Transgender Procrastination

 

Image from JJ Hart

During my life, I have developed with an excessive amount of procrastination. Who knows, maybe it started when I put off doing my homework until the last minute. Later on, I began to connect the dots to me pursuing a life as a transgender woman. In other words, why did it take me over a half century to finally decide to leave my male life behind and the confines of my dark gender closet.

The easy answer is I kept putting off what I did not understand or want to face about myself by cross dressing my life away. To be certain, it was a series of stop-gap measures designed to help me survive life at all. When I was able to cross dress in front of the mirror or later at transvestite mixers I attended to see for the first time, others who perhaps shared the same gender views as I did. Ironically, I found I was wrong as I found most of the others at the parties were still a bit (or a lot) different than me. I did not quite fit in with the transsexuals or the cross dressers who were seemingly still stuck with their male selves which they were still attempting to deny. 

Still, I survived and slowly began to carve out my own life on my own terms as a transgender woman. Of course, even then, I still was the mistress of procrastination. Increasingly as I began too seriously explore the world as a transgender woman, I could not procrastinate any further. The result was I needed to merge my conflicting genders the best I could. The holidays proved to be the best time for me to try to do it. 

I have already written about my adventures shopping for my second wife when it came to buying her a matching oak bookcase and my time shopping for the perfect garden accessory. As I have promised in the past, I have not written yet about my times searching the antique malls for the perfect vintage gift for my wife. The added benefit was I could complete my Christmas shopping as a woman.

It just so happens, one of the largest antiques malls in the Midwest where I lived was located in my hometown. It gave me extra time to shop since I did not have to drive far to get there to the mall. I had several favorite things to do once I arrived and made a last second check of my hair and makeup in the car mirror and went on in. The benefit of vintage shopping for my wife was at the same time I could admire myself in one of the many available mirrors of the vintage furniture for sale. 

The furniture was not in my budget but items such as vintage seed boxes were. In fact, during those days, the seed boxes were a hot item for gardeners everywhere, so they were pricey. Still, I persisted until I was lucky to find one from another company, she did not have in my price range. The other benefit of shopping in the antique malls was I could really relax and enjoy the experience. Back then, the feeling of my feminine clothes and the interaction I was having with the public was so new and exciting. Plus, I could not wait to see the look on my wife's face when she opened the gifts I found for her. Back in those days, we had three Christmas gift celebrations. Two with each of our families and one just between ourselves. The giving of gifts between us always came last and always included the gift or gifts she reserved for my feminine self. 

My procrastination always extended to shopping at the last minute. As a trans woman or not. Perhaps I was addicted to the excitement of waiting until the last minute to find and give the perfect gift. All tempered by the fact I was shopping as my true self.

All of the experience added to me not waiting any longer and finally deciding to take a huge weight off my shoulders and do the right thing. Quit trying to live a lie as a man and begin a new life as a transgender woman. Facing my truth led to the end of my gender procrastination. 

The Stare

Summer Image Dining Out
by JJ Hart.

 
Last night, my wife Liz and I went out to eat with her son as an early Christmas gift to him. 

We went to our favorite restaurant, and they were packed with early dinner guests. Since they normally turn their tables quickly, we were not overly concerned about being seated in a timely matter.  I need to mention also, I have never had any problems at the venue with being treated as my authentic feminine self. Last night could have been a little different. But was it really?

The surprise came when we parked and a woman looking out at nearby window was staring at me. Before we even came in the restaurant. I ignored her, and we went on in and were seated. It just so happened we sat near to her where she could continue to look at me. Then the stare down became more serious as again I tried to enjoy my dinner and ignore her. 

Finally, after I glanced her way a final time, she was smiling at me, which could have meant many things. It could have been she spotted me as a transgender woman and was ready to make a scene all the way to she was just being friendly. So, I decided to smile back then go back to my dinner as if nothing happened. It worked. From then on, when I quickly looked back at her, she had obviously lost all her interest in me and was talking to the other woman she was with. I never saw her look at me again.

So, it turned out I won last night's battle, but I know I am a long way from winning my overall transgender war. In an earlier life, I was ravaged by testosterone poisoning which I face to this day. Which means I have to work very hard to obtain any of the passing privilege I may have earned when I was younger. Plus, now, with the added mobility issues I face at the age of seventy-five, it is difficult now to walk at all. Let alone walk like a woman. 

Still, I refuse to accept defeat and walk as far as I can daily, and I will not give into in any stray transphobes I may run into. Who knows, maybe the woman last night was just trying to be friendly.  After the previous disastrous election, maybe I am just paranoid. I know I am fortunate also to have my wife with me most of the time to run some sort of interference for me if I need it. However, I know I need to fight my own battles when and if they arrive. 

