The Elephant in the Room

Halloween Girls Night Out
Kathy on left. 

Many times in my life I have felt as if I was the elephant in the room and it had nothing to do with my physical size. I was a pretty good sized man at around six foot tall and two hundred fifty pounds which kept the bullies away when I was younger so I wasn't a huge man.

All my problems began to surface in my unwanted male life when I went to family events and felt strangely out of place. As my male self I was the elephant in the room, or you could refer to it as the impostor syndrome. All along I was a woman pretending to be a man. 

As life went by and I had more experience presenting in the world as my authentic feminine self, I felt even more out of place at family events such as my brother's house. It was the place we always gathered for big sporting events with him (my only sibling) and his two sons. All was good until I started my hormone replacement therapy and started to appear decidedly more androgynous. Even then, before my breast growth started to happen along with me being able to grow my hair long, I was able to wear a loose fitting shirt and tie my hair back to still remain vaguely male. My last attempt "purging" my feminine self came approximately six months before my second wife unexpectedly passed away from a massive heart attack. 

As I "purged" I vowed to grow a beard which would make it technically impossible to go out dressed as a transgender woman and/or cross dresser. It worked and I was extremely unhappy but my macho cooks at least responded in a positive way, saying I looked more "masculine." Not a compliment I wanted to hear, 

One of the first things I did after my wife's death was shave off my beard and resume attempting to learn more and more how to live a feminine life. When I did, I learned my size could be dealt with and it had nothing to do with being the elephant in the room. In fact, during a couple of my initial girls nights out, one woman acquaintance in the group was even bigger in size than I was. I finally figured out it wasn't so much how much bigger than most women I knew, it was so much more important how I carried myself, as well how well my fashion sense blended with the other cis-women around me.  

However, there were many times when I still did feel like the elephant in the room, when it came to be invited to other girls nights outs. One night in particular comes to mind when I accepted an invite to go with a group of servers and bartenders to party one night at another close by venue. Even though I was warmly accepted in the group, I couldn't shake the idea I just did not come up to their level of attractiveness, which included size. I finally concluded there was nothing I could do about it, relaxed and had a good time. For the most part, they were surrounded by guys trying to pick them up so I very much just faded into the background anyway. 

As with anything else in life, a person has to take the good with the bad. In the long run, my body has provided me with a successful base to operate from. I was big enough and barely athletic enough to keep the bullies away and not too big and masculine I could not squeeze myself into women's fashions. I guess you can say, my elephant ran enough interference for me to get by until I could establish myself as a transgender woman. 

I was the elephant in the room and felt it on many occasions as a impostor man and a trans woman. I lived to tell the tale...so far. 

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.

Stair Step Method

 

Image from Monica Sauro 
on UnSplash...

Every now and then I am asked how I managed to navigate a marriage, a male life and still transition to a feminine transgender life. It certainly was not easy.

I approached it this way, I took it one step at a time. I needed to prove to myself I could take on and conquer each challenge. Early on, the challenge simply meant looking the best I could as a woman. Then it all got so complicated. Each stair step required more and more work, especially when I needed to move fully out of my mirror and take on the world. 

Along the way, I became more goal orientated than I ever was in my male life. Unexpectedly at first  I was surprised when so many strangers wanted to interact with me. The strangers were mostly women who I think were mostly curious of why I wanted to enter their gender world. I needed to quickly add another step in my transition from one binary gender (male) to another (female) and start to communicate face to face with people I didn't know. I was traumatized since first I am very shy and second, here I was trying to modulate my voice to a feminine level and come up with feminine things to say. It was a huge step to take. 

To add into this step, I had to settle in on how I was going to look. No more going to the same venues with different wigs thinking I wouldn't be noticed. Of course I was and as I ascended to the next step there would be no more changing wigs and names when I was meeting the same strangers. As I said, all of this happened so fast, it was a blur to me looking back. 

Other giant steps I took were when I decided (finally) I was no longer a man trying to look like a woman (or cross dresser) and a man who deeply wanted to discard my life and live as my authentic feminine self. If I could climb more steps to get there. I needed to keep trying more and more venues to see where I would be accepted. Which included bathroom privileges. Most of the time I was successful except the notable times when people called the cops on me or I was banned by management. Nothing stopped me though and I just kept trying to find venues who valued my money. I always minded my own business and tipped well, so normally the employee's liked me.

Through all of this, I was desperately trying to negotiate a very serious twenty five year marriage. I guess you could say I was trying my best to build in hidden steps to save what was left of my relationship when all along my second wife hated the idea of me moving towards me living as a transgender woman. 

It wasn't until she passed away, did I take possibly the biggest stair step of all, being approved for and starting hormone replacement therapy or HRT. My body took to the new hormones so naturally, I wondered why I had waited so long. I just couldn't because of the woman I loved as well as being afraid to give up what was left of my male self.

Looking back at all the gender steps I took. I must have been a fairly good carpenter or gender contractor because I was able to arrive at my impossible goal of living full time as a transgender woman. Somehow, I managed to never fall and hurt myself along the way except the times when my ego was bruised which is the topic for another post.  

The Audacity of It

Image from the
Jessie Hart Archives

When you view the transgender community from the outside, I'm sure more than a few people, other wise known as transphobes, think we are nothing more than a group of people asking for audacious demands. 

I know with me, I often felt audacious in my demands on my wives as I transitioned towards being a transgender woman. After all, my wives were seemingly making all the sacrifices in the relationship as their man faded away. Through it all, yes I did feel guilty but at the same time, there was nothing I could do. Gender change was impossible as I journeyed along the path to eventually leaving my male self behind. Since deep down I knew there was nothing I could do about my gender issues (and or cross dressing), I knew my wives would eventually have to get over their misgivings and I would get my way. 

