Writing your Own Script

 

Image from Prophsee Journals
on UnSplash. 

I never found it easy to write my own script.

Sure, I could blame my gender issues on my problems but not all. I discovered very early in life I did not possess many of the dominate male traits to be a complete success as a man, so where was I to go. For example, I could not blame my lack of athletic prowess on my being a cross dresser. I was just not that good of an athlete. When I was on the football team, I wanted to be a cheerleader. They seemed to be having all the fun while I was getting beat up by a faster and stronger opponent.

Rather than setting out to write a new script as a cross dresser or young transgender girl, I internalized my script which turned out to be the worst move of all. I had nowhere to go or no one to turn to for help with writing my girl’s workbook. No sleepovers with other girls my age for ideas of how to be feminine.

I was stuck. I could not live either life I was in. I made a less than adequate male as well as a cross dresser who had nowhere to go in public. Plus, it would be years before I could go out of my closet and test the world. Once I did, I was very much a dismal failure. My earliest attempts at Halloween glory ended up with compliments on my legs but not much else, and the biggest problem was I needed to wait a whole other year before I could escape my gender closet again. I kept dropping my pen when I was trying to write. All I really knew was I was a male by default. Having been born into a gender I never liked.

On the rare nights I was able to escape and sample the public, often I could not read or follow the notes I had hastily scribbled down. And another problem I had was I was making a deep dive into being a transfeminine person so rarely, I could not remember what I was doing right or wrong. Even still, I did the best I could as I still obsessed with the brief moments of gender euphoria I experienced. Occasionally, I could see my gender dream was possible and I kept on writing. Chapters began to appear such as presenting as a woman with confidence and communicating with the world as a new me.

I was pleasantly surprised when I could read and react to the new chapters and attempt to keep them from invading my everyday life. It was impossible for me to walk around the majority of the time wondering how it would be to experience the world as a transgender woman. I was never good at self-control, and it was showing if I was not careful. Primarily with my wife who knew I was in my gender zone and resented it for the most part. She was too smart to listen to or believe my excuses about what I was really thinking about. As time moved onward, I became better at hiding my writing from her. Or so I thought. In reality, she saw our life slipping away to another woman (me) she could not control. In return, I resented her for being a strict feminine gatekeeper who would rarely let me behind her gender curtain by telling me I was not ready.

She was right. I was not ready at that time, but I was gaining fast regardless of her misgivings. In the midst of many ill-advised moves which jeopardized our long term, twenty-five-year marriage, I was making other moves which were proving I could make it to my lifelong dream of living as a transgender woman. More importantly, I was reading my writing clearly and the results felt so natural.

I also discovered writing your own script could be very messy and selfish to do. Many times, my wife and my male self-ganged up on me with fear tactics on what could happen if I transitioned. Many fights later, I finally prevailed by default when she unexpectedly passed away, leaving me alone with my writings. I cleaned up my mess and prepared to live out the rest of my life as a full-time transgender woman.

I think my lifetime of experience writing a new gender workbook for myself proved to be a worthy accomplishment. Once I understood where it was coming from. There was nothing wrong with me as I learned to navigate a new world I was just getting used too. It just took me awhile to catch up with the rest of the cisgender women who had a head start on me. I just achieved my womanhood from another path which is the topic of another blog post altogether.

 

 

Staring off The Cliff

 

Image from Anton Luk
on UnSplash 

When I reached a point where I saw the real possibility I could live a life of a transgender woman, I found myself staring off a deep gender cliff.

The biggest problem I had was wondering how I would land if I threw caution to the wind and become (as my second wife called it) man enough to be a woman. As I slid down the slippery slope towards my cliff, sometimes I was fearless and other times scared to death. I can’t tell you the number of times I sat in my car adjusting my hair and makeup before I went into a venue. At times, I considered bringing an oxygen tank along in case I hyper ventilated. I did not because I thought it would ruin my outfit.

Another problem I encountered was alcohol. When I drank, I became much more fearless but to get to my arrival, I needed to be brave and walk into a venue to order a drink. It took me awhile to put the alcohol in my rear-view mirror and get on with my life, but I did it.

Along the way, I cannot stress enough about all the bumps and bruises I had when I slid down a very slippery gender slope towards a very steep cliff. I was facing losing everything I knew, owned and loved to be a transgender woman, so I wanted to make sure I was doing my slide right. For the most part, I did good except for impromptu visits from the police after I used the rest room of my choice and another night when I was asked to leave a venue after I was doing absolutely nothing wrong. I mended faster than I thought I would and chalked the experiences up to what I needed to go through to transition in the straight world which I was trying out for the first time.

The main thing which kept me going was the deep feeling I had I was doing the right thing. I had spent too long in front of a lonely mirror to turn back then. I needed to face the cliff and decide how and when I was going to jump because it was becoming increasingly evident to me, I would need to.

After my second wife passed away, I went into another lonely dark period of my life when the only thing I did was go out in the world as a transfeminine person and watch the occasional sporting event with my brother as my old male self. What did happen was, I felt the time I was spending as a man was being increasingly wasted. Even my male self was seeing the beginning of the end to his life.  If my brother did not accept me (which he did not), he would have to go away.

What really helped me to overcome my fear of the gender cliff I was looking at, were the ciswomen friends I was developing. The give and take I felt when I was invited to girls’ nights out or even lesbian mixers was propelling me forward to making the ultimate choice in my life. Ultimately, I started gender affirming hormones under a doctor’s care and made my decision to jump off the cliff even easier to do.

It turned out, my women friends knew me better than I knew myself. They saw no traces of my old male self and helped me with the nuances of living in a feminine world. Many times, all I was doing was going along for the ride. Never had I ever experienced so much about a new world I desperately wanted to be a part of in my life. It all made my fear of jumping off my gender cliff so much easier.

Another example would be, I had taken the time to do my homework and build a solid base before the slippery slope claimed me. I waited for two extra years working at a job I hated to make sure I could retire on Social Security and not have to worry about transitioning on the job. During that time, my gender universe opened a little more when the Veterans Administration health care program I was in approved gender hormone therapy for veterans which gave me access to mental health care and cheaper medications.

It all turned out to be time well spent and came back to help me when I finally made the jump down my gender cliff. My experiences and friends made the landing so much easier. I ended up wondering why I had waited so long doing my preparation.

 

Unlearning LIfe

 

JJ Hart

Over time, I spent so much time and effort unleashing my male past, I cannot remember it all.

As soon as I could think about myself, I knew something was wrong. I just did not know what. Primarily, I did not know I was trying my best to survive in a male world I wanted very little to do with. Perhaps the biggest problem came when it was time to unlearn all the male life I was forced into. I was the proverbial round peg in the square hole, and I did not like it, even though I was rewarded with white male privilege when I was successful.

By choice or not, it seemed I was always fighting myself or the world for my gender dreams or goals. Very early I knew somehow, I wanted to be a woman someday, a deep dark secret I needed to keep to myself. Overall, I was deeply conflicted about where my life would end up because it seemed as if I was on a runaway gender train I could not get off.