Perhaps the biggest test I will have is coming up in a couple weeks when Liz and I embark on a bus trip to the Florida Keys. There will be plenty of tests on my restroom presentation to see how much I have learned over the years. 

I will see how many stares I will receive. 

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.

NOT for Entertainment Only

 

Image from Alice Alinari
on UnSplash

As I went along my path to transgender womanhood, I found the journey was never a choice and was not for entertainment only.

My journey did not begin that way. Similar to many of you, I started by exploring my mom's underwear drawer and wearing what would fit. All of that was seemingly innocent enough unless I was caught. Then there would undoubtedly be hell to pay, along with a trip to a psychiatrist. Later I would wonder if my mom ever knew because her underwear was stretched out, but she never approached me at all. 

It was all fun and games until it wasn't. Slowly, I learned wearing girls/women's clothes was not for entertainment only. I was becoming increasingly serious about it. For the first time in my life, I was obsessing over how I looked. How was my makeup and very limited access to a wardrobe appearing in the mirror. I even went as far as shaving my legs when I thought I could get away with it. In addition, I did my best to study the other girls around me. I did not know it then, but I probably was wearing makeup before a few of the girls I knew were allowed to do it. At the time when I could not seem to muster the same passion for building the model cars I had and painting them well, makeup was an entirely different challenge and one I could not resist doing my absolute best at doing well. With no help whatsoever. 

I found, for the first time in my life, I was completely serious about doing one thing and it was being a girl. Not just looking like one. It took me years to learn just gazing at my reflection cross dressed as a feminine person was just not enough. I needed more. My problem was early on was having the budget to do anything such as being able to afford having a nice wig. It was not until my college days until I could buy a long blond wig I cherished for years. Spending all the money on one specific fashion accessory proved my passion to look good was not for entertainment only. I was really serious.

Of course, then I really started to step up my gender game. When I was released from my military service, I began to seriously explore the world as the feminine trans woman I was destined to become. As I write about often, my journey was filled with ups and downs and my mental health suffered. Definitely not the way I thought it would be when I looked at myself dressed as a girl in the mirror early in my life. What I never had a chance to consider was I was not a transvestite or cross dresser at all. In fact, I was a transgender woman and needed to accept it. I was never in it for the entertainment and my life depended on a successful outcome. 

What I mean is, I needed to stop all the self-destructive behavior I was exhibiting as I sought to destroy everything successful, I had ever done. Along the way, I had tried to lose jobs, drink too much all the way to trying to kill myself with pills. Never realizing how much I had to live for if only I followed my transgender path far enough. 

I wonder now, if I had realized how difficult my journey would be and not be entertaining would I have ever undertaken it at all. I also realize now, I never had a choice, and my life would have been better had I realized it sooner. I would love to get back just a tiny portion of the stress and tension I lost during my life as I worried about my gender. Outside of a few therapists who tried to help me by telling me the truth about myself, I was on my own. My life was never for entertainment only as I followed a gender path full of turns and dead ends before I discovered my truth in my transgender womanhood. 

Mountain of Hope...Mound of Ash

 

Image from JJ Hart

On occasion when I was following my very long path to transgender womanhood, I did experience enough hope to keep moving forward towards my ultimate goal of living a fulltime feminine life. 

Those were the days I was on top of the world and felt good about my life as a whole. Sadly, too many times my dreams were crushed mainly with me making poor gender decisions. Those were the nights I returned home with tears in my eyes following brutal interactions with the public. I was at the least stared at and at the worst laughed at to my face. Since I had only the mirror to blame for lying to me, I needed to find a better way to improve my presentation as a novice cross dresser or transgender woman. 

Really, the only recourse I had was to keep going out hoping for the best and expecting the worst. Very gradually, out of sheer will power, I did become better at my craft and my confidence grew. I was climbing my mountain of hope and staying there. Sadly, my only mound of ash came when I was discovered by my second wife when I was returning home after a night out. Predictably a massive fight would happen, and feelings would be hurt. It wasn't until years later when I finally had the courage to face my gender truth and finally transition. By that time my wife had passed away and it was a moot point. Following her passing, I found I had another mountain to climb. 

