Every Eye was on Me

JJ Hart

 When I was first entering the world as a novice cross dresser or transgender woman, I felt as if every eye was on me.

For the most part, most eyes were on me. Especially from other women. I vividly remember the times I was looked from head to toe by another woman. Slowly but surely, she was undressing every aspect of my fashion and making no secret of it. I thought at the time, I was just being introduced to the aspect of womanhood and to just get used to it.

At the same time, I was working on my overall femininized presentation, I was trying my best to mimic the way women move so I would not appear as a linebacker in drag. My adventures took me as far as trying to walk like a girl in large box stores late at night. I wonder now how many security cameras I made it on trying to perfect my walk. Through it all, I needed to be careful I was not walking the wrong way at the wrong time. Or for example, remember to not try to walk like a woman when I was working as a man. The entire process became more difficult the more I began to split down my time increasingly in favor of being a woman. I started with just cross dressing when I could a few days a week and ended with splitting my time four days a week in a feminine world versus three as a man. The whole process became even more complicated because I was still working my full-time job as a man. Especially when it came time to getting a new pair of glasses and I wanted to change over to feminine frames. 

The most difficult aspect of what I was attempting to do was the mental aspect of trying to juggle both main binary genders. I needed every moment to work on my transition and get used to all the nuances of it. A big portion of the process involved being looked at. At the least, no matter how well I applied my makeup, styled my hair and picked the right clothes for the occasion, I was still a big woman and would naturally attract attention. I attempted to conquer the size issue by losing weight. I responded by losing a significant amount of weight which helped in two ways. I could fit into better fitting women's clothes and at the same time look better when I went through another woman's inspection.

Of course, I was inspected by men too, but the inspection was much simpler, and I knew what it would involve. Women on the other hand, had more to look for since they had experience in the fine points of putting outfits together. At some point in their life, they had to put together everything from shoes to wardrobe to hair to put an outfit together. Since I needed to do it too, I knew what they were looking for and tried to plan for it. My accessories needed to match the rest of my hand-picked outfit to succeed. Even still, the times I went through helped me to prepare my future life as a transgender woman. 

If every eye was going to be on me, I was just going to have to adjust and do the best I could. If it was possible, I would try to thank all those women who looked me up and down. They taught me what I needed to do to succeed in my future. 

Real Life Impostors

JJ Hart at Key Largo.

 At various times in my life, I have suffered from impostor's syndrome when I was out with other women celebrating a girl's night out.

While I was overjoyed to be invited to the events and considered them to be a rite of passage to my transgender womanhood, I still could not shake my underlying feelings of doubt when I was allowed behind the gender curtain. 

As I went through the process, I began to wonder if all human beings go through a form of impostor syndrome in their lives. What I am trying to say is no woman is born a woman. They are socialized through life to achieve the status of women since they were born female. Men also go through the same process. It's the primary reason I had such a difficult time leaving my male past behind because in many ways I had made it to manhood which was miles away from just being another male. I needed to start all over again to travel to my gender goal of transgender womanhood. 

In the meantime, my confidence was building that I had as much right as the next woman to be at special functions. I had just arrived at the same point the other women did by using another path. I was aided also when I calmed down and began to contribute more to the group. I found I had more in common than I thought in this women's only space. Even though, I most certainly did not birth a child, I could bring up my own daughter and grandkids who I was so proud of. I just needed to flip the gender script to relieve myself of any possible impostor syndrome feelings. 

It wasn't just at the girl's nights out when being a gender impostor took a hold of me. Another prime example were the nights when I felt I was doing everything right. My fashion, hair and makeup all were on point and yet there I was wondering what I was doing there at all. I was devastated when I had come so far in my feminine presentation, just to have something else stand in my way. It took me awhile, but I worked my way through it all and put impostor syndrome in my rear-view mirror.

On the increasingly rare occasions when I encountered any resistance from the public, I finally came to the conclusion they were the true gender impostors. It was very clear to me why men left me alone as they were so insecure in their own sexuality. On the other hand, most cisgender women were more secure and not afraid to reach out to me. Especially interesting to me was the interaction I had with the lesbian community. Most of the lesbians I had a positive experience with had past encounters with men, so I was not so far from a person they would consider knowing. I learned quite early in my experiences in public, the various levels of the lesbian society. In fact, my first date with a man was with a very masculine lesbian on his way to becoming a full-fledged transgender man. Many times, the more masculine the lesbian, the more interest they showed in me. They were certainly not gender impostors.

Real life gender impostors are everywhere in this increasingly hostile world. We don't need insecure people in power using transgender women and trans men as crutches to increase their own power. 

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.  

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. 

Hitting the Transgender Wall

 

Image from Selin 
on UnSplash

There were so many times during my journey to finding my authentic self that I hit a wall or two or more. 

