Creating a Tangled Gender Web

Image from Robert 
Anasch on UnSplash

When I look back at my life, I wonder if I knew all it would entail would I do it all again.

The only change I would make would be to have have the courage sooner to go ahead and transition from male to female. Even though it sounds like a good idea to have jumped off my gender cliff earlier, the problem became the world around me. I am seventy four and the world at large has gone through several different realities when it comes to the transgender world. Back in the day, there was very little feedback when it came to being transgender at all. Basically, there were only two categories, transvestite (or cross dresser) and/or transsexual. Neither of which felt very natural to me, Plus if you went the transsexual route, you were expected to move and leave your old life completely behind. I never thought I could do it either. I still had a daughter I loved plus enjoyed small parts of my male life.

In other words, I was stubborn to the point I thought I could still transition my own way. If indeed I ever came to the conclusion I was trans. As I procrastinated through life, I created an increasingly tangled gender web. I was trying to balance what was left of my male life along with a long term marriage with a woman I loved very much. At that point, I was trying my best to try to discover my true gender self. My web grew ever tangled the more I tried to either escape or relax and enjoy the ride. The ride included taking my transition one step at a time. I found as I struggled in my tangled web I needed more than one transition to move forward. It took the evening when I finally decided to go out to be a transgender woman rather than as a very serious cross dresser just out to escape my male world. to change my mind The difference was major in that I was striving to discover who I really was rather than just playing some sort of game I had indulged in for most of my life. Much of it was in front of a mirror. Naturally the world was much more brutal and I needed to be better.

As it turned out, I was increasingly successful in both of my lives in the main two binary genders which caused my web to be even bigger and more tangled. I ended up sneaking out behind my wife's back, which caused severe problems with my marriage. It was increasingly evident I was stuck in a battle between two women. My wife and my inner woman were both strong feminine people and the war weighed heavily on my overall mental health. Before it killed me, I needed to finally escape the tangled web I was in and begin to live as a woman. Or, as my wife told me, be man enough to be a woman. 

Once I escaped, and with the help of several key friends, I was able to start all over in a new feminine  life. Although, once I began the life, I understood the fact my new life wasn't so new after all. My inner self had been waiting and observing my life just waiting to take over. Of course after I escaped the web, she had her chance and I was living my dream life.  At the least I never led a boring life. 

   

Intersections

 

Image Courtesy Transvestia Magazine

Over the years, I have realized I have experienced several important intersections in my gender development. 

Perhaps my first intersection came when I initially glimpsed my image as a girl in a full length hallway mirror I had at home when I was growing up. I was enamored and immediately wanted to do more. I was hooked to the point where I knew I wanted to do more than just look like a girl, I wanted to be one. Which turned out to be the first indication I had I was more than a cross-dresser, I was transgender. A key intersection into my future.

As I grew up, I faced the same problems other gender dysphoric youth faced too. Our gender closets were very dark and lonely. Particularly in the pre-internet and social media era. Many of you remember when Virginia Prince and her Transvestia publication intersected our lives and we discovered we weren't alone in the world. For me it was a life changing experience when I began to regularly receive my bi-monthly issue of the publication. Of course I wanted desperately to look as good as the models I saw in Transvestia. 

The next major intersection of my gender life came when I started to attend transvestite mixers I read about. Finally, I could meet like minded cross dressers and see what they were up to. What I discovered was a multi layered group of people who were much more diverse than the run of the mill cross-dresser.  I was very enamored with the group I called the "A" listers. Most of them were impossibly feminine and headed towards gender realignment surgeries but others weren't and even brought their girlfriends or spouses. Deep down, I knew where my intersection needed to be, I wanted to hang out with the  "A's" . Just not share their often arrogant attitudes. Even still, I felt I still didn't fit in with either of the groups. I wanted more than just looking like a woman or going under the surgical knife to somehow prove I was a woman. 

Even though I have been able to maintain my attitudes concerning gender surgeries to this day, none of it applied to the decision I needed to make when I approached the choice of undertaking hormone replacement therapy. Again the intersection of my gender life took over and I went to a doctor to be checked out and approved for my hormones. Finally I was on the external and internal gender path I wanted to be on. Externally I was feminized to help me get by in the world as a transgender woman and surprisingly there were many internal changes also. I intersected with my deep seated feminine self and suddenly I was able to feel the world in ways I never thought possible. 

Excepting gender surgeries I never had, I was intersecting with the world as my authentic self in ways I never thought possible. My days living in the mirror and wishing I was a girl were coming true. 

A Night with the Boys

 

Image from the 
Jessie Hart Archives

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

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

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

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

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

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

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

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

 Sadly, it never came again. 

Dream it To be It

Image from Jon Tyson
on UnSplash

 If you are similar to me, many times when you woke up as a kid in the morning you were saddened when you realized the experience you had was nothing more than an evil dream. In other words, in my dreams I was living life as the girl or woman I always wanted to be.

