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!

 

Election Day and Much More

Image from 
the Smithsonian

It is election day and my anxiety is at an all-time high it seems. On one hand I am excited to go out and place my vote and on the other, I am scared to death the final results will give us more of the same we have had to put up with as transgender women and transgender men wherever we are. If you are at all a regular reader of mine, you know where I stand with my politics and I am very much against the “Diaper Don” and Elon Musks of the world who have tried to buy elections. Especially in my native state of Ohio. I am so sick of the anti-transgender political commercials I see lying about us in the world. I cannot wait for it to be over. The only thing I urge you to do is look ahead at your future and the future of young trans kids everywhere. Even if you are a closeted cross dresser right now, you never know what the future may bring for you and you may need the rights you voted for. 

On the other hand, it is time for me to remember the first time I proudly showed my new female driver’s license to vote. It was a true milestone in my life that I will never forget. It was as if I was knocking out two birds with one stone by exercising my right to vote as an American and as a transgender woman. Hopefully, after this election, the people will come around to the truth and vote for no more useless wars and honest politicians who care about us. I would only urge you to get out and vote for the future of this country and to release the bonds we feel every election day as trans women and men.

The “more” portion of this post pertains to the fact I have still not heard anything back from the cardiologist at the Veterans Administration which I hope goes under the category that no news is good news, but I will see. The latest EKG I took showed some sort of problem my doctor wanted to look at. Now, my biggest fear is that I will have to stop taking my estradiol dosage I have been on for years. I have received a comment from another reader approximately my age who needed to stop her hormones quickly when she was diagnosed with heart problems. Being me, I immediately became concerned what would happen if I too was told I needed to stop my hormones. Would I lose the long hair I have taken years to grow, go back to having male emotions and certainly lose my soft skin and breasts were all primary fears. Then, for once I calmed down and told myself not to build any bridges until I came to them and if I did stop, whatever happens would be far better than losing my life.

Plus, anyway I look at it, I need to be grateful I was approved for HRT to start with and deep down I knew I could be on borrowed time if I took them. At the least, even if I need to stop tomorrow, I would be deeply disappointed but appreciative of the chance to take an exciting hormonal ride across the gender border I was traveling. It is just a negative part of my personality to build such huge bridges along my life’s path. 

Speaking of my path, ironically as I enter my late seventies, the biggest obstacles I face seem to be medical ones. On top of my heart concerns, I have an appointment with my hematologist coming up soon also at the VA. Since it is at the downtown hospital, it is very congested and hard to get to, so thanks to my wife Liz, she can pull up to the front door, drop me off and go find a parking spot. It will be another we will see appointment because all my blood lab work has been done for the doctor to look at. 

This will be a short post today as I have to get ready to dress casually and go vote. A close shave, followed by a light foundation covering and lipstick should do it for my face. While leggings, and my “Boomer” sweatshirt would do it for my fashion on an unseasonably warm Ohio night in Cincinnati. Even though I want and expect to see a larger than normal turnout, selfishly I hope I do not have to stand in line long because of my mobility issues. Whatever the case, I will have to make it because I desperately want my vote to count. 

As always, thanks for reading along! I hope your day finds you healthy and happy. Comments are always welcome.

 

No Learning Experience is a Waste of Time

 

Image from Christian Lue
on UnSplash.

Now that Halloween has come and gone, I am sure that some of you took advantage of the freedom of the season to express your feminine side. Maybe to the public for the first time. 

For you first timers, congratulations on taking the first tentative steps out of your gender closet. For the rest of you, you ended up like me and gained Halloween experiences as a trans woman you will never forget. I vividly remember the night that three friends and I attended a midnight showing of the “Phantom of the Opera” on Halloween one year in the newly restored “Ohio Theatre” in Columbus, Ohio. I was proud of my “costume” which was a mini dress, blond wig, shaved legs and high heels to set it all off. I was prepared to pay the price for fashion with my heels until I had to walk a distance to the theatre from the closest parking spot we could find. As I tried to daintily find my way down the sidewalk, it was not long until my feet were protesting and I was looking for a place to sit down. That was not happening and I just had to ignore the pain and chalk it up to another experience.

When I began to break away from just going out into the public eye and testing myself as a novice cross dresser or trans woman, I needed to get ready for many more experiences, some good, some bad. From both, I tried to keep in mind how difficult it was going to be to attempt to cross the gender border and live out my dream and I tried to always learn from the experiences I was going through. Since I had very few to none natural feminine characteristics to start from, I knew my journey to possible success as a transfeminine person would be a long one and hopefully soon, all the tears from the rejection I was feeling would soon be forgotten. Sadly, that was not the case and some of my early dealings with the world have left many serious memories with me. Until I got to the point of dealing with them as just another experience I would have to go through to get to my goal. 

