transgender manager, so staying put was out. Fortunately by this time, I was old enough to be within reach of taking my social security retirement. So I just retired and started gender affirming hormones. 

The lifelong question of why me mostly answered itself. I played the odds throughout most of my life and was for the most part successful. For better or for worse, I was able to hide my true gender feelings until I could safely transition. Along the way, I also found I may have never had the chance to decide my gender anyway. My Mom had suffered through several still births before me in the late 1940's and had taken the DES medication. DES as I have read flooded the womb with estrogen and has been linked to the possibility of causing  transgender children. Who knows? 

Having all these major questions in life is just another facet of being human. Some questions are more difficult than others. 

Escalation or Escapism

Halloween image from the 
Archives. Min on right. 

During my life, I spent many uneasy moments in my transgender transition when I was caught between escalating my feminine gender craft or escaping back into my well worn, boring male world. 

The problem quickly became the more I escalated my attempts at being a girl, the more I wanted to do. More and more drama set in as I viewed myself in the mirror. Through it all, I wondered if I could ever put it all together and go out into the public as a novice transgender woman. Following years of escaping back, I finally did take a few tentative steps into the public eye. The first night I tried, I had decided to go to a small book and carry out convenience store just to see what would happen. I arrived and walked down the sidewalk near the store in a shopping center. As I tried to gather my courage to go into the store, I attempted to sneak a look at myself in the clothing store nearby. I could not really see my reflection and began to re-think my idea of going into the store I planned on. Then I decided my idea was not a good one and I headed home to escape back into my male self. 

For awhile, I felt relieved at my decision but then began to think I had taken the easy way out and if I continued on this path I would never discover if I could make it in the world as a transgender woman. Once I was able to locate and buy better fashion choices, including shoes and wigs, my mind started to change as far as escalating myself in the world. After going down a very bumpy road, my confidence increased to the point where I could try out the public again without escaping back to my safe male self. Even still, each time I did escape back, I grew increasingly disappointed in myself and very frustrated in the fact I was wasting all the time and effort I was putting into my femininization. 

Through all the ups and downs, I was slowly but surely gaining small amounts of confidence in what I was attempting to accomplish. In fact, I was scared of how intimidating the entire gender transition process was to me. Many times, I thought I was in too far over my head and was going to drown my entire existence in my quest to be a woman. Something always told me to keep going and the dream I was following would be worth it, so I continued to escalate my transition. 

At that point, one of the biggest surprises which happened to me occurred when I found out how welcoming other women could be. Very quickly I found women were way more apt to approach my feminine side and in return, I could learn how to interact with them also. There was nowhere to go and nowhere to hide. so escaping was out of the question. Mainly because I was living through one of the most exciting times of my life. Why would I ever want to escape. 

Still I found I needed to escalate my gender transition. My primary example was when I suddenly had a major mental shift one night when I was going out into the world. As I was going through what I was going to wear and how I was going to do my hair and makeup, it came to me I was no longer going out to trick the world into thinking I was a female, I was going out as a full-fledged transgender woman. I had taken my escalation to a whole other level and one I never wanted to go back to.  When I turned out to be successful. 

When my male life was crashing around me, the easy answer was to keep escalating into my feminine world. Which I did with gender affirming hormones. The magic little pills I started with almost immediately began to femininize my body and my inner emotions. To this day, when I change and apply my Estradiol hormone patches, I thank the powers to be I was healthy enough to undertake the program. 

I believe now, escalating into my feminine world saved my mental health and my life. The more confidence I gained as a transgender woman, the quicker my male self evaporated away. There would be no more escaping. 

Gender Prison

Image from Denis Oliveria
om UbSplsh

Many transgender women and trans men have spent numerous years in their own gender prisons. Sometimes referred to as closets. 

Unless you have had to spend time in your own prison with the walls closing in all the time, you have no idea of how bad it is. Just another proof being transgender is some sort if a choice. Why would we ever choose to possibly destroy ourselves with our gender issues. It all got to the point with me, I was doing all I could to manifest myself being as feminine as I could. When all along my male self was telling me I couldn't. 

I finally arrived at the point where I was given free time from my gender prison to explore the world as my new self. When I did, most certainly I discovered I wanted more and more free time. I discovered also, I needed a ton of work to prepare myself for freedom. I was not prepared for all the challenges I would have to face as a novice transgender woman. Since I had spent so much time cross dressing in my life, I thought how much harder could it be. I never factored in what my second wife was always trying to tell me, I did not really know much about being a woman and she was not going to do much to help me out of my gender prison. 

