Trans Girl at the Symphony

 

Cincinnati Music Hall

I really don't know why but this experience usually slips my mind. Even though, it is one of the most dramatic experiences I have ever had. 

All of this happened several years ago when I was still attempting to navigate the world as my authentic self for first time. Also, my future wife Liz felt the time was right for me to accompany her to the Cincinnati Symphony Orchestra Christmas concert. The whole idea petrified me, but I could not say no and I set about preparing for what I could wear to a semi formal event. My first.

Fortunately, thrift shopping came to my rescue as I found a very sparkling gown to wear in black. As I prepared by shaving, applying makeup and doing my hair, my nervousness subsided a little as we waited for the Uber, we called to take us downtown to the concert hall. 

When we arrived, my nerves returned as we were stuck in a crowd of people waiting to go to their seats. The only thing which saved me was, no one seemed to be paying me much attention. When I sensed no one cared about me, I began to calm down. As far as the musical performance went, I admit I had never been much a fan of classical music, but I did the best I could to enjoy it, and I did. Once I calmed down. Ironically, I was very calm until the lights came up and intermission began. People were moving around which put me in danger of being discovered as a transgender woman. I was not, and the concert resumed. 

Before I knew it, the experience was over, and I could breathe again until we stopped at a venue along the Ohio River for a drink or two to celebrate the holidays and our relationship together. Once again, my nervousness increased until we settled in at the new venue. Again, we were treated very well. I even used the women's room with no repercussions which was becoming a necessity.

What I learned from the entire experience, I found if I did not try harder to expand my horizons as a transgender woman, I never would. Plus, there was never a better time in my life to do it. Because I was spending my time with Liz, it made the whole time so much more pleasurable.

The concert was only the beginning of me building my confidence in my transgender womanhood. Liz wanted to travel, so I learned to travel and again learn new horizons of fitting in with strangers as a woman. I viewed it as a layered trip to learn more and more about my new world. Most importantly, I learned to interact one on one with other women and basically ignore the men who were ignoring me. 

It all was an important springboard into my future desired life which I had to do in a hurry, since I had such a late start at the age of sixty. I can't stress enough, when I did start, despite my fear or nervousness, I enjoyed it immensely. The entire process, proved once again, I had made the right decision when I chose to live as my authentic self. Plus, I needed to discover for once and for all, who was my true self before I could move on with all the major decisions I needed to make.

As I said before, I had never been a real fan of classical music, but it started me down the path to a beautiful future. 

Always Running

 

Image from JJ Hart

Much of my life was immersed in running from my gender problems. 

As fast as I could, I changed jobs and even places my wife and I lived so I thought would make a difference in my life. The prime example was when I picked up and moved my small family from our native southwestern Ohio to the huge bustling New York City metro area to operate a fast-food restaurant. By doing so, I thought deep down I would be closer to a population which would be more friendly to my cross-dressing desires.  I only made it a year before the culture shock pushed me back to our native Ohio.

In the meantime, I did have several moments when I was in New York which I will always fondly remember. One of which was the night I actually got out of the house by myself without my wife and drove myself out to Long Island for a transvestite mixer I had read about. Once I was out, I had two major surprises waiting for me. The first of which was I was happy I found the venue at all. The second one happened when I tried to get in. There were two women at the door monitoring who got in or not. I was flattered when they refused to believe I was a man at all and asked for an I.D. to prove who I was under all the hair, makeup, and fashion. 

The second most memorable night was again when I managed to be out alone in the world as my authentic self. Quite unexpectedly, I was invited to a Halloween party by one of my female assistant managers. Of course, I did not to think twice before I accepted her invitation and began to plan ahead on what I could wear that my wife would approve of. Finally, I learned she would never approve anything I wanted to wear, so I set out on my own to come up with a costume I would have fun with. It turned out my short tight dress and heels matched perfectly with what the other women in our little group were wearing. Plus, the women were all tall and I really blended in well in our heels.  