As I grew older, the dreams never went away. Instead they just became more complex and intense. Often the dreams were so intense I would have a difficult time trying to return to reality. Once I did return to my unwanted life as a male, I didn't want to be there. All along I was pursuing a highly secret life in my dark gender closet. When I did it, at the least, I could relieve the pressure of not being a feminine person the best I could do. 

Ironically, it was near this time when I started to participate in organized athletics. During my earliest days of interacting with coaches I learned the basics of muscle memory. To oversimplify the idea, it means you just repeat a motion until it becomes a habit. It turned out, over the years of learning the best I could to cross the gender border, I used the idea of applying muscle memory to certain aspects of moving as a woman. I practiced and I practiced until it became difficult to switch back to moving as my old male self. 

During this time also, I was dreaming more and more concerning the possibility I could ever live fulltime as a transgender woman. The more positive feedback I received the closer the dream became to reality. I began to seriously dream my biggest goal might become become a distant reality. I knew then I had serious work to do. I began a stairstep method to my male to female gender transition. Once I accomplished going to a certain venue, I would try another to see if I could learn anything new. The whole process was exciting and the whole time I was living my old unwanted male life I was dreaming of my next feminine step.

Possibly, the biggest step I always mention was when I needed to undertake the new world of communication as a woman with other women who showed the most interest in me of the two primary genders. For the most part, men didn't pay me much interest for whatever reason. Quickly I learned the power of non verbal signals as my life began to change as well as adjusting to a world of passive aggression.

Once I survived all of the steps I was taking to live my dream. At the same time doors all around me were opening and closing around me. By opening, my dreams could become a reality but by doing so I finally needed to take the final steps to stop all interaction with my male self. So closing became more than I bargained for and the stress became unbearable since I was risking so much. Life as I knew it as a man would be over and losing all the male privileges I worked so hard for was so scary. Mental health problems became a reality as I my ultimate dream drew closer. Of course I was worried my dream would become a nightmare.

Spoiler alert, my dream was not a nightmare and everything I hoped for became a reality as I was able to achieve my ultimate goal of living a feminine life. Call it muscle memory or anything you want but I was able to dream it to be it. I was fortunate.  

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.

The Ultimate Obsession

 

Image from Brett Jordan
on UnSplash

As I recall, the ultimate obsession I had with being feminine began with explorations into my Mom's clothing and makeup. Once I started I couldn't let it go.

Little did I know, I would need to follow quite the winding and rough path as I crossed the gender border from male to female. As soon as I conquered one of my goals and escaped my very dark and lonely closet another wall or barrier would crop up to challenge my obsession. An example would be how I imagined just improving my outward feminine appearance would be enough to help me live in the world as a transgender woman. All the process really did was set me up for other huge challenges.

Challenges such as how I would or ever could learn to communicate with other women in their world. Nothing in the process was easy and often terrifying. The old "no pain-no gain" saying proved to be all too true. Just attempting to modulate a feminine sounding voice to match my appearance was the ultimate challenge. Plus I needed to learn to always make eye contact with other women as we engaged in conversation. A simple statement saying I loved another woman's ear-rings often proved to be the ice breaker I needed to survive in my new gender world. 

Through it all, my male self was fighting me all the way. Every move I made to try to enable me to be more feminine was a problem to him. Deep down he knew he was fighting a losing battle because when I was pursuing my authentic self I felt so natural. So everytime I was questioning the path I was taking, the bottom line was if it all felt so natural, it was the right thing to do. Somehow I needed to conquer my fears and temporary setbacks and follow my own personal ultimate obsession. Follow it I did.

No matter how complex my life became as I ended up attempting to share a life between the two primary genders, until the pressure became too intense to survive, I did my best to live my life. My male self kept resorting back to what he had always done...internalize his feelings and hope for the best. His best never came as I continued my path towards my ultimate obsession. Even then, I had no idea if I could make it to my ultimate goal of living a life as a transgender woman. Fulltime with no interference from my old male self. 

As I always point out the struggle nearly killed me and I would not wish it on my worst enemy. I was one of the lucky trans women or trans men who all of a sudden found the doors opening which would allow me to finally follow my obsession which had followed me my entire life.  Destiny showed me the way around life's setbacks such as close friends and family dying. It all allowed me to have very little resistance to living my own life as I saw fit. Also near the same time, the Veterans health care system I was part of started to provide help with hormone replacement therapy, which I was fortunate enough to be healthy enough to be a part of.

In short, my life which was very much in shambles faded away and I was finally able to achieve my ultimate obsession. To lead a feminine life and even to become remarried again to my wife Liz who accepted me all the way. 

The path I took was never easy but on the other hand, my trip was never boring and provided me with a unique look at life others never have.  

