Wishes were not Enough

 

Image from Delphina Iacub on UnSplash.

In yesterday's post, I wrote about the amount of time I spent wishing I was a girl as I went about attempting to live a male life.

As I pointed out yesterday, I finally arrived at a point where every spare second, I was becoming dedicated to my pursuit of becoming a girl. Which included watching the girls around me closely at school. I was desperately jealous of their fashion and lifestyle. 

As I became older, in order to survive in the world, I put less time wishing I was feminine and adding more time into actually doing it. Which meant of course I needed to unlock the door to my gender closet and try to enter the world as a novice cross dresser or transgender woman. Back in those days, I took a lot of rejection, as I thought I looked like a clown in drag. Stubbornly, I persisted until I could find the right mixture of makeup skill, fashion and wigs. Once I did, my life across a new and exciting gender border became much more satisfying and fun. So much so, I was fooled into thinking my feminized wishes were coming true. 

It was about that time when I hit a gender wall as I found out what my wife was telling me all along, I had a long way to go on my path to transgender womanhood past just looking like a woman. I needed to quit wishing and find out what she was talking about. 

The more I explored the world as a trans woman, the more the world opened to me as gender curtains were pulled back. Of course, I knew cisgender women had their own world to exist in but I did not know how strong and in-depth that world was. For the longest time, my head was spinning as I tried my best to absorb the daily lessons I was learning. Primarily about communication and co-existence with other women on their playing field. Certainly, wishes were not enough when it came to surviving in a woman's world. I found I drew the curiosity of other women who wondered what I was doing in their world, and I had to be better than the average ciswoman just to get by. 

It was about this time; I decided to take a shortcut in my external femininized appearance and research doctors to see if I was healthy enough to begin gender affirming hormones (or HRT). I was, and the hormones almost immediately went about making changes such as softening my skin and producing breasts. All of which helped me to help my presentation skills. Especially, since I did not have any male pattern baldness and quickly was able to grow my own hair out and go wigless. 

I found by this time, wishes did not have to be enough, and I could move up my final transition timeline. Finally, my long-awaited dream could become a reality, and I could put my hated male clothes away forever. Perhaps the best part was, I never wished for him to return.

Forever Dancing

 

Image from Alexa Posteraro
on UnSplash.

During my long gender journey, I often thought there were times when I had finished my trip and made it to my goal of transgender womanhood.

It was during those occasions when life laughed at me and said I better begin dancing once again. As always, I was a terrible dancer and needed to try harder than the average woman to succeed. If I did not, I knew I would never make it.

Earlier in my journey, I thought I was doing enough dancing to get myself by and then hit a solid gender wall when I failed. Any gender euphoria was very brief and fleeting as I went out in public as a novice transgender woman for the first time. On too many occasions, I needed to hurry home in tears after being laughed at (or worse) by the public. Fortunately, I was somehow able to pick myself up and get back to dancing the best I could in my gender game. At whatever cost I needed to do, my first priority was to improve my overall femininized presentation. 

I started by losing weight. In fact, I shed nearly fifty pounds which enabled me to better fit into a wider and more fashionable style of women's clothing than I ever had before. From there, I began to work more diligently on my skin. So, I could wear less makeup. Then I added better wigs to my dance list and finally began to notice a difference in how I was perceived in the world as a transgender woman. By that time, I thought I was ready to dance but I was far from it. All I had really done was carefully craft a feminine image which I needed to put into motion. 

As I continued to enter the world as a transgender woman, many times, the world pushed back at me. I had problems with how I moved and how I communicated with the public before I could ultimately relax and really learn to dance. As I tried and tried to improve myself, most of the push back came from my second wife and my old male self. Both of whom had stakes in my success or failure in my new world. I have written often of the times when my wife rightfully said I made a terrible woman. Mainly because I was still putting my woman together and was making mistakes. At that point, I did not have the lived experiences as a trans woman to do better and anytime she caught me out of our agreement to explore the world, all hell would break lose. Afterall, she understood more than I did how she was losing my male self to another woman. Who happened to be me.

Once I broke through and decided transgender womanhood was the only dance for me, I began to do better. Physically, I never made it to being a better dancer, but mentally I did. Primarily because I needed to survive in the feminine world or sandbox, I chose. By nature, I found cisgender women operate on a whole different level than men. Which I already knew of course but not to the point of survival I found myself in the midst of. To oversimplify, men came at me from at the most two angles, and women from many more. I was ambushed by several passive aggressive women on many occasions before I learned to protect myself from perceived lesser threats. 

To this day, I am still dancing. Primarily because it is what it takes to be a transgender woman in todays' world. Plus, I would be remiss if I did not mention the small group of women friends, I had who were instrumental in helping me with my dancing lessons.   

Can't Go Back

 

Image from UnSplash.

At the ripe old age of seventy-five, there is no way I will back track my long difficult gender journey to transgender womanhood. 

One thing I never thought would happen is I would ever have to consider backtracking at all but here I am. Of course, the main reason I am doing it is because of the orange felon attempting to destroy our country as we know it. In the short span of time, he has been in "power", already he has affected me severely. Or almost has. 

The first time was when the Veterans' Administration came down with a new directive saying there would be no more gender affirming hormones provided by the VA. Since I receive my HRT from VA Health, I was rapidly attempting to discover a Plan "B" to get my hormones. Then the VA amended their hormone directive to not issuing HRT to new veterans only which of course left me out. I felt good for me and bad for any other new veterans suffering with gender issues along with other problems. 

