A Hot Mess on Another Veterans Day

Image from Tim Mossholder
on UnSplash.

Before I get started on my main post, I would like to take a moment and salute all the members of the population of this country (US) who have served in the military forces. Thank you for your service. On top of the many gender conflicted men and women who served their country so well and later came out into the world, I have always suspected there are still far too many who are still in their closets waiting for their chance to join the world. With the positive election we had, all your chances to come out may just have improved. At least,  I hope so.

As far as my time in the military went, the hot mess part mainly came during the years I waited to see if I was going to see the Vietnam War up close and personal all the way to figuring out what I was going to do about the draft, if the long, drawn-out war was still going on through my high school and college years. During those confused years, my life was a hot mess as I thought about what I was going to do about my two main pleasures in life, my cross-dressing and my beginnings of having a solid commercial radio DJ career. Since I knew my love for cross-dressing would have to be put on hold in the Army, I hoped that somehow, I could maintain my career as a broadcaster in the service. 

I started my search by going around to all the military branch recruiters to learn if they had any job listings for what I was looking for at all and learned only one did and that was the Army and it was exceedingly difficult to get into.The only thing I had going for me at that time was that the radio station I worked at was owned by a powerful congressman, so I hoped that I could use him to my advantage. I wrote and sent off a letter to Washington saying I would serve my country and was there anyway they could help me salvage my career while I served. To my amazement, in a relatively short amount of time, I received a letter back saying they would put me in contact with an officer they dealt with in the Pentagon and for me to deal with him. The power of having a congressman behind worked for me again as the officer in the Pentagon said he would look into it as well as other jobs doing attache work in embassies around the world. Which was not what I wanted, but better than the alternative.

Then I needed to be on hold until I went to infantry Army basic training like everyone else. I was able to put off going as I went on a six-month delay program to let my sources work on my future, even though, I kept telling myself I was going to put myself on some sort of a physical training program before I left, I never made it and was just a hot mess of drinking and self-pity as I faced my military future. Before I knew it, my time had passed and I was headed to Ft.Knox, Kentucky for basic training in the middle of winter. On my way, I learned I was far from being the worst hot mess on the bus we were traveling on as one of the guys in front of me was openly crying out loud. As for me, I could not wait to get off the bus and get started on the next three years of my life. 

It was not until about three weeks into basic that the attitude by the drill sergeants started to change towards me. I was very naive at the time and did not put together the fact I was receiving mail from the House of Representatives and the Pentagon and all of the sudden I was made a squad leader. A position normally reserved for those troops who performed the best at physical training and marksmanship. Neither of which described me. I finally woke up to the fact that no one was reading my mail, but someone was certainly noticing it and my hot mess of a life in basic began to calm down because it was beginning to look like I would get the impossible job in the Army I had hoped for. In fact, there were only sixty plus openings in the entire Army available at any one time. 

The rest of my three years in the military turned out to be a blur as I worked on AFRTS military radio and television stations in Thailand and Germany. It was not until I was discharged did my life revert back to the old hot mess it had always been because of my gender dysphoria. I got out of the Army about six months ahead of my future first wife and I was so conflicted about who I was that I was seriously considering meeting her at the airport dressed as my authentic feminine self but I did not and life went on as I began to try to outrun my gender issues. In the next decade, I tried changing everything from wives to jobs to locales to try to outrun myself which did not work. I was doomed to be a hot mess until I faced the reality of who I was. I was not a woman trapped in a man' s body. I had always been a woman cross-dressed as a man. 

Finally, I faced reality and my hot mess of a life straightened right up. I learned to appreciate what life had given me over the years and I had no right to deny what it was showing me to live. More importantly, I was ready to share my wisdom with the world if anyone was in need of it because I certainly did not want anyone else to go through what I went through. That is why I write.

If you are facing a mess with the gender in your life, I hope everything becomes better for you and you are able to face your own reality better than I was. Once again, thanks to all you veterans for your service. Comments are always welcome!

 

Sink or Swim Time

 

Image from Haley Phelps
on UnSplash.

One necessity I learned when I first began to leave the mirror as a novice cross-dresser and join the world was when I was jumping right into the deep end of the pool. None of that just wearing pantyhose under my pants with no socks when I went out with painted nails. I needed to go all the way with my new wig, clothes and makeup.

It turned out, the biggest problem I faced was there were sharks in the pool I was swimming in. In my case the sharks came in the form of teenaged girls who were battling for their own path to femininity also. It made them overprotective gatekeepers on womanhood and at the same time, seemingly attacking mine by laughing and mocking me. When they bit me, my blood was in the water as they kept coming back for more.

The answer of course was very simple. I needed to become a better gender swimmer if I was ever going to survive and move forward towards my dream of ever living fulltime as a transgender woman. As I became better at my overall presentation in the world as a trans woman, I found the teen-sharks began to ignore me and I could move about freely and relax for a change as I had to change all my muscle memory moves from male to female. I think too, that when I went through my turn in the deep end of the pool decades ago, times were different than they are now. I think regardless of the pushback they are receiving from some backwards adults, kids today are moving towards being more tolerant to the LGBTQ community. At least I hope so.

In my case and point in time I was living when I reached the 1980’s and I was in my thirties I was coming to understand exactly where I was in the gender pool. Instead of trying to get out of the pool when something went wrong, I needed to swim harder against the current to make it. Those were the days when I started to do more than just the easy stereotypical duties a ciswoman is somehow assigned to at birth. For example, I started to do more grocery shopping as a woman as well as starting to do more cleaning around the house. It all was the beginning of a very long swim to experience how much of the feminine lifestyle I wanted and was the grass really greener on their side of the border.