As I said, the culture shock of NYC over Ohio wore me down and we ended up moving back. When I did, I immediately fell back into the whole cross-dressing culture I was in before. I was unhappy and hidden away from the world, so I found another place to move to and uproot our lives. The job I was working offered me an opportunity opening restaurants along the Ohio River in southern Ohio. A very conservative area to be sure so I needed to up my cross-dressing outings. Somehow, throughout the whole adventure I grew tired of having limited places to go and wanted another move to improve myself. 

This time, I tried to move back to the Columbus, Ohio area where I knew several very diverse friends in the LGBTQ community, specifically the transgender crowd. Following a lot of work, I finally landed the job I wanted, and we moved again.

Finally, I grew tired of all the running I was doing, and I needed to settle down and face my gender issues head on. It took me until I was sixty to realize I needed to make a change to a full-time transgender lifestyle. When I did, a giant weight was lifted off my shoulders and I went on to start gender affirming hormones or HRT. It was a wonderful way to live. 

Not Scared? In the Wrong Room

 

Image from Alexandra Gorn
on UnSplash.

I cannot begin to tell you how terrified I was to interact with the public when I first began to attempt to live in the public's eye.

One night in particular always stands out in my mind. It was the evening when I had pre-determined my cross-dressing days were behind me and I was going out as a transgender woman. Furthermore, I knew if I was successful, it would change my life forever. As I prepared for my big night out, I took extra care with my outfit, makeup and hair. I wanted to make sure I blended properly with all the other women I would be interacting with at an upscale bar I was going to which was heavily frequented by professional women who worked at a nearby mall.

Once I made the short trip to the venue and found a parking spot relatively close to the front door. As I sat in the parking lot, the pressure to go in increased dramatically. As I nervously checked and adjusted my makeup in the car's rearview mirror, again and again the fact was not lost on me I could be changing my life forever. By the time I gathered my courage to actually enter the venue, I could barely breathe and was gasping for air. 

It took me awhile to gather my courage and enter the front doors of the place and interact with the hostess stand. Deep down, I was hoping the hostess would be busy seating other patrons so I could sneak on through and find a seat at the bar. The short distance from the hostess stand to the bar seemed to be miles to me but I made it and luckily found a corner seat at the bar by myself. Plus, the bar itself was supported by two large thick pillars. I figured if I found a seat next to one, I could blend in and hide if I needed to. I did not need to hide as I was approached for my order by a friendly bartender. 

Immediately, my fears began to melt as I ordered my first drink and even started to relax a bit and watch all the other women who had begun to arrive at the bar to enjoy each other's company. As I observed the group, I saw no one was noticing me. So far, so good. No one noticed a very scared novice transgender woman in their group. 

Of course, this evening was only the beginning of my new transgender journey. I knew my life had changed forever. I could never go back to the old unwanted, boring male life I was living. To move forward, there would be many nights when I would be very scared. Somehow, I learned to feed off my fear to propel me forward. No longer was I a weekend cross dresser, I was reborn as a very serious transgender woman.

My end game was using fear to refine my push forward by putting extra time and effort into my fashion and makeup. That way, when I needed to walk past a crowd of strangers in a new venue I was in, I could do it without any issues. 

I finally decided, if I did not feel any fear at all, I was in the wrong room. Especially, in today's climate, it pays to always be aware of your surroundings. Maybe fear is a strong word, but awareness is not. 

The Gender Envelope

 

Image from Alexandru
Zdobau on Unsplash.

Sure, I spent or waisted far too many years before I fully transitioned into transgender womanhood.

I was too slow for such a long time actually pushing my personal gender envelope when I was busy telling myself I was no more than part-time cross dresser. I saw no harm in just doing my best to look like a woman until it just wasn't the answer I was looking for. The more I cross dressed and improved my feminine presentation, the more I pushed the envelope and looked for more. Very quickly, my yearly Halloween adventures just were not enough.

I began to wonder if I made a good impression at Halloween, could I make the same impression if and when I tried to go out in public as a novice transgender woman. Following many trials and error experiences, I found I could survive a public which largely did not care about me. The big error I always point out is when I was not receiving any attention to speak of as a woman, I began to dress trashy to attract the wrong sort of attention. I was mistakenly pushing my gender envelope the wrong way. When I finally began to understand the best ways to dress my male body and apply the proper makeup, did I begin to be successful and blend in with other women in the world. 