Also, I need to say both my first and second wives knew I was a cross dresser before we were married. I don't think either woman really cared until it came to me becoming more serious about living increasingly fulltime as a woman. My first wife was very easy going and never really pressured me before we broke up. My second wife was much more opinionated and did participate somewhat with my transgender self but never really liked my feminine self for whatever reason. From the beginning and all the way until she passed away, she drew the line at me starting hormone replacement therapy and taking another giant step along my gender path.

The audacity of it all came when she said she didn't sign up with me to be with another woman and she was right. There was nothing I could say. I will forever wonder if she ever would have come to get along with the woman I always was before she died. Of course I will never find out.

Then there are all the transgender haters or transphobes who have the ability to change our lives in the real world or as keyboard cowards (as I call them.) The audacity of all of them to intrude upon our lives speaks for itself. The only defense I can think of is, the transphobes can't and won't take the time to understand trans women or trans men. The unfortunate part of it is that just consider how long it takes most of us to understand our own gender issues. I know in my case, it was a real struggle to come to any understanding of what was going on in my life. 

The biggest audacity for me now is the fact I don't care what the world thinks of me. Especially transphobes and/or TERFS. Now I can face the world as my authentic feminine self with a tight knit group of family and friends around me. Plus I am a role model of sorts for my transgender grand-child. 

Being audacious all those years when I was struggling to learn the world as a transgender woman left me with so many scars. I learned the hard way to develop a thick skin and keep learning all the important lessons I needed to discover. The whole process was terrifying but all so satisfying.    

It's All a Dream

In an extension of yesterday's post, I decided to expand upon it a bit further. 

The idea I had was very simple. What if my whole life was nothing more than a dream? As with any dream, some are pleasant while others tend to be nightmarish. When I started my gender dreams, they were pleasant enough. Most of the dreams involved in me being very attractive and existing successfully in my dream feminine world. As it turned out, if that was all which was involved, life would have been so much easier.

Early on, I spent many hours shopping for just the right wardrobe additions so I could present better and better in the world as my dream woman. Due to financial considerations, thrift stores in particular were my friends. In fact, in most of them, I became so comfortable I started to use the changing rooms so I could try on sizes as well as styles. The whole process became so beneficial, I actually became very good at judging which styles would look good on me and even found sizes which fit me. Slowly but surely I began to transform my style into one that blended into the world from the former trashy fashion I thought looked good. My dream was telling me, all my validation as a transgender woman came from being admired by men when in fact it was other women who mattered.

Along the way, I was even able to learn to develop different wardrobe outfits for different occasions. Examples included if I was going to a lesbian bar, I would dress differently than if I was going to a summer downtown summer festival. My goal was to present as an "lipstick lesbian" in boots, jeans and blond wig in the bar but go for a much softer look with a light top, flowing slacks and dark wig when I went downtown. Even I was amazed on how fast my wardrobe had expanded so I could accomplish my goals of blending and enjoying my evenings. Especially the gay bar when a butch lesbian in a cowboy hat forced me into trying to sing karaoke with her. Something I was totally against because I was and am I totally not a good singer. To make a long story short, I managed to blurt out the only country song I knew and left...in a hurry. Her only comment I remembered hearing was my voice was lower than hers. At the least, the bartender got a laugh out of the whole affair since she knew the truth about me. 

Surprisingly to me, none of this was in my dreams. In fact, my dreams were fairly mundane when compared to how my life was turning out when I transitioned into a fulltime life as a transgender woman. No longer was I in essence playing with my gender. When I started hormone replacement therapy and finally came to the conclusion I was no longer a casual cross dresser, I knew I was no longer in a dream.

It took me years, to figure out my gender issues were much more than casual dreams. Plus, my gender was much more than a game I was playing with. These days, my sub conscious is catching up with the fact I transitioned a decade ago to living as a transwoman. I am dreaming increasingly of me as a woman.
 

Always on Stage

 

Photo from the Jessie
Hart Archives

Sadly Sunday night involved an emergency trip to the hospital because my wife Liz was having severe pains. 

You may recall, recently she went through two surgical procedures and was progressing smoothly...or we thought. The problem with going to the hospital the way we did, in the emergency situation, I did not have any chance to prepare or, no close shave or makeup of any kind. Not even a chance to tie my hair back. I had to go the way I was  and try to rely on my inherent androgyny I have lived with since I began hormone replacement therapy years ago. As it turned out, no one on the emergency room staff seemed to care since I imagine they have seen it all.

More important of course was my wife Liz's condition which was initially diagnosed  as a bowel blockage. Fortunately, after her doctor saw her, he thought he could go forward with no further surgery but she would have to stay in the hospital on a special diet. What a relief!

The whole process meant I needed to spend the day with her yesterday at the hospital with Liz. This time at least, I got the chance to prepare. I shaved, put on some makeup and went out into the world to battle traffic to go to the hospital. Of course, during the day, I needed restrooms to use to get rid of all the coffee I drink. Most everyone was really nice except the usual two people in a group who were not. 

As I walked past a certain group in particular asking for directions to the rest rooms I was glared at by two women in particular. Since I had to go I ignored them and the fact the rest of the group's gossip had gone silent. Since it was shift change, I had to go right past the group on the way back. This time I was struggling because I can only walk so far anymore without my back killing me. So I was walking hunched over as I was in pain. Hard to present as good as possible when it is a struggle to even walk. But I had no choice I had to make it.

Make it I did, and the women who glared at me, I managed to glare right back at. After all, since I have been out and about as long as I have I am used to always being on stage as a transgender woman. Men notice me and more importantly, women do to. Most of the time, I don't have any problems at all. I mind my own business and the world minds its business. 

Happily, Liz is going to be released today so I need to go back and get her from the hospital. Once again I will get ready the way I did yesterday and face the world with a smile on my face.

