Down the Transgender Rabbit Hole

Going down the transgender rabbit hole was difficult for me.

The hole I chose was very dark, and full of dead-end passages before I ever had the chance to see any daylight. As I pursued my long-term dream of living as a woman, I needed to go through quite a few serious changes. In my rabbit hole, there was very little to no help. Especially, any guidance initially from other girls or women around me. It took me years to quit being a victim of my gender issues and make them an opportunity, as I scrambled around my rabbit hole to make it more comfortable.

Of course, it never became more comfortable, and exactly the opposite was true. The further down I dug, the darker my life became. Out of desperation, I searched for my gender daylight. Way past the annual Halloween parties I was going to dressed completely as a woman. Once a year in the public’s eye just wasn’t going to make it for me anymore. I needed other outlets to test how I was doing as a transgender woman. Novice or not. When I was out for the longest time, I felt like the rabbit which was being circled by a hawk. I was so unsure in my new high heels, I could not have run if I had wanted to. I was forced to stay and get abused early on.

I guess I was lucky that my abuse was relatively mild in nature as compared to what it could have been. I was just stared at and laughed at for the most part, until I learned to blend in with the ciswoman world at large. As I did though, I was sent flying down my transgender rabbit hole in tears as my progress was slow. At that point, two things happened. The first was, my hole became my gender safe place where no one could reach me. I was always the pretty girl I wanted to be. The other was the unforgettable sensation of why I was attempting such a crazy journey to start with. I was fairly successful in the male life I never really asked for, so why rock the boat and risk drowning.

Another important lesson I learned was my perception of a woman's life was all wrong. It was like I was watching a slide show on the walls of my rabbit hole when I viewed women. It was not until I tested the daylight of the world, did I realize the truth of what I was about to face. The most important truth I learned was how completely women interacted with men in the world and how innately strong they were. I wondered how and when I could ever fit in as a transfeminine person. I found the only way to learn was to do it and see if I would ever be let in to play in the girls’ sandbox.

To finally make my way into the sandbox, I needed to extend my rabbit hole even farther than I ever had imagined. Since I was always inherently shy, learning to look another woman in the eye and communicate with her was always so difficult for me. It took me years to have the confidence to believe in myself and do it. The most frustrating part was when I thought I had my new life all together, something else would come along to destroy my dream. My rabbit hole had collapsed and needed to be rebuilt. Once I accepted the new challenge of transgender womanhood, I moved on and rebuilt my rabbit hole larger and stronger than ever before.

As transgender women and trans men, we all have our rabbit holes to negotiate. Some are similar, some are not but along the way, we all end up giving away something that is precious to us. Sadly too, some of us discovered our rabbit hole was too deep or built so poorly we had to turn back. I’m referring to the so-called “detransitioners” who the gender bigots and TERFS love to use us as an example of failure in the transgender community. I believe the number of people in the community is much lower than the bigots like to point out, so it doesn’t really matter that much to those of us who have carved out a new life when we left our rabbit holes and carved out a new life.

Sure, it was never easy doing all that work, but in the end, it was so worth it to achieve a dream and stay out of the old hole I had built myself forever.

 

 

  

In the Wrong Room?

 

JJ Hart ahead of first Girl's Night Out.

When I first jumped out of my dark closet and into the bright world, I wondered if I had jumped into the wrong room.

There are other words for my feelings such as impostor syndrome, but I was not far enough along in my transgender development to know them. All I did know was I was feeling ill at ease when I was with another group of women. Which was nearly fatal mistake when it came to being accepted. I discovered how perceptive ciswomen were in their world and could spot a fake miles away. So, I worked hard to show them my truth. I really wanted to earn my way into their world.

It took quite a bit of work and time but slowly I began to be invited to special girls’ nights outs. I never turned down an invitation no matter how terrified I was of going until I began to feel as if I was not in the wrong room after all. It helped when I paid attention to what the other women were doing and saying, and I tried to do the same. As I suspected, the conversations revolved around family and kids, so even though I could not share any birth stories, I could talk about my daughter as a loving parent. A door was opening for me to enter a world I had always dreamed of as an equal, and I cherished my opportunity to learn.

I discovered too that most of the other invitees accepted me easily except for a few I rather not mention. No matter how much they glared at me, I was able to ignore them and have a good time. I was learning I had as much of a reason to be in the room as they did, an invitation from the alpha female gatekeeper who I respected completely for her diverse beliefs. In her life, she was her own contradiction in terms as I saw her. Primarily a strong Christian woman who accepted me for who I was.

On the other hand, men were a completely different story. From the time I started my male to female transition, I was ushered out of the boy’s club I had become a comfortable member of. I learned relatively quickly on the few dates I went out on with men to be quiet and let them lead. No matter how mundane the subject, and how much I knew about it. It worked as I settled into a new world having a lesser IQ. My dates were so rare with men that I never had a chance to feel the chill of being kicked out into a new world I always wanted to live in.

In short, I was thriving in my world and all thoughts of being in the wrong gender room went away. I was in no way an impostor and I deserved to be there. Rather than having a fancy new handbag, I had a fancy new confidence to go with everything else good which was happening for me.

Sadly, the only remaining problems were the same massive ones I refused to face. What was I going to do about my spouse who did not want to live with a woman, all the way to how I was going to support myself financially if I decided to jump the gender border from a male life, I was successful at, to a female one which was largely untested. Helping me along was the knowledge of knowing from all my ciswoman interaction in the real world was successful. It would be difficult, but I knew deep down I could make it. Mainly because the whole process seemed so natural to me.

Finally, I realized I was living my whole life backwards. I was always fighting the idea I was a man trying to be a woman. When in fact the opposite was true. I was a woman all along trying to be a man. It was no wonder I did not feel at home in either of the two main binary genders, male and female. And until I chose the right room, my life and mental health would never improve.