It Was All a Dream

Image from Marcos Paulo Prado 
on UnSplash

Similar to so many other transgender women and trans men, when I was young often I woke up sad in the morning after vividly dreaming I was living as my preferred feminine gender. 

Of course, then depression set in when I had to face yet another unwanted day as my old male self. On those days, very little motivated me to get going. Somehow I managed to make it through another day. On the good days, I had figured out how I could sneak around my family's back and cross dress in my small wardrobe and admire myself in the mirror. In the meantime, I tried to study the cis-women (natural born) around me to see if there was anyway I could copy their dress or mannerisms without being too obvious. I was so envious.

It took me years and even decades to figure out how totally reversed my gender dreaming really was. To this day, after living as long as I have as a full time transgender woman, my dreams are still flipped. In other words, most of my dreams still involve me as my old unwanted male self. I'm sure the main reason is the fact proportionately I still have lived the majority of my life in a stressful male world. To be successful I just had to learn the game well. All of which has carried into, and remains a substantial portion of my self-conscious thought. 

Plus, on occasion, I feel as if my entire gender existence has been nothing more than an extended dream. Perhaps it is because for such a long period of time I considered being able to live as a transgender woman was just an impossible dream. Then when I began to leave my mirror behind and break out of my gender closet into the world, I began all the changes I would need to do to live a new fulfilled life. Suddenly my life evolved from just doing my best to appear as a woman, all the way to communicating effectively as a trans woman with other women in the world.   

It was around this time of gender discovery when I started to believe I had my whole life backwards. There were certain aspects somehow I needed to do as a male but overall the other set of experiences I went through could have been lived by my dominate feminine self. I couldn't believe how much easier my life became when I finally gave in to her and let her live. She in essence was telling me she was right all along and she was.

It turned out, my dyslexic self had my gender mixed up also. All along when I  considered myself a male to female cross dresser, in reality I was a female to male cross dresser just trying to survive in an unwanted world. 

Now my past is mostly a dream, some parts good and others bad. Perhaps one of these days my sub-conscious will flip into dominant feminine role too and my dreams will become predominantly feminine in nature. I suppose if that is all I have to complain about, life is good.   

The Slippery Slope

Image from the Jessie
Hart Archives

I can't imagine the freedom some younger transgender youth have when their parents approve of and actually help with their gender transition.

I can use the example of my own grandchild who benefited completely from having the support of both of their parents. (It is the grandchild's choice to be referred to as they.) Of course how I grew up was totally on the opposite side of the acceptance spectrum. I was expected to be the best boy I could be and if I wasn't. I was always expected to do better. As much as I resented being put through all of that, the process probably set me up for success later in life. When I faced difficult situations, I just kept trying until on occasion I found success. 

Finding success as I sought out what to do concerning my increasingly serious gender issues proved to be my greatest win but it did not come easily. I compare it to being on a very slippery gender slope and finding yourself losing control the perceived damage. I was very scared on what could happen if I completed my male to female gender transgender transition I could lose everything I worked for in my semi-successful male life such as family, friends and finances to name a few of the major ones. 

Once the sliding began and I started to slide down the slope, I couldn't stop. The biggest problem was I didn't really care because for the first time in my life I felt natural in my own skin. I didn't have to put up feeling just a little all the way to being completely foreign when I was successful as a man. Nothing seems to have been enough until it came time to being a success as a transgender woman. The biggest move came when I made the decision to slide further down the slope and commit to being fully trans and away from being a highly active cross dresser. I was becoming more and more convinced I was doing the right thing by throwing my male life away and living a feminine one. 

What became increasingly obvious, it was time for me to lose my grip and tumble the remainder of the way down my gender slope. I finally could take the effort to jump the gender border before it killed me. I was trying my best to live equally between the two binary genders. Male for three days a week and female for the rest of the time. The resultant ripping and tearing led me to a major mental health breakdown with a suicide attempt. I saw the writing on the wall and finally decided to slide off my slippery gender slope. When I did not know was how my new circle of friends would be around for me to soften my landing.

Not only did my circle of cis-women friends accept me, they unknowingly helped me understand the basics of surviving in the feminine world. I call it being able to play in the girls sandbox.

Surprisingly, I survived the slippery slope much easier than I thought I would. Sure I had a few scratches and scrapes on the way down. Overall, as I said, I was the fortunate survivor of a very difficult gender struggle. Hopefully, in their own way my grandchild will not have to endure such a slippery slope.

Emotional Blackmail

Image from Callum
Skelton on UnSplash

Emotional blackmail is another of those terms or labels which is difficult to describe or understand.