Gender Pilgrimage

 

Gender Pilgrim Troye Sivan

At the age of seventy four I often look back at my life and wonder how I was able to navigate the ups and downs of a gender pilgrimage. 

The way I have been able to separate my path is to roughly divide it into three segments which over simplifies the process but at the same time, makes it easier for my noggin to grasp. 

The first and most foggy time of my gender life was my early childhood. I don't remember exactly when I had a concrete idea of wanting to be a girl. I finally came to the conclusion it was around the age of ten. It was about this time when I started to explore the delights of feminine clothing from my Mom's wardrobe. From then on I started to save my allowance money as well the meager funds I earned from delivering newspapers to the rural customers we lived around. I had a powerful motivation to earn my own money and purchase makeup or clothes depending on what I could afford. 

The whole process set me firmly up for a nearly half century of cross dressing. As you can guess I had plenty of time to try different things while I experimented more and more deeply with being a woman and leaving my male life and privileges behind. I write often how I went about meeting other transvestites for the first time all the way to being approached by men. I was on cloud nine for weeks following an adventure I had after being made over by a professional at a cross dresser mixer I went to. Afterwards when I tagged along with the group I called the "A" listers, in a bar we ended up at, I was the only one approached by a guy who wanted me to stay and have a drink with him. The entire evening validated my desire to be a woman more often and at the same time made me hell to live with.

Sadly, I was destined to live this way for years, twenty five to be exact as I punished my wife for how I felt. I drank too much and tried to outrun my gender problems by changing jobs and moving to different states such as New York from our native Ohio. Instead of making my pilgrimage easier, I was attempting to make it ever harder. It almost killed me in the process as my mental health declined. The ripping and tearing of living between the two primary binary genders was just too much. I had to decide which way to go and made the choice to live in the future as a transgender woman. The problem was I was in my early sixties when I decided to leave my cross dresser phase and begin HRT or hormone replacement therapy. 

Of course now I am in the third phase of my gender pilgrimage and feel so relieved to having left all the turmoil of my male life behind. I know I did not make the wrong choice because I feel so natural with my life now. Out of an extreme level of caution, I certainly did well but on the other hand, I don't regret the male life I was able to live. Among other things, he gave me a wonderful accepting daughter and helped open the door to a relationship which led to a marriage to my wife Liz. 

I look at it this way, I was fortunate to have earned a dual gender citizenship by living on both sides of the border. An often long and difficult pilgrimage made it all possible.    

First Impressions

 

Picnic Photo, Liz on Right

Following up on my Halloween post from yesterday, I began to think of all the first impressions I noticed when I first went out in public as my cross dressed feminine self.

My biggest takeaway from the experiences came when I was interacting with men I knew. Nearly immediately I felt a rejection as if I had been excluded from the male club. Later in life, I would figure out I was just experiencing a loss of my male privileges. The better I presented as a trans woman, the quicker my male life went away. When I did, I learned I needed to live my public life with a perceived loss of intelligence and personal security among other things. I just didn't realize in those early days of public interaction exactly what I was experiencing. 

Along the way I also learned how the power of first impressions changes between the binary genders. Men seemed to concentrate on sizing other men up as more or less another threat while women were more accepting. To this day, I need to adjust to smiling first when I meet another woman and not to walk around with what is left of my old male scowl on my face. The problem I have is pre-judging the reaction someone else is going to have to me. You would think by now I would not be so affected by my thoughts anymore but I am. Most likely my thoughts still come from when I first started meeting up with the public. Halloween or not.

First impressions also involve how much confidence you have in yourself. When you can summon the courage to know without a doubt you are in the right place at the right time leads others to believe you are too. In her own way, my wife Liz encourages me to step forward as a confident transgender woman when we are interacting with the public in places such as restaurants. Even so, confidence in public can be a very fragile thing as I found out very early. Even when I was going out under the cover of having a Halloween "costume." 

The more parties I went to, the better I became at refining my outfits. I wanted to try my best to be mistaken for a genetic or cis-woman and not myself. The good news was it actually worked on occasion and the bad news was I needed to wait another year before I could build on my experiences and discover if I could really be able to ever live out in the world as a trans woman. Spoiler alert, I could but the process was to be a very difficult one for me. 

The first problem I had was figuring out which wardrobe I could choose to hide my testosterone poisoned male body. I started the process by losing nearly fifty pounds and finished by undertaking HRT or hormone replacement therapy. When I did, more and more I was pushed out of my old male comfort zone and into a new and sometimes terrifying feminine world. I had to learn all over again the power of first impressions and how to deal with people. 

For the most part, my life experiences now have been positive ones. The problem people I run into often have a negative world of their own which has nothing at all to do with me. I am merely invading their space. 

It is the best I can do!  

Coming Out Day

 

Image from Alexander Grey
on UnSplash

Recently I know I missed "Coming Out Day" which I think was actually on October 11th. 

My excuse is I have been so busy with medical appointments between my wife Liz and I, I barely had a chance to write a post at all. Today, following a very early morning trip to Liz's hospital for pre surgery instructions, I had a chance to sit down, do a little research and write concerning the when's and how's of my actual coming out.

Following a bit of quick math, I determined I actually decided to shed what was left of my old male self and come out in the year 2010. Up to that point, I was still attempting to recover from the loss of my second wife who passed very unexpectedly in 2007 from a massive heart attack. In reality, she was the only major hold back to me coming out in the world as transgender excepting what would I do for employment. I knew for sure the company I worked for would not accept me as a trans woman so I needed some way to support myself. Since I was already in my early sixties, I researched how much I could make if I retired early on Social Security and determined I could make a living by selling off all the vintage collectables my wife and I had accumulated over the years. 

I ended up selling enough to even pay off the back taxes I owed on my house before the bank came after it when my loan became due. I moved in with Liz and let the house go which is something I should have done years before. 