It seemed destiny was on my side as I made the journey into the transfeminine gender side of life. To arrive I had the cruel death of my wife (as well as other close friends to deal with) plus closing my business to overcome. Against all odds, my wife Liz found me online of all places and helped me to rebuild my shattered life. I was able to locate the proper feminine room and stay there.

I Almost Waited too Long to Transition

 

Image from Lizgrin F 
on UnSplash.

I almost went too far when it came to not deciding to transition from male to female in my life.

During the previous half century of cross-dressing my life away in the mirror, I put off making my final decision so many times. One of the main problems was, I was sixty years old and was forced to consider my mortality, which I had always taken for granted. Plus, another issue I had was feeling just a little too comfortable with all the male privilege I had struggled to build up in my life. Often it seemed, destiny had stepped into my life to guide it a certain way because I was very self-destructive and selfish. So much so that my mom always said I had a guardian angel riding with me when I did stupid things behind the wheel. All along, of course, I was trying to hide the pain of hiding who I truly was.

On the other hand, I was basically an impulsive person who felt all rules were temporary and could be worked around. Such as my time in the Army when I was able to land a job with the American Forces Radio and Television Service (AFRTS), which was nearly impossible to do. In the meantime, I was facing the biggest struggle of my life as I needed to figure out what I was going to do about my gender issues. It was always the elephant in the corner of every room I was in.

What I decided to do was research as much as I could my dream goal of living a life as a transgender woman. When I did, my very real struggles began. Early on, nothing came easy on my gender path. I was being laughed at when I went out in public as a novice until I got it right. As I fortunately exited that portion of my life, I was able to see more clearly what I was up against, and it was daunting. I had very little idea of the layered lives ciswomen lead as compared to men. When I realized what I was up against, I needed to set my transition timetable back. And to make matters worse, my male self was becoming increasingly successful in his life. Building up a solid base of marriage, family, friends and job. How could I ever replace all of that and when could I do it.

The only recourse I had at the time was the worst one I could consider. Internalize my deepest gender thoughts and keep trying to attempt to do the best I could to survive a life caught between the two main primary genders. Three days as a trans woman and three days as a man was killing me and I tried to no avail to take the extra day off to relax. It turned out I could not because all I thought of on my supposed day off was what I was going to do the next time I went exploring the world as a transfeminine person. Which brings up a good point, during this time of my life, any thoughts I had that I was just a cross dresser were slipping away. Only to be replaced by the fact that I refused to accept. I was more a woman of my own making than I ever thought.

One way or another it was in my fifties when I began seriously researching the word transgender and what it meant to me. I was happy when I finally found the terminology which applied to me but again what was I going to do about it. I was not getting any younger. I still made the worst of all possible choices and continued my path of least resistance. At least that is how it appeared to the outside world which I was effectively hiding my efforts of femininizing from them. I had won my award as a strong male role model with a good marriage, family and job, and now I wanted to give it all back for a radical gender change into womanhood.

When my sixtieth birthday rolled around, I finally decided I needed to make a major change before it was too late. I went to a doctor and took the steps to be approved for gender affirming hormones or HRT and the real changes started. As good as I felt though, I could not shake the sorrow I had from moving permanently away from my male life. Even after my mental health improved.

Finally, I realized I had waited too long for the change and should have had the courage to do it long before I did. But at least I managed to make the major gender change I did before it was too late. And what about my elephant who was my constant companion? I set it free.

Trans Girl on a Cliff

 

Image from Majestic Lukas
on UnSplash. 

A few years ago, sixteen to be exact, I found myself at the ultimate crossroad in my long gender journey.

I was sixty at the time and I had pursued all the mini gender bucket lists I could to see if a complete male to female gender transition was possible, and it certainly was. More precisely, I was becoming successful at carving out a completely new life as a transfeminine person with people who never knew anything about my old male past.

For some reason though, my old male self-refused to let go, causing me undue stress and tension. He kept arguing that there was simply too much hard-earned male privilege to just throw away for good. Plus, once I went down the final path to trans-womanhood, there could be no turning back. The cliff I kept sliding towards was increasingly steep every time I looked at it.

Through it all, I managed to turn a deaf ear to him and looked ahead to a new exciting life which felt so natural. Which is one of the main reasons I did not back down into my previous world of serious cross-dressing adventures. At that point, I needed to assure myself that my new feminine life would be more than adventure, it would be a heavy dose of reality with no turning back to the male clothes still in my mental and physical closet. More than anything else, the new Estradiol hormones I was on helped me mentally to prepare for the new life I was to face, while the clothes in my closet were just waiting for a visit to my local thrift store to give away. It was an emotional day when I severed ties with the last of my male clothes, but I did it anyway and the only thing I saved was my old Army uniform.

Ironically, when I did all of that, I was between serious relationships and all alone in the world to make and live with my serious gender decisions. There was nobody else to discuss my decision with. Just me, all by myself, which gave me wonderful clarity of thought. As the fog of the regular world dissipated, I was able to see clearly down the cliff and determine what the future held for me if I followed my ultimate dream of being a woman. Finally, after the umpteenth time of worrying over my decision, I decided to make it and take the weight of worry off of my shoulders. To ignore the cliff, I was facing, and jump was liberating to say the least. It was like I could breathe again.

As I made the final tumble down my gender path, I remembered all the twists and turns I made to make it. All the times I was laughed at or worse as I learned my lessons I would need to survive if I ever decided to make the final transition. Of course, I knew little to nothing about what I was doing so I was caught making up my woman’s world as I went along, with no help for the longest time. Once I got the help I needed, I was far along in my transgender development in the world, and I used the help I received from my cisgender woman friends to round out my personality and make my jump off the cliff seem easier to take.

With everyone’s help, I jumped and felt as if I could fly in the new feminine world I had chosen. There was no unexcepted crash and burn that I had feared for so many years. I had done plenty of prep work in the major areas I needed such as appearance, communication in the world, and so much more such as what I would do to support myself since I knew coming out on my old job would be impossible. The nights I spent going out in the world by myself as a transgender woman were behind me and I could look forward to a new future. I worked hard to jump from that gender cliff and have a safe landing.

