Stuck in the Middle with Me

 

Image from Rene Ranisch 
On UnSplash

Once upon a time and probably more than once, my second wife told me my cross dressing existence wasn't all about me. 

We were usually fighting about my feminine existence when she came up with the same comment. The unfortunate truth was it was all about me. I had a singular desire to look better as a woman and I knew deep down the whole femininization process would not be accepted by my wife and if I was to succeed at all, I would have to do it myself. Since she was unable to help, it meant I was on my own to discover my own fashion, makeup etc. So, for the most part, we never saw eye to eye on anything when it came to my cross dressing. Over the years, it became obvious she didn't like my inner woman at all.

Even though I knew it was and had to be all about me, life went on and we were able to stay together for over twenty five years until her untimely death. Until the end, she resisted any idea of mine I would ever want to begin down the road to trying a transgender lifestyle by starting hormone replacement therapy. When she always stated she didn't sign up with me to be with another woman again I had to agree with her.

Since she did not accept me, I started to sneak around behind her back and found out it was possible I could follow my ultimate dream. In the world I was beginning to discover, I was able to begin to carve out a new life as a transgender woman. When I did I became stuck between the two binary genders. I was trying to live as my old male self a couple days of the week and my female self the remainder of the time. Of course my life became unbearable and I sustained dark days when it came to my mental health. Being stuck in the middle with myself was not a fun place to be. I would come to learn in her own way, my inner woman who was doing battle with my wife was just as strong willed. 

I quickly figured out my old male person was going to be the first person to go away when my wife passed. I'm sure in the next life, my wife wasn't surprised to see I quickly transitioned totally into a feminine world. She always said my dog would never miss her if anything ever happened and she could have added my inner woman would not have missed her either. To make matters worse with my overall mental health, my male self desperately missed her. Possibly knowing my wife was his last chance at maintaining any sort of life.

 Even though the times I was out exploring the world as a novice transgender woman on occasion I was terrified, I pushed on to experience the excitement of exploring a life I had always dreamed of. When I did, often I was surprised at the outcome. I never expected many of the results I had when my inner feminine self took over. Quite a few times I couldn't believe how easy and natural life turned out to be.

Being stuck in the middle with me turned out to be worth all the hassles I went through to arrive there. 

Gender Variables

Image from the Jessie Hart
Archives

When I was first looking at myself cross dressed in the mirror and when the mirror was lying to me, I felt as if I was well on the road to understanding what my life may be like if I ever had the courage to transition.

Of course I had no idea of the obstacles and challenges I would need to face as I attempted to live a life I had only dreamed of. There were plenty of times when I woke up in the morning following a vivid feminine dream wishing I was still the female I dreamed of being. The problem being was dreams don't ever equal reality. 

Reality meant I needed to learn all the gender variables I would have to learn the hard way if I was ever be able to follow my dream and live full time as a transgender woman. The first example I ran into was how I was dressing myself. I mistook trashy for sexy and tried to validate myself as a woman by trying to dress as a teenaged girl. Happily, I learned quite quickly I was dressing for the wrong gender. I was dressing how my male self thought I should, when in fact I should have been dressing to blend in with the other cis women around me. Cis women are women who were born female. 

Once I started to be able to blend in with and exist in the world as a visible feminine person, I found out again the hard way, how many gender variables I still needed to face head on. The main issue I always mention is how quickly I needed to learn to communicate in public. Unlike the mirror, these people really wanted to talk to me. At the time, I had barely given any thought of how my voice as a woman would even sound to another person. What I ended up doing was I tried to mimic the woman's voice who was talking to me. Men, for the most part, left me alone so I didn't have to worry about them. I think other women were just curious why I was trying to live in their world. Whatever the case, I needed a vocal or communication plan and quickly.

What I learned was women (as I already knew) operated on a totally different wave length than men. There were to be no more direct conversations which men do so well. I needed to learn the power of non verbal communication clues as well as the passive aggressive nature that women deal with. There were many times I ended up with scars on my back when I thought a smiling face meant support. All a part of dealing with the new gender variables I was learning.