I was there, mainly because I was always on the outside, looking in when it came to being around the ciswomen in my world. Because I was excluded from the exclusive girls’ club, I could never see all of the complex dealings in the world a woman has to go through just to be successful. Including dealing with huge male egos which I was guilty of having. I just tried to transfer mine to my feminine side by obsessing the best I could about being an attractive woman. It became an all or nothing obsession which consumed me to a point where it was all I lived for and I am not proud of the experience. I wonder now, why my second wife stayed with me at all, but she did. 

As I always write about, it was not until I broke the self-imposed bonds, I had put myself under, did I begin to really understand the life I was pursuing. And figure out if I really wanted to do it because there was so much at stake. Everything I worked so hard at would need to be thrown in a giant trash can as I started all over again as a trans woman. No experience was a bad experience really came into play when I left the gay venues I was frequenting and started to try to socialize on an equal footing with the ciswomen in my world who would gather after work in a TGIF Fridays I went to as a man. When I was going there as a man, I always fantasized how it would be if I could do it as a woman and when I did, I was in heaven as well as being scared to death that I would be "discovered" and told to leave. Which thankfully never happened and I needed to step up my wardrobe options to keep blending in with the women around me.

It was not until then did the women around me begin to reach out to me when they saw that I was all alone and I began to build up a small circle of friends who turned out to be lesbians who were destined to teach me more than I ever imagined about the world and how to deal with it as an independent woman. The first thing I needed to do I discovered was to take the important step of validating who I was as a person. To take all the experiences I had accumulated and learn from them. By this time, most of the bad experiences had faded away, giving me the confidence to be myself for the first time in my life. When my validation was secure, I could move on and cross the gender border the way I wanted to. 

One thing was certain; I needed to keep being a keen observer of the genders around me if I was to continue to be successful.  Quickly I found, I was kicked out of the men' s club for good as they left me alone for the most part. Which was the direction I wanted to go anyhow because I had never felt comfortable around men and what they demanded from me to be successful in my life. For once, I felt comfortable in my life which added to the fact I had always felt so natural that I was doing the right thing when I was pursuing a feminine life. 

Finally, I bought into the idea that I was a unique human with a lot to offer to the world if they would accept me. To arrive at the point where I was, I needed to take all the good and bad experiences of my gender journey and combine them to succeed. When they did, I knew I had made it to my goal against all obstacles, and I was living my dream.

Thank you all very much for joining me and as always, I hope your experiences turn out to be positive ones. Comments are always appreciated.

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.

The Waiting Game

 

Image from Levi Mear Clancy
on UnSplash

As transgender women and transgender men, we often play the waiting game in life. In my case, I played the game frequently as I could not wait for the next time I could cross-dress and could put on makeup.

 

Early on in life I was naïve and thought that eventually I would grow out of my desire to be a girl if I just waited long enough. Of course, that never happened and I grew into a more established cross-dressing life, all the way to being a proud transgender woman. Often, I was very frustrated when I had to wait in my gender journey to clear obstacles in my path such as three years in the Army, the raising of my family and other things too numerous to mention.

 

There was also frustration when I had to learn what I was doing as I tried to cross the gender border. It was not as easy as just putting on a dress which fit me and applying skillful makeup. It took an extreme amount of time away from my unapproving family, a younger brother and an extreme amount of practice to do it right. None of the process was as easy as I had imagined but for the first time in my life, I was dedicated to doing something right and that was coming as close as I could to becoming a pretty girl. Adding to my increasing problems was that I had no choice but to go through male puberty with all the unwanted masculine qualities I received but had not asked for.

 

It seemed, the older I became the waiting game for me increased completely with it. I was still trying to carve out time to cross-dress in my closet which in itself was becoming increasingly frustrating. The time was upon me to leave my closet for the first time and see if I could make it in the world as a feminine person. Somehow, I gathered the courage to go out and then was completely rejected by the public. All my failures combined to send me back to my gender closet and return to my waiting game. Finally, I reached a point where I could wait no longer and kept trying the world until I got it right and I was blending in with the world at large where I was going. When I did, my paranoia about going out decreased and my confidence increased as I began to relax and enjoy myself.

