Trans Girl in a Wig Store

 

JJ Hart Blonde Look.

Perhaps I should say trans girl in as many wig stores as she could find. 

Once I arrived at the point where I could even afford a nice hairpiece, I was like a kid in a candy store. So many styles of wigs to choose from and so little time to try them all on. I wish I could say I quickly became better at the process of choosing my crowning glory. Sadly, similar to the rest of my outfits or fashion, I was going too trashy to blend in with the women in public. I was telling myself since I needed to overcome a large head and body, I needed large hair to do it.

Also, to find a wig store I had not been to, I needed to drive long distances. Primarily from my medium sized hometown which had no stores which specialized in wigs all the way to Dayton or even Cincinnati which had several. 

Once I made the trip, I needed to learn several of the shop owners were not really interested in how I presented in new hair but were very interested in how much I had to spend. The owners could not do much to direct me in the proper direction of what I needed to look better as a transgender woman. Being fair to them, my male ego was in the way, telling me how to choose because he thought I would look better. Many times, I ended up buying what I today call clown wigs which were guaranteed to get me recognized or clocked as a cross dressed man. The wigs were good for Halloween and not much else.

All in all, the choices were bewildering. I felt as if I was back in my beginning days in the makeup department when I was attempting to figure out what product I wanted to try. In the wig store, I had to choose a color of hair I wanted, style I wanted and even which hair I wanted, human or synthetic. The possibilities were endless. 

In the beginning, my default color was always red or auburn before I started to shift away to other shades. For years I rotated between dark colors and blond which became my favorite. I was enjoying the changes in my appearance until I needed to settle down into one look when people began to recognize me. No more changing my name with my wigs. Settling down was difficult but something I needed to do as I followed my path to transgender womanhood. 

Through the magic of gender affirming hormones and good genetics, I arrived at the point where I did not need to wear a wig at all. In fact, one of the best gifts I had ever received came from my daughter when she provided me with a visit to her own upscale beauty salon. Even though  the experience was terrifying at first, I ended up loving it and could not wait to go back. Almost immediately I understood why cis women spend so much time and money at their salon. 

Most certainly, I cannot overstate the importance of hair to our outfits and fashion as transgender women or cross dressers. Hair demands all the effort we put into it. 

Ditching Good for Better

 

JJ Hart with Ohio River.

As I made my way along my gender path, I was always looking to go from just good to better. 

I always wanted to present better as a girl my age all the way to moving like one and even doing my best to act like one. I did my best to be a keen observer of what the feminine gender around me was doing at all times.. If they were wearing mini-skirts, so should I was a prime example.

Sadly, I was hindered by my meager financial situation until I grew older and could afford more fancier accessories such as clothes and wigs. Even still, nothing was stopping me from pursuing my gender dreams of living as a woman. If only I could. That is where my path became more and more important. For example when I finally broke out of my closet and did all my own shopping, I learned the hard way what looked good on me and what did not. From there I could build on to my success and go from good to better.

I became especially good with my feminine business attire wardrobe. At thrift stores I managed to find a black pant's suit which paired nicely with heels or flats and my should length blond wig. I even had a wool full length coat to go with it for the winter time when I went shopping. For the warmer times of the year, I found a lime green business suit with a shorter skirt which I paired with pastel green opaque panty hose and matching kitten heels. I found I went from good to better either time of the year and presented relatively easier for the first time in my life. Gender euphoria at it's finest.

All of my fashion advances did not prepare me for face to face encounters with other women in the world. Chance encounters with store clerks were easy until I began to stop at restaurants to eat. I needed to order from a menu while at the same time doing my best to sound like another woman just having lunch away from her job. Until I gathered the confidence to practice it, the entire idea of talking like a woman was once of the most difficult things I had ever attempted.  I even went as far as going from good to better by taking vocal lessons to usher me into my transgender womanhood. 

I often think I inherited my drive to always do better from my parents. Nothing was ever good enough for them. If I had received a B in a class, why did not I get an A was the routine I grew up with. Imagine the irony my parents would have felt when they found I applied the same thought pattern to a gender issue they were very against. All I ever wanted was to be a woman, transgender or not and needed to work very hard to overcome my male bonds to do it. Plus I always felt if I was going to be successful as a transgender woman, I would have to try harder than the average woman to succeed. 