My mountain was one of loneliness. For the first time in over twenty-five years, I was by myself with only my two dogs to take care of. No other person to worry about disappointing with all of my gender adventures. It did not take me long to decide which direction to go with my life. My inner feminine soul was screaming to be let out and for once there was nothing to restrain her. She was my woman, and I was her.  With new enthusiasm, I began to climb again. Sure, there were still setbacks and problems with my new life. A primary example was when I tried to date men and was constantly stood up on potential dates. Fortunately, when I began to be accepted by lesbians, I found I did not need a man to be validated as a woman. 

When I climbed my gender mountain, I began to begin too clearly see what was going on around me. As all the clouds and doubt parted and I could see there was only one path for me to pursue. I finally gave up on my male self, gave away all his clothes, started gender affirming hormones and never looked back. 

When I finally freed myself up to be me, I never had felt better. It was a huge weight lifted off my shoulders which I had carried way too long. Since I am afraid of heights, climbing my gender mountain was never easy but I made it. 

Trans Fun?

 

Holiday Image, JJ Hart author.

Are we having any fun yet as the holidays are upon us? 

Certainly, it is a tough time of the year as transgender women and trans men face the daunting task of facing unapproving families. Too many of us face a lonely existence this holiday month. In many ways, we are uniquely qualified to face the challenge. For those of us who were ravaged by testosterone poisoning and not gifted by natural feminine features, our path is a steep one to finding any acceptance at all in our transgender womanhood. 

In my sense, there was only brief gender euphoria moments during too many instances of rejection by the public. Every now and then, I would have moments of fun when I briefly succeeded at my goal of successfully presenting as a woman. Then, all too often I would ruin it all by not knowing how to move as a woman or more importantly having any idea how to communicate with the public as the person I had always wanted to be. 

Through it all, I did have enough fun, or at least satisfaction to keep moving forward. To be certain, there was a difference between having fun or being satisfied with what I was doing. To be satisfied meant deep down I felt natural when I was pursuing my feminine dreams. To put it another way, there was a flood of water under my gender bridge primarily in the decade after 2007 when my second wife passed away and opened the door to a total transition into transgender womanhood. If I wasn't hanging out with lesbians in their venues, I was finding my way in big sports bars as a regular. Slowly but surely, I learned I still was alone on my gender path, even though I was meeting and learning from a few of the cis women I stayed close to. It was difficult because I had always trained myself to keep everyone else at an arm's length so I would not be hurt. The difference was now I was finally at the level personally where I wanted to be as my authentic self so I could accept new friends.

If I had liked, it or not I had finally reached the bottom-line where I had always wanted to be. When I did, I began too actually relax and enjoy myself. Which means I was having fun, regardless of myself. Perhaps I was fortunate in that my path forward was complex but maybe not as complex as is the norm these days. Social media contacts were just becoming the norm and maybe it meant the tons of trash I needed to sift through to find my wife Liz was destiny and not luck since she actually sought me out online after reading my profile. Then, there was my public persona which I don't necessarily recommend because I was going out to venues as a single transgender woman. Back in those days at least, one did not have to worry about someone else putting date drugs in your drink while you were not looking. 

Looking back, I did have fun during those days and primarily it was because my confidence in my new self was increasing because of the people around me. I could copy what they did as women and do the best I could. Which was better than I had ever done before. I had paid my transition dues and was ready to face the future.  

Answering the Call

 

Image from Alexey Elfimov on UnSplash.

On occasion I am sorry to say it took me over a half a century to answer my gender call. But thankfully, I finally did take the call and listen to the urgent message. 

Please keep in mind I don't count all the years I attempted to cross dress my gender issues away. As I often write about, all cross dressing did was provide me with a quick fix. After I dressed as a girl, I felt better for a while before the same old tensions of life with gender dysphoria set in. The problem was, deep down I knew I wanted to do so much more than look feminine, I wanted to be feminine. 

One of the few good things which came from my gender struggles was practice made perfect. Even though I knew I was the only one who could see my progress with makeup and clothes, I stuck with trying to improve every time I cross dressed. It was so difficult for me since I only had the mirror to answer to when checking out my progress. The problem was the mirror was so good in telling me everything, but the truth and I tried to keep in mind I might look good, for a boy in drag. Not as an actual girl. In other words, I learned I needed to hold myself to a higher level than other cis women I observed if I was to survive among them. 

The entire process was so difficult for me since I had never been detailed orientated in my life. Just getting by was not going to be the way to go. I was fortunate when I encountered professionals in the makeup world who helped me along. One in particular came following a transvestite-transgender party mixer I attended near Cleveland, Ohio years ago. After the mixer slowed down, the organizers provided several makeup professionals to provide free tips to whoever had the nerve to ask. On that evening, I am happy I put my ego behind me and answered the call for much needed makeup assistance. The catch was I needed to remove all my makeup and wig and let the professional start over. His work and results were amazing, and I even understood all the tips he was trying to tell me. The end result was I was flooded with compliments and my gender euphoria soared to an all-time high. Furthermore, later on that evening, I was even hit on by a guy in a straight venue I went to with other transwomen from the mixer. 