My friends helped me to socialize more at lesbian mixers than I ever thought possible and I was able to retire early on enough of an income, so I did not have to worry about going back to work again, so my main bases were covered. It turned out, all those years of worrying what would happen if I jumped the gender border were wasted as I went all out to make sure I could make it as a transgender woman in the world.

Who knows, maybe all the extra work I did in the world just helped me make the landing I went through a little less intimidating and softer.

If I Had Known Then

Image from Hc Digital 
on UnSplash. 

The age-old question is, if I had known then what I know now, what would I have done differently.

Realistically, since I don’t have some sort of a magical time travel machine, I could not do anything differently. But if I had it all to do over again, I would have tried to come out of my male gender closet much earlier in life. I would have taken advantage of the youth I had and invested it in progressing to being a transgender woman. Even though I was well into my thirties before the term “transgender” was even invented or discussed. The truth of the matter is, I wasted too much time between Halloween parties when I could safely cross dress as a woman. Finally, once a year just wasn’t enough and I needed to open my closet door a little more and explore the world as a transgender woman.

If I had known then, I would have realized there would be no shortcut towards my ultimate goal of living as a trans woman. I would have to find my own unique path to being a woman that any other female has to do. For years, my second wife tried to tell me the truth, but my male ego stood in the way, and I refused to listen. I thought just looking the part of a woman was enough until getting out into the world proved me wrong. I needed to pay my dues just like any other cis woman before I was allowed to play in the girls only sandbox. It was a difficult struggle to get there, full of many setbacks, but somehow, I persevered and kept moving forward, often at the expense of my marriage and my male life. Primarily, my marriage since I was very close to my wife and she was my best friend. If I could go back, I would have tried even harder to be closer to her before she suddenly passed away at the age of fifty.

I would tell her she was my role model and all I really wanted to do was to have her like my feminine self, which she obviously did not. Instead, we fought like cats and dogs until she would tell me to go away and be a woman and spare her the pain. As much as I secretly knew she was right, I was still determined to hold the marriage together and pursue my transfeminine dreams the best I could. It all turned out to be the wrong plan and I suffered. There was not enough therapy in the world to help me through such a cut and dried situation. Sooner or later, I would have to make a decision in my life and choose between my two strong women…my wife and my inner feminine self who was becoming stronger and stronger by the day.

If I had it all to do over again, I would have set my male self aside and det out to build a new life as the transgender woman I was always meant to be. In the short term, it would have been difficult, but in the long term I would have been happier, and my mental health would have been better with the gender pressure off. Also, I need to bring up my excessive use of alcohol to mask my pain. Somehow when I drank, I felt more like a man and less like the woman I wanted to be. It was not until I was well into my male to female transition that I could decrease my addiction to alcohol and now I am lucky if I have two drinks a month.

Even If it is impossible to go back, I wonder how my life would have been if I had pulled the plug on my male life earlier. I certainly would not have missed all the time I was daydreaming my life away about how it would be to live a feminine life. How much better and productive could I have been. On the other side of the coin, I know I would have lost valuable time learning all I needed to learn to survive in such a new radical feminine world. Time seems to always erase the negatives and accentuates the positives.

Even still, knowing how successful I was able to be in my gender transition, it is impossible for me to not think what could have been possible if I had made the move earlier.  Even though my path was difficult enough, I may have had a smoother path if I had done then what I know now.

 

  

Gender Awakenings

 

Image from UnSplash.

Gender awakenings came early and often for me. I say early because from my earliest days of conscious life, I knew something was not right about me. As I always point out, this was in the 1950’s in the dark days of the pre-internet era when any gender information was difficult to come by. To make up for it, I experimented wearing my mom’s clothes and trying to apply her makeup the best I could. Then I would wear out the carpet in front of the hallway mirror admiring myself. Somehow, I convinced myself I was a pretty girl ready to go out into the world.

When I finally broke out of my closet and tried out the real world as a novice cross dresser, I received a rude awakening. Initially, it came from groups of teenaged girls I encountered in the malls I went to. They were brutal and not shy about laughing at me. Too many times, I was sent home wondering what the problem was with my image or presentation as a woman. One thing was for sure; the mirror was lying to me when it told me I could pass with no problem. I just had to do better if I was to survive in chasing my dream of living as a woman. In fact, at times it looked as if I had no chance of ever making it at all.

Fortunately, as dreams went by, I found I had an achievable one as the years went by. But achievable never meant easy. I had many negative transgender awakenings mixed in with just enough gender euphoria to keep me moving. It could be as little as encountering a group of teen girls with no reactions, all the way to having lunch when I went out to shop. What I was slowly doing was replacing my mirror in the hallway with the world. Maybe this male to female transition trip was not going to be so difficult after all.

At this time, over confidence got to me on several occasions when I had left the relative safety of the gay bar scene and tried to move to more familiar venues such as sports bars and even lesbian taverns. The problem was, I became too comfortable when I was accepted and had a tendency to slip too far back to old unwanted male roles. Keeping track of where I was in my new life and taking too many chances. I was guilty of being in the wrong place at the wrong time and nearly suffered from it until I learned my male privilege of safety no longer applied. I also was not prepared for how fast I lost part of my intelligence when I was dealing with men. Very early on, I found myself being completely ignored when I ended up with a group of men. Even though, I knew more than they did.

As I learned I would have a much easier path to acceptance from other women than men, I discovered the hard way that was not always the case. The well documented times when I had the police called on me for using the women’s room at one venue, all the way to being called a pervert in another place come to mind. Those were deep wounds to overcome but somehow, I did and found stable places to go to which accepted me for who I was. Even to the point of protecting me as their token transgender woman. The basics of smiling often, causing no trouble, and tipping well did wonders for me.