Long story short, I found that a feminine life was more complex and difficult than a man. In most cases, ciswomen were tasked with keeping a family together as well as putting up with all the male drama which came with it. Which ironically, I knew all too well as I had put my second wife through the most profound drama of all. When her husband wanted to be a woman. Somehow, we still lasted twenty-five years until her death because when we were good, we were really good and when we were bad, very bad. Maybe the worst part was when we were very good as man and wife, I was always thinking of how it would be if we could do it wife to wife but just kept it internalized the best I could. The whole process just made me bitter, and I took it out on her. Something I will be forever sorry about.

During this time, I was always very self-destructive as I tried to take my gender feminization frustrations out on myself. Some days, I was moving too fast in my pool and other days (and years) it seemed I was just treading water trying to keep my life afloat. I got to the point that even though I was a success in my business as a male, I would have not wished the rest of my life on my worst enemy. 

It did not happen until I was able to make it out of the deep end of my pool and start doing the activities which really gave me a hint about how women really live. I began to think everything was going to turn out for the best after all. Those years of listening to that little voice in my head telling me to stay in the pool and keep swimming were beginning to pay off. I was paving the way towards a future I had only ever dreamed of. As I swam against the current in the deep end of the pool with the sharks, at the same time, I was earning my own unique form of womanhood, I leaned on other women to do it. Specifically, the ones who had led difficult lives themselves. 

For once in my life, being around my female friends taught me how to survive in the world as just me , as they never once asked or wanted to know anything about my old male life. They went a long way helping me to validate myself again as a person. Something I had never been able or willing to do as a man. Mainly because there was always something missing from my life. 

Being able to swim anywhere I wanted in my pool was certainly a liberating experience and worth the wait. All that swimming did me good and made me a stronger and wiser person. Finding the missing gender link was all I needed to complete my life. It was there all along and I had refused to see it. Maybe I needed a new set of swim goggles so I could see better when I was in the pool. At least that is my excuse for being weak.  

Whatever the case, I managed to make it through all the shark attacks to the transfeminine life I always dreamed of. I hope you can make it to yours too!

Thanks for swimming with me! Comments are always welcomed.

Gender Was Always Such a Delicate Dance

Image from Morgan Petrosky
on UnSplash. 

 I can say one thing with relative certainty as I get started with this post, is that dancing has NEVER been something I have been able to do. I simply have never had the ability to sustain any sort of rhythm when I tried to dance, and I was notorious for stepping on my partner’s toes. 

My efforts became so bad when I grew up that I would only try to dance when I was semi-intoxicated. By now, you may be asking, what does dancing have to do with gender? When I started to think about it, I could equate it this way. At the beginning, I was so insecure as a novice cross-dresser, I was trying too hard to be perfect with my hair, makeup, clothes and movements. It was just like dancing for me as I struggled along with my life. The difference finally came when I discovered that being feminine was something I could learn and did not rely on the sense of rhythm that I needed to dance. For the first time in my life, I needed to go all in to perfect my feminine presentation and accept no shortcuts.

Perhaps you have heard of the term muscle memory. Along the way, I was discovering all that I was doing was changing my muscle memory from being a man to being a woman and it was very frustrating to me. My gender dance was starting off to a bad beginning. Of course, I knew ciswomen moved in their own special ways but to duplicate it was going to be the most difficult dance I ever attempted. 

In the beginning, I was trying just to not look like a linebacker in drag when I cross-dressed and went out. I thought anything would be an instant improvement than what I already was trying to unlearn walking like a man. I also needed to combine it with taking the menacing male scowl off my face and show to the world I was enjoying being there. Why put all that time and effort into applying perfect makeup if I was going to ruin it with a frown on my face. My whole problem was I was going to my own gender dance class without a teacher. The only feedback I ever received came from my second wife when she was coaching me on how to walk in high heels. She rarely wore hers, so I always wondered how she knew.

The final image I was trying to put together, just had to be so much more delicate than anything else I had tried in my life. Which was easier to think about than to do. The only previous cross-dressing images I had to work from were singular efforts on my own to work with my presentation before I was brave enough to sneak out of the house and into the world. It did not matter if I was just going to the mall shopping, or attending a transvestite-transgender mixer, I needed to dance my way in as a transfeminine person the best that I could. 

Initially, I failed more than I succeeded and spent hours trying to figure out how I could improve my presentation in all the ways I could. Since I was battling a severe case of testosterone poisoning from my unwanted male puberty. As I said, it was no fun unlearning the male poses and replacing them with female ones. The best part was that when I succeeded as a novice transgender woman, gender euphoria swept in and carried me away. Letting me know I was on the right gender path in my life. No matter how selfish or painful it seemed at times. The best part was when my new feminine self was coming together, the times I could relax and enjoy the dance. Sometimes, in my heels, I could even feel light on my feet which I had never felt that way before.

The more that I was accepted and then involved with a group of ciswomen who regularly socialized with me, the more I learned about how far I still needed to go to be on an equal footing to mentally dance with them. It was a shock, since throughout my life I had considered myself such an avid student of everything female. Only then to find out I still needed to learn so much more. Such as when to be soft and when to be strong as a woman and to project that to the world when I had to dance with all of it at one time. By myself.

My life as a man in the past taught me at least two ways to deal with the world I needed to change. One of which was to never show any emotion and the second was to internalize any negative thoughts I might run into. Like being able to ever dance with women at all. Overcoming those two obstacles on my gender path were very difficult for me and was especially difficult when I started seriously to pursue a male to female feminization. Way past just putting on a wig, makeup, and a dress all the way to dancing with the world as a trans woman. In fact, I never reclaimed my emotions until I started HRT or gender affirming hormones and to this day I have to still work to not internalize all of my thoughts. Now I know it is OK to show emotion and not internalize everything in life.

One thing is certain; I will never be able to actually dance well in any way shape or form but mentally I can now since my senses have improved so much. Along with my sense of smell and temperature, all the old music I liked so much just sounds better to me now. It is a place I never thought I could be, so I have grown to cherish it. Afterall, gender was always such a delicate place for me since I was forced to a male box at birth I did not want to be in, once I escaped, I never wanted to go back. So far, I haven’t and my dance continues.

