Just Another Lonely Day

Image from Jarge Johansen
on UnSplash.

Throughout most of my life, I was desperately lonely, as I had no one to fall back on as I explored my gender issues.

Growing up in a rural area, I started with just a
small circle of kids I interacted with and it rarely grew significantly, so again I was stuck with why I felt the way I did about myself. All I knew was I had a difficult time interacting with the boys at all and the girls seemed as if they were some unreachable magical creatures I knew nothing about.  While all of this was happening, all I could do was carve out my own little world where I was a pretty girl in front of the mirror in mom’s clothes and makeup.

Little did I know how those humble cross-dressing beginnings would come back to influence my life later. In fact, forever. As I grew, I became more skilled in using makeup and finding clothes which I could fit into when I outgrew moms. Then, the more I cross-dressed, the more I wanted to. Which did nothing for my extreme loneliness. It seemed to me; I would never find a way out and really did not until I hit my late high school and college days. What happened was, a group of girls at high school learned that a friend of theirs did not have a date to the junior prom and I did not either and matched us up for the evening. After a successful date, I was not so lonely when another friend of mine set me up with a single girl he knew and suddenly, I was a socialite as I entered college. In truth, deep down I was still the deeply conflicted person I always had been.

Amazingly, my early college years were so intense that I forgot about my gender issues for six months or so before they crept back in. When they did, they became as intense as they were before I left for college and stayed that way until they were put on my back burner when the military draft caught up to me when I graduated. For a while I was engaged to a woman I knew from college until she left me just before I was due to report to Ft. Knox for Army basic training leaving me completely alone again. When my fellow soldiers were getting mail from wives and girlfriends, I was getting an occasional letter from mom. At the least, I appreciated her efforts and once again I was back to being used to being intensely alone.

All along I wondered what my military time would do to my gender issues. Would they go away temporarily like they did in college or not was my question. The answer I was looking for did not take long to become evident to me. No my gender dysphoria was not going away and in fact, tools I had learned in the Army just made my dysphoria stronger. For example, I became more confident in myself as I had a better idea of what I could survive and I spent hours of what spare time I had daydreaming of what I would do with my feminine self once I had served my three years.

It was not very long after I was discharged that I gathered the courage to ask my first wife to marry me. Since she was in the Army too with me for over a year, she had witnessed my Halloween party costume at a hospital party we had went to with friends. Plus, my later confession to three friends plus her that I was actually a transvestite and my costume went a lot deeper than it looked. She also turned out later be the mother of my first and only child and the marriage did last several years until I fell madly in love with my second wife.

Oddly enough it was another Halloween party which allowed me to confess to her my deep dark secret that I was a cross-dresser. It turned out that she did not care which was the case for the twenty-five years we were married. Until I began to transition into a transgender woman. Just before she passed away from a massive heart attack. During those years we had our share of good times and bad times somehow, we always made it through, and she never knew how much of a role model she was to me when I went my separate way as a trans woman. Following her untimely death at the age of fifty.

When she passed, I went into a lonely shock I had not felt through the majority of my life. I could not understand why I was having to start all over again in my mid-fifties and search for another relationship. And furthermore, which direction would I take with the gender issues I had during my life. By this time, I was well ahead of my goal to possibly live as a transfeminine person. I had major decisions to make in my life, so I kept on searching for answers. To start with, I tried dating ciswomen again as a man which failed miserably and at the same time, get more serious in my explorations ss a trans woman which I found to be a natural social release for me.

By the time a couple more years of wasting valuable time went by, I was sitting by myself enjoying my new company and I thought why was I not living like this all the time? How stupid could I be not to take advantage of what I had learned in the world so far as a transgender woman. Most importantly, my lifetime’s dream of living as a woman was within reach, and I was not taking advantage of it.

From that point forward I put together a timetable to give away my remaining male clothes and pursue HRT therapy. There would be no turning back from that point forward. I was tired of the gender struggle and loneliness I was enduring. I was afraid if I did not make the change now, I never would have the chance.

You might say I played the odds and they came out in my favor but on the other hand, I researched the odds extensively before I did it.

 

 

 

I Wish I Knew Why

 

 

Image from Jon Tyson
on UnSplash

It has been a while since anyone has asked me when I knew I was transgender. In fact, it was several years ago when one of my grandkids was coming out to my daughter as being trans.

My daughter then asked me if I had always known, true? I told her yes that was true except in the exceedingly early days of my life when I knew something was wrong with me but I just did not know what. As I grew older and I experienced that first magical visit to mom’s clothing drawer did I truly knew what the problem was. I really liked the feel of mom’s clothes and that was only the beginning as I wanted to be a girl full-time sometime in my life. Just the buzz of wearing feminine clothes was never going to be enough. So, I set out on a long journey to see if I could ever achieve my dream.

When I was able to begin to interact with others with gender issues, I found early on that it was not going to be the end to my questions that I thought it could be. For example, I was too much girl for many of the cross-dressers I met and not enough woman for the then called transsexuals I encountered in person at the social/mixers I traveled to. The closest ones initially were nearly a two-hour drive away before mixers were then set up in a nearby central location for me. It was then that I was able to meet others who identified as true transgender women and I fit in perfectly with them. Finally, I began to have answers to my identity as a person.

Of course, I needed to take all sorts of side journeys as I sought out the key to why this transgender world had chosen me. In my research I even came across the theory that the drug “D.E.S” which was given to women with a history of problem pregnancies around the time I was born, could conceivably be linked to a person having= gender issues later in life. Because to ensure the fetus went full term in the womb, the womb was flooded with estrogen to aid the birth process. I thought “D.E.S.” might fit me because my mom had suffered through three still births before I came along. Ultimately, “D.E.S” stayed just as it started with me. Another solution to an extraordinarily complex gender problem with no concrete answers.

Then there was the victim mode I wrote so much about when I went through a poor, poor pitiful me time of my life. I could not understand why I needed to be stuck with all the gender issues I had when no one I knew had them either. To this day, I envy men who have been able to go through their lives as men without the added distraction of wanting to be a ciswoman. Finally, I made the difficult turn considering my overwhelming desire to be feminine as a good thing. Because it set me off from society as a unique person with a look at both sides of the gender border. Removing my victim mentality made all the difference in the world to me as I began to look ahead for the possibilities which laid ahead. Rather than always looking over my shoulder and dwelling on the mistakes I had made.