The way I look at it is, the blackmail describes the portion of my life I lived with my second wife when we constantly battled over my increasingly feminine gender identity. In fact, now, in hindsight I look at the time when two strong women were clashing with each other. My wife and the other was me. Every time I was successful when I went out as a transgender woman, the bigger our fights became. Examples included the time when I went to a transvestite or cross dresser mixer when we lived in New York. The gatekeepers who were placed to keep cis-women out made me show my identification to prove I really was a guy. The entire incident put me on cloud nine for days following but on the other hand, made me very difficult to live with. Predictably, my wife and I clashed and my inner woman felt who was my wife anyway. 

As life went on, the emotional blackmail continued and even worsened. Our sex life worsened because I insisted on making love as two women. She hated the idea and all activity ground to a halt until she passed away. It was during this time also when I was sneaking out more behind her back and meeting new people for the first time. Ironically, I was approached by way more women than men and primarily became friends with lesbians for some reason. Whatever the reason was, I was enjoying the new company I had found and was able to learn so many things from them. One night on one of my gender parties I went to I ended up leaving with a single lesbian woman and going to a dance club in Columbus, Ohio. Nothing physical happened so I considered it another case of emotional cheating I was doing to my wife of twenty five years.

Sometimes I wondered if the emotional blackmail I was subjecting my wife to was worse than any other form of abuse. Sadly or not, I couldn't do anything about my quest to understand and be a better woman. Probably, what was left of my old male self who loved my wife dearly and on occasion had enjoyed our life together was the biggest obstacle to changing it all and coming out fulltime. He kept screaming at me to not give up and the ripping and tearing of living between two genders nearly killed me. Plus, after or during one of our biggest fights, my wife told me something to the tune of why didn't I be enough of a man to be a woman. It would have certainly have been the best way out of the torment if I had only listened. Of course I didn't. 

I was one of the fortunate transgender women as I found a soft landing spot with plenty of assistance when I transitioned. I learned to rely on my feminine instincts which had been ignored for so long as my new life began to take shape. And most importantly emotional blackmail faded into my past as something which never really happened. We all know it did. It wasn't right and I wasn't a strong enough person to do anything about it. 

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.    

The Light

Image from Junior
Ferriero on UnSplash

 
Sadly, most transgender women or trans men experience complete darkness in their gender closet before they are able to come out and explore the world.

Of course in the pre-internet period, gender information was very difficult to come by and it wasn't until pioneers such as Virginia Prince came around did printed material begin to surface on a regular basis. As well as the so called transvestite mixers which began to crop up in other areas except the East coast. For those of us in the Midwest and other places, finding and meeting other like minded cross dressers seemed to be the impossible dream. The light in the gender closet was dim to say the least. 

Perhaps the worst part of seeing the light was determining exactly what it was. Could it be a beneficial beginning to escaping the severe gender dysphoria I was facing, or was it merely the light of a train rolling uncontrollably towards me. At any point of time, discovery of my feminine desires could lead to severe consequences to the male life I had worked so hard to survive in. It took me years and even decades to figure out the light wasn't the train. Partly because of all the time I wasn't sure it wasn't the train.

Those were the dark days of my gender despair. The days of venturing out in the public's eye only to be laughed at and rejected which led to ill-advised "purges" of my feminine wardrobe. Somehow, deep down, I knew the "purge" would only last a few days and the fleeting freedom I felt wouldn't last. I was right and before long, my desire to rebuild a feminine wardrobe and wear it became strong again. This time I wanted to climb on board the train and ride it to a new found transgender freedom, away from my old male self.  Rather than the light at the end of the tunnel being a negative, I deeply wanted to turn it into a positive.

It was approximately this time of my life, in my thirties and early forties, when I met others whom I could identify with as far as my gender struggles went. I found I didn't have to drive far to Columbus, Ohio for small mixers with a diverse group of people ranging from cross dresser admirers all the way to transsexuals. All of the sudden, the light became a beacon on what my life could become if I worked on it hard enough. I found achieving my possible goal of living a feminine life meant so much more than just appearances. My second wife kept pounding on me to be more and I took a long time to realize what she was saying. Surviving as a trans woman would mean learning to live a new multi-layered life.

Even though I had made it a huge priority to study women all my life, I needed to use the light to take my studies to another level. Think of it this way, I was pursuing a new masters program in gender before I could put the male past behind me and move forward.

Finally I arrived at a point where my closet door had opened widely and my long hidden feminine self was able to take over. She was able to take over the light and enable it to be so much brighter.

Witches Come Together

 

Witches Ball Photo from the
Jessie Hart Archives...

Not so long ago, I was part of a group of Wiccans who put together sizeable parties every Halloween called "Witches Balls."

At it's peak, over five hundred people attended in a very appropriate huge vintage venue across the Ohio River from Cincinnati. Liz and I had plenty of experiences with the event because we went on several dates there before we were involved with organizing it. One of my fondest memories came when the Johnny Depp/Jack Sparrow impersonator flirted with me one year when the party was featuring pirates and also belly dancers. I also enjoyed watching the sexy gyrations of the dancers as I was given a chance to sit down with Liz and kick off my heels and watch. As much as I was enjoying wearing the heels, I was still paying the price for wearing them too long. 