When she told me that, I reverted back to working ever harder to understand what she meant. Since I had studied women closely my entire life, I resolved myself to trying to get behind the feminine curtain to learn more. It would take me years to get there since it seemed I was living a life time sentence in my gender prison. Outside of a few varied chances to thrive, my prison seemed to be escape proof. How was I ever able to leave my prison without jeopardizing all the white male privileges I had worked so hard for such as family, friends and employment. It seemed the more I tried to escape, the more the walls closed in on me.

Once I staged my big gender prison break, there was no turning back. I discovered that even though my wife would not help me pull back the feminine gender curtain, other women would and I took advantage of their kindness. Even when I was able to, I found I was still looking over my shoulder for any male prison guards who were chasing me. It turned out, even in heels, I was faster than they were and I managed to outrun my naysayers which mainly was myself. 

With practice in the world, I finally put my prison time behind me and I set out to live my dream life as a fulltime transgender woman. One way or another, I had paid my gender dues for nearly half a century before I had the courage to fully transition. It felt so good to be let out of my gender prison and not have to go back. 

My parole officers turned out to be the women friends I found and cherished as I learned so much from them about living in a feminine world. When I used their input and included it with what my own inner woman was telling me, I was able to make a smooth transition even smoother. Plus, I was able to use my prison time as a powerful motivator of what not to do in the world. Even as a man, I tried to treat women differently than the other men around me. Mainly because I wanted so badly to be one of them. 

In the end, spending all the time in my gender prison did not do much for my life. I spent so much mental energy rebelling against my male world, I often wonder how much farther I could have gone if I had used all my resources. It wasn't to be because I was in my own gender prison and could not find the key.

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!

Gender Black-Mail

Image from JJ Hart, Ohio River
in background.

 Even though I have been living as a transgender woman for over a decade of my life now, my male past still comes back to haunt me. 

I suppose I am expecting too much from my gender transition since I spent such a long period of my life trying desperately to fit in with a male world I did not really want any part of. Recently, sadly an acquaintance of mine who was a fellow DJ on a local radio station passed from cancer. When I learned, memories flowed in including good ones and those not so good. One of the more interesting memories I have was of the time his wife (also deceased) told me about a new DJ at the station I used to work at who actually was starting her gender transition. I was surprised she had a fairly positive reaction to the gender issues so long ago. Way before the term transgender was popularized. Why I am mentioning it at all is it always amazes me what I remember or don't remember from my male past.

As I moved closer and closer to crossing the gender border, it seemed my old male self had an unfair advantage over me because he always mentally pointed out the good times there were when I was a guy. It was similar to gender black-mail. He would always say what about all the good times I had with guy friends when we were out partying. Essentially, overuse of alcohol allowed me to forget about my gender dysphoria for awhile and I could have a good time for the wrong reasons.

In addition, it was so so easy to fall back into my old male patterns and enjoy all the privileges I had earned from surviving as a man. When I transitioned into a feminine world, losing those privileges made a significant impact in my life. It seemed at the time, when I encountered most men, single or in a group, they held it against me that I had left the male club for greener gender pastures. Their way of black-mailing me was to shun me from any or all contact. At that point, their resistance just showed me I was on the correct gender path and I was more and more encouraged to try to advance to my dream.

Another facet I mention often is how my second wife and my male self enjoyed ganging up on my novice transgender self. My wife in very begrudgingly situations would let me go out with her as my authentic self. Predictably, she didn't like me no matter what I did and when she was mad at me would say I didn't know anything about being a woman. I equate it to applying for a job you have no experience in and the company won't hire you because you have no experience but won't allow you to gain any. I was learning the hard way, she would not help me to go behind the gender curtain to women only spaces. It would take me years to earn the respect or right of other women to play in their sandbox. Even if I was getting sand thrown in my face. 

It was obvious at the time, I was experiencing gender black- mail from many women also. I was too much of a woman to be accepted by men anymore and still too much of a man to be accepted by many women. Eventually, I solved the problem by keeping pushing forward towards my feminine dreams. It was very difficult to stay laser focused on my goal when I was still trying to maintain a life in both of the binary genders. So before I totally destroyed myself, one had to go. At the time, I compared where I was at to standing at the precipice of a very steep cliff and fearfully looking over the side. When I could not take it any longer, I took a long time to consider my gender options and came to one conclusion. I had always been living a lie as a man and no matter how much black-mail I had to put up with, I knew which path to take and I jumped. 

The path took me to gender affirming hormones and I never looked back. I knew I had made the right choice when I felt so natural and satisfied with my life. It turned out the only real black-mailer in my life was myself.

 

Gender Anxieties or Paradise

Image from Cacique 
Nacimento on'
UnSplash

During my gender transition, all the way to today, I have experienced my share of anxieties.