Once I had accomplished all of the fashion, hair and makeup necessities, I allowed myself to further push my gender envelope. When I did, I found myself needing to understand how women exist in the world. Or how do they communicate with other women and men. I had a quite a bit of catching up to do since I was attempting to catch a moving train heading down the tracks. I did not have the benefit of growing up female with a mother or peer group to guide me. I always point out; the passive aggressive system of interaction most women operate under was the most difficult for me to learn. Since childhood, I was always used to the full-frontal confrontational world men operate in so I was attempting to survive in a whole new world.

Once I did survive, I began to push even harder, ignoring warnings from my wife on what would happen if I was ever caught. I put the male gay bars behind me and moved on to big sports bars and lesbian bars where I could actually be myself. I thought I had reached my peak when a dear friend of mine invited me to a trip to a NFL Monday Night Football game in Cincinnati. Even though I was very scared at the thought of going, I could not turn down a chance to empty my envelope and lay my gender cards on the table. Since I am not really a gambler, I hoped the lifetime of preparation I put into this moment would serve me well. 

The moment did serve me well. As always, I survived and became a better woman for it. Plus, I learned the game was only the beginning. The life in my transgender womanhood I was going to experience, would be extremely fulfilling and everything I thought it could be when I started pushing my gender envelope.

Amazing

 

Image from JJ Hart

As I sat and watched a singer do a wonderful rendition of John Lennon's "Imagine" and watched the ball in New York drop to ring in 2025, I had the chance to look back and think about how amazing my life has been.

As in everybody's life, destiny stepped in and took me in directions I never thought possible. The entire process was how I perceive the supposed death experience people have when they die. In other words, they get to see their life pass in front of their eyes. If indeed that does happen, I may have to ask for a little extra time to view all of mine.

Over a long life, I have been so fortunate to experience so many things. Outside the all-encompassing world of gender for me, was when I managed to land a job in the Army with the American Forces Radio and Television Service in Thailand and Germany as a radio disc jockey. To put it into perspective, there were only sixty other troops in the entire Army who did what I did. Since back in those days, we were basically the only connection our listeners had with home, it was a very serious job. 

Once I had served my time of three years and was released from active duty, I needed to take on again my larger issues of gender identity. To do so, I undertook serious research and development. Any time I could such as Halloween parties, I began to explore public reactions to my femininized self. For the most part, people I knew were astounded and I moved on. Perhaps it was my shaved legs which gave me away. Whatever the case, time flew by, and I started to cross dress more and more in the public's eye. Plus, at the same time, I slowly began to perfect my knowledge of fashion, makeup, and hair. I discovered the more I did, the more natural I felt and the more I wanted to do. In no time at all it seemed I was accomplishing tasks such as doing the family grocery shopping as a woman and it felt amazing.

Imagine my surprise when I then discovered I was going through another major gender transition. All of a sudden, I was losing my desire to just look like a woman and I more and more wanted to explore a path to transgender womanhood. Mainly because I was feeling alive and amazing when I did it. Now we all know how difficult a gender transition is for the average human being, and I was no different. I had very few natural feminine characteristics to work with and I had to struggle completely to survive in the life I wanted to live. Especially when I hit what I call the dark period of my life when I lost nearly everyone close to me to death. 

In order to bounce back, amazingly, I was able to rely on my strong inner feminine soul to survive at all. She helped me find my way. During the bounce back period of my life was the time I found a whole new set of women friends to instruct me on how to live my new life. Included in the trio of new friends, was my new wife Liz who I never expected to meet. At my advanced age of sixty plus, I would never find another person to be close to the rest of my life. Especially since I carried so much gender baggage with me. At the time, I still maintained one tentative foot in the male world, until Liz told me she did not see any male in me at all and what was I waiting for. Go ahead and fully transition. I was amazed and still am since it was over thirteen years ago when our relationship happened and is still going on strong today. 

The end result of watching the ball drop to welcome the scary year of 2025 was I have been so fortunate to have led an amazing life so far. Mainly because destiny has been on my side, and I have lived long enough to accept it.  