The easy walls came when I was younger and was trying to find makeup and wardrobe items to admire myself in the mirror. During that time and into the future, finances were a major set back. As much as I admired the pretty clothes the girls around me were wearing, I just did not have the money to afford any of them. There was no way I could go to my parents and ask for a pretty dress for my birthday or Christmas. Plus, I was stuck at a major point of my overall femininized image when it came to my hair. In those days, I was stuck with very short hair cuts such as burr or crew cuts and there was no way I could afford a wig. A major wall, to be sure as I think having the first wig I cherished did not come around until my college years in the late 1960's till the early 1970's when my military days took over. Of course I was against the wall again when my hair needed to be kept very short.

After I had served my time in the Army, I was able to secure the finances to afford a more update feminine wardrobe and my walls began to take on a more mental aspect with me. The more I was able to sneak out of the house and into the public, the more I knew I had little or no knowledge of where I wanted to go as a novice transgender woman. It seemed everything was being thrown at me at once and my mental health crumbled after I was hitting many walls at once. My male life was becoming more and more demanding as I became successful at my job and I discovered the more I explored the female world, the more I liked it. 

Even so, climbing the feminine walls were difficult. It seemed everytime I mastered one aspect of being a transgender woman such as walking, I would catch my heel in the crack of a sidewalk and ruin my whole day. As I continued along my bumpy gender path, I found mishaps with walking in heels were indeed minor in the scope of my transgender life. On the horizon loomed much more serious walls such as communication with the public and with women in particular. Overwhelmingly, men ignored me and women were curious about what I was doing in their world, I discovered quite quickly I was interacting with more women than I had ever done as a guy which was scary in many ways, including what would I say and how would I say it. 

I wondered what had I done when I was forced to actually talk the talk of the person I had become. I resorted to what had worked for me in the past as I had encountered tough trans walls to climb. I basically tried to shut my mouth and observe what was going around me. It worked to an extent until people (women) began to warm up to the new person I had become. I even was giving other women advice on how to understand their boyfriends or spouses. 

Anyway you cut it, I guess for me, gender affirming hormones created the last major wall for me to climb. At the time, I was doing my best to appear as a woman and communicate as one to the world. Beginning the hormones in many ways was a selfish move because I did it for myself. When I did, instead of more walls crashing down, they melted. HRT, when I was approved for it was a magic potent stimulant my body had been craving for years. Very quickly, I knew I had made the right move as I was able to tear the final walls down and make my way into fulltime transgender womanhood. 

Surely, I was bruised and battered by hitting all the transgender walls I needed to scale to live the life I wanted but I made it. When I look back on all the terrifying yet exciting steps I took to get to where I am mow, I wonder how I made it. First there was my appearance and battling testosterone poisoning then overcoming the problems of male behavior which also effected my life that all made for a rough journey. Surely there were too many walls to count.   

Just be Yourself

 

Image from Cory
on UnSplash

When you are a transgender woman or trans man, finding yourself can be a daunting task. 

Are you a boy or a girl is bad enough when you have to think about it but is even worse when you need to live your gender desires. Just being yourself becomes extra difficult when you are applying it to real life when you leave the mirror and take on the world. We all know that sometimes the world can be a very unforgiving place. Human beings are sharks and will sniff out the slightest hint of blood in the water. A bad place to be in when you are a novice transgender woman or cross dresser who is trying to make it as your authentic self and you are very insecure. 

At this point, many trans folk resort to fairly drastic measures to attempt to present well as the gender they are attempting to be. Fashion mistakes are made, just to name a few potential problems faced. It is difficult with no previous training or input from peers to catch up with the world and not appear as a clown. I do not want to remember how many thrift store items I returned because they did not fit me or flatter my male body style. For the longest time, I did not think I was ever going to find appropriate clothes I could be myself in. Not to mention the hair and makeup I was struggling with. Somehow I managed to fight through my inner gender biases and come up with fashion choices which the public could life with. When I did, I started to explore different venues such as community festivals and outdoor concerts to see if I could be myself.

Even though I was successful, I still fought internally my desire to be feminine. It took me decades to understand I was a woman cross dressing as a man and not the opposite which caused me such inner turmoil. 

Another problem I had when I was transitioning genders was staying in the present. When I was out and about as a novice femininized person, I was so busy being worried about every little thing, I could not enjoy being me. It took me years to actually accept the gender euphoria I felt when I had succeeded in presenting as an attractive woman in public. To battle my instincts, I did events which were more lengthy so I needed to live in the present longer. An example was the Joe Cocker outdoor concert I took myself to, just to see if I could and the NFL Monday night football game a lesbian friend took me to. There were no easy escapes to these events so I had to put my fear aside and try to be myself.