Early examples revolved basically around the way I looked when I was cross dressed in my very limited feminine wardrobe. I kept telling myself I was OK when I with my cross dressing and I was for a couple of days before my gender anxiety returned. Making me difficult to live with. Paradise was fleeting and hard to find. 

Much later on in life, when I began to try out the public's perception of me, the whole process was anxiety ridden. When I used to shop till I dropped in clothing stores, my feminine life was easy because everyone was just interested in selling me something. Or I was in thrift stores where the clerks barely looked at me at all. Maybe because they were used to waiting on cross dressers? Very soon I came away with feeling no anxiety at all when I shopped so I felt I needed to challenge myself further. I needed to see if it would ever be possible to live my dream of being a full-time transgender woman. It was close to this time also when I began to seriously challenge the world as a woman at various Halloween parties I went to. Most of them happened when I was married to my first wife who knew I was a crossdresser  when I married her, so there were no surprises when she saw the "costume" I settled on. 

Even at Halloween, I experienced growth with my gender issues. When I dressed trashy, early on, I was treated the same way but when I decided to see if I could present as a business woman at the party, I was treated with more respect and even surprise at my true gender. Little did I know at the time when I dressed as a woman, I was presenting as my true gender. Very quickly I learned, Halloween was never enough and I needed to express my authentic self as a woman more than once a year. When I did, I began to do more of the household grocery shopping as a novice transgender woman as well as haunting the antique malls and bookstores for the perfect gift for my wife. Anything to take me out of my male comfort zone. When I was successful I was in paradise and when I failed, of course the opposite occurred and  I was sent back to my gender drawing board to re-think my plans. Could I ever make it to my dream the way I was heading. 

Spoiler alert, I could and did make it. Somehow and through the help of therapy I was able to work my way through a large amount of my gender anxiety. My therapist helped me to realize there was absolutely nothing wrong with my transgender desires. Which was as close as she could come to telling me I should proceed with my dreams. Paradise was reachable if I wanted to pursue it farther and I had already accomplished most of the hard work. I had established myself a foothold in the world as a transgender woman and it felt so good and natural, so what was I waiting for.

The answer to what was I waiting for was the outside chance my male self would finally get on board with my decision. He didn't and hung on to the bitter end. In fact he tried to ruin my transition all the way to when I was medically approved to begin gender affirming hormones or HRT. What happened was, the HRT changes were so dramatic, even my male self needed to finally give up and go away. He finally did, leaving most all of my gender anxiety behind and replacing it with a lifetime of feeling freedom such as I had never felt before. 

I had paid my dues and it was time to move on.

Mental versus Physical

Archive Image
Ohio River in
background.

Is presenting as a woman when you are born male more of a mental or a physical effort?

I think, in my case, I started out with a more physical experience and then moved on to a more mental one. Possibly, it is because it took me so long to grasp the idea I was more of a transgender person in the making and not a cross dresser. I have nothing against cross dressing but it just was not for me. I wanted to go past just looking feminine to being feminine. Sadly, because of the lack of information and other excuses, it took me decades to understand myself. During those times I tried anything I could to resolve my gender pain I was feeling. 

What I did not understand was the amount of pain I was feeling was due to the transition from being a physical appearing woman to a mental operating one. Walking the walk and talking the talk with the public as a novice transgender woman certainly took a toll on me mentally. Finally I was coming closer and closer to solving all the public gender issues I was feeling. Walking and moving as a woman started to feel more natural but communicating with the world as a trans woman was much more problematic. I was very self conscious about the tone of my voice among other things. 

Another concept I did not consider was for the longest time I tried to fool the public into thinking I was a cis-woman. Instead of just resulting to being my natural feminine self. When the public interacted with the real physical person who was me, women in particular were intrigued with me and wanted to know what I was doing in their world. When they learned, I was not up to no good, the response was for  the most part positive. At that point, the mental aspect had to kick in with being transgender. I needed to work on what I was going to do with my old unwanted male self and decide what sort of a life I was going to build for an exciting future.

How I appeared to the world as my physical feminine self was still important and I am not saying it still is not. It just that is much of my appearance became easier to approach because I was all of a sudden I was just dressing to blend in with the rest of the feminine population. An example was this morning when I did not have to put on a fresh face of makeup and a dress to make the short trip to the street curb to pick up the trash cans and bring them back to the house. I could do what the neighbor lady does and just pull her hair back, throw on a pair of jeans and get the cans. This is an extreme example I know but a realistic one when the mental part of being transgender meets the physical part. 

When the two aspects did come together, my life improved dramatically also. There was less stress on my mental health primarily when my feminine inner self took over. It was as if she was saying what took so long. The main reason I took so long to transition was I ran from the gender truth I was feeling for all those years. I should have realized I was born to be a girl/woman long before I did. I did not and paid the price.