The more success I experienced when I first was able to carve out a new life for myself as a transfeminine person, the more the wish I knew mentality I had lived with my whole life began to fade away. From that point, I went into my confidence mode because without it, I was powerless to do anything I wanted to do as a trans woman. I found that as long as I held my head high and did my best to be a quality person in the world, the more people left me alone since humans are like sharks. They sense blood in the water, and I was not adding any of mine. Confidence also allowed me to try different things. To judge if I really wanted to jump the gender border and give up living life as a man altogether. Even though it was the most difficult decision of my life, having even a sliver of hope that I could live my dream that propelled me forward to a gender tipping point that so many ask about.

This time, I could tell anyone who asked why I decided to leave a successful male life to take on a decided uncertain one as a transgender woman. The answer I always gave was deceptively easy. I had reached my own gender tipping point where I was living more as a woman (and feeling natural doing it) and less as a man as I was feeling increasingly uncomfortable doing it. By doing as much research as I had, I had given myself no choice as what I should do. When became now and that was the time, I decided to take the next step and pursue gender affirming hormones or HRT to sync my inner mind with my external body the public saw. I knew it was the point of no return for me as my body took to the new hormones magically.

I knew from there that all my explorations as a trans woman pus the addition of HRT allowed me the most powerful female privilege of all. The power to finally be myself. The wish I knew why I was different my whole life was answered with a resounding yes, I did know it all along and refused to face my own truth. I was living a counterproductive life as I was going overboard trying to be successful as a man when I was a woman forced into her shell all the time struggling to get out. The best part was when she said I told you so, as she destroyed what was left of my old male ego.

I finished strong when my why me became a why not as I had the chance to live my feminine truth among the ciswomen of the world.

Thanks for reading along and I hope you will discover your why me in life! Comments from you are always welcomed.

 

 

 

 

It Was Exhausting Waiting for the World

Dustin Hoffman in "Tootsie"

 Over the years, it was exhausting for me waiting for the world to catch up to me.

As I always mention, I was born into the pre-internet and social media years when information about any gender issues was difficult to find. I am old enough to remember the sensationalized reports on television in Dayton, Ohio when the police staged raids on “homosexual” venues and I saw them arrest men dressed as women.

In addition to the negative publicity I was watching, I knew from my limited research from books at the library, that cross-dressing was considered to be a mental illness which I did not feel was true with me. I was not mentally ill, I just wanted to be a girl, and it was simple as that. All it did was put extra pressure on me to never be discovered by my family or my brother in the feminine clothes I had found.

I felt so all alone as a “transvestite” as we were known back in those days until my second wife and I purchased our first home computer. Which opened a whole new world to me including a way to contact others with gender issues such as me. Before that, all I had were the “Transvestia” Magazines I subscribed to and the “Tri-Ess” social mixers I drove hours to get to. I could not believe the world was suddenly at my finger tips when it came to discovering others outside of the “Tri-Ess” community.

All went well, until my second wife caught me in one of the old “AOL” chatrooms having a private conversation with another cross-dresser in a nearby city. I needed to learn quickly on how to cover my internet tracks better if I was ever going to stay out of trouble. The world was not catching up to me as I was catching up to it through the power of the internet. Then 1982 rolled around along with the classic gender movie of all time, “Tootsie” with Dustin Hoffman in the lead role as an actor who lands a soap opera job playing a woman with life changing experiences. For once, there was a film which did not portray a man in a dress as a criminal up to no good and I could not wait to see the film.

With the resultant good publicity which came from “Tootsie” I thought that maybe the puritanical gender ideas of the country would have changed and the public somehow would be more receptive to cross-dressers and transgender folk forever. Of course, I was being naive and over time, the public shifted back to the same old place it had always been…not accepting to people with gender issues like me.

Sadly, I had to go back to carving my own path as a novice transgender woman on my own without the publicity of a movie to help me, including the daytime talk shows which were the new television craze. It seemed to me that every week, one of them featured something about a cross-dresser on their show. In all fairness, some productions such as “Phil Donahoe” tried to present a fair view of our culture while the “Jerry Springers” of the tube just sought to sensationalize us. So, once again, the world had not caught up to me at all and did not help me when I needed to carve out my own life for a change in the world. I did not want another ciswoman thinking she was talking to a future “Jerry Springer” person, and I was real and down to earth. I was just trying to live a normal down-to-earth life like she was.

By this time, I had given up on the world ever catching up with the complex lives that transgender women and transgender men lead. It is why unless you are a very open person and secure in your world, you will never understand where we are coming from. That is fine, you do not have to understand, just do not try to stand in our way as we try to live.

Now I worry that all the fragile transgender rights we had gained under recent presidential administrations in Washington will be erased to an extent it will take decades to ever get them back. Then, I will have lived long enough to go from the “Tootsie” era of understanding to the “Orange Clown’s” world of rejection of our right to even exist. An experience I never wanted to have, and it is even worse here in my native Ohio where the state recently revoked their gender change requirements for driver licenses. So as they used to say back in the day on Top 40 radio stations the hits just keep on a coming.

Every once in a while, I hear rumblings from the regime in Washington trying to do away with my gender care through the Veterans Administration. So far (knock on wood) I have been part of the program for so long, and it is tied to my depression issues I have flown beneath the radar, and I hope others can too.

As a tribe, transgender folk have always existed through time, and if you are just realizing your potential as a trans person, welcome to a scary yet exciting world where you can be yourself. At least you can fall back on the resources you can find on the internet to help you and bring a little light into your dark closet you have been in for so long. Just remember not to let the brightness of your new day blind you to your new reality.

In the meantime, the world has caught up to you in your own way. Enjoy it because you have endured so much to get here.

Thanks so much for joining me in my lifetime of gender trials and tribulations! I set out to help anyone I could, and I hope that is you! All comments are welcome.

When My Tomorrow Became my Today

JJ Hart

My desires to always look like a pretty girl early in life led me to always be a tomorrow person.

