Connecting the Gender Dots

 

Image from Beya Yurtzkuran'
on UnSplash. 

Connecting all the dots in a life when you have gender issues is never easy.

Especially so when your life’s workbook is completely blank and you have nowhere to go but to struggle. The great majority of transgender women and transgender men grew up with unapproving parents and/or no peer group pressure to shape our gender youth and help us along. At the best, the closest dots we were trying to connect were fuzzy and far away.

On the other hand, with me, my male dots were always crystal clear and easy to at least try to connect. If I was successful on a sports team, I would connect an easy dot is a great example. But if I was cross-dressing as a girl in front of the mirror, I was always confused on how I should act or feel. The only certainty I had was I knew I wanted to feel pretty.

As I progressed through life’s lessons, I learned the impact of achieving the connecting of my feminine dots while at the same time, leaving my male ones behind. Sacrifice became the ultimate name of the game. Especially when my second (out of three wives) kept calling me selfish for my complete pursuit to begin to leave my male past behind and live as a complete transfeminine person. What made matters worse was the fact that my gender dots on both sides of the spectrum were becoming clearer. I was becoming more successful as a father and as a provider as I advanced in my chosen profession, but at the same time, I became better and better at presenting myself as a convincing woman. For the longest time, my dots formed a parallel path. Heading ultimately for a collision.

I was stubborn and tried to separate the dots I was connecting until it affected my mental health so badly I could do it no longer. I was like a juggler trying to balance the two main binary genders as fast as I could and it nearly cost me my life. I was finding it harder than ever to separate my old unwanted male self from my new exciting yet terrifying new feminine self when one side began to bleed into the other. For example, when I was in a company meeting full of men, I would daydream how it would be if I was there as the only woman. Before reality would slap me down and back into the present.

Finally, I could take it no longer, and I began to give up on connecting any more of my male dots at all. I figured if I connected any more dots, it would just create more baggage I would have to deal with when I male to female transitioned. Mentally, I began to make contingency plans on what to do when I could ever connect my female dots and live out my dream. It is when I began to kick my experimentation portion of my life into high gear. I wanted to make certain as little as possible would be standing in my way as I moved forward in life. I needed to deal with the possibility I would lose contact with my wife and family then figure out what I would do to support myself financially. I was fortunate when my daughter stuck around to support me when my only remaining blood relative (brother) did not and I was old enough to support myself on an early social security retirement I earned and selling collectables my second wife who tragically passed away, and I collected over the years. So, I had connected all my obvious dots fairly well.

From there, the most challenging aspect of life I needed to face was the actual one on one daily living a trans woman has to take on. Learning the lessons a ciswoman is raised to know as she transitions from a female to a woman. Such as the shifting from white male privileges to the female privileges that I had only had the chance to dream about and not know because I had never been allowed behind the gender curtain. Once I was allowed behind the curtain, many aspects I never fully realized ciswomen actually go through became a reality to me. I was connecting my dots and maturing into the transgender woman I always dreamed of becoming. All my misconceptions about just achieving the appearance aspect of femininization faded away as I learned there was so much more to me than just trying my best to have an attractive face. It was quite the shallow existence for me as I needed to develop myself into a quality new human being that the world reacted to on a everyday basis.

As it turned out, HRT or gender affirming hormones took final care of the attractive part of my being as I went from being attractive to being the real me. Because the hormones softened my skin and facial lines and helped me to grow breasts, hips and hair. Like I said, all of which were the real me just waiting all this time for the changes to happen.

All the dots I connected were in a big circle. I went from a young boy for the first time being amazed at what he saw in the mirror (and wondering what was next), all the way to being able years later to being able to find the real me and live out my goal of crossing the gender border into a transfeminine world. I could not wait to give away all my male clothes; enjoy the new hormones I was on and live a new life. I was even able to take vacations with my third wife Liz to places I had never been before. All as my new self.

I can’t say connecting all my dots was ever fun and at times very scary, but they were always with me as I lived my life. At my advanced age of seventy-six, I am fortunate that I had the chance to find the real me before it was time for me to connect the final dot and step into the next dimension.

 

 

 

 

 

 

 

Stopping when You are Ahead

 

JJ Hart. Girls Night Out.
I am top left. 

Somehow, I never learned to stop when I was ahead when I was growing up. Or, as my parents always said, I tried when I was given an inch, I always tried to take a mile.

That whole idea really manifested itself when I began to explore my gender desires and start to cross-dress in my mom’s clothes. As I perceived myself to be successful with one new look, I always wanted more very soon. I could not stop when I was ahead and kept on pushing the boundaries of danger when I cross-dressed at home in the bathroom. Even if my brother was home too. I was risking what I had of the young male life I thought I needed to protect.

Somehow, my guardian angel was looking over me as I never got caught as a kid with my cross-dressing activities and I simply wanted more than I could get most of the time such as a nice, fashionable wig. Rather than the Halloween store wigs I was stuck with. Due primarily to financial constraints. During this time of my life, I was stuck with just being able to dream of what my life could be like when I grew into a more complete transfeminine person. It turned out to be a long (decades) away from coming true. Take wigs for example. When I finally arrived at the point where I financially could afford it, I went overboard on haunting the local wig stores around me looking for just the right wig which I thought would be the perfect addition to my hair collection to allow me to present better in the world. As I did it, mostly all that I accomplished was acquiring quite the collection of potential drag clown wigs which I did not have the patience and/or knowledge to take care of.

At that point, I could not stop when I was ahead or behind my quest to be at least an attractive woman. Every time I experienced the least little bit of gender euphoria when I went out in public, it fired me up and encouraged me to do more. Unfortunately, that meant taking extra chances with my actions and ultimately my safety. I needed to learn the hard way what ciswomen were raised to know about not putting yourself into potentially dangerous situations. I barely lucked it out when I escaped situations with no harm to me, so I essentially did not have to stop when I was ahead as a trans woman. I just had to be wiser when my male privileges were stripped away such as the personal security privilege men inherently have.