Then, there was a glimmer of hope from the powers to be who were looking for a loophole in the gender directive. The loophole was veterans needing HRT for mental health reasons could still be administered hormones, just not wigs or various items such as breast forms. So, for the time being, the status quo has been maintained. No thanks to the buffoon in Washington.

The second major issue manufactured by the gender bigots in Washington is the "Save Act" which is designed to take voting rights away from women everywhere. Transgender or cisgender. Here is a segment of explanation of what the "Save Act" means: 

"In addition to married women,” Cherry said, “any eligible voter who has changed their names for myriad other reasons (related to marriage or divorce, a gender identity transition, a change based on personal preference, etc.) could face heightened barriers to vote if the SAVE Act were enacted due to their lack of birth certificate that reflects their current legal name.” Cherry is a legal director for "Voteriders" which provides voter ID information.

My problem with the bill is my birth certificate has never been changed here in Ohio to reflect my new legal name, and counties here in Ohio are refusing to do it. Including the one I was born in. So, I could not use my birth certificate to vote. The act still has to pass the US Senate, so we will see what happens. Whatever does happen is I never want to lose my precious right to vote as my authentic self. 

One thing is for sure; I will never backtrack from my life as a transgender woman. As I write about often, I can never relive all the exciting years I spent as a novice in a fulfilling new world. Also, I need to add how much I resent the recent attacks into my world. Like the rest of you, I am just living a quiet life and don't need you to tell me which restroom to use or how to vote. 

Mainly now because I do not ever want, nor will I go back, and I will never disappear. If by chance, the blog goes away because of my comments, you will know why. I hit the big time and was noticed by the wrong people.

Authenticity

Transgender flag flying at 
Cincinnati's City Hall.

 In order to just get by in the world, transgender women, or trans men need to be authentic. Which is always easier said than done. 

First of all, you need the confidence to try out your new self in an exciting yet scary different world. Maybe, a person smarter than me has an idea on how to provide yourself with confidence other just by just doing it. For transgender women, among other things, it means putting aside all the hard-earned male privileges we came to be used to. In order to be truly authentic in our transgender womanhood, everything male had to go. 

It took me years, or even decades to get around to living authentically as a trans woman. Before I was able to, I needed to adjust my thinking to what a woman really was, and what she had to go through during her life. As my second wife kept trying to tell me, there was so much more to womanhood than just looking like one. Finally, I started to realize what she meant, but it was not until I made it out into the world as a novice transgender woman, did I realize what she really meant. For me, it meant the girls nights out I was invited to, along with everyday communication helped me to discover my true feminine self. 

Even still, all those nights I went out to be by myself were not helping me with my authenticity. I learned the difficult way all females were not women because they were never socialized into womanhood. Through it all, I wondered where the whole process would land me. For years, I feared a hard fall in my life if I had fully transitioned into transgender womanhood, but it never happened for me. I think, the more I learned in my new life helped strangers to interact with me easier, one on one. 

Perhaps the biggest discovery in my life came when I learned firsthand how powerful my internal feminine self was. Once she sensed she had control in my life, she effortlessly took over and guided me to a soft landing when I slid off my gender cliff. One of the main things she did was making me how total the femininization process was once it got started. I guess the first thing she changed was how I looked at my life. For example, she made me realize I was never a man cross dressing as a woman, I was a woman cross dressing as a man. All of a sudden, my early life made sense as to why I could never satisfy the deep craving I had to dress as a woman, only to discover a couple days later, I would be depressed if I could not dress again and find the nearest mirror. I needed constant reassurance I was on the proper path to my own form of transgender womanhood.

I guess, authenticity can only be earned the hard way through lots of work and even experimentation.  When you do experiment, and are successful, gender euphoria and confidence set in and you are ready to move forward in your life.   

Transgender Day of Visibility

 

Transgender Day of Visibility
poster from my
hometown. 

Today is the annual transgender day of visibility on March 31st. 

It is a time such as never before to attempt to stand up and be counted as a transgender woman or transgender man. Sadly, it is also the time we trans people take the most risks to do so. Stakes are becoming higher and higher against us coming out in many areas of the country, especially, here in my native Ohio. Where an overwhelmingly republican legislature in the state capital of Columbus has passed bill after negative bill against us. 

To me, my visibility is an ongoing deal. Since I live fulltime in my transgender womanhood, long ago I decided to never run and hide my feminine nature. Back when I did not have so many mobility issues, I was more of an active participant than I am today. In place of being active at all, I have tried to pick up my pace with my writing and protest with my keyboard and votes. 

Plus, I know I am so fortunate to have found and married an accepting/encouraging spouse who helped usher me into my transgender womanhood. I know so many others in the community who are so lonely. 

Wherever you happen to be in your gender transition, these troubled days present a troubled challenge to being visible. Challenges such as your presentation provide sometimes insurmountable hurdles to being more visible. Similar to a "Catch 22" of passing. In other words, you need to be seen in public to learn if you present well enough to stay out of personal danger, but it is scary to even start to get the experience to begin with.  Again, I was lucky when my time to come out meant at the worst you were laughed at and not beat up. Plus, I was able to put years of practice into makeup, fashion, and wigs when I cross dressed in my closet. If the times were reversed, I often wonder what I would have done differently, if anything. All in all, it is just another one of those life's questions I will never know.

On this transgender day of visibility, I hope all of you find your own way to be visible. Anything from marching in a parade, all the way to looking at yourself in the mirror, find a way to celebrate the rare, beautiful self which is you! 

Seasons Change

 

Image from Jamiethlene Reskspe on
UnSplash.