 

As all of this was happening, it was becoming increasingly evident that a tour of duty in the military was going to be in my future. To attempt to stay out of combat in the Vietnam War, I decided to enlist for three long years, and avoid the draft. My problem was at that time in my life, three years seemed like an eternity. Especially away from my dresses and makeup. As well as the new long blond wig I managed to purchase for a girlfriend I had in college who hated the wig, so I managed to get it back. A dream came true for me until I had to leave it behind for three long years until I could get back home and wear it again.

 

When I served my three years and was back in the civilian world, I again was naïve and thought most of my waiting game was behind me. In fact, it was just getting started when the Halloween parties I went to as a woman, showed me that I could possibly live my dream of a transfeminine person after all. I just had to find the hidden keys to unlock my future which was not going to be easy as I thought it was going to be as I delved further into what I would have to do to survive and thrive in a world made up by ciswomen. As much as I had studied the world of women around me, I was not ready to go behind the gender curtain and be admitted into the girls’ club. A woman’s life was much more complex than I ever imagined and the first fact that I learned was why cismen and women do not understand each other. In order to make it into the girls’ sandbox, the first thing I needed to do was understand the new form of communication I was challenged to learn. It was true that men were from Mars and women were from Venus and initially, I felt I was on the Moon. The ultimate gender traveler.

 

The positive part of my life at that time was, my waiting game was speeding up, and I was learning new lessons on where I should be in the world nightly when I went out to socialize with my new ciswomen friends. Without them knowing it, I set back and let all of them be my feminine teachers as I tried to round off what was left of my old male life. Even still, I was impatient about how my life was going and wanted to know what was around the next blind curve on my gender path. I had waited long enough with the time I had spent by myself trying to learn a new life which included a whole new gender language.

 

Before I made the final decision to end my waiting game and jump into the girls ‘club I needed to pause and look back and see if I was making the right decision with my life. Since I was giving up almost all the male privileges, I had worked so hard to gain. I finally got so frustrated with myself that I had to do something about it. I was tired of worrying every moment of the day about what I was going to do. One night I said enough was enough and it was time to begin HRT gender affirming hormones and leave my past behind.

 

I will never think that the waiting game I played was a good thing, but it turned out I had to play out the cards that I had. We are all different which makes us human and interesting as trans folk. We just must get the remainder of the world to accept us. The fact remains the world does not take the time to understand us. So do not expect it. What you can expect is a fair break from the world as you follow your path. That way your waiting game may be a little easier.

 

Thanks for listening to my waiting game I was playing. Any comments are appreciated.

 

 

 

She Was Always There

 

Trans Ohio Symposium
JJ Hart

No matter where I went in my life, she was always there.

It did not matter if I was in the middle of playing a football game as a defensive end, she was always with me wanting instead to be a cheerleader. She carried over into my everyday life also as I daydreamed all the time what if would be like to cross the gender border and live a feminine life. As I dreamed my life away, my feminine side may have had an unfair advantage because I was only seeing the positives of being a girl or a woman. It seemed so unfair to me that they could wear all the pretty clothes, have long hair and not have to worry about being forced into military duty during the Vietnam War. Plus, why did I have to be the chaser whenever I wanted to ask someone out. I never saw the competition between the girls for attention, being able to wear makeup and more. They were far from the simple life I was seeing but had no one to tell me so.

Even so, she was always lurking in the background as I fought off the shyness, I felt when I had to be around people I did not know in public. Especially other girls. I did not know then why I was attracted to them in a non-sexual manner because it would be the way I would live my life as I grew older. I learned my natural comfort zone in public always came with other women and I never felt comfortable making friends with men at all. Maybe it was because she was always there in the background. Telling me what to do.

When she did, often major conflicts in my life would occur because in my male life I was always trying to put up a macho front to keep the bullies away. It was difficult to do when she was always whispering in my ear, I was doing the wrong thing when all I was doing was to survive my gender dysphoria and live. It was the beginning of a lifetime of warring genders that would consume me to the point of self-destructive behavior.

When I progressed in my career into management, she was always with me when I needed to handle the women in my crews different than the men. She was studying the way I handled myself and how the ciswomen I was dealing with handled me. Primarily, I learned a lot about how women exist with each other and how alpha females can control a clique of other women. It would be valuable experience later in life for me when I was trying to gain acceptance to the girls’ club. If I had an alpha or two helping me along, they could make my life so much easier.

It began to matter more to me when I began to listen more and more to the feminine voice who was talking to me. She was a powerful influence when other women approached me to investigate what I was all about. Somehow, I was like them but yet so different as a transgender woman. I would have to learn how to build trust with other women as a like minded person and only use the long unwanted male basics of my life when I was asked to. Such as when women asked me questions about understanding their boyfriends or husbands. The last thing I wanted to say was I never understood them either, so I helped the best I could and I was flattered by the questions.