I hope you are a better dancer than I am! Thanks for reading along and any comments are always appreciated. 

How Did I Get Here

 

Image from Colton Sturgeon 
on UnSplash.

Often, I sit back and wonder how I ever arrived here as a fulltime transgender woman. Then, the reality of my life comes around and shows me the power of my dreams so long ago.

Some of my dreams I realized and some I did not, which is probably similar to any person’s life. I am biased, but I think a trans woman’s, or transgender man’s life is sufficiently different from most of the population to be mentioned. I think that very few boys' most prominent dream of what they wanted to be when they grew up was NOT a woman. Mine was. Even though I was into sports completely, I did not have any dreams of advancing into upper-level competition when all I wanted was to be one of the pretty cheerleaders on the sidelines. 

I wanted to be a girl so bad with their pretty dresses and long hair, I even dreamed about being a girl in my dreams and was extremely disappointed when I had to go back to my old boring male life. I just hoped that someday I could find my way out of the closet I had built for myself. On the other hand, I thought just maybe I would outgrow my gender dysphoria when in fact, what happened was I grew into it. As the years began to fly by, my skill at makeup and dressing myself in feminine clothes became better with time. 

What did not become better with time was me being able to sneak out of the house and away from the mirror which lied to me about my appearance and head out into the public’s eye. When I was out in my new high heels trying my best to look natural everywhere I went, I kept asking myself how I got here and why would I want to leave all the male privileges I earned along the way behind me. Mainly the natural defense that most men have simply because they are males in the world. If I was harassed for being my new transfeminine self, what would I do? Luckily the worst harassment I ever received was being laughed at early on and later having the police called on me for using the women’s restroom. I simply retreated quickly to my cross-dressing drawing board to become better as a novice trans woman and the female cop who answered my call just told me to go on my way. No harm to either except to my frail feminine ego. 

I keep writing about my failures in life because as humans we all have them and when we do,we need to pick ourselves back up and learn from them. When I faced my biggest obstacles, I needed to understand in the worst way that I really wanted to be in the new exciting yet scary life I was in, but how much was I going to give up continuing it. Building parallel successful binary gender lives was not the long term way to go. In the end, one had to go. 

The best I could do then was stay out in the world of ciswomen and see if I could make it on my own. It meant attempting to experience the good and the bad of a woman’s life to see if I could earn my way across the gender border into my own version of transgender womanhood. During this time, I did the best I could to establish myself as a totally new person, which meant leaving any vestiges of my male life behind to total strangers. There was no time for me to consider how I got there when I was interacting with the public. Again, I was fortunate in that most of the world was accepting to me and my problems were rare. 

I found myself at a point where I never thought I could be and that was being able to live a quality life across the gender border and being able to be shown the way behind the magical gender curtain I always wanted. Once I got there, my final answer was no surprise. I never wanted to go back to my old male life. Then it was up to me to figure out what to do about all the leftover male baggage I had accumulated over the years. 

As I was figuring all this out, it never occurred to me to consider how I got to such a different point in my life. Afterall, how many other humans have the chance to live such a unique life seeing the world from both sides of the main binary genders. It was not until then did I begin to enjoy where I was in life and the challenge of building a new one. Taking a life down and building a new one is certainly not for a weak person and not becoming a victim when you are down is a key to success to figuring out how you got here. 

Even today, as I prepare for a big dinner out with spiritual friends tonight and I am putting together an outfit, it still feels slightly different for me. For the dinner, we are supposed to bring an object or picture from a departed loved one and I chose the picture I recently found of my dad in 1951 with his dog. Since I have long since made peace with my mom who I tried to come out to when I got out of the Army, I never did try to come out to dad. Looking back, maybe I tried the wrong person, and I blame myself for never giving him the chance to know his daughter. Now this is as close as I can come to letting him know how I got here. Maybe too, since I have had the chance to live my transgender dream as long as I have, I would have been in a better place to explain it to dad. His death took that away from me sadly.

I hope you are on the path to discovering your place in the world. Thanks for experiencing mine. Comments are always appreciated!

Constant Refinement of Life as a Trans Woman

Image from JJ Jordan
on UnSplash. 

 Proper presenting as a woman has always been a challenge for me. After I went through an unwanted male puberty into an equally resented manhood, I emerged with no real feminine characteristics to work with. So, I had to begin from ground zero on my path to my own unique form of womanhood. 

When I could still find some of mom’s clothes I could fit into, the mystery of applying her makeup kept me working towards mastering it for a very long time. Until I could get to a point where I did not look like a circus clown in drag. Even if I was in despair over my cosmetic progress, I was able to keep working on it until I became more proficient in what I was trying to do. I did not know it at the time, but I was facing decades of constant refinement to get the feminine image I wanted to show the public correct. 

When my cross-dressing habits took me out of my closet, I was really put to the test when I first went out into the world. That is when I discovered how far I needed to go to be successful as a novice cross dresser. At times, the whole feminine process seemed impossible for me to do. But, for some deep reason I did not fully understand, I kept going. I even went the extra mile as a kid to take on a rural newspaper route to make extra money to buy what clothes, panty hose and makeup I gathered the courage to buy on my own. It all worked together to give me an added sense of accomplishment in my refinement process. 

When I had the courage for the first time to go shopping in one of the big indoor malls close to my house, I used to gauge my progress on how much attention I got from the roaming bands of teen girls in the mall. I instantly knew my refinement was working when I went from being noticed and laughed at all the way to blending in with the other ciswomen and not noticed at all. Still, it was no more than a beginning, and I had no way of knowing how long and winding my path would be across the gender border. 