Even still, I had to be careful because I had a wife, family and job to come home to after my dream evenings as a transfeminine person. Soon, the delicate gender balance I was trying to maintain became too much to bear. I was to the point where I was just waiting for the next high heeled shoe to fall, or the next gender awakening to occur. I just knew I had come too far to turn back now, and my dreams were within reach. Only my big three stood in my way and destiny was coming along to take care of them.

My wife suddenly passed away, leaving me free of anyone except myself to answer to when it came to my gender awakenings. Plus, the only person I really cared about in my family (my daughter) became my staunchest ally when I came out and I took an early retirement, so I did not have transition on a job of any sort.

Once my gender awakenings started to come, they came fast and furious like a runaway train. The best part was, the whole process felt so natural, I never wanted to turn back.  Somehow, I kept the train on the track.

 

 

 

 

 

 

Gender Blockers

 

JJ Hart, picture taken after mixer.

Gender blockers often came fast and furious at me as I lived my life.

First, I needed to figure out how to camouflage my big boned testosterone poisoned body so I could present well enough in the world to get by, once I arrived there. Which in itself was a big enough hurdle to face. Then I summoned the courage to go out of my closet and into the world, I learned the hard way how much further my trip would take me and how many people would try to block me.

At the beginning, it was never easy, especially around teen girls who always seemed to figure me out and have quite the giggle at my expense. Often, it took weeks for me to recover, go back to my cross-dressing drawing board and try the world out again. Fortunately, these were the days when I was attending the cross dresser-transgender mixers and parties in nearby Columbus, Ohio. At these events, often I was able to compare myself to others around me with the same gender issues and see how I was doing with my presentation.  Also, I left the diverse parties I was going to by discovering a deeper understanding of where I possibly was going in my life. I was learning I was so much more than just a man with a hobby of looking like a woman. I kept going back to the fact that increasingly I wanted to be a woman. It was my dream.

Often, my dream was shattered by a number of outsiders. While my wife was very supportive of me as a cross dresser, she completely drew the line at any suggestion I was transgender and had nothing to do with me starting HRT. Then she would team up against me with my male self who was beginning to feel threatened with losing his world. Mainly because I was beginning to have an idea of how my gender dream could become a reality. If my male self was becoming successful in conquering all the blocks and hurdles, he ran into, why could not my feminine side do it too.

At times, my male to female transition process was allow and tedious, and at other times fast and exciting. Frustration would set in when I would try to spend three days a week concentrating on my transfeminine side of life, only to have to revert back to my old male side the remainder of the week. Including my job which was male dominated. The whole back and forth gender life destroyed my fragile mental health and made my life hell, except when I was in my transgender phase. I had too many plates in the air which I was trying to keep spinning. Sort of like trying to keep several girlfriends happy at once.

I could finally take it no longer and needed to try to start removing my roadblocks one at a time. I began with the social roadblock. Could I actually begin to carve out a brand-new life as a transgender woman where no one knew of my past. To my surprise, I found I could. Probably because when I got past the point of thinking I was trying to fool anyone into thinking I was a cisgender woman, I just became me, and I was good enough not to scare anyone away.  One roadblock cleared. The next thing I needed to figure out was how I was going to support myself. Because transitioning on the job was out of the question, I needed to find a different answer. I took so long to do it, the problem solved itself when I got close to a point where I could take an early Social Security retirement and then sell the many collectibles my late wife and I had collected to survive.

With all the gender blockers to my dream out of the way, I needed to push my own feminine self-improvement program ahead. It meant seeking out an understanding doctor to prescribe me gender affirming hormones. When I did, I was able to see and sense a noticeable difference in my external and internal self. My skin softened and my hair grew so I could use less makeup and leave my wigs behind for good. All of which helped me to present better in public. Internally, I could not believe all the changes HRT was helping me with. I was more emotional as my world softened. For the first time in my life, I could cry tears of sadness and even joy.

From then on, I had paid all my dues and was ready to settle into the dream life I never thought I could obtain.

Finally, as a serious side note, it is 9-11, never forget.

Gender Dreams

 

Image from Greg Pappas 
on UnSplash.

This morning when I woke up, I took a moment to remember the sadness I felt when I got up in the morning and I was not a girl. I had the same sad realization, I was still a boy and nothing had changed. Plus, it is important to point out that I had no other dreams when I was young such as being a professional athlete or a doctor. All I wanted was to be a girl. I figured I was the only boy in the world who felt that way.

It was on those mornings when I needed to realize I was still male, and I had a long trip to make if I ever was going to change it. As my life became more complex, so did my gender dreams. Sometimes, I could not wait until I went to sleep to see what sort of dreams, I would have that provided me a respite from the days activity of being a man.

It was not until I decided to come out of my closet and test the world as a transgender woman, did my nights began to change. Replacing dreams with action was often a very scary proposition. But it was one thing I had to do if I was ever going to see if I could make it to a new transfeminine world at all. Would the public ever come to a point where they would accept me as more than just a man in a dress. Out in the world to be laughed at. If I could never make it past that point of being a cross-dresser, did I want to go on any longer and forget all the dreams I had. I finally discovered there was much more to being a woman than appearance and it was just my male ego trying to influence me.

Still, as I struggled along in my novice cross-dressing years, my gender dreams began to change with it. Instead of just wanting to be a woman, I started to dream of how it would be to live as an attractive woman and not have to worry about my presentation so much. I think it was because I was becoming more confident in myself, and my subconscious self was adjusting to the new me. More or less, I was reacting to the kinder, gentler world I was in as a transgender woman, and I loved it.

My main problem then was, could I make it to my dream when it became a reality. I was frustrated when I thought I could see the finish line and it was taken from me due to unknown transitional experiences such as what would I do about supporting myself if and when I made the decision to go from a male world to a female world. And would I need to prepare to be lonely the rest of my life because the possibility of someone loving and accepting a trans woman were exceedingly rare at my age of sixty. I was fortunate and exceeded all my dreams when I was financially able to take an early retirement and support myself and found my wife Liz (or she found me) on an online dating site. At that point forward, I had painted myself into a corner and I had no real reason to not follow my dream of being a transgender woman full time. Because I had finally faced up to myself and realized I had always been trans parttime, even though I could not share it fulltime with the world. 

