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 in the Winter

Image from Freestocks on UnSplash.

I happen to live in Ohio where there is often a weird mixture of the four seasons of weather. For example, when it seemed fall has set in, summer returns and the sweaters and leggings you have pulled out have to temporally go away. Now, around here we have made our way into winter. Which means I have had to dig a little deeper into my collection of leggings to find the lined ones. I love the soft feel of the leggings and how they keep me warm when the temperature dips well below freezing.

For my wife Liz and I's winter time walks, I usually pair my favorite leggings with my furry boots and bulky soft sweater before I have to go outside and brave the elements. These days, I need to force the issue with my walks since Liz and I are going to visit the Florida Keys in January. So I need to do my best to walk as long as I can when we go. Since there is thirty days away, there is plenty of time to write about our winter vacation before it arrives. Such as my first time swimming as a transgender woman.

If I had my choice, I would choose winter over our hot, humid summers any day. I like the fashion and the fact it is easier for me to stay warm in the winter rather than cold in the summer. I know possibly, I may be in the minority of all transgender women who value the look and feel of bare skin in warmer times. While I remember vividly the freedom I felt when I could finally shave my arms and wear short sleeved women's fashions, over the years, the feeling has somehow went away. One way or another, I have traded the feminine feeling of leggings for the sensation of shaved legs in the wind.

Either way, the entire fashion process is one of the reasons I enjoy my transgender womanhood so much. The planning ahead for the seasons means so much and winter is just a portion of the process. Of course we will see if I am just as enthused if we get any sizeable snowfall in December since I have one Christmas lunch coming up with the Cincinnati Alzheimer's diversity council as well as a Yule get together with Liz's circle of friends. During which I will have the opportunity to explain why I turned down an interview with a local television reporter after the election. 

So there is quite a bit coming up in December, including awaiting the arrival of a new laptop I thought I would go ahead and purchase before the proposed tariff's go into effect driving prices upwards. It will be interesting to see how easy or difficult the set up will be. I am not very technologically advanced. The laptop was one of the biggest purchases I have made in a long time. It was an online Cyber Monday purchase so I did not have to put up with any lines or pestering sales people. Patience, along with many other attributes will have to be my main goals following trying out a new laptop in over a decade. 

Overall, the month of December is more enjoyable with the fashion and festive Christmas lights in the neighborhood. I have respect for those who put effort into holiday decorations since all the work I put into my second wife's extensive decorations 

It all makes up for the drab months of January and February. Being a trans girl in the winter is yet another challenge. 

Trans Bucket List

 

Image from Pepe Nero on UnSplash.

On my way to achieving my version of transgender womanhood, I started my trans woman bucket list.

It all started on the fateful night when I decided to go out and mingle with a group of professional women as an equal. Not as a man cross dressed in their company to see if I could make it in their world. There was so much else at stake that evening because I knew if I was successful, I could never go back to just living my life as a man. 

Once I was successful, I began to think of  things I could accomplish as a trans woman to add to my bucket list. Once I was accepted as a regular in one venue, could I possibly add another to increase where I could go to add variety to my evenings. For the most part I was successful in being accepted. Even to the point of being thrust into a diverse small group of acquaintances I could regularly socialize with. The group included the sister of one of the bartenders, a lesbian, a couple men and an exotic dancer to name a few. All of this occurred before I met the transgender woman and two lesbians I socialized with on a regular basis.

Also on my bucket list at the time was how was I going to handle my sexuality with men. I almost found out when I became attracted to one of the men in the group. Or should I say he was becoming intrigued with me. All the way to him seeking me out on the nights when I was there all alone. I felt comfortable talking to him and even enjoyed his company before he switched jobs and abruptly moved away. It turned out there were very few men on my bucket list but even so, there were a couple which left a deep impression on me. 

Both of the men were met through social media dating sites and happened after I sorted through an amazing amount of trash responses. Because I was careful to meet any responders in a setting I approved of, we met in my regular venues I felt safe in. Both treated me with respect and I leaned a little of how it would be to interact with an interested man as a woman as I was wined and dined. It was terrifying and exciting at the same time. I still remember both dates and how special I felt but on the other hand, I never really lost my attraction to women. As impossible at it seemed to me at the time, I was headed towards being a transgender lesbian...if I could be accepted. 

I continued my quest for a new bucket list as I learned how to be a woman from other women. It seemed nightly I was learning new ideas such as I did not need a man to be validated in my new life. The lesbians I were around were both very strong and confident in their own right, so I could be also. 