I also do not feel good about convincing people like my first two wives to come along through my turmoil. I convinced them I was just a casual cross dresser at the beginning and I was trying not to go further into a transgender world. It was unfair to all of us, Since  I was the driving force in both relationships, it was up to me to do better. Instead, I decided to take the lonely gender path for most of my life. Until I could put the mental and physical aspects of being a transgender woman together and discovered I could settle in and live a good life.      

Trans Girl Destiny

 

Image from
the JJ Hart
Archives.

When I was given the keys to a transgender existence, on occasion I have to pause and consider how I have arrived here.

Unlocking all the mysteries of crossing the gender border proved to be more than I could deal with on occasion but I kept on moving forward. Trying to find out what it meant to achieve my dream of living as a transgender woman. Finally I learned to relax and let destiny take it's course. Before I could even begin to relax, I needed to learn the new rules of the road.

The rules of being a woman were not easy to learn before I was accepted for admittance into the club. I discovered along the way there were more female privilege's other than having doors opened for me by men. One of the biggest ones was being allowed to communicate with other women on a mostly non confrontational-passive aggressive platform. Along the way, the lessons learned were brutal and I ended up walking away with many scratches or claw marks on my back. Primarily I found not to even try to look at or get close to a woman's man. It frustrated me because the man always made the first move and I had no real interest at all but none of it mattered to the other woman. Another mystery solved as I worked my way towards my transgender destiny. 

During the years in between my final solution to my gender issues, I was held back by many circumstances beyond my immediate control. I felt pressure to maintain my marriage of twenty five years and a job I was rapidly progressing in. To maintain my life, I tried to balance my existence between the two primary binary genders which only provided temporary relief and in some cases, even made it worse. When I became more successful in living as a trans woman, I felt so good and natural, I just wanted more and more. Which included no going back to my old male life which ironically I worked so hard to maintain. Destiny was trying to tell me eventually I would have to give it all up and start over but I could not find the courage to do it.

As I waited and waited for my chance to transition, I came to the point of no return. Magically, at the age of sixty destiny really came into play. First of all, I was to the point when I considered gender affirming hormones as the next huge move I could make concerning my chance to live as a full-time transgender woman. As I was considering the move, the Veteran's Administration suddenly announced they would now cover HRT as part of their health care for veterans. Which I happened to be a part of. The only hold up was I needed to see a therapist at the VA for an approval. I still remember how nervous I was the first time I went to see my therapist and after a second visit, I had my approval for my life changing hormones. 

It was around this time too, my second wife had passed away. Leaving me very much on my own to consider any gender decisions. My choice as clear and impactful as destiny was showing me the way forward and leave my ill-fated dual gender life behind and live as a transgender woman. When I did, I found I had other major decisions to make such as the possibility of undergoing major gender realignment surgeries. I decided against it for several reasons such as I did not have any insurance to cover it and the VA in those days was not covering SRS at all. Similar to Medicare covering breast augmentation or facial femininization surgeries. I am not sure how much any of those entities support those surgeries to this day, so don't quote me on it. The only aspect I decided on was my gender was between my ears and not my legs and those closest to me viewed me as a woman. So I had achieved my goal.

I can't forget the final part of my transition life which destiny played an important role was the financial part. Since age wise I was so close to being able to retire early on social security, I could sell my vintage items on the side and make enough to go ahead and retire. Which meant I would not have to worry about doing a gender transition when I was working. 

So, I had secured my big three aspects of my transition so I had no real reason not to pursue my transgender dreams. Destiny worked for me.

Major Gender Differences

 

Image from Jamie'
on UnSplash

From the outside looking in, many see transgender women and trans men merely as people who have decided to dress different.

As I was applying my estradiol patches this morning, I thought how different the entire process is when you decide to come out into the world as your authentic self, be it as a woman or a man. It is the same process as when you transition from being a cross dresser to being a full fledged transgender person. For me, finding my gender destination was a long term process. I write often concerning the years of transforming myself into the feminine person I always knew I should have been my entire life. 

What I did not understand for the longest time, I was joining a whole new culture when I transitioned. No longer could I bluster my way through a world filled with white male privilege. I needed to strike out on my own to find out what living in a woman's world was all about. I learned quickly, I knew very little about it and what I did know was usually wrong. I kept feeling stuck until I could work it all out. Was I even doing the right thing trying to cross the gender border. Plus, what was I going to do about those who did not want me crossing the border at all. Fortunately, I learned fairly quickly most of the world did not care what I wanted to do one way or another and most of the public I was interacting with were in a financial situation when I essentially was paying their salary. Either from a commission at a clothing store or from a tip in a food or bar venue. Either way, being friendly worked wonders in my transition. 