It appears that Spring has quit teasing us here in Southern Ohio and is finally here to stay. Spring teases us every year, so it is no real surprise when it happens. We can go from summer like weather to winter in one week. 

What it means is wardrobe adjustments which account for cooler mornings and warmer afternoons have to be made.  Plus, I always use the unique seasonal changes here to completely go through my clothes to see what will stay and what will go.  From nearly the very beginning of my love of everything feminine, I had admired how girls and women had the opportunity to completely change their fashion with the seasons. Putting aside all the challenges I had with having any resources at all to buy new fashion, I still did my best to meet the seasonal change challenges. 

My biggest challenge this year is coming up in the middle of April when my wife Liz and I have been invited to my daughters in laws house for a lunch get together. I am planning for it already and am planning to wear a two-piece lightweight top I just purchased for our trip to the Florida Keys. I will pair the top with leggings I have and hopefully will be dressed well enough to blend in with the rest of the women who will be there. Sadly, I don't think my transgender grandchild will be there because they (pronoun of choice) will be hiking the Appalachian trail with their partner. I will have to find out from their mom if they still are going to have a job as a civilian nuclear engineer with the US Navy or did the orange felon's threat against transgender women and trans men destroy any hopes of having a job. 

In the meantime, it is opening day in Cincinnati for the pro-baseball Reds, which has a huge parade and is close to a complete local holiday. Since the parade is televised during the afternoon, and I really don't care much for parades, it will give me a chance to get started with my spring wardrobe assessment. I know right now, I am setting fairly well with my collection of light weight tops and T's. Especially when I added a few select T Shirts from my trip to Key West, Florida. I purchased a very colorful T(shirt) from "Harpoon Harry's" where we ate lunch and later made a special stop in Jimmy Buffet's "Margaritaville" shop where I picked up another shirt to add to my collection. My second wife and I were huge fans of Jimmy and when he passed way, another of my bucket list items went with him.

Watching Buffet's famous Cincinnati summer riverside concerts were always a hit with us, but little did my wife know how badly I wanted to be one of the women watching the show. My transition took so long, I sadly never made it. 

Now, I hear the birds chirping and a pile of clothes awaits to be sorted to be worn or donated. It has always been a labor of fashion love for me to go through the seasonal changes which made being a woman much more fun for me than being a boring man. Even though, sometimes I think the fashion experience is shallow in nature, it has always been fun to me. 

Especially, when I can shed the boring dark colors of winter and become a part of the new bright spring flowers and budding of the trees. Everything I wanted to do when I started my path to transgender womanhood. It also time to put all my sweaters away and turn another page towards my future and bright as a new season.

 

The Light in the Mirror

 

Image from Alessandro 
Bianchi 
on UnSplash.

I spend quite a bit of time here attacking my mirror when I was growing up.

Recently, I have come to the conclusion some of my negativity could have been wrong. First of all, I was fortunate to have a beautiful full length mirror dad installed at one of the ends of the hallway in our house when I was growing up. When no one else was home, I would spend as much time as I had admiring myself in the hallway mirror. As I did, I could always see a brief dim light in the mirror when I viewed my feminine self for the first time. Even when I knew, the light would have to be extinguished soon, and I would have to go back to my unwanted male world. 

As I grew up and began to explore the world for the first time as a beginning cross dresser, I made plenty of mistakes the mirror did not tell me about. In fact, the mirror light shone brightly and told me I looked great when in fact, I looked just the opposite. I was presenting as a clown in drag with no one to warn me. For a long time, the light in the mirror nearly went completely out as I was rejected in public time and time again resulting in a deep depression for me.

I kept trying though, and the light began to come back on. I lost weight and began to find styles of women's fashion which flattered my body shape and finally began to present better. Especially when I was making the mental transition to novice transgender womanhood from cross dresser. To do it, I needed every break I could muster. Plus, I needed to turn up my light in the mirror, and let my femininized light shine through, so I could see her better. 

The extra light turned out to be all I needed to become more skilled at my makeup art and do the best I could with my testosterone damaged male face. With a little help from a professional makeup person, my light in the mirror grew even brighter, and more importantly, I could trust it. With trust came confidence which equated to more acceptance as a transgender woman in the public's eye. All of a sudden, my lifelong dream to lead a feminine life was within reach. If my light in the mirror stayed on. 

It did and I was even able to turn up my light to a brighter level with the addition of HRT or gender affirming hormones. Among the many other positive changes I went through was when the overall texture of my skin softened. Which meant the male lines in my face softened and I could use less makeup. Specifically, foundation. I quickly learned with more femininized skin and being able to wear my own hair, I was suddenly more presentable to the world. 

Looking back, I may have been too quick to judge my light in the mirror. It just took a little longer (along with the rest of me) to become more situated with living a new life away from my old male self, and perhaps it was my fault for not switching to a brighter bulb sooner. Plus, I was fortunate in that my light in the mirror did not burn out altogether. 

 

Knowing the Rules before You Break Them

 

Image from Milan de Clercq 
on UnSplash

I had a very good idea of what it would take me to survive in a male world before I decided to see if the grass on the other side of the gender border would be any better or greener.

Growing up in a very male dominated family with the only girl being my mom, provided me with a so-called brightly lit path to my future. I was fortunate in some ways to have a larger male body to keep the bullies away as I played sports such as football and baseball regularly.  Of course, I came to dislike my body completely when I went through male puberty and had a difficult time finding any new fashionable girls' clothes to wear. 