Then, there was my relationship with my wife Liz which has been going on for over thirteen years now. I never though I would find another person who would be serious enough about me to want to build a relationship at my age. But I did and amazingly, Liz found me on a dating site defying all odds. 

Just when I thought I was done with my bucket, it became filled with happiness and I hope to keep it that way. 

Trans Girl in a Furniture Store

Image from Nathan Dumlao
on UnSplash

Once I had progressed to a point where I could comfortably navigate my way around in public as a transgender woman, when Christmas rolled around I thought I could do my shopping as a woman.

Since previously I had helped gift my second wife an oak roll top desk, I thought if I could find and afford a matching oak book-case, I would buy it for her as a Christmas gift. Before I did, I needed to find a store which carried the book-cases. As it turned out, the closest one I could locate was fifty plus miles away in nearby Columbus, Ohio.

Before I made the trip, I needed to make sure I planned out when my wife would be working and not at home for the amount of time it would take me to go and buy her gift. Once I did that, I needed to add in my "prep" time to get ready to go and I was all set for yet another gender adventure into transgender womanhood. 

For the evening, I chose my favorite business professional outfit at the time. A black pantsuit with heels, my best makeup job and shoulder length blond wig. Plus, since it was cold that night, I could wear my long, wool coat to stay fashionably warm. 

As I left the house and headed for Columbus, I was nervous about how I would be received and if I was able to purchase a bookcase would it fit in my SUV and who would load it. I was so afraid of being "discovered" and shunned at the store. But as I entered the place, my fears began to dissolve as I blended in with the other shoppers as I looked for what I wanted. It turned out about that time, my first taste of feminine privilege kicked in. First of all, I did not even need to find a clerk to help me. Before I knew it, an eager guy was ready and willing to help the tall blond in her heels and pants-suit. 

He asked me if I knew what I wanted and in a soft voice I told him exactly what I wanted. In no time at all, he showed me to a cashier and I bought my precious gift with a smile and then wondered how I would ever make it to the car. Again, I should have not worried much at all as two able bodied young men quickly showed up to load my book-case. I loved it when one of them even opened the door for me as we were headed to my car. Brimming with gender euphoria and confidence, I hurried home to gently unload my gift and hide it in the garage. 

Sadly, I went through the process of returning to my male world in record time as my wife was due home at any time. Somehow I managed and was ready to act as if the evening never happened. At least this time I could tell her the truth when she was asking how my evening went. I told her I went shopping for her and to stay out of a certain area of the garage until Christmas. For once that was how the evening ended without a fight or me having to lie about going out as my femininized self.

The internal excitement of what I had accomplished that night stuck with me for quite a while and when it wore off, I had more confidence to shop for her as a woman in the world so I shopped again in other venues for gifts.

Being a trans girl in a furniture store was just the beginning. I will have more experiences to write about as Christmas gets closer.

In the meantime, thanks again for reading along. Your input means so much to me and comments are always appreciated. 

Act Fast...Think Later

Image from VT on UnSplash.

Many times as I was traversing my very long and complicated gender journey, I ran into situations where I needed to act fast and think later. Or, wow, did I really do that?

Perhaps the most impressive example was when I had an ill-advised attempt at wearing water balloons as breast forms. While I loved the feel and bounce of the balloons, deep down I knew the danger I was facing. Someday, I would go too far trying for bigger breasts and one would explode in public. Of course I kept going with the balloons until the possible happened. I had an explosion of water in one of the venues I always went to. When it happened, I needed to act fast and head for the rest room. Fortunately, I made it and there was no other women in the room so I could enter a stall and clean up. Then I was able to make a quick exit from the venue and head home. I don't know what I would have said if anyone had noticed. Maybe I was pregnant and my water broke? 

After the water balloon disaster, I needed to think about what I would do for breast forms which were not as dangerous as water balloons. At the time, silicone breast forms were just becoming popular but were still out of my budget. What happened was a cross dresser acquaintance of mine went on a major purge of his feminine belongings and gifted many items to me. Including a set of breast forms. Since we were basically the same size, the new silicone breast forms worked well and were the proper size. And, most importantly, I didn't have to worry about disasters coming up.