Very quickly, people began to see me as a new person. A person I wanted them to see which caused me to add major differences of changes to my life. A prime example was how was I going to suddenly attempt to talk to the world as a transgender woman. The whole communication process was similar to starting all over again when I first explored the world. At first I was petrified to talk at all until I tried to mimic the women around me. The problem was if I didn't talk, I was coming off as mean or stand-offish.  I needed to solve the problem and solve it fast if I was going to survive in the world as a transgender woman. I needed the voice to match my appearance the best I could. It was a major gender difference I always put off pursuing because I was so obsessed with my appearance. One of my favorite accessories was my sunglasses which helped me watch the public's perception of me without them seeing mine. I could better judge if my appearance was making the grade. Which I hoped was a passing score. 

Naturally, the more progress I was able to attain in the world as a trans woman, the more confidence I had to try more living. Again and again, outside of a few ill advised trips to red-neck venues, I was able to stay out of the gay bars and make my way through the world. I had fun in the lesbian and sports bars I was accepted in and was learning more and more about myself. To be sure, seeking a place in the world of women was never easy and I needed to earn it. I worked long and hard to learn from my mistakes in public and go back to the drawing board when I needed to. Finally, I reached a point where I could put the drawing board away and make it on my own.

Validation as my new feminine self then became a priority if I was going to keep living as a transgender woman. I attribute my lesbian friends with giving me the guidance I needed to succeed, They showed I did not need a man to validate me and my sexuality did not have to change to live as I was. All important lessons I needed to learn if I valued my independence in a new world. 

Learning gender differences meant so much more than looks was very inciteful to me.  All the catch phrases such as walking the walk and muscle memory come to mind when it came to my transition. I had such a long way to go to separate myself from a very convincing male life, there were many times I did not see how I could make it,

To do it, I needed to attempt to study all things feminine until I got it right and when I did keep doing it until practice made perfect. Then and only then was I able to move forward on my very long gender path.

Damn it is Complicated

 

Image from Amanda Dalbjorn
on UnSplash

Crossing the gender border is never easy for the average human being. 

To begin with, you need to be very serious concerning your gender passion. You need to trust your instincts, close your eyes and leap. I took over fifty years before I could come to the point of being able to trust myself. After all, I had spent all of the time as a very serious cross dresser exploring the world to see if I could survive as a transgender woman. Some times I was good about making plans, sometimes I was not. As I took the good with the bad. Ultimately, taking the good with the bad, just walking a path I knew very little about. 

As I walked my new path, there were several points of reference along the way. Such as the mixers I was attending in nearby Columbus, Ohio. Many were big and more than a couple were very small and intimate. Regardless I learned from both and how internally complicated they were. All layers under the so called transgender umbrella attended one or the other. Everyone from seasoned transsexuals to very novice cross dressers often out for the first time in their lives away from the mirror. Through it all, I was trying just to find my way to discovering who I really was. All I did finally learn was I did not fit the mold of a stereotypical transsexual or a weekend cross dresser. I was somewhere in between. I found I was not everyone's cup of tea, I enjoyed being my own. 

Examples were everywhere, including the guys who cross dressed for certain mixers but not for others all the way to the impossibly feminine transgender women who made their appearance. I was drawn to the feminized crowd but often I was left out because of my looks. I had a long way to go with my appearance but I was trying hard. With the help of a professional makeup artist provided by the group one night, I learned the intricacies of applying makeup and could really help me because he explained everything to me. Thanks to his magic, I was able to move up in the eyes of the transgender or transsexual crowd. Even still, mainly because they shunned most of the rest of the average cross dressers, I stayed to myself. Except when the trans women went out to other gay venues after the regular mixers were over. When I did so, I was exposed to a whole new world of exposure in the world in my own transgender universe. 

As I did, my life became increasingly complicated. I needed to overcome inner clashes with my genders as well as trying to deal with the problems of dealing with my second wife who was against any idea I was transgender. The major problem, every bit of my self was telling me being feminine was the only way I could survive. All of my turmoil just led to more stress to my already fragile mental health. I ended up in therapy again, which did some good but were for the most part wasted because I refused to face the truth about myself. My authentic self was feminine and I needed to express it. The only thing therapy did was make my wife think somehow it was going to magically "cure" me or at the least, I was trying to help the situation. Which at the time was growing into a major problem between us.

When I first looked into the mirror as a kid so many years ago, little did I know how complicated my life would become as I grew into my gender issues. My gender path was so convoluted as I followed it, I often became lost. The only aspect which kept me going was the deep down knowledge I had been born to be a girl. Dealing with it was always the issue.

Buckle Up!

Image 
from the 
Jessie 
Hart
Archives

Recently, I have happened across several posts on my social media feeds from novice transgender women just beginning HRT or gender affirming hormones. 