Most certainly, she was more than in the background when I started to explore the world as a trans woman. To do it, interaction and communication was the key as I had to come way out of my closet to do it. I even went as far as taking feminine vocalization lessons to learn more about how to communicate more effectively one on one in the world. The lessons were wonderful and taught me more than I ever thought they would. I knew of course that ciswomen had their own way of communication, but not as much as I learned about the nuances of feminine speech patterns. It was a huge change for me as I had developed many bad listening habits as a man that I needed to change…quickly, if I wanted to survive and thrive as a transfeminine person. Such as beginning to closely listen to what another person was telling me rather than skipping over it to how I was planning on answering it.

As I added layer upon layer in the world to the feminine self I was building, I did not have to pay attention to the woman within me that had always been there in the background. She was having a chance to see the fruits of always being with me come to bear as she was able to take over my world. Since I had already put in years of effort into my presentation as a trans woman and had taken it about as far as I could, my background woman was overjoyed to see me take the extra step and listen to her where to go next. That step was to put the communication mode fully into my life and complete my feminine image in the world. I finally made it out of my closet’s mirror and had a chance to be happy. Something that was never emphasized in my family when I grew up. I did not know how to act with such a new emotion.

Then it became time to flip my gender equation. My male self still vaguely exists as my female self runs my life. I discovered it was nearly impossible for me to erase the decades I had in life doing my best to make it in an unwanted male world. So, I tried to take the best and leave the rest behind. It is working for me so far.

Speaking of working for me, I will not be writing tomorrow as I must go to my new Veterans Administration clinic for my annual checkup, Flu and Covid immunizations and even blood labs. I have not had any problems for years at the VA because of my gender, so I do not expect any tomorrow. But if past Flu and Covid shots are any indication, I will not feel like writing. If any thing crazy happens with the clinic’s personnel disrespecting me, I will report it.

Thanks as always to reading along with my gender journey exploits. Hopefully my thoughts can be of value to you.

 

 

 

 

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!

 

 

A Destination or a Retreat into Trans Womanhood

Image from Brian Wangenheim
on UnSplash. 

As a youth, all I did when I failed at a male task was to seek the reassuring feelings of my feminine clothes and makeup. I knew then I would not have the male world I hated for a while.

The pattern continued with me into adulthood and was even expanded to include a better sense of wardrobe and makeup as I ventured into the world. But then it started to slowly reverse as I started to blend in with the ciswomen around me. Increasingly, I was feeling better about the progress I was making as a serious cross-dresser and wanted to do more as I moved towards being a transgender woman in my mind. Even though I was still extremely lonely as my feminine self, I was starting to embrace the unique person that I was. Afterall, how many people get to experience both sides of the primary genders in their lives.

On occasion, I even reverted to appreciating all the male privileges I had learned after a particularly brutal day of exploring the world of cross-dressing. Early on there were many I needed to go through as I continued to pay my dues to get to my dream of possibly living my life as a transfeminine person. Not a man.

Even though mixing genders was beginning to have a bit of normalcy for me, I came to the point where I would not recommend the journey to just anyone who was not totally committed to it. My mental health, which was already frail at the time, did not take easily to the journey ahead and it suffered. Again, sending me back to the comparative safety of the only other life I had learned to live successfully when I was competing as a man in the world.  At that point, it was difficult to tell if I was on a trans destination or a male retreat. The only thing that kept me going down my path was the deep sense of satisfaction or gender euphoria I felt when everything was going better when I interacted with the world as my true authentic self. Free and out of the closet for a change.

It took me years of experimentation in public, as I set up my own personal bucket list of what I perceived to be the real-world ciswomen had to face in their lives. I figured out why I would want to go there if I could not make it. In other words, I kept challenging my feminine self to do more and more such as do more than just spend very little time in public just walking around or shopping in easy venues such as women’s clothing stores where your money overcomes any reaction to your possible gender when it came to testing myself. I certainly then was setting myself up for a possible transgender destination in my life as I worked my way through my bucket list.

As with anything else in life, all I had learned about being in the world was not all positive and I found myself deeper into my quest to cross the gender border and complete my male to female femininization project. I learned the hard way to try to not get myself into questionable safety situations that women know not to get into that do not bother men. It seemed the gender universe was testing me on certain nights such as the one I needed to fend off negative advances from a much bigger cross-dresser admirer at a party I was at with the help of my second wife. Something I never bargained for as I went around a blind corner on my gender path. It was easier to think about erasing all my male privileges such as safety but harder to learn what to replace them with.