 I always thought that somehow tomorrow I could get a real wig, nicer clothes and more makeup which would help with my feminine transformation. I guess you could say that the whole process made me into quite the dreamer as I sat in school and envied the girls around me in their pretty clothes I could not have. At least today but maybe not tomorrow if any of my dreams came true.

Soon I discovered that dreams never came true on their own and would take an enormous amount of work on my part to make a dream happen. Especially once as complex as crossing the gender border to live a transfeminine life. I often wonder if I would have had an ounce of foresight into how difficult I was going to have it; would I have ever undertaken such a crazy path to begin with. One which would completely consume all the spare energy I could use.

The first problem I had to conquer in my feminine life was my often-frustrating attempts to look like a woman and not some sort of a clown in drag at the circus. I found I was setting the bar way too high in my appearance standards as there was never going to be a day when I could match the prettiest women I envied. I just needed to blend in with the rest of the ciswomen in the world just going about their everyday lives. It took me many painful attempts at presenting properly as a trans woman before I got it right and was able to move around in the world without causing any undue attention to myself. When I did, I was happy to stay in the present until my brief gender euphoria went away. As I crashed from the euphoria of living as myself, I was bitter, nasty and tried to take my frustrations out on the world of ciswomen around me. Why could not I be like them and live in their world held me back in mine, so I kept dreaming about the next time I could I could live my dream in the world fully cross-dressed as a woman.

The good part was that all along I was becoming better in my presentation as a woman and was finding it easier to cross the gender border. The bad part was once I did it, I wanted to stay and not go back to the male I was living. It was then that my todays became longer, and my tomorrows seemed further away. My new mentors became the established transgender women I had met at the socials I was going to in nearby Columbus, Ohio. They had crossed border and were living successful lives and I wanted to learn more about how they did it. What I learned was that every trans person’s journey was different and it was rarely ever easy. All I ever knew was that every time I was accepted into their circle, I felt natural and wanted to learn more about them.

As I look back on it, the one thing the mentors had on me was their natural beauty which I never had, so I had to keep putting my tomorrow off until I found out I could do a male to female transformation my own way. Or out of sheer willpower as I had a transwoman friend of, mine tell me in a straight bar we were in one night. By this time, I had given up on any natural feminine beauty I might have and made my tomorrow become my today by using other strengths ciswomen bring to the table when they don’t happen to share the extreme passing gene that some women have. They go on to lead fun and fulfilling lives by tuning out all the demands to be beautiful they hear. That is what I had to do because for sure ciswomen come on all shapes and models and I could certainly find a group I could fit in with. Which in my case, happened to be lesbians.

I was really seeking out the company of lesbians so to speak; I just happened to stumble across their culture at a small lesbian venue I started to go to as well a through a bartender at a big sports bar I used to go to who introduced me to her mom. Through it all, I knew the next step for me was to become more feminine by using HRT or gender affirming hormones. My approval to take the hormones focused my tomorrow so much I could not wait to get there. I changed during the time I was socializing with my new lesbian friends who took me to watch sports as well as big lesbian mixers. I was having the time of my life as my tomorrow was rapidly becoming my today.

Maybe most importantly, my friends helped me to validate myself as who I was really was as the subject of my past life as a man never came up. They did not want to know, and I did not want to bring it up as I was just appreciating my spot in my new present as a transfeminine person.

The final touches in my today came when my daughter accepted me totally and I met my current wife of over a decade Liz. They helped rid myself of any lingering doubts of how I should live my life. Over my gender cliff I went into their soft arms and my gender tomorrow was gone for good.

My only passing regret was that it took me so long to face up to who I was always was as a full-fledged human being. There was no way I should have let it go as long as I did, I should have let tomorrow be my today. I was all wrong as I tried to cross-dress my pain away. My excuse is I was jinxed all along into leading a backwards gender life thinking I was a man trying to be a woman rather than the other way around. That way, I would have never let my todays and tomorrows get mixed up the way they did.

 

 

Being Accommodating...Not Intimidating

 

Image from Billie
on UnSplash.

Being accommodating versus intimidating was very difficult for me as I transitioned from male to female.

It was all part of learning a new feminine world and escaping the male bonds I had suffered so long from. What happened was, I was thrust into a male dominated world in which if I was ever going to survive, I would have to play the intimidation game of life. That way, I could stand a very good chance of keeping the bullies away as I matured. It did not hurt that I developed into a larger slightly above average sized male person (which I hated) but again when I added sports into my life’s mix kept the doubters away from my masculinity. In fact, I needed to play that intimidation card well into life and used it before I transitioned into a transfeminine world. Intimidation became easy to use for me, and I counted it as one of my male privileges even though I stopped short of ever being a toxic male because I respected all women so much. But it worked well with the male kitchen crews I needed to manage in the busy restaurants where I worked.

The problems began with my basic personality outlook I had been forced to live so well when I began to try to join a world which was largely controlled by ciswomen, not cismen as I always thought was the case. Women just found unique ways always to work around males and their drama. And here I was in the middle of a new world just trying to find my way successfully.

I felt it most intensely when I was forced into communicating one on one in the world with other women. I found I was unprepared and initially just tried to keep my mouth shut, which turned out to be exactly the wrong move to make. Here I was trying to make new friends in a feminine world without talking? How was that going to work. It did work. In exactly the way I did not want it to. If I did not express who I was, the other woman I was trying to communicate with just assumed I was being standoffish or in some way stuck up which was the last thing I wanted to do. So, I immediately trashed my male scowl and quiet behavior as a form of intimidation to keep people away and went to a more open form of interaction with the public which invited people in. In many ways, it was one of the most intense and scariest things I ever went through in my life. I was in uncharted territory for sure and even resorted to feminine vocal lessons to help my progress.

And then there was the experience I had with a small girl who startled me in a clothing store I was in. She ran around a rack of clothes and almost hit me and went running back to her mom saying something about a “Big mean woman.” Immediately I was relieved that she got the woman part right but right then and there decided to do more about the old male intimidation factor I was obviously still carrying with me. In no way did I want to go around scaring little kids.