When I went through the hated male puberty, the rules of the road so to speak, became clearer and clearer to me. Coming from a white middle-class family with two working parents in the 1950's to mid 1960's gave me a work ethic I used to scrape together the meager funds I needed to buy my own makeup and a few fashion accessories. I knew I could not ask my parents for the money because they would want to know what I needed it for. Any hint of femininity on my part would immediately break all the rules and would result in trips to a psychiatrist. Even then, I knew going to a therapist who knew nothing about gender issues would be a disaster. 

I knew the rules and played the game of male gender the best I could. I found good hiding places for my femininizing fashion and makeup while at the same time, dreamed of the day I could buy a nice wig. In those days, I was able to get by with a mirror who never lied to me by telling me I was a pretty girl. The feelings of joy or gender euphoria would continue several days before the pressure built up on me to cross dress again and again. When I began to realize I was just scratching the surface of my gender issues, I became quite good at knowing one of the primary male rules taught to me as a kid. If you did not like something, internalize it until it went away.

The problem I had was, my desire to be a woman never went away and it was so much more than just being a phase. From the darkness of my closet, I had what turned out to be a distorted idea of what womanhood meant to females everywhere. I only saw what I considered the good part was. Such as no military service and being able to enjoy the wonderful world of woman's fashion. I left out the challengingly part of women's lives such as child raising and toxic men, to name a few. As I was able to cross the gender border, I did realize the grass was not always greener and had I truly been a birth daughter to my mom, extra pressure to conform to her standards would have increased. I am certain she would have pushed me to go to the same university she did, all the way to pledging the same sorority.  I would have again been breaking rules. Just of a different sort.

When I arrived at a time when I was drafted into the military, I was forced into being a follower of rules more than I ever had in the past. Conforming to new Army standards to survive at least kept most of my mind off of my gender issues. I needed to put my desires aside and just dream of the day I could be free to be a transgender woman in my future. It was difficult, but I did it.

By the time I was honorably discharged three years later from the Army, I was able to settle back into the life I had before without one big exception. Without military service looming over my head, I could concentrate on my future. When I did, it became increasingly evident to me, there was a possibility I could break all the gender rules and achieve transgender womanhood. It was still going to be a decades long journey from there, but I was encouraged for once.

Of course, once I began to explore the world as a novice transgender woman, I found a whole new set of rules to deal with. To make matters worse, I had no knowledge of many of the rules I was about to break before I did them. The workbook I was using was blank and I needed to write the rules as I needed them. 

Again, I was fortunate, and I survived when I broke the rules, but I learned quickly since I was free.  Then as I safely continued along my gender path, I found I could make it safely to my dream. Mainly because I knew the rules from both sides of the binary gender and I was a better person for it. 

Why Not Me?

 

JJ Hart at Club Diversity
Columbus, Ohio

When I was very young, I had the tendency to hide behind my skirts when I needed to deny any masculine pursuits at all. 

Any time I failed, I ran home to see if I could lock myself in the bathroom and apply makeup and try on any of mom's clothes which still fit. I had a dream of finally making it to my own transgender womanhood when I grew older, but I had no idea of how. Back then, little did I know, the journey would take me over fifty years to complete and the path would be so curvy and full of hurdles. If I did, I wonder if I would have ever attempted to try it.

Of course, I started out innocently enough as a cross dresser in a mirror. My reaction was a double-edged sword. One side of the sword told me I was not doing anything really wrong, while the other side wondered if I was the only one in the world doing it. If that was the case, being a transvestite just could not be good. Right? All I had to rely on was my instincts which told me I was on the right path. So, I persisted and stayed on it. Since the only real feedback I had was from the mirror, I needed to rely on it when it was telling me I had advanced on from the clownish drag makeup stage I was into a more acceptable feminine form. At the time, I equated it with painting model cars which I was never good at and I was so proud when I thought I had conquered the basics of makeup. Even to the point of purchasing my own from the newspaper route I had when I was a kid. When my friends were buying model cars, I was buying makeup and loving it. It was not until many years later, would I receive the instruction I needed to really understand the art of makeup, but I was getting by at the time.

Clothes and hair were a whole other problem I needed to try to conquer at the time. With the very limited budget I was on, there was no way I could afford a nice wig all the way to my college years, when I was working a better paying job. In order to buy a wig, I needed the help of my fiancé who bought it under the idea she would possibly wear it. The wig was long and blond and was my cross-dresser's dream and luckily, she hated it, so I inherited it. Even with the abuse I put it through, the wig lasted for years before I needed to finally retire it. Clothes were another problem because again I did not have much money, and these were the days before larger sized women's fashions became available in a younger style. It was not until years later, when thrift stores became abundant, did I finally become fashion independent. 

As my feminine life was coming together, slowly I began to realize transgender womanhood may not be such a reach for me after all. I was beginning to explore all facets of the world as a trans woman and it all felt so natural. The more I attempted and succeeded at in my new life, the less I wanted to go back to my old, boring male world. So, I did not.

I was on a slippery gender slope my path had led me to, and all of a sudden, I did not fear it anymore. Somehow, I knew there was a soft landing out there for me. The stop signs were gone, and I knew at the age of sixty, if I did not try to live my transgender dreams, I would never have the chance and would forever regret my decision. From there, I decided to follow my heart and seek medical help to begin gender affirming hormones or HRT. The hormones forever sealed my trans life, and I never looked back. I always felt my body was looking for the hormones the whole time. Again, a scary gender transitional moment felt so natural. 

Why not me, turned out to be why should not it be me? 

Gender Masks

 

Image from John Noonan
on UnSplash. 

In life, both genders learn early on what masks mean to their existence.

