The Waiting Game

 

Image from Levi Mear Clancy
on UnSplash

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

 

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

 

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

 

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

 

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

 

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

 

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

 

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

 

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

 

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

 

 

 

Denial will Eat You Up

 

Image from Annie Spratt 
on UnSplash.

Over the years, turmoil from my gender dysphoria just tried to destroy me. Much of it came from the confusion I felt early in life as I tried to figure out if I was a boy or a girl and could I ever escape the gender box I was born into.

Perhaps the worst part of my inner gender feelings came from not knowing if what I was doing in front of the mirror was really doing me any good or was just a stop-gap measure to get me by to the next time I could cross-dress as a girl. Were my limited mirror experiences all that I would find to get me closer to my lifetime goal of being a transfeminine person. On my own terms. What no one told the young me was that the rules of my life would dramatically change. No one told me then that I would take three years of my life to serve in the military and then go through many years of therapy for a manic-depressive disorder. I was just a confused kid.

As I matured and went through the unwanted terrors of male puberty, I started to feel the pressure for the first time to fight back my gender dysphoria and do the so called “right thing” and just relax in the gender box which was given to me. Somehow, along the way, I had learned the powerful/destructive male response to some problems called internalization. I learned it from my dad as he never showed much emotion at all except when he was angry with us. Most certainly not the ideal environment for a gender dysphoric child to grow up in. There was no way I felt comfortable in going to my dad and telling him I wanted to be his daughter. So, the years went by with me internalizing all I felt the best I could. 

It was not until many years later when I was honorably discharged from the Army did, that I began to feel the increasing depression which was gaining on me. I knew something was not right and I sought out my first therapist for help. From him I learned one of basic truths of therapy, you only get out of it what you put into it. I got absolutely nowhere with my first therapist when I mentioned my cross-dressing and my growing depression which was beginning to seriously threaten my life I was building as a man. He finally prescribed some medications for me which made me feel worse and sent me on my way. I did not know what I thought would happen except nothing which did and my depression over my life began to build to the point I was not happy unless I was out in the world testing out how I felt as a novice cross-dresser.

Regardless of how negative my experience was with my first therapist; I set up other appointments to see another therapist who advertised gender therapy to try to save my rapidly dissolving marriage I was with my second wife. It was with her that I discovered another two truths about myself and the world of therapy. The first was that I was much more comfortable talking to another woman about my feminine desires than a man and for therapy to do me any good, I would have to listen to what I was told. For example, I completely ignored her when she told me there was nothing, she could do about me wanting to be a woman.

On the positive side, we talked about the major depressing lapses I was having in my life and how I spent days when I did not want to get out of bed. She diagnosed me with a form of Bi-Polar depression and prescribed me medication I take to this day which helps stabilize the chemicals in my brain which caused my extreme depression. On the negative side, I was left on my own facing my own battle about who I really was when I looked in the mirror. I was still years away from solving the major question of my life. Sadly, I was wasting valuable time in my life making the decision I always knew was true. I was always a woman pretending to be a man the best way I knew.

The best idea I had was to go out into the world and see if I could make it in a universe ran by and for ciswomen. A world which operated on a separate plane than cismen. I will always be thankful and amazed at the number of ciswomen who welcomed my arrival into their world and showed me the way behind the gender curtain. Where I always wanted to be in my life as part of the girls’ club. It was only then that doing my extreme gender turmoil begin to subside and I could relax and even be happy when I was out in the world as my feminine authentic self.

At that point, I needed to pause and reassess where a life of living a lie had taken me. All I did know was the HRT gender affirming hormones I was prescribed by my Veterans Administration therapist were miracle workers for me. I have spent time mentioning the external changes such as a softening of the skin, longer hair and bigger breasts which came along faster than I even hoped for on my femininization timetable. But I spend less time mentioning the internal changes such as emotions which came about quickly too when I found out how it was to cry. It was as if my body was syncing up with my external woman in the world by saying what took you so long.

As I said, the hormones forced me to play my feminine hand and with help of my circle of women friends, it was time to permanently leave my old male past behind. Sure, not all he had done was bad, but still there was enough negative to want me to leave him in my past and forget about all the gender turmoil behind me. 

I know I get comments all the time from those of you who have not had the chance to free yourself from the chains of your closet. I hope you have the chance soon to escape into the true world you always deserve.

Thanks for reading along, commenting is always appreciated!