As it turned out, I was learning new layers of the feminine gender I had only dreamed of living. Plus I was ultra confident I made all the discoveries I could when along came  even more challenges. At that point I developed the small group of women friends I needed to rise to the next level of gender variables I needed to face. Often I was terrified but determined to stay the course I was on. 

I learned once and for all what I had always known deep down. Women live a much more layered existence than men. Little did I know I would end up living all the gender variables and then some as I lived my life as a trans woman. 

A Night with the Boys

 

Image from the 
Jessie Hart Archives

Way back in the early days of going to what were known then as "transvestite" mixers, I ended up having a very special experience, In essence, I was still out with the boys, without my wife, it was just they were all dressed as women. 

The evening started innocently enough, with the usual sizing up of those cross dressers around us. A little bit of everyone was there from those cross dressers who were desperately trying to hold on to their masculine selves, all the way to the glamorous "A" listers who formed their own cliques. What I didn't know was during the evening, the group organizers were providing a few makeovers from professional makeup artists. 

I was intrigued by thinking I could be chosen for a makeover if I could fight through my fear to do it. Somehow I managed to land a makeover spot and then had to remove all the makeup I had spent so long to apply. Plus my ego thought I looked pretty good. I was to find out I was wrong.

There were several artists working, of both genders. It turned I was lucky and got one of the guys who were working diligently trying to do the impossible. In my case, he did do the impossible and I went through a magical transformation. To make matters better (or worse), along the way the make up guy was trying to explain all the techniques he was using to transform my face. I did my best to remember everything he told me and in the end run, he helped me to understand things such as the power of using a small amount of blush to highlight certain areas of my face. 

All too soon he finished his work and told me to put my wig back on. I could not believe the transformation and in my mind I was so excited  to show off my new look to the rest of the group. I did receive several compliments which cemented my desire to do more when the "A" listers went out on their own after the mixer was over. They normally went to some sort of a gay or lesbian venue to continue the party. To be able to go, I needed to be invited, so I began to seek out the one of the small group I knew and essentially invited myself along. I succeeded and managed to tag along for a night with the boys, all cross dressed as very attractive women. 

On this night, I was able to continue my own "Cinderella" experience when the group decided to call a taxi cab and go to an even smaller venue which to me looked as if it was a neighborhood tavern of some sort. It was somewhere in Cleveland, Ohio, which is all I remember now. This all happened during the pre-video game era and the place had two pinball machines. After I ordered a drink, I was able to find a couple quarters in my purse and started to play one of the games. Before long, a man approximately my age came up and wanted to play the same game with me so I had a decision to make. 

The rest of the group was wanting to leave and if I stayed, I would have to either call another cab or somehow depend upon this guy I had just met to get me back to the hotel. I made the split second decision to take the safe way out and leave with the "A" listers I came with. Before I did, to rub it in,  I made sure they knew I was approached by a guy and they weren't. 

From then on, I was more or less accepted by the group although I never had their privileged negative attitude which was so judgmental to others. However, from then on I was always searching for another "Cinderella" moment when I was able to spend a night with the boys without my wife. Partly because she normally always came along.

 Sadly, it never came again. 

Role Model

 

Image from Averie Woodard
on UnSplash

I have a close acquaintance who is taking a giant step forward in her transgender world.

She is stepping out of her comfort zone and will apply for a new job as her authentic feminine self. I was fortunate to be at one of her first attempts to explain why she was coming out of the closet which was tormenting her so much. I remember thinking at the time how far she had to go on her journey as I wished her the best.

During the following years, she has faced the same issues as other transgender women and trans men face, from marriage issues to kids and family decisions to decide upon. She has been very open on social media about her struggles. Including public pushback when her wife and her go out to eat. She lives very close to me and I know the venues she has had problems in and I understand why. In fact, I have had some problems also in one of the venues and we never went back.

Even with all of that, she pushed on and is now trying to take her transgender life to another level. Her current job is a truck driver which of course presented it's own level of challenge at every stop she made. She transitioned on the job and literally changed  her outward appearance overnight. I really respect the courage it took for her to take on her work world the way she did. Now the challenge she is seeking is to apply for another job (in the same industry) but in a whole different job as her feminine self as a logistical scheduler of sorts. 