I remember vividly the night I decided once and for all to turn my back on my old male self and live full time as a transgender woman. Primarily, I was exhausted from all the gender tension I was putting myself through. Plus I had started hormone replacement therapy and was rapidly approaching the point when I was at the least, very androgynous. I had put myself in a gender corner I couldn't get out of and deep down didn't want to. As I stared into the drink I was enjoying, I finally said enough was enough and why did I have to live the way I was living. I was dividing my time between the two primary binary genders and I wouldn't wish the ripping and tearing I was experiencing on my worst enemy. It became so bad, I needed to consciously consider which gender I was going to live as when I awakened in the morning. 

As you can tell, I have been out and living as my chosen feminine self for many years now. As much as I wish I could, I can't take all the credit for shedding my old male self and never looking back. I mention often the small circle of women (cis or genetic) who helped me along my transition path. It turned out I was making the whole process much more difficult than it had to be. It was Liz's final push which sent me down the slippery slope to a new life when she told me she had never seen any male in me at all and why didn't I just transition and get it over with.

I suppose somewhere along the line I should have been keeping track of my coming out anniversaries but life always seemed to get into the way and the reality of the situation of living my dream of living as a transgender woman was too much. 

The old saying is true, time fly's when you are having fun.   

Gender Walls

 

Image from Marcus Loke
on UnSplash

One of the reasons I waited so long to transition into a fulltime feminine world was when I tried to escape the walls which were forever threatening to close in around me.

Little did I know, each successful move I made came back to haunt me. Ironically, success just showed me perhaps I could live my dream as a transgender woman. Before I arrived at my final conclusion, I needed to seemingly transition more and more on my gender journey. My prime example has always been the time I decided I needed to change my mind set when I went out into the world cross dressed as a woman. Somehow it occurred to me I needed to reverse my thinking and decide I was going out as my authentic self  and all this time in my life I had been crossdressing not as a woman but as a man. When I realized my gender truth, I began to feel increasingly uncomfortable in the male world I worked my entire life to be successful in.

Very quickly when I went down this new path, deep down I knew I could never go back. I was suddenly sliding down a very slippery slope to a new life. A life I felt very natural and excited to be a part of. I had no idea if the outside world perceived me as being any different and I may have just been playing with semantics but as I said, the feelings were much different for me. I had crossed the line in my mind from being a cross dresser all the way to being a transgender woman. The first night I tried to change and was successful was when I went all out to dress to blend in with a group of professional women who always gathered after work at a nearby "Fridays" venue for an after work drink. Even though I was scared to death, I was able to relax and enjoy myself to the best of my ability. The best part was, no one gave me a second look. The bartenders were nice to me and I knew I was changing forever. 

Following all of the excitement and gender euphoria, ironically the walls began to close in on me again. What would I do with all my new found freedom to cross the gender border. I still had a wife I loved of twenty-five years, friends and family plus a very good job to consider losing. The pressure was intense. With the pressure I began to do all the wrong things. Primarily when I began to emotionally cheat on my wife by going out as my feminine self as much as I could. Of course, I was caught on numerous occasions which led us into massive relationship straining fights. While I never cheated on her physically, the emotional cheating was bad enough to put extra strain on me which I didn't need. All the pressure eventually led me to another self harm (suicide) attempt and my wife finally telling me why I wasn't man enough to be a woman. She passed away before she was able to see how prophetic her words finally became.

The end result of all her criticism became, I re-committed myself  to learning more and more what my life would mean to me if I took the final steps to living as a fulltime transgender woman. My steps included being cleared by doctors to begin HRT or hormone replacement therapy. At that point I knew there could never be any turning back as eventually I changed my legal name and settled into a new life with my wife Liz. 

Of course my final wall to overcome will be if and when I need to face what will happen to me when I have to go into assisted living or face being mis-gendered by part of my family when I die. It seems there are always walls to face when you are transgender. 

Skirting the Issue

Image from Vladimir 
Yelizarov on 
UnSplash

Many years ago, I ran into the sting of being criticized for not wearing a skirt or a dress when I attended my first transvestite mixers. 

Many times I wore a nice pair of women's slacks long with foam hip pads to give me a slimming feminine appearance. Needless to say, it did not take me long to notice I was the only one not wearing a skirt or a dress to the mixer. Plus it did not take long for someone to mention to me why I would choose to dress the way I was. If I wanted to wear pants, I should have just come to the party as my male self. While my answer should have been why do not you mind your own business, instead I said something to the effect of I didn't need a dress to express my inner self.

Years later and armed with much more gender knowledge I knew I was correct on how I answered the person in question. The reason was, except for a brief love of denim mini skirts, I mainly never lost my fondness for wearing women's jeans and/or leggings. Personally, I found pants to be more comfortable as I blended in better with the close circle of cis-women friends I had bonded with. I guess I was fortunate also when women as a whole where I lived began to wear dresses and skirts less and less when they went out. During our recent visit I wrote about to our favorite restaurant which is huge in size, I never saw another woman in a skirt or dress. 

I will say, being a transgender woman who lives fulltime in a woman's world, I still value the flexibility to dress how I want. During the summer month's, if I wanted to wear one of my long and silky maxi dresses, I would. The whole process is part of female privilege and is what I signed up for. If I was getting bored with the same old drab male fashions, I could change my look up anytime I wanted. So skirting the issue was just another benefit. 

Another factor in say wearing leggings is they are warmer in the fall and winter months and benefit the changes hormone replacement therapy has had on my body. One of the first changes I felt under the new hormones was I was much more apt to feel the cool. No longer did I feel the women I felt were making up being cold all the time, were faking it. Along with them, suddenly I was cold also. Ironically, one of the last changes coming along would help me in my decision to acquire and wear leggings from my wardrobe. Slowly but surely after many years on HRT I started to develop my own hips. Leggings helped me to finally accentuate the fact I had a feminine body, not the testosterone damaged one I had to live with for so many years. 

