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.

 

 

 

 

 

We Must Be Better

 

Image from Ecaterina 
on UnSplash

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

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

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

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

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

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

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

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

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

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

 

 

I've Got Someone for That

 

JJ Hart on Left, wife Liz on Right. 

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

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

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

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

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

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

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

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

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

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

 

I Got Scammed

 

Image from Markus Winkler
on UnSplash.

Years ago, I discovered I was scammed when I attempted to climb my gender path towards my dream goal of living completely as a transgender woman.

My first mistake was believing what I saw in the mirror when I was cross-dressed as a girl was a true indication of what I really looked like. The mirror was more than capable of lying to me by telling me I looked attractive, when I really looked like a circus clown in drag. It wasn’t until I began to go out in public as a feminine person, did I find out the brutal truth of how far I still had to go to present well as a novice cross dresser in public. Rather than create attention to the way I looked, I needed to blend in with the average ciswomen around me and just get by.  I was scamming myself to think otherwise.

Sadly. The scamming continued unabated until I woke up to the true world around me. My life was restricted by outdated thoughts I carried through from my still very active male self who thought dressing sexily was the way to go. The only good thing that happened during this part of my life was that I went through my cross-dresser “adolescence” fairly quickly and began to attempt to dress my testosterone poisoned body the best I could to hide my flaws. I was aided by fashion styles back then which favored miniskirts, bare legs, opaque stockings with oversized sweaters. I was even able to continue a version of the fashion basics when I changed into a bohemian style denim mini along with a flowing loose top to hide my oversize male torso. For once, fashion trends were playing in the right direction for me and my scamming decreased from my male self and the public.

At that point, I shifted my emphasis on where I was going when I was learning the world for the first time.  Initially I chose more malls and safe places such as coffee shops and bookstores until I got bored and chose other venues to go to at night when I began to sneak out of the house when my wife was working. At first, I was satisfied with going to a few male gay venues in downtown Dayton, Ohio. Even though I did not like the overall atmosphere of the places, I kept going because I thought they were safe. That was until I was stopped on a sidewalk outside one night by two men looking for a handout and I was lucky I still had a five-dollar bill to give them, so they left me unharmed. I learned a valuable lesson that all ciswomen knew which was to always be careful of your surroundings and I never went back there again unless I had friends with me.

I also felt I was scamming myself and wasting my hard-earned money by going to gay venues at all. Lesbian bars for the most part were fun for me for a number of reasons. Including the attention, I would receive on occasion from a few of the other patrons. Male gay bars however just treated me like any other drag queen which I hated. I even had a hard time being served which drove me away. It was then; I decided to stop being scammed and take my business to straight sports bars where I knew I could enjoy the atmosphere if only I could be accepted.

I was surprised how quickly I was accepted at venues I used to frequent as a man, and I felt comfortable in. The difference in venues was in the straight sports bars, other women wanted to actually talk to me. Which opened up a whole new world of possibly being scammed by ciswomen and their passive aggressive behaviors. I don’t want to recall how many times I went home with claw marks on my back after I assumed another woman’s smile actually meant she was being friendly with me. That scam became old quickly and I learned to be careful in the world in a whole different way.

The biggest scam of all came when I learned I was not a man cross-dressing as a woman, I was a woman cross-dressing as a man to get by in a life she never wanted. If I had only learned that earlier in life how much easier I could have made it on myself. No such luck, as I was destined to be scammed by a world and my male self into thinking I was doing the right thing by fighting hard to keep my manhood. These days, I am older and wiser when it comes to scamming myself and have accepted the transgender truth, I always denied myself.

As I wrote in a recent post, I would not recommend the path I took towards achieving my dream because the world has changed since I did it. Harsh anti-transgender politicians have made it harder to come out in the world as well as making it harder for some of us to exist at all. (Like in my native Ohio). Hopefully though, the younger generations seem to be resistant and blind to the bigotry of their elders and there is hope for the future. That was, none of us will have to worry as much about scamming ourselves or each other about who we truly are. Just people who have been around forever and are trying to live a basic, honest life.