Of course, since it was Halloween, costumes were an intricate part of the event and I was always on the outlook for the occasional cross dresser whose look was just a little too good. As close as I ever came was when I ran into a Facebook acquaintance who is also transgender who was selling her jewelry at the party. Overall, I was surprised I never was able to see anyone else who dressed as a woman for the evening. One thing for sure, I didn't need anyone else's approval  and I had a great time. 

Sadly, the larger witches ball's have become a thing of the past around Cincinnati and now are only held in smaller venues such as bars or taverns. So Halloween has increasingly become another rather boring day. However, I will be forever in debt of Halloweens past as they opened doors for me to express my true self long before I ever thought it was possible. We don't even have enough young trick or treaters stop by to see if any of the young boys are still dressing as cheerleaders. 

I do miss also the huge volunteer organizational effort it took to enable the events to happen at all. The feel good portion of the whole affair happened when we were able to donate a fairly large sum to one of the local homeless shelters. Karma is real and it is always nice to pay forward when you can. 

Since I live fulltime as a transgender woman for so long now, I don't need the feminine experience of a Halloween costume to shore me up. But on occasion I still miss what Halloween did for me in my life. Along the way, it became my most important, influential holiday. It opened my eyes to what could be possible and I could actually live out my gender dreams.   

Welcome to Hell

Inside "Casa Susanna" A dream trip I never made. 

My early days of dealing with a severe case of gender dysphoria can only be described as being in hell.

For those of you who can remember the dark days of information before the internet and social media, you also recall the days of being completely alone in your dark gender closet. Since I was raised in a very male dominated family, I knew escaping my own closet was going to be difficult at it's best. I was forced to sneak around behind my family's back to steal away the time to cross dress in my small stash of girls clothes and makeup. I even resorted to storing away my clothes and a spare mirror in plastic bags in a hollowed out tree in the woods next to our house.

Through it all, I knew the whole process of dressing as a girl made me feel better but somehow would have to be enough to get me by. I followed the vicious cycles of feeling the gender euphoria of being feminine in my mirror with deep depression when I was denied access to my clothes. I learned very early I wanted to do more than look feminine, I wanted to be feminine. Way before the term transgender was ever invented. to put the date in perspective, I would have been in the 1960's before I hit my teenaged years and still years away from my military duty and discovering Virginia Prince and her "Transvestia" publication which only dealt with so called heterosexual cross dressers or transvestites. I mention "Tranvestia" again because it was my first link to other like minded people. 

From then on, I knew I wasn't alone and could even go to transvestite mixers which were within driving distance of me. Even though I had discovered others, it turned out I was still dealing with my own personal hell. I still needed to be able to deal with the gender euphoric times followed by longer periods of gender dysphoric down times. Ironically I brought much of my hell on myself by not knowing the best ways to dress and apply makeup to best present my inner female to the public world. I had a difficult time dealing with all the stares, all the way to laughter when I tried to take on the world. Once I began to learn how to best handle the public, along came the Army to disrupt my life. As much as I didn't really want to experience military life at all, specifically I didn't know how I could exist three long years without having a chance to express my feminine self. For years, as I waited for the Vietnam War to draft me, I went through hell considering it's ramifications to me.

One way or another, I made it through the three years and couldn't wait for the relative freedom I had to escape my own personal gender hell, no matter how briefly. 

My big escape came when I made the highly personal decision to stop considering myself a cross dresser when I went out and I transitioned into thinking of myself as a transgender woman. Semantics to be sure but a huge move for me mentally. By mentally transitioning I was able to take a huge step out of my own personal gender hell. In many ways, I entered my golden years of MtF gender transition by leaving much of my hell behind and be able to increasingly explore the world. 

From then on I was able to free myself from my gender dysphoric hell and start to live my dream life as a transgender woman. Although I want to say the process was worth it, I wouldn't wish my journey on my worst enemy.

Coming Out to Employees?

 

Halloween Witches Ball Image
Liz on Right 

As we rapidly approach Halloween and my wife Liz's operation coming up, I thought it was time  for another Halloween experience while I still had time. 

This one happened when I was managing a fast food restaurant just outside of the New York City  metro area. More precisely, very close to the Bronx. As Halloween rolled around, once again  I was stressing out about what I was going to wear. The pressure was on since it was nearly impossible for me to leave the house we lived in dressed as my feminine self. I was back in the mode of waiting another year to escape from my mirror until the next Halloween rolled around.

As I faced the pressure head on, I decided to go all out as I decided what my "costume" was going to be. I put together what I thought would be a potentially a sexy look without crossing the line into being trashy. I pulled out my shortest dress, along with my highest heels. Most certainly, my wife's most hated outfit on me. In this case, I used her motivation of me to spur me on. For once, since she wasn't going anyhow, I decided she would have to get over it. I would have to put up with her displeasure with me for the next several weeks but it was worth it for me to pursue my dreams.