A prime example was when I entered male puberty. I watched in shock as my body grew angles, and I needed to walk like a man. I am sure I was a comical sight, but I tried. I did not want to be referred to as a sissy and bullied in school and I was successful. Until it was time to reverse it all. When I left the cross-dressing mirror and entered the world as a novice transgender woman, there was so much to do as I was busy unlearning my male life. First of all, there was that male walk I needed to get rid of. There was no way I could overcome the positive feminine presentation I had succeeded at doing, if I was going to continue to walk like a man. Plus, I had the challenge of doing it in heels.

When I learned to walk in heels, I learned the inherent power of female privilege. Suddenly, my legs looked better, and men paid closer attention to the clicking of my heels. I just needed to match the rest of my fashion to blend in with my shoes. Since I loved my boots, the first thing that I did was try to save up for a pair of nice, heeled boots and find them in my size. Thank goodness for Payless Shoes. For the most part, I did good in my heels except for the time I got a heel stuck in a sidewalk crack in a mall I was walking in and the time I fell on a wet spot in one of my regular venues I was in. I survived and learned I needed to be more comfortable.

Another major gender response I needed to unlearn was to always look another woman in the eye when I talked to her, especially in bathroom situations. Eye to eye contact was normal in women’s rooms and totally not in men’s rooms. The new rules of the “room” I needed to unlearn and relearn if I was to survive as a transfeminine person.

Another major point of contention I write about often, is the difference between male and female aggression. I needed to unlearn the old male aggressive ways of coming right at you. On the other hand, I was clawed many times when I failed to recognize the passive aggressive intentions of a woman I was dealing with. Often behind that smile was a sharp pair of claws waiting to take a shot at my back. I needed to keep my head on a swivel and always be careful when I was dealing with other women in the girl’s sandbox. Lesson learned and I moved on as a better transgender woman.

Finally, all these lessons began to come together in my life, and I started to become a whole human being again. But this time, a human I wanted to be. No more unwanted male who I still needed to fall back on in times of duress. Afterall, I had to live with him for nearly fifty years, so there was some good to remember. I found I could relate to both binary genders better and understand where they were coming from. Of course, men were the simpler of the two genders as I suspected and women were more complex, and they led more layered lives.

None of it mattered to me as my world opened in ways I never imagined. Going to the extreme of unlearning my old life was radical but then again, I was able to make it work in my own way. If you are searching, just be aware everyone’s journey is different but maybe you can make it too if you are careful. There are huge inherent problems when you decide to forsake your male privileges and enter a new gender world.

 

 

Did I think Life Would Turn Out this Way

 

JJ Hart.

Did I think life would turn out to be this way, I would have said NO!

In the earliest days of just exploring my mom’s clothes and admiring myself in the mirror, I never thought life would have become as complex as it did. For years, I thought my cross-dressing urges were an innocent hobby which hurts no one. I was entertained and it was all that mattered in my selfish world.

Little did I know, all I was going through was just the beginning of my life I would have to adjust to if I was going to survive. I was embarking on what turned out to be a very unique life as I had the opportunity to live life in two of the main binary genders.

To put it all together on a timeline, I was in my thirties when I first read the term transgender for the first time, and I thought I had finally found a term which described me. Or, at least put words to my gender dream of possibly living a transfeminine life. Up to that point, I had only experienced the other gender variant people I met at various mixers I went to. When I attended the mixers, I met everyone from cross dressers in cowboy hats barely covering their masculinity all the way to impossibly feminine transgender women who were on their way to surgery. I certainly did not think the mixer I went to would turn out that way. I was expecting to attend, meet people like me and come away with new answers about myself. Of course, it did not turn out that way, and I came away with more questions than answers afterwards.

Primarily, I found myself on a sort of a gender balance beam. I was very clumsy and became well versed in playing both sides of the gender spectrum. At times I was good at my games and at times I was very bad, and I suffered. Through the bad times I needed to keep my eye on my gender dreams, be selfish and do the best I could. Perhaps the worst part was, I still did not know how any of it would turn out.

It was only when I managed to escape my dark, lonely gender closet and explore to learn if my future transgender dreams were possible at all. I was in a long-term marriage with a woman I loved, in a successful job and outwardly living a good male life. Why would I want to sacrifice any of the white male privileges I had earned. I did not think on occasion that I ever could.

What changed everything for me was the further I went on my journey, the more natural I felt. I began to think more about my life was meant to be this way. When I was selfish in my gender choices and I did my best to be a chameleon with my life. These days, I would be known as being gender fluid. Another term not known in those days, instead I thought of myself as an androgynous person. Especially when I started gender affirming hormones or HRT. What happened was, I really started to play with fire then. I had given myself a loose timetable until I made the final transition from male to female but could not keep it when the changes to my body became much more noticeable than I had ever imagined.

I never had thought in a million years, my life would turn out this way and I needed to arrive at a point where I needed to be selfish again and give up on my male self. My longer hair, softer skin and budding breasts were giving me away. It was time for a change. In fact, way past time for me to face the inevitable, I should have been living a transfeminine life all along.

All the torment and balancing acts I put myself through were no more than tormenting myself needlessly. Perhaps the final clue was how quickly my body took to the new feminine hormones. There was no negative to the process at all and the calm I suddenly felt led me to feel I was in the right place.

So, no, I never thought I would be in the spot I am in today. I am living as a transgender woman with a wife who supports me totally. The only slice of life I lost was my brother’s acceptance which was overcome by my daughter’s. It has been over a decade since I have spoken to him and truthfully, I haven’t missed our interaction. I am sure I had a few lucky breaks along the way, but for the most part, I think destiny was leading the way. Along with my stubbornness to continue my journey. It does not matter as it all worked out.

 

 

You Said What?

 

Image from Thomas Park
on UnSplash.

When your life is made up of a series of no, you can’t do that, you tend to find the nearest rock and crawl under it.

In my case, that no sent me into a deep dark gender closet I hid in for years. I even sought refuge behind the dresses and makeup I was wearing. Afterall, girls did not have to face the same challenges I was facing. I was too naïve to think the girls had separate gender challenges of their own to conquer.  It wasn’t until much later in life when I learned the truth from the women I was around about their life.

The word “no” ended up serving two purposes with me in my life. I found out relatively early that the people telling me no had any real control over me. An example was when I earned a spot-on American Forces Radio and Television when I was going into the Army during the Vietnam War. Being slotted into AFRTS was extremely rare and difficult to do and I did it with help from my congressman (back when they did anything). I learned there were ways around no if you were able to find them. I served my military duty but, in a manner, I wanted to.

My gender life was another subject altogether. I was still struggling and had a huge NO above my head for years. With a largely unsupportive family and no means to support myself as a transfeminine woman, I did not know what to do except to keep treading water and hope I did not sink. Plus, I had no money or insurance to cover any expenses incurred with gender surgeries of any sort. I was on my own and had to internalize my feelings.

Again, I found I could find my way around totally internalizing my feelings by attending local transgender-crossdresser parties where I could learn from others. In the meantime, I was doing my best to survive in a male world where I was becoming successful in. In other words, the rock I was under had more inhabitants than ever before but just as dark for me. Then I found a way to put electric light under my rock or in my closet. It was when I forced myself out into the world which was very unforgiving for years until I gained my footing and on a very slippery gender surface. It seemed my new high heels were more difficult to walk in than I ever imagined.