Perhaps you have heard the term "muscle memory" which essentially means you keep repeating an action until it becomes second nature to you. In my earliest days of entering the world as a novice cross dresser or transgender woman, I spent many of my leisure hours attempting to learn how a woman moved and walked. When I did, I am sure I provided many a stranger with a humorous look at my male self trying to move like a woman. In fact, one night when I was in what I thought was a deserted box store, I caught myself being stared at by a guy who suddenly appeared out of nowhere. He was probably a plain clothes security person getting a kick out of seeing me practice. At any rate, I acted fast and left the store and thought later about where I would do my practices. 

Acquiring the basics to present well enough as a woman was difficult for me and required hours of effort and will power. Along the way, I experienced more situations of acting fast and thinking later than I can remember now. I do remember vividly the night when a lesbian friend of mine wanted me to approach another woman at a lesbian mixer we were attending and see if I could get her name. I acted fast and said yes, when in fact I was petrified of being the proverbial "wing person" for another woman. It didn't really matter anyhow because I never got a name. But later, in another venue I got even when I was kissed by another lesbian as my friend sat by herself. 

Maybe acting fast and thinking later just came with the territory of my transgender womanhood. I had always been an impulsive person and nothing really changed except for I had a whole new platform to work with. I think too, when I began keeping company with other women as a transgender woman, my instincts needed to change. I learned quickly how mean other women could be to each other and how difficult it was to watch for passive aggression. Early on, I needed to survive many passive aggressive encounters in the world with other women. 

It was all just a part of the learning process on my gender journey and one I had to face to make it to my dream.   

 

I Chose Me

 

Image from the JJ Hart archives.

In an extension of yesterday's post, I decided to explore how I chose my inner feminine soul over my forced male existence I was rebelling against.

Basically, the deciding factor came down to how natural I felt as I cross dressed in the very beginning of my gender path to freedom. Very early, I remember vividly how I so desperately wanted to be more than just a boy dressed as a girl in the mirror. I wanted to be the girl. Why did I have to put up with all the male problems I had so much a problem with. 

As I embarked down a very long path to having the courage to finally living as me, as I write about often, the longer I waited, the more baggage I needed to do away with. Often I was my own worst enemy when it came to having any success as a male as it seemed every male privilege I secured someday I would have to give it away. This extended to making any new friends. It was very difficult to be close to someone who may reject me when I set out to live a new life and let the old one go. 

At the many milestones I encountered on my gender path, deep down, I needed to choose me. Especially when I learned there would be more than one major transition I would have to take. My primary go to example was the momentous evening when I suddenly decided I was done with being a cross dresser. I wanted so much more. It was the night I went out to mingle with other professional women getting off work at a bar/restaurant by the mall I always went to. The whole process was basically a mental move, in that for the first time I was going out in my mind as a transgender woman trying to be the equal of any other woman I met. I wasn't a man at all.  It meant the world to me when I was successful and knew right then I could never go back on my journey. Somehow, someway, I just had to be me.

My main roadblock was my second wife who accepted me as a cross dresser but always drew the line at any suggestion of me being transgender. Especially when gender affirming hormones were brought up. She rightfully saw her man she married slipping away and wanted no part of it.

Unfortunately for both of us, I had gone too far to turn back on my dream of living as a transgender woman. I was following my path the best I could and did not want to go back. Choosing me, over the life I had was the most difficult decision I ever had to make. The pressure was on to make my choice and for the longest time, I tried my best to live a life in both the binary genders. Plus, it seemed when I thought I had life all figured out, more and more questions arose. Like what was I going to do about my sexuality was a big one. Was I going to pursue men or become a transgender lesbian. 

Once I made my decision, the rest was easy. The pressure was off and I was free to be the me I should have been all along. What a relief!

Trans Girl Preparedness

Image from Ben White
on UnSplash. 

Since it took me approximately fifty years to fully emerge as a transgender woman, I had plenty of time to prepare.

The challenge comes when we trans women or men need to begin from scratch. We did not benefit from a gender peer group such as other girls to have sleep over parties and experiment with makeup and clothes. No one to tell me I looked like a clown in drag. I learned I needed to resort to the mirror for help but sadly ran into problems when the mirror had the habit of lying to me. I could still look like a clown and the mirror would not tell me the truth.

What I did was go out to into the public's eye and receive an honest feedback on my appearance. In the beginning, the experience was brutal as I was met with stares and even laughter. Many times, I could not wait to go home to the safety of my own room to start over again. I kept thinking, regardless of all the negative feedback I was getting I could do better. For the first time in my life, I needed to decide what I wanted worse, to hide in my closet and not advance toward my dream of ever living a feminine life, or advance and begin the learn the basics of makeup art and fashion which at the least fit me. I found the entire process to be exceedingly difficult for me. 