Coming up with the credentials to cross the border into a woman’s world, took quite the refinement process for me. I researched as much as I could the transgender women that I knew who had already made the crossing as I wondered what made them successful other than their appearance. Which was amazing. I knew the old “beauty was more than skin deep” applied to these trans women and I wanted to know more. As I was deeply questioning my future in their world. What would I do about the relationship I had with my second wife and child as well as how would I continue to support myself in a totally new life were the major questions I had. At that point, refinement meant to me I needed to research how the other trans women I admired changed their lives and could I do it also. 

As I researched the trans women I knew and admired, I learned the truth that there could be no shortcuts for me if I ever hoped to overcome the obstacles I faced on my uniquely personal male to female feminization journey. Every wall I faced, I would have to climb it rather than look for the easy way around it which simply did not exist. I started from point zero and had made it to a middle point which I discovered was more interesting than I ever thought it could be as I went from being a dedicated student of ciswomen to being allowed behind the gender curtain to see the real complexities of the life I wanted to live. Still, I faced my own insecurities about doing it and needed to rely on my inner voice to keep me going. It kept saying that somehow, I was doing the right thing, no matter how difficult it felt.

When I arrived at this part of my life, I again out of necessity had to really begin to decide what I was going to do about my future and take the next step towards refinement so I could do it. Unexpectedly, I was able to carve out a new transfeminine life faster than I thought. Which brought in communication skills as well as other things such as settling into wearing the same wig and using the same name because the same people were interacting with me and I had to become a solid person. Not just a memory which kept on changing. Constant refinement was slowing down into areas which I could control. All of a sudden, my dream of womanhood on my own terms seemed like a real possibility. Which scared me in some ways and excited me in others. I could control for a change where I was going because I was a regular there and I even thought I was the venue’s token trans person because I was a tribute to their diversity. 

When I discovered I could make new women friends who accepted me for who I really was, I was able to refine myself simply by learning from them. They led and I followed their example which rounded off the remaining rough edges I had from a male life. Most importantly, the lesbian women around me taught me that I did not need a man to validate my existence. Which worked out well for me because the vast majority of cismen ignored me when I left their club and all my male privileges behind.

I think now, in the long term, the life I led which resulted in my constant refinement presented me with the chance to have a much more interesting life than the normal human. 

Thanks for reading along! And I hope the election turned out as well for you as it did for me. We now have a Democratic Senator and Governor in my native Ohio! Yay!

 

Happy Halloween !!!

JJ Hart with Tom on left. 

 Once again, the national holiday for cross dressers has rolled around. It is our chance to show off our feminine finest to the world without the fear of destroying everything we had tried to build up in our male lives. In many ways, for some of us, it is time to walk that thin line of appearing too convincing as a woman and raising suspicion of how we were able to go all the way and shave our legs for one night, or have the skill to apply our own makeup. 

Over the past month, I have presented the various Halloween parties I attended which really helped me to understand if I could ever live my dream as a transgender woman. I was fortunate in that I was able to be free enough to take the Halloween opportunity as far as I could and run with it. My wives at the time all knew about me being a cross dresser, so my skill at putting together a complete feminine “costume” did not surprise them and they stayed out of my way for the most part.

The only problem I had with Halloween was that it only came once a year and I needed to find other outlets for my desires during the regular boring parts of the year. When I needed to escape the part of my life I wanted less and less to do with. 

Sadly, after I transitioned and crossed the gender border into the feminine world, my interest in Halloween began to fade. It was as if it had served its purpose and it was time for me to move on with my life. The exceptions were the Greater Cincinnati Witches Balls that my future wife Liz and I attended every year. In its early stages, the Ball was held in a vintage mansion which at one point in time went under a renovation which included an attached ballroom with a balcony which was perfect for the vendors who set up to try to sell their wares. In other rooms, there were belly dancers and various other entertainers. It was quite the event. 

In the early years, the only mistake I made was the footwear I chose for the party. I found out quickly that no matter how good my high heels made my legs look in the mini-skirt I was wearing, my feet just did not agree with me wearing them and the pain led me to places I could sit down and kick off my shoes for a couple of minutes. I learned my lesson in the later years when we went to the party.  I  wore comfortable flats which made it easier to walk the short distance to our close-by hotel room we had so neither of us had to worry about drinking and driving. 

Liz and I became so attached to the workings of the Witches Ball that in later years we even became volunteers through the circle of spiritual friends that Liz had been a member of for years and they accepted me also. The image I provided with this post shows me helping out at the circle’s promotional table with another volunteer who has since passed away. It was nearly the end of any more Halloween activities I could be involved in as my mobility issues worsened. In the meantime, I was left with all the pleasant memories of Halloween past.

I Hit the Kid Lottery

 

Liz on left JJ Hart with Daughter
on right. 

One person I don’t mention enough is my daughter who is my only child. The easiest thing I can say about her is that somehow, I won the kid lottery when she was born. 

To begin with, when my daughter came along, I was very much an out of control, alcoholic wreck of a person. Desperately running from my gender dysphoric problems. Very quickly, I needed to settle down and at the least figure out a way to pay for her birth on the close to minimum wage job I was working at a small local radio station. So, you could say, she worked her magic on me before she was even born. Since back in those days, it was more difficult to determine the sex of your baby ahead of birth, my wife and I decided to be surprised when she arrived in the world and more than anything else we wanted a healthy baby.

Not only were we blessed with a healthy baby, I became what I treasured most…a girl dad. I was secretly overjoyed that I would have the chance to be around another feminine person in my life and if I ever had to come out to her as my authentic self, it would be easier to do with a girl than a boy. 

As she grew up to college age, her mom and I were divorced and my daughter ended up growing up in a village who adored her but more importantly shaped her into a very diverse person. Which would obviously come back to help me later with her. The only drawbacks to her diversity came from my mom who wanted to control where she went to school which I would not allow. 