If she gets this job or not, she is a true role model for others in the transgender community. To step out of her old gender comfort zone and sever ties with her old life as a man is remarkable.  It's a giant step forward. 

I am far from an expert in finding a job in todays' world. But from what I am reading in Cincinnati alone there are a few companies who are LGBTQ+ inclusive and offer employment possibilities to aid in a person's transition. It's good for both parties as the company can hire a good employee and the trans person is able to take a giant leap forward and support themselves financially in their new world. 

As I circle back to the person I know who is applying for the new job, I am sure this is just the beginning one way or another for her to step forward into a life she has always dreamed of. I hope she gets the job on the first try! 

Even though I am retired and don't have to face the work world as a transgender woman, I can still see a role model when I know one. 

The Good Fight

Image from Fred Moon 
on UnSplash

Often, our biggest enemy we face when we transition from one binary gender to another is ourselves. 

In the case of male to female gender transitioners the male ego never wants to give up his control. In my case it was a fight to the bitter end. A fight which nearly killed me. As along the way my old male self seized upon every means possible to preserve his existence and furthermore, he never fought fair. He felt he carried all the cards and only played any when he was pressed to do so. 

Through it all, what he never counted on was the inherent strength of my inner feminine self. Along the way he was ego driven to the point where he thought dressing as a transgender woman was simply a hobby he had to relieve the stresses of the world. When in reality, the opposite was true. She was letting him continue to express his masculine self while she bided her time and waited for her chance to shine in the world. 

As I continued to explore the world as my feminine self, it became clear to me who the winner of my gender struggle would be. Every step of the way in my brave new world felt so natural. Before I knew it my so called even split living life the best I could as a male and a female became more and more female and when I was spending life as a male, all I did was dream of what my next step would be as a woman. Where would I go and what would I do?

Of course the biggest problem I faced was my male self held the power cards such as family, friends and finances. The most powerful card he held was the influence he had with my wife of twenty five years who I desperately loved. She wanted nothing to do with my female and created the ultimate catfight between two women. In the meantime, in protest to having less and less influence in my life, my male self made my existence miserable, ruined my mental health and led me to try a suicide one night. He was prepared to risk my entire life just to maintain his. In addition, he pushed me into more and more alcohol abusive situations. Happily, I was able to end his influence when I transitioned before I seriously damaged my body. 

None of any of that mattered to my male self as he fought the good fight and slowly but surely was sliding down a very slippery gender slope. Deep down he knew every successful moment my novice transgender self experienced, the fewer chances he would have to claim his existence.  In typical male fashion, he moved ahead fighting change at every turn without thinking of the final outcome. In the process, he was making himself and everyone around him miserable. 

Finally he knew enough was enough and with the help of a few very close cis-women friends I took the leap and transitioned into a new life as a transgender woman. The slope I mentioned abruptly ended and I went into a gender free fall. Little did I know at the time how strong my inner female was and how much she appreciated finally being free and having the chance to run my life. 

It turned out she really knew how to fight the good fight since she had been fighting her entire life to live an authentic life. There are days, I wish I would have intervened in my gender fight earlier in life but as it stands now I have to live with what I did. 

Carry on Baggage

My wife Liz (right) and I with
Brutus Buckeye in the
Ohio State student union...

Those of you who have transitioned genders or those who are seriously considering crossing the gender border need to figure out how much baggage they will take along. If you are into sports at all (which I am) this time of year is fun to me because of all the huge football games being played.

So for me, the amount of baggage to consider was considerable. I wondered if my love of sports would have to take a back burner in my life. Because, back in those days, the choices were basically black and white with very little gray. If you remember, there were really only two groups of individuals you could identify with. Those were transvestites (or cross dressers) and the transsexuals who were headed for genital surgical intervention. Plus, after the realignment surgery, you were expected to exclude your past, move from your home and family and start your life all over.  No room for any baggage from your previous existence. 