 

 

 

 

 

 

 

 

 

 

 

 

 

Starting All Over Again as a Trans Woman

JJ Hart

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

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

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

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

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

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

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

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

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

I was more than ready to start all over again.

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

 

 

Sliding Down a Hill as a Trans Woman

 

Image from Alexander Mass
on UnSplash.

As I made my way into a very serious time in my life on my male to female femininization journey, I found myself on a hill with my male life slowly slip sliding away.

At first, as my male self-started to panic at losing his footing in the world, my overall life was in panic mode also. That was until I began to enjoy the process and realized it was nothing more than a normal progression into a transgender woman’s life, if I truly wanted to go there.

Keep in mind, I was doing my sliding in a pair of new high heels I was in love with, and for a long time I was on uneven footing. Then, I started to do everything in my power to determine if the grass was greener on the feminine side of the gender border for me or not. I even went to the extent of dating cismen to see if I had any sexual attraction to them at all. For the most part, finding a date with a quality man was difficult to do as most ciswomen know as most men were turned off by having anything to do with a trans woman at all.

To go out with me, a man had to be willing to meet me in a public place where I was already a regular in and go from there and I was stood up many times. Which I got used to. The only exception was a man I met in a group of people who had tried and failed to marry an exotic dancer who was beautiful and in the social group. After the brief marriage which lasted only a week, the man ended up getting made fun of by others in the group which I thought was completely unfair because I saw how much he was hurting. After that, on separate occasions when we happened to see each other at the bar, I tried to comfort him the best I could. It turned out the big bear of a man who ran a lumber yard and rode a Harley motorcycle was an interesting person that I liked and we got along. Sadly, he moved on before we could get to know each other better and I had a chance to ride on his Harley.

There were dates with other men which helped me slide down my transgender path, but not many as most men avoided me like a disease since they sensed I had left their club and were afraid of their frail sexuality being challenged. But other men were attracted to women like me I discovered as I was pushed along down my ever-steepening hill to my own feminine destiny. There were men such as Dan and Bob who were willing to meet my demands of going on a date at one of my regular straight venues I went to.

At first flipping the gender tables from male to female was difficult for me and I was extremely nervous but slowly learned what I would need to know to carry on a successful conversation from the other side of the binary gender spectrum. I learned quickly not to push too hard to start communicating and let the man lead the way and do my best to follow from there. I had to be careful not to be too reticent to talk because I was building myself into a strong feminine trans woman and did not want to give that up. I was a true contradiction in terms. I found I did love being treated like a woman but always was worried about what was coming next. I did not want to be the sort of woman who seemingly just led men on for sport. I did not have to worry because both men were gentlemen and we went upon our separate ways after a parting kiss. The kisses were the first I ever experienced with a man, and I was interested to see what if anything I felt after doing it. I did not and my sexuality was never challenged. I did not even go out and buy bananas to practice with as my ciswoman acquaintance Amy told me I needed to do.

This entire time of my walking my downhill gender path, I was noticing the biggest surprise of all. As men were ignoring me, women were attracted to me for any number of reasons. I think the main reason was women were curious why I wanted to give up being a man to be in their world. Whatever the reason, I found myself going to lesbian monthly mixers with friends and even being asked to be one of my friends “wing-person” one night when she was afraid to approach another woman for her phone number. I was overjoyed to do it and had another of those once in a lifetime experience when I was accepted for who I really was.

The only problem I was experiencing was a big one. I was still living parttime in a male world and slipping quickly down a hill into a female one. I had people to tell and a job to deal with among other problematic issues I had to take care of before I lost it all and plunged off a gender cliff into an unknown, I knew nothing about. My cliff was so steep, I could not see to the bottom.

By this time, proceeding carefully was out of the question. I had survived the death of my wife as well as most of the few male friends that I had and I was ready to make a change. Even then I could see which change was coming and I would have to take the chance to seize the opportunity of a lifetime to take it. So, I let go of everything that was holding me back and took the leap over my gender cliff, not knowing what was going to happen. On the other hand, I had done a lot of homework on what would happen if I did jump. All the way from testing my sexuality with men to socializing with the lesbian culture, I tried to cover all my transfeminine socialization bases as I slid down my path. Never being totally out of control.

The best part was the reception I received when I took my final gender leap. All the trust and time I had spent with women over the years was completely repaid and they provided me with a soft landing into a world I had only dreamed about as a transgender woman.

Hi! Thanks for reading along and no matter where you are on your life’s journey, I hope it is a successful one for you.

Anytime you have for comments is appreciated.