As I faced up to reality, my nighttime dreams began to change also. Slowly my old male is disappearing from my subconscious too, He is being replaced by new dreams with me living as my true, authentic self. Maybe it is because he was pushed out of his final hiding place in my mind. Whatever the case, I was not sad to see him go.

I wonder now, what my childhood boy would think if he could see me now. Doing much more than just hiding in a gender closet waiting for brief moments to escape and explore. I am sure he never thought he would have the ability or confidence to be who he always wanted to be. Not an athlete or a doctor, just myself…a woman. I certainly had to come a different direction to claim my prize but maybe by doing so, I appreciate it more because it was never just given to me.

The boy I was would have never known his dreams would have never turned out like this, and being happy would not have been so far away also when she was playing with the girls. Where she always belonged.

Planting the Gender Seeds

 

Image from Sebastian
Demitro on UnSplash.  

After my initial experiments with my mom’s clothes, I blamed the cross dressing and started to plant my gender seeds, as I wanted to be feminine all the time. Sadly, for me, it took me decades to realize the seeds were already planted and were growing. All along, I had an idea that was the case, but I was afraid to do anything about it. Mainly, because I had no one to turn to for understanding. The times were very dark in the 1950’s when I was growing up for any understanding of gender issues at all. As I always mention too, I grew up as the oldest son in a male dominated family, so my goals were set for me as a boy.

It wasn’t until much later in life that I had served my time in the military that I was able to water my gender seeds and watch them grow. My first realization I could come out of my gender closet came in the final months of my time in Germany in the Army when I went to a Halloween party thrown by the nearby hospital staff dressed completely as a woman with shaved legs and all. The biggest moment came weeks later when I admitted to my closest friends, my costume was not a costume at all. I loved to dress as a woman and was a transvestite as we were called back then. In the 1970’s.

The best part was, my friends could care less and more importantly, the higher up’s in the Army never found out and I was honorably discharged after my three years were up on time with no problems. Coming out to my friends really set me up for success in growing more and diverse gender seeds…until my mom came along and tried to kill them. I was emboldened by my recent success in coming out and one night I decided to tell her. She responded the expected way with shock and the added offer of paying for a trip to a psychiatrist. From there, the discussion rapidly ended, never to be brought up again for the rest of her life. I knew deep down I was not crazy and did not need a mental health professional to tell me I was.

With that knowledge, my gender seeds continued to develop, even though they were in the darkness of my closet for the most part. Until I could stand it no longer, the only times I ventured out in public as a novice transgender woman was the occasional Halloween party and business trip I went on. Somehow, I was able to smuggle my feminine wardrobe, wig, and makeup past my wife and enjoy a night out on the town when I arrived there. For the most part, the experiences I went through helped me to nourish my transgender seeds and come away with a better understanding of where I fit into the world as a transfeminine person.

Even though I was becoming more successful in chasing my dream to ever live as a trans woman, I kept finding I had a long way to go. In order to see my seeds finally bloom, I needed to have the cisgender alpha females I encountered to accept me. They closely examined me and let me in to play in the girl’s sandbox. To get there, I needed to tend to my seeds which were still blooming. The mistakes I made all centered around when I was overconfident about where I was headed and I got burnt. Fortunately, I was able to reach down and pick one of my flowers and offer it as a peace offering. The flower was enough to move my life along.

My garden proved to me to be worth all the effort I put into it. All the tears I suffered early on when I went out into the world as a transfeminine person were used to water my seeds and watch them grow. Plus, all the time and effort I put into learning the makeup arts after looking like a clown in drag came back to help me. I took the time also to plant diverse seeds which helped me when I encountered difficult situations. Which I never knew where and when they were coming from.

It turned out that I never had much of a green thumb in my male life, but a flourishing trans thumb when it counted the most. It was quite the discovery for me when I discovered how layered and complex the women’s world I was in. I also benefited from the careful job I did of planting and protecting my young seeds. On occasion, I regret the time it took them to grow, but in many ways, I was the prisoner of when I grew up in the dark days in the pre-internet era. But taking the extra time to become strong and thrive in my new life was worth it. As I said, the seeds were there all along, all I needed to do was nourish them. 

 

 

The Same Old Road

Image from Danijel Skabic
on UnSplash. 

Quite early in life, I grew tired of the same old gender path I was on. Although I could not exactly put a finger on what was wrong with me, I knew something was. What is that definition of insanity? When you do something over and over again and have the same results, I think it is.

Also quite early, I thought I was the crazy one because of my deep-seated desire to be a girl when I was being forced into being a boy from birth. Little did I know, I was destined to become a late gender transitioner in life and must deal with my own form of insanity for fifty years, before I had the courage to do something about it and get off the same old gender road I was on.

As I traveled, it seemed like I was getting better than ever at finding every bump, curve and pothole along the way. Possibly, I was attempting to make my male to female journey even harder, just to prove I could do it. As I like to say, my gender workbook was blank and everyone around me could tell it. Plus, when I first began to get serious about trying out my feminine self in the world, the only outlet I had were the annual Halloween parties I went to. Early on I tried to dress sexy/trashy and then after a couple of years built myself up to trying to present as a cisgender woman at the party. Which surprisingly I was able to do way back when I was still into Halloween as my outlet from the same old gender road.

The best part was, I was able to locate side roads along the way as I was able to present better in the world as a transgender woman. The side roads enabled me to explore different rabbit holes and dead ends to see if I could survive in a new exciting environment. When I had the courage to do it, the road actually smoothed out for me, and I enjoyed myself more than I could ever dreamed I could. Even with all new gender euphoria I was experiencing, I still had to be more careful than ever that I did not crash and burn my male life…yet. I still needed him and what he could provide such as all the male privileges he had worked so hard to earn.