Life went on, and so did I as I started to feel more secure in my new role behind the gender curtain. I learned that many ciswomen were just curious about who I really was in a world in those days dominated by day-time sensational talk shows such as Phil Donahue and Jerry Springer. Here I was. The real deal cross-dresser or transgender woman right in front of them to talk to and know that I was just a normal person like them after all. It all happened because I had the courage to let them into my world and turn my old male intimidation ideas off for good.

Perhaps the most intense topic in the intimidation versus accommodation discussion came from my initial introductions to the women’s restroom. It was the exact opposite from the men in many ways except the obvious. In the men’s room, you were expected to never make contact or acknowledge another man while in the women’s room just the opposite was true when a polite smile or greeting was the proper way to acknowledge another woman. It took me a little bit of time to get used to the change, but I did it quickly because I wanted to earn my women’s room privileges desperately. For obvious reasons, I was drinking a lot of beer.

I see intimidation versus accommodation as just another step in acclimating yourself into the feminine world. But you have to do it right to be accepted. You must be yourself behind the gender curtain you choose without becoming a doormat. As an outsider to transgender men everywhere, my thoughts are it probably is more difficult to assume an intimidation role in a male world. On the other hand, accommodation in the female world I was in was always an easier path for me to take. I just had to understand and react to anyone who was setting up to take advantage of me. I came away with plenty of claw marks up and down my back from unfortunate experiences I had in a new (to me) passive aggressive ciswoman world. I learned often that a smile meant nothing in most situations when another woman was just sizing me up.

In the end, the whole experience just boiled down to very important experiences I needed to learn to finally make it out of my closet and into the world as a transgender person that other people would like to know and often my smile was the beginning of that process instead of my stay away old male scowl. The fun part often was seeing the results from the amount of learning I needed to do in my stubborn head to make it happen.

As always, thank you very much for joining me along my gender path and I hope you gained something from my mistakes. Any comments are always appreciated!

 

 

 

 

I Wanted it All

 

Image from Sindy Sussengut
on UnSplash.

During my gender journey through multiple transitions from cross-dresser to transgender woman, I have been selfish and wanted it all.

It all started very early when I was experimenting with mom’s clothes and makeup when I had the first idea all that I was doing may go deeper than just wearing feminine clothes. I did not have the terminology or knowledge back then to work my way through it, but in reality, I was discovering I was more transgender than anything else. In the years to come, that would be a major point to think about along my gender path.

As I grew through my first two marriages where both wives knew of my cross-dressing desires, my first wife was far less demanding than my second and on numerous occasions during fights we were having about me, my second wife rightfully pointed out that our relationship was not all about me. Since I was in the middle of an obsession with my appearance and all things related to makeup, as I said she was right and I was needlessly selfish about our relationship. She was far wiser than I and knew even at that early time in our marriage, her husband was slipping away.

Even though I loved her dearly, I still could not stay away from the powerful draw of wondering if I could ever achieve living fulltime as a transgender woman. Deep down, I knew my second wife would never come with me on my journey as she made it abundantly clear she never signed up to be married to another woman.

With a lot of work and repetition, I did finally get better with my wardrobe and makeup and then needed to figure out how to sneak out of the house and get into the world. It basically meant my imagination had to go into overdrive as I tried to think of reasons I needed to explore the world as my new true transfeminine self. Even if I was not sure what the word meant back then. I went as far as going to the grocery store for my wife who was working on the days, I was off and combined the trip by going to a nearby big box store to shop for panty hose and makeup. My biggest takeaway came when I noticed very few people were noticing me and I started to think I wanted to experience more. My restless feminine spirit was dominating me again.

At the same time, I was doing all of this, I was still searching for my dream job in the commercial restaurant business and after switching jobs and locations several times, I finally did. As I finally broke free of my fast-food background and landed a job with “Chi-Chi’s” Mexican Restaurants in the Columbus, Ohio area where I had ties to. It was a win-win situation for me because I was back home again and could start to interact with the diverse small LGBTQ group that I had known from years previous. This was the tight knit group that had several transgender women who were on their ways to gender realignment surgeries, and I could pick their brains on what it meant to do it. Even though, I did not have the resources or the willpower to consider such a radical move for me in my future, Just being considered as an equal in their group was good enough for me…then.

I say “then” because in life everything rarely stays the same. As I continued to break the vows I had with my wife, I kept going out to venues from the house and began to actually carve out a life as a transgender woman with people who had never known my male side. Wanting it all was staring to mean so much more to me than ever before as my male life began to slip away from me and wanting it all increasingly meant an ongoing break with my long-term marriage of over twenty years. Because she was not giving into her demands, and I was discovering just what mine should be if I was willing to risk it all to live my dream life. Sadly, it would have to be all me to do it as I tore down everything I had worked for as a man to start over in a woman’s’ world.

Sure, I was scared to death as I decided to keep concentrating on the feminine me who had waited so long to live her life. But the whole process and path I was on felt so natural, I decided to be selfish and continue it. By proceeding along the path I was on, I needed to take several abrupt detours when I had problems with deciding my sexuality all the way to just basically communicating with the remainder of the world I was in. Which I discovered was made up of ciswomen not so unlike my second wife. Many were strong and sure of themselves and set up forms of communication which were totally foreign to me as I was coming from a male world. Suddenly, I needed to adjust to forms of non-verbal and passive aggressive communications which were reserved for use when cismen were around.

Perhaps my best selfish move I made was to be approved for gender affirming hormones or HRT which enabled me to come closer to my transgender mentors of so long ago. Since I had ruled out any surgeries, the changes from the hormones would be as far as I could go to sync up my female mind with my male body.

By this time, my wife had passed away and there were very few people left who knew the old me at all. So, I was mostly all-alone with my new emotions and bodily changes such as hair, breasts and hot flashes. When I reached out to any of my lesbian friends, all they would say was welcome to their world. Little did they know how badly I wanted to be there. I was rewarded by the fact that the people who knew the male me told me they thought I was much more relaxed and happy now.

Since I can now love more deeply than I ever could as a man, my life has come full circle to encompass feelings I never knew I had before. All because of my selfish one sided past to get here. I wanted it all and finally was able to find it.