As I emerged as a wiser novice transgender woman, the reality of what I was attempting set in and I could not stop. Even if I was ahead. I began to set up a stairstep approach to my male to female feminization process which would I hoped, give me a more in-depth look at a woman’s life behind the gender curtain. Which I had spent countless hours thinking about. I started to consider all the things I wanted to discover as a woman that I had dreamed of as a man which led me to set up my own transgender mental bucket list of things to do. Basically, I set up activities at levels of difficulty. So, when I accomplished one I did not have to stop and move to another. Using the women’s room was a prime example of sliding behind the gender curtain and using a women’s only space. I knew a little of what to expect from my days as a restaurant manager when I needed to monitor how the women’s room was kept for problems I could encounter. Not starting from scratch helped me to survive in my new world with cis women.

Fortunately, I spent much of my time in the world successfully as I learned the basics of how ciswomen live. By doing so, I simply could not quit and kept on trying new things. My bucket was quickly being worn out by the challenges I was facing. Mainly by meeting the number of women who showed interest in me. I have always thought they were just curious about what I was doing in their world and was I living my life the best I could in the girls’ club. In my case, I was different and hopefully presented the best of the two main binary gender worlds as I socialized with many different women who seemingly were happy to see me.

By this time in my life, I simply could not stop what I had started as far as chasing my femininization process. It involved doing a deep dive into how women communicate and compete with each other, among other important things. Probably, communication was the most difficult aspect of my transition to learn. For the first time in my life as a transwoman, I needed to listen closely and completely to what was being said to me for hidden meanings and nonverbal cues. Then, as far as competition as a woman was concerned, I needed to learn that women compete just as hard as men. Just on a whole different spectrum of passive aggressive actions and reactions. Believe me, I learned the hard way a number of times when I made the wrong move and needed to watch my back from a smiling face who was out to get me.

Once I succeeded in learning all of my feminine lessons, my confidence was at a all time high. Especially with the small group of lesbian friends I had build around me by sheer luck. They ended up protecting me during my fragile times I was learning the final ropes of what it would take to round myself out as a transgender woman. By this time, my inner self could take over after being buried all those years and end up running my life’s goal that she always had a hand in. After waiting all those decades to live, she no longer had to stop while she was ahead. She was home and I was a whole person.

 

 

 

Burning my Gender Bridges

 

Image from Kellen Riggin 
on UnSplash. 

Sadly, following  my gender path included burning many bridges behind me which connected me to my old male past.

I think the problem stemmed from the self-destructive behavior I always exhibited when I did anything remotely successful as a man. I still had not yet faced the fact that I wanted nothing to do with being a guy, and everything that came with it. Including the potential of living with the white male privilege that was an automatic addition to my life.

Then, there was always the part of relief if I was ever caught cross-dressing early in life. Finally, I would be exposed as the deeply feminine person I really was. Life was much simpler back in those days, and I wondered how bad it would be to go to a psychiatrist and try to explain to him or her how I was not mentally ill; I just wanted to be a girl and my ultimate goal in life was to grow into a woman someday. The only way to get there was to risk everything and not get caught, but I never did and did not have to burn any bridges to find my way into early forms of conversion therapy.

It was not until much later in life did, I really began to torch my bridges behind me. The problem was, I needed to build my bridges longer and stronger to carry all the increased male baggage I had accumulated. Most of which was against my will. This was when my male life was outpacing my female life and I was building a small family and a very good job while at the same time managing to hang on to a long-term marriage where my wife was learning about and fighting against any thoughts of me sliding towards leading a transgender lifestyle. I desperately did not want her to be on any bridge that I burnt, and the pressure built on me not to light the match on my life if I took the huge step and decided to keep femininizing myself.

As I reached deeper and deeper into myself looking for an answer, I felt increasingly natural when I was attempting to put together my feminine self. No matter how risky burning my previous gender bridges behind was, I could not shake the idea I was doing something right by transitioning my old male life away.

The next big problem I faced was letting the world I was in know I was switching from my male club membership to the girls’ club. As I was being increasingly successful in carving out a new secret life as a trans woman, I did not want it to be secret any longer. So, I did the natural thing for me, I tried to make it impossible for me to turn back on my gender path. I started to go into my own restaurant dressed as me to see if I was recognized which I quickly was. I could have lost my executive general manager’s job immediately if I was but I was prepared to burn that bridge when I came to it. Looking back, it was not the smartest decision I ever made in my life but one I was desperate to make as my female self was crying out for attention.

When I progressed to a certain point in my male to female transition plan, burning bridges became just an automatic part of the plan because I did not need the male part of my life anymore, I was getting rid of. The prime example as I always point to is the night that something had changed in my thinking that I was not cross-dressing to go out and socialize, I was finally trying to formally join the world as a full-fledged transfeminine participant. The evening was a resounding success, and I knew from that point forward that I could never go back to being a man again. I could see my bridge burning over a not-so-distant horizon and it actually was scary and good at the same time.

I probably would have burnt more bridges earlier in my life if it was not for my second wife and my male self who was hanging on for dear life but still refusing to give up his hold on me. They put up a formidable fight to the point of putting out the fires I started on purpose. It lasted until my wife passed away, leaving only my weakened male self to fight me.

The final bridge to burn was when I was approved for HRT or gender affirming hormones. It was an all hands-on deck torching when my external and even internal body began to change. My sudden change in skin tone, slightly protruding breasts and longer hair which I refused to cut gave my external transition away and the part no one saw, but I felt, such as my emotional growth made itself known to me.

Following years of gender turmoil and change, having nothing in my way felt very good and I loved the hormonal changes I was going through with my new wife Liz. Which was well over a decade now. As I said, burning bridges in my life was always a scary idea but one I needed to do to get to where I wanted to go as a transgender woman surviving in the world of ciswomen everywhere.

I was fortunate in that I did not get burned as much as I did along the way in the process. I must have been quicker than I thought as my trans destiny showed me the way during the darkest nights. Who knows? Being caught on one of my bridges may have been for the best when I needed to work my way out of danger, but it never came to that with me. I became quite good at burning my bridges…or lucky.

Thanks to all of you who have taken the time to comment, clap or subscribe and just read along with me.

Without you, it means nothing!