Jumping ahead to when I finally came out of my closet and announced to the world that I was transgender, my kid was chosen as being the first to know. I was very nervous on the morning that I chose to tell her the news, and I was frightened at her possible response. It turned out she was disappointed but not in the way I thought. It was not in the fact she was essentially losing her father figure but on the other hand, why was she the last to know. Then I had to tell her she was the first to know I was transgender. Not a cross dresser such as her mom and stepmom knew that I was. It was a huge difference, and she started to calm down and to my amazement began to make plans to help me along with my transition across the gender border. I knew right then I had won the kid lottery and all the effort I put into raising her for this moment had paid off. 

The first suggestion that she made was asking if she needed to come shopping with me. Which I politely declined since I was able to fill out my wardrobe nicely by then since I was a serious cross dresser for so long. The second suggestion she made scared me to death. She volunteered to treat me on my upcoming birthday to a hair color and styling at her upscale beauty salon and spa. Like I said, the whole idea frightened me but I did take her up on the offer and in a couple of weeks, there I was in the salon nervously walking down a line of ciswomen getting their hair done. After the nerves wore off, I discovered my day was the gift of a lifetime and I understood then what the drawing card was for all women everywhere. In fact, I joked about not needing to take my Estradiol dose that day because the estrogen in the air was so thick I could cut it. On my way out, I set up my next appointment without the help of my daughter. 

Her influence on me did not end at the salon as she worked with me setting up a new legal name which would work easily for her three young children and made it clear she wanted me in their lives. It turned out, I was in a humorous way when my middle grandson ended up in a fourth-grade class taught by one of the cities’ best known out drag queens. My grandson came home one day and proudly announced to my daughter that his teacher and I were just alike, and my kid had to explain the differences between a drag queen and a transgender woman to her fourth grader. It turned out to be the first of many conversations she would have with her kids about diversity in the genders when her oldest daughter came home suggesting she liked girls more than boys. That was the daughter who graduated as a nuclear engineer from Ohio State and then transitioned.  It turned transgender women and transgender men run in the family. 

Later on, it turned out my daughter and son-in-law stepped up in a big way when I needed them again after the breakup between my only sibling and I when I came out to him as transgender. It was around Thanksgiving and he revoked his invitation to me to come enjoy the family. Back then my future wife Liz and I were just getting serious, and it looked like I was going to have no family to visit on the holiday like I was used to. Liz and my daughter stepped up in a big way and invited me to their family’s holiday get together. It meant the world to me.

It proved to me once again that somehow, someone was looking after me and I had won the kid lottery. I even was asked to speak and participate in my grandchildren’s Bar-Mitzvahs when she converted to Judaism. Again, I was scared to death to get up in front of a bunch of strangers I did not know except for a couple of women I knew from before I transitioned and even went along on a girl’s night out trip to a drag show with my daughter. 

Whatever the outcome of my life now, my daughter was certainly a gift which kept on giving. 

As always, thanks for joining in with my thoughts. Any comments are always appreciated!

Starting All Over Again as a Trans Woman

JJ Hart

With all the environmental global warming disasters we have going on in the world today, there are many people forced to start their lives over. My heartfelt sympathy goes out to all of you who have lost a significant part of your lives to weather-related incidents.

On the other hand, transgender women and transgender men have a head start on most people because we have become skilled in stopping our lives and starting all over again. In my case, I put it off until my mid fifties to start all over again and leave my male past behind me. The only thing I really did was build up too much male baggage I had to figure out what to do with.

I had a long-term marriage to a wife who was completely against any thoughts of me transitioning into a woman, a small but secure family, a vintage brick house I was restoring and a good job to consider losing. Unlike a weather related “hand of god” experience, I was bringing down the demise of my male life completely on my own. Without the help of anyone else. So, it would be my burden to carry around if anything went wrong with me crossing the gender border and following an extreme male to female femininization program which would eventually include HRT gender affirming hormones.

The only thing I did know was I was off to a good start as I slowly refined my makeup and clothing arts as a very serious cross-dresser who always had the suspicion that more than cross-dressing was in my future. Being more than a cross-dresser was like dangling a carrot in front of a horse to get it to move, I just had to have the confidence to tear down what I built and start all over. Any setbacks I encountered when I went out in public for the first time would always destroy the frail confidence, I had built up in myself over time and sent me back to my closet to try to figure out what I was doing wrong. How hard could it be?

I found out over my early years that “it” could be very hard as I struggled to get out of my closet and into the world. For the most part, it seemed I had bitten off more than I could chew when I began to get close to the gender border and had to think of all the white male privileges I would have to give up if my urge to transition did not change. Not only did it not change, but it also strengthened into a powerful force that I thought of every spare moment of the day and even some nights when I dreamed. It was always extra punishment when I had to wake up from being an attractive woman and go back to my boring and unwanted male world. Still, I had no alternative but to keep pushing towards a transfeminine goal I never knew if I could reach.

To my surprise, I went through other major and minor transitions as I made my way from cross-dresser to the transgender terminology. As I became more skilled at blending in with the world of ciswomen around me, mentally I slowly shifted back to my old thoughts that I wanted to be more than a man who looked like a woman. I wanted to feel as close as I could to feeling like I belonged behind the gender curtain and be allowed into the girls’ club full-time. All my surprises led me to a place where I could finally flourish as a trans woman. If I could decide what I was willing to give up getting there. When the time came to decide, would I be willing to push all my chips into the middle of the table and decide to go all the way, or once again, slink back again to my closet. Or I could relate my life to being one big “Monopoly” game where I was always ready to take another chance and buy another feminine property.

I know all of this sounds like sort of a word salad fantasy until reality set in for me. In my haste to seek out the meaning of a feminine existence for me, I had started to build up the basics I would need to keep building a new and exciting life I never thought I could get to. But there I was having to decide what I was going to try to keep of my old male life as I tore it all down and built a new one. I was very one dimensional in my life with my hobbies and interests so in that sense, I did not have much to get rid of. The one interest I hoped I could keep was my interest in sports and always figured it might help me if I was ever involved with a man but never dreamed my former male life in sports could mesh so well with the ciswomen I met.