I do not think I ever did replace my new lack of intelligence with the cismen I interacted with as I was mansplained more times than I cared to remember by men of questionable intellect. Such as the tow truck driver I was forced into a conversation with one night when he was towing my car home. I had to sit there, and act interested when he had to tell me all the workings of his truck. Like I cared when all I wanted was to get home safe and sound. Which I did. All the bucket lists in the world did not prepare me for the reality of living a feminine life, but even still, I was loving everything I learned behind the gender curtain. If I was ever a girl scout, I would earn merit badges like what to do if your car breaks down when you are by yourself and the first person who stops to help is a sheriff. Who would not listen to me when I was trying to explain to him and the tow driver the easiest way to my house. I finally just gave up.

It soon was becoming obvious to me that I was no longer retreating behind my dresses and makeup to cover any vestiges of a male life I wanted to cover up. Instead, my full-fledged female life was a complete destination. A destination I wanted to do more than anything I ever had done in my life. There would be no more retreating back to my male world. No matter how easy it would have been to do it because he had always kept a comfortable home for me if I ever wanted to return. Much to his disappointment, I continued my feminine destination into the world of HRT gender affirming hormones which separated me farther from ever hiding again in my old unwanted male world.

HRT was certainly the end for any thoughts of ever returning to my old male self because I felt to increasingly natural when I took them. It was as if my body was telling me what took so long as my external self-synced up with the woman, I always saw myself to be. It just took me years to get there. Which was the tragic result of me not listening to myself.

Thanks for reading along on a few of my trials and tribulations of my gender journey. I hope yours is much smoother. Any comments are always appreciated.

 

 

I Did Not Just Wake Up This Way

 

Image from We Vibe Toys
on UnSplash

I get a sense of amusement (mixed in with a little frustration) when someone thinks I just woke up one day and decided to put on a dress and makeup.

I don’t have much energy to keep explaining how my gender dysphoria has always been a part of me and one I did not ask for. My frustration sets in when some time ago, an acquaintance from the transgender community I met proudly told me she had never been gender dysphoric in her life which I had a hard time believing since she finally went through the extensive gender realignment surgeries.

Then, I began to think did she or even me know the true definition of gender dysphoria. So, I went to look it up from a well-known online dictionary and here is what I came up with: “ a state of severe distress or unhappiness caused by feeling that one's gender identity does not match one's sex as registered at birth.”  I felt that my acquaintance simply did not know the meaning of the words.

Immediately it made sense to me because that is the way I felt growing up wondering if I was a boy or a girl. The only thing I knew for sure was the way I was born and how it affected my life. Perhaps the worst thing was that if I did not understand the way I was with my gender mix-up, how could I possibly expect anyone else to understand it either. So, I headed down the worst path ever and tried to internalize all of my feelings. Internalizing left me with only one way out. Which was to attempt to cross-dress myself in front of the mirror as a girl, away from my perceived dominant male gender.

As many of you know, cross-dressing in secret behind the back of your family is never easy as you have to sneak around and plan every spare moment to do it. It was something I would not have wished on my worst enemy. Why couldn’t I just have been a so-called normal boy like all if my friends seemed to be. Then reality set in as I realized again, I was not “normal” to many people and would have to live with it. Living with it became increasingly more complex as I matured as a serious cross-dresser into an even more serious transgender woman. I evolved into needing more than just admiring my feminine self in the mirror and wondered if I could do it in the world too. Before I did, I needed to gather the courage and confidence to do it. Which was very difficult for me to do because I just did not wake up and lose all the insecurities I had in my life. Many of which involved me ever being able to live as a woman, trans or not.

As I always mention, my early days in the world as a novice transfeminine person were not easy until I developed the tools in dressing myself and learning the basic makeup arts so I could blend in with the ciswomen around me. After many failures in the malls, I finally knew I had made it when the teen girls who used to notice and harass me began to leave me alone and concentrate on their own developing socializations into women. Which was the same path I was on. Just from a totally different direction, but it was taking me awhile to wake up and realize it.

One of the reasons was that my male life kept getting in my way. He needed space to continue to work on his marriage, help care for a daughter, and work on expanding to a growing successful career. Nothing too remarkable for most cismen, but very difficult for the average transgender woman trying to build her life at the same time. The worst-case scenario happened and the two binary genders within me began to compete for space at the same time. It was like the old days of waking up wondering what gender I was going to be any given day and the stress to my overall mental health was building more than I can say. I became very self-destructive as I finally thought I was not strong enough to handle the life I was given.