I am not a quick learner and my male self battled me for control of my life for a half a century before I finally gave in to my gender truth. When I did, my inner woman took charge for good and I was finally able to be myself. I could live in the present and not wait for the next time I could run and put on my feminine clothes and feel good about myself. I was wearing the clothes all the time and if or when I felt my old gender dysphoria creep in, I could solve the issue before it became too major.

It is easy to say all of us deserve the chance to be ourselves but it is extra important for a transgender person. Because, first we need to discover who our true inner person really is. Once you do, just being yourself is a much reachable goal to have.

Smiles Equal Confidence

 

Go Ahead and Smile from the
Jessie Hart Archives. 

Where ever I go in public, I try to lead with a smile to ultimately disarm any potential transphobic individuals. 

I have to remember also I look better when I soften my face which still has a tendency to go back to my old male scowl if I am not careful. A male scowl in my world always comes off as a bitchy look which I normally am never feeling. 

The whole process goes all the way back to the days when I was cross dressing my way to the front of the mirror. Since all the ups and downs which followed, I needed to learn to put my feminine image in motion if I was to succeed in following my transgender dreams. Since recently I have been getting out into the public's eye more and more again, I have needed to reinforce wearing a smile to boost my confidence as a senior trans woman. This morning was no different when I went with my wife Liz to her eye doctor visit. 

After I applied a light amount of makeup to go with my casual outfit, I thought for once I looked presentable for the world. I even tripped off my gender euphoria for a brief second. My euphoria lasted until I went through the door into the doctor's waiting room. For the briefest of time the two receptionists just stared at me and finally said how could they help me. Not the friendliest of greetings and I became worried about my presentation. Since I had quite a while to ponder the situation, I came up with the problem and it was all me.

I had forgotten the most important part of my presentation which is my smile. For the greatest majority of the public I face, a smile disarms them and allows me to communicate with them on a one on one basis. Plus when I am smiling, I am showing the confidence I need to enable the people in my world to be more friendly also. Most importantly, a smile is my best accessory when I use it properly. Not using it at all takes me back to the day when I was shopping for clothes and suddenly nearly ran into a girl child who was darting between the clothing racks. When she stopped and saw me, she exclaimed to her Mother "Look at the BIG woman." I had long enough to consider the kid at least called me a woman. Then she ruined the feeling by calling me a "BIG Mean woman." From then on I resolved to try to put a nicer look on my face and not scare the public with my bitchy look. 

After living a long unwanted life trying to exist in a male world, some habits are still hard to erase. Putting a smile on my face shouldn't be such a big deal but it is. So big, the whole process is as big as makeup, fashion and hair. Putting the whole image into motion is what counts for me to be truly successful as a full time transgender woman.  

Making it all Effortless

Image from the Jessie Hart Archives

When I decided to go all out and attempt to go public as a novice transgender woman, I found I had plenty to do before I go conquer the world as my authentic self. 

Reversing all I had learned to try to fit in to an unwanted male world proved very difficult to accomplish. Even more so when I learned I needed to make the gender transition seamless and effortless if I was to survive. The first problem I had to beat was getting myself out of my mirror. Just posing in my spare time cross dressed as a woman wasn't getting it anymore. Deep down, I knew I needed more if I was going to survive in my scary new world.

As I attempted to put my new feminine self into focus in the real world, I knew I needed to put away all my deeply ingrained male mechanisms. The prime example was doing away with my permanent leave me alone scowl on my face. I needed to replace it with a softer, kinder gentler look. I needed constant reassurance from myself to make it happen. Primarily because I didn't want anyone approaching me. I found out the hard way my methods were completely unfeminine and I was coming off as a bitch or worse yet, a miserable mean human being. I even was called a big mean woman in a clothing store one day by a little girl, so I knew I needed an immediate change.

The second most profound change I needed to make was how I moved as a transgender woman. Of course, it is no big secret women move differently than men and even though any added dimensions to my hips and butt were due to foam padding, I still had to practice overtime to accentuate my new figure. What I resorted to was trying to practice every second when I thought I was alone trying to walk like a woman. The problem I always encountered was everytime I thought I had put the total package together of makeup, hair and fashion and put the movement with them, I needed to go back to my male world and try to forget the whole thing. Through it all, I became very frustrated. I was having real problems making my whole feminine image effortless. 

Even still, I continued to make it a priority and finally began to see improvement in how I was perceived in the world as a transgender woman. I know, athletes call it "muscle memory" when they repeat a motion over and over again until they get it right and that is exactly what I needed to do. I started to look the public in the eye when I communicated with them and paid attention to what they were saying to me. By doing it, I was able to more precisely tell is someone was reacting negatively to me because I was trans and then what could I do next time to improve my presentation. 

Making it all effortless, did take a great amount of work but it was what I needed to do to accomplish my goal of leading a life as a transgender woman. Plus, I could not have done it without closely observing all of the women around me and the many ways they reacted to the world.    