Today fortunately is different. Mainly because cis-women of all sorts these days have or are living more diverse lives. The lines between male and female genders have been blurred. 

In my case I found out the easy way how much baggage I could bring with me. When I basically gave up on going to gay venues for any number of reasons such as being overall rejected as a drag queen or hating the music. I found I much preferred going back to the big sports bar venues I used to enjoy as a guy. Ironically, I found I was discriminated to less in the sports bars where I could order a large beer and watch my favorite sports team dressed as a transgender woman. Outside of a few notable exceptions I was able to establish myself as a regular by minding my own business and tipping well. I also found I could use all the help I could get as I researched if I could indeed add sports to my baggage as a trans woman.

On a higher level, I even found I could meet other women who were into sports and become friends I could interact with on a regular basis. Over the years I had a great time with them meeting and arguing sports with our tight little group of women.  

When I learned I could take on the biggest baggage carry on I could imagine, the rest of my life became so much easier. I could concentrate on learning from my women friends who happened to be lesbians all I could concerning my new life as a transgender woman. Especially valuable to me was the fact I was finally able to validate my gender dream. In other words, I didn't did a man to be seen with to validate me anymore. 

As I said, the ability to establish my new life and bring quite a bit of carry on baggage with me made my transition so much easier. Hopefully, you will have the chance to validate your new self also and make friends in the process. I would also be remiss if I didn't mention my wife Liz who took a chance on me when she saw my on line profile. She is the cis woman who told me a decade ago she didn't see any maleness in me and why didn't I throw the rest of my male life away and live full time as a trans woman. Her validation naturally was tremendous.

As with any carry on baggage, you naturally will find items you didn't really need but having the time to live a new life to find out what you can't live without, is important as you move on. 

Doing the Right Thing

 

Image from this Thanksgiving 
and the Jessie Hart Archives

At the most successful restaurant management job I ever had in my life, the company's main training point was to do the right thing.

Early in my life, I felt dressing as a girl or woman in any way was not doing the right thing. I suffered tons of guilt as I embarked along what turned out to be a long winding gender road. At certain roadblocks I found I needed to do the right thing again and again. Early examples came along when I needed to learn to dress my age and begin to blend in with the world. Often, doing the right thing for my inner feminine self came during the times I was soundly rejected by the public and came home in tears.

Perhaps the next step came around when I needed I had to finally leave my love affair with my mirror and begin to let the public be my mirror. It turned out it was one of the best moves I had made to that point in my journey. The whole process forced me to communicate with the world as a novice transgender woman and prove to myself the path I was on was the right one and it was leading me past the idea I had entertained for years I was simply a weekend, part-time cross dresser. Mainly because I felt so natural when I was living as a trans woman. 

Undoubtedly, I was doing the right thing with my life but there were so many challenges ahead. The more gender doors which opened, the more doors were still closed to me. A prime example was until I totally committed to living as a woman, I couldn't secure my permission to go behind closed gender doors and play in the girls sandbox.

Finally I arrived at the point where I needed to decide if I would subject myself to life changing hormone replacement therapy. After much soul searching and securing a doctor's approval, I decided to stay on the femininization road I was on and keep going. By doing so I knew I would be giving up what was left of my old male life. All male privileges I fought so hard for were gone and I was still searching for any female privileges which were still to come. The important point is I was still exploring my gender world to make sure I was still doing the right thing. After all, it was a major move. 

Perhaps the final chapter of if I really did the right thing won't happen until my final chapters are written, How will I be treated if or when I have to be admitted to an assisted living  situation. And finally will I be mis-gendered when I pass away. My only younger brother as already said he will never refer to me as my new legal name so that is that. 

In anyone's' life, doing the right thing is often the most difficult road a person can take. Especially when your life involves being transgender.

Thanksgiving and Beyond

Image from Kevin Dowling
on UnSplash

 As much as Thanksgiving was always a given as a time to meet up with family and eat a delicious feast.  Early on, the day was more enjoyable because one of my right wing nephews at that time did not want to start a political argument with me. 