More than ever before, it was during this time, my gender tables began to turn for me. I was climbing a major mountain and still did not know how steep it was going to be. On the nights I was rejected by the public, I needed to go home and resolve myself to never take no for an answer. Somehow, someway I was doing something wrong and if I corrected it I could survive as a transgender woman. That was when I improved my fashion and makeup, along with losing nearly fifty pounds. All the improvements to my feminine presentation along with having the chance to communicate one on one with cisgender women I met, helped me to ignore the no button and keep moving up my gender path. I even was internalizing less.

Through it all, I need to point out, most of my progress towards being a transfeminine woman was not easy and hard earned. There were still too many, one step forward and two steps back moments to mention. At times, it seemed I was destined to learn everything a cisgender woman knew about life before I would be allowed behind the gender curtain and be invited to girls’ night outs etc. The only regret I ever had was never being invited to a bridal shower or bachelorette party. But it never happened.

Since I often learned the hard way what no meant to me in my life, I sometimes feel as if I am the worst person in the world to be writing about it. Sometimes no does mean no when you find yourself in a dangerous situation and you don’t have your old male personal safety privilege to fall back on. You must take the good with the bad when you are a transgender woman. Especially today with the current anti-transgender political climate. The republicans are not letting up at all with their gender lies, at least here in Ohio where I live and it is disgusting.

The more I see of their lies, the more I am resolved to never say I give up and keep on fighting for the truth. A big NO to the gender bigots.

 

 

Emerging as Your True Self

 

Image from JC Gellidon 
on UnSplash. 

Emerging as your true self after a lifelong gender struggle is often very difficult.

It starts very early in life when you discover you are in the wrong place at the right time, or the right place at the wrong time. Whatever the case, your struggle to find yourself begins. In my case I began with explorations into my mom’s clothing which lasted until I could no longer fit into any of her clothes. If you had suggested to me my final emergence into the world would take as long as it did, I would not have believed you. It was a long journey until I finally took the transition step to live as a full-time transfeminine person at the age of sixty.

Some of you may ask why I waited so long or since I did, why couldn’t I just wait for it a little longer into my senior years. On the other hand, I felt if I did not do it then, I would never have the chance. So, I pulled the plug on my old male life and emerged new as a transgender woman. It was never easy, but I made it.

Others may ask why I never opted for any gender surgeries of any sort. I did not because I was on the borderline to being able to present well enough as a woman to get by and I did not have the insurance or the finances to do it. Plus, I was superstitious about having any operations on my body since to this day the only surgery I have ever done was getting my tonsils taken out. I decided to set my gender dysphoria aside and work with what I had or pass out of sheer willpower as a transgender woman friend once told me.

I can’t tell you how many times my willpower was challenged before I made it to the point of emergence in the world. The seemingly endless times I was sent home in tears when my cross-dressing plans went wrong. Fortunately, I was stubborn and kept on moving towards my dream of possibly living fulltime as a woman. I replaced my willpower with confidence since in most cases, I was following my path in the most difficult way possible, without the help of any facial feminization surgeries. For the most part, makeup art was my way around having no expensive, painful operations until I could begin gender affirming hormones.

For me, the hormones worked miracles inside and out. Outwardly, my skin softened along with my facial angles of manhood, and I could use less makeup. Also, on the plus side, my hair grew quickly and fully since I inherited no male pattern baldness which made wearing any sort of a wig a thing of the past for me. What really changed was my overall view of the world. Suddenly, my view softened as my senses heightened. I felt emotions such as I had never felt before, and I learned how women complained they were always cold (except during menopause) because I was in my second puberty and cold all the time.

During this time, emergence became a slippery slide for me. The HRT hormones were quickly making it impossible to go back to my male life because I did not want to. Why would I want to trade in all the work I put in to travel my long gender path for anything? I finally gave up on all the resistance I was putting into retaining any of a life as a male I never really wanted. The only remaining reason turned out to be me losing all the white male privileges I had worked so hard to gain. For that reason, I put off emerging and attempted to briefly live a portion of my life in both binary genders. Something I would strongly suggest not doing. For me, trying it wrecked my mental health and nearly my life. My male side was hanging on and very materialistic while my female side was discovering a magical life is the best way I can describe it. Afterall, I could see my best-case dream life within reach.

Through it all, I think being approved by a doctor for gender affirming hormones was the biggest moment of my emergence as a fulltime transgender woman. With the help, I was able to carve out a new life and put the old one aside. I was able to see a new world with the help of new friends who never knew the old me. The essence of emergence when someone else could enjoy the company of my new feminine self. HRT was just a kick start to make it to where I wanted to be. I needed to take it from there and make my emergence complete.

 

 

 

The Second Act

 

JJ Hart doing Trans Wellness Outreach. 

Will the second act of life be better and more successful than the first? How many people even get a second chance?

That is the question I needed to answer when I finally shed my male life and entered a transfeminine existence. Since I did it at the age of sixty, I have had plenty of ground to catch up with. Many times, it seemed I never would. My internal gender clock was moving one step forward and two steps back as I attempted to transition. I had times when the picture was clear in my mind, and I was able to put it into motion. Such as the night I took myself out to see a major Christmas light display in a nearby village and was warmly accepted in my soft bulky sweater, leggings and boots. Then, as I rode the wave of gender dysphoria, I would do something wrong such as how I was moving. I am fond of saying, I looked like a linebacker in drag.

The problem was, if I relaxed at all going into the second act of my life, I had the tendency to fall back into old habits. I was learning the hard way over and over, to take nothing for granted in my new life. Many times, I tried and failed not to be too hard on myself since I was making up for a first act in my life which lasted so long, and I had to concentrate so much on it just to survive. It was around this time when my male self really began to set up roadblocks on my gender path. Suddenly, he began to see that this road I was on was not a phase or joke and I was deadly serious.  He started to ask questions such as how I was going to live in my second act with no job and how I was prepared to do it without the wife I dearly loved and had been married to for nearly twenty-five years. To be sure, all very real and very scary questions.

I put off deciding my life as long as I could as I attempted to learn if I could really live a transfeminine life at all. Were the obstacles insurmountable or not. Through it all, the one overriding feeling which kept me searching was the deep down feeling I was doing the right thing. I was headed in the direction I should have been going in my life all along and I kept going through the ups and downs of transitioning into my second act.

Once it was clear I was successfully transitioning into my second act, I needed to make sure I was doing it correctly. It turned out I had all the help I needed. In addition to the cisgender women I always mention, there was one important person I don’t mention enough. That person turned out to be very real and important to me. She was my inner feminine person who had been waiting for all those years and decades for her chance to fully come out into the world. Once she finally did, she knew completely what to do and what was ahead for my second act of my life. Mainly, all the nuances of life as a woman if I really wanted to go there. She knew the best part of my life was yet to come.

More importantly, I had finally made it through the bleak years when often I thought there would be no tomorrow. Or at least my dream of living a feminine life would never be realized. Often it set off a series of insecurities in myself which set back my life. Act one was bleeding because I could not get to act two.