All Hands on Deck

 

Image from UnSplash

As I progressed farther along my long and difficult gender journey, there were many times where I wished I had company to aid my path.

Even though I often whine and cry concerning the lack of assistance novice cross dressers or transgender women have early on in their progression, the fact remains we need to work our way through it and do the best we can with our fashion and makeup. Until I began to see positive results, I am sure I looked like a clown in drag. Still, I was alone with my thoughts. I am old enough to remember with "Virginia Prince" and her Transvestia publication first came to my attention. It provided me with the first real look at others who shared the same interest in being femininized and looking like a girl. I was mesmerized with more than a few of the cross dressers I saw in the publication. I so badly wanted to be like them.

For years as I worked alone to look more realistic as a cross dresser, I still yearned for feminine help. I thought any cis woman could help me because of their years of practice and interaction with their peers. When I was engaged in college, the opportunity to be dressed from head to toe as a woman by another woman finally came my way. Somehow, I begged my fiancé to do it even though I don't remember now how I did it or was so persuasive. I went all the way by even renting a motel room for all the pre-prep work such as shaving my body I would have to do. 

Once I shaved and dressed, I was excited to undergo the long-awaited makeup process. Since she wore quite a lot of makeup, I was confident she could do a great job. It was finally time for all hands-on deck in my young cross-dressing life. Back in those days, mini skirts and dresses were in vogue so I brought one I found and purchased along with panty hose, heels, and a long blond wig and started the transformation process. To say I was excited would be an understatement. Time flew by as she finished my makeup, and I headed for the mirror. Instead of the beautiful blond I thought I was going to see, I was actually disappointed. I could not see much difference in her efforts from my own. Even still, I acted as if I was really impressed with her expertise when in fact, I was impressed with how much I had learned on my own over the years. 

It took me a long time working with makeup to learn each of us has a blank face to work with and we need to learn the best way to work with it. My fiancé was doing the best she could with the knowledge she learned from her own face, not mine. She was far from being a professional such as the help I finally received from a true makeup pro at a transvestite, transgender mixer I attended years later after I was discharged from the Army. He taught me lessons about my face I had never even considered such as which features to play down and which ones to build up. To this day, I owe him a huge vote of confidence and thanks.

It turned out the opposite happened with my fiancé. Due to knowing my deepest, darkest secret about being a cross dresser, she said I should use it to dodge the draft and stay out of the Vietnam war. There was no way I was going to do that, so we split up shortly before I was to leave for basic training. Actually, it was the best thing which has ever happened to me in my life. The pain it caused immediately would have been nothing like the suffering we would have gone through if we had stayed together.  

Looking back, at my life's work as a transgender woman, for the most part, it has been a solitary experience. Not having a female peer group to interact with and learn from was a problem to be sure but one I learned to work around. The end result was, I needed to be better than the next woman to make it. 

Expedition Transgender

 

Image courtesy JJ Hart

The half century journey I embarked on to finally come up as my true authentic self was certainly an expedition. 

As I always mention, my discovery began with going through my mom's underwear drawer and trying on nylons, bras and girdles I could still fit into before testosterone poisoning really set in. From there, I progressed into makeup and very slowly began to increase my craft. I did not really want to look like a clown in drag so I did the best I could. 

Life went by and so did my expedition. Sadly, for several reasons, I developed several coping mechanisms to mask my gender truth. I tried and tried to convince myself my desire to wear women's clothes and look feminine was just a harmless hobby and perhaps was just a phase in life I was going through. It took me years to realize the true phase I was going through was that I was a male at all. With sheer willpower, I managed to learn to play the male game fairly successfully and lived a life which shielded my feminine self from most all intrusions. I went into my dark lonely gender closet and slammed the door.

It took me years to have the courage to open my closet door and tentatively look around. When I did, my expedition took sudden and encouraging turns. The more I tested the public as a transgender woman, the more successful I was. I set out to sample as much as I could of a woman's lifestyle and discover my feelings on what would happen next. I tried going to gay and lesbian bars as well as big sports bars and found I could carve out a spot as a regular in a so-called straight venue. I also tried to go to various other places such as bookstores and other retail venues single women would go. In other words, I was obsessed with coming as close as I could on my expedition to seeing what a cis woman went through in her life. By doing so, I could make the final decision on where I wanted to go with my life, as a man or as a woman. 