Spoiler alert. I did learn the hard way what I needed to do to blend in with the rest of the women around me. It was a powerful lesson to learn when I found out how women ruled in their own worlds and how I could join in.  In the meantime, I was learning how to erase my male past and start over. To make matters worse, my male self naturally fought against the gender change to transgender womanhood he was facing. 

Through it all, I was naïve to think I was progressing towards my gender dreams. I thought that just doing my best to look like a woman was all I had to do. When I entered the wild and wonderful world of women, I was excited yet terrified of my future. After all, I was risking all of my male life as I had known it. What would become of my family, friends and income? To arrive at the point of knowing all my gender questions, I just had to be better prepared.

At that point, I started to go out into the world with a purpose to learn if I could make it as a transgender woman at all. Primary issues remained such as communication problems. Plus, I went the distance to try to stair step my way into an increasingly active public community. I purposely tried out more and more challenging situations. Away from the no challenge opportunities I was facing in clothing stores and malls. I even tried to avoid the book stores and antique malls I had become fond of but never presented any sort of a gender challenge to me. I needed to feel OK with who I was, where I was before I was able to move on. 

At the same time, my male life was successful and was pushing me to stay the same and not transition into a women's world even farther. All the struggle did was wreck my mental health. What I did not recognize yet was my feminine self was my dominate personality and needed to be freed. The harder she fought, the harder he fought. Finally, he gave up and I found a deep seated relief I had never known before.

Primarily, after all the time and effort I put into changing my exterior gender to what my inner self was always telling me, was the reason I felt better about my life. Sure, the gender affirming hormones I began to take made the transition easier also but bottom line, I was just prepared to do what came naturally and live it.  

Re-Approval

 

Bar Mitzvah image with wife Liz on left
and my daughter on right.   

In previous posts I have referred to my recent Thanksgiving trip to my daughter's in-laws. 

Fortunately the one hundred mile round trip went without issue and we even arrived just a bit early. For the first time in several years, there were several people there I did not know. For some reason, meeting new people is always a challenge to me. 

This Thanksgiving one of my hopes was my transgender grandchild and their partner would be at the dinner. They were (they is their preferred pronoun) and visiting with them was fun and interesting. It turns out they are just weeks in graduating from "The Ohio State University" with a degree in nuclear engineering. Most certainly, NOT a chip off the old block because I can barely add and subtract. On the other hand, I never set out to ever be a role model in the transgender world. It has been exceedingly beautiful to me to be a role model for my transgender grandchild. 

Also fun was when a group of women at the dinner gathered around me after they helped clean up. Being accepted in women's only spaces is always special. Of course much of the conversation revolves around children and my first wife was even in the group. Since everyone knew my daughter was in the group, there were very few questions of me. I was too busy just enjoying the feelings of acceptance around me. Which for whatever reason was missing in my earlier years of coming out. Very few people knew me before I transitioned and many of them were in the room where I was. 

It was a difficult time transitioning in front of my daughter's in laws but not as difficult as trying to come out to my ex-brothers right wing Baptist family. I was accepted so completely in my daughter's world and beyond, I was invited to stand up and speak before a crowd of people during another of my grandson's Bar-Mitzvah.  I was very nervous but did my best and again I was impressed with the acceptance I felt from the Jewish Temple where the event occurred.

All of this helped me develop who I wanted to be as a novice transgender woman. I thought I knew but until I did it, I did not really know all it would mean to me. I needed to go so far past just presenting as a woman the best I could all the way to creating a whole new person. When I did, most certainly, I had my ups and downs with the entire process and I needed all the acceptance I could find. Included was all the re-approval I could get. 

That re-approval came recently at our Thanksgiving dinner. As with so many other women, they don't know how much they have done with me to help me along. It meant so much to have the chance to  recharge myself for the future.  

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.

Happy Thanksgiving?

As I sit here watching the Macy's parade, it brings back all sorts of bittersweet memories. 

Looking back, Thanksgiving and Christmas were the two biggest days of the year for my second wife. She went all out for both, often feeding up to twenty people for Thanksgiving. Our door was never closed to anyone who needed a place to socialize and eat. The day also marked the beginning of a very serious stint of putting up all of her extensive decorations for the season. 