These days, with fall finally setting in, I love my cozy sweaters and leggings. I paid my dues to blend into society and am happy to skirt the issue.  

The Ship has Sailed

Image from Sebastian Bjune
on UnSplash

Very early in life, I learned being a male in any way was going to be a struggle.

In response I went through all the necessary contortions I could find to seek approval in a gender world I wanted no part of. Ironically I found I needed to be proficient as possible at being a male or be bullied. Even though, deep down, I knew I had missed my male ship all together, I kept on trying. I did my best to succeed in all the male-centric activities I tried. Even though I was a dismal failure at playing sports, I tried my best to play football and baseball through high school. It was my attempt at jumping aboard what was left of my male ship before it sailed totally out of sight over some sort of a distant horizon. Through it all, women still remained a mystery to me. As I wrote yesterday, I didn't have my first date with a girl until halfway through my junior year of high school. Deep down I felt girls had all the benefits of life because they could sit back in their pretty clothes and wait to be asked out.

I on the other hand, had to summon all of my courage to ask a girl out, which again, I was a dismal failure at. My first dates with girls were always set up by friends who I thought felt sorry for me. I never understood until much later in life the grass was not always greener on the feminine side of the gender border when my spouses explained to me the torment they felt as they waited to be asked out. 

As it turned out, my gender ship had already sailed no matter what I did. Even though I tried my best to lead a successful male life, I was always haunted and  pushed along by the fact I was always supposed to be feminine or any label you wanted to place on me. There were many such as cross dresser or  transvestite all the way to transsexual and finally transgender. None of them really mattered as I desperately searched for my gender truth. Finally, all the stress and tension my gender dysphoria caused me led me to a very serious suicide attempt. 

After taking all the pills and not dying, I returned to my old male life with a new purpose. I knew my masculine existence I worked so hard to maintain couldn't continue. The ship had sailed and if I was ever going to have a chance at living a meaningful life, it had to be as a transgender woman.

When I did come to my gender conclusion, I never looked back. I started my life all over again in a woman's world by beginning hormone replacement therapy or HRT. At that point I never did miss my old male ship at all. It was as if a huge weight had been lifted from my shoulders and I was allowed to live again. As I was given a second chance at life, I most certainly did not want to destroy it and I set out to become the best person I knew how to be. 

It turned out I wasn't alone in starting over. My inner feminine self was waiting for my male ship to sail also and lend a hand. She did a great job because she waited so long.to have her way. It was good because I needed all the help I could get. 

Success Equals Confidence

 

Image from the
Jessie Hart Archives

As with anything else in life, when you are successful you want to try harder to replicate your success.  

An example happened way back in the day when I played with friends on a local softball team. One game we were behind in the last inning by one run when our team had the last at bat. To make a long story short, my best friend and I came up with back to back home runs to win the game. For several days, months and even years, we had bragging rights because of the back to back home runs. While I was never a good hitter, at the least my brief success helped me to forget how much I wanted to be sitting with the girlfriends and wives who were watching from the grandstands and concentrate on doing better when I batted.

While I was never able to achieve the success I experienced that night, I did other times under different circumstances. When I reached a point when I began to explore the world as a cross dresser or transvestite, I had a very difficult time with my appearance. I knew I wasn't in any sort of way a "natural" and needed to work very hard for any success I had when I left the mirror and ventured out. Many times I was stared at and even laughed at behind my back. Even with all of the negative feedback, I was able to have enough positive filter it's way in to keep going. Whatever success I found equaled substantial confidence. 

I discovered there were feminine privileges such as when I went Christmas shopping for my second wife one night at an Oak furniture store in Columbus, Ohio. I wore my nice black pantsuit. sensible makeup and blond wig. Then I discovered the perfect gift, a Oak bookcase but wondered how I would ever load it into the back of my SUV.. When I gathered my courage to go to the sales counter and pay, I was amazed to see two young men waiting to load my purchase for me. I thanked them profusely and was on my way back home. I knew my male self wouldn't have any problem with unloading her gift which she loved. 

The problem I then began to experience was I was gaining too much confidence too quickly. Every free moment I was planning yet another trip into the world. I was rapidly becoming a novice transgender woman which put me at direct odds with my wife. She didn't mind my cross dressing but hated any idea of me taking my gender issues to another level and start hormone replacement therapy. The final chapter of the story was never written because she suddenly passed away from a massive heart attack. I will forever wonder what would have happened if she had lived. I know my success at living as a transgender woman was deeply ingrained and the problem we faced as a couple was similar to being between a rock and a hard place.

Most certainly, gaining confidence in living as your authentic feminine self is one of the most powerful accessories you can have. Much more powerful than that favorite dress or shoes, confidence can help you face the daily world with success.    

From Dreams to Reality

 

Image from the Jessie Hart
Collection

Very early in life, when I was asked what I wanted to be when I grew up, I never told the truth. I would fall back on the politically gender correct answer and say the usual such as a lawyer, doctor etc. The reason I say politically correct is because how I really wanted to answer was with the truth. All along I wanted just to be a woman when I grew up.

I do think, at the time, I did know what a difficult proposition being feminine was all about. Primarily against my will, all along I was becoming more entrenched in a male lifestyle I never wanted. When I was being the square peg being pounded or forced into societies' square hole, I hated it. Even then I put up a brave front and liked the popular male things such as sports and cars, in reality I wanted to be the kid with the new doll baby at Christmas rather than the BB Gun I was gifted. But, life went on along with a pending meeting with the military along with the Vietnam War. I outran the war as long as I could. Finally it caught up with me and I enlisted for three years in the Army, rather than being drafted and insuring me a sure date with Vietnam. 

