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 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.

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.

 

 

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.

 

 

Trans Girl at a Birthday Party

 

An image I took at one of the tables at the
birthday party. 

As I previously wrote about, I recently attended a birthday party for a dear friend of mine who happens to be a transgender woman recovering from a stroke.

For the party, I chose a bright colored red loose-fitting top paired with flats and my paisley patterned leggings. My makeup was a close shave followed by moisturizer, foundation, lipstick and eye makeup for a change. 

The only problem I had was getting my GPS voice navigation to work so I did not have to keep looking down at my phone for directions as I drove on busy highways. Even still, I was able to make it there and back with only three miscues when I needed to turn around. Since my wife is from Cincinati and knows the city well, she normally does all the driving, so I am not used to gathering my courage to do it myself. I was able to calm down and breathe a big sigh of relief when I made it. 

My friend is very popular and had a large turnout of around twenty people in the venue she chose. It was her first time out into the world during her recuperation and handled it rather well I thought. Scattered in the group were five or six transgender women who I had not seen in quite a while. It turned out the cisgender woman I ended up sitting next to was very nice and we had a nice conversation with another woman (cis) across the table. I was a little surprised how the conversation never turned to how we all met the birthday woman, but it never did. She took a picture of the two of us, so maybe someday it will turn up so I will be able to pass it along. 

All in all, I enjoyed myself and was able to sneak past the crowds to see my friend to drop off a card and gift from Liz and me. I could tell she was struggling with all the interaction, so I was able to say hello and goodbye without any interruptions. I came away from seeing her again with a ton of respect for anyone recovering from a stroke and hopefully soon, we can meet up again on the patio of a restaurant we used to regularly go to. One that even I can find!