As I said, my outfit was going to be short and sexy as I to the best of my ability fool the world to what my true gender was all about. Little did I know, I would be able to find a situation where I was able to blend right in. 

As it turned out, one of my assistant (woman) managers was going out to one of her local taverns to celebrate Halloween with her friends and she invited me along. After I dressed, did my makeup and hair and was ready to go. When I arrived at my manager's house, it turned out the friends she was going with turned out to all be tall and beautiful . As it turned out, by pure accident, At least in the height department., I fit right in. When I first saw all of them, as the room grew silent, you could have heard a pin drop. Time seemed to stop for me as they examined me from head to toe. Of course I could only guess what they were thinking as we left for the short walk to the venue where we were going. Thank goodness for me (in my heels) it was not a long walk.

As we arrived, I learned a valuable lesson about being with other single women who were attractive. The first thing the women did was essentially split and worked the room. They left me on my own which was an experience in itself. After I bought a drink and found a seat at a small table, I settled in to try to enjoy my evening in the world as a novice transgender woman or even a transvestite. And it turned out, the night was far from over. As I tried to sit by myself, I attracted attention from an older guy who kept bugging me to dance. Which I refused although deep down I was flattered. Finally, the night was over, the group of women broke up and headed their own ways. 

I ended up back at my restaurant which I knew was closed by then. What I didn't count on was, the closing crew would just be getting done and they would see me in my "costume." Surprisingly to me, the response was positive even to the point of one of the guys saying I had good legs. 

More importantly, the backlash from me dressing as a woman for Halloween was a non starter for most of my crew and life went on. The only variable was my assistant manager who I think couldn't wait to tell my boss who smiled at me differently for awhile. However it was New York and there were bigger issues to deal with than me dressing as a woman for Halloween. Which was one of the reasons I wanted to move there from our native Ohio to begin with. 

As far as my second wife went, she finally made me pay my dues as only a woman knows how to do. I learned from it and moved on. Knowing I had been able to experience a truly wonderful evening to think about and remember forever. 

Pre-Political Meetup

Image from the 
Jessie Hart Archives...

 Long ago, following a few of my Halloween adventures when I did my best to stay away from looking trashy on Halloween. I was determined to do my best this night to be mistaken for a cis-woman. 

I decided to attend a party I was invited to as a professional business woman. The get-together was being held at a restored Victorian mansion which was owned by a casual friend I knew. A wide range of people were invited. I worked at a radio station in town at the time and since my first wife never really was into Halloween, I was left on my own to find someone else to accompany me. It turned out one of the news reporter women at the radio station had an invitation also, so we agreed to go together.

In no time at all, it was time to put together my "costume." I started with shaving my legs and putting on a brand new pair of panty hose. From there, it was very easy to choose an outfit from my growing feminine wardrobe. The years have clouded my memory so I do not exactly remember what I wore except it included heels and my red wig which I loved so much. Of course when my "date" saw me she was amazed and amused I would go to such lengths to be noticed on Halloween. Plus she was more than impressed when I was able to do such a good job walking in heels "for the first time." 

When we arrived, the hosts had done a wonderful job of decorating their old mansion. Even including a vintage glass topped coffin with a real skeleton. Most importantly, I was able to relax and enjoy being out of my gender closet for the first time in a year in public. I was truly a novice transgender woman just exploring the possibility for the first time if I could be accepted in the feminine world. 

As the night progressed, guests came and went and the alcohol flowed. Also I was receiving plenty of positive feedback on my "costume." I had made the correct choice to dress as a professional woman for the party. Most of the other guests assumed I was just arriving late from work and didn.t have a chance to dress up. Which was exactly my goal. 

The most flattering happening came when this couple approached me and said how impressed they were with my "look." They were totally fooled into thinking I was a woman. Through it all, I recognized the man and his wife as a newly elected politician on his way to Washington, DC. Plus they wanted me to tag along with them to another party they were going to,. Since I didn't know where they were going and was with someone else, I had to politely decline the invitation. Leaving me to forever wonder what would have happened if I had decided to go along with them. 

Who knows? Perhaps my political career was ended before it even had a chance to begin. At any rate, the evening turned out to be a blast and my "date" never mentioned how I looked again. It wasn't too long when she landed another news job and moved away anyhow. 

As far as the politician goes, he turned out to be re-elected several times to congress. I lost track of him also when his political career was over. I stayed friends with the owners of the mansion over the years until I moved away and they divorced. Maybe deep down inside I was disappointed no one brought up how I looked on Halloween that night so long ago. I was probably desperately trying to out myself and no one cared. Or I was so good at hiding my feminine side with my intense male self, no one could see my true self. 