As my expedition transgender progressed, I found myself in a face-to-face decision on beginning to take gender affirming hormones or not. Since my only real opposition to beginning the hormones had passed away, my ultimate path was clear, and I sought out a doctor for approval. He checked me out and determined I was healthy enough to begin HRT with minimum dosages of Estradiol and a testosterone blocker and my life changed forever. All the changes which occurred would fill another blog post themselves. Perhaps the biggest overall surprise was how quickly my body took to the new hormones. So fast, I needed to rethink how quickly I was going to have to change the timetable of when I ultimately wanted to finish my expedition and enter my own transgender womanhood.

I learned the fact of the matter was, I was always living a gender lie. I had refused to accept the fact I was always deeply feminine and was forced into a male lifestyle from some cruel twist of fate. All the time I thought I was a man attempting to be a woman was wrong. I was a woman attempting to be a man.

I wish I could have a portion of my life back to re-center my expedition and start all over again.  

 

Getting What you Want

 

Image from Aiden Craver
on UnSplash.

This is not really a Christmas post, even though in many ways, it fits in well with the season. 

As I was growing up, I vividly remember being asked what I wanted to be when I grew up into an adult. I also remember lying and saying something like a lawyer or doctor. Anything to make my parents happy without telling whoever asked, I really just wanted to be a girl when I grew up. An answer such as that would have landed me in all sorts of trouble.  

I progressed through life doing my best to navigate a very dark and bumpy gender road without much help from anyone except the occasional therapist. Through it all, for the longest time, getting what I wanted was a faraway dream. During my gender journey, I faced all sorts of problems such as my reoccurring issues dealing with my feminine appearance. Like so many of you, I needed to learn the fashion and makeup arts all by myself with no one to help. Back in those days, there were not the plethora of on-line makeup videos and special makeup stores to help a novice cross dresser along.

Then there were the up close and personal meetings I had with the impossibly feminine transsexual women I met. Interacting with them made me feel again how impossible my dream of becoming a full-time woman of any sort would be. However, it was about this time I began to take better care of myself, so I had a chance of becoming a better feminine version of myself. 

I dieted and lost nearly fifty pounds and began a regular skin routine which really helped with using less makeup and achieving better results. Suddenly, there was a light at the end of my presentation tunnel which was not the train. Maybe I could get what I wanted after all. At that point, I really became serious about exploring the world as a transgender woman. The rest as they say is history. When I did gather the courage to enter the world, I found I could survive. I discovered a great majority of the world did not care and a smaller percentage was just curious and amazingly enough, a smaller percentage yet respected me for living my truth. The bottom line was I survived and became better at life as a transgender woman.

When I did survive and relaxed, I saw my reality shining through. Maybe, just maybe, I could shed the shackles of my old male existence and live my gender dream. I could answer finally my own question of what I wanted to be when I grew up. A woman. To further the process along, I was able to begin gender affirming hormones which femininized me even further. My facial lines softened, my hair and breasts began to grow, and my emotions softened to the point where I could cry freely for the first time in my life. Through it all, my body was asking me what took so long to start HRT.

Looking back, getting what I wanted was the most difficult trip I had ever taken in my entire life. Pure perseverance and destiny helped me along to a full-time life away from my old unwanted male self, into a life I always wanted.   

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.

Outreach Lunch

 

Today is the Alzheimer's Association diversity council holiday luncheon.  

It will be interesting on several levels. The first level will be the near hour drive to get to the venue in a rainstorm. Of course, I put off getting gas in the car so I will have to stop in the rain to fill the car up with gas. Which will undoubtedly ruin all the time and effort I put into doing my makeup and hair this morning. One of the problems of being a woman.

The second level I will face is all the people I will be meeting for the first time in person. Since I joined the diversity council, all the meetings have been virtual, so I did not have to worry as much about my overall appearance. Resorting to a close shave and light makeup to get me by. This morning, I needed to be on point with my makeup and hair regardless of the weather, so I put more time and effort into my appearance. 

