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.

Just a Man in a Dress?

 

JJ Hart (left) with wife Liz.

Just a man in a dress has been used to describe me in my past.

I suppose it was true to an extent when I was a part-time cross-dresser. But it all changed when I finally grasped the idea, I was so much more than a cross dresser, I was transgender. Ironically, the idea came to me out of the blue one night when I was going out to be alone. As I was applying my makeup and getting dressed, it occurred to me that my life was different. Instead of just wanting to look like a woman, I wanted to interact with the world as a woman. The whole idea terrified me, but I knew if I was successful, my life would never be the same again.

To be successful, I knew I needed to be very careful to blend in with the professional women I had seen previously in the venue I chose for my grand experiment. To scout it out, I went there as a man to get my potential timing down. Once I did, it was time to try to increase my confidence and calm the major fear that I had that I would be called out as a man in a dress. Looking back, I think I sat in my car for a half hour adjusting my makeup, before I gathered the courage to go in. Making a long story short, I was successful and managed to even stay for an extra drink before I left and I was right, I knew my life would never be the same again. I had crashed through my cross-dressing barrier and landed comfortably in the transgender phase of my life.

As I changed, I had the baggage of two worlds to bring with me. One was my past as a man and the second was my experience as a crossdresser. Of the two, my male past was the most difficult to shake, mainly because I had worked so hard to maintain it. I desperately did not want anyone to see I was feminine at all. It turned out I was so successful portraying a man, that everyone I knew was surprised when I transitioned. It was difficult to explain to them I was so much more than a man in a dress, I was a transfeminine person. Then I needed to explain what I meant about that. At that point, I found actions spoke louder than words and they had to see me repeatedly as my dominant feminine self to understand where my life really was.

These days I am so fortunate to be surrounded by people who accept me for who I really am, so much more than just a man in a dress. They shield me from all of the evil stupidity coming down from the orange felon and his minions in the white house. I feel so sorry for the transgender troops who were loyal, qualified members of the miliary who lost their jobs out of ignorance. You all know how I feel about what is going on in Washington, so I don’t have to repeat myself, and ruin this post.

As far as the day-to-day world went for me, I discovered I was remembered easily, so it was not too difficult to begin to build a new feminine person from scratch. I needed to decide on basics such as wearing the same wig and using the same name to get me by. What I was doing was changing wigs and names thinking the process would help me pass magically as the woman I so desperately wanted to me. What I learned was, there were no shortcuts on my male to female transition path. If I was going to make it to my goal of living fulltime as a woman. I also quickly realized, once someone saw me a couple times as my authentic self, they knew I was much more than a man in a dress.

My disclaimer in all of this is, I am not in any way putting myself up on a pedestal and saying I am better than a cross dresser. On the other hand, the opposite is true. I appreciate the time I spent crossdressing. The whole experience taught me so much. Perhaps the biggest lesson was I could make it to my dream of transgender womanhood if I worked hard enough. I most certainly did not think at any point my journey would be as complex as it was. I found to be successful; I needed to be better in life than the average cisgender woman who had huge benefits on me from growing up female. Catching up proved to be difficult to do as my gender workbook was blank. As I always say, I am not taking all of the credit for my success and putting myself up on some crowded pedestal. I found cisgender women to help me.

They realized early I was so much more than a man in a dress and stepped up to help me into their world.

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 Evolution

 

Image from Kyle
on UnSplash.

After all these years of pursuing a male to female gender transition, I view the process as evolution.

I am biased, but I think I have been fortunate to have lived through all the ups and downs of gender dysphoria to be able to have an up close and personal look at how both of the two main binary genders live. Similar to being able to actually live on the economies of Thailand and Germany when I was in the Army during the Vietnam War. By living on the economy, I mean I received off base housing and food pay from the Army, so I went on base only to work. Seeing how other societies work did wonders for my young self.

It took much longer to do the same thing when it came to my gender issues. I knew they were always there from a very young age, but I had no help to discover what my issues really were. I needed to live my life as a transgender woman to learn what I needed to do to achieve my childhood dream of living as a woman. No being a doctor or lawyer for me, I wanted to be a woman. At the time, I was naïve and thought all I needed to do was work on my appearance in the mirror and I could reach my dreams.