I dreamed of pursuing a goal of pursuing my early career in the radio broadcasting business while I served my military service for my country. Sure it was all a long shot but the long shot suddenly became a reality with the help of a local congressman whose radio station I worked for. With his backing, I was able to work a year in Thailand for the AFTN Radio and Television Network and then against all odds, managed to end up in Germany working a year and a half for AFN or the American Forces Network Europe. In doing so I was able to experience new cultures on different continents while I tried to keep my eye on the goal I couldn't seem to lose, the desire to be a woman.   

As we approach Halloween season, it is important to note how important Halloween was to me. Primarily because the parties I attended in "costume" as a woman allowed me to experiment on how far I was advancing  my feminine presentation and more importantly could I exist in the public's eye as my dream  woman. I have plenty of posts I will be sharing as we come closer to the actual day of Halloween. 

Spoiler alert, of course I finally did overcome all my doubts of ever being able to live out my dream but found I still had a long distance to go on my gender journey. Every time I think I was making progress, I found I still had so much farther to go.  As destiny directed me, I painted myself into a gender corner I couldn't delude myself to continue. I was ready to take the final step and live my dream of being a full time transgender woman. No more of just thinking I was just a weekend cross dresser, I needed more.

When I did, the final step was till more scary and ambitious than I ever imagined. I still remember the day I gave what was left of my male clothes to the thrift store and resolved to never look back on my old male life. No more just hiding behind my cross dressing until I could escape back to my comfortable world of male privileges. Through it all, my HRT or hormone replacement therapy helped to alter my male body enough to help my difficult attempt to present convincingly as a woman. 

From dreams to reality, the long twisting gender experience was worth it. My lifelong dream was a true one and I learned I was not making anything up. I was living how I wanted. 

Increased Anxieties

Image from Sydney Sims
on UnSplash

When I reached the point where I considered coming out of my gender shell and pursuing a life as a transgender woman, my anxieties went up considerably. 

Possibly, the main issue was just surviving in a new world. Everything was different than I supposed it would be when I experimented as a cross dresser or transvestite. The main difference was I was attempted to insert myself into a new world without the benefit of my old male privilege's I had worked so hard to acquire. When my status was in doubt, I couldn't just bluster my way through and had to finesse it. Especially when I found myself in conversations with other men. When my car broke down one day, I found out the hard way how dramatic the gender change could be when the sheriff who responded along with the tow truck driver refused to listen to me regarding how the best way it would be to get the car back to my house. I finally had to just shut up and play the dumb blond. Even to the point of asking ridiculous questions about how the wrecker worked to the driver when we were heading back. 

Looking back, perhaps the only thing which was really hurt was my male ego who all of a sudden was shut out of my life. 

Through it all, my anxiety continued to build along with the pressure. As it increased for me to be successful on the stops I made on my new gender journey. By stops, I mean  the times I tried to slow down my male to female gender transition to reflect on all that I had learned. It was difficult because I was so eager to attain the next step I was seeking. I shouldn't have worried because huge changes were looming ahead which would make me terrified to go forward yet so excited not to. As the cis woman (born female) friends I began to know, told me so knowingly, welcome to their world.  Any time for reflection I had earned had to be learned on the fly.

As I added layer upon layer of experiences when I went public, adding communication was the one I write about the most. Learning how women uniquely communicate among  themselves was a challenge. I discovered women use a whole different form of talking when men are around or not around. Also, non verbal cues became more important to me as I found myself without the old male privilege of safety. As a man, I could take my personal safety for granted, as a woman the opposite was true. In fact, on several occasions pure eye contact with other women kept me out of possible trouble with men. It certainly took me awhile to learn the new nuances of communicating in the world as a transgender woman. 

The other issue which caused me extreme anxiety was the decision to begin HRT or hormone replacement therapy. I knew before I even considered starting the medications, I would need approval from a doctor which wasn't a given due to my age since I was in my sixties at the time. Plus, if that wasn't bad enough, I knew the changes I would go through would make it impossible to ever go back in my world to my my old male self. Since I was already diagnosed with high anxiety and was on bi-polar meds, this did not make my life any easier at the beginning.

Once I started the hormones though, I knew I had done the right thing. I calmed right down, developed in all the right places and went all out to establish a new life. In addition, as I started to feel at home adjusting to female privilege's, I earned my right to play in what I called the girl's sandbox.  

These days of course I still have anxieties and worry too much but I can say none of my problems come from my solved gender issues. A welcome relief.

Being Better

Photo from the 
Jessie Hart
Collection

Always attempting to be better than the next person was always part of my life. 

Nothing I did was ever good enough for my parents. If I received "B's" in a school course, my grade should have been an "A". If I made sports team, why wasn't I a starting player? These were just a few examples of how life went. I can't ever remember hearing an encouraging comment like way to go from my parents. Similar to so many other aspects in life, I figured it was normal and went on. Little did I know how being better would come back to haunt me later in life.

As I doubled down on my cross dressing efforts again I found nothing I did was good enough. The main problem I had was I was always playing catch up to the other women. They all benefitted from growing up around a peer group which judged them with basics such as makeup and wardrobe. Of course I needed to learn all of it on my own. 

Perhaps one of the most frustrating aspects of the entire transgender process was not only did I need to learn the appearance process on the fly (with no help), when I ended up going out in public, in order to survive I had to be better than the women around me. Perhaps one of the bigger compliments I ever received from my second wife came when she actually asked me to help her with her makeup one night when we were going out. Although she never said it, I knew I had somehow arrived in her eyes as a person who knew her way around makeup. 

It turned out, I was only scratching the surface. Before I utilized the benefits of hormone replacement therapy to grow my own hips and breasts, I resorted to silicone breasts and foam hips to give me a more feminine form. I simply wanted to be the attractive blond woman in the bars I frequented. It worked as I was noticed in a few of the lesbian bars I went to, as I was approached my other women much more masculine than I was. My confidence soared and I felt as if I was finally making in roads into looking better than the next woman. Even though I was transgender. Then it occurred to me I had to be better to just survive as trans. 