In many ways, as I look back on my hormonal experiences, I am envious. Mainly because my experience was so exciting. Possibly because I was finally realizing my attempt to take a major step forward in my transgender transition. For years, I had dreamed of starting HRT, much to the chagrin of my second wife who was completely against it. She had always told me, she did not want to live with another woman and the hormones would take me dangerously close to doing it.

When I actually started down the HRT path, little did I know how right she would be. I was naïve and I thought my new journey would involve growing breasts and hair but never dreamed of all the other changes which would take place. My skin softened along with my facial angles which helped  my feminine presentation in the world. I could use much less makeup and do away with wearing wigs because I was fortunate I did not inherit any male pattern baldness.  

Before I knew it I really wanted it to happen, I was becoming very androgynous and had to do something. With my hair, breasts and skin alone, it was time to begin to think about the circumstances to what I was doing. Plus, I have not even mentioned all the extra benefits of going through the second major puberty in my life. When I did, I discovered so many new things about myself such as when my sense of smell suddenly improved and my body's thermostat went away. What happened was I was cold all the time and suddenly understood women were not making it up all the times when they said they were chilly.

Then there were the onset of emotions I went through when I started HRT. Previously in my male life I had become very insulated when dealing with my emotions. Sadly, I became so callous, I had a difficult time shedding a tear when my parents passed away. Suddenly, one night, when a late summer thunderstorm moved in, I sat alone on my side porch and started to cry for the loss of my old male self. It was such a powerful moment in my life, I will never forget it. 

Of course if you are just starting down your path to femininizing hormones, there will be many peaks and valleys or ups and downs. Similar to so many others, I questioned the gender path I was taking. Was it the correct one? So, I buckled up for the ride. I'm not sure now if I was ready for the first hot flashes I went through which hit me when I was out in public and I ended up wondering if the world had noticed I was getting ready to internally combust. Perhaps back in those days, the worst part of my gender journey was I had no one to share it with. I was just getting to know the small circle of women friends I started to hang out with on a regular basis and knew they would only say welcome to their world if I brought up anything such as hot flashes to them. 

After awhile, I came to the conclusion I had buckled up for one of the best roller coaster rides there were. The best part was, for the most part, I had no idea what was coming up next. When I was approved for larger dosages under the care of a doctor, changes continued to come at a rapid pace. Under medical care, I went from pills to patches which supposedly helped with the wear and tear on inner organs such as kidneys. Life was good as I adjusted to the new hormones and I felt as if my body was telling me I was a natural for gender affirming hormones all the time. 

The very few people who knew me pre-transition said it the best, I just seemed more relaxed and happy now as a transgender woman. I never said anything but I gave most of the credit for my new found joy to the hormones I was on. HRT had helped me to sync up my internal and external gender feelings. It would have been "TMI" or too much information for the average person to understand. 

I will always wonder how my deceased second wife would have reacted to me as a transgender woman. Would I ever have paid enough dues to move out of the pretty pretty princess mode she threw me in and ascend to the woman mode she was so afraid of. I would like to think at the least we still could have remained friends.  I will never know.

At the least, your journey will be different than mine in many ways and will include many twists and turns. Just try to enjoy the journey many others will never have the chance to take.

Much More than a Phase

 

Civil War Cemetery image
from the Jessie Hart Archives. 

When I was first experimenting with wearing woman's clothing, I worked long and hard to hide all my feminine wardrobe and makeup. 

Due to transportation and financial constraints I always had a difficult time adding to my very limited collection. Plus, I always wondered if my Mom ever really discovered her clothes and others I managed to "borrow" for my cross dressing trips to my mirror. If she did, she never confronted me about it. Perhaps she thought it all was a phase and I would grow out of it. Similar to the fallacy, being transgender is ever a choice, I learned my gender issues were much more than a phase.

Very early on, I discovered a lesson I should have relied on but kept on ignoring. The lesson was, I wanted to be a girl, not just look like one. The very beginning of the realization I was transgender as I envied everything girls around me did.  Which went far past their pretty clothes while I was stuck in my drab male clothes. All along I was stuck in a family which valued male superiority and I wanted to rebel but couldn't. I often wonder if I had been born into a more diverse family (if that was possible back in those days) I could have made my feelings known and thrived. Instead, I did the only male thing I knew how to do and internalized all my inner feelings. I even thought, if I ignored my gender issues long enough, they would turn out to be a phase and go away.

Of course my gender dysphoria never did go away and just grew worse as I began to understand the full depth of what I was facing. As I look back, Halloween parties were my first indication I could do more than living a shallow life in front of the mirror as a cross dresser. I learned the hard way, heels weren't so much fun when I first wore them on long walks all the way to how much fun I had experimenting with the clothes and learning from the parties as a whole. Another step towards showing me my phase was not going away, I was just growing into it.