Before I knew it, I was joining woman-friends in sports bars drinking beer and debating our favorite teams. I saved one piece of male baggage but at the same time, others had to go. As I write about often, I lost my unapproving wife and several male friends to death in a short period of time. When they left me, I realized how difficult it was for me to make true male friends. As I started to transition more, I began to understand why. Down deep, I was never interacting with other men as a man but rather as the trans woman I truly was. All of the pieces of the puzzle of my life were finally starting to come together, and I was seeing the big picture of what my denial of myself had cost me over all those years. I came away thinking how I could miss something that was that simple.

One thing was for sure, thanks to the HRT hormones and the relationship I was building with my future wife Liz, nothing was standing in my way on my gender path. Liz was the opposite of my second wife and told me she had never seen anything but female in me anyhow. I certainly was not one to argue and gave away all my male clothes to charity so I could help all those thrift stores which had helped me in the past.

I was more than ready to start all over again.

Thank you so much for taking your time to join me in my gender travels. Any comments are always appreciated.

 

 

Destiny or Blind Luck

 

Image from Maia I on 
UnSplash.

As I mention often, escaping the restrictive male box I was born into turned out to be not an easy task. So difficult that I wonder how I ever made it and consider if destiny or luck was involved.

Since my life was laid out for me in what I was supposed to do with my male privilege, the choice to be a female was not included. I was expected to grow up, be intelligent enough to go to college and marry another woman from the college I was attending and help the family’s genetic pool flourish. Not much of that happened as I did go to college but never met the girl of my dreams enough to want to spend the rest of my life with. In fact, I had the sneaking suspicion the only woman I wanted to spend that much time with was me. Several obstacles were stopping me such as the male box I was in and my problems escaping it.

It turned out, the only serious feminine relationships I had were my form of the gay term “beards”. I just needed a ciswoman by my side to convince the world that somehow, I was “normal.” The same way some gay men use a wife and kids to somehow hide their true selves from the world, I was doing the same thing. Over the years, I discovered that was not so much the case because I was learning I just liked being around women much more than men. So, it was more of a destiny sort of thing coming through as I would realize later as I went through my male to female femininization transition.

Just using the femininization term might be wrong because I was just expressing what I had always known about myself but could not bring myself to express. All I needed to do was refine the process of how I was ever going to achieve the goal of living full-time as a transfeminine person. Far from the casual cross-dresser I was lying to myself that I was. That was when I went through another major gender transition. As I mentally moved away from my cross-dressing mentality, back to an idea I had so long ago when I was admiring myself in a mirror at home in dress and makeup. I thought then this was fine, but there had to be so much more. As in me being a girl myself.

For the longest time, I went through differing stages of emotion all the way to a self-pity form of being a victim to a problem that I knew little about and felt that I was the only boy in the world that wanted to be a girl. Then along came the world of computers and social media and the world opened to me that I was far from the only pseudo male who wanted to be a ciswoman and did not care what it took to get there. I quickly discovered too, by going to “Tri-Ess” mixer/socials that I was not going to find my answer there either. I did not find that magic friend that I could talk about my gender secrets with because everyone I met was not enough woman for me, or too much when it came to the rare transsexuals in the room.

I did what I always had done, I went back to my own feminine drawing board and at the same time continued to be an intense student of every woman around me. Destiny, not luck was driving me forward in a single-handed pursuit of my unique womanhood. The problem was I became a very selfish person with only a couple goals in mind. Advance my femininization process and, at the same time, advance in my job so I can finance it. I knew for sure destiny had me a comfortable seat on a runaway train and I just had to make the best of it. Another obstacle which kept popping up in my way was the fact I could never make it across the gender border and behind the so-called sacred gender curtain without help from my destiny. My wife said it best when she called me a terrible woman and it had nothing to do with how I looked. The fact was that I still had years of socialization to go through before I could truly say I did not make a terrible woman and she was wrong.

I thought that since I was “making” something, I better do a good job at it. Since very few humans have the chance to stop their old life and start all over again. Except that was not entirely true as I began to think about it, destiny and being female was always apart of me. I just did not know how to express it. It turned out to be on me to learn to express myself the way I needed to be to do more than survive in the world I was in, I wanted to thrive as a transgender woman. A world I was in a rush to learn as much as I could to experience. My woman was always living rent free in my head and wanted more, and I was ready to give her more access.

With extra access, my life became easier to live as I was able to feel comfortable in my new feminine life. My vision of destiny became easier to understand too as there was no luck with what I was doing. I had earned every bit of my progress by living it and it all felt so normal. Sure, as I always point out, there were many obstacles in my way. Including a strong constant denial coming from my old declining male self. Who was a “self” in title only as all his male privileges were slipping away. I had good teachers who taught me where my true validation in life should be from…myself, especially from other cismen who were resentful that I had left their club.

I had claimed my freedom from their club, and what I always wanted to do was claim my destiny. There was no luck with it.

 

 

 

 

Seeing It All Clearly Now

 

Image from Lola Rose
on UnSplash. 

As I journeyed for years along my decades old gender path, I discovered I could see life much more clearly.

Going back and forth across the gender border from male to female allowed me to see what goes on in the lives of both binary genders. Something that is very rarely accomplished by very many human beings who are stuck in their restrictive gender boxes from birth. But, what about the rest of us who for some reason, got put into the wrong box and were forced to live a life we never wanted until we went out on our own to change it. That is where we start to see the changes in our gender set in. Or maybe something was wrong when we were put into neat little boxes at birth.

In a classic what goes around, comes around, we go around searching for our authentic selves as transgender women or transgender men until if we are lucky, it comes around back to discovering our true selves later in life. How we can come to that conclusion is as different as human beings can possibly be. Some of us take shorter routes than others. If I use myself as an example, I took decades to come to my gender truth that I was hiding from me the whole time. If I had the courage to face my truth earlier, my life would have been so much different. I am sure it would not have been a completely positive experience, but at least, I would have been working towards living a transfeminine life much earlier than I did as a serious cross-dresser.