 

 

 

 

Nothing Lasts Forever...or Does It?

 

Image from Lucas Stankey
on UnSplash. 

Yesterday when I first went to the bathroom to begin my start to the day, I turned the light on and was greeted by a slight “pop” and the bulb going out. I was disappointed that it was one of those bulbs that is supposed to last forever. Then, I began to think that nothing lasts forever, especially light bulbs no matter what they say.

As I normally always do, I took the idea I was following to another level and compared it with my old broken-down self. No surprise, but I was not built to last forever either. Just like my transgender desires, or were they? I know when I was very young trying on my mom’s clothes and makeup, I thought perhaps I would outgrow my desire to be a girl as I became older. As it turned out, the opposite was true. I did not outgrow my desire to be feminine; I grew into it as I became more skilled in applying make-up and cross-dressing myself the more, I wanted to try my newfound skills in the public eye.

When I accomplished the seismic shift from mirror approval to public approval, I knew any approval would not last forever because of the mixed reactions I was having in public where I tried to go. Outside of the usual gaggle of teen girls who would laugh at me, I found that the largest part of society did not notice me when I took the effort to blend in with the other ciswomen around me. The mistake I was making was very simple when I finally took the time to figure it out. To dress for success did not mean to dress to attract unwanted extra attention. Success meant that I fit in with the public at large. Carefully, since I was a large woman, but a woman none the less when I presented myself correctly.

At that point, the responsibility of being a stable presentable transfeminine person began to set in. Just looking the part of a woman would not last forever as by then I certainly knew I would never just outgrow my feminine desires. By responsibility I mean it became time for me to fully accept what I was becoming in the world. To catch up, I took feminine vocal lessons to improve the nuances of my speech patterns and worked hard to listen to my progress. If nothing was going to last forever in my life as a trans woman, I was driven to do it right. Outside of the very good job I had and the relationship I was desperately clinging to with my wife, being a transgender woman who passed in the world was my ultimate goal.

That point in my life became a blur as I was learning almost daily what went on behind the gender curtain, I was given access to. It was not all good, but I knew the bad would not last forever if I continued past the stop signs, I encountered on my gender path to my ultimate goal of shedding my male past. The best part was no one knew him and I could build a new life from scratch with the good and bad of living as long as I did as a man. Everything was going so well for awhile that I was waiting for the next high heeled shoe to fall on me since nothing lasts forever. Sadly, I was right when my personal world around me began to rapidly crumble.

I call it my dark period when almost everyone I cared about passed away. I knew about the finality of death because of my parent’s death, but I wrongly assumed I would be the first to go in the small circle of friends and family I had built up because of my self-destructive lifestyle.

The person who helped me out of my dark age was my wife Liz who made me a believer in myself, and my forever could be with her. That was over twelve years ago now, and I hope it can go on forever too. I am just grateful I was able to find her when I needed her the most because I was drinking way too much and struggling.

The moral to the story is that life is but a circle and you can ride out the down parts if destiny shows you the way. It was true for me that the darkest hour was right before the dawn when I attempted the ultimate self-destructive act of all. Taking my own life. I failed and ended up being able to live the most exciting and self-fulfilling days of my life. I would have missed everything from the tour bus experiences Liz and I took all the way to being humbled in my two fairly recent hospital stays for Covid and pneumonia. Sometimes I think I was just given the chance to do as much living as I could in the time allotted to me. Being transgender just added to the mystique of my life.

Whatever the case, I was completely wrong when I was a kid thinking I would grow out of my dreams of being a woman, transgender or not. Growing into my dreams was certainly the most challenging thing I have ever attempted. Sometimes causing me joy and sometimes causing me extreme pain and suffering.

I know nothing lasts forever, but when mine ends, I will know I gave it my best shot.

Recently I learned that even backwards Ohio who only concentrates of passing anti-transgender bills, is considering a bill which would legalize euthanasia for terminally ill persons. Even though I seriously doubt the republican legislature will pass the bill, it would be nice to be able to end your own life when the time has come and gone to do it. I would love to have control of my own destiny. Nothing lasts forever, including humans.

Sorry to end this on such a negative tone but death is as sure as birth and we need to make the best of it.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

My Gender Workbook was Blank

 

Image from Marcus Winkler
on UnSplash. 

Somedays, I prefer explaining the trip up my gender path as filling out my gender workbook. Of course, the problem I had doing it was I had absolutely no help. No mother or peer group pressure to tell me if I was doing right from wrong when it came to cross-dressing myself as a girl or applying makeup.

Ironically (as I said in a recent post), knowing my mom the way I did she would have been against me shaving my legs and wearing makeup as early as I did as her secret daughter. I was only trying to get a head start on writing my own gender workbook and trying to catch up with all the girls around me who also were sneaking around wearing makeup and wearing panty hose.

It was fairly easy for me to make up my own workbook rules when it was just me and the mirror to deal with. No matter what I did as far as my feminine presentation was concerned was accepted by my mirror which kept lying to me and telling me I was a pretty girl. Which was much easier before I hit the curse of male puberty and all the changes my body was going through. I was seeing unwanted growth and angles while the girls I envied around me were getting curves. When I went to bed every night, I dreamed of my life being different but of course it never was. I would not get the curves I wanted until decades later in life when I was fortunate to have good health enough to be able to start HRT or gender affirming hormones.

There turned out to be tons of effort I needed to put into my workbook before I could arrive at the point where I could even think about starting hormones. The shortcuts I kept trying to make never seemed to work and usually got me in trouble. When I did find trouble by trying to do too much with poor fashion choices, finally I gained some sense, rewrote my gender workbook and went on to successfully try to blend in with the world of ciswomen as a transgender woman. Looking back, I think that page of my book had so many erase and start over marks that I could barely read it.

When I really began to get serious about seeing if I could be successful as a trans woman was when I desperately needed my gender workbook to help me, but it just couldn’t because I had not put the time and effort into filling it out. I had never given enough thought to how different the lives of men and women really were. Perhaps you remember the book “Men are from Mars and Women are from Venus” which when I read it, I wondered where trans people came from. I did not know yet we transgender women and transgender men get to occupy a special planet all our own with our unique knowledge of both men and women.

