Living in Your Own Prison

 

Image from Engin Akyurt
on UnSplash

When someone says living a life as a transgender woman or trans man is a choice I get a huge chuckle. 

I wish the people who think my life was a choice, needed to live a small time in my shoes and  then they could truly decide my life was never a choice. I was living in my gender prison. In many ways, I could describe my confines to a bigger version of what was called my personal closet. Either way, I was stuck in a very dark and isolated space where I was all alone. Especially in the pre-internet days when I was living.

When the internet came along with social media, I was able to locate a few others who were cross dressers or transgender women , which made life a little easier in my prison. My biggest problem then became hiding my new on-line contacts from my wife who was more tech savvy than I was. Let's just say I needed to learn the hard way when my wife found a discussion I was having with a person in nearby Indiana and I had to become much too comfortable with.

Looking back, I could call the few, brief times when I tried to purge my feminine wardrobe and be a full time man as being out of my prison on parole. The problem was deep down I knew what I was doing was wrong and the pressure would build to build a new feminine wardrobe and try again in front of the mirror. I could almost predict when I would go back to my gender prison. 

Yet another casualty of me serving time in my closet was one I always mention, my mental health. Since it was already fragile and I was going to therapy for help, I didn't need any extra problems to push me closer to the edge.  I was becoming a hot mess as I took more and more chances when I left the house as my novice transgender self and explored the world. The problem became, I was feeling more and more natural when I escaped my prison. Even still, the process was not easy and involved too much scary trial experiences when I first went out. 

The entire process became all I thought about and when I was in my my male mode I caught myself thinking too much of the next time I was going to be able to experience life as a transgender woman. Plus, at the least I was busy studying the mannerisms of all the cis-women around me. I was locked in to one thing only and it was being a woman myself. It was a good thing I had my therapist to talk out my exploding feelings about my gender. 

I guess the only frustrating part of trying to explain to the outside world what it means to be transgender is there was no choice. If I would have continued in my self destructive male ways, I would have killed myself and become yet another statistic. Fortunately, destiny had other ideas for me when I escaped my gender prison and started to live an authentic life as a trans woman. Similar to so many others in the transgender community I was a survivor and thrived when I was free to do so. 

Bad Gender Decisions

 

Image from unknown origin. 

I often wonder if during all the writings I do, as I  describe how I succeeded in living my dream as a transgender woman, do I emphasize the bad decisions I made. 

Needless to say, I made plenty of choices I wished I had back to try again. First of all, I suffered from the same problems nearly all novice cross dressers or transgender women go through. Unlike cis gender girls our age, we didn't have the peer pressure or knowledge to help us be girls or women. We were not invited to the sleepovers where the girls experimented with makeup and clothes and it showed. I equated the whole makeup process to painting model cars when I was growing up. It took lots of practice to get the basics right. In the meantime, as I learned, many times I made bad decisions and came out looking like a clown. This was especially true with the clothes I chose to try to wear. I tried way too long to force my male body into clothes designed for sexy teenaged girls and I paid the price when the mirror lied to me and I tried to go out in the public's eye. 

When I was laughed at in public, I knew my feminine life had to change for the better if I was ever going to be able to survive. I just could not keep coming home in tears after another night out making bad decisions. Certainly. the process was not improving my deepening gender dysphoria. In desperation I sought out help from one of the only known gender therapists in Ohio at the time which was a good decision. The bad decision came when I decided to not listen to what she told me. She told me there was nothing she or I could do concerning my deep seated desire to be a woman. I would have to learn to live with it. If I had not been so hard headed and stubborn, I would have taken her advice and prepared myself for a life as a transgender woman. 

Once I started to really explore the feminine world, I made plenty of bad decisions. The primary example was when I became comfortable in presenting in places such as clothing stores, book stores and malls, I would always challenge myself to do new activities as a trans woman. Activities where I had to face the public and communicate one on one with the world. By doing so, I knew sooner or later I was going to have to challenge myself and use the women's restroom. Nature was calling and I knew I needed to answer the call. 