That night, I did not answer the call to stay with the guy who showed interest in me. My reason was, I was in a strange town with a person I did not know, and I did not know if he realized I was transgender. Not a good place to be at two in the morning. On the other hand, I loved it when the other "A-listers" from the mixer were jealous of me for once.

Along the way, I ended up answering enough calls to barely keep myself going. There were plenty of times when I did not know if my mental health could take it, and I could keep going. It was then when I took the all-important call to begin gender affirming hormones and change my life forever. I was sixty by then and knew there would be no turning back. After I did, I learned taking the most important call of my life turned out to be a life survivor for me. I remember the evening when I decided to answer my phone for the last time. All of the sudden the voice told me I was free to live as my authentic self and the relief I felt was tremendous. All my previous misgivings were swept away. 

Who was the Problem?

 

Image from Ben White on UnSplash

Looking back at my long journey to transgender womanhood, I finally discovered I was the true problem all along.

I was in shock. All this time I was desperately seeking someone else to blame for my gender identity issues. I kept thinking I was alone in the world and why did it have to be me. Remember too I grew up in the pre-internet generation before there was much if any real information available to gender challenged people. The struggle was real.

It took me years to figure out I was not a man cross dressing as a woman but rather I was a woman cross dressing as a man. To arrive at such a major point in my life required years of trial and error in the public's eye as a novice femininized person. To advance to the life I had always dreamed of, required a lot of work on one hand and confidence I could do it on the other. 

Somehow, I needed to work through all my paranoia I was experiencing and begin to enjoy my new life. I equate it now with learning to dance with a new partner and beginning to feel at ease with it. Primarily when I tried to perfect moving as fluidly and gracefully as a natural woman. Moving like a linebacker at a dance was out. It all was a major obstacle towards moving to my dream. Or could I ever hope to be able to live fulltime as a woman like I had seen others around me do. Then if moving as a woman was not difficult, communicating came along and presented the greatest challenges of all. 

The act of communication came up on me quickly. As I started to go out in the public's eye just to get out of the house as a woman, the better I became doing it. I learned quickly, how many other women wanted to communicate with me. For the most part, they were just being nice and wanted to know what I was doing in their world. Once they found out why I was there and I did not pose a threat, they wanted to know more. If I did not learn the basics of feminine communication quickly, then I would be the problem if I came off as unfriendly or even worse, bitchy. To work on my fears, I went back to the mirror to practice talking as a woman. It was bad when at first, all I could come up with was a scratchy falsetto which just would not work. Initially, before I began vocal lessons, I started with a quiet background voice as I tried my best to mimic the woman I was talking to. 

Perhaps the biggest problem I encountered was adjusting to the basic passive aggressive spirit of women everywhere. Primarily, I needed to learn a smiling face did not always mean acceptance from another woman. I was the problem when I treated smiles as acceptance and learned the hard way when they were not. I think I still have the scars down my back to prove it.

It turned out, my basic stubbornness to leave my male self behind was the real problem. All the stress and tension he caused over the years cannot be reclaimed.  In the end, I needed to put all the blame on myself. If I could have understood all my gender issues over the years, life would have been so much more pleasant for me. I am sure it all goes back to me knowing I felt better as a girl and more natural. I have no idea now why I waited so long. Except I did not want to give up all the materialistic items I had accumulated as a guy. It took a transgender woman to whisper in my ear that all would OK if I just had followed my heart and transitioned. Then I would not have been the problem at all. 

Joy to the World

Image from JJ Hart Liz on right.

Gender euphoria is so wonderful to a transgender woman or trans man striving to present themselves in the world as their authentic selves. On the other hand, it is often very rare to obtain. 

The brief moments I experienced euphoria in the world when I first went out as a novice trans woman or cross dresser, kept me going but barely. The reason was, I suffered from huge bouts of  gender dysphoria which wrecked my life. It seemed every morning when I woke up and looked in the mirror, would I see the same old male I never wanted to be or somehow see behind him and view the girl I always dreamed of being. My dreams even reflected my gender issues when I would awake following a very vivid dream where I was the pretty girl. When reality set in, I was very sad.