As my gender evolved, I needed to evolve as a person with it. What kind of a woman would I become became a major issue. I could be a standoffish bitchy woman, or a worldly feminine being who enjoyed being herself in the world. Ironically, my male self-helped me to arrive where I wanted to be. He had over the years provided me with ciswoman role models to look up to and try to evolve into overtime. When you added a potent mix of male and female into my personality, I ended up with the perfect mix. Even though I was appearing more and more as a female, my old male self-provided me with a firm base to evolve.

One aspect I do not want to underplay is how long it took me to do all of this. As I evolved, I began to make mental mini bucket lists of things I wanted to do in my exciting yet terrifying transfeminine world. The only problem I had with making bucket lists was I was spending too much time in my male life daydreaming of the next time I could be feminine. All too often, my gender lines blurred, and I needed to make sure I kept my male and female lives separate. It was intensely difficult for me to do as I was increasingly discovering I wanted and could pursue a life as a transgender woman I always had wanted to do and still was unable to do because of the male life I had worked so hard to build. The pressure just kept on building as I continued to try new things as my feminine self. I was in an intensely lonely world at the time as I left my closet.

I evolved to a point where I was able to create an entirely new person from the two, I had left behind. I transitioned again from being a basic weekend cross dresser into an accomplished transgender woman who could blend in with the world at large. Suddenly, I went from being shy and backwards to being confident and aware of my surroundings. Which I found I needed to stay safe in my new world. It was then I found many women were curious and friendly towards me while nearly all the men ignored me. Which I had no problem with as I had evolved past caring what they thought.  They had kicked me out of the men’s club.

As I look back at this time of my life, it seems to be a blur of activity.  Since I had changed my gender outlook in the middle of my life, I was learning from watching my new women friend’s what life was all about. Primarily, since most of them were lesbians, I found I did not need the validation from men to feel good about myself as I fit in with them. Evolution felt so good, I wanted more out of my new life. Again, I was fortunate when my wife Liz approached me online and we struck up a love affair which lasts till this day. I never thought I would ever find someone to love me as a sixty-year-old transgender woman at all, but I did.

My final evolution turned out to be wonderful, and I understand now why all the gender bigots hate us so much. We transgender women and trans men have had the chance to do what they never have had the chance to do. Experience both sides of the binary gender experience. The haters will just have to work their way through it. We have evolved and they have not.

 

               

Dressing for Success

 

Image from Mohammad Nadir
on Unsplash. 

During my earliest days when I was forced into being a boy, anytime something negative or even challenging happened to me, I would run home and seek solace in my soft and colorful feminine clothes.

Soon I called the cross dressing I was doing, dressing for success. Mainly because I felt better as I did it. The sad part was, very soon the feelings of gender euphoria went away, and I was back in my unwanted male world where I was expected to succeed. During that time in my life, I was able to barely keep my head above water and still slowly improve my feminine basics in such things as the makeup arts. I guess all those hours of watching my mom apply her “face” as she called it, came back to help me. This was the 1950’s when women took their appearance much more seriously than today. All women were expected to dress for success.

As I barely stayed afloat with my cross-dressing challenges, it soon became more evident to me that there was much more going on with me than met the eye in the mirror as I tried to appreciate myself. It was about that time, when the internet showed up, and I was able to research terms such as gender dysphoria and transgender. Suddenly, I discovered who I might be and certainly found I was not all alone. It all started to make sense why my urge to cross dress never really seemed to go away. It was always with me in the back of my mind.

Soon, as I joined the world as a novice transgender woman, dressing for success largely depended on if I could go out into the world and blend in. I began the easy way by trying my hand with shopping mall clerks who for the most part were only nice to me for the money I needed to spend so I could be more fashionable and feminine. From there, I branched out to challenge myself by stopping to eat lunch and face servers one on one to see how I did. I did well, and very rarely did I have to run home and wonder what I did wrong and go back to my gender drawing board. I did not realize it but what I was doing was replacing my mirror time with time in front of the public. A very valuable learning experience as I discovered venues such as coffee shops, bookstores and even antique malls where I could shop and relax.