One way or another, I was definitely not on the same old road as I continued to experiment with living as a transfeminine person. I made mini bucket lists of the new things I needed to accomplish each day as a transgender woman and set out to do them. The list could be as small as working on a more feminine walk, all the way to going to a new venue I had never been to before as a trans woman. More often than not, I found the world accepted me as just another woman and did not really care. The whole experience was a confidence booster and enabled me to travel roads which were not the same old ones I was experiencing as a man. One of the main road twists I always mention was when I was able to escape the gay venues I was going to and finding other lesbian or straight venues which supported me.

Suddenly, I was having so much fun choosing all the new roads I found, I had a difficult time deciding where I was going to go. I never thought I was any good at road building until those exciting days when I was finding myself in the world. Some nights, I even felt like I was on some sort of a feminine interstate highway with all the interaction I was having with cisgender women I ran into. Sadly, I finally needed to slow down before I wrecked and burnt myself out, but not before I experienced more than I ever thought I could. My dream life was right down the road, if I could just reach it. I stopped, looked around and I found, all those years thinking I was crazy because of my gender issues were wrong, and I should have listened to myself long ago and I would not have to gone down all the rabbit holes I went down and then being stopped at dead end streets to prove to myself I was still the man I never was.

I was never good at auto mechanics as a man, and it showed when I tried to keep driving down the same old gender roads. As a transgender woman, I was able to take the pressure off driving down the same old roads.  

 

  

Out od Sight...Out of Mind?

 

My wife Liz on left and daughter on right.

Most if not all transgender women and trans men go through phases in their life when they think gender issues are out of sight and out of mind. It is not entirely different than the moves some state legislatures (Ohio) are going through to try to erase us in the public’s eye.

If you read my posts at all, you know how I feel about that. Trans people have always been around and always will be. Attempts to erase us will be futile. On a lesser but just as important level, we try to erase ourselves by purging our lives too. I know the guilt of being a cross dresser or transgender woman became too much for me to handle and I threw out most of my treasured feminine wardrobe and makeup. Out of sight, out of mind I thought.

In the long term and the short term, none of my purges worked because I refused to accept my true self. I had my life all backwards and I was not a man who cross dressed as a woman, but a woman who cross dressed as a man. Until I figured it out, I kept trying to hide the obvious. Of course, it did not help as I started with two gender strikes against me. I went through birth as a male and then had to go through male puberty and suffer from what I called testosterone poisoning. My body kept the bullies away and allowed me to play sports but caused me torment when I was in front of the mirror trying to be a pretty girl.

As life went on, I thought for the most part I had learned to live with my gender dysphoria the best I could. To this day, though, I wished I could be a “normal” male. How much better could my life be if I could socialize with the other males around me without feeling as if I was an outsider. I grew tired of being an actor inside my own skin. The only thing I could do was mentally try to get rid of my feminine self. Taking me full circle back to why I was keeping all those clothes, wigs and makeup anyway. It took me by throwing them away to understand exactly what the problem was. It was not a problem unless I it made one, which I was by purging again.

Deep down I knew I was wrong and very shortly I would be re-stocking my fashion and make up to try my best to present feminine again to myself and the world. However, I was very stubborn and my male self-hung on way too long refusing to give up on his hard-earned male privileges. Life could have been much easier by staying where I was in the gender world, but it was just wrong, and I couldn’t. The more I lived as a transgender woman, the more natural I felt, and I never wanted to go back into the male world I had made the best out of.

Increasingly, the male purge was looking to be the one I was going to attempt to make. I was sick of living a gender lie, and I wanted to reverse my idea of living. I wanted to feel “normal” again but this time around a group of cisgender women. Flipping the gender script on my life was the most difficult thing I had ever attempted to do, but somehow, I made it through the female gatekeepers and did it.

In my new transfeminine life, I was rarely out of sight and out of mind. I had a lot of help to do it who I will never forget. I had spent my whole life chasing a dream and had finally achieved it. As I symbolically and literally gave my male clothes to charity, I stopped to remember the entirety of what I was doing. I was giving up the male side who had dominated me for so long. To be sure, he had served me well, but it was time to go, and this final purge was a triumphant one for my transgender woman who had waited so long to live. After all, she had her life taken away several times when she was purged nearly out of existence.

She survived and so did I and everything in her power to make things better. When I worried how I would be perceived in a new world. She had my back when it mattered, and it did. Even in the days when she had to give me quite a bit of tough love. She had to watch me grow through my ill-advised teen cross-dressing years into a presentation I could be proud of or at least satisfied with.

Out of sight, out of mind never worked for me.

 

 

All I Had was Time

 

Image from Natalia Rabinovych
on UnSplash.

When we are younger, time seems like it is less of a commodity. When we are in school for example, all we want to do is graduate into the world.  For transgender women and transgender men transitioning, we often take time for granted. At least I did.

As I was coming out of my gender closet, regardless of not having much guidance on where I wanted to go to achieve my dream of living as a woman, I took my time. For a while, when I had finished serving my time in the military, the only outlet I had to being out in the public’s eye were the yearly Halloween parties I went to. Finally, I could see the writing on my gender wall and knew I would somehow have to do something, so I did not have to wait another long year to go out again. Time was being wasted.

It turned out, I could not see the forest for the trees, because there was a huge world just waiting for me if I just had the courage to do something about it. I needed to hitch up my big girl panties, not be a victim because of the bigots, and do something about escaping my closet. The problem was, I was always making excuses about why I could not do something as a novice cross dresser or transgender woman. So, what if my ego was wounded when I was laughed at early on, I just needed to go back home and figure out what I was doing wrong and fix it. Time was going by, and I was not getting any younger. Little did I know then, as I was in my thirties, how much farther I would have to travel.