Thanks for reading along and I would be remiss if I did not mention two things. Thanks to Grace Ann Hansen for publishing my stories in her “Empowered Trans Woman” site!

And sadly, I would like to mention the passing of a true icon, Dolly Parton who was a staunch ally of the LGBTQ community. She will be severely missed.

 

 

 

 

I Was Risking it All

 

Image from Leo Visions
on UnSplash.

In many ways this post is an extension of yesterday's explanation of me never really having a plan b as I traveled up and along my gender path to transgender womanhood. The essence of what I wrote was I did not have a real plan if suddenly it was evident I was not going to make it to my dream.

I was taught to be a dreamer by the unrealistic expectations my parents put on me. Whatever I did was never good enough and often sent me back to hide in my dresses, hose, and makeup. The only place that my impossible dream of being allowed to be feminine could become a reality. If only for a short time. I don’t know exactly why, but the gender dream I was pursuing so well was the only dream I wanted to become a reality as I did just enough to have good grades in school and played just enough sports to keep the bullies away.

Cross-dressing was always a risk because back in those days (the 1950’s and early 1960’s) gender issues were considered to be mental health problems, and I knew that did not describe me. On the other hand, I did not want an impromptu visit to a psychiatrist to tell me about myself and how I should be treated. Fortunately, that mental health visit never happened as I continued to risk my existence on some sort of a high-wire act which if I ever fell, life as I knew it would fall with me.

Of course, as it always does, life became much more complex as the years flew by. As my cross-dressing became more presentable, at the same time, I had college demands and a military service I never asked for to deal with during the Vietnam War years. All this time, I was learning what it meant to risk it all in my life and somehow still succeed. As even though my gender issues were put on hold for a long three years, I learned valuable lessons from the Army on how to attempt to deal with my dream which was on hold. At the least, I learned from the military how to deal with a structure I had never had before as well as other issues that would take another blog post to deal with.

When I was discharged from the Army, I gained my first and only child and my life became even more complex. What could I do with a child to deal with if I wanted to risk it all to run away and live a transfeminine life. Dealing with everything else for me became easy when I had a family to provide for. Any alternate plans I had for my future were delayed again along with any hope of ever making it to my dreams.

What suddenly came along to help me was when the internet took hold of the world and I was introduced to people just like me I could reach out to and even meet. All because of the first in home computer my second wife and I purchased. By participating in the first chat rooms of the time, I had my first taste of what it meant to be a transgender woman and not a parttime cross-dresser as well as sampling my many layers of the gender spectrum I never knew existed. The one big thing the computer did for me was that it taught me how badly I wanted to test out the new world I had discovered for myself and see where it took me.

I also learned quickly that it was easier said than done. Mainly because when I left my safe closet mirror and jumped into the harsh reality of being a trans woman in the world was not going to be as easy as I thought. I needed to quit dreaming of what I thought I should look like and begin to expend all my time and money working on how to survive in a world where ciswomen run the show. Sometimes up front and most of the time behind the scenes which I came to call the gender curtain. I found out the hard way, that to not be rejected in my quest to make it behind the curtain I would have to eventually risk it all in search of the new, exciting world I wanted to live in.

I am not a poker player at all, but I knew I would have to push all my chips to the center of the table to see if I could ever win my goal. The problem remained that my male side was still acquiring more chips with his new more demanding job. Here I was stuck between two genders trying to rule each other and the male side was materialistic, and the female side was more natural and felt like I was doing the right thing for the first time in my life. All the turmoil resulted in was destroying my already frail mental gender spectrum health. It tore me up as I had to constantly be aware of which gender I was on any given day.

As I said, eventually my feminine side won out as I chose feeling more natural in the world than I ever had as a man. He had been reduced to a shell of his former self by being able to shed his male privileges he earned but never wanted. In its place I gained the greatest female privilege of all…the freedom to experience the world as a trans woman myself. It took a while but all the dark downtimes I experienced on my bumpy gender path made me a more resilient trans woman with a unique understanding of both sides on the main gender binary.

I cannot imagine what would have happened if I had lost that gender poker game so long ago because I was living such a miserable life. Plan a was to always live as close as I could to a woman. It took me decades of life (5) to get there, but I made it.

 

Stepping Out as Yourself

Image from Max Anderson
on UnSplash. 

Stepping out into the real world and leaving my closet and mirror for the first time was difficult for me. For lack of a better term, I was leaving everything I worked for in my male life behind.

As much as I hated my dark, lonely gender closet, I found it to be a safe place to be when I needed it the most. My ability to put on a dress and makeup soothed my soul, if only on a temporary basis helped until I needed to take another high heeled step into the real world where I so desperately wanted to be. To put it mildly I was scared to death when all my male privileges I had worked so hard to learn were stripped away and I was starting all over again. It was different when I could not rely on a menacing facial expression or an occasional bluster to get me by.

Stepping out into a new feminine world for me meant I needed to immediately begin to work on building a new personality which would grow with me as I worked my way towards my dream goal of living fulltime as a transgender woman. This was the same period of time that I was obsessed by my feminine appearance, so I had a lot on my mind. As I struggled day to day about what gender I was going to be. All too soon, life meant so much more to me than buying a new dress or skirt all the way to how I needed to change my old male movements when I wore them.

As I was forced by being in the public’s eye, I needed to understand exactly what I was getting myself into. So much more than the pretty clothes that I saw the girls around me wearing. If I needed to be more like them, I had miles to go on my gender path to get there. All I knew was at that time, most of the ciswomen I encountered were nice to me. Every little bit helped me learn what my future could be like if I kept stepping out and away from my old male past. Plus, problems kept occurring with my second wife and my male self who saw the changes in me as a threat to their future lives. My second wife saw her husband slipping away and my male self-saw his whole future gone if what I was doing continued.

Through it all, I was able to establish myself as some-sort of a successful cross-dresser before I transitioned into a transgender woman one fateful night when I thought enough was enough and I had to do more to continue up my gender path. Before I became lost entirely and had to reassess where I was. What I learned was that I was actually further along towards my transfeminine goal than I thought I was. I learned the hard way when I was able to be successful when I went out for the first time to enjoy a drink with a group of ciswomen from a nearby mall who just would go out and socialize after work. It was something I always had wanted to do as a transwoman, and I was amazingly accepted into their circle. I guess you could say that night I really stepped away from my old male self and loved it.