Each experience helped me to learn more about myself as a transfeminine person and then dress for success from it. To quit being so flamboyant with my wardrobe and wigs became my new goal as I was settling into my new life. People began to know me quicker, so I needed to be better in my approach to dressing for success. I learned I did not have to lose any of the enjoyment I experienced as a trans woman; I just needed to follow the lead of the cisgender women around me. I did not necessarily have to dress down for the grocery store and up when I mixed with the professional women out for a drink, but it helped me to feel better and relax. Plus, heels and hose would have certainly not worked when my lesbian friends, and I got together.

At times I even took my dressing for success to the extremes to be able to judge what the public was thinking of me. I used to wear my best sunglasses so that strangers could not see my eyes and tell I was looking at them, but were they looking at me? And one of my favorite “props” to use when I went out to be alone was my cell phone which I always had handy when I turned out to be the only woman at the bar. That way, I was trying to show anyone else I had someone else on the way, and I was saving their seat.

To be sure, dressing for success as a transgender woman was always a more complex process than doing it as a man. From undergarments to accessories such as jewelry, wigs and purses, women naturally lead a more layered life which can be reflected in the way they dress. I certainly had many more compliments on my outfits as a woman than I ever did as a man. Primarily, it was because it was something men never do and often, many cisgender women used compliments as simple conversation starters when they were curious about me.

As with all cisgender women, dressing for success is something transgender women must learn. The problem being we come from such a vastly different background to do it. Almost none of trans women had the benefit of peer pressure and a mom to guide us through the initial makeup process. Our workbooks were blank when we started our gender journeys. Playing catchup was not a fun game to play for me as I found making up my face was different than painting model cars. Most certainly, dressing for success was a lifelong experience for me.

 

 

Why Would I do this to Myself?

 

JJ Hart, Club Diversity
Columbus, Ohio.

Even though it has been years since I have been asked the question which asks why I am transgender, I withheld all my sarcastic comments such as I found my gender dysphoria in the bottom of a cereal box and thought of a concise truthful answer.

The truth is I had always known but was afraid to accept it. In the meantime, I set out on a slow, often torturous process to reach my impossible dream. To all the naysayers I interacted with, I just wanted to say, if I was not serious about switching male to female lives, why would I do this to myself. I knew early on I brought a lot of the problems with the public I faced on myself because of my novice attempts at presenting myself to blend into society with other women. I was coming off like a clown in drag, rather than someone who was seriously trying to jump the gender border from male to female. I was not playing around.

As my old male ego suffered, my feminine ego persisted and finally I did better in the world. I think too, the world took me seriously for the first time and did not have to ask the “why” question. I discovered too, that most of the world was just doing their thing and could care less about me if I could just blend. As I did blend in and began to carve out a new life for myself, the “why” of what I was doing became more personal and pressure packed. I was risking a successful male life I had worked hard to achieve, in order to live a new life which was so scary and at the same time felt so natural. I was having fewer people ask me why I was doing this transgender trip to myself.

Which brings up the question why any of us would transition ourselves if we were not desperate to do it. As an example, my own personal example was all the self-destructive behavior I put myself through including suicide and alcohol abuse. I was a living example of why I would do all of this to myself to be a transfeminine person. I was serious about what I was doing and needed to continue up the gender path I was on.

What helped me too was when I began to see the same people more than once. Since I was easy to remember, strangers began to put a name to my face, and I began to become a regular in several of the straight venues I went to. I just followed my tried-and-true idea of if I was friendly, did not cause any trouble and tipped well, I would be welcomed repeatedly.

The farther I went along my gender path, I began to wonder what sort of a transphobic gender bigot or female TERF would even question why a transgender person does what they do. Such as making all the sacrifices we must make to live the life we desire such as risk losing family, spouses and employment. Slicing off a major part of our life and starting over is intimidating enough without the naysayers questioning it.

