A More Innocent Time

 

Image from Arun Sharma
on UnSplash. 

On occasion, I look back at the early days of my cross-dressing past wistfully thinking those days were the innocent ones of my life before everything began to get more complicated.

In those days, all I needed to do was make sure I did not destroy mom’s pantyhose or stockings and be careful to put back her clothes where I found them. I guess I was successful because she never said anything to me. Using her makeup was much easier because she always kept samples in a side drawer in the bathroom, I could experiment with. At that time, the whole cross-dressing experience seemed to be an innocent game. Except for my deep paranoia about getting caught. Even the paranoia led me to being more creative about hiding my feminine clothes and makeup. What I had of it.

When the reality of serving in the military during the increasingly deadly Vietnam War slowly but surely made its way into my life, much of my innocence began to go away. The stark reality of going without my dresses and makeup for three years of my young life began to set in. After I passed my draft, medical exams and tests there was nothing I could do about it. Because I was not prepared to run to Canada to evade serving in the military. During that time as well as many years after I was honorably discharged from the Army, I continued to be quite naïve or innocent that all I needed to do to survive as a transgender woman in the world was to do my best to look really feminine. These were the days when my second wife and I battled back and forth about how I was cross dressing as a woman. She always thought my makeup was overdone and I was too fond of wearing “girly” fashion for her tastes. I tried to tone it down for the occasions we went out as two women but her expectations of me were so strict that if I followed her directions, I might as well not bother cross-dressing at all.

Even though I lost most of the battles with her about my evolving fashion sense, I won a few wars when she had to ask me for makeup guidance when we were going out to a fancier setting. Revenge was sweet. For a while, life was very routine for us as we both had challenging employment when we moved from our native Ohio to the suburbs of New York City, a real culture shock to us both. I was disappointed when the more liberal attitude I expected in the big city never materialized because we had to rent from an elderly Italian man and his wife who I knew would have never accepted a trans woman in their apartment. Long story short, my wife loved NYC while I disliked it and started my habit of rapidly changing jobs and moving to outrun my gender issues. Undoubtedly, I had entered one of the most exhaustive phases of my life as I tried to balance my growing transfeminine desires with a wife, a job and a family.

By this time, my growing one on one interactions with the public were driving what I had left of my innocence away. I began to realize that I was locked in a life-or-death gender struggle which may be impossible to ignore. What did I do? I exchanged my exhausting job changing for settling down in one great job opportunity, and at the same time begin to explore the new and exciting world of being a trans woman fulltime. For a time, I was fulfilled by both aspects of my new life until I began to be overwhelmed by the speed both my job and me being able to carve out a life as a new trans woman was coming together. I never imagined I would be so successful, and so terrified about what I would do about them together.

I like to refer to the process I was going through as trying to piece together a large, complex puzzle of life. On one hand, I had my male side loving the financial increases he was seeing. Then my female side pushing back to what was more important. Making money as an unhappy man or living a softer more fulfilling life as a transgender woman. Almost daily I struggled with finding the right pieces for my puzzle. All I accomplished was taking all the satisfaction I was feeling from either side as they battled on.

As I faced the new world I was living in, I was determined to be less self-destructive but that did not work either as I continued to do things like go to my restaurant competitors dressed as my authentic trans woman self. I was not that good, and it did not take long for the gossip to get out about what I was doing. Sabotaging all that I had worked so hard to achieve in my career to finally let people know who I really was. I was destroying once and for all my male past and the innocence was gone. However, with the loss of innocence came the deep feelings that I had finally made the right choice and everything I had done in life directly or indirectly had influenced my future. My primary example is fathering my daughter, who over the years has accepted me and I love very much. Without being forced into the Army where I met her mother, I would never have had the experience of my life. I am just fortunate that I was destined to live as long as I have to have the chance to see the pieces of my puzzle come together and have a chance to experience one of the most interesting and scary experiences a human can take. That of course is crossing the gender border from male to female to live on the other side.

I was never good with puzzles, especially my own, and to lose my innocence finishing mine was a real treat.

 

 

More Changes

 

Image from Brad Starkey 
on UnSplash.

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

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

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

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

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

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

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

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

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

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

 

 

 

 

 

I Always Was a Dreamer

 

JJ Hart

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

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

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

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

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

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

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

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

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

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

 

Are you Worthy, or an Impostor

 

Image from Strechath Gupta 
on UnSplash

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

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

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

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

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

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

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

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

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

 

 

 

 

 

The First Time

 

Image from Jon Tyson 
on UnSplash.

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

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

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

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

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

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

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

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

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

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

 

 

 

Playing on the Girl's Team

 

Image from Fa Barbosa
on UnSplash.

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

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

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

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

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

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

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

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

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

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

 

We Must Be Better

 

Image from Ecaterina 
on UnSplash

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

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

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

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

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

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

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

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

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

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

 

 

Out in the World

 

Hair by JJ Hart. Bead work 
by Liz T Designs. 

Just a short post today due to time constraints.

I am going with my wife Liz to two of her doctor’s appointments this morning which will take up the usual time I take every day to write. Fortunately, the visits take place very close to our house, and we don’t have a long way to go to get there.

To get ready for the appointment, I need to take time for a close shave, moisturizer and pick out some casual clothes to wear. It is going to be a warm day here in Cincinnati, so I am planning on wearing a pair of leggings, along with flats and a short-sleeved top. Plus, I can’t forget to brush out and tie back my long hair.

No need to put a lot of effort into going casual to the doctor’s office where no one notices me anyhow.

Then later on in the day, Liz and I are meeting with a construction contractor assistant about redoing our upstairs bathroom. The assistant is a younger woman and one of the very few people I have outed myself to as being a transgender woman in the past several years. So once again, a nice casual outfit will be all I need to wear for her visit.

I doubt if anything exciting will happen today but if it does, I will write about it!

I've Got Someone for That

 

JJ Hart on Left, wife Liz on Right. 

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

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

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

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

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

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

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

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

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

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