Somehow, day to day, I put my life together trying to remember who I was that day until I was fully able to try to disguise my true feminine self to the world. While, at the same time presenting myself as my “normal” male self. I ended up covering my feminine tracks so well that no one expressed to me that they knew all along when I finally emerged into my transgender world. They were all surprised that I never showed any signs of the true journey I was on with my gender.

When I finally woke up to the fact of who I really was, it was as though a tremendous weight had been lifted from my shoulders. I did not need my “Two C’s” so much anymore to get me by in the world. I was gaining the confidence I needed so I did not need as much courage as it took previously to carve out a new life as a woman and blend in with all of the ciswomen around me in their world. Saying that I was overjoyed when my life was coming together would be an oversimplification as age-old questions for me were starting to be answered. The main one was that I had been living my life backwards for decades causing conflict. Regardless of what society told me, I was never a man. I was a woman trying my best to lead a male life. For the most part I was successful, which made matters worse as my genders clashed for survival.

All along, I just wanted the battle to end so I could live my life in peace. I had my feminine side telling me how natural her life felt when she was allowed to live it. While at the same time, my male side was questioning why I would ever give up all the male privileges I had gained over the span of my life.

I chose the natural path which led me to a happy feminine life over the materialistic life which had only brought me stress because I was in the wrong place. Waking up was the best thing I ever did.

Thanks so much for reading along with my transgender experiences. Hopefully they can help you to understand yours too! Any comments are always appreciated.

 

 

How Halloween Benefitted Me

 

Image from Jennifer Marquez
on UnSplash. 

In the recent past, I have written a couple of stories about my Halloween experiences but there were more which taught me valuable lessons about the possibility of following my gender path.

Such as the time I was able to set up a training trip down to my company’s headquarters in Lexington, Kentucky to coincide with my favorite time of the year which was Halloween. In those days, the fashion rage was very much into fake leather, and I could not wait to show off my new faux leather mini skirt and matching top at a Halloween party. To get ready for the trip from Ohio to Kentucky I needed to find private time away from my wife to pack two sets of clothes. One for my male presentation at the company headquarters and another for my so called “costume.” Somehow, I was able to find room in my suitcase for makeup and a wig, and I was ready to go. The lessons I learned on that trip were that I could indeed pack effectively for two genders.

Once I arrived in Lexington, the next problem I faced was figuring out where I was going to go to show off my new “costume” in public for the first time. Luckily, the hotel I was staying in had several different publications in the lobby I could look at to see if I could find any parties that may be close by. I did, and then had to try to find them, after I was cross-dressed and ready to go. I was nervous as I put on the only pair of black panty hose I brought with me and put on the padding I needed to work with to provide a feminine figure. Next came my makeup and a resurrection of my wig following its time in my suitcase put on my heels and I was nervous and ready to go.

Probably, the biggest challenge I was going to face was going from my room to the elevator then worrying about facing anyone else as I went down to the hotel lobby. I should not have worried because I did not see another person until I arrived at the entrance and the ones I did act like I was not even there. Then, I was off to find the venue I was looking for in a city I was not familiar with at all. Back in those days, there was not such an invention as a GPS to help me along but somehow, I did find the first big venue I was looking for. Lesson learned. Try to find out where you are going before you get there. On the other hand, I had a powerful motivation to get out of my closet and see if I could survive in a straight world of Halloween party goers as a novice trans woman.

When I arrived at the entrance to the venue, they were checking identification at the door and surprisingly, no one reacted to the person in costume as a woman with the obviously male I.D. My hand was stamped and in I went to an unknown experience which might change my life as all the other Halloween experiences had done.

As I walked in, the venue was already packed, and I needed to find my way to the bar for a drink and the closest route was across the dance floor. I took a chance and made my way through the couples dancing and up to the bar. Once I ordered my drink and was served, I started back to a relatively uncrowded part of the club to enjoy people watching along with the feel of my “costume.” It was then that I learned the lesson of what it was like to be a ciswoman in a crowded venue with potentially toxic cismen who could not keep their hands off of my rear. I have never been pinched and touched so much in my life as I made my way back to one of the rare open seats I could find. Lesson learned again as I headed off to another venue to experience more of my evening before it was time to return to my hotel in my faux leather outfit.

I did find one other place which was having a party, so I decided to make it a night by stopping in there also. The second venue on was far less crowded and mellow than the first one and I was relaxed and had the confidence from my first experience to go right in. I was met by a friendly checker at the entrance and again no reference was made to my male identification which was probably due to the magic of it being Halloween.