Before I knew it, my new shiny shoes (flats this time) were stuck in gender quicksand as I had stepped into a place that I never wanted to get out of. One thing was for sure, if anyone came along with a rope trying to rescue me, I would have turned them down. I was having too much fun challenging the world as my new transgender self to ever turn around and go back to a boring life as a man that I had stepped away from.

Sure, there were still many times that either I was scared to death of where I was going or was out and out rejected by the world, but those times were getting fewer and fewer apart. I was headed towards my dream goal which was slowly coming into focus as a doable project. I say project because I had never attempted such a thing as jumping the gender border to slide behind the gender curtain in my life. When I finally accomplished my goal of being allowed to exist in so-called women only spaces, I certainly was not going to give up all that I had earned.

By this time my second wife had passed away, and my old male self was seeing the writing on the wall, and his days were numbered too. Which left me all alone to make my key life choices. Still after much thought and consideration, I finally gave in totally to my feminine side, and I set out to build a different yet better life with my new ciswomen lesbian friends. All of them helped me round out and refine the woman I always wanted to be. Most of the work I had already put in, so I did not have that far to go. Mainly the only place I needed to go was with my dealings with men. Even that turned out to be relatively easy because most men left me alone because I was not attractive enough or just wanted me as some sort of a fetish object. All my problems went away when my lesbian friends taught me I did not need a man to be validated anyhow.

As stepping out as a transgender woman in the world became natural to me, a whole new universe of life came alive for me. Especially when I was approved for my long-term dream of starting HRT or gender affirming hormones. Something that my second wife always recoiled at the idea of, but on the other hand, my current wife Liz loved. The essence of being on my hormones just carried over into me stepping out into a new world with confidence I had never known before.

 

 

 

Letting Tomorrow take care Of Itself as a Transgender Woman

 

Image from Valentina Conde
on UnSplash.

Since I was always a person who had a difficult time living in the present, tomorrow always loomed large in my mind.

I think it all started when I began to rebel against the masculine world I was being forced to live in and always thought tomorrow could be better. It turned out that all the wishing and hoping I did for a better tomorrow turned out to be wasted time and energy, I finally needed to take matters into my own hands, stay in the present and do something about me being stuck in my dark, restrictive, gender closet with only a mirror to help me.

It took a quantum shift of thinking on my part to even thinking about how I could change my life. First of all, it was nearly impossible for me to quit daydreaming about the next time I could cross-dress in my mom’s clothes and try on her makeup. Any time I was not actively being engaged in male activities, I was hoping that soon I would be glimpsing a view of me in a favorite miniskirt I had found by accident at school outside of the girl’s locker room. If the girl who left it behind did not want it, I certainly did before a janitor found it and threw it in the trash. I was overjoyed to add it to my small but growing feminine wardrobe at home. Hopefully away from any prying eyes who may find it.

Somehow, I managed to hide my “treasures” away and add to them with my own meager funds I had earned from my rural newspaper route and from chores I was doing around the house. I will never forget the excitement I felt when I found a pair of women’s shoes that fit me in the department store where I was sneaking in to buy my makeup and panty hose. The whole process made me feel good because for once I was not relying on anyone else to help my cross-dressing along. It all was just me, and I was in the present doing it.

As I moved along in years and experience, I increasingly wanted to break out of my dark closet to see if I could exist in the world, in the present for once as the person I was coming to believe could be my true self. I learned the hard way that the public would not be as forgiving as much as my mirror was as I was treated quite rudely the first several times I went out. Even in places I should have had no problems in such as the big shopping malls back when they were popular. I couldn’t seem to dodge the giggles and stares I got from the teen girls before I learned to stay in the present, be who I was and begin to blend in with the group of other ciswomen in the mall. I learned the hard way to dress for them and not rely on some sort of trashy look that appealed to men. Which was getting me clocked as a man in drag every time.

All this new reality was teaching me I could indeed enjoy the present when I was out in the world. But not enough to keep me there when I was back in my unwanted male world. I have always wished I could get back just a portion of the time I wasted daydreaming of how it would be if I was the only ciswoman in a business meeting I was in. I know I could have been more effective…if I could have been accepted. Which I would not discover how difficult that would be until I got out further in the world as a transgender woman. I will always remember how I was shunned by a small group of men I somehow became involved in a discussion with when I first came out of my shell. Quickly I discovered, as a woman among cismen, I would have to fight for my right to be heard on an equal basis.

The more I was out in the world, the more I was forced to stay in the present. If I did not, I could find myself slipping back into old male habits which would give my past away much sooner. Such as not employing my old “stay away” male scowl and replacing it with a much more pleasant feminine look which said I was happy to be here. Which got me by. Other areas of just being a woman I needed to concentrate on was how I moved around in the world when I was still trying to juggle being in both worlds of male and female. One day I needed to be feminine, and the next masculine ended up taking a real toll on my mental health as I did not know somedays what present I was supposed to be in.

Plus, the one aspect of being in the now as a transgender woman was the one I always mention, communication. As I was blissfully (sometimes) going along my gender path, suddenly more and more ciswomen wanted to know about me and were curious why I would be in their world. I was totally blindsided when I needed to start and participate in entire conversations with other women who appeared in my world. I discovered communication went way past just how my voice sounded into exactly what I was saying and how fast I could pick up two uniquely feminine communication aspects. Non-verbal communication and passive aggressive behavior. The normal ciswomen who interacted with me ended up using all their skills to size me up and often it turned into quite the contest that I needed to stay on my toes to get through.

Eventually, surviving all the gender wars I went through, made me a better, more well-rounded trans woman who could hold her own in the world. Primarily because I had built up the confidence to do it, and it became my number one accessory. So, what if my makeup or walk wasn’t exactly correct, I knew who I was and it showed. There was no blood in my water for the human sharks around me to come after.

All those years of trying to get into my present and stay there finally paid off for me, but only after I had paid all my dues.