Plus, there will be more people at the luncheon since the Dayton, Ohio chapter is joining us for the holiday luncheon.  Since I have been received well by all the people in the Cincinnati chapter, I have no reason to believe the other new people will be any different. 

When we go around the table for any new news, I can even come up with my own. I can tell the experience of mine with the television reporter who supposedly wanted to interview me concerning LGBTQ elder care when in fact he kept steering the interview towards my feelings about the election. I will try to explain to the group why I turned him down and with it, a chance to publicize the work of the Alzheimer's diversity council. 

Overall, I hope I can catch a break with the heavy rain which is forecast and enjoy my lunch. Sometimes I struggle being social around strangers, so we will see.

In the meantime, you do not need to be in Cincinnati to volunteer your time to a local or regional Alzheimer's chapter.  If I am any kind of an example, you will be welcomed with open arms. Also, in my case, I am trying to pay forward the assistance my family received when my dad passed years ago from the very ugly disease.

If anything happens good or bad at the luncheon, I will write about it later. 

Tennis Anyone?

Image from Tony Luginsland
on UnSplash.

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

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

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

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

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

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

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

The Double Edged Gender Sword

Image from JJ Hart. Wife Liz on left.

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

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

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

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

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

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

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

Trans Girl at Black Friday

Woman Shopping on UnSplash.

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

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

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

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

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

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

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

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

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. 

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. 

Outreach the Easy Way

 

Out with my wife Liz
on left.

Last night, I took Liz and her son out to a steak house for her belated birthday dinner. She is a big fan of a good steak. 

To show you how popular the place is, we needed to wait for an hour for a table. There were not even any seats in the waiting area, so we had to wait outside on a solid metal seat. Fortunately,  the weather was unseasonably warm and dry so all we had to do was watch the other customers come and go. By doing so, I was able to notice the amount of fancy pickup trucks in the parking lot. A fancy pickup truck in my mind will forever tell me the driver is a fan of the new president I dearly dislike so I wondered if I would face any negative feedback from being transgender in the restaurant.

Once we finally made it into the venue, the pressure was on to see what everyone else thought of me. My fears proved to be unfounded. Even though the other people in the lobby had nothing else to do but to people watch, nobody zeroed in on me. I was essentially invisible to the world which is what I wanted. Men, women and children ignored me as they fidgeted, all waiting for a seat.

To be sure, it was not always this easy for me. I went through years learning the art of makeup and fashion I needed to transition out of a male world and into a feminine one. I was stared at the least and laughed at the worst when I went out to eat. All along I was a woman on the inside just waiting to get out. I was in my own version of gender heaven and hell. It all paid off when I have experiences such as last night but sadly I still have scars from unpleasant past experiences. 

By this time, you may be thinking I am a person with a huge trans ego problem. My second wife was fond of  telling me my femininized life was not all about me. She in most senses was not wrong, I was going all out to be the best cross dresser or novice transgender woman I could be and I needed to watch the room and other people around me to judge how I was doing. There simply was no room for anything else in my life on most days. 

It took me years to learn to relax and enjoy my new transgender womanhood as I was too busy still trying to read the people around me. Last night was one of those rare evenings I could relax mainly because I felt I looked nice, sounded confident and even felt physically better which all contributed to a fun evening. A good night of transgender outreach to all those pickup drivers who saw us portrayed as monsters during the previous election. As I look to the future while I process my past. 

What did I wear? My The Ohio State University sweatshirt, jeans and tennis shoes to blend in with all the other Ohio State fans in the venue wearing their fan gear. However, I did step up my hair and makeup with eye makeup, foundation and lipstick. So I wasn't a total plain jane. 

Whatever it took, I needed to blend in with the masses at the steakhouse and I did, they were not interested in me which was good. Outreach invisibility at it's finest.

If You can see it You Can be It

 

Image from Trans Ohio party JJ Hart.

Long ago, when I first glimpsed myself in the mirror as a feminine person, very soon I realized just seeing myself was not enough, I wanted to be the girl I was watching. 