One thing I did not do was stick around in either place for their costume contest because I was so insecure about myself. I did wonder if I did join the contest and somehow won if all the men who were fondling me would have been properly shamed but probably not. All they pinched was foam rubber anyhow and I went on my way with another powerful lesson learned about how ciswomen are really treated. I wondered if I had not been wearing any protective padding would I have bruised the next day.

The biggest problem I had was coming down off of my gender euphoria rush to effectively teach the company management classes I was supposed to teach. I did not make the trip to Lexington very often and was never able to spend a Halloween evening there again. When I went, I was often stuck going out with groups of other male managers to strip clubs where I did not really want to go. While I admired good female bodies, I never had the urge to go any farther. I was always the first to leave the strip clubs which made for a clearer head in the morning from no alcoholic hangover.

Without the benefits of many Halloween experiences, I am sure eventually I would have made it to my goal of living a fulltime transfeminine life, but it would have taken me longer. I would have not had the “A-Ha” moments I had from Halloween when I was able to see why women are able to exist in the world the way they do, and I will never forget the lessons I learned from my favorite holiday.

 

 

 

 

 

A Halloween Political Decision

Image from Nice M Nshuti
on UnSplash

This is the second in my month-long series of Halloween decisions I made during and after the parties I went to.

This party took place in a wonderfully restored Victorian Mansion in my hometown where I worked as a radio disc jockey. Just to get an invitation was impressive to me as I struggled to come up with a “costume” to wear. Ironically, by this time in my life I had almost went full circle in my choices of what I was going to wear. I had long since gone from my slutty/trashy woman look all the way to a more moderate less clownish woman with my “costume.” I could still try to be sexy without going overboard as most ciswomen around me were doing on Halloween.

I finally decided to go full circle and see if I could wear something so authentic that the normal party person would not recognize me as a guy at all. I thought it would be the ultimate chance to test how far I had come as a transgender woman in the world on a low risk-high reward Halloween evening. Once again, my wife did not want to go with me, so I ended up with the news girl at the radio station as my companion for the evening.

I discovered I was off to a good start as my companion for the evening marveled at my “costume.” I chose to be a professional woman, just getting off from work and coming to the party to test my newfound freedom in the world. For at least one night.

When we arrived and found a parking place, I loved how my heels clicked up the sidewalk as my “date asked me how long I had practiced in the heels to wear them as well as I did. I just told her longer than it took me to shave my legs and apply my own makeup, so she left me alone after that. As far as asking any further questions about my skills dressing as a woman. Fortunately, it was a beautiful warm evening for Ohio in October, so I did not have to worry about any sort of jacket, sweater or coat as we made our way up to the mansion’s front door. The whole house was beautifully decorated for Halloween, complete with a vintage wooden coffin complete with a real skeleton.

I was met at the door by the hosts for the evening who like my “date” marveled at my male to female transformation. With the good start I was having, I immediately started to relax in my new surroundings and enjoy looking at the other costumed visitors. I was just about ignored as I did manage to blend in as a professional woman until later in the evening when a couple arrived and started to talk to us. It was just after a little bit of conversation that they told me, they did not recognize me as a man at all, and my “costume” had worked. My mind was shooting fireworks of joy when they told me that and it even went on to new heights when they even asked me to leave with them and go to a different party.

By this time, I had recognized the couple who were very active in politics and was on their way to Washington due to a recent election victory. So at least I knew who I was dealing with and if it had been just up to me, I would have said yes and went to the other party with them. But it was not just up to me since I had driven and I needed to get my “date” back home, so I had to sadly make a split-second decision and say no. Either way, I was very flattered by the offer and who knows what I would have encountered as my feminine self at the other party. We stayed on at the original party for a while had a couple more drinks and headed back to the house where I needed to reluctantly return to my old male life for what I thought was going to be another year. Always maintaining the “what if” ideas if I had continued with the politician and his wife, Maybe I could have gone to Washington also.

Another good thing that happened with the Halloween party I went to was, it was the first time that I ever thought/proved I could make it in the world as my true feminine self. Plus, I knew I could not wait another year for Halloween to roll around for me to live as a novice transgender woman again. If I had made it one night as a professional woman in the world, there was no reason I could not do it again. I just had to take matters into my own hands and do something about my gender dysphoria which was helping to wreck my mental health.

The evening was also more proof I had done the right thing for a change when it came to testing the strength of my male to female femininization project. I found I was coming along faster than I thought and I could never go back to living the totally male life I had before I tested the gender waters at the Halloween parties I went to as a cross-dresser. It was as if I had found a giant search light on my gender path and suddenly, my life made more sense. It was so much deeper than anything I thought it could be.