It wasn't to be until years later, my feminine self finally took control and Halloween "costumes" became a thing of the past for me.

The Power of Halloween

 

Image from Danie Franco
on UnSplash

During my life of realizing how deeply my gender issues went, the more important Halloween parties became to me. 

I could say going to Halloween parties dressed as a woman began innocently enough. All I really wanted to do was go out and feel the thrill of wearing a short dress with freshly shaven legs and new silky panty hose. Little did I know, I would experience so much more as the years went by.

My first "costumes" were simply trying to dress as trashy as I could, trying my best to "thrill" my friends into thinking I could be an attractive woman. It turned out to be a process I would go through for Halloweens to come. Dressing to thrill just wasn't enough, dressing to be mistaken for a woman became my goal. 

Even still, my first Halloween party when I seriously dressed as a woman was a memorable one from several different reasons. Ironically, the party happened when I was in the Army stationed in Germany. I was fortunate when I was assigned to work at the AFN (American Forces Radio and TV Europe). Naturally, compared to others with more strictly military duties. I also managed to live in a separate barracks with others assigned to a medical commissary. We had it easy. 

When Halloween rolled around, the people in the medical group decided to have a big party and it was my big chance to put two years of being cross dressing frustrated behind me. Finally I had the opportunity to cross dress again if only I could find the clothes and makeup I needed to look the part, Since it has been so many years ago, 1975, I don't really remember how I came up with all the necessities I  needed to dress as a prostitute but I did. Short mini dress, high heels and long blond wig completed my outfit and to the party I went. I ended up having a great time, which included too much German beer and Jägermeister. Through it all, I remember all the prying hands I needed to fend off from places they should not have been.

The big question I had was, did I do too good of an effort to be attractive? I always considered shaved legs was the deciding point between someone who casually dressed as a woman for Halloween and someone else who was way too serious. Plus, I still had to keep in mind, I still had a year to go in the Army and I did not want to lose my chance for a honorable discharge if someone looked at my "costume" and decided it was too gay. 

It turned out not to matter anyhow. A couple weeks later when my group of three close friends and I got together for dinner (and beer) I ended up being indirectly asked how serious I was about looking like a woman. I blurted out very serious and that I was a transvestite. The first time I had admitted it to anyone. As free as I felt at the moment, putting myself out there could have been potentially very harmful to me as I tried to finish my military service. Fortunately nothing ever came of my letting others in to my "secret" and I served out my time with an honorable discharge. 

From then on, I couldn't wait for my next chance to leave the mirror behind and express my feminine self in the world. Sadly, the only time I could do it was Halloween which I will have plenty of interesting posts about coming up.   

Staying in Your Own Lane

 

Image from UnSplash

Staying in each others own lane has been increasingly difficult for the transgender community. 

Much of our existence changed under the four year rule of a certain former president who brought out hate in our country. All of a sudden, more and more people became less reserved about changing lanes and invading the LGBT world. Recently I have a close friend whose world was invaded by gender bigots crashing her world. It happened at a relatively upscale casual dining restaurant very close to where my wife Liz and I live and I felt so bad for my friend. 

To make a long and personal experience short, her and her wife's dinners were ruined by other patrons who referred to her as a "Fa--ot" and worse, such as religious slurs. In our experience in the venue, I was laughed at once by a server but that was about it. Even then, we felt bad enough about it to never go back. Plus, that was years ago and people and times have changed. So many think it is acceptable to hurt others with their feelings. So now, it could have been so much worse for me. 

I have said or written it many times how fortunate I am to have Liz with me most of the time when I interact with the public. She is approximately the same height as I am and opens many gender doors for me and others have a tendency to stay in their own lanes. An example happened a couple days ago when Liz went to one of her pre surgical appointments. As always, I didn't have any issues in the doctors offices and especially when we went to a nearby coffee shop to order a cup of caffeine and a breakfast sandwich. The coffee shop was very near one of the  local major university campuses, so the extreme majority of the patrons were college students who certainly had no gender issues other than their own.

In other words, all the people I encountered had no reason to leave their own lane and enter mine and I was free to enjoy my own transgender life. 

For all of you who are attempting to live as your authentic gender selves, I hope people stay out of your lane and you can enjoy your life. I know I am preaching to the choir but you deserve a stable and pleasant gender existence. My blog gently weeps for all of you locked in your dark closets or are just out in the world trying to stay in your own lane. I know my basics of being out in the world is easy, be nice to everyone I can and tip well when I need to. I also benefit on occasion from being easily remembered because of how well I present as a transwoman or don't. 

Either way, I am sadly waiting for the day when a gender bigot decides to veer out of their lane and into my own. 

Fashion Trends and Circles

 

Image from Jonathan Borba
on Unsplash

Following thinking more and more about yesterday's post, I finally figured out I left out too many details of me supposedly not wanting to wear skirts. 