When I finally made it to my second act, it was as if I had lifted a heavy weight off my shoulders, and I came to a point where I needed to be more understanding and approachable in the world. I could not get away with the old male ways of internalizing my feelings and start living again. If I did try to hide as a transgender woman, I would never have a chance to provide myself with a positive outlook to other women and not come off as an unfriendly transfeminine woman which was the last thing I wanted or was.

Since I was one of the few humans who ever had the chance to stop their life and begin again so there was no way I could mess it up. I needed to enjoy life and live it the best I could.  

Build the Plane before You Fly It.

 

Image from Miquel Angel
Hernadez on UnSplash. 

Early in my life I learned to build my gender plane before I tried to fly it.

When I was simply admiring myself in the mirror, life was easy, or so I thought. I could apply my makeup and put on my mini-skirt and journey to the mailbox, hoping the neighbors would not see me. Through it all, the mirror lied to me and said I looked wonderful even though I did not even have a wig. Even still, I kept going. Mainly because we lived in a very rural area and no one saw my mailbox adventures.

I suppose, during those days, I was merely experimenting with clothes and makeup, the same way any other young girl would do. The problem was, I had no one in my peer group to criticize me and help me to learn what was correct with make-up and fashion and it showed. I was attempting to fly my gender plane before it was fully built. The mirror never did any of it for me. It was simply there to tell me how good I looked.

It was not till much later in life, did I begin to replace the mirror with public feedback when it came to early adventures going out in the world as a transfeminine woman. I vividly remember all the nights I quickly returned home wiping the tears away after being followed by someone and laughed at. Mainly from teenaged girls. Somehow, I needed to keep taking my plane back to the drawing board to attempt to see what I was doing wrong. The good news is, I did begin to figure it out. I was dressing for the wrong gender. Trying to please men, when I should have been trying to please women. Out went the sleazy, ill-fitting clothes. Replaced by more sensible clothes as I did my best to cover my male poisoned body.

It worked as I began to blend into the world, as I gave myself the chance to experience my reality for a change. I was similar to the Wright Brothers during their first flights; I was not going far but I was doing it. During this time, my flights grew dramatically longer. I was finding my way out of the clothing stores where all they cared about was my money, all the way into restaurants where I had to interact with staff on a one-on-one basis. I was discovering how well my plane was built or not. Surely, I was still experiencing my ups and downs, but I was having more of the positive side of life.

The problem was, on my male side, he was still having success in his world with a very successful job. So, he wanted no part of helping to build a new gender plane. I was forced to build around him. Which made for a very shaky foundation. Especially for my already frail mental health. It hurt me deeply when I was flying high and he brought me back to earth with a crash. He even took me as far as an ill-fated suicide attempt.

In the short, and long term, I survived him and continued to build my plane, every time I thought I was done, there was more to do as I studied the nuances of living a transfeminine life. Adjusting to being passive aggressive alone to other women was a big adjustment, not to mention the communication issues I faced in the new world I was in. Other women were very curious about me and wanted to know what I was doing in their world. Very soon, my air space became very crowded with new people, mostly all women.

Many times, starting all over in life became a major challenge for me. I needed my plane to provide me with a better view of what was really happening in my life. I had too many fake, mean people to beware of. Even after all these years, my plane was still very fragile. Before I moved ahead any further, I just had to build in the inner strength I needed to pursue my dream of living fulltime as a transgender woman.

To accomplish my dream, I needed the friends I had found in my new life to do it. I always mention the Liz’s, Kim’s and Nicki’s of the world who helped more than they ever knew. It was all of them who finished building my plane more than I did and I will be forever grateful for them coming together to save me.

Growing up, I built plenty of model cars to look at and even race, but nothing helped me to prepare for the greatest building experience of my life. A gender transformation project which took me decades to complete. In fact, I am still working on it to this day even though I have been fully out for over a decade now. There was more building than I ever thought possible to start all over again with my life.

 

Painting a Picture

 

Image from Vinicus Amix
Amano on UnSplash.

During my life, I have never been accused of being an artist. In fact, I would mess up drawing stick figures.

The best thing I could do was connect dots. Which I needed to do quite often in my gender conflicted life. Basically, the main dots I needed to connect were, was I a boy or a girl. It ended up taking me far too long to finally connect those dots and attempt to draw my gender picture.

When I began to experiment with makeup, I learned the basics of facial artwork and even I could make myself look better in the mirror. Mainly, though, I struggled along until I summoned the courage to request a makeover from a professional makeup person at one of the transgender-cross dresser mixers I went to. He did a miracle job and transformed me into a woman who I only had dreamed of. Most importantly, he was able to explain to me what he was doing in a step-by-step format that even I could understand. I looked so good, I was invited along by the “A” listers, as I called them when they went out to explore other venues after the mixer was over. I even got the last laugh over all of them when a man tried to pick me up in a venue we were in, and they were not.

Sadly, the success I felt from the mixer did not last long when I had to go back to the real world, I was a part of. When I did, I became mean and nasty to my wife and others around me. All the way to almost losing jobs because of my attitude. No way to paint a picture. Somehow, I needed to get better before I self-destructed my life.

I hung on until I did get better when I had the chance to leave my closet more than once a year for Halloween parties. I was aided by the fact that my artwork with makeup and clothes continued to improve until I looked better than some sort of a circus clown in drag. I simply had to if I was ever going to have the chance to live my dream. Through it all, it did occur to me how difficult the process was going to be. I was painting two pictures at the same time, one as a transfeminine woman. One as a successful man. The stress of doing so nearly killed me. Being a man was easier because of all the white male privileges I had gained but being a transfeminine woman felt so exciting and natural when I painted her.

By the time I had gotten this far, I found I had painted myself in a corner. I could see the finish line for a change, while at the same time, I had a wife I loved, a family I loved and a good job to protect as a man. Decisions, decisions were wearing me down. Primarily because it was so frustrating to me to have worked so hard throughout my life to paint two pictures, only to have to finally choose between the two. What I did was let the public choose which picture they preferred. Since my transgender woman had an unfair advantage, she won the contest easily. She got to start all over again and learn from all the mistakes her male counterpart made and go from there. Time and time again, the public picked her.

Putting the finishing touches on my feminine portrait proved to be easier said than done. First, I needed to come out of my closet to what was left of my blood family. I received a 50/50 reception when I was accepted by my daughter and rejected by my brother. By this time both of my parents were deceased. Predictably, both coming out events were scary and quickly resolved. My daughter wondered why she was the last to know while my brother did not have the courage to stand up for me to the rest of his extended family. We have not spoken now in over a decade. Sad but true, he never wanted to see my finished portrait. Conversely, my daughter and I are closer than ever.

But then again, are our portraits ever finished until we die. Shouldn’t we always be making small upgrades the best we can? Plus, age should put us in a better position to do it. Sure, painting two completely different gender portraits at the same time was difficult and at times required tons of skill to keep one hidden. But somehow, I was able to gain the artistic skill to make it happen.

The powerful draw of an overwhelming dream was all the motivation I needed to become a better artist and provide the background I needed to live a life as a transgender woman.