In the classic if I had known then what I know now, I would have known then I was less of a cross dresser and more of a transgender woman. Way before the term transgender was ever used. Now more than ever before, it is time for us to blend in with the public at large as transgender women or trans men. We just have to be better and better.

Fortunately, I had years of preparation to be ready to face the world. Since I had plenty of testosterone poisoning to overcome, there was work to be done and I needed the courage to do it. Along the way, I viewed the whole process as stairsteps towards what I perceived as an impossible dream of transgender womanhood. Facing the world with confidence was my biggest problem. Every time I took a positive step forward when I went out in the world as a novice transgender woman, it seemed then I faced several steps back. When I was on point with my fashion and makeup, I lost it with my voice. Or vice versa on other days when I caught myself slipping back into my old male ways and walking like a linebacker. Adding to my problems was I was still trying to maintain a life stuck between the two main binary genders which made my existence even more difficult. I needed to consciously think all of the time which gender I was dealing with the world as. I was in.

Very slowly, I worked through this phase of my life and found women friends who I could learn from. I learned I could relax with them while at the same time learning how it was in woman only spaces. At the time, when I looked in the mirror, I was seeing it and being it which felt wonderful and so natural I knew I was in the right place. For the first time in my life, I thought my dream of leading a feminine life could be realized.  

Through it all, I still needed to work on my makeup and fashion skills to blend in with what my lesbian friends were wearing. It was a challenge because I needed to look as if I was not wearing any makeup at all when I was. I needed to work harder than the average woman to succeed in the world. By this time, I was used to it and worked hard to instill confidence in what I was doing with my gender goals since there was so much at stake. I was playing a high risk game with my life. Was the grass really greener on the other side of the gender border. 

I found out indeed the grass was greener but often not so easy to enjoy. I met more than a few women who did not want me in their world and did not hold back on their dislike for me. When they did, I needed to quickly pull the knife out of my back, smile and move on to friendlier situations. 

By this time, I was so close to seeing my dream goal of transgender womanhood, I pushed on even harder. I started gender affirming hormones with my doctor's approval. When I did, the changes came quickly and naturally as my body adapted to the new feminine hormones. Predictable changes such as hair and breast growth were quickly proceeded by inner changes with emotions as my life suddenly became softer. With my softer skin my facial changes were fairly dramatic and I knew then I could see it and be it.

As with any other long journey, you wonder was it worth the time and effort. With me the trip from the mirror into the world and beyond was just finding my true self. 

Reaching Out for Truth

 

Image from Jen Theodore
on UnSplash.

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

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

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

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

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

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

Fall Leaves

Image from Alisa Anton
on UnSplash. 

I write substantially how fall is my favorite season of the year. I love the cooler temperatures, wardrobe changes and how the trees change into their brilliant colors. All before the colors go away and drab winter sets in.

Long ago, I felt all the seasonal changes deep down to my inner soul. Of course as a novice transgender woman the wardrobe fashion changes were challenging and fun. I learned I needed to look ahead for the best clothing bargains if I was to be successful in locating all the fashion firsts in sizes that fit me. After a few seasonal changes, I began to feel so natural, I automatically felt the changes coming on. Fall was especially fun when it was time to go through all of my leggings, boots and sweaters to see what I would have to add or subtract to make it through another season.

Even though fashion changes were exciting and fun, other aspects of the season just brought about melancholy depression. I vividly remember the nights when I went out and just drove around in my car watching all the leaves blow around in the headlights. Here I was still stuck in a gender I did not want to have anything to do with and not seeing a way out. Very soon, the fun of fall would turn into the depression of winter for me. My final fall before leaving for Army basic training was especially bad because I knew for a fact I would not be able to do anything about my transgender desires for a very long three years of my life. It seemed so unfair my new life into transgender womanhood would have to be put on hold through no fault of my own. I was bitter. 