I started the process innocently enough by using the women's room in one of the bookstores I went to on a regular basis. I would do my best to make sure the room was empty before I went in and took care of my business. I was fortunate in that I read about and knew quite a few basics women follow when they gather in the restroom. I also knew from my experience in the restaurant/bar business women were not always the pristine gender they are known to be but that is another story. As well the other basics I needed to learn such as looking other women in the eye, washing my hands and stopping to adjust my hair and makeup. 

For the most part the only bad decisions I ever made as far as rest room usage was concerned was which rest room venue I decided to use. On a typical night, I would plan to go to my regular venues  plus maybe try out a new place. By this time, I was becoming fairly secure in my presentation to the point I wanted to try to challenge myself. I decided to go to a borderline redneck venue, order a couple of beers and try to use the restroom before I left. Before I knew it, someone had called the police on me and I was told to leave. Which had to be the worst decision I ever made. From there I went back to my usual regular venues and everything was back to normal.

Normal for me was difficult to change. I was so use to pushing my boundaries as a novice transgender woman, I had a difficult time adjusting my life when I no longer had to push so hard. I was enjoying the fact I did not have to face making bad gender decisions to begin with.

Are You Really Someone Else as a Trans Person?

 

Image from Kevin Laminto 
on UnSplash

For the longest time, I considered the idea I was two separate people.

On one hand, I was living the male life I was entrenched in and on the other, I was attempting to carve out the precious time I needed to explore my cross dressing self in front of the mirror. Trying to live a life on the gender border between male and female as very difficult to say the least. When I was in male mode, I spent every spare moment wanting to cross dress again at the least and trying to imagine what living as a girl would be like the rest of the time. To make matters worse, I even dreamed of being a pretty girl when I was asleep. Then I had to wake up confused and bitter when I found out life really hadn't changed and I was still a male after all. I needed to go again and challenge an unwanted world. 

Through it all, I often wondered why me? It took years for me to embrace who I really was and know the answer. I was just me and it would have to be good enough. However, the family upbringing I went through made it so difficult. During my youth, I was taught nothing was good enough. When I brought home any "B's: in my studies, they were not good enough. Where were the expected "A's." The never good enough attitude carried with me into my cross dressing life, all the way to when I became a novice transgender woman. In other words, when I acquired a new dress, when its newness wore off, I always felt I could look better in another dress, It led me to being a thrift store shop-a -holic. I couldn't wait until I could take what I had set aside money wise from my wife and use what time I could set aside to locate the next great outfit. 

My problem became especially bad when I was able to afford shopping for new wigs. I went through what I called my clown era of wigs before I settled into one or two wigs I wore all the time. By doing so, I was able to finally begin to build myself as a stable transgender woman in the world. I was beginning to learn I was someone else and that person was not a guy. 

As I was doing all of this  and as I lived a new and exciting world as a trans woman, I found I was taking all the stress off my mental health. The new authentic me enabled me to feel more confident on the gender path I was taking. I was fortunate also to have had a good therapist at the time to help me talk my way through it with her. Since I had previously been diagnosed as being Bi-Polar, both of us were careful to keep my gender issues separate. Plus, no mention was ever made of me being two people. I set the idea aside as being yet another mistaken idea from my youth. It could have been my male self attempting yet another move to survive the onslaught of life changing ideas which threatened his very existence. 

My life today proves I was always only one person and that was my feminine side. It is so sad I needed to fight so long to feminize my entire life as a transgender woman. The only true person I needed to be.  

Teamwork makes the Dreamwork as a Trans Woman

Girls Night Out, I am on the bottom far left.

Similar to so many other cross dressers or novice transgender women I have heard from, they dream of enlisting a cis-woman to aid in their appearance.