 

 

 

 

 

Violating Gender Boundaries

 

JJ Hart. Pushing my gender\
boundaries. 

Very early in life I learned that violating gender boundaries could result in severe trouble.

It was obvious to me that the male dominated family I was born into would ever accept a son who wanted to be a daughter. So, I had no choice but to turn inward with my developing feminine senses in the male world I was trying to be a part of. I was born way too early to take advantage of the forthcoming online information world with the advent of computers and social media. Again, I was trapped into trying to cross-dress my feelings away anytime I had the chance.

The other main problem I had was that the gender boundaries were so rigid and demanding I could not see any way out of my dark, lonely gender closet. I lived in a rural area with mostly boys and no girls to have a point of reference from. I only remember one occasion when the only girl in the neighborhood was persuaded by a couple of the boys to show her naked genitals to the group, and I was not excited but embarrassed for her at the time. Just another example of how my sexuality was developing away from the “normal” male’s. I had no need to see her private parts and wondered why I was so different. Little did I know, it was just the beginning of challenging my gender boundaries during my life.

As far as the rest of my life went, I wasn’t much of a challenger of anything. It wasn’t until I reached my college years and was drafted into the military during the Vietnam War, did I begin to challenge the system. At the same time, I was starting to challenge the war and the politics around it, I was pushing my cross-dressing boundaries by starting to leave my house more dressed as the person I wanted to see if I could become. I even made what turned out to be a huge mistake by coming out to my fiancé as a transvestite or cross-dresser back in those days. I say huge mistake because she wanted me to tell the draft board I was gay to stay out of the military service. Even then, I knew a lot about myself and did not have to push my gender boundaries so far to lie and tell someone I was gay. As a side note, then and now I did not have anything against the gay community, but I just knew there was a real difference between them and me.

Of course, the military stopped any gender challenging I was thinking of doing dead in its tracks for nearly three years of my young life. The only challenge I could do was mental in nature as I imagined how life could be better for me as a transfeminine person when I was discharged from the Army. Even then, I was restricted in my gender thinking to the reality in life. What I almost did was send a letter (remember them?) to my future first wife explaining it maybe a transwoman picking her up at the airport when she arrived for the first time. She was in the Army too and was discharged about nine months after I was.

Little did I know, if I had decided to test my gender boundaries then it may have been one of the better times to do it because I did not have the chance to build up all the troublesome male baggage I would acquire later in life. On the plus side, I had a very new car that I had shipped home from Germany, my stereo equipment and a sizeable bank account to start a new life with. On the negative side, I thought I had a good chance of losing my family, friends and job if I started all over as a woman.

Long story short, I did not have the courage to push my gender boundaries any further than they were at the time. Except for a few Halloween adventures, and the occasional night out, my life as a trans woman was mundane. It was not until I could not take it any longer the annual yearly adventures at Halloween, did I start to really push my luck by going out more often. My early explorations were rough to say the least until I settled down and learn how to blend in with the ciswomen who I found really ran the world I wanted to be a part of.

As the world let me in as a transgender woman and/or I finally learned the truth of who I was, I kicked and pushed until my gender boundaries came down. It was like the steep slope I write about as I slid down trying my best to hold on to what was left of my old male life but failing miserably. As I continued to gain my new feminine ground behind the gender curtain, which was hidden from me for so long, I had pushed by gender boundary so far, I was too far gone. I was no longer afraid of the fall and knew I was too far gone to ever go back to being my old male self.

From then on, gender boundaries did not mean much to me except from my former history as a man, I could see both sides of the border from where I lived as a trans woman. Leaving the man’s club scared almost all of the cismen away but attracted as many of the ciswomen that I needed to set up a new boundary. The new boundary was one which validated myself as a woman for the first time in my life and it seemed I was learning daily how to adjust to my new situation.

From that point forward, I changed my legal name and became extra serious about my physical and mental well being by being approved for HRT or gender affirming hormones. It just seemed by that time, I was just doing what came natural in solidifying my new gender boundaries. Sure, they were all big moves in my life, but good ones that I had always dreamed of making.

As always. Thanks to all of you who read along with my lifetime worth of experiences. Your responses and comments make it so worthwhile for me!

 

 

 

 

Living the Dream

 

Image from Randy Tarampi
on UnSplash.

I discovered before I could live a dream of living as my own unique sense of womanhood, I needed to discover exactly what that meant.

I knew very early on it was much more than just applying makeup and parading around in one of mom’s dresses. It went much deeper than that. I wanted to be a girl as badly as anything I had ever wanted in my life.

The problem was that I was stuck in an information “never-never” land with no internet or social media of any sort to provide key information on what it really meant to have issues with your gender and not just throw you aside with some sort of a mental illness diagnosis. I did know enough about myself to know I was not mentally ill for wanting to be everything feminine. So, I did the only thing I knew how, day dream my life away envying the ciswomen around me.

As I grew into myself, I learned more about my dream and the overall demands it would make upon my life. Even though I tried not too, I still added extra male baggage such as a child, marriage and a better career to my life. I always thought I would be better off lonely with just having myself to depend on if I ever had to get rid of it all in my male world and start all over again as a transgender woman. Another problem was that I was tantalizing close to encountering other gender conflicted people who were actively following their dreams, so I knew it was possible.

For example, I just missed crossing paths in my broadcasting career with other trans women who were actively following their dream. One at a small radio station I worked at in my hometown and another I ran into at a AFTN Thailand radio/tv reunion in New Orleans. Sadly, the trans woman was so shy and backwards, I could not even get her attention to say hello.

Everything changed when I came home to nearby Columbus, Ohio and was invited to very diverse small parties on a regular basis. Everyone was there, including several trans women who were headed for gender realignment surgeries that I was able to interact with and learn from. How much exactly did my dream entail? Going all the way like they did, or not was my major point of wanting to know about them. The one thing I did find out was that they had taken the time and effort to set themselves up for success in the new lives they were undertaking. One trans woman was a firefighter getting ready to retire and had a good pension and insurance coming to cover her surgery and another was a very successful electrical engineer who was extraordinarily beautiful and knew she would not have any problems continuing to work after the surgeries.