The Big Risk

 

Image from Joshua Rawson Harris
on UnSplash.

When you jump from one of the main binary genders to the other. In my case of course it meant leaving all my hard-earned male privileges behind and move into a largely unknown world.

The risk was tremendous the farther I went along. Mainly because I was accumulating an increasingly amount of male baggage. Such as family, house and good job. At the same time, I was perfecting my transfeminine appearance, which encouraged me to move forward in the world. To be sure, I was involved in being tested with a double-edged sword. Or which way should I go? I spent many wasted hours trying to obsess over my future, which was still very vague. At that point I did not even know if I could even exist in a fully transfeminine world. On nights I was accepted by the public, gender euphoria told me I could. Then, on the nights I was rejected by the public, I thought there was no way I could ever live my dream, and it would remain just that…a dream. A dream which never would go away. 

Through it all, the idea of risking all my existence remained with me and naturally scared me to my bones. I was hiding away my biggest secret and even though I did internalize it well, it was a drain on my mental health. Which is a side story I tell often because it is something I think more transgender women and trans men can learn from. At least I hope so.

Something else, I don’t think the average person understands about us, is this is not a casual joke to us, and we just cannot stop putting on a dress on a whim. We are ready to risk it all to live an authentic life as our true selves. Free from our closets. The problem was at the end of a day out, most of us must go back to our old unwanted male selves (or female selves for trans men). For me, it was always a heart-breaking experience as I tried desperately to maintain my male façade for my wife and work.  The only alternative I had was to attempt to live part of my life as a trans woman and the other half as a macho man. It tore me up.

The entire process just became worse and worse when I began to carve out an all-new life in a feminine world. The more success I felt, the less I wanted to go back to my old life and began to research the prospect of living my lifetime dream. In fact, all I can remember all I really wanted to be when I was young was, I wanted to be a woman. Which of course, I needed to keep to myself. I was miserable as I felt as if I was the only boy in the world who felt that way. It took me years to learn I was not the only male in the world who wanted to be female and was prepared to take the risk to do it.

I was able to find a couple of real live acquaintances who took the risk, almost, so I could judge what it meant for me if I decided to follow in their footsteps. I say almost because one the transsexual women I knew was a very attractive retired firefighter in Columbus, Ohio and had a very good pension to live on. The other trans woman I knew was even more attractive in her own right and a very accomplished electrical engineer and would always find a job. I had a good job but not one which would carry over to a gender transition. So, I had much more to consider, not to mention neither of the women I mentioned were in a serious spousal relationship and I was. Right in the middle of a twenty-five-year marriage. I would later come to know how similar yet drastically different our transgender community is.

The pressure I was feeling to take the final risk continued to build. Aided by the success I was having in dealing with the public, I was encouraged to take the final risk in my life. At this point, destiny stepped in to show me the way. My two major stopping points were my second wife and what I would do for an income after I transitioned.

My wife tragically died, leaving me with one to speak of to object to me leaving my old life behind and beginning a new one. Then, by that time, I was in reach of being able to retire on early Social Security income plus what I could sell online. In many ways, the lightning did come right before the rain for me and then the sun came out. When it did, I could see my dream life had arrived and I could live how I wanted to.

 

 

 

Jumping Through Hoops

 

Image from Jennifer Mela444
on UnSplash. 

The more involved I became in the transfeminine world, the more I found myself jumping through hoops. Many times, in my heels.

It seemed, every time I became comfortable enough in my transgender womanhood, something would come along to set me back. Sadly, most of my setbacks came at the hands of my deceased second wife. She was accepting me as a cross dresser but recoiled and drew a line in the sand when it came to any idea, I was transgender and wanted to move forward to gender affirming hormones. As much as I wanted to argue (or plead) my case, she still said she did not want to be married to a woman.

It was my fault I did not have the courage to tell her she already was married to a woman. Like it or not. So, since I lacked the courage to follow my gender instincts, I did the worst possible thing and tried to hide all my activities such as leaving the house dressed as a woman. One of the things I promised I would never do. But, as hard as I tried to hide it, she always would somehow catch me coming home when I was cutting my time away too closely. To save what was left of our twenty-five-year marriage, I went as far as seeking therapy. I went to therapy mainly to provide my wife with an idea I was jumping through another hoop to save our relationship.

I have therapy to thank for helping me to strengthen my mental health, but my wife never knew it was not helping our marriage. In fact, one therapist even told me she could do nothing about my desire to be a woman at all. Leaving me with no hoop to jump through at all, and I would have to find another way. In the meantime, I knew just sitting around the house admiring myself in the mirror was not going to cut it in any way. Once I had jumped the hoop and was successful in the public’s eye, there was no way I could ever go back to my old life.

Deep down I knew, I had to keep pushing forward as I set gender goals for myself such as taking the giant step of leaving the gay bars and seeing if I could be accepted in sports bars. When I found out I could, I was ecstatic and kept on going. However, through it all, jumping through hoops was never easy as I kept on doing stupid things such as overextending the water-balloon breast forms I made in my pre-silicone days. Of course, I had one of them break and created a mini flood at one venue I was a regular in. As I said, I needed to very quickly upgrade to silicone breast forms to prevent any future disasters. I had enough other problems to worry about. Such as, what was the new person I was creating be like.

Suddenly, I was beginning to understand when my wife called me the pretty, pretty princess and told me being a woman was more than just looking like one. Most importantly, I was in the middle of learning exactly what she told me. When I was going to my venues and socializing as a transgender woman, I was jumping all the hoops I needed to get by. More precisely, I was learning the layered life a woman lives when men think they are running the show. On more than a few nights, I became so tired of jumping hoops, I just gave up and headed home exhausted.  Along the way, I was facing passive aggression from ciswomen who really resented my presence at all. I learned to leave the other women behind and move on to people who at the least did not dislike me. Life was too short to waste it on bigots and haters.

Tragically, my wife passed away before she was around to meet the new and improved me. It would have been interesting to see if she recognized I took her up on her advice. I tool a crash course on her instructions that a woman was far more than appearance. My period of exploration was intense and to the point and I could deflect my future any longer. I needed to take it upon myself to finally achieve my lifelong dream of living a transfeminine life.

My hoops became so much more real than the earrings I was wearing. I was finally in the process of paying my dues my wife had talked about. What she never told me was, I would have to be allowed behind the feminine gender curtains to really could do it. One led to the other and while it was never easy, similar to jumping all the hoops I needed to jump, I made it. Heels and all.

 

Making Gender Decisions

 

JJ Hart

Living my truth as a novice transgender woman proved to be more than I bargained for.

Like many of you, I started innocently enough as I rummaged through my mom’s clothes for anything I thought would fit me. Too soon, I found I had fallen in love with the feel of feminine clothes such as undergarments and panty hose. The biggest problem I quickly encountered was the buzz I felt when I cross dressed in front of the mirror just did not last. In the space of a couple days, I yearned to repeat the process of doing my best to look like a girl, repeatedly. I did not know it then, but my mind was attempting to tell me I was transgender and not a cross dresser. In those days, the transgender word was years away from being used or understood.