As I first began to mature into a more complete transfeminine person, I sometimes discovered my mental gender notes became overwhelming, and I needed to head back home to go over in my mind about what just happened to me. Good or bad, it did not matter. What was most unexpected to me was the amount of acceptance I received in the new world I was in. I had become used to the glares and abuse I took when I went out of the house in my early days and learned the majority of the world did not care about me one way or another. All the way to those other women who encouraged me to be in their world. Nowhere in my gender workbook did I ever imagine such a thing ever happening to a person like me just trying to find a new foothold in the world as my authentic self after all the years of struggling.

Sadly, there were still times when I ran out of ink to write in my gender workbook, and I attempted to purge everything I had accomplished and go totally back to my old safe male world. As most of us know, purges never work, and before I knew it I was out buying more feminine clothes and makeup to femininize myself all over again. By doing so, I finally came to the point of stopping obsessing over how I looked and settled into just being the person I was meant to be all along. I just did not want anything to do with me being a privileged male anymore, I just wanted to live out the long-held dream goal of mine to live as close as I could to a woman.

Even at that point, my gender workbook was different than other trans women friends I had known when I made the decision to live my life without all the major gender realignment surgeries and facial surgeries the others had gone through. I had two comments which described me the best when a transwoman friend of mine said I passed out of sheer willpower and another which came in on a comment and said I was just another old guy on hormones. Both were right in their own ways, and I wrote a mental note in my workbook that I would never be the prettiest woman in the room, but I could be the nicest. As far as the comment on me being an old guy on hormones, I wondered if the commenter was just jealous and it did not matter anyhow because I had always considered my gender to be between my ears and not between my legs and I had made it through life as far as I did with no surgeries at all, so there was no need to risk damage when I was older.

Also, I was fortunate to have been able to have other ciswomen around me help finish my gender workbook to where it is today. More than they ever knew, they taught me how to validate myself as a trans woman and welcomed me into their world. A major accomplishment in my life.

 

More Changes

 

Image from Brad Starkey 
on UnSplash.

More changes are coming to our house beginning today. Thanks to my wife Liz, we are tearing out one of our old bathtubs and putting in a new walk-in shower. Which is perfect for my immobile status and makes it less dangerous for me to take a shower.

You would think, by this time in my life, I would be used to change but it seems I have just become more set in my ways as a senior citizen transgender woman. As with many of you, our gender issues changed us for the first time quite early in life. Mine manifested itself the first time I felt the magic of trying on my mom’s clothes and I worked my way forward from there.

At that time, I labored under the impression my love for feminine clothes would eventually go away but it was something I ended up growing into rather than away from. The older I got, the more skilled I became at acquiring key items in my wardrobe and hiding them away in places even my younger brother would not find. I even increased the number of odd jobs I would do (such as a newspaper route) to augment my meager allowance and allowed me to buy items such as makeup and panty hose which felt so good on my legs I was shaving earlier than probably half the girls my age that were allowed to do. To shave them I had to use my mom’s electric shaver which I needed to carefully clean after every use. Again, somehow, I managed to escape detection as I continued to cross dress.

It wasn’t until my military days that I really began to push for more changes in how I was approaching my femininity. It was a Halloween party I went to when I only had about eight months left to serve that changed everything. For my “costume” I chose a slutty woman’s look to go with my friends looks. Further down the road, during a night of drinking fine German beer, my “costume” came up in a casual conversation with three of my closest friends, including my first wife. As we talked about the amount of time and effort to look the way I did, I finally thought to hell with it, and told the group I was a transvestite (the term of the day) and I liked to wear women’s clothing. Surprisingly, no one cared and life went on normally for me even after for the first time in my life I risked it all and told someone else my deepest darkest secret. I felt like a huge weight had been taken off my shoulders, but my freedom was fleeting because of what I did in the Army. If anyone of my higher ups had found out about my secret, it could have easily caused me to have be put up for a dishonorable discharge with less than the eight months I had left to go. Which would have been heartbreaking with all the changes the Army had put me through.

As I always write about, my newfound freedom to tell anyone else about my ongoing male to female femininization project came to a screeching halt when I tried to tell my mom. She rejected me totally and sent me scurrying back to my closet as far as telling any blood family about my potential transgender dreams. The only close person to me that I knew was my first wife and surprisingly her sister who told no one. I think sometimes by coming out the way I did at Halloween parties was a plea for the public to listen to me and when I did ever transition, no one would be surprised. Surprisingly, I was so macho in my male life, nobody ever did. Including the few people who were still alive years later when I came out. All I got was surprise from the people I knew. The main reaction was that I seemed too macho to ever be a woman. 

All the changes I went through as a novice transgender woman in my thirties and forties were immense as I learned what I was really facing if I followed my gender path to my ultimate goal of living fulltime as a trans woman. I kept being stopped by blind curves and huge Ohio potholes as I learned the hard way what ciswomen must go through to live their daily lives. I had become a social person later In life and desperately needed it to continue when I went behind the gender curtain and emerged a better person. I spent so many evenings planning to be by myself that the loneliness was really getting to me before changes suddenly began to set in. It all started when a bartender at one of the venues I visited often set me up to meet her lesbian mother to have a casual drink where she worked.

We became friends and were able to see each other often until another woman entered our little group and we became a friendly threesome and gathered to watch sports on the big screens. Of all things, the third woman was another lesbian who slid her phone number down the bar to me one night when I was alone and I responded feeling much better about myself.

The most amazing experience I had was yet to come when my future wife Liz responded to an online ad I placed. Predictably, I had to sort through the ton of online responses I received all the way to being stood up on pre-planned meetings with men I met online who I refused to not meet in public. I met Liz on the other hand in one of the sites where I was advertising in a “woman seeking woman” room and she responded to me and kept responding until we set up our first date midway between our homes which were approximately seventy-five miles apart. We went to a drag show then to a Renaissance Festival and fairly soon she invited me to move in with her. That was over twelve years ago, and I surely made the right decision.