I was in neither of their classes in appearance, insurance coverage or job security to even compare myself to them, but still my dream of ever living as a transfeminine person would not go away.

Somehow, I needed to carve out my own individual gender path to success if I was ever going to make it. Finally, I learned the powerful message to just be myself and most of the rest of my problems in my male to female femininization would fade into the background. No, I was not extra attractive such as thedestiny transitioning transgender women that I knew but I realized that many of the ciswomen that I knew weren’t either. It was very shallow of me to think that all that went into to being a quality person as a woman was just appearance, so I grew past it. My focus shifted into having more confidence in myself as a good person that a stranger would like and away from just how I looked. When I did, my dream began to become a better focus. Maybe I could do it after all.

Of course, my major focus was what was I going to do with all the unwanted male baggage (and some of the wanted too) that I was planning on taking along on to my new life. At that point in time, my second wife was still alive, and she had made it a point to tell me she would never want to live with another woman, so I had to figure out what I was going to do about that major problem. Then I also had the usual conflicts we all face such as what we are going to do about employment and would any of our friends accept us.

For me, destiny came along and in one fall swoop showed me the way to living my dream. My wife passed away. Leaving me alone to consider my future about the time what was left of my close male friends died too. It turned out destiny was giving me a clean life slate to work from when I began to start all over. In addition, I was old enough to retire and work a little on the side to make ends meet and the Veterans Administration health care system which I was already a part of decided to approve gender related care or HRT for qualified veterans which I was. Destiny could not have shown me a better path to my dream than if I had planned it that way. I needed to pay my dues and work through many dark, lonely days to get to the light, but it was worth it when I did.

Finally, my dream became a focus for me when I met my future wife Liz and other ciswomen who let me into their world. I was able again to focus my dream on reality and make sure it was not a nightmare. Perhaps the best part of the entire trip up my gender path was the likelihood that I would ever make it. To say the least, my going forward was a shaky proposition to start with and all too often, my mental gender darkness threatened to catch up to me and my dream.

Thank goodness it never did, and my transgender dream became a reality.

Reality for me is also to have you join in with my thoughts. Thanks so much for doing so!

 

 

 

 

How Much Courage did it Take You?

 

Image from Jon Tyson
on UnSplash.

Often, I hear the words courage or bravery kicked around when it came to mentioning someone coming out of their closet into the real world.

In my case, I would have to replace either of the words with just being afraid of what would happen if I did not pursue my gender dreams of living as a transgender woman. Mainly because I was so self-destructive when it came to causing self-harm to my unwanted male self. I drove too fast and recklessly, drank way too much and even tried to actively kill myself once because of my gender dysphoria.

Especially after I had the rare chance to talk to my friends who survived brutal combat in the Vietnam War, I reserved the terms brave and courage for them. Because in many ways, I was just doing what came naturally when I cross-dressed in front of the mirror at home. It turned out staying in my own little feminine world was very easy until I began to want to see if I could stretch my luck and actually leave the house looking as close as I thought I could to a pretty girl. The only reality I did know was I was scared to death.

Little by little, my fear began to subside, and I wanted to expand my explorations to bigger and better venues such as the malls which were just beginning to come into their own back in those days. Still. I didn’t think I was brave enough to do it. Or was I just being stupid by risking losing everything that I worked so hard to build up in my male life. My ego dictated that I did not dwell on the stupid aspect of trying to femininize my testosterone poisoned body. I just wanted to blend in with the rest of the ciswomen I envied so much. As much as I was being abused by certain segments of the public, I began to use another term to describe myself and that was stubborn. In fact, I think that would be a great title to a new PBS show (Public Broadcasting System) called the “Stubborn Cross-dresser.”

As I continued on my gender path towards finally being allowed to join the girls’ club, my stubbornness in trying new things was both a blessing and a curse. A prime example was when I was trying to hang on to my teen fashion sense way too long. It was a curse, and my blessing came along when I became stubborn enough to keep going back to my cross-dressing drawing board until I fixed the problem and became able to blend in better with the women, I wanted to notice me. After the death of my second wife of twenty-five years, I was desperately lonely and did not want to attempt to build another life as a man when the possibility of building one as a trans woman was right in front of me. If I was brave enough to take advantage of a life I had only dreamed of. Was I going to take the easy way out and try to be a man again or build upon what I had learned as a novice transgender woman became my major question to answer.

Finally, I needed to “man-up” and be a woman as my second wife used to tell me and when I had the courage to do it, I felt a deep happiness in life I never had before. In fact the feminine privilege I found to be the most pleasant was the fact that I was allowed the opportunity to be happy. For the first time in my life, I was able to align my sun, moon, and stars so I did not have to fight a gender battle on two fronts which kept me unhappy and on edge. I positively loved my new life along with my first chance ever to just be happy with what I had.

If you are one of the many gender conflicted individuals trying to decide if and when you will make the ultimate choice to go for the gender border as a trans woman or trans man, my only advice must be, look deeply inside yourself for your answer. Your answer is there If you are stubborn enough to find it. Life is like an old merry-go-round and often it is difficult to slow it down to see the real world spinning in front of you. And if destiny puts you on the right path to do it, you can discover a group of well-meaning friends (ciswomen or men for you trans men) who can help you along. Making you a better person than you ever thought you could be. I would never have thought that the gender dysphoria that I felt would end up causing me so many problems in my life.

Before your life ends and you move on to whatever other place of existence you believe in, you have the basic right to be happy. You can deal in semantics and call your gender journey as being brave or having courage all you want but the end result is you being the natural person who you always should have been.

Somehow, we have been chosen to lead a different life’s journey than most of the others in the human race. Call us brave or courageous if you want but as a tribe, we are doing what we were always been destined to do. It is just too bad we are met with such resistance by haters in the world. As well as the gatekeepers who want to keep us away from our chosen genders. When I speak about gatekeepers, immediately radical feminist TERFs come to mind who have no business in ours.

Best wishes on your successful gender journey and summoning enough courage (if you want to call it that) to get out into the world and live your best life.

Thanks again to all of you who join me in my experiences, and I hope we can all learn from them. I apologize to all of you who have commented. I am a little behind getting back to you because of technical problems.