When I finally reached the age to go out on my own, the mirror remained my best friend. All the way to the point of going places where I could enjoy seeing my transfeminine reflection. I would even go to the big home improvement stores to check out their mirror selection when in fact, I was checking me out and reinforcing my feminine image in my mind. Finally, even my simple search for gender acceptance proved to be too much to take on a regular basis. I needed the public to be my reflection which mattered the most. Or I began to interact with more clerks and servers on a one-on-one basis to see their reactions. The more I explored, the more confident I became, and life became so much easier. In fact, too easy.

The first main discovery I made was the fact that women were much more interested in me than men. It did not matter, if the woman was a clerk, a server or a stranger off the street, they all seemed to share a curiosity of why I was in their world. Many times, there was too much curiosity going around on both sides, I was as curious about them as they were about me. It was about this time when I began to really live my truth as a transgender woman. I always reasoned too, more than a few strangers were drawn to me for that precise reason. They knew I was living my truth. Certainly, there were haters and bigots along the way, but not enough to slow me down. I ended up learning to stay clear of them very effectively.

Confidence was always my key as I learned to live my truth. I knew I was transgender and anyone who paid close attention at all to me, knew I was also. With that out of the way, we could get down to real life and very soon the typical stranger realized I was not the normal cross-dresser they saw on television on one of the many talk shows. I was real and not evil in any way. It worked with other women I encountered and almost never did with any men. So, I was satisfied with my results. I was kicked out of the men’s club and that was the way I wanted it. I guess you could say I was in some sort of a new layered gender reality as I tried to live my new truth.

I would be remiss if I did not bring up how intensely difficult all of this was to the progress of my mental health therapy. Per norm, my therapist said it best when she told me there was nothing, she could do about my wanting to be transfeminine. If I wanted to enough, I would make the sacrifice to do it. All my visits were pointless until I faced my own gender reality. My excuse continued to be, leaving my male life with all the comforts of the privilege I had built up was very risky, so I continued to put it off until it was almost too late and I tried suicide as a solution.

Naturally, the attempt did not work, because I am here writing attempting to help others with similar gender issues as mine. I learned I wanted to live and needed to make the right choice with my life to do it. I was stubborn and waited until the age of sixty to make the change from living a partial male life to a full time female one. All the lessons I absorbed along my long gender journey came back to help me in my final decision. I still remember vividly, when I sat alone and decided to donate all my male clothes to thrift stores and give up my male life forever. A tremendous weight immediately came off my shoulders and I knew I had made the right decision.

 

 

 

 

Riding the Gender Merry go Round

 

Image from Stanley Kustamen 
on UnSplash. 

Catching the gender merry go round when it was in mid-spin was never easy. As I always point out, I had no workbook on how to achieve my feminine desires that were available to me.

I often wondered what magical experiences were available to the girls around me but were off limits to me. What did the girls really learn about being feminine from each other? Was makeup one of them? I was jealous because I had none of the early basics of applying makeup. The closest I came when I was painting the model cars I had. I never was very good at skillfully painting cars, so I wondered how I would ever be good at painting myself. Enamored, I remember watching my mom apply her makeup as I looked for any small hints I could follow but I never seemed to learn.

Of course, there was much more to jumping on a spinning merry go round than just skillfully applying makeup. There were clothes to worry about too, and how could I afford them on the very limited budget I was on. I resorted to taking any small jobs I could as a kid to augment the meager allowance I received at home. In fact, my major source of income was a neighborhood newspaper route I took on. When I added all my funds up, I usually had enough money to buy my own makeup, panty hose and other rare items such as a pair of shoes I was lucky to find.

Once I was able to be confident in my ability to jump on the merry go round, then I needed to worry about hanging on. In the early days of my public explorations, I was having a very difficult time presenting well at all and I often was laughed at by others on the merry go round until I began to learn what I was doing wrong, and I could fill out my feminizing presentation workbook. It was a win for me when I could quit using crayons on my face and use them to color my workbook, I was less and less a clown in drag, and more and more an androgynous person for the public to judge my gender. For once, I could rightfully claim my seat along others on the merry go round because I had earned my spot as much as they did.

After a while, the spinning became too much for me and challenged my fragile mental health. The biggest problem I had was my refusal to face myself and my innermost truth. I was never a man cross dressing as a woman; I was a woman cross dressing as a man my entire life. The basic thought of who I really was consumed all my spare thinking. I am amazed now how much I still accomplished in my life as I suffered my mental duress. At times, it seemed my merry go round was spinning completely out of control. Plus, at the same time, I kept accumulating extra male lifetime baggage I did not really want. Sadly, the life I was living kept me from making very many close friends because I just thought I was knowing them under some sort of false pretense. I wasn’t the man they saw before them; I was a fake. Which I hated and added to my problems.

I finally came to the point where I needed to either slow down my merry go round or get off altogether. I just couldn't take it any longer. I certainly was not getting any prizes for putting myself through the anguish of staying on. I had given my ride the best shot I could, and I needed to grow in my transgender womanhood. I had tried my best to outrun and out drink my gender issues, and it was time to face the reality of who I was.

When my merry go round glided to a stop and I was able to look ahead to the new life I was about to enter. I was excited to see and live my feminine reality. I had filled out my workbook and paid my dues and was ready to go. The next time I was at an amusement park I could really enjoy the experience as a transgender woman. If anyone in the world did not like it or approve of me, I didn’t care. I had spent a major portion of my life thinking I was in the wrong. When in fact, the bigots were the ones in the wrong and they were the riders who needed to get off the merry go round first.

Gender Participation Trophies

 

Image from Vicktor Forgacs
on UnSplash

In the gender world, there are very few participation trophies available to anyone for simply showing up. But are there?

Early on, before I decided to allow the public to award me participation trophies, I let the mirror do it and they were always right. I was an attractive girl when I wanted to be and there was a trophy for me to hide away with my belongings, or at least for me to mentally hide away from prying eyes.

In the meantime, my male self was attempting to win as many trophies as he could because he was not very good at athletics or whatever else he was trying. As hard as he was trying, total success seemed to always evade him. What happened was, both my binary genders experienced deep frustration, and I felt less as a person.

It was not until much later that I began to be successful and win a few participation trophies, specifically as a transgender woman. Her success though just created more problems for me as he feared she would take over completely, and what would become of all his hard-earned male privileges. There was a life at stake and could not be taken lightly. No cheap shiny participation trophies to proudly place on the gender shelf of life.

After I had learned the basics of blending myself into the world as a woman, I needed to be careful of the trophies which were being presented to me. I learned the hard way; not all women were forthcoming in their friendship and acceptance in their world. Many days with other ciswomen in the world. I thought I had won a participation trophy, only to have it passive aggressively pulled away. Quickly, I learned to be more careful. Life just wasn’t as easy for me when I had left the male world I was used to, and all aggressiveness was a frontal blow you could prepare for or retreat from. As with everything else, my life as a transgender woman was going to be more difficult than I thought. There would be no more running home to the mirror to hide. If I wanted to obtain more gender trophies, I would need to journey farther and farther out of my gender closet to do it.