 

 

 

Destiny or Blind Luck

 

Image from Maia I on 
UnSplash.

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

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

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

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

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

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

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

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

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

 

 

 

 

Seeing It All Clearly Now

 

Image from Lola Rose
on UnSplash. 

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

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

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

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

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

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

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

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

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

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

Comments are always welcomed. 

 

 

 

 

 

 

 

 

 

 

On the Path to Being Me

 

JJ Hart. On the way to
being me.

On the road to being me sounds like one of the old “Bob Hope” and “Bing Crosby” classic movies if it was not so real.

It just so happens that the road I chose took me decades to travel and I finally arrived when I was in my mid-fifties and I tried to internalize my gender dysphoria by being an occasional but serious cross-dresser. Since I had very few natural feminine qualities, I had a lot of work to do.

Little did I know the lengthy journey in life that I was on would take me down so many side paths including three marriages. Including the one I am on now. All except one lasted over ten years, so I guess you can say I made up for in loyalty for what I lacked in other areas. Such as reoccurring gender problems I shared immediately with my wives before I married them. The major problem I had was I was never being honest with myself about who I really was which was a shame because deep down early on my path I knew I wanted so much more in life than just wearing the clothes and makeup of the women around me.

When I thought I was taking the easy way out about hiding my deepest desires, I was only masking my problems which made me a very bitter and nasty person to live with. Not a good recipe for a stable marriage, but somehow, I managed to maintain them anyhow. At the same time, I was trying to internalize my gender dysphoria, I would put extra pressure on myself to do more in my search for my own brand of womanhood. What I did not realize was all that I was doing when I began to explore the world outside of my closet was just socializing myself to the male to female femininization path I was going down. And every high heeled step was getting me closer to my goal. Even though, it was taking its own sweet slow time to do it. I found that every time I took a step forward, I would catch myself taking two steps back.

What would Bing and Bob do should have became my motto as I moved on in my mainly male world I was stuck in and could not get out. The only thing I did know was that I was stuck in a cruel gender comedy show I needed to get out of. I wanted so bad not to be perceived as a clown in drag coming from a local circus. The only thing I could do was stay on the dual path I was on to maintain the only life I knew. We were living paycheck to paycheck at the time so there was no way I could quit my job and try to start a new life over. I did the best I could to keep a balance between my two genders until the cavalry came to rescue me. The only problem was that the cavalry never came and I was on my own and was forced to learn to stand on my new high heels.

For years, I went into a self-imposed transgender exile as I needed to do a deep dive into who I really was and what I really wanted in my life. Sadly, I kept on betraying my true feminine side for my macho male side who was only good for paying the bills. The only relief I got came as I learned of the term transgender and immediately appreciated how it affected me. No pun intended, but it fit me to a “T” since I knew I was much more than a casual cross-dresser at the time. But at the same time, I did not have the desire for any extensive/expensive gender alignment or facial femininization surgeries, Somehow, I was going to have to find a way to pursue my trans womanhood on my own terms. All that was remaining was to figure out what those terms would be.

The only thing I knew for sure was I was becoming certain about who I wanted to be. I was tired of lying to myself and decided to start to carve out my own authentic transfeminine life. As I did it, I was beginning to get my glow back and love the skin I was in. The problem I had was loving the skin I was in, but I had not considered all the aspects of what I was seriously considering. For example, how was I going to tell the remaining close family and friends around me and how was I going to support myself when I started to live my dream life I always dreamed of doing. It turned out my procrastination came back to help me when nearly all my immediate blood family had passed away. Along with the only long-time male friends who I still had. Since I had always had such a difficult time making friends with me, I was not worried about making anymore anytime soon. It all left me too how I would support myself financially.

Once again, procrastination worked when I waited long enough to transition that I was old enough to collect my social security and sell collectables on the side so I could get by. I made enough money to keep going out in the world as a trans woman and keep carving out my new and exciting life. I went up, down and sideways to do everything right in my power to finish my dream of being able to live fulltime as a transgender woman on my own terms. My own terms were very simple; I just had the basics of living how I wanted. But again, I was frustrated when I went to do it. I wanted the path to finding my future to finally end and I could get on with my new life.

Most importantly, my new life was all I expected it would be and I could not wait to experience more of it.

Experience in life is all we have and I hope you get a chance to experience yours!

Thanks for reading along and any comments are always appreciated.

 

 

Putting Yourself Out There as a Trans Girl

 

Image from Sasun Bughdarian
on UnSplash.