It took me years to realize I could fight back against my gender dysphoria and do more to live out my dream of living as a woman. Years of sorrow when I failed became years of joy when I succeeded. Progress was very slow at first as I went out shopping in the world and sought out every mirror I could find to restore my faith I was indeed a presentable woman just minding her business in the world. When I discovered most people did not really care about me, my life became much easier and took quite a bit of the pressure off I was feeling. 

Still, I needed more. On every occasion I could, I was out the door seeking new places to visit as my new exciting self. I was walking the gender border and feeling the joy on some of the days I was successful and torment on the days I was not. My main problem was trying to find feedback with what I was attempting to do. The only time I did receive any response was when I went to the small, diverse parties I went to at an acquaintance's house in nearby Columbus, Ohio. From transgender admirers to inquisitive lesbians, I had a chance to meet new people in my world and see how I measured up to them. I knew I could never be a beautiful as a few of the impossibly feminine transgender women who attended but just maybe I could elevate my appearance to a feminine level where I could get by. The parties also proved to be the initial starting point of developing my own new personality as a trans woman, so they were very beneficial.

As I experienced the joy of being my true self, something had to give. Sadly, the something turned out to be my male self and my marriage of twenty five years to my second wife. Both of them suffered terribly. Naturally, neither of them wanted to lose any power. My male self was quite comfortable in the life he had built and my wife did not want to lose the man she married, so I was in for very difficult times. What happened next was my mental health went into a very steep decline. I did not know where to turn and at that time did not have a good therapist to fall back on. Then I resorted to the worst possible choice when I tried to internalize everything. By doing so, I made everything worse. 

I continued to go out as much as i could but ended up just forcing the gender issue and losing any of the joy I had previously felt. It wasn't until I decided to begin gender affirming hormones and transition fully, did I begin to reclaim the happiness I felt. 

Was it worth it? Sure as I finally achieved my dreams of living fulltime as a transgender woman. I just wish I had the courage to do it sooner. Or as my second wife told me a number of times when we bitterly fought...be man enough to be a woman. 

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 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. 

Now What?

 

Image from JJ Hart

As I cautiously discovered I could make it in the world as a transgender woman, rapidly I kept coming to the conclusion of now what.

How would I face a whole new life without the old male standbys to fall back on. I had taken the time and effort to build a family, friends and a fairly successful job which I had to possibly give up. Naturally, I spent hours, days and weeks trying to figure out what I would do once I entered fulltime transgender womanhood. I had long since passed the point of just being satisfied with existing as a part-time cross dresser. 

Ironically, every time I was successful in public as a novice trans woman, I wondered now what I  have I done and what was next in my life. The problem was, I had several major roadblocks which were looming in my life, such as helping to care for aging parents and a spouse who was totally against me transitioning any further than I was. To diminish the impact of all the gender stress I was dealing with, I did what many males try to do and internalize all of my problems. Even though I was going out as much as I could as my authentic feminine self, the fact remained I would have to go back to my old unwanted male life sooner more than later. As Paula from the UK put it in response to a previous post:

"For me it was the depression that followed "putting Paula back in her box", each time I went back to being "him" it was like a bereavement, in the end it was bowing to the inevitable. Arguably transition was the most selfish thing I have done, but like so many others I was insufferable trying to maintain my male persona, in the end it wasn't so much choosing my feminine side as choosing life."

Similar to Paula, the entire transition process for me came down to life and death for me. Like so many other transgender women or trans men, I attempted suicide to relieve myself of the brutal gender related stress I was feeling. Fortunately now, I was unsuccessful and lived to write about the experience. In fact, it was one of the reasons I began to author a blog.  In order to help others. 

Perhaps you are wondering how now what worked following my attempt at self harm. I still was not smart enough to listen to my inner female and tried to purge my fairly extensive feminine wardrobe and makeup. It was during this time too, I began to notice my second wife's health was slipping badly and she would end up passing away at the age of fifty.

Then I really entered the now what part of my life. The door had suddenly opened for me to live my dream of living fulltime as a transgender woman. I followed my soul and began gender affirming hormones at the age of sixty and never looked back.

All the days of wondering now what were behind me. All the risks I took were with it as I began to happily live an authentic life. And, by the way, Paula thank you for the comment and thanks to all of you reading along. 

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.  

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. 

The Second Time Around

 

Image from JJ Hart.

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

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

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

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

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

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

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

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

Running and Hiding

Image from JJ Hart archives,

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

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

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

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

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

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

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

Trans Girl in a Sports Bar

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

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

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

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

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

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

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

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

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

De-Transition?

 

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

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

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

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

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

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

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

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

 

Was there Ever a Plan

Image from the JJ Hart
Archives

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

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

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

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

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

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

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

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

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

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