Through it all, in the back of my mind, I knew something was wrong. In my own way, I was engaging in impostor syndrome. I wasn't the man I was portraying to be. Each year I used alcohol to dim the pain and move on the best I could. Even though I had very little control over Thanksgiving itself, there was a day I still thought eventually I may have some control over. The day in question was the Black Friday shopping event my second wife always insisted on going to. This all happened in the latter part of 2005.

Finally, I waited long enough or persisted long enough I was able to try out a Black Friday shopping experience on my own at a well known mall close to where I lived. My opportunity to cross another feminine experience off of my novice transgender woman check list came when I learned my wife (who worked in retail) had to work on Black Friday morning. Suddenly, since I didn't go in to my job until late in the afternoon, I had my chance to experience the shopping madness which was Black Friday as a woman.

When the day finally arrived and my wife left for work, my time to get dressed in my best sweater, skirt and comfortable shoes, added my blond wig, sensible make up and was ready to go. I was excited about finally having the chance to again live my dream. 

Once I arrived at the mall, predictably parking spots were at a premium but I finally found one. From there I had to gather my courage and enter the mall. Once I was in the shopping area, all my nerves faded away and I was able to concentrate on the relatively short time I had to fulfill a long term dream of mine. I wanted to experience the estrogen laden atmosphere of Black Friday.

All too soon, as I browsed a few of the stores for a gift or two, I found in particular no one paid me any attention at all. It was so crowded with mainly women, I was able to blend in with no problem. It was time for me to return to my boring unwanted male life and move on back to my impostor syndrome. I was learning I was never a guy cross dressing as a woman. I was a woman cross dressing as a guy.  

After I went into my work and became immersed in my job, at the least I was still mentally able to bask in the glow of being able to live out one of my big feminine dreams... to experience a Black Friday shopping experience as a transgender woman. As it turned out, my start to the holiday season was destined to grow and grow into one of the major holidays for me. Replacing even Halloween. Throughout the month of December, I will be writing more in depth about my times as I grew into a fulltime trans woman.

Thanksgiving Day and Covid

Just before Thanksgiving I was scheduled to receive my latest Covid vaccination update. I have to go to my local small Veteran's Administration clinic to get a shot in the arm.

We shall see if their amazing transition into an inclusive environment continues. Over the years they used to repeatedly refer to me as "Mr. Hart" or even "Sir". It seemed nothing more than a formal complaint from me could change the way I was treated.

Before I could file a complaint, however the whole place started to change. When I was called to go back for my appointment, I went from "Mr. Hart" to my legal feminine name which is on file with the VA. Plus, now the VA even has a place on their intake forms for transgender individuals.  I don't know what really happened but the change was night and day. I am not for sure but perhaps they changed out head administers for the clinic. I don't really care, I just appreciate the difference.

In addition, I hope I don't have any negative reactions to the vaccine because my wife Liz and I are scheduled to go to a family get together with my daughter's in laws. In addition to great food, I always enjoy the gender affirming experience as I am accepted by everyone. Especially from my transgender grand child. 

This time of the year is always bittersweet for me. In the past my deceased second wife really went all out. From feeding a big family on her own to extensive Christmas decorations, she did it all. Our big pre-civil war era house was ideal for her to serve a big dinner as well as putting up all the decorations. Remembering all of her work makes up the sad part of my bittersweet existence as I had to sell all of my wife's decorations.   

On the bright side (or sweet) part of the season all began when I began to do most all of my Christmas shopping cross dressed as a woman. As the holiday season approaches, I will go into more detail how the entire process worked for me. In the meantime I will tell you it all worked out very well. Maybe too well because I found shopping for others as my feminine self turned out to be a very enjoyable experience. 

I even went out shopping on the infamous "Black Friday" mall day surrounded by many many crazy shoppers who the majority of were women. I learned in a potentially stressful situation in a crowd of people, it is easier to disappear. In the meantime, learning to dress to blend and for comfort became of the distances involved when I went out.

There is much more to describing my experiences as I grew into being a successful transgender woman and how the season helped me. 

In the meantime, I hope you have some sort of family whom accepts you and you can enjoy your Thanksgiving.