On the other hand, there were things I wanted to do to help my feminine transition along such as losing nearly fifty pounds and beginning to take better care of my skin. Suddenly, I had access to more fashionable clothes which fit better, and my makeup was easier to apply. All because I took the time to take care of my transfeminine self. When I did so, even the haters I still encountered needed to get over it because I was more secure in myself. Even though I was increasingly successful in the world as a transgender woman, humans are like sharks, and every now and then I needed to fend off any unwelcome attention I might have attracted.

Possibly, the most important answer to the “why” question came when I decided to seek a doctor’s help and begin gender affirming hormones. Naturally, the decision on HRT was a major one and not a decision to be taken lightly. At the time I started hormones, I was leading a healthy male life which would have to change. I knew all along, I had come too far on my gender path to turn back now and quickly learned I had made the right decision to start HRT. My life blossomed as never before, and I never missed my old male body and emotions again.

By this time, I had married Liz and settled into a transgender dream world I never thought I could achieve. I guess I was to the point of if I could dream it and could do it. Which is a topic for another blog post altogether.  Plus, I had answered the question once and for all of why I wanted to do this to myself. It was fulfilling my own personal destiny.

 

Fight or Flight?

 

Image from Anna Deli
on UnSplash.

As a man, fight or flight became very important to me. Primarily because I needed to become the protector of the loved ones around me and myself.

To be clear, I was never much of a physical fighter, but as I grew into manhood, I was not shy of confrontations either. I could use my size and or male knowledge to back off most potential opponents. For the most part, it was a straightforward proposition. Rule, or be ruled.

Of course, when I transitioned from my unwanted male life into a new exciting feminine world, my idea of fight or flight needed to dramatically change, before I got hurt.

Not too long ago, I had a question from one of my readers asking me what the most important male privilege that I lost was. I replied, the loss of my personal security. I found out quite quickly how dangerous men can be to women a couple times right after I transitioned and left myself in compromising situations around toxic men. I was fortunate my second wife was around to bail me out the first time and I was able to spend my last five-dollar bill to pay two guys off to leave me alone on the second. The best five dollars I had ever spent! (There probably should be something to the effect I was cheap but not easy brought up too!)

All kidding aside, escaping these situations taught me valuable fight or flight lessons. Gone were the days of out bluffing other men in potentially harmful situations, and in were the days of planning ahead to stay out of situations which could cause me trouble. Keep in mind also, I was spending most of my time out to be alone in those days, so I as completely alone as a transgender woman. If I passed as a cisgender woman, was I in better shape than if I was read as being a trans woman. There was no good alternative, and I always kept flight ideas in the back of my mind if I needed them. I think one of my biggest paranoias was having some bigot sneak up on me from behind and pull my wig off. Which never happened.

Through it all, I suffered from not having a girlhood to grow up in where I could learn the lessons all cisgender women know. Such as doing their best not to find themselves in dark unlit parking lots alone. Following my close call on a dark city street outside two gay venues, from then on, I had a trans man friend of mine walk me to my car to be safe. It was a different experience to be sure for me, but there was/is safety in numbers when it comes to leaving your male safety privilege behind.

When it comes right down to it, your fight or flight chapter of your gender workbook needs to be filled out quite quickly. I know several transgender women who carry weapons in their purses for protection. Even though I was infantry trained on weapons in the Army, I choose not to arm myself because of the fear of shooting myself. My wife Liz and I have talked about the possibility of buying pepper spray as a deterrent, but we just don’t really go anywhere where we could be in danger of using it. So, we have not acted on any moves to arm ourselves yet. Plus, Liz went through some intensive martial arts training several years ago which she could use. There is a plan for us to use if we have to fight in an increasingly toxic world in which I am just about totally worthless at the age of seventy-five and with mobility issues. Ironically, I have experienced yet another full circle moment in my life as I have gone from a fight-first mentality, all the way to a flight first priority. I guess it comes with the territory of being a senior citizen transgender woman.

Whatever the case is for you, please be careful in whatever path you choose to go as a transfeminine person. Just use your new feminine wiles to help you stay safe just knowing it is a possibly toxic world depending upon where you live. I have an on-line acquaintance who lives in rural Tennessee who has been slowly coming out in the recent months, and by sheer willpower, she has chosen to stay and fight for her existence. It takes a lot of courage to say to one of her neighbors who threatened her job by saying she was transgender, to get over it, but she finally did. And she still kept her job, so it is possible to fight instead of fleeing. As I said, just be careful if you do it.