At the time, I took it all for granted and thought it would go on forever. As I grew older, I learned the hard way nothing lasts forever. I am fortunate in that I still have an extended family to celebrate  Thanksgiving with. If not for my daughter and my wife Liz, I would be joining no one for the holiday.

I used to have blood family with a brother. A decade ago I came out to my only brother and sister-in-law. I was naïve and thought I might receive the same positive reaction I had from my daughter. I was wrong and was told they did not want me at the family Thanksgiving Day dinner. Naturally, being  shunned  because I was coming out as my authentic self hurt me deeply. My brother and I have not spoken since. 

However to make up for it, I was invited to my daughter's in laws for the holiday. Plus I made up for the slight from my brother when I was invited to small get togethers in Liz's family when her Dad was still living. 

In the transgender world, sadly I am often not the example, as so many in our community have no family remaining to socialize with. Mainly because they were not accepted by their families. It is especially cruel when you have to remember times with the family by yourself.

On this Thanksgiving, I hope you have someone to socialize with. Even if it with a local LGBTQ organization. Many in our area often offer dinners you can participate in. 

Regardless, I hope you have a good turkey day!   

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.    

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.

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. 

Trans Woman in the Sisterhood

 

JJ Hart on left out with Friends.

I write often concerning my gender transition into transgender womanhood. 

Sometimes I wonder if I emphasize the complexity of doing it. Securing a place for me in an unwanted male world seemed to be so simple. Men have just a few power bases to interact with as they proceed through life. Such as money, or athletic prowess. Plus many males never have the chance to grow into manhood at all and never mature into quality human beings. 

Women face the same hurdles. Many females never make it  to womanhood. Which is a socialization process. Transgender women face additional obstacles during their journeys to be accepted into the sisterhood. As my second wife always told me, I did not really know the gender processes cis-women go through and she was right. I had not earned my right to be there...yet. It was not until I made it out of the mirror and into the world did I begin to learn what she meant. In many ways, she forced me to learn it on my own without her help. She was much wiser than I was but I was stubborn and determined to learn on my own about what being truly accepted into the world of women meant.

First of all, I needed to discover women operate in a parallel universe than men and somehow I needed to slide behind the feminine curtain and learn from other women how their world was run. I discovered that just like men, there were the alpha women who once they accepted you, you were in. With women, the difference was they were much more layered than men. Take appearance as an example. While I started out obsessing on how I looked, other women around me were noticing how I acted. I needed to walk a thin line with my communication efforts with women. On one hand, I was the quiet observer of what was going on but on the other hand, if I was too quiet I was coming off as too aloof or worse yet, bitchy. In the end, I was able to walk the communication tightrope and survive in a new exciting world as a transgender woman.

The biggest surprise I continued to have was how layered the whole experience was and is. Take conversations about children as an example. Women who have birthed kids share a special bond with other women who have done the same. I needed to interject my daughter and grandchildren experience on occasion without going too far. I felt the entire process femininized me and kept me behind the gender curtain. Being apart of the group was good. 

After awhile, being in the sisterhood had it's rewards. I mostly socialized with two or three cis women all the time which kept any potential problems from materializing. I was able to be protected from being a single woman out by herself and learn about the life I wanted to live in the meantime. One evening at a time, I was earning my way into my own level of transgender womanhood. Many times the process was scary. Such as the evening I went to a pro-football game with friends but the offer was too good to turn down no matter how frightening the situation was. Since it happened when I was first climbing away from my dark closet into the world. 

In so many ways, I owe several women friends whom I always say helped me more than they will ever know. They ushered me into being a trans woman in the sisterhood. 

Ironically, it was only the beginning as I needed to keep building on the feminine experiences I was having. A prime example was when I moved in with my wife Liz in Cincinnati. When I did, we started to attend small meetup groups with total strangers which added to the layer of meeting and being accepted by other people. The entire process for the most part was very positive and a great way to immerse myself even farther into the sisterhood. 

It is In Your Nature

Image from Hannah Popowoski on 
UnSplash

Following my fifty year battle with my gender issues, I just gave up and went with what felt so natural to me and completed my transition into transgender womanhood.

It was certainly a long drawn out journey of self discovery. It was full of ups and downs as I gained my footing along with confidence as I learned to just be myself. Looking back, I don't know what took me so long. Perhaps I can blame it on my male self wanting to hold on to the lifestyle he worked so hard to survive in. He put up quite the battle before giving in. But give in he finally did. 