Think of it, at the earliest age, babies have only very limited ways to show their pleasure or anger by smiling or crying. Of course, as we advance through life all of it changes. I could be biased, but I think women in life have an advantage by using masks. 

While boys are squaring off on the playgrounds at school, girls are learning the basics of makeup, if their moms allow it. In many ways, makeup for women provides them with their ultimate masks. Anything from false eyelashes to skin foundations to wigs are permissible. It is not unheard of for a man to wake up to a totally different looking woman after a night out on the town. 

Makeup is not the only way women use masks effectively. I learned it the hard way several times when I was first out in the world as a transgender woman that a smiling face does not necessarily equal acceptance in the world. There were many times I relaxed too early in a situation with another smiling woman and ended up getting stabbed in the back. I fell for her friendly mask and paid the price. The whole process with women with me went back to feminine passive aggression versus the old direct aggression I was used to with men. Eventually, I came to consider the process as just another rite of passage into the world of women and I quickly became much better in being able to see what was going on behind another woman's mask. 

As my relationship with other women grew, the better I became at perfecting my own mask. I started at an early age attempting to perfect my art of makeup. It was all I could do to stop looking like a clown in drag. I stumbled along at my mask efforts before I made it into asking for and accepting professional makeup help. I happened into it during a cross dresser, transvestite mixer I was attending. Part of the mixer was given over to several professional makeup artists who offered free makeovers to anyone who wanted them. I gathered my courage, hitched up my big girl panties and stepped up for help. When the help I received was complete, I could not believe the change. The guy doing my mask had totally removed my old mask and designed a new one. The changes were so dramatic, I even received an invitation to go with the so called "A" list transgender women when they went out to bars after the mixer. To make matters even more dramatic, I was the only one approached by a man in a bar to stay for a drink. For many reasons, I did not stay and drink with him, (another story) but the point was made my mask could compete for a change with the "A" girls who the man ignored. 

The best part of finding my new mask was being able to keep it. The professional makeup guy managed to explain everything he was doing to my face and wig, so I understood it and could replicate it over and over. Once I had my mask, I was able to take advantage of it the same as any other woman would. In fact, more so, because I felt to succeed in the world as a transgender woman, I would need to be better than the average cisgender woman who had been born with a built-in mask advantage. 

Fortunately, I was able to step back and look at my new gender mask from a positive perspective and what it meant from view of a novice transgender woman. When I did, my life radically improved for the better and I understood how masks really worked in the world.

Back Up Plans

 

JJ Hart visiting Key Largo.

Following several near misses as a novice transgender woman out into the world, I began to smarten up and have back up plans when I was in perceived danger. 

After the near misses with security problems on dark streets where I should have never been alone, I hurriedly went home and looked to see if there was anything in my cross dressers handbook which would have alerted me to possible issues. Since I had a beginner's handbook, I found no such warning and because I had been raised male, I went on my way like nothing should ever happen. Well, it did, and I was fortunate to buy my way out of the problem with my last five-dollar bill. From then on, I learned my lesson and never went back there without an escort of some sort. Common sense had set in. 

Many other of my problems early in my public life as a cross dresser or transgender woman came from other less than intelligent decisions, I made on my own which set me up for failure. Such as the night when my second wife and I attended a diverse mixer in Columbus, Ohio. Against her wishes, I wore a very short mini dress with my long blond wig and ended up being trapped and nearly accosted by a much larger and aggressive "admirer" in a narrow hallway of the house we were in. My wife showed up and he backed off, giving her an ideal "I told you so" moment. From that experience I learned how helpless a woman could feel when trapped by an aggressive man. I went home and added it to my back up plans for the future and scribbled it into my mental gender notebook.

Other experiences were less stressful and even more humorous. One I will never forget was when I was tempting fate with wearing water balloons as breast forms. The double-edged sword of wearing the water filled forms was they were very fragile. Especially when I ignored the danger and made the balloons bigger. All went well, until the night one broke while I was out drinking in a venue, I was a regular in. I was lucky, when the mini flood cut loose, I was already heading for the women's room which happened to be deserted.  I was able to clean up, pay my tab and leave without further incident. I did not think telling the staff I was pregnant would have worked. When I arrived home, the water balloon breast forms became history for me, and I saved up for my first set of silicone forms. 

As the years flew by and I became more interactive with the public, I began to fill out more and more of my transgender workbook, complete with backup plans. I learned to be more cautious with my plans, allowing for more of the inevitable problems which would crop up. Even still, I was caught unaware on several occasions. One of which comes to mind when I was innocently chatting with another woman's husband when she went to the restroom. When she returned, in no uncertain terms, she made it clear I was not supposed to talk to him. My back up plan was to quickly leave, and I did.

I learned also, as I transitioned away from the male gender, very quickly I lost all my male privilege too. The old bluster my way through potentially dangerous situations went away. All of a sudden, I needed to look ahead and not put myself into those situations to start with became important. Many times, I needed to think if things could go wrong, they would. Before it was the same for my spousal relationship, I needed to begin coming home earlier so I could take off my makeup and clothes before my wife returned home from her night shift. Most of the time, I did make it, but when I did not, there was hell to pay. 

Finally, when I became freed up to live my transgender womanhood, I could store away most of my back up plans and move on. However, many of the plans I discovered were just part of being a woman anyhow, so I considered them a rite of passage. Other women grew up learning about the gender rules (right or wrong) and I needed to do the same. 

From Obsession to Passion

 

Image from Kayshawn Herandez
on UnSplash. 

For years I considered my desire to cross dress was more an obsession than anything else.