With all this social success, I need to point out again how many dues I needed to pay before I was successful. I look at it as a full circle karma payback to all the lonely times I spent after my second wife died along with most of my closest friends. I had nowhere to turn for comfort and was forced to step out of my usual social conditions to look for connections. But that did lead me right back to the old big sports bars I so enjoyed and felt at home in as a man. Again, a full circle social moment. At least, the bartenders would socialize with me if I did not cause any trouble and tipped well. At that time in my life, any interaction was welcome as I went through the biggest changes in my life.

Change is a natural part of life anyway, but it seems we transgender women and transgender men have more than of our fair share of change to deal with. To be sure it is difficult as we pay our dues to live a life as our authentic selves.

 

 

 

 

 

I Always Was a Dreamer

 

JJ Hart

I always was a dreamer and a person who thought why not me if others could do it.

I guess it all started with the parents I had who were from the “greatest generation” or WWII and Great Depression survivors. Ironically, I was taught to think for myself as long as my thoughts did not conflict with theirs. That is why I could never tell anyone in my family of my dream to someday be a woman. I needed to fall back on my default answer that I wanted to be a doctor or lawyer which kept me out of the psychiatrist’s office.

My most difficult dreams were waking up when I was still male and my vision of being feminine was just that…a vision. I had only dreamed that I was the pretty girl I desperately wanted to be. It was then that I started to play the odds that I would not be caught wearing my mom’s makeup or dresses, or worse yet get caught shopping for my own makeup in a downtown store close to where my dad worked as a banker. As luck would have it, I managed to always be clean and dressed back into my unwanted male clothes by the time my parents or my only brother came home from wherever they had been. Even though I had been able to briefly help decrease the gender pressure I felt from cross-dressing, deep down I knew I had other urges and I began to dream of what I was ever going to do about them.

The first problem I had was I had little to no confidence in my ability to present as an attractive feminine being when I tried. I was fond of thinking I looked like a circus clown in drag. And I am sure I did before I was able to come to a basic understanding of how to use makeup. On most occasions, I could only dream of the time when I could look better as a girl in my mirror and I kept playing with the odds I would not be caught and ruin my whole future as I knew it.

The playing the odds attitude helped me considerably when it came time for me to serve in the military during the long drawn out and deadly Vietnam War. Rather than serve the basic two years if I was drafted, I could have a couple other choices such as enlisting for three years and attempting to get a job I wanted to do or even join the National Guard for six years and basically stay out of the war that way. As decision time approached, I made a split-second decision to turn down the guard offer and take the enlistment offer as I hoped I could get a job in the Army that I really wanted. Which was I really wanted to continue my radio DJ career in the military which was nearly impossible to do as the Army only had sixty broadcasters in their entire system. I played with the odds and won and the three years I spent serving my country turned out to be very beneficial to me as I got exactly what I wanted. A slot in the American Forces Radio and Television Service in Thailand, then Germany.

My success in my near to impossible military profession taught me that perhaps I could be successful in my transgender dreams also. Nothing might be impossible if I only kept trying and refused to stop during my gender journey. I was naïve, which was probably for the best because I had no idea of all the stop signs, I would continue to face before I was allowed to play in the girl’s sandbox. I always knew women led a more layered, nuanced existences than men, but I didn’t know how much more different I would have it as a transfeminine person until I tried.

I knew when I started to become successful in my dream to live in a world full of competitive ciswomen, my ultimate goal might have been within reach. My presentation in the world as a trans woman was benefitted from all those frustrating hours, I spent experimenting with makeup when I was younger. The next challenges turned out to be the most difficult ones when the world (primarily ciswomen) wanted to challenge me with their curiosity about what I was doing in their world. I discovered what I already knew from my past that whatever did not kill me just made me stronger from the rare negative interactions I had with other women. I was able to learn valuable lessons on how to look for passive aggressive disagreements and recover along with the claw marks up and down my back.

Another positive was that I rarely had a wishful dream that I was a woman anymore. My feminine dreams just went to the shallow extent of showing me how my life would be if I was more attractive or had the chance of not missing all the days of growing up in the world as the girl I always knew I was. Plus, I knew I must be doing something right because none of my feminine dreams turned out to be nightmares in the real world.

In addition to wondering what my second wife would think of me now as a trans woman who has had a decade or so to fill out her gender workbook, I wonder if my parents would have ever come to accept me either. Or at least recognize the mental seeds they planted in their oldest son who turned out to be their oldest daughter after all. Somehow, the irony is not lost on me how such rigid parents could raise such a child who turned out to be such a dreamer. Somehow, I believe my dad who was a self-made successful man would have come to accept me long before my mom who I tried to come out to and was rejected years before.

Even then, she could not break my spirit or my dreams.

 

Are you Worthy, or an Impostor

 

Image from Strechath Gupta 
on UnSplash

As a transgender woman or a transgender man do you ever think you are worthy of all the contortions you put yourself through to arrive at your dream goal. What gives you the right to challenge one of a human’s most sacred basics, the gender you were supposedly born with.

To make matters worse, you have the orange felon in Washington (and his followers) oversimplifying any idea of a gender spectrum saying there are just men and women. When we know there is no such thing because we live it every day. Many of us (including me) wondered for the longest time if we are worth the time to try to handle such a inner spirit which was called a dual spirit by quite a few ancient cultures before the white Puritans got ahold of our society. Forget about being held up to be honored for our knowledge of the world, we became scorned. But that is not the subject of this post, I want to try to talk about us.

The first time when I truly faced the problem of being worthy enough to think of myself as a transgender woman was when I started to attend regular girl’s night out functions and still felt as if I was some sort of an outsider. Or, I had a strong case of impostor syndrome setting in. It took me awhile to get used to where I was behind the gender curtain, feel like I deserved to be there as much as the next woman and relaxed and started to enjoy myself. As I write about often, at this point in my life I had my second wife and male self-fighting me as hard as they could to keep me male and hurt my chances of ever achieving my dream of living as a complete transfeminine person. Without the guilt I felt and had no impostor syndrome.