Little did I know, after waiting over two years out of three in the Army, karma would come back to help me. During my last year I learned of a Halloween party which was being planned by a hospital group which my friends and I were invited to. Immediately my mind jumped to the possibility of me dressing up as a woman and going. Of course the problem arose how was I going to do it because I did not want to go halfway. I wanted to be the sexiest dressed woman at the party. Fortunately, I had access to an apartment where I could finally shave my legs and put on makeup with a wig I managed to buy at a downtown Stuttgart, Germany shop where I was stationed. Through it all, I knew I was risking harassment or worse by my superiors in the Army if the word got out about my so called "costume" which may have been a little too good. But nothing ever happened.

In fact, because of the Halloween party, my life changed nearly full circle that fall. A couple of days after the party, when my closest friends gathered once again over potent, tasty German beer I blurted out the costume I wore was more than a casual fun idea I came up with on the spur of the moment. I was a transvestite as we were known back in those days and I enjoyed wearing women's clothes, makeup and wigs. I knew at the time, again I would be risking what was left of the time I had left in the Army if what I said found it's way into the wrong hands. It did not matter at the time as the first time I left my gender closet felt so good. So good, I tried to come out to my Mom who promptly slammed me back into my closet. 

All of this happened during the fall which still remains my favorite season of the year. As a  transgender woman, I appreciate the re-birth of spring but summer is too hot and winter is too long and drab. It's why fall leaves are so important to me.  

Finding your Happy Place as a Trans Girl

Image from Trans Outreach, JJ Hart

As I negotiated my way through the gender wilderness I was in, I needed to reach out at times to find moments of gender euphoria or happiness. 

As I have written about in the past, happiness was a learned trait which was difficult to come by in my family. Being good was not good enough, there was always time to be better. Little did I know, I was seeking to enter a world where being better than the average cis-woman was not going to cut it. Being better meant survival. 

As similar to most of you transgender women and/or cross dressers, I started out innocently enough as I raided my Mom's clothes and tried to admire myself in the mirror before my family came home. The whole process worked well for awhile until I grew restless and wanted to increasingly explore the world as my femininized self. Sadly, most all of this occurred when I approached puberty and all the unwanted male changes to my body began to happen. Very soon, I found wearing any of Mom's clothes was impossible as I gained unwanted hair, bulk and angles I hated but were stuck with. It was the infamous testosterone poisoning setting in which I battle to this day.

Rather than be unhappy, the mirror and my mind helped me to battle my way through severe bouts of gender dysphoria. I worked hard on acquiring the proper clothes and makeup I would need on a very limited budget. Of course with no guidance, I experienced many disasters on my journey before I settled in on an appearance which could get me by in the public's eye. I needed to disguise all my testosterone poisoning. Still, I persisted without much help and slowly learned the art of makeup which finally I did get some assistance with. At one of the cross dresser - transgender mixers I went to, I put my ego away and sought help from one of the professional makeup artists they had giving free advice. In language even I could understand, the guy doing my makeup guided me through a truly amazing transformation. Even I thought I looked so good I was happy with the results. 

Even still, the transformation was fleeting and all too soon, I needed to go back to my boring unwanted male life and the happiness I felt went with it. Leaving me in a state of depression. I did not realize having a feminine appearance was only the beginning and achieving any standard of looks went only to the upper levels of feminine achievement for me. Beauty was fleeting and very skin deep for me as I continued on my gender journey. I was told several times by my second wife I made a terrible woman and in no way was she talking about my appearance. She was right and it took me years to put my male ego behind me and learn what she truly meant. 

I also had a close transgender friend who told me one time I passed out of sheer willpower. Which I took as a backward compliment. Meaning I was going to engage the public and do my best to be happy even though I was not the most attractive woman in the room. When I did, I made a huge step forward towards becoming my authentic self. It was not until then did I begin to gain new friends and become happier. 

Sadly, my second wife passed away before she ever had the opportunity to meet the new improved me but I did have several friends who did. Their main comment was how much more happier I had become. I guess I never realized how much my gender issues had shown through to others in my male life. 

When I reached this point, I knew my family and upbringing was wrong. I could be happy in life and appreciate it. Along the way, I learned the truth that all the money and beauty in the world could not buy me happiness. I spent way too long living in the mirror to keep doing it. The friends and wife I made when I put my male self behind me proved happiness was not impossible for me.