Wigging Out

 Recently I wrote a post which detailed a few of my trials and tribulations I experienced with wigs before I was able to grow my own hair to a feminine length. Ironically, one of the first things I noticed was all of the sudden I had to somehow see the back of my head to check out my hair. No more easy out by using a wig head and stand. 

I received plenty of responses by readers who commented on their own wig experiences. Including Monica who currently is up to owning five wigs. I am sure at my height of "wigging out" I owned many more than that, so I understand the attraction. After all, wigs are a natural extension of our makeup and seemingly (at least for me) there was always another wig which would take me to the promised land and I would become the attractive feminine person I always wanted to be. Plus, I feel I was attempting to overcome the days of financial challenges when I couldn't afford much at all when it came to a hairpiece. 

It turns out, I wasn't alone when it came to being a struggling novice transgender woman on the search for the best possible hair. As has happened many times over the span of our lives, Connie and I share quite a similar history:

"At the age of 34, I was married with two young daughters. We’d just bought a house, and I was anxious to fix up the unfinished basement to make an office for my part-time business, as well as shelving for storing all of those seldomly used things, such as holiday decorations. I’d already put a door with a lock on it for my office, and then, late one night, I started organizing things on the shelves. When I got to the Halloween box, I took a peek inside. There it was: that black wig, along with all sorts of makeup. Now, I had worn that wig a few times on Halloween before, but it had been part of a monster-type of costume when I had. On this night, though, it brought back every memory of my feminine-self. I took the whole box, along with an old mirror that was in the basement, into my new office and locked the door behind me. Doing the best I could with what was available, I put the wig on my head and made up my face. Looking at myself in the mirror, I remember whispering, “You can do so much better than this.”

Photo Courtesy Connie Malone

Money was a little tight after just having had bought a house, but it was probably more on my mind to rebuild a feminine wardrobe and accessories as cheaply as possible out of my renewed guilt. My wife had a basket full of makeup that she’d given up on, so I could easily take what I needed from that. I ordered a dress, a pair of heels, and some undergarments from the Sears catalogue, which I could discreetly pick up at the store’s will call. A new wig, though, was more difficult to find without, I thought, outing myself. Somehow, I discovered that K-Mart sold wigs, so I got what I determined to be the best one that was available at the time. It was brown in color, just as my mother’s wigs were, and somewhat contemporary in style (as contemporary and stylish as one might expect to find at K-Mart, anyway). I remember shunning the blonde wig, at the time, as I thought it to be “overdoing it.” I bought that wig, along with a set of wrenches as an attempted cover, and thus began my return to the pursuit of womanhood."

Thanks for the comment! It's amazing to me how the slightest trigger object can lead us back into fond memories of our feminine pasts. Mine was a long blond wig I fell in love with and managed to buy for my then fiancé. She wouldn't wear it but of course I would. That hairpiece managed to stay with me for many years. Even surviving my time in the military and several ill fated "purges" I attempted when I resolved myself to never cross dress again. That really worked out! I haven't cross dressed as a man for nearly a decade. 

I can't make the point enough. I am so lucky to have been able to grow a full head of hair. Now I have to get back to a salon and let a hairdressing professional take care of it. Before it begins to appear as if I have been wigging out.  

"Hair" and Gone

My final visit to my "magician" has come and gone. As I previously wrote about here in Cyrsti's Condo, I am going to have to find another hair dresser to go to. Sadly my regular stylist retired. I found out during my final appointment she is suffering from carpal tunnel syndrome. Which causes pain in the hands.

As we said our goodbyes, I almost teared up (damn hormones). As you may recall, she, my stylist, is the one with a transgender son. As always, she worked her magic with my hair and I went upon my way.

My hair grows relatively fast, so I will be on the outlook for another stylist.

Now, onto another topic. fellow Blogger Mandy Sherman  wrote in with a comment about my trip to the auto repair shop:

"Good for you about going to the shop en femme. My mechanics know me, so doing that wouldn't work well...although I go in capris, a blouse, and flats when the weather is warm. Such fun!" 

Thanks Mandy! I thought it was a good time to explain a couple things about me for any of you new comers to the blog. First and foremost, I am a full time transgender woman. Using hormone replacement therapy very much blocked any return to being a male I ever had. These days, I would have to find a way to bind my breasts and tie my hair back to minimally even look male at all. The best I can hope for is to be androgynous...if I ever tried. 

I am fortunate though, because I never run into anyone I knew before my Mtf gender transition. They have to accept me for what I am. 

I like to say, I am a little slow...but not stupid. I knew totally when I entered into the feminine world, all of it wouldn't be a great time. That is why I heard so many times from my cis women friends when I transitioned, welcome to our world. 

As I sum this up, I need to say, I would never give up anything I have earned crossing the gender divide. 

To quote another familiar phrase, "What a long, strange trip it has been." And let me add, a wonderful one too!