So along the way, I needed to not accept good and kept trying to achieve being better and better as a transgender woman. I wonder what my parents and my second wife would have thought of me now. Hopefully they would be happy for me, since I have arrived at the place I have always wanted to be in life. If I had done it sooner, I would have undoubtedly been an easier person to live with. 

The Second Time Around

 

Image from JJ Hart.

Not many humans have the opportunity to stop their life and begin again as a new person unless they are up to no good.

Perhaps it is one of the reasons so many people do not accept or try to understand the transgender community. Or then again, they are secretly jealous. Regardless, it is up to all trans women and trans men to attempt to live their second life to the fullest. 

Often, living a transgender life is easier said than done. We all have to remember all the opportunities in life we needed to give up to achieve our gender goals. Opportunities some take for granted who are not at risk of losing spouses, family or employment. I know in my case, any or all of the chances to lose everything was a very real deal. I was fortunate when I lived long enough to see destiny re-open closed doors in my life.

Following a very dark period of losing loved ones to death, just in time I was able to find others to fill the void as I was so very lonely. In many ways, I was a social creature and if possible I wanted to remain that way. Naturally, when I started my path into transgender womanhood, I needed to learn and perfect an entire new set of feminine social skills. It was all so very intimidating. Especially when so many women wanted to know more about me and what I was doing in their world. It was a shock to my system how different my world became so quickly. Gender learning became a priority over just going out to be by myself. 

Deep down I knew I had to learn from my first go around in life as a man and learn from it. Even though I was never a toxic male, there were instances of life I would like to have back. Such as the times when toxic males were attempting to have their way with women. What I did do was observe how women handled it which helped me out in the future. 

All in all, following several rough patches at the beginning of my new life, the second time around was exciting yet terrifying to me. Primarily because my inner feminine soul was just waiting to have her chance to take over my life. It turned out, she was not scared at all. It was my old male self who was frightened about losing his life as he knew it. 

The whole process set into motion a secure second time around in life for me. Being secure led me to a new found confidence in life I had never know before. At the age of sixty, I was able to begin gender affirming hormones and really kickstart my second time around. External changes to my body helped me to present better in the world and internal changes helped me to feel much more femininized than I had ever had before. 

Most certainly, the second time around for me opened my eyes to a life I only had dreamed of. Destiny allowed me to accomplish my dreams and all I needed to do was reach out and grab it.     

Running and Hiding

Image from JJ Hart archives,

I spent over a half of a century in my life running and hiding from the gender issues I faced all of the time. 

First, most of the time I hid my desire to dress like all of the girls around me. Of course, in order to accomplish anything, I needed to suppress any urges I had to be at one as a girl in the mirror. My Mom never knew how much she helped me in my early days of cross dressing. Before I outgrew her, I took advantage of wearing her fashion wardrobe, not to mention her makeup too. Much pressure to hide to be sure because if I was discovered, intensive therapy or worse would be in my future.

Also very early on, I ran to places I thought I would be safe. I hid a collection of clothes and makeup in the woods beside our house in the country. In my own world, I could escape my brother and family and briefly enjoy my small attempt at gender freedom. On other very rare occasions, when my family was not home, I escaped to the bathroom and applied my clothes and makeup which was an ideal time to see myself in the full-length mirror in the hallway.   

As I grew older and my male life became more complex, running and hiding became much more difficult. Plus, I had so much more to lose in my life if I was discovered. The more I ran from my issues, the more pressure I faced. What happened was, after I was freed from the restrictions of my military service, I was able to run harder hoping to free my gender issues even better. I changed jobs and locations frequently trying to outrun my life and for the most part was more miserable than ever before. I moved my small family to the suburbs of New York City, then back again to my native Ohio. Along the way, we lived in an old farmhouse in rural Southern Ohio and back again to urban areas such as Columbus, Ohio.