What kept me going through all the resistance I was feeling was the whole femininization process felt so natural. Even with the day my wife could had left me behind in the small Cleveland, Ohio tavern venue we were visiting as two women before we went to a transgender-cross dresser social mixer. What happened was, we were sitting at the bar enjoying a drink when a good-looking man on a Harley motorcycle pulled up outside, came in and sat next to my wife and started a conversation. For the first time in my life, I felt powerless to do anything about what I was about to go through if the man offered my wife a ride on his Harley. In addition, my wife played her hand for all it was worth before she decided to not go with him leaving me behind. With no male privileges to protect me. I was taught quite the lesson about female-to-female competition when it came to men and would I ever be worthy enough to compete. Don’t be fooled into thinking that women don’t compete as much as men. They do, just on a different level of intensity at different times.

It literally took me years to accomplish what I wanted to, but I did feel I had the confidence to stand up for myself as a trans woman. In other words, I finally had been able to put the total package together on my trip out of the mirror and into the world. It felt good until I found I was not there yet and was not worthy of feeling secure in calling myself a proud transgender woman. I wanted to be more; I just wanted to be worthy of just being the me I always dreamed I could be. I wanted to be able to compete the next time my wife encountered a man she was attracted to for his attention on an equal footing. Sadly, I never could before she passed away.

To be worthy for me, also took the work of several friends I always mention who taught me so much about being a woman in the world. Primarily in the area of dealing with me. Being lesbians, they taught me I did not need a man’s attention to validate my being in the world. And I was no worse for wear after leaving the men’s club for good and greener pastures with feminine privileges such as the basic freedom to see the world like me. Being allowed to express my emotions when I needed to be a prime example.

Are you worthy can only be answered by you. I know from reading the comments I get, many of you are taking the cautious exploration methods that I took on the path to my gender goals. The method I took was certainly much slower than just tearing the bandage off saying to the world, here I am. Sometimes I wondered what that would have been like when I considered trying it as early as when I was discharged from the Army. Before I had the chance to start building any sort of male life at all. Naturally, the world was much different back in the 1970’s, early 80’s when I was discharged so I will never know what my life would have been like. All I do know was my initial exploration into coming out to my mom were dismal failures and I probably would have been disowned by my family.

Also, it is never too late to think of yourself as being worthy of going behind the other gender curtain. Male to female or female to male, it doesn’t matter. The trip is amazingly the same according to readers such as “Alex” who is a female to male transgender man. The only stable idea is the longer you wait, the more likely you are to build up more gender baggage which you will have to decide what to do with. Who knows, maybe you can find others around you who enjoy the same hobbies and interests that you do. Which is what happened to me.

The only way you can know if you feel worthy is to try.

 

 

 

 

 

The First Time

 

Image from Jon Tyson 
on UnSplash.

Like most of you, as I look back at an increasingly long life, I tend to remember many firsts I accomplished.

Of course, my gender dealings are among the top things I remember along with the first time I had sex with a girl, all the way to the first time I drove a car. I also vividly remember the first prom date I went on and how amazed I was when on the first night of basic training in the Army how many of the men around me were crying. I may have felt like crying too because the military was taking away my makeup, dresses, and wigs but I would be damned if I would cry in public about it.

Through it all, I learned the hard way to wait out the hard times and try to look ahead and not behind me for a better future. The first time I remember it happened was when we were on a long-forced march during the wintertime at Ft. Knox, Kentucky. I was feeling sorry for myself until I looked back and looked at how far I had come. From it I learned a lifetime lesson I could fall back on when I was feeling down. Which was often when I could not have any way to express myself as a feminine person by cross-dressing.

I had no idea when I resumed my civilian life after the Army how much I would have changed when I had the freedom to explore who I was. Even to the point of trying to come out to my mom. I was naïve and thought that even though I was accepted when I came out to anyone for the first time about being a transvestite (as we were called back then) while I was still in the Army, my mom would accept me also. I was wrong and all she offered was a trip to a psychiatrist rather than any understanding. So, my first time coming out to any of my family was a complete failure and the subject was never brought up again. I went back into my gender closet and slammed the door shut again. The only redeeming value I had was my closet was big enough to have a mirror to lie to me about my cross-dressing future when I needed it.

The first time I made a major step into the world as a future transgender woman was when I started to go to Halloween parties where I could express my true self. After a rocky beginning, I settled into a professional woman’s “costume” which brought me acceptance and gave me hope that possibly I could make it to make dream of living fulltime as a transfeminine person if I looked ahead and learned from my experiences.

From those humble Halloween beginnings, I began to explore a number of other firsts on my gender path. I figured if strangers were mistaking me for a woman at the parties I was going to, I would not have to wait another year to do it again and started to visit venues such as clothing stores in big malls as well as safe places such as coffee shops and bookstores. When that worked for me, I expanded my gender outreach into more challenging venues such as restaurants where I needed to interact with more people.

As I began to enjoy my time as a novice trans woman more and more, the problems of how much male baggage I still had began to cause a strain with my mental health which was already fragile. All my male life, I had tried to fight a losing battle to get rid of any possible positive male belongings that I had by moving all around to different jobs and being very self-destructive. Like runaway trains on the same track, the successes I could not wish away were coming at me from the male and female side. I could not shake the fact I had a very successful marriage, a good daughter and great job I had worked hard for so easily as I had imagined. It was the first time in my life I felt bad about being successful.

At the same time all of this was happening, I realized I was transitioning again as my transwoman self. It happened when I grew tired (again) of thinking of myself as a man who was just cross-dressing as a woman into more of a woman myself. It seemed I was facing firsts every week when I snuck out of the house to be myself. I was terrified and excited at the same time with the way my life was unfolding. I had never planned on how my life was turning out, even though I hoped that it would. I never dreamed I could carve out a new life as a transgender woman as quickly as I did.

Now I could look back on all the other first times I could remember as being important and add my series of transitions as a male to female feminized person with them. My first stable communications with other women one on one immediately come to mind as firsts. It was because I was allowed behind the gender curtain in a way I never was when I was acting to be a man. Plus, I can never leave out the impact HRT or gender affirming hormones had on my life. All of a sudden, my inside feelings and external images began to sync up, and my world softened on the hormones. Making many of my previous firsts in life seem minor in comparison. Who cares about marching at Ft. Knox when I could feel so good about myself. Truthfully though, one first led to another and made my life much fuller as I look back on it.