I was the classic person who does not see the forest for the trees. Since all my trees had a big transgender marked in every one of them and I thought it could not be for me. Even though I was going as far as cross-dressing three out of the seven days of the week if I could get away with it.

At the least, during those three days of the week, I was learning to present better in the world the way I always wanted to. As I did it, slowly I was seeing what I needed to know if I had what it takes to cross the gender border for good and would the grass be even greener when I did it. Plus, as I always mention, I had an increasingly successful male life and family to deal with. At the least, my second wife knew about and reluctantly approved of my cross-dressing but always drew the line if I was thinking about going ahead with the next step for me. Which would have been HRT-gender affirming hormones. She always said she did not sign up to live with another woman, and I never had the courage to tell her she already did. In the meantime, I clashed with my two main ciswoman role models, my mom and my second wife. I admired them for being strong women until it came to the times, they did not accept me.

The problem was I was seeing clearly the trans person I was becoming and every positive step I took led me to believe I never wanted to go back to the male life I never asked for. Most importantly, I was building the confidence to do it and ignore the gatekeepers like my wife and mom. I felt deep down, if I kept knocking on the gatekeeper’s door, someone would let me in, and I could experience for myself what went on behind the gender curtain.

When I finally made it behind the curtain, I found the feminine reality I was always looking for. Far past the shiny fashion, hair and makeup intangibles all the way into the complex lives that ciswomen lead. By that time, I had paid plenty of dues to get there and just figured my socialization as a woman was part of life I should cherish. If anyone wanted to get in my way, shame on them because by that time I could see clearly who I really was in my unique form of womanhood. Other women saw me too when I was asked to pose for a book about different women for a judging in Chicago years ago. It was to be my only experience as a photographer’s model, and I was nervous, but I enjoyed the attention immensely.

The rest of my life was not as exciting as posing for a photographer, but in other ways, as satisfying also. I was enjoying building new acquaintances with my wife Liz as we went to writers and crafters meetup groups to intermix with total strangers. The whole experience helped to get me out of my shell and lift the fog away from whom I was destined to be in life. Most importantly, I was happy doing it. Something I was never allowed to do when I was growing up when doing good was not good enough, there always had to be something better. I never imagined how much that carried over into my adult life until I began to come out of my gender shell. Even still, I had to work my way out of the idea that there always was a better dress or wig I could buy which would magically transform me into an attractive passable woman.  It was all good until I looked in the mirror or went out into the world attempting to be myself. Some nights being myself was within reach and some nights it just was not and I needed to go back home disappointed.

I went back to my gender drawing board continually until I slowly got it right and began to present myself in the way as the trans woman, I wanted to be.  I took advantage of all the time that I wanted to see the best woman I could become on my own terms. It was the best I could do. I was done with all the denial I had put myself through which should be the topic of another blog post.

Speaking of another post, I always invite you to join me again and read along. Thank you! 

Comments are always welcomed. 

 

 

 

 

 

 

 

 

 

 

Putting Yourself Out There as a Trans Girl

 

Image from Sasun Bughdarian
on UnSplash.

Putting myself out there in public was probably the hardest thing I ever have done in my life.

Most of the time I was in a high-risk-high reward situation as I tried and failed miserably at presenting myself in public as a novice transgender woman. I kept on working until I put myself into the low risk-high reward category when I finally was able to pass reasonably in the world I discovered was run by ciswomen if I ever wanted to succeed. I was so far away from the world of cross-dressing/transgender parties and socials I kept going to, I was learning so much more every time I did it. I was on thin ice on my gender path and I knew it. I just hoped the ice would hold my weight. Even though I was on a crash diet to be able to purchase more fashionable clothes and look better. It was questionable. 

All along, I knew there was no way I could go halfway and make it to my dream of living fulltime as a transfeminine person. Trying to live a life stuck between two genders was no way for a person to live and when I did, the gap between the two genders was too much to overcome. My mental health suffered and I was very self-destructive and had to do something about it. The last thing I wanted to happen was that my gender dysphoria would doom my life as I knew it.

In the meantime, I did the only thing I knew how to do which was continuing to hide my cross-dressing from the world behind a wall of male macho intentions. Again, it was so hard to hide my truth that much later in life I was surprised that no one had guessed my dirty little secret when I finally cracked my gender egg and made it out of my closet for good. Another problem happened as I had to keep building a successful male life, I never wanted, I knew some day soon I would have to tear it all down and start all over again. Internalizing and putting that day off, just hurt me more as I continued to put myself out in the public’s eye.

By doing so, my risk situations leveled out to a point where they almost balanced each other. I was in the ultimate high-risk situation of losing essentially my whole life but at the same time conquering the higher risk of being able to carve out a new and exciting feminine life from scratch. It seemed to me that every corner I went around on my new path had different obstacles to take on as I was intimidated by the complexities of the ciswoman’s world I so badly wanted to live in. As I left the male world I wanted nothing to do with, it seemed nothing was easy to do as I had to learn everything I could quickly if I ever wanted to survive. The worst part of it was, I wanted just to keep running back to the privilege of the male life I had given up but just could not.

So, I kept putting myself out there to make a lot of bad mistakes on the way to my own form of womanhood. Like ruining hours of prep time getting ready to go out, only to discover I was moving like a linebacker in drag when I did it. Or the time when I had everything down when I went out and promptly got my heel stuck in a sidewalk crack and almost fell down. I made it to the point of being so paranoid about going out, I kept on wondering if I would ever be able to put my feminine self in motion for the world. Even though it was difficult to do, I kept forcing myself back out and getting better in my overall presentation. Making it less of a high risk that I could do it. Since I had already been laughed out of venues in the past, what was the worst that could happen to me.