Similar to many of you, I started my path to femininization innocently enough by rummaging through my mom's clothes. Whatever I could fit into was fair game for me. The pleasure of the overall experience soon turned into an obsession. When I returned home from school and was alone, I locked myself into the bathroom and got busy with mom's clothes and makeup. 

Even though I was wrapped up in my obsession at such a young age, doubts snuck through and slowly became evident. The biggest doubt was I was more than just a cross dresser. I wanted to be so much more. Such as the totality of being a girl. Looking back, it was sad I did not have more information on gender issues because I would have discovered and hopefully faced up to the fact, I was more transgender than cross dresser. 

As I trudged forward through life, I stubbornly held on to the best I could to my largely unwanted male ways as I idolized the girls around me. Thinking they had all the assets in life. Primarily the one in which they did not have to be forced to serve in the military during the Vietnam War as I did. Why did girls not have to serve, and I did, made me quite bitter. However, there was nothing I could do about it, so off to serving three years in the Army I went. 

As soon as I was honorably discharged from the military, I began to restart my cross-dressing obsession in earnest. Off came my Army mustache and on came the blond wig. Since my first wife knew I cross dressed and did not really care, I was able to do more exploration into the world of fashion, wigs and makeup. In essence, I was making up for all the lost time (three years) I had in the Army when I could not cross dress. The lone exception was a Halloween party when I dressed as a prostitute. The one night of bliss hardly made up for the three years of staying away from my obsession to at the least appear as a woman. 

When I finally had the courage to try out the world as my increasingly evident feminine self, my focus began to change from obsession to passion. I spent every spare moment daydreaming of how it would be to try out what I was doing as a man to a woman. During this time, gender reality shifts turned out to be a major point of my life. Especially when I actually began to live out my gender dreams.

What I did then was set up mini gender "bucket lists" to attempt to conquer. I say attempt because several were ill-advised and nearly impossible to accomplish. One in particular led me down a dangerous safety path when my male security privilege was lost. I almost learned the hard way not to be on dark city streets out of my car unescorted. Even though, I was still stubborn about my passion, I learned I needed to be careful. When I went back to the area where I was approached at night, I made sure I asked one of my transgender man friends to escort me. It was a new experience to ask for help. 

My passion to be a full-time transgender woman took me through gender affirming hormones and changes I never thought possible. I was grateful I was medically cleared to take the meds by a doctor at the advanced age of sixty.   

I am also grateful to be living my passion now with a wife who loves me very much. I took over a half a century to get there but I switched a basic obsession to a fulltime passion, and I never looked back. 

Why Not Me?

 

Image from Danielle
la Rosa Messina on
UnSplash

Going through life, I was very insecure concerning many things.

I always had a difficult time excelling at all in things such as sports because I was so insecure about winning. If I did not, which was common, I could run home and hide behind my makeup and pretty dresses and pretend I was a girl and all the pain of losing went away. Then, the more I cross dressed, the insecurities began to sneak in there also. Was I presenting well enough and how would I ever know if my only contact was between me and my mirror. I thought I looked presentable, but would the world agree and what if I looked like a clown in drag.

It took me years to even acquire the basic wardrobe and fashion I needed to even get myself a fair shake with my feminized presentation. All along, my lifetime dream was to be a woman, and I was so far away. I did try to make an excuse to cross dress and come out to a friend once, but it was a dismal failure when he was embarrassed and turned away. The whole experience sent me running back to my gender closet and slamming the door. I did not know what my next move would be.

Life went on for me and the desire to possibly living my feminine dream never went away. In fact, it became stronger and stronger. When I could, I made "investments" in better fashion, wigs and makeup which really helped me advance my overall presentation. As I did, I gave the public another try to see how I faired in the world out of my closet. I needed to put aside all my insecurities, gather up all my courage and give it a go. 

Initially, my path was a bumpy one, full of false stops and starts. I was flying blind with no handbook to help me, and it showed. During too many nights in failure, I had to run home in tears wondering if I was on the right path at all. Somehow, the faint voice of my inner feminine soul could be heard telling me not to give up as there were better times ahead. I listened, pulled up my big girl panties and managed to move forward as I discovered a better life as a novice transgender woman. 

I discovered the best way to combat my insecurities was with confidence. I resolved to never let the world see me sweat. First, it would ruin my makeup and second, if someone had a problem with me, it was their problem, not mine. I had put an incredible amount of time and effort into being the new transgender woman I was becoming, and I would be dammed if I was going to give it up easily to some bigoted transphobe. All the years of losing weight, learning makeup and skin care just could not go to waste as I chased my insecurities about living fulltime as a transgender woman. 

Still, I wondered, would I ever be good enough to join the world of women and would it be what I expected it to be. 

Unexpectedly, I received a giant push from women friends I found and cherished. With their help, I was able to put my insecurities behind me and become a part of a world I had only dreamed of. Why not me, became you can do it and I succeeded in my path into transgender womanhood. 

Trans Girl Shopping

 

Image from Sam Headland on UnSplash.

Many Christmases ago, in the early two thousand's I began to do most of my special gift shopping for my second wife as a transgender woman. Needless to say, I learned a lot. 

My wife was a huge gardener, so greenhouses and specialty garden stores were my first places to go to if I was to ever find the special gift, I was looking for. To find the best selections, I normally made the hour trip to Columbus, Ohio which had bigger greenhouses and even a specialty garden store in one of their upscale malls. Since at that time, I had a reasonable amount of spendable income, almost nothing was out of reach for me as a gift for her. 