I never realized all the firsts were just a sign of where destiny was leading me in my life and I should have paid more attention when all I wanted to do as a kid was to be a woman when I grew up. I was always a go with the flow as a person, and the flow took me eventually exactly where I wanted to go as a transgender woman…with a lot of help from my friends.

 

 

 

Playing on the Girl's Team

 

Image from Fa Barbosa
on UnSplash.

I am fond of calling my initiation into the world of ciswomen as being allowed to play in the girls’ sandbox. But recently, I have seen it described as playing on the girls’ team. When it comes right down to it, it doesn’t matter what you call it when you have essentially given up life as you know it to transition into the feminine world.

When I was allowed to play on the girls’ team, of course there were many new things I needed to learn because I was seeking admittance to a new and complex, layered feminine existence. For the longest time as I was learning what life really was like for ciswomen, I took the easy way out by thinking all I needed to do was look the part. This is when my second wife began to mock me by calling me the “Pretty, Pretty Princess.” She was right as my presentation was advancing quickly forward and I had ego trips when women at transgender socials I went to on Long Island, New York mistook me for a real woman and wanted to see a male identification before they would let me in.

Even though I was extremely flattered when they asked for my ID, deep down I knew my wife was right and all I was trying to be was a princess. That was when I tried to begin studying the lives of women around me to discover the deeper meaning of being allowed to play on the girls’ team. Which I knew my wife would never help me with. She was busy with bigger issues such as the possibility of losing her husband to another woman which was me.

Initially, the shock of playing on a different gender team came from losing all of my male privilege such as using my size to bluster my way through life. All of a sudden, my size which I took for granted became a problem for me to disguise with the best fashion choices I could. All I knew for certain was I was told I had good legs at the Halloween parties I attended as a woman, so I tried to build my style from there. All the way to putting together my own tennis outfit even though I had never played a game in my life. Eventually, I needed to back off from showing too much leg and getting kicked off the girls’ team for not blending in and attracting too much attention to myself.

It took a while, but finally I began to realize what feminine privilege was all about and it was so much more than just having men open doors for me. Privildge to me meant I could appreciate the world around me so much more deeply. I had many more avenues to explore in the world once I escaped the restrictive bonds of living in my old unwanted male world. Other women freely interacted with me once I was firmly accepted on the girls’ team and once I learned the rules of engagement and communication, I was able to have so much more enjoyment in my life. Most importantly, I knew I never wanted to go back no matter how many stop signs I faced on my gender path.

Sadly, my second wife passed away before she could see the maturation of her princess into a fully-fledged transfeminine person. Looking back, I don’t think we could have ever stayed married but hopefully we could have remained friends while I continued to fill out my gender workbook. I finally learned I did not have to rely on her assistance to gain admission to the girls’ team because she had given all she could to help me. As with any other female, I needed to find my own way to womanhood. And even though I was not born as a psychical female, I surely thought like one and fought to be one my entire life.

As a novice on the girls’ team, I needed to earn my way also which included many bumps and bruises along the way when I learned I was much more than a cross-dresser who liked to wear women’s clothes, the mental process I went through was much more complex and tougher. To quote an old popular “Kenny Rodgers” song, I had to know when to hold them, know when to fold them and know when to run when I was dealing exclusively with other women.

Fortunately, my newfound acceptance on the girls’ team meant I needed to do very little running. No one came up to me and tried to pull my wig off in public, and for the most part I had to just deal with silence, stares and glares when I encountered a woman who for some reason wanted to hate me. There was one in particular who was also invited to the girls’ nights outs I was invited to who had a problem with me being there. I was able to ignore her for the most part or try to kill her with kindness. Finally, it occurred to me that her problem may not have anything to do with me, it may have been with the world. Maybe she resented the fact that I was happy, and she was miserable.

The more I was allowed to play on the girls’ team, the more I learned from them on the nuances of the new life I so badly wanted to live. Along the way, I never imagined learning so much in such a short amount of time. I also never thought feminine privilege could mean that much to me after I left all my male privilege behind. Especially when the effects of HRT softened my world and improved all my senses,

Whatever you want to call it, playing on the girls’ team or playing in the girls’ sandbox never mattered to me. The most important part was that I made it and rarely got any sand thrown in my face as the princess grew up.

 

We Must Be Better

 

Image from Ecaterina 
on UnSplash

Yesterday I wrote a very short post about going to the doctor with my wife Liz. During the post, I put quite a bit of emphasis on what I was wearing, just to look casual. Following the post, I received a comment from “Dana” exploring her own feelings about presenting in the world convincingly as an older transgender woman. She said (and I paraphrase) we older trans women must be better than the average ciswoman to survive in the world.

Of course, I agreed and took it a step further. Young and old, in no matter what we do, transgender women and transgender men must be better than their cis counterparts in everything they do.

It all started with me when I began to seriously get out of the mirror as a novice crossdresser and into the world. One of the first things I needed to do was upgrade my very limited fashion wardrobe. I found out the hard way; I was too heavy to attempt to find fashionable clothes for larger women like me. Immediately, I went on a diet which melted off nearly fifty pounds of weight. Which made all the difference in the world for my shopping confidence when I haunted the thrift stores for the best clothing bargains I could afford on my still limited budget.

At the same time, I concentrated on taking care of my skin by using cleansers and moisturizers every morning after I shaved. My skin did improve and I could use less makeup for a better overall effect. Through it all, I considered it a labor of love if I was ever going to present better in the world as a trans woman and not be mocked.

Finally, I did make it to a point where I could blend in with the ciswomen around me after learning many brutal lessons which sent me quickly home in tears. I found out the hard way I had to be better, just to be average and blend in with the world which was seemingly out to get me. Probably the main thing I had going for me was how dedicated I was to be staying on the gender path I was following. I always knew it was going to be rough but not as tough as it was turning out. I had a lot of dues yet to pay if I was ever going to make it to my dream of living as a transfeminine person. I thought I knew a significant amount of how women live but I had no idea of the complexity of life I was facing. Which was exactly what my second wife was trying to tell me every time she sensed me drifting away from being a cross-dresser towards starting HRT and living as a transgender woman.