Ironically, my path took me another direction right into the worse than could happen experience when I was almost molested by two men when I was alone on a dark city street and I was lucky to get out of it by giving them my last five dollar bill. It was too close for comfort for me, and I almost learned the hard way what ciswomen are raised to know about the dangers of toxic men. I started to always plan to ask for a transgender man friend to walk me to my car after that. I know I mention that experience a lot but it is my way of always warning you that when you go behind the gender curtain and transition, you lose your male privilege of personal security so be careful when you go out because it is certainly a different world for a trans woman.

For years, I kind of just drifted along in the female world learning what I could to increase my knowledge until I learned too much and found I could never go back to the male life I had before. Almost all the risk on not doing it suddenly became extremely shallow to me as the why’s I should not transition started to fade. I had put so much time and effort into my womanhood, what I was waiting for.

I had even survived the worst moments of my male life when almost everyone around me passed away, leaving me tragically lonely and sad. The only bright light I had to fall back on was the knowledge that my strong feminine self was always there for me and it would be extremely low risk to reach out and ask for her help. Even to the point of helping me find a new social circle to hang out with.

I stepped out of my dark closet again and was fortunate to find a small circle of diverse friends I could socialize with and even grow into my new HRT hormonal changes with. I stepped out of my social box and utilized the so-called straight venues I was already a regular in, along with a transgender woman friend of mine and against all odds found new friends who all happened to be lesbians. From there, I even took the risk of going online to the trashy dating sites and tried my hand at attracting someone else. At that point, what did I have to lose. After a very low-risk, high gain deal, my future wife of over fourteen years contacted me. We clicked and have been together ever since, so I am still enjoying the results of my low risk move. But I must stress, none of that success would have been possible without my determination to put myself out there and try.

Certainly, I failed quite a bit, but from failure came learning and I made it thank goodness.

As always! Thanks for reading along and all of your comments are welcome.

 

 

More Than Just a Passing Fantasy

 

Image from Alexsy Turenkov
on UnSplash.

As I made my way into the public’s eye as a novice transgender woman, I needed to prove to the average person I was much more than a man in a dress with a wig and makeup.

It meant I needed to change my entire thought pattern too about who I thought I was because for the longest time, I considered myself more or less a feminine “hobbyist” who dabbled in wearing feminine clothes and makeup. I considered myself as serious about my hobby as much as I did my brother being serious about his golf game.

Ironically, I can not put my finger on the exact moment I started to change my overall thoughts on myself, but it was a gradual process. Triggered by me being exposed to the transgender term for the first time in my life. It all came from the fact that I knew there just had to be more to what I was doing with my feminine self than just a casual process and the transgender terminology appealed to me. Being trans took me another step towards living my ultimate dream of living as a transfeminine person more than anything I had ever read before.

All my research into gender dysphoria and its effects on me led me to slide myself increasingly on the gender scale to the feminine side of the spectrum internally. Which was the easier part initially. Then, all I needed to do was internalize my feelings and keep on living my male life so no one would notice that I was different at all. The problem was, I did not know how much internalizing my gender dysphoria would hurt me in the short and long term.

As I always knew, but tried to hide, just cross-dressing was never going to be enough for me, as I wanted to do more with my life as a woman. Of course, once I realized it, I needed to plan a course to do something about it. Being stuck in a restrictive single occupant closet was not going to be enough. Somehow, I needed to gather the two C’s, courage and confidence to take on the world as my authentic feminine self if I was ever going to do more than jut survive in the male world I wanted nothing to do with. I needed to get out of it and convince others I was so much more than some sort of a drag queen playing a part of a woman.

Little did I know, the drag queen problem would take care of itself everywhere but in the gay venues I was going to often. After I was done hitting my head against the wall in the gay venues, I decided to go back into the world once again to see if I could be viewed than more than someone’s fantasy object. Accomplishing it became easier to me than I ever thought possible when all I had to do was to keep going back to the venues I had frequented as a man but this time as a trans woman. If I managed to wear the same wig and look the same, I was hard to miss and easy to remember if I followed my basics of always being pleasant, never causing problems and tipping well. By doing so, I became a regular before I knew it and I started to carve out a whole new feminine life away from my male past. Most importantly, there were no passing fantasies involved for me, no smoke and mirrors as I was actually doing it.

I continued to take my trans show on the road, so to speak, as I tried to live every spare moment as a woman to see if my dreams were more than just dreams and not turn out to be nightmares. I was trying to make sure I had all my life’s basics covered if I was ever going to give up everything I had earned as a man. Use what I could as a transgender woman and start all over again. That way, I would not totally be starting over, I could take what I learned as a so-called cisman and apply it all towards the scary but exciting new world I was living in.

Doing the same things over and over as a woman helped me to carve out the new life I had always wanted to live. Other ciswomen knew my name and wanted to know more about my life because they were curious why I wanted into their world. I was in heaven and continued to want more as my life changed for the better. It all did because I had the courage to put myself out in the public’s eye. While I never managed to be the most attractive woman in the room, I was the most consistent with my look. Which was all I could do with what I had to work with in my testosterone poisoned body. It took me a lot of time and effort, but I put away all my old misgivings about my life’s journey and kept my momentum up towards my extreme male to female femininization project.

By this time, most all the family and friends who meant anything to me had passed away leaving me all alone in the world to do what I wanted. After all those years of playing around with thinking I was a casual cross-dresser had completely left my mind and looking like a woman was much more than a mere fantasy, I was ready to move forward into the world I had always should have been a part of. It turned out to be a for better or for worse deal for me by this time. I had put so much effort into the struggle to femininize myself and get out of the male world that it all turned out for the better as I entered a win-win situation in the world.

In fact, during my life, there was no way I ever could have fantasized arriving in the place where I had arrived. I love it when a plan comes together. Even though it took me so long.

Thanks for reading along with all my hopes and desires during my life.

Thought are always appreciated!