I think the worse bigots to fight are the Bible thumpers who want to quote scripture to you. I am far from a biblical scholar and can never remember a rebuttal to use when and if it ever happens to me. It never has because I would have to fight not to flee the situation.

 

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.  

 

  

The Second Time Around

 

JJ Hart (middle) at my first
Girls' Night Out. 

If you are one of the rare human beings to experience a second time around in life, you owe it to yourself and others to live it the best you can.

Being transgender can give you that rare insight into two of the main binary genders which should give you an edge in dealing with the everyday world. Having an intimate knowledge of whatever the other gender maybe thinking of us as trans women or trans men brings out fear in the public's eye. Who are we to possess such a wonderful scope of knowledge anyhow? It is especially bad with the male gender who has such a poor grasp of their sexuality to begin with. I know when I transitioned from male to female, one of my main concerns was my own sexuality. Was I expected to suddenly change my sexual preferences which had always been with women and suddenly start liking men. I even went to the point when I first came out when a straight woman friend of mine told me to buy bananas and practice. I will let your imagination do the rest.

We all know though there is so much more to a gender transition than sex when you set yourself up for the second round in life. I found I was leaving a life as a man where I was mildly successful and entering a totally new world full of women who were able and willing to question my existence in their world at all. Away from men, the women were a complex tribe, and it was difficult for me to be given the access to play with them behind the obvious gender curtains. First and foremost, just looking like a woman just got me in the game and the difficult part was just beginning. I spent hours and hours in the world just learning how to be the new me.

Suddenly, before I knew it, the doors to a totally different world opened for me and I was invited to the girls’ night’s outs. The invites could never replace the learning experiences young girls have when they are in their formative years and they get to go to girls’ overnighters with friends, but they were all I had to attempt to catch up on my gender homework. No chance to experiment with makeup or gossip about boys or other girls.

The main problem was, I had another male life to deal with at the same time. Looking back, I don’t know how or why I put up with all the gender stress and tension I did to make it to my dream. I guess the reason was I did not have the confidence to know if I could make such a major life changing step at all. We all have a lot to lose when we undertake such a step, don’t we? Plus, as I slid towards the idea I could live fulltime as a transgender woman, I was being accused of being selfish. Which made me feel guilty until I finally came to the conclusion I was being selfish. Because I had to save my own life.

As I was accepted into the girls’ sandbox around me by the majority of the women around me, my confidence grew that I could indeed live a second time around life as a transfeminine person. My long hidden inner female took over and surprisingly became a rather social person as I formed bonds with my small group of lesbian friends which was the best of all worlds for me. As I always say, the first and main thing my friends taught me was I did not need a man for validation. Which included my sexuality. All I needed to do was still keep an eye out for the rare bigot who hated me for no real reason. It turned out the haters would have to go through my cisgender friends to get to me, if they wanted to.

At that point in time, I met my wife Liz, and my second time around became easier and easier for me to live up to. I say live up to because I found myself at a point where I always dreamed of being. But I never thought I could make it. Never say never became a reality for me when Liz told me she never saw anything male about me. I was in gender heaven and stayed there until I realized what a heavy burden I needed to face. Here I was with the rare chance for a do over in my life and to not repeat the same mistakes I made as a man.

So far so good I think as I head down the stretch run of my life and I can be thankful for the chance to live two lives regardless of what the gender haters say.

 

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.

 

In Over my Head

Image from Alexander Mass
on UnSplash

In the beginning, it was all so simple. Pick something, I could squeeze into from my mom’s closet, try my best to wear her makeup and go from there. Very quickly though I found I was getting in over my head as I began to sink into my own personal gender quicksand.

My first problem was hiding my small but growing collection of feminine fashion. In addition to my parents, I had a slightly younger brother I needed to deal with. Somehow, I managed to keep the darkest and potentially most destructive secret I had away from him, I wanted to be a girl in the worst way. I had no way of knowing then how many times I would be in over my head as I chased my dream. Primarily because I had no way of knowing looking like a woman was just the first step of a lifetime of gender learning. As I like to say, my gender notebook was blank when I received my copy, and I needed to catch up the best I could.