Halloween parties proved to be false feedback in many ways. Most people who saw me were friends who thought Haha I was the clown dressing as a woman for a laugh. Even though I was going as far as shaving my legs. In my mind, my legs alone would do the trick and everyone would know I was much more than a once a year man putting on a dress. At least I wanted it to as I grew confident I could present more and more as a real woman at the party. When I had achieved my goal, I felt I was ready to pursue a future as a successful transgender woman. 

When I did, the work really started. Life was so much more challenging as I left my male phase in my past. I wonder now if my Mom ever thought my simple love of girls clothes was a phase, what would she think now. Outside of the one time I tried to come out to her as a transvestite and she rejected me, we never discussed it again before her death. I can't help but look back and regret how much life I may have lost if she would have ever accepted me. I on the other hand took the high road and honored her by using her first name as my new legal middle name.  

Normally, phases come and go but certainly none of it applies to being a cross dresser or transgender person. Once the public at large learns to accept we are not a phase, trans kids especially could benefit from more understanding when they are young. Parents and siblings could have a more serious outlook of what being trans is all about, helping the whole situation. Or, leave the phase out and help the person. 

Finding your Happy Place

From the Jessie Hart Archives 

 As a transgender woman or trans man, it is often very difficult to find your happy place.

A happy place can often be called gender euphoria for all of us who suffer from gender dysphoria. If you don't know, dysphoria is the often evil process of hating the gender you were born in. After all these  years, I still dread the first look in the mirror every morning. Who will I see looking back? My same old masculine self, or a femininized version of him. Some mornings I land in my happy place and others I don't. I usually settle on a middle point until I am done with the mirror.  On occasion too, I suffer from having an impostor syndrome. When I think do I even belong here at all. Happily, the syndrome goes now away quickly because I know I have earned my place as a transgender woman.

Earning my place was never easy as I never inherited any feminine characteristics to start with. What I did have was a testosterone damaged body to work with. The only positives I had to work with were the compliments I received  on my freshly shaven legs at Halloween parties.  Then I had the tendency to overdue it when I explored feminine fashion. I thought I should emphasize my positives such as my legs and at the same time play down my body negatives such as a thick torso. All of it led to massive fashion mistakes before I learned to dress to blend in with the other women I encountered in public. I lived through all of those and found a happy place I could live with.

Around this time was when my happy place location started to change and move around. It shifted from appearance only into a personality based place. Mainly because, suddenly I was closely interacting with the public as a trans woman. It all meant so much more to me than my days as a casual cross dresser. All I know was I was up to the challenge and enjoyed my new happy place everytime it presented itself to me. Outside of a few instances of impostor syndrome, I was learning more and more I could indeed live my dream of being a transgender woman in the world. It turned out my happy place did exist in the feminine world and more and more I wanted out of my old boring male existence. 

Still I had a lot of climbing to do to rid myself of the old baggage I needed to lose to transition. I wondered at the time what I would do about everything I loved in life such as my daughter, (hobbies such as sports) and what was left of my business. It turned out destiny took it's own course with my baggage. My daughter supported me completely while my brother rejected me, so I was the recipient of the best part of the deal. As far as my business went, it mercifully closed due to a weakened economy and other factors, leaving me close to having an early retirement. As far as hobbies went, ironically I found a group of women who were as passionate as I was about sports, so I had friends to watch our favorite games with. So as you can tell, outside of the obvious gender issues, I was able to restart my happy place without a whole lot of extra effort. 

When I found my new happy place, it felt so natural I wondered why I did not pursue it earlier. I know early on I was into my appearance as a woman completely and often missed the basics of movement and communication to further my femininity. It turned out I did not have to worry because the deeper I delved into my new life, the more fluid and natural I became. Practice made perfect in so many ways along with the fact I became secure into who I was. When I did, I didn't care what others thought of me and my confidence as a trans woman increased.

It turned out, destiny took it's time but ultimately led me the right direction.    

Going Through the Motions

Image from Dibakatur Roy 
on UnSplash.

Looking back at my fifty plus years of life as a cross dresser, I wonder when and how I crossed the gender barrier into being a transgender woman.

Also, how many years did I spend just going through the motion to arrive at my destination. I started with going through what I call now my mirror worship period. During this time, I couldn't wait for any opportunity I had to slip away from my boring, unwanted male life to slip into what feminine fashion and makeup I could find which fit me. Invariably, the mirror would give me positive feedback until I could come back for more. 