When I finally began to explore the world, I learned how much of it was run by women and in order for me to survive, I needed to get along one on one with the other women around me since men rarely showed me any interest as a person. Women on the other hand were curious why I was in their world and I was somehow valued for being there. Perhaps it was my honesty showing through, which I gained from jumping the gender border into their world. I don't know for sure but I loved the attention I was getting. 

It was in my nature, because I had always valued the women friends I had over the very few men friends I ever was capable of having. I just did not fully ever recognize why until I was fully allowed to play in the girl's sandbox. Before I was allowed in though, I needed to earn my way in. I had to show my true nature was feminine and I needed to learn the rules of a brand new gender game. For example, I found myself in a world where passive aggressiveness ruled and a smiling face did not mean it was a friendly face. Much different in the world of men I was used to. It all was more of a mental game than I was used to also as I tried to anticipate where another woman was coming from. Especially when I came down to interacting with their men. On a few occasions, I came too close and felt the claw marks down my back for doing so.

The whole process just made me stronger and more confident in the woman I was becoming. Quickly I felt as comfortable in the new world I was in as I learned how the gender game was played. Women are more apt to form cliques than men who form teams and instead of finding the alpha male for acceptance, I needed to find the alpha female who was running the clique and I was in. 

Once I was in, my life became so much easier. Primarily because I did not have to fight being two genders anymore and the inner woman I was hiding for so long had her chance to run the show. She took to the process naturally. The only thing she did not do was harass me about why it took me so long for her to take over. Which she had every right to do. More importantly, I found she was a good person and got along with people including the all important world of other women. Essentially I found I good set and enjoy the show.

Of course before I could enjoy the show, I needed to understand the process of how to blend in with the world as a transgender woman. It was difficult putting my old male ego aside and realizing I was never going to be the most attractive woman in the room, I could present well enough to survive if I had the confidence to do so. 

What I really learned was, it was all in my nature to do so and if I relied upon it, I would be fine.

Engineering the Envioronment

 

Image 
JJ Hart.

As I transitioned into an increasingly feminine world, I faced many difficult issues.

I was keeping very busy with all the new sights and sounds I was facing. It was all so exciting while at the time, all so scary. Here I was trying to survive in a new gender world I so desperately wanted. Basically, with no training as I was only a very serious observer of the world of women and was never allowed behind the invisible gender curtain. 

I found out quite early I needed to engineer my own environment. Mostly, as I said, I was flying blind and needed all the help I could find. I was immersed in losing all my old male privilege's. I survived losing a good portion of my intelligence and learned how to be mansplained on many levels along with changing how I viewed my own personal security. Instead of thinking I was safe in unlighted dark spaces, I began to look for safer well lighted areas. All lessons cis-women learn at a young age. 

Once I learned I could basically dress to present properly with other women where I was going, I began to engineer more places to go to test my future into transgender womanhood.  Sometimes I was successful and other times I wasn't, mainly because I chose the wrong venue to go to. For example, bookstores were more gender friendly to me than redneck bar venues where single women rarely ventured anyhow. It took several hard earned lessons such as having the police called on me before I learned my lesson and stayed in more friendly environments . Again, experiencing what cis-women already knew. 

Ironically my journey took me to the spot some call the impostor syndrome. It occurred at all times and without notice. Such as during girl's nights out and other times when I was succeeding in living in an exciting new world. It was frustrating when the feeling slipped in which was telling me I should not be there at all. Ruining the good time I was having. 

The whole process forced me into pursuing and engineering whole new levels of my gender existence. Once I thought I had controlled everything I needed to learn to live my life as a transgender woman, something else arose to prove me wrong. Communication as a trans woman with the rest of the world who were primarily other curious women became a strong focus of mine. If I could communicate properly with other women, I had a leg to stand on to survive in my dream life, without it, I had nothing' and the time and effort I had previously put in would go for nothing. 

I was never an engineer in anything else I tried in life so all of this was new and different for me. I was also a bit of a quitter when it came to finishing a project. Completing my journey into transgender womanhood was easily the most difficult and extensive project I had ever contemplated finishing. All along the process just felt so exciting and natural, I had the best and worst times of my life as I kept on going until I reached my dream goal.

Finally, I learned the environment I was in could be trans friendly for me.  Hopefully, in the new world we are facing in the future, we can maintain it.