Sadly, it took me many years to understand all the running and hiding was doing me no good. The problem was inside me and could not be out-ran and was mentally exhausting.  Once I learned the solution to my problems were closer than I thought, my journey to transgender womanhood became clearer but in many ways no easier. I still needed to strip back all the layers of femininity and do my best to cross the gender border. I think now, the communications I had with the world as a novice transgender woman were the most difficult part of the journey. I needed time and effort to overcome the fear I had with looking another women in the eye when we spoke. For the most part, I just wanted to run and hide. 

Every time I did not run, I developed more confidence in myself. In other words, with the help of other cis-women friends I had, I found and embraced my own transgender womanhood. No longer was I stuck in an old male life I never really wanted regardless of all the privileges I had accumulated from just being older and white. 

Running and hiding just became too exhausting and demanding to continue with it. I finally gave into the pressure and began to live in my truth. What took me so long. I still wonder. My male life just wasn't so much fun and successful to continue. I consider myself one of the fortunate humans to escape the bonds my gender roots had confined me with.    

Trans Girl in a Sports Bar

Archived Image, JJ Hart with wife Liz on left 
and daughter  Andrea on right. 

 I have documented several times how I came to be accepted as a regular in a couple sports bars I was familiar with as a guy.

In many ways I was forced into the path I was taking. I did not particularly enjoy the atmosphere I was facing in the male orientated gay bars I was going to. I did not like the music usually and especially did not like it when I was treated like a drag queen. Even though I was not dressed extravagantly like queens did. 

As time went by and I tired of even fighting for a drink at the bar, I decided it was time for a change. To do so, I decided to go back to what was familiar, if I could do it. To be sure, I needed to find out if I presented well enough to get by in a totally new environment except it wasn't. As I previously said, I had been in many sports bars as a guy, so I knew to be friendly, smile and tip well. What I did not count on was how fast I would be remembered in these venue's as a transgender woman. It seemed as fast as two visits in a place, I was remembered and could go from there. Of course the problem was, building a whole new feminine person nearly from scratch. 

I discovered the whole process was relatively easy as I was there to start with to watch the sports on big screen televisions and drink a few beers at the same time. Outside of the staff, I rarely had any interaction with anyone else. 

In the meantime, the lesbian bars I used to go to were disappearing rapidly. For the most part lesbian bars have remained an endangered species until recently. In fact, I saw a story about new women's sports bars which are popping up  now around the country. Without actually mentioning any lesbians by name, it featured one bar opening up by two married women (to each other). In other scenes from the venues, the look of the clientele suspiciously reminded me of the lesbian bars I visited years ago.  

I also was remined of a women's roller skating match I went to with three of my lesbian friends in Cincinnati, Ohio. The crowd that day was overwhelmingly women including me. We all drank one dollar beers and watched women roller skate around and around. Outside of a few side looks, I survived and had a great time. 

These days, with the advent of women's basketball and soccer, not to mention college sports on the regional level, women's sports are really booming. A great time to mesh in your love of sports as a man with your  new life as a transgender woman. It is not unusual these days for a woman, trans or not to be seen in a sports bar and also makes it much easier for transwomen everywhere to carry with them a major portion of their previous lives. I know I was really stressed if I would have to lose my love and knowledge of sports when I transitioned.

On whatever level you consider, even though new women sports bar are not referred to as lesbian bars, they still focus on the success of women everywhere.

Having an Affair

Image from Susan G Komen
on Unsplash

Years ago I experienced having an affair during my marriage  with my second wife. 

Before you condemn me any more than I condemn myself,  the affair I am talking about was with myself. That is right, myself. It happened when my feminine inner soul began to take over my life. What I was doing at the time was rejecting the pledge I had made to her to never leave the house cross dressed again. I became so entranced with how natural I felt in my transgender womanhood, I left the house any chance I could which was often. It turned out, the more exploration I went through, the more I wanted to do. Seemingly nothing was out of reach in the new exciting gender world I found myself in. Sadly, even to the point of leaving the vows I made with my wife behind. 

Let me point out also, I had never stepped away from my marriage during the twenty-five years before to be with another woman. Imagine my shock when I finally did, the other woman would turn out to be me. 