I am guessing now but I think approximately twenty years or so went by before I was brave enough to leave the mirror behind and see what if anything the world had to offer a novice cross dresser. On the other hand,  I know it took me longer than the two decades to figure out my truth. I was just going through the motions as a cross dresser and my gender issues ran much more deeper than just wanting to put on a dress and walk in front of the mirror. After years and years of doing the same thing, for some reason something clicked in me which made sense but at the same time was very scary.

It was the time I decided to find out if I could go co-exist with a group of women as a woman in their own territory. Previously, I had scouted out the venue I wanted to go to and when I wanted to try out my idea. It was the "Friday's" I write about often and yes I was petrified for several reasons. What if I did not make it and was ridiculed or maybe worse yet, what if I did and my life would change forever. If I did make it, I knew I could never go back to just going through the motions of being a part-time cross dresser. I was so much more. 

Finally, I got in so deep with me thinking I was transgender I reversed all of my gender thinking. Primarily I wasn't a man cross dressing as a woman at all I was a woman cross dressing as a man. Or, I was just going through the motions of being a male because I was born into it and was just attempting to get by until I could change my life for the better and live as a transgender woman. It represented a seismic change in my thinking on how I was going to live my life. 

By the time I was sixty, I could not take all the self destructive behavior I was experiencing any longer and decided to cross the gender frontier and live as a transgender woman. I embraced all my new gender thinking and set out to discover all I had missed by living my life as a man. Since my inner feminine soul had been observing my life and struggles the whole time, surprises were kept to a minimum. It turned out she was plotting all along how she would live once she got the chance. 

The last major step my male self gave her was going to the doctor and getting approved for gender affirming hormones. HRT just helped to further sync up what I thought I needed to be with what I actually was. Or, I thought I needed any help I could with femininizing my body to help me blend in with the world.

Of course, now I feel as if I was robbed of my life when I was going through the motions of being a man. On the other hand, I made the best of an unfortunate mistake. I gained a daughter, built a solid career and even survived my tour in the Army, so it all could have been so much worse as I battled my own gender dysphoria. It turned out, being transgender just led me into going through more motions than most people.   

Trans Peaks and Valleys

Image from the
Jessie Hart Archives.

Lifetime as a whole presents us with many peaks and valleys to negotiate.

Since I am transgender and always wanted to be a woman, my peaks and valleys often revolved around times when I came out as my authentic self in the world. Very early on, sadly, there were more frequent valleys than peaks as I learned to survive in the public as a novice cross dresser or transgender woman. I vividly remember too many times when I came home sobbing when I was laughed at. I don't remember now how I survived the dark times and continued to move forward. 

As I did move forward, there were other peaks in my life such as when my only child was born. When she arrived, my existence changed forever. Plus, I wondered how having a new person in the world would effect my gender desires. In many ways, I thought it was poetic justice when I had a girl. For some reason, deep down, I thought I could understand a girl better than a boy.  Since my daughter turned out the way she did, maybe I was right.

A big problem I had with my peaks and valleys was staying in one place long enough to actually understand if I was doing anything right. As I constantly changed jobs and moved my small family, I gave my second wife a hard way to go when I tried to chase myself. I am amazed we made it through twenty five years. 

Another problem I had was when I needed to come down off the gender peaks when I encountered them. Gender euphoria was so rare, I wanted to hang on to it as long as I could. When I couldn't I would become frustrated and ultimately mean around my family and co-workers. 

The more I progressed in my gender transition the more extreme the effort to climb out of the valleys became. The major problem was I didn't feel increasingly secure in my old male role and at the same time, I was feeling more and more natural as my femininized self. Which again caused me great frustration when I fell deeper into my valley. At several points I was so deep, I needed therapy to help me restore my mental health. Therapy on occasion did help me climb up to an acceptable level of a peak. When I was smart enough to actually take the therapist's advice. 

It turned out my fear of heights carried over to my transgender issues. The better I became at existing as a woman in public, I was scared. Primarily because for the first time in my life it seemed to be a real possibility I could reach my dream of actually living as a transgender woman. As I looked down on my previous male life, leaving it scared me. What would I do about  losing all of my white male privileges and then having to start all over again. At the time, the only female privilege I could see was a man opening a door for me. Which I later found to be false as there were other feminine benefits I had yet to experience as I climbed my gender peak. 

Finally, at the age of sixty, I could take the pressure of the climb no longer and I decided to stop all aspects of my old male life. I was taking gender affirming hormones to take me to the next step, my mental health was improving and for once I could see my life clearly as a transgender woman. So even though I needed to take a leap of faith off a cliff and transition, I found I had others around me who provided a soft landing. It turned out, I hadn't lost anything at all. 

My up and down life of trying to live as both binary genders was difficult at times to say the least. Near the end I found I made the correct decision on which peak to climb and it was not the male one.