What she did not tell me was, in order for me to make it, not only would I have to be average as the new person I was exploring being, I needed to be better. I was fortunate and stuck to my ideas of exploring the world around me as a trans woman mainly because I little voice in my head kept telling me I was doing the right thing because I felt so natural when I was living it. I emerged from this time in my life with a few scars from the experiences I was going through which healed quickly as I moved on to better things.

In essence, I found I could be better and carve out a new feminine life from scratch. A place where no one knew anything about my old male life and my present seemed to be more positive than my past ever was. In my way though I still had the usual male baggage problems such as an unapproving spouse (whom I did not blame), a family, and a very good job I knew I was going to lose if I did what I knew deep down I would have to do. Jump the male to female gender borders and finally live where I wanted to live from the beginning.

At the same time, I found the more complex my life became as a trans woman, the better I needed to become to protect it. On the girl’s nights out, I was invited to for example, it was key that I never went into my past very far and outed my deeply rooted male past. The example included the time I spent with my lesbian friends who would have not enjoyed any stories I had of my male past if I ever let my guard down and just blurred relevant details of my past. My willpower kept me going until I never thought about my past at all, except that it was a bad dream.

If you are on the fence considering coming out into the world as yourself, just remember to build yourself up to the point where you are the better person as a transgender woman. Perhaps then, you will have reached a place you were never able to find in your old unwanted male life. And key to the whole process is when you are feeling natural as your feminine self. By then, you will know that you have made it to a good place on your gender path. But if you decide not to go any farther, that is OK too. It is your life to live to its fullest, and your journeys into the feminine gender will have taught you so much about the need to be better.

I get asked all the time how I knew about my gender issues, and the simple answer is I always knew and refused to do anything significant about it. I was stuck in my male box from birth, and he was a powerful influence on me until I knew once and for all the only future for me was as a trans woman. Somehow, I just knew the truth about myself and quit fighting it. It was all for the better.

 

 

I've Got Someone for That

 

JJ Hart on Left, wife Liz on Right. 

Maybe you have seen the commercial on television where a group of men seemingly have an answer for a friend who can solve a certain problem. To a point, then they are all stumped on what to do.

I saw the commercial again this morning and applied it to my path to living a transgender existence. My basic idea was, I did not ever have someone to provide guidance in all my gender issues. In the pre-internet days, which I write about often, I needed to rely on publications such as “Transvestia” or “Tapestry” for any real information on having someone to help me understand what I was going through in my life. I was overjoyed for awhile when the magazines helped lead me to actually meeting in person others at cross-dresser-transgender mixers which were close enough to me so I could attend. Surely, (don’t call me Shirley my name was Karen back in those days) I could meet someone there who I could explain my gender issues to and feel as if I had someone to confide in and help me.

In reality, even after I went to the social mixers, I still did not come away with feeling like I had someone to be my friend. No matter how you defined what the publications called me. A transvestite or a cross-dresser, I just knew I was different and still belonged in the group of men in the commercial who were stumped on what to do. That defined the new groups I was meeting for the first time.

Since I could not find a friend at the mixers, I withdrew into myself and did the best I could cross-dressing and dreaming of a better day in front of the mirror. I was stubborn and kept on attending socials until I began to be invited to smaller parties at a house in nearby Columbus, Ohio. The parties were very diverse, and I learned a lot from the others around me and even developed acquaintances who shared my gender path. Or so I thought because a few of them took a sharp curve away from me and went as far as having gender realignment surgery. Back in those days when you took such a radical step, you were expected to leave your past totally behind and start all over again and I started to drift away from them. Very soon I was stumped again and very confused on where I was going as a transfeminine person.

The only thing I knew for certain was my sexuality did not change when I entered my feminine world. I even was attracted to the very few lesbians who were attending the parties I was going to, and often we would briefly leave to visit other lesbian friendly venues in Columbus. At least it was one small feeling I knew I could count on.

Through it all, I did have someone who was my second wife. On many of the party nights, she would accompany me which sometimes was bad and sometimes it was good. She was the one who saved me from being trapped in a small hallway by a huge admirer one night, which was good, and other nights her presence hindered my ability to expand and test my feminine personality. Sadly, I learned more about myself when she was not around as I considered her my best friend most of the time. She was not the person I needed all the time though, which created huge problems in our long-term relationship. She always knew I was a cross-dresser but drew the line if I drifted towards any of the transgender women at the party.   

At that point, I did feel like I did have someone who understood what I was going through at the party but had the feelings rejected at home. The worst part of the whole thing was, I had gone too far with my transfeminine experimentations to ever turn back but I tried to have the best of both worlds. Save my marriage on one hand and live a part time life as a trans woman on the other. I still carry the guilt coming from the number of times I broke my promise to my wife and left the house dressed when she was at work. I have always described it as cheating on her, with myself.

One way or another, I was gaining confidence in my feminine self to continue to build a new life which felt so natural because for a change I had someone to lean on. For those of you who don’t know, my second wife passed away suddenly from a massive heart attack leaving me with a huge hole in my life along with a truck load of guilt which I could never make up for.

In her sudden absence, I fell back on the only person I knew who could help me as I decided to end my male life for good and live out the remainder of my life as a trans woman. It turned out all the labor of love I put into my femininized life came back to help me because I had all the hard work of refining my presentation behind me. I had a working knowledge of what to do to survive in the world of alpha ciswomen. I just had to refine my new life to a point where I could thrive with new friends. When I had reached new milestones in my life such as HRT hormonal changes, I was met with welcome to our world and knowing smiles rather than masculine scowls and glares. I loved my new life.

The only problem I had was I took too long to transition across the male to female gender border. It turned out I had someone all along to help me if I ever gave her the chance. I was stuck in the good old boys’ male privilege club way too long and it was hard to give up. Once I found someone like my wife Liz to point out the obvious to me, I knew for sure I had that special someone and I could live an authentic life as a transgender woman.