Through it all, my natural upbringing kicked in and I thought being better was just part of the game. After all, any cis woman could throw on any old shirt and jeans and go out and no one would question her gender. If I did the same, I would be busted or clocked instantly for being a man in a dress. As unfair as it was, I understood because I had been living with the rules my entire life. In other words, I was up to working harder to achieve my goal of living fulltime as a transgender woman. Which was becoming harder and harder with each step forward I took. I always understood women led a vastly different gender life as men but I didn't understand how much until I set out to prove I could do it every day.

I was primarily blindsided by the communication aspect of feminine interactive conversation. I needed to learn the basics of reading  someone's emotions through their eyes and not their words. Plus, let's not forget the power of a woman's passive aggressive nature. Too many times I remembered trusting another woman only to be stabbed (or clawed) in the back. The whole process taught me  quickly I needed to get better. A feminine public presentation was one thing but being allowed to play in the girls sandbox was another. 

In remembering my post from yesterday, I still need to remind myself of who and where I am as a trans woman. Just a small thing as a smile turned out to be a huge deal. But I was used to knowing I needed to be better. Picked myself up and went from there.

It's All a Dream

 

Transvestia Cover from
the year I graduated 
High School

When I began my gender journey years ago, little did I know many of my dreams would become a reality. 

In the midst of being so young, all things were possible but at the same time impossible. Here I was so all alone in my very dark, isolated closet thinking I was the only one in the world who wanted desperately to be a girl. I would be years away from my first "Transvestia" Magazine where I learned there were actually many others like me called transvestites. Plus, from that point forward, I had other cross dressers to compare myself to. After all, there were so many others who looked wonderful and I could only dream of looking like.

Then, "Transvestia" opened the door to more one on one interaction with other transvestites by publicizing social mixers I could actually attend because some were close enough geographically to be there. I did go and was exposed to a whole new world I never knew existed. There were cross dressers trying to hide their feminine side with cigars and cowboy hats (way before the Urban Cowboy movie) all the way to the impossibly beautiful transsexuals' who I couldn't believe were ever male at all. Through it all, I still had the impression I did not totally belong in either group. I could dream of looking as good as the second group I mentioned, but getting there was going to take me quite a lot of work. 

Ironically, the mixers led me to networking myself to smaller groups of like minded individuals in Columbus, Ohio which was a much shorter drive to where I lived but far enough away I would not be recognized as a version of my male self. Back in those days, he was standing directly in the way of all my feminine dreams and making any progress difficult to maintain. In many ways, he and my second wife were allies against my authentic self who so much enjoyed the new interaction she was having at the small parties she was attending in Columbus. Those attending again included anyone from cross dressers admirers to lesbians to transsexuals headed for genital realignment surgery. I was able to learn from them all and wonder what future path my life could take. Following the parties, I would spend days daydreaming of the next one and would I be able to get time off of work to actually go. With or without my wife who was normally the only spouse who attended the small mixer. I could sense the whole evening was not enjoyable for her.

As much as my gender daydreaming threatened to disrupt my everyday life during the days following the party, I still found time to do my job well. As well as dream of my next move. Which was could I ever think or dream of considering a life as a full time transgender woman. The term was just being coined at the time and to me it meant a new freedom from the old belief transsexual's needed to complete their gender surgery, sever all ties, then move away and just disappear. Perhaps there was hope for me yet.

Through the small sliver of hope I maintained over the years, it was true I could have the life I had always dreamed of. I was able to carve out a life in what I considered to be a feminine dominated world. Gone were the days of trying to please my old male self with how I dressed and in came the days of dressing to blend with the majority of the women I encountered in the world.  It all led to me considering and beginning hormone replacement therapy and really changing my life away from my old male self. Basically as far as I could without surgery. 

What I really learned through it all is if you can manage to live long enough, life is but a circle and some dreams can come true if you can stay the course. Which essentially what happened to me.

Pushing Trans Boundaries

 

Image from the Jessie Hart
Collection.. Back drop, the Ohio
River

Along the way, as the years went by I began to really push many of the transgender boundaries I faced.

A primary example was when I thought I had conquered one of my goals, such as my feminine presentation, I set a new goal. Often I went to different places and/or venues to see if I presented well enough to be accepted as a transgender woman. After malls and clothing stores became too easy for me, I expanded to stopping at restaurants to eat. Which in turn forced me into more one on one communications with complete strangers. I pushed the boundaries past just routine chit-chat eventually into full fledged conversations. I learned the hard way not to worry so much about how my voice was sounding and begin to consider more and more what I was saying. 

For a while it seemed, the challenges I was facing in those years were becoming overwhelming as I pushed my gender boundaries even further. Another major jump occurred when I decided to stop going to the so-called safe spaces which were the gay venues I was going to. I finally decided if I was going to feel like an outcast, I might as well do it in a venue I felt more comfortable in. I began to go to upscale sports bars and restaurants with many televisions and cold draft beer which I enjoyed. Since I stood out from the crowd for being transgender, I minded my own business and tipped well ,so in most places I became a regular fairly easily. On occasion, I still pushed too hard and ended up getting kicked out of a couple places I shouldn't have been in to start with. Lessons were learned.

Slowly but surely the process finally did become a blur. I made new friends and was beginning to thrive in my dream life of being a transgender woman. The biggest remaining problem I had at the time was I was still married. At that point my second wife and I had been together for nearly twenty five years. From the beginning she knew I was a transvestite or cross dresser and didn't really have any problems with it. However, when any discussion at all came up about the possibility of going further and beginning hormone replacement therapy, she drew the line.  Any time I tried to push the boundary farther, the more she resisted.  In many ways it was similar to the rock meeting the irresistible force and it was ugly. More precisely though, I had started the catfight of all catfights between my wife and my inner feminine soul who had finally been able to sample life in the world. Once she had seen the daylight, there was no way my feminine self wanted to give it up. From there, destiny took over.