As is the case with many affairs, the passion was real in the beginning. Then begins to lessen overtime. In my case, the opposite happened. The more I explored and lived as a transgender woman, the more I wanted to do. I had a real problem on my hands on what was I going to do. On one hand, my wife had told me in no uncertain terms she would not live with another woman and on the other, I did not have the courage to tell her she already was. If I had faced reality, I would have known it was time to jump off the old male ship and begin to live a new life in a feminine world. Even though most likely, it would have cost me our marriage, perhaps we could have at least become friends in the future if she had lived. You see, she died of a massive heart attack at the age of fifty. 

The only thing I did do out of desperation was try to purge myself of most of my female belongings before she passed away and I even grew a beard. It turned out to be my last tribute to her and the years we had together. 

As with all purges, they don't last for long and one of the first things I did was shave off the beard and turn inward to myself in the lonely tragic days after her death. It took awhile but my inner female took control and let me know everything would be fine. Finally I decided she was right and decided to give up all the guilt I was carrying over the affair I had with myself. 

Once I did, my new life as a transgender woman took over. I found new friends and moved on but it took me five plus years to do it. In the meantime, I found all the work I needed to do to play in the girls' sandbox was worth it. I needed to be better than the average cis-woman to survive in the world I chose to live in. I found a woman's life had so many layers to it, I faced a real challenge. As big a challenge as having an affair in your marriage. With yourself.

De-Transition?

 

Woman's get together. I am on the 
bottom row, far left.

Several posts ago I may have written something which made some readers think I was considering ever de-transitioning back to my old male life.

To begin with, there is no way I would go back to a life I never appreciated. Even though I was mildly successful at living a male life, something was always missing. It turned out what was missing was my feminine soul. The problem was I needed to develop my feminine soul to the point where she could flourish. It took me years to discover the truth with many starts and stops along the way. For years it seemed everytime I took a step forward as a transgender woman then I took a step or two back. The entire process was very frustrating. I was finding out leaving the men's club and entering the woman's club was going to be much more complex than I ever thought. 

Even with all the threats to the transgender community today, the easy way out would be for me to go back to the life I used to have. Also during my life, I have learned taking the easy way out is not often the best way to exist and be true to yourself. Trans womanhood was my true self and when I recognized it, my fragile mental health as well as my life in general improved. So, I knew completely I had done the right thing by stopping the cruel joke I was leading trying to live as a man. The major reason I would never go back to an unhappy existence which led me to alcohol abuse and even a suicide attempt.   

When I transitioned into a feminine world, I finally also learned how to be happy. Something I had never learned how to be. All the time, effort and work I put into relearning how to live made the whole process so worthwhile. So why would I give it all up?

Then there were all the magical hormonal changes I went through when I started gender affirming hominess nearly a decade ago. When I did, it seemed my body took to the changes so naturally and was so ready for change. Even though I experienced many external changes to my body, I also went through major internal changes such as emotional growth. I constantly worry about giving all of the hormonal gains up from HRT if I had a medical emergency or if the government tries to take them away. 

I also had a question from Georgette about the picture I used for the post. She asked if I ever had seen any of the women again and were any LGBTQ orientated. I do keep in occasional contact with two of the women in the group and no I don't think any of them have or had any other contacts in the LGBTQ community. In essence, I was really just one of the girls except for one woman who seemed to really resent me.

I hope this answers some of the comments I receive here. For obvious reasons, I can't answer all of them in a post but I thought the de-transitioning comment was important enough to share. As always I really appreciate all the input I receive. Thank You. 

 

Was there Ever a Plan

Image from the JJ Hart
Archives

Looking back, I needed a very definite plan to follow as I transitioned into transgender womanhood. 

Similar to so many of you, I started by "borrowing" a few of my Mom's clothing when I could still fit into them. I would have added a sister in but I did not have one. When I became old enough to do it, I took on a newspaper delivery route in my neighborhood and combined my new meager funds with the allowance I received at home from my parents and with the money, I was able to buy a few clothes and my own makeup. Since we lived in a rural area outside of town, the plan was to stay a day or two with my Grandma who lived very close to stores *downtown where I could attempt to shop for what I wanted. The problem with the well thought out plan was my Dad worked downtown too and he was the last person I wanted to run into with my new "treasures." 

After I conquered my fear of shopping for cosmetics I did not really need, I was able to buy makeup which did not make me look like a clown. Another problem I had was, the only example I had of applying makeup came when I was able to watch my Mom do it. I wonder if she noticed me watching her. She was probably so entranced in her face, she did not notice I was entranced also. 