I began by studying the women around me who were my age the best I could. It was all I could do at that time to keep myself from setting myself up for failure when I finally was able to escape my dark, lonely gender closet and explore the world for the first time. When I did, I was naïve and confident I would have no problems. After I was sent home crying after being laughed at, rudely I knew I was in over my head with a lot of work to do. For some reason, for the first time in my life I knew I could not give up and I refused to quit. I kept going back to the drawing board until my makeup art improved and I began to learn the benefits of dressing my self properly as a woman of my age and build. Suddenly, I began to pull myself out of my quicksand and began to move forward again towards my dream of living as a transgender woman.

Ironically, as I moved forward, I ran into many other obstacles in my way. Was I pushing myself into a world which was ready for me or not was one of the main questions I had. The more involved I became in the world as a trans woman, the more I needed to be accepted into women only spaces. The only way I would ever know was if I could conquer my fears and try. As I pressed on, somedays I was more successful than others, but overall, I found I was accepted by other women. The times I found myself in over my head as a novice transfeminine person were primarily when I was approached improperly by men. There were times I needed to run home and rework my gender notebook after close ugly calls with men. I learned quickly, those close calls did not validate my worth as a woman. They did provide me with an insight of what women go through in their lives and I learned fast.

As I was adjusting to the new life I was destined to live, It seemed as if the lessons I was receiving kept coming faster and faster. I learned from my lesbian friends how to validate myself as a woman and from men, what not to do. At no point in time was any of my life easy at this point, but it was scary and exciting at the same time. My dream became so close I could reach out and touch it. If I kept out of the quicksand and kept my head above water, I could make it. The hardest part was still yet to come as I was coming increasingly closer by the day to separating from the male life I resented for so long.

The final decision to change was brought on by my choice to seek out gender affirming hormones or HRT. As I urge everyone to do, I sought out medical approval before I went down the radical path I was on. I was approved, put on an initial minimal dosage and before I knew it, changes were happening which made me a highly androgynous person. One look in the mirror told me that I had made the right decision and I wanted to move past the minimal dosage of HRT I was on.

I can’t say I haven’t found my way in over my head in recent times because of the type of person I am. Did being transgender aid in it? Who knows. We all have our choices to make, and they are all tempered by the people around us. Some are fortunate and have discovered feminine gatekeepers such as spouses were there all along. While others are destined to go it alone. Whatever the case, try to not get in over your head and do the best you can.                                 

  

When Who You Are is Against the Law

 

Kim Davis wants YOUR Rights.

Yesterday, the spineless governor of my native Ohio agreed with the felon/pedo in chief tRumpt to send national guard troops to Washington DC.

The move was a stark reminder to me of how close we are as a nation to a fascist state with a dictator in charge. And, on the battle lines are transgender women and transgender men who at least here in Ohio have watched as our rights have been taken away by a heavily gerrymandered Republican legislature who prefers doing its dirty work under the late-night cover of darkness.

I am extra paranoid because I vividly remember the gay/ cross dressers being rounded up in police buses when I was young in Dayton, Ohio. I certainly don’t want those times to return for myself or especially for my transgender grandchild.

Especially horrific are the Caitlyn Jenners of the world who insist on supporting the regime in Washington. Obviously, they never really learned how it was to have their rights taken away. Perhaps you noticed, I refused to refer to Jenner as “she.” Recently, on a popular social media site I am on, a rather spirited (to say the least) discussion about cross dressers and transgender women. The moderator waded in with some sort of a statement that cross dressers cannot be transgender women and tied the discussion all in with the male privileges CD’s refuse to give up the way trans women have. Then used Jenner as an example. Being smart for a change, I stayed completely out of the fray. Almost.

I did use the example of the cross dressers and/or transgender women I knew who were strong orange felon supporters. I will never understand how they could throw themselves or the trans community under the bus and keep doing it. Their excuse was, he couldn’t be that bad. Well, he was.