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

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

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

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

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

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

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

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

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

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

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

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

 

 

Was It Ever Too Easy or Difficult

 

Image from Brian Lawson
on UnSplash.

Looking back at your gender transition, was it ever too easy or too difficult? From many of the comments I receive, I would say the answer is difficult. Even if you are an everyday cross-dresser all the way to a post opt transgender woman.  

For me, it went both ways like my gender as it depended on the experience or even the day. For example, when I was getting laughed out of venues I should have been passing in, my whole life was too difficult as the opposite of gender euphoria set in. My inner stubbornness set in, and I just had to do something to make my life better.

By this time, I was in survival mode. Clinging to every shred of gender euphoria I could find. By taking the time and effort to make my dysfunctional life better, I was making it worse. Just in time, when I was in total despair, I learned what I was doing wrong in the world to blend in and begin to prosper as a novice trans woman. Mainly I was dressing way too inappropriately for a woman my age, and when I started to look around at the ciswomen around me, life began to change. As I began to build a new professional women’s wardrobe, suddenly I found myself presenting and blending into feminine situations I never could before. It was not easy, but I was getting closer.

By closer, I meant my all-important confidence that I was doing the right thing was growing too. It helped when I was able to look another woman in the eye and have a face-to-face conversation too. It was very difficult for me to get there because of my inherent shyness and other factors but with a lot of work I did it. I was far from perfect, but I was learning.

Before I knew it, I became an accepted regular at the ciswomen’s get togethers after work at a local TGIF Fridays and I was in heaven every time I did it and wanted to branch out into other similar venues which accepted single women at their bars. Even though I was having no problems at those venues, it was never easy for me as I was always waiting for the other foot to fall when someone would ask me why a man in a dress and makeup was doing there. Needless to say, it never happened and I was able to enjoy my drinks in peace. I did not think of it then, but I was suffering from an age-old condition which was instilled in me as a kid that nothing was ever good enough. If I was succeeding in the venues I was going to, why shouldn’t I try new ones.

In other words, I was not stopping my trip up my male to female femininization journey to enjoy my progress. I was still looking over my back for trouble. Another problem I always mention it was how ill-prepared I was for the internal lives' women lead. I had never been allowed to see behind the feminine gender curtain and was left to my own to imagine how it was. Naturally, I played up the good such as the pretty clothes, hair and makeup and downplayed aspects such as passive aggressive behavior all the way to having to learn all the basics of womanhood from peer group approval. I had no sleepovers with other young girls to work with or mascara lessons from mom. As it turned out, I was probably wearing more makeup at a younger age as the daughter she never faced the fact she had.

Which always made another part of my life difficult because deep down I wanted for her to accept me for who I was. Even though I tried to explain to her one night that I always wanted to be a woman, the best she could do was reject me and offer therapy. We never mentioned it again as I struggled for acceptance in my new feminine existence. I could never understand how she could reject me so quickly with no discussion whatsoever. She was part of the “greatest generation” which I guess did not include emotional support for gender issues. Since I was used to my parents not making my life easier emotionally, it was easier for me to move on.

As I did move on in my own new and exciting transfeminine world, I was able to discover social sources of emotional backup they never knew they provided. What they provided was a learning experience for me to do away with any vestiges of my male past. After the years of fighting the gender changes, he was facing, my male self finally gave up his throne fairly easily and let my long hidden feminine self-take over and erase the scars from all the fighting she went through. Most importantly, my new circle of ciswomen friends never questioned my femininity and I flourished with them. Making up for all the lost time I had as a man trying in vain to hang on to what he had in male privilege he had earned but had never had the chance to appreciate because he never really wanted them after all.

It all brings me to the now of life. I still bear the recent scars of the two new Veterans Administration nurses who kept referring to me as “he” behind my back because my doctor never does. The difference is now the gender slings don’t hurt for long because I have long since concluded, I am only me and that must be good enough. Plus, I just learned that the VA is facing a shortage of the Estradiol patches I use and I only have a couple weeks of patches on hand to use. So, once again, hormonal injections may become a reality for me. It’s another bridge I am building that hopefully I will not have to jump off.

Perhaps I will always carry with me some of the difficulties which come with a transgender life that I never started with any natural feminine qualities. Testosterone poisoning tore me up and I have paid the price ever since. But, like before, I will get over the bad and embrace the good from the family and friends who are around me.

Thanks for reading along and I hope you gained serious insight from my writings. Any comments or claps are always appreciated by you!