That is why not going out with the politician and his wife maybe cost me a chance at more fun and even enlightenment about who I really was. But on the other hand, I did the right thing by my wife and my date if she did not want to go early and end my evening. I felt better about it in the years to come. Even though, I wonder what would have happened if I had made the other decision. Most likely nothing and the memories are better than the actual experience.

Another reason Halloween will forever occupy a special place in my soul and there were several other evenings I will try to pass along before the actual holiday. Thanks for reading along and commenting!

 

  

How Difficult Could it Be?

 

JJ Hart

When I started my transgender journey, I was very naïve and I kept thinking how hard it could be to stay on my path.

All I saw was the good side of being feminine with all the girls around me in their pretty clothes and long hair when I was stuck in all the restrictive, boring male clothes and very short haircuts. To make matters even worse, I needed to make sure I kept all of my cross-dressing activities very hidden from the family and friends who would have ridiculed me and called me a sissy boy. The worst thing I could be called in my very male dominated family.

As I said, I was naïve and for years thought that all I wanted from being feminine was looking like a woman, so I obsessed about it night and day. Eventually, I did come closer to achieving my goal while all the ignoring harassing comments from my second wife who rarely wore any makeup at all. On the rare occasions she went out with me, she constantly thought I was going too far with my makeup and hair to the point of calling me the “Princess”. When all I was doing was trying to blend in with the ciswomen around me by overcoming my old male self.  Of course, I felt the criticism was not fair and the evening was ruined. Often before it even got started. From that point forward, the fights started because she did not like the trans woman I was becoming. And I did not understand why.

I think now that she thought I had not paid my dues as a woman yet to claim the socialization title and she was right. I was still stubborn and did not know how I ever was going to have the chance to play in the girls’ sandbox if I did not want it bad enough. I was stuck between two massive changes in my life which would either involve giving up the woman that I loved for one that I was learning to love. How hard life could be was becoming a reality for me like a boulder rolling down a cliff directly at me. It was quickly becoming unbearably hard when I discovered I could indeed see a path ahead of living my life as a transfeminine person.

What happened next was that I began to step away from my wife and essentially live the life she challenged me to live. That is to begin to socialize myself as a transgender woman in the world. I started to meet strangers as a trans woman who never knew me as a man and start all over in a new life. How hard could it be? It was and the whole process scared me to death. I was terrified of being stripped of all my old male privileges and having nowhere to turn if something negative happened to me. How would I be able to react to potentially negative situations in my new life. It turned out I did not have many potentially negative problems, and I was able to grow into my new feminine person with very few problems because most of the world did not care what gender I was. They were too wrapped up in their own worlds. Especially the cismen who were so afraid of their fragile sexuality that they left me alone. Which was fine by me, since I had always had a problem with making friends with other men when I was trying to be one anyhow.

Ciswomen, on the other hand, were much more willing to let me in their worlds and even show me around. Making it less hard to be one of them as I was learning daily how to fill out my life. I always had enjoyed being around women and found I even enjoyed it more when I was made a member in good standing of the girls’ club. Being in the club entitled me to use women’ only spaces such as restrooms which made my life so much easier also.

Most likely, I made some male to female transition issues more difficult than they should have been. Such as when I first came out into the world and thought everyone was looking at me, when they were not. I even went as far as to wear a favorite pair of sunglasses I had to see if anyone was staring at me without them knowing it. They were not, I was relieved and was able to go on with my new life. With new confidence I never had before. Maybe I could achieve my dream after all. It was a scary thought because then I had to start to think about what I was going do with all the excess male baggage I had built up over the years when I was trying my best to hide my true self by being a successful man.

The entire focus of my life changed as I began to consider the new and exciting reality of being able to live out my dream I had wanted since I was a child. I was sad when I could not tell the truth when an adult asked me what I wanted to be when I grew up and I could not say a woman and earn a quick trip to therapy by my parents. At the time, being a woman seemed as far away to me as being a lawyer or a doctor. But at the same time, a dream I really wanted to live.

Along the way, two things were evident to me. One of which was every time I achieved a goal on my path, another would appear for me to consider doing. And the second thing was, every time I began to doubt myself, I would start to feel natural about my journey and it would re-energize me, so I could move forward again. Forward was always good and made me feel better about my life which brings me back to my original point of how hard it could be to cross the gender border. Exceedingly difficult at times to be sure, but excitingly natural as I was doing it.

Wherever you are on your path to a better tomorrow, I hope you can discover your truth and make it in one piece. As always, thank you for reading and comments are always appreciated!