I had my own transgender biological clock I was dealing with. Like any woman, I knew I only had a finite number of years to look my best to try to socialize in the world. All of this happened before I learned appearance was just the stepping off point when I tried to interact with the feminine world. My wife tried to tell me, but I would not listen, and I lost years in my male to female transition to learn for myself what she was talking about. Again, I was spending too much time as a victim wanting my wife to explain what she was talking about and not explaining it better to me. The problem was, I would not have listened anyway, my old male ego was still too strong.

In the meantime, I was getting myself caught up in major gender contradictions. I was spending up to three days of my week trying to learn the basics of being a transfeminine person and then turn around and having to revert back to the old male life I increasingly wanted no part of. It was no way to live and often I felt as if I was one of those jugglers I saw on television when I was a kid, keeping several plates balanced at once in the air. Ultimately, the entire gender back and forth nearly killed me.

My suicide attempt, among other things, woke me up to the fact I did not have all the time in the world. Especially if my self-destructive actions were trying to take it away. If I ever was going to have a chance to achieve my dream of living as a transgender woman, I might have less time than I thought to do it. At that point, I shifted my transition plans into high gear and began to explore in earnest if I could do it at all. Maybe it was my impossible dream. One way or another, I was in my fifties and needed to decide what I was going to do.

As I began to carve out my new life as a transgender woman, I needed to quickly learn what worked for me and what did not. My biggest move was when I worked my way out of gay venues where all they did was perceive me as a drag queen and enter the real world where I needed to prove I was more than just a man in a dress, wearing makeup and a wig. With more than a little help from my inner female who had waited so long to live, I was able to establish myself as a viable person to the public. As my trans woman friend Racquel said, I passed out of sheer will power, which I did. I proved I was not trying to fool anyone into thinking I was someone who I was not. For better or for worse, my friends knew they were dealing with a unique woman who had used her lifetime to arrive at the same point as they did.

Maybe I had spent my time wisely. One way or another, I learned a lot about the binary genders as time flew by. 

 

Come Out Swinging

 

Image from Chase Li
on UnSplash.

Often, I write about running home to dress in my skirts and put makeup on to hide the failures I was feeling as a male.

My plan worked well until I discovered I was advancing so far and so quickly as a novice cross dresser or young transgender girl, I was unknowingly destroying my hiding place. Someone turned the light on in my closet and suddenly I had nowhere to go. I needed to come up with a plan to come out swinging or I was doomed. In addition, I still had to be very careful not to be caught and end up in a psychiatrist’s office declaring me mentally ill. Then I would really have nowhere to hide.

The better I became at the art of makeup and dressing myself, the more I needed to consider what I was doing and wondering if I should come out swinging at all. The problem continued to be, I was building more male privileges in the life I was living. My life was like shadow boxing myself as I sought out answers. Like most of you, I was risking a lot as I came closer to pushing all my life’s chips to the center of table and betting it all on the fact I was a transgender woman all along.

Then I went into my highly recommended experimentation years of my life. In order to have any sort of an idea if I wanted to live as a transgender woman, I needed to walk a mile in my new high heeled shoes. Those were the scary yet exciting nights when I escaped the gay venues I was going to and began to attempt to establish myself as a regular in lesbian and other straight venues I was used to going to as a man. When I did, I discovered I needed to make another transition from serious cross dresser to transgender woman exploring the world. To my amazement I was successful when I went to venues such as TGI Fridays and socialized with other professional women. Maybe I did not have to swing so hard after all to escape the dark confines of my gender closet.

To be sure, I still had setbacks when I came out into such a different world, but I had enough gender euphoria to realize I could live out my dream if I worked hard enough at it. At first, I suffered from the “what I thought a feminine life would be” syndrome. I was trying to put all those years of closely watching how women lived into actual practice without paying my dues in the world. While I resented the fact, no one would let me see behind the cisgender woman gender curtain, I was becoming a victim which did me no good in the short or long term. So what if I did not understand what I was doing wrong, I just had to figure it out and do better.

One of my major problems was solved when I finally came to the conclusion I was never going to be accepted as a cisgender woman, but I could find my own version of womanhood on my own path. That is when I started to wear only one wig, settled on one name and began to build a new serious life as a transfeminine person in the world. As I settled into a new life, I found that many people (especially women) appreciated my honesty in a world of fake people. I was surprised at all the female attention I received and was relieved I did not have to attempt to change my sexuality.

The more I changed, it seemed the more I stayed the same as my long hidden feminine soul took control finally. I was dealing with life on a one-to-one basis for a change without having to swing away all the time just to survive. As HRT hormones entered my life, it was just another example to me of what took me so long. My body took to the gender affirming hormones flawlessly and I was off to yet another transfeminine adventure. My age and hormonal status led me down a new road of dealing with confrontations, no more could I try to macho my way through trouble, I needed to take the feminine path and try not to get into a situation I could not get out of before it happened. Or no more swinging away for me. I needed to use my brain for a change.

As I have pointed out in previous posts, I was never a good athlete and could never hit a curveball when I tried to play baseball. I finally took it all to heart and quit trying to hit a curveball altogether and settled into watching the boys play baseball (and girls too) when I did not have to play. I was tired of banging my head against a hard gender wall and ended up where I always should have been as a transgender woman. I just wish I had not been so stubborn when I was doing it and had shed my male self-long before I did.

 

Closing the Circle

 

JJ Hart at Club Diversity, Columbus, Ohio.

Very quickly when I opened my gender closet door and looked out, I noticed a whole different world I would have to conquer if I was to survive.

To begin with, I was slightly overconfident with my ideas because I had spent so much time studying the girls around me. I was jealous of their pretty clothes and how the boys chased them. I so badly wanted to run in their circle but as we all know, that was not going to be possible for years to come. To begin with, there were so many smaller circles to negotiate before I could advance. So many, I could barely keep track of them all. I had a LONG way to go.