The first inkling I could came on the night when I was drinking with a group of single professional women at a nearby TGI Fridays venue. As the bar area quickly began to fill up with women, nobody said anything out of the way to me, and I felt as if I fit right in. As a woman. I had known in advance to dress professionally, which helped me to overcome the fear I felt. So, I fit right in. When I safely made it home that night before my second wife did and removed my makeup, I gave myself a participation trophy. Mainly because, I knew I had crossed a line I could never go back to. My cross-dressing desires were much more than just a simple, innocent past-time. I knew deep down I wanted more as I pursued my own transgender womanhood.

More meant going back to Fridays and establishing myself as a regular, as well as other nearby competing venues which were happy to serve me and take my money as a trans woman. For the most part, I was compiling more trophies than I could count as I did more than surviving in my new world, I thrived. I learned too how difficult I would have it, if I continued the gender path I was on. Now, each trophy was harder and harder to get because each time I received one, it seemed the stakes were higher and higher. I was risking my twenty-five-year marriage, my family, friends and job, and I deeply felt the pressure.

At some point, I knew I would have to decide to throw out all my old male trophies and move on, but I was afraid to do it. I compared it to looking down at a steep gender cliff and wondering what would happen when and if I fell. All the trophies in the world would not save me but only real-world friends would.

Fortunately, I had those friends who had found and accepted me and made my gender landing very soft. In essence, all those new friends were initially trophies I cherished completely. They turned into the real thing over time, and I was able to carve out a life. Then I could throw out all my female trophies for good and live a realistic, genuine life as a transgender woman. My trophies became as fake to me as most of the people I met along the way, and I was able to throw them all away.

 

 

Self-Destruction

Image from Abbot on
UnSplash.

I was very self-destructive over the years, and I am frankly amazed I made it to the age of seventy-five in one piece.

I think my self-destructive behavior began when I was forced into a gender mold which was deeply foreign to me. When I was very young, I did not know exactly what was wrong, but something certainly was. I was somewhat older when I had my first inkling of having a condition I barely knew how to pronounce. I was gender dysphoric. As a teenager, many mornings when I woke up for the day, I did not know if I was a boy or a girl. Not a good place to be.

My first object of destruction was the car. With it, I found I could seriously injure myself and sadly others. I could race my brother with a car and go way too fast at night for the road conditions. Many nights when I came home late and lonely, my mom was waiting up and, on several occasions, told me the angel riding with me was my grandmother. She may have been right, when I wrecked one of my cars going too fast and ended up rolling it several times into a house. Very easily, I could have been killed, along with my brother. But my brother and I walked away without a scratch. Even though the car was totaled.

I was just reckless as I entered my military years as I was frustrated and lonely as I grasped at any straw to solve my gender issues. Never pausing to realize the answer I was seeking was as close facing my own inner self. For more years than I like to admit, I feared facing the truth about myself and stayed on my self-destructive path. That made two paths I was on. One on my gender issues and the other me trying to hurt myself.

To dull the pain, I resorted to self-medication with alcohol. Drinking vast amounts of beer helped me to forget my male self on one hand and made me too brave on the other hand. On nights I drank, I could see one path from the other. So, I went back time and time again.

Then, my time in the military just made my habit worse as I was in an atmosphere of supported alcohol abuse. I found I had to finally rid myself of my destructive ways when I hit rock bottom and attempted suicide. Simply, I was tired of fighting my overwhelming desire to be a transgender woman and the possibility of hurting the loved ones around me. Most importantly, I felt as if the world would be a better place without me.

Once again, my guiding angel was with me as I failed in my suicide attempt with pills and booze. Maybe it was her who finally convinced me to face my gender truth. I was born into the world as a male which was completely wrong. My vibrations were always female deep down inside and those vibes were deeply felt. Still my male self-refused to give up all the privilege he would lose and did his best to stay the course he was on. All he did was to prolong the certainty of my life. When he gave up and I could pursue the deepest truth of my life, I committed myself to moving forward into my transgender womanhood.  

With commitment came a deep-down of satisfaction and happiness I had never known in my life. I was fond of blaming my parents for the lack of happiness I experienced when I was growing up. When, in fact it was me who was at fault. I was not honest with myself, and it hurt me. I couldn't follow my dreams, and it hurt me. The deepest cut of all came with the dishonesty I felt. I was raised to be honest, and chasing my gender dreams curtailed my honesty with the world when I was busy hiding all the time. Perhaps, most frustrating of all came when I could not outrun my issues. First, I attempted to pass myself off to me as a harmless cross dresser and, when that did not work, I faced the possibility I was transgender. A big leap for my honesty.

It was the first time in my life; I could face my truth and live honestly as myself. With new women friends and my wife Liz pushing me on, I was able to restore my confidence as a woman as never before. My progress was so much more than my appearance and reached deeply into living a fulltime life as a transgender woman. My gender journey of a thousand miles did begin with a single step and I took mine.

Sometimes I wish I had made the journey sooner but then again, all of us only have one life to live and I was able to live mine.

 

 

 

Gender Selfishness

 

JJ Hart, Key Largo, Florida.

Often as I discovered my transgender womanhood, I felt extremely selfish. Who was I to sacrifice my male life with others just to cross dress in the mirror for me.

At the time, I regarded myself as a clown in drag and ugly in every way possible. With those thoughts, how could I even think I could succeed of my dream of living as a woman someday. To have any success at all, I needed to be selfish and forge a one-way path to feminize myself.  

Defining selfishness was a problem also. I went from thinking I was merely in a phase, all the way to finally realizing I was a full-fledged transgender woman. Along with all the responsibilities of living a new life. I needed to face the reality of knowing every step I took would be different and others close to me would have to come along for the ride. Or be left behind. Mainly, I am referring to my second wife, who for several reasons drew the line at helping me femininize myself. The number one reason was one I had to totally agree with, which was she did not want to live with another woman and specifically one she did not like.

Through it all, I tried to discover why she did not like me. Since she has long since passed away, I can’t ask her for an honest answer. My best guess is she did not the amount of makeup I wore and the wardrobe I had acquired. Plus, she especially hated the idea of me leaving the house cross dressed as a woman anytime she was not around. Essentially, I was cheating on her with myself. I was the other woman. Naturally, I was torn too, as I just could not stop exploring the new world, I was excited to find myself in. All my efforts just put me in the cross hairs of my mental health. I was selfish and put myself in risk of losing a marriage of twenty-five years and give up the chance of living my dream of living as a woman. These days I make no secret of trying to take my own life with an ill-advised suicide attempt. I thought there was only one person who could truly help me, and I had burned that bridge with her. So, I was trapped.

Fortunately, with the help of a good therapist, I found my way out of the darkness I was in, and she helped me to understand the gender situation I was in. I started to take it for granted I was selfish, but I had to be to save myself and my mental health. At that point, I knew I would not have wished the period of life I just had went through on my worst enemy. My dark closet was even becoming darker even though I was beginning to explore the world as a woman. Transgender, or not because often gender borders were blurred. To focus on it, I needed to be more and more selfish in my life and every spare moment and thought had to be involved in feminization.