The older I became, the more entrenched the plan became. I was able to increase my small "collection" of feminine wardrobe and makeup as I went along and managed to hide it from my brother and the rest of my family. At the same time, I wanted to become better at the makeup arts and finding clothes which fit me. 

At the same time, I became comfortable with how I looked in the mirror and increasingly had thoughts of expanding into the world. I did try to come out fully dressed to one of the very few male friends who lived close by in the neighborhood but was quickly rejected and I scurried back into my dark, lonely gender closet. I stayed in the closet until several Halloween parties began to bring me out. From then on out, my plans really began to change.

During the parties, I learned how much I enjoyed my time out of the closet and I just knew I needed to figure out a way to live as a transgender woman without waiting for a whole year to go by. To do it, I knew I would need to start by telling my spouse what I was up to. So the plan was to find out what wife number one and two thought about me being a cross dresser before we were even married. It turned out wife one did not care and wife two was supportive to an extent which helped me along. 

The main rule I had with wife two was to never leave the house dressed as a woman. I started innocently enough before I veered off course and threatened our marriage of twenty-five years. I began going to women's clothing stores and malls where acceptance was easy to come by. Money was certainly more important than gender. I also would go to bookstores and even antique malls where I could browse with no problems to build my confidence. When my spirits went up, I planned ahead for my next big adventure which usually meant beginning to interact with more of the world as a transgender woman.

To do it, I began to stop and eat at restaurants along the way to make sure I had to communicate one on one with a server or bartender. Since I had an extensive background in the restaurant/bar business, I knew basically what I needed to do to survive. Just be nice, do not cause any trouble and tip well and I could be successful. 

From then on, I endlessly planned on what I was going to to next and how I could challenge myself in the feminine world. Sometimes I was successful, sometimes I was not but I always learned from the experience. In my life as a man, I had never really planned ahead on anything, so this was a big difference. Perhaps it was because I could not wait to try again to live out my dream of transgender womanhood.

*Those were the days of strong vibrant downtowns in many cities, including mine. Before malls took over and they tore the downtowns apart. 

All I Ever Knew

Circa 1940 image
of Virginia Prince

 Every once in a while I receive the question when did I know I was transgender.

The easy answer is I always knew but I needed to figure it all out. The more complex answer is I needed to figure it out after a series of transitions during my life. Two major ones occurred when I made the jump from from a very serious cross dresser all the way to a novice transgender woman. The second problem I had was back in those days, terminology to define a transgender woman or man had not yet been invented. Basically back in the pre-internet days when all we had was the preaching of Virginia Prince and her Transvestia publication which I could not wait to receive in the mail. Seeing all the pretty cross dressers just made me want to do more to improve my feminine appearance.   

I worked harder on my appearance than any thing I had ever done before and slowly began to see improvement over my testosterone damaged male body. It was all I ever knew. 

As I entered my transgender womanhood, I felt deep down inside I was doing all the right things, even though I was jeopardizing all the facets of my male life I had worked so hard to put together. What would I do when my family, friends and bosses discovered my deep secret. It ran so much deeper than just wanting to wear women's clothing. I wanted to be a woman and live a feminine life. 

During that portion of my life, I basically went into attack mode, doing every thing I could to learn how being a transgender woman would affect me. Every free moment I had, either I was out in the world as a woman or day dreaming of the times when I could. Naturally, I learned a lot, good and bad about what life had in store for me if I kept on going towards my gender dreams. I found the grass wasn't always going to be greener on the other side of the gender border as I lost all of my male privileges but hadn't gained any of the female ones. 

Soon I learned, it was truly all I ever knew. Somehow I was born to be feminine and not masculine. Which meant years of struggle to right the gender wrongs I was living. The struggles on occasion were crushing and keeping going was very difficult but I did. Probably because I was behind before I even started. I was born into a very male dominated family which had very few girls to play with. Plus, I never had any feminine characteristics myself to begin with. Add it all up, then include me never having any girl time with anyone all teamed up for a rough start for me on my gender journey.

Even still, my gender path was all I ever knew and staying on it finally made me successful.