I was included in having a similar fantasy. All the way to the point of begging my fiancé to completely dress me as a woman if I rented an out of the way motel room for privacy. Sadly, for me, she agreed and she did do her best to dress me as the woman of my dreams.  I say sadly for two reasons. The first being I did not see that much of an improvement over what I was able to do for myself since by that time I had practiced in the mirror myself for years. The second reason I say sadly came years later when I was facing being drafted into the military and being sent off to Vietnam. At the time she pressed me to tell the draft board I was gay to be deferred from going. Even though I didn't and don't have anything against the gay community, I knew I wasn't gay and wasn't going to lie to escape military service. The end result was she ended up breaking the engagement when I went off to the Army which I learned later was the best thing which could have happened in my life to that point.

As you can tell, I didn't have anyone to enable my teamwork work from any sort of a dream work. One of the problems I was having was working my way through exactly what my gender dream. I was still years away from facing my reality of being a transgender woman. So I suffered alone with my gender dysphoria before I was able to break out of my gender closet. It wasn't until much later when I discovered the beneficial beauty of having cis-woman friends who accepted the new transgender me for who I was. When I let it happen, my dreamwork began to flourish. 

Quickly I began to learn the world from the aspect of being an invited participant in girls' nights out. I was invited along to several different groups of women. All the way from married women to younger girls still in the dating pool. Neither mattered to me because I was learning so much about living a women's life with no men around. Even though when I went out with the younger group, I found how it was to be the decidedly older and less attractive woman in the group. Again, it didn't matter as I flattered and happy to be invited to begin with. 

This was an exciting time of my life when all of a sudden my dream of living a life of a fulltime transgender woman seemed to be so reachable. Being included and  embraced by the women I met was the difference. We went to birthday dinners together, went to parties with each other and of course used the rest room together, All of which turned into the ultimate bonding experience as a new trans woman.

Was I scared? Sure I was but the embraces I received within the group quickly put me at ease so I could enjoy myself and gain confidence in the new feminine person I was creating. It turned out I did not have much creating to do because once my feminine soul hit the world, she flourished. 

Even still, being in a women's world and experiencing their teamwork, did make the dream work happen for me. I was a better person for it once I left my gender dysphoria behind. My mental health improved as well as everything else in my life once I left my male self behind.

Opportunity Knocks

 

Civil War Cemetery image
from the Jessie Hart Archives
 

In my life I have found several really rare times where true opportunity actually knocked on my door. 

As I indicated, the situations were exceedingly rare and required split second decisions on how I was going to proceed. Possibly the first main one happened when I went with the "A" list trans women from the cross dresser - transgender mixer I was at in Cleveland. It was the night I gathered my courage, put on my big girl panties and was able to enjoy a professional makeover at the mixer. The result was I looked better than I ever had in my life and really wanted to claim my spot with the other impossibly feminine women in the room who were planning to continue the meeting with going to gay venues afterwards. At the second venue we went to, for the first time in my life as a woman I was approached by a good looking man who wanted to socialize. Since I was in a city I knew nothing about and with acquaintances who were about to call a taxi and leave, I decided to turn his advances down and leave. I often wonder what would have happened if I had stayed. What sort of opportunity if any, did I miss?

 Most likely, the second opportunity I did take advantage of was when suddenly I decided I had had enough of cross dressing and wanted to follow my gender instincts even further. It was the night I was determined to go out and blend in with a group of young professional women at an upscale bar/restaurant I had frequented several times as my male self. More than anything else, I wanted to see if I could blend in with the group as a transgender woman and enjoy myself. Perhaps what I remember most about the evening was how scared I was as I waited in the parking lot constantly checking my hair and makeup before I gathered the courage to go into the venue. As it turned out, opportunity did knock that night. I enjoyed myself after I could take a normal breath again and I knew my life as a casual cross dresser was gone forever. I needed new horizons to conquer as a novice transgender woman.

As I settled into attempting to find my way as a trans woman in the world, I tried to try different venues and situations to deal with. Some were successful, some were not. The ones which I can remember the most were the times I tested going to more or less red-neck country venues. I quickly discovered I wasn't welcome and moved on quickly but not before the cops were called on me a couple of times. No opportunity to succeed in those places for sure and I never went back.