By this time in my life, my biggest hurdle was overcoming the loss of my second wife. Sure, she resisted losing me to another woman, but I still loved her dearly, and we did have many good times together. What happened was my long ignored inner female stepped in and immediately took over. She exposed us to many new social interactions to see what would happen and if when we conquered it, we immediately moved on to often more delicate social situations. She was really into testing me to learn how serious I was about the transition I was considering.

One of the main tests was when we decided to seek out gender affirming hormones. To do it back in those pre–Veterans Administration days, I needed to find a doctor to approve me. It was not given since I was nearly sixty at the time and had to have a health exam before I was given permission. I was approved for a minimum dose and soon was allowed to pursue a life changing hormonal program. Overall, the hormones turned out of be a wonderful gift to my inner self and allowed her to sync up her old male external male self with her strong feminine self to make a more complete human being for the first time in my life.

It turned out, my life of being selfish was the only way I could escape the male life I was born into. It was amazing how quickly my mental health recovered and for the first time in my life, I felt happy. The weight taken off my shoulders was amazing.

 

Coming Home

 

JJ Hart (Center) Wife Liz on Left, 
Daughter on Right. 

The process of crossing the gender border from male to female, always felt as if I was coming home.

From the beginning, my dual genders clashed, causing me to often sacrifice my already fragile mental illness when I was diagnosed as being bi-polar. Naturally, it was difficult to separate one issue from another when I became depressed and just wanted to curl up in a ball and left alone. On most occasions, I could just cross dress in front of the mirror and take my mind temporarily off my trip to find my true home.

The trip proved to be much longer than I ever thought it would. I never considered it would take me on a fifty-year odyssey. Complete with too many blind curves and dead ends to mention. If I was to attempt to mention any of the major problems I had with my transition was there would be so many more transitions than one. The gender border crossing was so complex, it would take me several different ways at once. I finally came to the point where I was simply trying to raise the bar of living as a transgender woman every time I went out in public. In my earliest days, it meant concentrating on more than just my feminized appearance. I needed to put my appearance, no matter how good or bad, into motion. What good would it be to look like an attractive woman if I was moving like a linebacker.

Every time I made a move forward in my transition, I could imagine myself living my gender dream. Which in most cases scared me more than anything else. What would my life be like without all the male privilege I worked so hard to earn. Perhaps the only stable idea I learned was I was much more than the casual cross dresser who just wanted to put on a dress for certain occasions. As suspected from my earliest days of admiring myself in the mirror as a girl. I wanted to do much more such as be a girl or at the least find out if the public would accept me as one.

I put many hours of work into my femininized presentation. I tried and tried to get my makeup right, even to the point of losing nearly fifty pounds on a diet I undertook. When I lost weight, I was able to fit into my stylish clothes, so it was a huge win for me. Along with the intense skin care routine I followed. Suddenly, I discovered I could use less make up and prove less was more. All these moves proved coming home indeed may be reality if I kept working hard enough. For the first time in my life, I made a concerted effort to achieve a very real goal. My transgender womanhood.

As I said, coming home involved several other minor and major transitions. I began to do so called womanly duties such as grocery shopping into my days when I could. I also added gift shopping at Christmas (and other times) to my time as a woman. Through it all, I was learning how the world would possibly accept me when I was able to make it home. All these actions showed me the feasibility of proceeding with my gender plans, though many questions remained unanswered.  Such as, what would I do about the basics of my life such as what to do about my wife, extended family, friends and having a basic income to live on.

It was around this time when destiny set in to provide me with major answers in my life. Tragically my second wife passed away, at the age of fifty, along with most all of my very few male friends. As far as family was concerned, my daughter stepped up to be my most steadfast ally, until my third wife Liz stepped into my life. Finally, I learned if I waited a relatively short period of time, I could take an early retirement on Social Security and solve my financial issues. The only loss I sustained was with my brother and his extended family who roundly rejected me. So much for close family ties.

When I made it to my true home, it was like day and night. It was as if a huge weight was lifted off my shoulders. My mental health improved with the help of therapy, and I was better able to face my life on a more equal basis than I ever had before. Surprisingly, I had very little re-arranging to do to live in my new house. It seemed my inner female self-had been not so patiently waiting for her chance to take over my life. Once she earned her spot in the public eye, she knew exactly what to do to survive.

 

 

It Never Got Old

 

Key West, Florida on Vacation. 

All the decades I spent of my life on the journey from male to female never became old and boring.

Even though I spent decades to arrive in my transgender womanhood, surprisingly, the trip never got old. Perhaps it was because I was so entrenched in my male existence and could not get out. Certainly, I knew I did not want to receive any participation trophies simply because I was semi successful as a man to place on my imaginary mantel in my mind. I learned quickly where my true learnings were with my gender and my search for truth never was not exciting. I can vividly remember all the times when I first went out shopping as my true self and thought I was accepted as a woman by the clerks I encountered. When, in fact, they were accepting me for my money first.

It did not matter to me at the time because I was scared to death and was just trying to find my way in a new world I had only every dreamed of. So, this was what it was like to shop as a woman? I loved it. I also loved it when I was able to present well enough to relax more and be brave enough to expand my horizons. I began to stop for lunch on my shopping trips so I would have more one on one time with the public at large. Instead of just going to a big bookstore just to browse, I started to stop for a cup of coffee and to use the rest room for the first time in my life as a transgender woman. Through it all, I was surviving and thriving and most importantly, my life suddenly never was old again.

From there, I started to go out at night and discovered a whole new world to be involved with. This was my much-publicized time when I gave up on male gay bars, and began to seek out more venues I could enjoy myself in. The bottom line was, if I was going to be discriminated for being trans in a gay bar, I could find somewhere else to spend my money. When I did find other venues, my life really began to be exciting and new, it never got old being accepted in a new venue which normally featured big cold beers along with big colorful television screens to watch sports on.

From that point forward, life really began to speed up on me. It seemed every night, something new was happening and I was learning the nuances of being able to cross the gender border. I believe I was not convincing anyone I was a cisgender woman but on the other hand, I was a woman with a different background. The distinction became an important one for me to have to succeed in the direction I wanted to go. The direction of course, was the path I was on to leave my closet permanently and join the world as my true self who should have been in control the entire time. Even though the path had plenty of dead ends and sharp curves, following it never got old.

Since my path never got old, I knew I was on the right one for the first time in my life. The new freedom I felt propelled me when I was doubting which direction I should take in my life. The vibe I felt was real and I decided to risk all the materialistic items I had as a male would be risked and could possibly go away. Which meant everything, including spouses, friends, and employment had to change. Naturally, I spent hours, days and even weeks agonizing on what I was going to do.

The fact which kept coming back to me was, I had gone to far down the femininized path I was on to ever go back to the male life I had known. I even realized, I was much more than a cross dresser or a man who liked to look like a woman when he could. Or I was sliding down a very slippery dangerous gender slope towards a very steep cliff and I had no idea of how I would land.

It turned out I had nothing to worry about. With the help of several women friends, I had made along with gender affirming hormones, my landing was surprisingly soft. Even after I did, I still could not relax. Being comfortable with myself as a transgender woman proved not to be an option. The whole process never became old, and I could not live without it.