When my second wife passed away, it didn't take long for my inner woman to take over. She pushed hard and became the dominant force in my life. Quickly it became evident she had known the path to take my entire life. She began to push my transgender boundaries until my life became meaningful again. My male self faded away. 

Her World

Image from Daniel 
Gonzalez on UnSplash

I live in her world and I am grateful to do so.

More exactly, I am a retired transgender veteran senior citizen who waited most of her life to finally fully come out to the world. Why I waited so long to live in her world, is a complicated matter which involved a semi successful male life which was difficult to give up. Not to mention the potential to lose what remained of my family and friends. By living an extended period as a man, I learned the hard way what I didn't like about the male gender. Even still, I wasn't sure I could ever achieve my goal of living as a fulltime transgender woman. Early on I was naïve and thought success as a woman only came when I did my best to appear as one. 

As I started my early emergence into her world, I found the process was going to be so much more complicated. How was I going to survive financially as well as get used to communicating with the public from the viewpoint of an all new gender perspective. I discovered quite quickly which gender stereotypes were true and which ones were false. I always play the intelligence card when I learned I lost a major amount of my intelligence with men when I completed my MtF gender transition. I found I needed to get used to the changes quickly. 

The more I changed, the more prominent her world became to me. Before I totally gave in to her, I made the ill-fated attempt to hang on to what was left of my old male life while I tried to live part time as a transgender woman. It was becoming increasingly evident to me I was so much more than a transvestite or part-time crossdresser. The relatively new transgender term I found, described me more completely. As I decided, I was able to leave more and more of the old male pressure behind me but not before an ill fated suicide attempt. When the pressure became too much to bear. The moral to the story, my inner woman had gone too far to ever return and I needed to realize it. 

These days, through the miracle of modern medical science, thanks to HRT (hormone replacement therapy) I am able to wake up every morning with all my hair, soft skin, breasts and expanding hips. All the physical signs I need to reinforce I am living in her world. Long ago I decided I did not need or could not afford any major gender surgeries to help me along at my age. My gender was securely entrenched between my ears, not between my legs. I could face the world with what I had.

The only drawback is when my gender dysphoria gets the best of me when I take a look at myself in the morning mirror. It's the time when certain days I dream of completing facial femininization to look even more feminine. Then I have to put my vanity behind me and move on. Also, I would be remiss if I didn't mention how internal her world is. The more I transitioned into her world, the more emotional I became as the world around me softened noticeably. Of all my favorite aspects of moving into her world, this was my favorite aspect.

I always say the only regret I have is not transitioning more completely earlier in my life. Perhaps destiny was telling me I had to live through certain learning times in my life. Such as serving in the military, graduating college and having my daughter. Without all of those, I would have missed out on so much of my life. Perhaps I shouldn't  have worried, all along I was living her life anyhow. I was just too stubborn to realize it. One time I had a close cis-woman friend tell me after a Halloween party suddenly tell me if "I ever decided to go the other way" (as a woman) I wouldn't have to worry. I finally listened and made the move into her world.

Set Back to Come Back

Tom on Left with the Author
at a Witches Ball. From the 
Jessie Hart Archive

I have always rooted mainly for the underdog in most things I follow. Especially in sports. Nothing is as thrilling to me as seeing an underdog come back and win. Unless it is against one of my teams.

Lately, as we approach and go by the Fourth of July, there are no more visible underdogs these days as the transgender population. We are easy pickings or low hanging fruit for many politicians who have chosen not to know us at all. Then seek to gain votes by using lies against us. We are even still the weakest link in the LGBTQA+ field because of many reasons.  Primarily because we do not have the economic clout of the gay community. 

However, I didn't want to write a political post today, because you regulars (thank you) know where I stand on the subject of a certain political party which peddles hate of all kinds rather than offer any constructive legislation. Here in Ohio, where I live, they are even leading the charge to change any amendments to the state constitution away from a simple majority just ahead of a vote on abortion this fall. Needless to say, I will be voting no on the issue (one )to keep changes as a simple majority.  

Other than our rights taken away from us, I have other reasons to have rooted for the underdog in my life. The biggest one for me was facing up to the fact I was transgender at all. I took many years of gender experimentation to realize I was deep down a woman all the time just trying to act like a man. It finally took my wife Liz years ago to kick me over the cliff for the final time. I discarded all my male clothes, began hormone replacement therapy and never looked back on my old unwanted male lifestyle. Little did I know ten years ago, the amount of potential hate I could be facing today. Like it or not, I need to beware of my surroundings more than any other woman.

During the period of my life when I was making many mistakes with my presentation it made it more difficult for me to navigate the world as my authentic self or transgender woman. As I said, I still needed to make the final determination I was trans to begin with and what did it mean to me. I was fortunate enough to be just stubborn enough to keep trying when I was rejected as a transgender woman. Plus I found friends who helped me along. They helped me to come back strong when I was set back. Being the underdog they were rooting for, I needed to make sure I was worthy of their attention by doing my best to become a quality person. During that time, I became quite the gender "observer."

These days, as I have written,  I am trying to do more in the transgender community as far as out reach goes. In fact, in addition to the Alzheimer's committee I am going to serve on which spot lights diversity, I signed up for another Veteran's Administration group yesterday which will spotlight VA trans veteran care. My goals for participating in both are if I can help anyone who comes after me, it will be worth it. I don't want them to suffer the setbacks I did.

My setbacks were many and varied and can be turned into comebacks if I can help others in any way from my experiences. I just hope I can.