The post was called "Skirting the Issue" and basically zeroed in on the negative feedback I received when I first entered the world with other cross dressers. I was told, if I wanted to wear pants (or slacks) I should just stay dressed in my male clothes. I rejected the comment and proceeded to follow my own path as a novice transvestite in the world. 

Where the experiences changed were when much later I again started to go out in the public's eye. Overall, my first experiences with another person were with my second wife who was very conservative in her dressing styles. In order to try to gain favor with her, I attempted to dress the same way. Mostly relying on jeans or slacks on the rare occasions she went out with me. It didn't seem to matter as she never seemed to like or relate to my emerging feminine self. Ironically, I was many times on the opposite end of the cross dressing spectrum when she wasn't around to judge me.

What happened was, during my earlies Halloween experiments, I dressed as prostitutes in very short dresses or skirts. I always made sure to shave my legs and threw caution to the wind when it came to friends and strangers reacting to me doing just a little (or a lot) to look like a woman. Deep down I was so flattered when I received compliments on how good my legs looked. At that point, I did become obsessed with showing off what I perceived to be my most feminine asset which of course were my legs. It took me forever it seemed to figure out stuffing my male torso and big shoulders into a mini skirt just didn't work. I was just taking the easy way out and cross dressing for the mirror in front of me and not the world.

Over the years I was still able to take advantage of certain fashion trends which came and went. A couple in particular stay in my mind as being beneficial to showing off my legs and still be fashionable. The first was in the 80's I believe when many women where I lived were wearing oversized sweaters with undersized mini skirts. I was able to acquire both fashion items and be positively received in the world because I was able to blend in and not be trashy in my appearance. Plus, I was thrilled to be able to feel the cool air on my freshly shaved legs.

The second fashion trend I was able to take advantage of was when professional women were wearing business suits along with short skirts. Many times they wore colored opaque panty hose and kitten heels to round out their outfits. I was able to find a pale green suit with a short skirt which fit me well and even matched it up with opaque hose that matched. I already had my blond wig and kitten heels so I was ready to go to the upscale malls where I lived and shop for as long as I wanted with no incidents.

I guess where I began to fixate on wearing jeans or pants sometimes again came when I began to be able to find the "Boho" fashions which took me back to my youth. I wore out my jean skirts and tattered bell-bottomed jeans until they had to be discarded. 

Finally I went full circle to the days of trying to appease my wife when I was able to be accepted by a small group of lesbian friends. Most certainly, I wanted to blend with them. Especially when we went to lesbian mixers. It was a challenge to go back but I did because I wanted so desperately to blend in.

I learned through fashion, life is nothing but a circle if you can live long enough to experience it. Living my life as a transgender woman just made the point more evident. 

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.  

Looking back...Again

Image from the 
Jessie Hart Archives

Rumor has it October is my birthday month and this year I am coming as close as I can  to being seventy five years old without actually being there.

As I am not really in the habit of celebrating anything but my milestone birthdays, so this year is not really in that category, yet. 

Even still this year for my birthday I find myself looking back at how I lived my life, good and bad. As I reminisce, the first thing I always encounter is how long I waited to let the world in to my true self. In other words was waiting until my early sixties until I came out to the world as a transgender woman. The time just felt right for me for several different reasons. The first being my life as a three days a week cross dresser just wasn't cutting it and I was becoming increasingly frustrated with attempting to live a life between two of the main binary genders. I felt as if I was being completely torn apart when I did it. 

I also felt as if I had taken my unwanted male existence and made the best of it for as long as I could and it was time to let it all go. During my male life I had achieved such milestones as fathering a child, completing an education, serving in the military and holding down a good job. And, maybe most importantly, my body had given me a healthy life to work with. To this day, the only operation I have undergone was having my tonsils removed. Most certainly, good health is the key to a good life. 

Perhaps, as I look back, I was a user when it came to my male life and a taker when I transitioned into a feminine world. When I made it into my sixties, I had used up most all of the male privilege life had to offer and it was time for a change. If you want to fault me for feeling this way, I plead guilty as I played the best I could the gender cards I was played. During my life, on occasion, I did gamble on moving and job changes to advance my male life, what I didn't gamble on was when I decided to complete my male to female gender transition. What I did do was explore every facet of the possibility I could live my dream and exist as my feminine self. I went out into many areas of the world to see how I was accepted and in most cases came back with a positive response.

Also, I know in some circles, waiting so long to trnasition makes me less transgender than others consider themselves to be.  I can only say, the past I lived and survived in was a different world than the one today.  Plus, I can care less what anybody says about me except my wife and daughter. With the outside world bringing all the pressure on the trans community politically, it is time to put petty differences behind us and go forward together. 

Perhaps the benefit of age can give us a better look around and not focus on the red hatted crazies who still support a former president.  But on a positive note, it is always good to put another year behind me and always hope for better in the year to come.