One way or another, the path we have chosen as transgender women and transgender men is much more difficult than the average person next door. And I can add scammers along with stop signs, blind curves and steep hills on our route to finally discover who we are with the opportunity to live it. It just makes it worse when we learn the person who was our main scammer was ourselves.

As always, thanks for joining me in my journey. Any comments, claps or subscriptions are always welcome!

 

I Had to do Something Right

 

Image from Mark Farias on Unsplash 

In my dark days of confusing cross-dressing, I vaguely knew I was doing something right. Or at least I thought so because I could not wait to try it again.

Looking back, it was the brief moments of gender euphoria which clouded all my doubts about my gender and kept me going. Even through the nights when I was the laughingstock of teen girls in malls, a little voice kept telling me to keep going and eventually I would improve my overall feminine presentation so that I would blend in and not get noticed. Along the way, I even needed to lower the expectations I was putting on myself to keep going. I was never going to be the most attractive woman in the room, but at least I could still be like most ciswomen I saw and live a decent life. Even though I started to feel this way, I never gave up the idea I could do better with my makeup, fashion and hair so I could survive. Simply because I was enjoying the experience so much.

Later on in my life, doing something right extended to my interaction with the world as a novice transgender woman. I was surprised when I attracted more attention from ciswomen than men and just thought they were curious about me and were welcoming me into their worlds, while men were just the opposite. Most resented the fact I was leaving all of the male privilege behind (along with the good old boys’ club) and moving to the other side of the gender border. I did not care because my need for companionship was being satisfied and I had always gotten along with women easier than men most of my life. Increasingly I found I never wanted to go back to the male life I was attached to by a spouse, family, friends and jobs. It seemed the longer I waited, the more male baggage I was building up when I really did not want to.

The next problem I ran into was the impostor syndrome I was feeling. Specifically on the girls’ nights outs I was invited to. It never failed that right in the middle of me enjoying the evening, I had suspicions sneaking up on me that I did not belong there at all. I was an impostor in a scene made up of women who had worked their entire life to get there. It took me awhile to come to the conclusion that I had worked my entire life also to make it to my own version of womanhood, and I deserved as much as the next woman to be attending. Fortunately, I received very little negative feedback from other women attending the get-together, so I did not have to face my impostor syndrome at all. I was doing something right for a change to even be invited to such special women only events.

I was able to take my experiences with girls’ nights out to my everyday life primarily because it built my confidence as a transfeminine person so much. With my newfound feelings, I worked even harder on my makeup, fashion and hair to appear more feminine than ever before. Primarily, I learned the power of contouring and colors on my face from professional makeup artists I met at the cross dresser-transgender social mixers I went to. One in particular, took the time to explain what he was doing in terms I could understand and repeat on my own. It was a powerful experience when I had to set my makeup ego aside and learn better results from a professional. From that point on I worked on taking weight off, so I had a better opportunity to find and buy more fashions that flattered my male figure at the many thrifts stores I frequented. When I arrived at that point, the problem then became getting out of the mirror and started putting my new improved feminine self into motion in the world. It proved to be the most difficult part of me doing something right.

Suddenly I had to consider how I was moving as I tried to mimic the unique way ciswomen move and put all my male linebacker moves behind me along with the scowl on my face I was used to wearing as my male defense mechanism. And the most difficult issue of all was learning to communicate one on one as a woman. I knew with certainty I would have issues with my communication, but not to the point that I did. I even went to the extent of taking vocal classes to improve my feminine basics and be able to talk easier in the world with women and men. It just made sense to do if I was continuing to do something right.

It turned out, the more I did right and received positive feedback, the more I wanted to do to refine my feminine approach as a transgender woman. Because I always had the belief, I needed to be better than the average ciswoman to just survive behind the gender curtain. When I was just trying to do something right, on occasion I paused to reflect on how far I had come along my gender path to arrive where I was. I did remember that scared little boy dressed in his mom’s clothes in front of the family’s hallway mirror, wondering what was next. For the most part, back in those days, there was very little to let the young boy know he was doing anything right.