To put it all into perspective, if you remember the Hula Hoop craze, with the round hoop you put on your hips, arms or even neck and spun it around. I was so uncoordinated, I had a difficult time playing with one as I grew up. If I could not even spin a simple hoop around my hips, how was I ever going to accomplish anything vastly different such as changing my gender identity. For the most part, I was naïve and did not understand all the complexities I was facing. While I was obsessed for years looking like a woman, I should have been obsessed with knowing what a woman was really all about. I remained too new to the gender game to be allowed to enter woman only spaces, or what I refer to as the girl’s sandbox.

Then in the middle years of my life when I began to explore the world more and more as a transgender woman, it seemed I had too many hoops or circles in the air. So many, in fact I kept making wrong choices such as the wigs I wore and how I misconstrued how I needed to look to blend in with the public. Instead of dealing from transfeminine strength, I was dealing with my old male ego hanging on and causing problems. I was stuck in my so-called teen cross-dressing years until I rapidly outgrew them in my thirties. Better choices of fashion and makeup helped me to overcome my testosterone body flaws and blend in with the other women who may have had traces of my problems with their body too. Even with all my newfound success, I was still having a difficult time closing my circles. My major problem was I did not completely realize how difficult it would be to stop a life and start over from a completely different point.

As I chased my Mini skirted tail, I had plenty of time to consider what I was doing with my life. In fact, too much as every spare moment I had, I was daydreaming of the next time I would spend as a transgender woman and what I would wear. I am surprised now I had kept my mind on my job enough to be promoted to an upper management position. I would love to have a portion of the time back I wasted. Perhaps, the sky would have been the limit for my male life, but it was not to be because I could not stop until my gender circle was closed.

It finally took a close circle of cisgender women around me to help me through my crisis. My current wife Liz in particular who told me she had never seen any masculine in me at all when I was still living part time as a man. It was the final shove I needed to reach out and close my transgender circle for good.

I don’t think I gained any physical coordination from transitioning, but I am sure I gained mental help when I long neglected woman side took over. I found part of feminine privilege came when I was allowed to participate in a softer side of life which did not revolve pushing and blustering my way through. My new circle involved more mental gymnastics with other women to see where they were coming from, as well as dealing with a passive aggressive side of life.

Not going in circles anymore was a wonderful experience. All my trial-and-error times in the world as a novice transgender woman came back to help me when I made the final transition to where I always wanted to be. No more spinning hoops to deal with which were destroying my mental health. To be sure, all of my bi-polar depression issues did not go away but the overlaying gender issues did. It sounds easy for me now, but all I needed to do all along was listen to my true self and close my gender circle.

 

 

Confidence is your Main Accessory

 

Image from 
Jon Tyson on UnSplash.

Some assume I have reached the point of life I am at, through very few challenges.

The truth is that I faced many challenges along my very long gender journey to living fulltime as a transgender woman. I write about many of them often. As I look back, the one main challenge I faced was having the confidence to move forward to my strong dream. Perhaps the earliest confidence I needed was when I walked down our long driveway dressed as a girl to check the mail. Hoping someone would notice the girl in a miniskirt out of the house on a winter’s day without a coat. Then hoping no one would see me and somehow report me to my parents. Nothing ever happened, so I gained the confidence to keep doing it.

The problem was, there were only so many trips to the mailbox I could take to feel good about my cross-dressed feminine self. Here I was taking all that time and effort to feminize myself and having no outlet except the mirror. I was frustrated in my little closet which I had no idea of how to escape from. I was like a caged animal, I knew I wanted out of the cage, I just didn’t know where to go when I escaped.

As the years passed by, I traded going to the mailbox with a yearly trip to a Halloween party. Even though it took me years to get it right, I finally figured out how to figure out a “costume” which helped me to build my confidence that I could present well enough to get by in the world as a woman. My goal always became to be mistaken for a woman in a costume, not as a man dressed as a woman and I achieved it. From there, my problem became Halloween only happened once a year, and what would I do the rest of the year about my growing gender dysphoria. My final decision was a simple one, if I had the ability to do it. I would have to manufacture my own reasons to sample the world as a novice transgender woman and see if I had the same positive feedback I received on Halloween. I discovered most of the world did not care about how I was dressed, and I gained the confidence to do more.

I made it to the point where I began my “bucket list” of things to do as a transfeminine person. Or could I do other things that women do in their everyday lives and succeed. Every time I did something such as taking myself out to lunch, or negotiating a bookstore and buying a coffee, I checked them off my bucket list and proceeded to move on to more difficult interactions with the public.

Of course, not everything I did was a success. I was told to leave a venue I thought I was a regular in one night when three drunk guys thought it would be fun to play “Dude Looks Like a Lady” on the jukebox over and over again. Initially it hurt me, until I got my confidence back and found another venue right up the street. My success was complete when the crew of the place I was asked to leave found me one night. They told me the manager who told me to leave was fired for drug abuse and they wanted me back. Retribution was mine as well as a real boost to my confidence. It felt good to be wanted as their token transgender woman.

Even so, to this day, I wonder why my confidence is so fragile. In September, my wife Liz and I are taking another bus tour. It’s our fourth one, and this time we are traveling from Ohio to Boston and then up into New England by train. Even though, I have never had any real problems with anyone else on the trip before, in the back of my head I still worry about some right-wing woman questioning my gender and ruining my trip. I am sure I am just paranoid and should be worried about catching Covid again and ending up in another hospital. Which is how our last vacation ended up. Hopefully I can get an updated vaccine just before we go. Which will build that part of my confidence.

The only way I know to build your confidence is to keep being yourself and improving your presentation as a transgender woman or cross dresser if you prefer. Perhaps it will always be fragile like mine is and it is something we always will have to deal with. One thing is for sure; you cannot build it by hiding yourself away. Expect some setbacks and keep moving forward as you are building a new future. It is a huge step forward. Having nice fashion and applying beautiful makeup is wonderful but it all means nothing if you do not have the confidence to pull the picture together. Humans are like sharks and they will know something is wrong if you let them.