Normally, I made the trip during the day and wore professional women's business attire. My hope was I could present well as a woman just on her lunch break shopping for last minute gifts. Even though, I was beginning to feel more and more at home as a woman in the world. Still, I felt I needed to work hard to be able to present the best I could as a transgender woman to avoid detection. Seeing as how I was knocking out two birds with one stone, I needed to do it well. 

I should not have worried because one way or another I was treated warmly by more than a few of the clerks I faced and at the worse with indifference by others. I found the older clerks were more apt to help me and the younger ones left me on my own to shop. Even being left alone was alright with me because I was so intensely trying to find just the right gift for my wife who did not know it was my feminine self-doing almost all her shopping. Along the way, I found all sorts of unique gifts from new garden tools all the way to vintage seed boxes in antique malls. Which is a different story for another blog post which I will write before Christmas. 

Perhaps you are wondering what I wore for these new yet scary shopping adventures I was on. Depending upon which mall I was going to, I attempted to scale up or back on my outfit so I would not appear out of place. At that time, Columbus featured two very upscale malls, and I could not miss out blending in by dressing in my finest silky black pant suit, blond wig, and heels along with my very best application of makeup. All my efforts worked well as nearly everyone ignored me, except a few men. 

Since I was being successful in my transgender womanhood, and I was able to be out in the public's eye for an extended period of time, I decided to push my boundaries and stop to eat and use the lady's room. Both were a challenge for me since I had rarely done it before. I gathered my courage and stepped into one of the sit-down restaurants in the mall and just took a seat at the bar to eat. Sure, I was scared of having any one-on-one communication with the public but on the other hand, I was so successful so far in the day, why not push my luck. 

It turned out all my fears were unfounded as I was treated well in the venue I chose and the only problem I had in the restroom was navigating my way around using the toilet in my pantsuit. I did not think far enough ahead when I chose my outfit for the day and put fashion ahead of rest room utility. Fortunately, I was able to complete my struggles successfully, take care of business and leave the lady's room before anyone else came in. 

I finished the day of trans girl shopping as a very successful experience with the added positives of finding great gifts for my wife. I could not wait to do it again.

Tennis Anyone?

Image from Tony Luginsland
on UnSplash.

 Back when I managed a prominent casual dining/bar venue, we had two women who would frequently come to our bar after finishing their round of tennis. 

Of course, I always noticed and was jealous of their short tennis outfits. I immediately put acquiring some sort of a tennis outfit on my cross dressing to do list. Since I had always admired short mini skirts and dresses on women, finding a short mini white dress to wear as the primary part of a tennis outfit was a priority.

As luck would have it, I found the ideal dress at a women's clothing shop in a mall I always went to. Once I had the white dress, I discovered the rest of the outfit would be fairly easy to put together. I ended up finding an inexpensive pair of white tennis shoes and socks to go with the shoes. The only problem I had then was what I was going to do about the hair on my legs. 

Even though my wife knew I shaved my legs on occasion, she was not overjoyed when I shaved. Primarily because she worried, I was up to no good when I shaved my legs, and she was right. On this occasion, I could not wait to show off my legs and new tennis outfit in one of the malls I always went to. Before I went to the mall, as always, I needed to create the time to do it away from my wife's disapproving eyes. I waited until she was working a day shift, and I began the fairly intense process of shaving my face and legs. 

Once I completed the shave and applied my makeup and hair, I was ready to test out my new tennis look outfit on the world. Immediately, I felt the thrill of my shaved legs in the short white dress I was wearing. So out the door I went into the world. As I arrived in the mall, I noticed my supposedly admiring public was primarily made up of retired men in the mall just to walk and admire the view. Since I was the view, I wore a pair of sunglasses so I could watch their reaction to me without being obvious. It worked and I could see them staring at the tall blond in a tennis outfit.

As I saw it, I received all the pleasure from tennis without putting in all the work. Now all I needed to figure out was how to hide my extra women's clothing. On this occasion, I used a little used closet and hid my new treasured outfit among a set of my old male clothes I never wore. 

For a change, my ideas of how to come as close as I could to learning for myself how a woman would feel in a tennis outfit came together. I could show off my legs and have fun doing it. Plus, I could cross another item off my transgender bucket list. Quickly, I was off to another quest. 

The Double Edged Gender Sword

Image from JJ Hart. Wife Liz on left.

The longer we live as transgender women and trans men, often we find many aspects which represent a double edged sword. 

One of the edges of the sword has to be the duress we feel when at first we arrive in public for the first time. To make matters worse, we have no peer group to help us out of the mirror to be judged by the harsh eyes of the world. No one to tell us we looked clownish as we tried the makeup arts for the first time. I can't tell you how many times I hurried home in tears following being stared at at the least, or laughed out of a venue at the worst.

From it all, I learned to develop a thick skin and always go back to the drawing board as quickly as I could to help solve any presentation problems I might have had. Even when I was doing it, the cross dresser drawing board was certainly difficult to figure out. What happened was, I used the very brief moments of gender euphoria I earned and moved forward attempting to tightrope my way along the sharp edge of my sword. I was risking ridicule at the least and the loss of family, friends and employment at the worst. Failure as a transgender woman was a very real pressure.

Once I began to learn how to present in public more effectively as a transgender woman, I began to use my sword more effectively.  Then the world became much more comfortable for me in my quest to live my femininized dreams. In addition, my makeup arts became better as well as my use of hair to enhance my appearance. 

It bares mentioning also, going through the overall transgender experience, made me a more resilient person and set up to battle the more challenging times we face. I learned in my research transgender folk have always been around and always will be, no matter who tries to erase us. Battling the sword all these years helped me be more secure in my transgender identity. 