Then there are the comfortable gay and lesbian tRumpt supporters who sat back in their shells and thought all the misery being brought upon the transgender community couldn’t happen to them. Now Kim Davis is back asking the corrupt supreme court to formally destroy the same sex marriage ruling the gays and lesbians celebrated so many years ago. Now their refusal to get totally behind the transgender community in our time of need is coming back to haunt them. It could and would be coming around again.

I know one of the problems with this post is I stereotyped too many people along the way. I know many in the gay, lesbian, and cross-dressing community who don’t support the sick felon and do support the trans community and that is powerful because we need everyone behind us in these desperate times.

Just imagine if you are a novice crossdresser trying to decide if you want to attempt to jump out of your gender closet and are afraid of being arrested. It’s uncomfortably close to happening in states such as Ohio. The midterms are coming and make sure you vote from your closet for the right candidates.

On the bright side (and there always is one), there are pockets of support in major cities around the country. If you are struggling, try to find a LGBTQ support group to help you come out. In the meantime, buckle up for a rough ride and stay safe.

Sorry for the rant, sometimes I just have to vent.

Not the Man I Used to Be

 

Image from Ava Sol
on UnSplash.

Almost daily, I feel as though I am not the man I used to be, and it feels great!

In many ways, I was a man’s man as I went through life desperately attempting to survive in a male world. To do it, often I needed to bluster my way through life confronting other men I met. Although nearly all my confrontations fell way short of being physical, I still was able to win more than I lost. As I said, I hated the life I was living because deep down it did not feel right.

While being a man’s man took the life right out of me, it seemed being a transgender woman put it back. As I settled into my own woman’s arms, I instantly felt better, and I did not care if I was no longer the man I used to be. However, what was easy in the beginning became increasingly difficult as I went along up my gender path. It seemed like each wall I scaled on my path was a little higher as I stopped to look around to see if I still wanted to keep going.

By now you know I never stopped moving away from the man I used to be, and I had many lessons to learn. Particularly around personal security which I always took for granted as a man. I was always over average size, and people usually left me alone. It got to be so bad I couldn’t even scalp tickets to a football game I wanted to attend with my wife. The illegal scalpers thought I was a cop and would not sell to me. I had to let my wife approach them as the tickets were not illegal but where they were selling them were back in those days.

Other aspects of life I hated about being a man was always having to make the first move. All the way from being the one asking the woman out, all the way to where we were going for dinner. Then being told somehow my choice was wrong. Through it all, I could not wait until I was the one who did not make all the decisions. It was all I did at work, and I felt I shouldn’t have to at home which did not work well with my wife. On the other hand, I did learn always being the one who asked someone out was not the popular way to go with everyone. Just waiting around to have someone ask you was just as bad for the woman.

Finally, as I began to put all of that behind me and was beginning to put together a new life as a transgender woman, my life as a man began to fade in my rearview mirror of life. Not being the man, I used to be a welcome change and was where I was headed anyhow. I was trying to find specific small things I used to do as a man and change them over to feminine ones. Large examples included how I walked all the way down my gender path to learn how to better use the nonverbal communication women routinely use between each other. Very quickly I learned how one glance from an employee at a regular venue I went to meant I was in possible trouble if I stayed. In an instant, my gender world changed as I knew I could not stay and fight my way out or try to neutralize the situation with a male scowl. So, I picked up my purse, paid for my tab and left. Along with my male ego. 

Then there was the ultimate challenge to any remaining masculinity I had left. It came when I was approved for and started gender affirming hormones. Very rapidly, HRT caused what was left of my male strength to fade away. I used to put trucks away in my busy restaurants all the time and move very heavy beer kegs around with no help. Not a chance of that ever happening again since I was on the hormonal medications. As I learned I was not the man I used to be, my body started to change, and androgyny began to set in. All before I made the fateful decision to give away all my male clothes and live fulltime as a transgender woman.

For me, deciding to never go back to the man I used to be was a simple decision I should have made years before. Out of all the decisions I had to make as a man, I was unable to make the biggest one and set my life in the right decision…away from the man I never was.