Perhaps the biggest opportunity which came knocking at my door was when I had the chance to begin gender affirming hormones or HRT. At my age of sixty, I wanted to make sure I wasn't going to harm myself, so I took the proper precautions and sought out a doctor to prescribe the medications I had waited for so long. Fortunately for me my health proved not to be an issue and I was given minimum dosages to get me started. Seemingly, my body took to the hormones like I always should have been on them and new changes started almost immediately. In no time at all, I was moved up to a higher dosage and my new changes took over my body. So much so, I needed to move up my transition timetable when my hair started to take off and grow along with my softening skin and protruding breasts. 

Then, the most unexpected opportunity happened when I met my current wife Liz on line nearly fourteen years ago. At my age and transgender history, I was prepared to spend the rest of my life alone and especially never expected to ever be married again. Opportunity was telling me to never say never and here I am.

I have a very hard head however and many times opportunity had to knock loudly to get my attention. Often because I was stuck with life changing conditions where I could lose everything. I tried to fall back on my inner self and hope for the best and finally I let her lead me the right direction. 

Take Your Pleasure Seriously

 

Ohio River image from the
Jessie Hart archives. 

For a gender dysphoric person, the scale seems to be balanced against experiencing any gender euphoria.

 In my case, destiny allowed just enough gender euphoria for me to continue down my gender journey. As I questioned what I was doing, the "why" of it never really came into question. I just knew deep down I was on a process I could not control. It would control me. Deep down inside, regardless of any doubts I may have had dissolved when I felt so natural when I was dressed as a girl. In other words, I was home when I was away from my unwanted heavy male self. 

Still I persisted and tried to find my way in the male universe, I was taking my pleasure seriously when I was dressed head to toe as a woman. I found following one dream (feminine) didn't mean giving up on the other (masculine.) I often wonder, if there was any help available to me back in the pre-internet dark ages would I have had the courage to seek it out. One problem was back in those days we who existed with gender issues were still considered to be mentally ill. Which I knew I wasn't.

The gender unrest I lived through and with was to continue until much later in life. Nearly a half a century to be exact, I gave up any hope of ever returning to a male life and never looked back. Riding a wave of gender euphoria was something I had never experienced before. Living as my authentic self was amazing and even though my male self was still fighting to be recognized. He was to be denied and my life went full circle back to the earliest days of wondering what gender I really was.

By going full circle, I had a lot of ground to cover. In many ways, the world caught up with me. I was able to follow the progression of a term which would describe me and in a very small way enabled me to be a part of a transgender community. Along the way many things changed. Primarily in the terminology which began with what was transgender anyhow and went all the way to the LGBT label which has grown these days to include other letters which includes other communities. Including gender fluid people which on occasion, described how I perceived myself all those years ago. 

During my full circle journey, I learned to take my pleasure seriously. Different than most transgender women and one I don't necessarily recommend, I learned the so called "ropes" of being a single woman (trans or not) in alcohol serving venues. All of the sudden, I found myself in situations where I was the single woman. The positive side of taking my pleasure seriously was when I discovered a small community I could thrive in. The negative side came when I was approached by intoxicated men not in control of themselves. Early on, when I needed some sort of protection, I used my cell phone. Making a big show of acting as if I was talking to another person on the phone who was coming to join me and fill the empty seat beside me. Of course after I gained my small group of lesbian friends, I was nearly completely insulated from the world of men. Also my ideas of sexuality were determined for good. I had way more interaction with women than I ever had as a guy.

Along the way, my new found gender euphoria as I learned to live as a transgender woman began to put my unwanted male life behind me, I had managed to live through the down points in my life and come full circle into a new day. I don't know if the ups have ever equaled the downs but at the least I was never bored.  

Opening Transgender Doors

Image from Nathan Wright 
on UnSplash

What is the old saying, "When one door closes, another one opens." I think the saying is especially appropriate for transgender women or trans men.

Along the way, I have documented several substantial times when I slammed doors during my past and opened new doors. 