In all fairness to my sword, it started out very dull. I worked long and hard to sharpen it by going out in public which was the best indicator of my progress.  So I took all the good and bad and did the best I could with it. All my interaction with the public included the dark evenings when red-necks repeatedly kept playing "Dude Looks Like a Lady" on the juke box in a venue where I was a regular. Since management at the time would not support me, I left to find another venue and took my money elsewhere. I was rewarded months later when an employee from the venue I was discouraged from coming to, found me in another venue and invited me back. To make matters even better, the manager who would not back me up was fired for drug use. Excluding a stray bigoted woman in the woman's room, I never had any further problems there again.

Once my gender sword swung back into doses of gender euphoria, I began to appreciate all it had done for me. Transgender womanhood was finally mine to enjoy when I learned I was not a quitter and was in my transition for the long haul. 

Trans Girl at Black Friday

Woman Shopping on UnSplash.

As I advanced on my feminine path to transgender womanhood, at certain points I needed to do more and more traditional feminine activities which cemented my claim to be a trans woman.

One of those was joining all the women in the world who were out and about shopping for the bargains bright and early on "Black Friday" or the day after Thanksgiving. My second wife for years was part of the crowd and made sure she was one of the early shoppers. 

Of course, I always wondered what the attraction was to go out and battle all the crowds, except for saving a little bit of money. Finally,  many years of wanting to shop with my wife as another woman came to an end but suddenly, on the other hand, I had the chance to shop on "Black Friday" as a woman by myself. Along the way, my second wife became the assistant manager of a large bookstore and of course "Black Friday" was one of their biggest days. So, I knew in advance she would have to work and I arranged my schedule so I did not. 

On the morning of shopping, I was excited as I prepared myself for a morning I had only ever dreamed of. First I did all the shaving preparation, including face and legs. I needed to calm down before I dressed in my favorite bulky sweater along with my best denim skirt and comfortable flat walking shoes. Then I began the more crucial part of applying my makeup and wig after I had calmed down...somewhat. After I reached what I considered to be a good presentation which would blend in with all the other women shoppers I would encounter, I gathered my courage to leave the house and head to a nearby upscale mall which I was very familiar with.

Unbelievably, in a very crowded parking lot, I found a space close to one of the entrances. As I checked my makeup and hair for the final time, I thought back to all the times I wondered what it would be like to shop with the other women on "Black Friday" and here I was and into the mall I went. My initial reaction was one of calm because no one was watching me, they were on a mission to find the best bargains and complete their shopping lists to bother about a transgender woman in the crowd. 

Since I wasn't really there to shop anyhow, I just browsed a few stores and bought a few small gifts for my wife before my shopping came to an end. After all, I had accomplished my goal of experiencing "Black Friday" shopping up close and personal as my authentic self. It was another item I could check off of my transgender woman bucket list.

Time flew by and  I needed to be back home to change back into my old boring male clothes to go to work, I needed to bring my dream day to an end earlier than I liked. 

Possibly the biggest lesson I re-learned that exciting day was the power of blending in with the rest of the women around me. As long as I could accomplish looking similar to everyone else, I could present well enough to get by. My first Trans Girl at the "Black Friday" shopping experience was certainly worth it.

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. 

Reaching Out for Truth

 

Image from Jen Theodore
on UnSplash.

As I transitioned into my form of transgender womanhood, first I needed to find my own truth. In order to do it, I was placed in a dilemma. 

The dilemma was I needed to make sure my gender journey was taking me in the right direction. I needed to make a huge life changing decision so I needed time and experience to make certain I was taking my life in the right direction since essentially I was risking everything to do it. In other words I needed confidence. 

Gaining confidence proved to be a fragile thing to find. I would have it following a successful day out away from the mirror as a novice transgender woman when I seemed to do everything right. My makeup, wardrobe and wig were on point and I even carried myself fairly well. I was building the life I always had dreamed of and seemed to be within reach until the next time I went out and everything crashed and burned. Either I did something very unrealistic and was laughed at or my overall appearance just wasn't right. Whatever the problem was, my fragile confidence was shattered. And, as we all know, confidence is our most powerful accessory. Humans are similar to sharks, if they perceive something is wrong with you, chances are the other human could act on it. A big turning point for me was when I arrived at the point where I did not care what anyone else thought of me. 

Actually, let me re-phrase that. I did not care what men thought of me because for the most part they had all felt as if I was from another planet anyway and wanted nothing to do with me. On the other hand, I did care what other women thought about me. Since I needed other women's acceptance to exist in the same world they were in, I needed their approval. In order to survive, I needed to be honest to myself which in turn, made me honest to them. I was not hiding anything. I was upfront on what I was trying to achieve which was to give up my old life as a man. Very quickly I learned I appealed to more women as a friend than I ever had as a man. I thoroughly enjoyed my learning curve as a transgender woman and wanted to build on my truth even more.

Even still, on occasion, I was still having issues with living my truth. My biggest hurdle to conquer was myself. I was the last to know my truth because I hid it all so well. To my everlasting shame, I even lied excessively to my second wife about what I was really doing while she was working at night. So, by osmosis, I was lying to the two closest people to me. Something I am certainly not proud of. However, I am proud of the fact I did reach out and grasped my truth during my long life. 

It took me long enough to do it. I struggled for over fifty years as a cross dresser and went through so many stages of attempting to figure out who I really was. I was so much more than a man who liked to wear women's clothes, I wanted to be a transwoman wearing women's clothes. Once I learned this major truth about my life, finally everything came into focus.