Probably the first time I closed a door was when I was going out with a certain set of party friends who ranged from cross dressers to transsexuals who were planning their genital realignment surgeries. I wasn't very interested so much in the cross dressers but on the other hand, I was very interested in the women who were going "all the way." I wondered if I could ever slam the door on the male life I had fought to live and open a new door into a feminine world. 

Luckily I was able to see different sides of the gender coin so to speak. One friend in particular was a firefighter in Columbus, Ohio who was gorgeous and near retirement. So she had the financial risk of a gender transition covered as did the other main transsexual woman I knew at the time. She also was gorgeous and had a very secure job as an electrical engineer. She was so good at living a woman's life, she regularly went on snow skiing trips, spending whole weeks as her authentic self. So, as you can tell, I had lofty role models to try to live up to. I knew they would be difficult to match up to as far as appearance and income plus neither one had a spouse to deal with. I loved my spouse very much and wasn't sure I was able to close the door on my relationship with her. 

Even still, I continued to observe and learn as well as set out to open my own transgender doors. It just took me longer than others to find a path of my own. I know all too many of our gender journey's are similar yet so far apart. It is difficult to leave the first door in our closet and find the other doors in the darkness. Once I was able to find the light and it wasn't the train at the end of the tunnel, I was able to progress quite nicely but not without trepidations. Of course I still had to deal with the usual problems transgender women and men have to deal with when they transition and close the big door. Sometimes closing the door is the easy part compared to opening the doors to different living situations with family, friends and finances. 

I think too many potential transgender folk believe the transition itself will cause the life problems to go away and they haven't thought enough about the all the situations they would have to face now when spouses and/or families want to leave them behind. Not to mention the prospect of losing long term employment and friends. All of the process led to opening very heavy doors and not having much of an idea what the future held. 

I was fortunate when I finally had the courage to open my final transgender doors and face the world. As I did, I could look back at all the times I was petrified to try a new life as a transgender woman. Every time I was so scared it seemed I made it OK which felt so natural and gave me confidence to move forward and look for new challenges. I don't think I ever forgot the two early gender role models I had in Columbus, Ohio so many years before but similar to my male life, I was able to carve out my new life as a fulltime transgender woman so different from theirs.

Even still, I have my doors to open as I face a challenging future with end of life issues. I am still paranoid concerning facing the problems associated with nursing care or assisted living. It will be quite the journey as I face the final door we all have to open and see what is on the other side.

Nonsense?

 

Recently I received this comment from Kendra referring to one of my political posts. Since I am a firm believer in  equal time, here is the comment:

"I am sorry you believe that nonsense about Trump. I am also TG, and I feel none of what you are speaking of. We conservatives are actually a loving caring group of people. Yes, many don't understand the lifestyle, but no one wants to hurt us. Please do not fear us."

Thanks for the comment and the first fact I would like to counter with is I do not fear conservatives and I have often thought of voting for Liz Cheney if she had ever made it on the ballot. To make it clear, I do not consider tRumpt to be a conservative. I consider him to be a threat to our country's security and the basic rights to all citizens. 

Now, let's add in tRumpt calling veterans (which I am one of) losers, bragging about reversing basic women's rights to their own bodies and increasing the national debt four times while he was in office while at the same time pushing through tax breaks for the very wealthy. Plus the biggest one of all, his threat to be a dictator from day one after trying to overthrow the government before (Jan 6th).

Kendra, what I really fear are the transgender citizens and allies who don't realize tRumpt and the paid off SCOTUS is coming after your basic rights. Perhaps you haven't heard of the 2025 blueprint. If you haven't I suggest you research it yourself. 

What I also fear is my hopes for my transgender grandchild's life in the future long after I am gone. At the least I want my grandchild to use the rest room of their choice which is being challenged now in my native Ohio by (yes) a conservative majority in the state legislature. I want them to know I tried my best in any small way to help the transgender and LGBTQ cause. 

I know sometimes I may sound as if I am some sort of a radical left leaning person but I value the counterpoints of having conservatives in the system and I used to have lively discussions when I was in the Army when I was the only once saying at the least Nixon was a crook. 

My deepest desire is tRumpt is never given a chance to advance his agenda against the the country in general and the transgender community in particular. It doesn't take someone in a paygrade higher than mine to recognize that after trans people are erased the bigots will come after the remainder of the gay and lesbian community. 

So Kendra, yes I deeply believe the "nonsense" about tRumpt. 

Un-Common Risks as a Trans Girl

Liz on left. Date Night. 

Most people undertake a risk or two as they make their way to the undertaker in the end. 

When you come right down to it, which person you chose to marry is a risk as well as which profession you choose. Transgender women and trans men seem to have an added layer of risk in their lives. Along the way as we pursue a gender transition, we have to make many difficult choices which aren't really choices at all. They are paths we have to follow or face devastating self harm to ourselves. Which results in extremely high suicide rates in the transgender community. 

When we are growing up in a world where our families often don't accept us, the entire process makes the risk factor even more important. I am so blessed to have a daughter who completely accepts and supports her transgender child and I am proud to have been a role model for my grandchild to follow but it wasn't easy. 

When it came to my marriages, seemingly destiny has led the way into several different areas of acceptance. Acceptance of course led to risks being taken. My first wife was very easy going and knew of my cross dressing desires before we were married and had our daughter who turned out to be my only child. My first wife accepted without question my desire to cross dress as a woman and venture out on Halloween adventures. I often thought if I came home from work one day and told her I was checking into a hospital for gender alignment surgery, she would have said that's fine, just be careful. As it turned out, I was not ready for that sort of surgical risk and would never be.

Then destiny threw me a curve ball with my second wife. The moment I saw her for the first time, I knew I wanted to be with her in the worst way. Even though she too knew I was a cross dresser, she still restored feelings I long ago had forgotten when I was ready to compete with another man for a woman. In order to win the competition I needed to divorce my first wife and move on to a totally different strong woman who knew somewhat of my gender issues. I say somewhat because back in those days I was just learning myself how deep my transgender feelings ran which were to cause strong problems in our twenty five year marriage later on after the newness wore off. From the start, I always thought she would be the one who would help me to break through in my cross dressing world and help me to be successful in my dreams. As it turned out, she wasn't that person and always drew the line if I suggested at all I wanted to go further into the transgender world. By the time she had passed away, our relationship had deteriorated into an ugly cat and mouse game of me taking risks and seeing what I could get away with.

Another main risk I took was with my job. Slowly but surely I had been promoted through the managerial ranks to a successful position as an executive general manager of a big popular casual restaurant chain. A position with a company I knew would not accept me transitioning into a transgender woman. In my haste to destroy myself anyhow, I began to go to my competition as a woman thinking no one would recognize me. Well, I was wrong and the roof began to fall in on me. It was tough but I denied all the rumors and kept on going.

By this time, my second wife's life was coming to an end and she suddenly without warning passed away from a massive heart attack. By this time I had purchased my own restaurant and was somewhat in control of my own financial destiny until a recession in the Rust Belt where I lived wiped out the population. I ended up losing my restaurant as well as my inheritance by taking a major risk and losing nearly everything I had. I finally was able to find me a fast food job to hold me over till I could take an early retirement from Social Security and sell vintage items my wife and I had collected over the years. Between the two I survived.

I then found myself in a period of wonderful gender discovery, when with the help of new women friends everyday seemed as if I was reborn. Specifically Kim and Liz helped me the most. Liz lived in nearby Cincinnati and we met on line. After corresponding by email  for months, I finally became brave enough to talk to her in person and our first date was at a drag show. That date was nearly twelve years ago and we are coming up on our second anniversary of marriage. Liz cemented her place with me when she told me she had never seen a man in me and why didn't I finish my transition into a feminine world with her.

Finally, after a half century of wondering and suffering over my gender dysphoria, someone else recognized my truth and wanted to accept it with me. My un-common risks were over. I accepted her advice, gave away my male clothes and never looked back.