Somehow, I survived all the negative feedback and impostor syndrome problems and continued forward to a better world. One I wanted to be in and dreamed of my entire life. As I love to say, as with any woman, I needed to socialize myself into the world. Being born female does not automatically make you a woman, you must learn to be one. The same was true for me. I just took a radically different path to earn my womanhood. I needed to do many things right to arrive at my dream.

 

 

 

 

Facing my Deepest Fears

 

Image from Tonik on Unsplash. 

Over the decades I have found that my gender desires have produced the biggest fears and anxiety I have ever felt.

Prime examples came from the times I was first testing the world as a transgender woman. The number of occasions I needed to sit in my car making endless tries at adjusting my hair and makeup until I felt everything was right to attempt going into whatever venue I was going to. You would think from the number of times I had to face my fears; I would have at least become used to it. But I never did. In fact, I developed my own form of trans PTSD from the number of times I was rudely rejected by the public. I could not get it out of my mind that if I was laughed at once, I could be laughed at again. Which I discovered just was not true after I learned to dress for the public of ciswomen around me.

Finally, a little confidence began to creep in, and I did better for the most part, but it seemed the fear of being myself just would not go away. Maybe I can blame my old male self who in his own way was as strong willed as my feminine self and did not want to give up all the male privilege he worked so hard to earn. His reluctance to give up pointed to a deeper problem I had. The fear of facing myself. At the same time, my dreams of even trying to become a fulltime transgender woman in the world seemed to be a far-off dream.

What I decided to do then, even though I still was experiencing deep fears about my future, was experiment by going out into the world a little at a time. I started in what I perceived as safer spaces such as shopping malls and gay venues. If and when I was successful (or grew tired of) in those places, I would try more challenging places. Lessons I learned included money overcame gender problems in the malls and I was just considered another drag queen in the gay bars and made to feel completely out of place. I discovered to enjoy myself more I would need to try to frequent the same sports bar venues I went to as a man. Where I could drink draft beer and watch my favorite team on the big screen televisions. Sure, I was scared to do it as I knew how single women were viewed in sports bars, but I had to try.

Desire overcame fear and I was successful as long as I followed my three basics of smiling, never causing problems, and tipping well. Before I knew it, I was a regular and gained the backing of the bartenders who even saw to it that I had restroom privileges. Before  I knew it, I had built a small circle of lesbian friends who shared my love of sports, as well as another transwoman. Loneliness became a thing of the past for me, and my fear of being seen as a woman was going away too.

Just when my trans confidence was at an all time high, obstacles such as drunk guys would come along and ruin my evening. The night I remember the most was when a bunch of drunks noticed my trans friend and I at the bar and started playing “Dude Looks Like a Lady” time and time again until the manager asked us to leave. We did, temporarily, because a month later when I was in a nearby competing venue, I was surprised to see one of the bartenders who was there when I was asked to leave approaching me. I was astounded to learn the manager who had kicked me out had been fired for drug use and I was invited to come back. So much for the drunks who had played that song over and over and I had put my fears to rest. To this day though, when I hear that song, I cringe.

Sadly, even though I have been in the public’s eye as a transgender woman, I still look over my shoulder when I do things like use the restroom. Fortunately, I have Liz to help me out when I have to go and mainly these days, I don’t present as trans as much as I do as old and partially immobile. I am happy these days when I can find a restroom with a handicapped stall to take my fears away.

My deepest fears now revolve around the number of ridiculous restrictive anti-transgender bills currently in the Ohio legislature. One bill would make it illegal for anyone to wear makeup different than their birth gender. Which I guess would mean the orange felon or his sidekick Vance would be arrested if they come to Ohio. I am lucky that age and years of HRT have softened my facial lines to a point of where I don’t wear much makeup at all but what about the younger transgender population. Hopefully, none of this will actually happen or the courts will strike it down.

These days, I have managed at least to calm down my fears of what will happen to me if I have to go into assisted living or if I develop dementia like my dad had. I finally came to the conclusion not to worry about something I have no control over.

I don’t know why I waited so long to be paranoid over what has made my life worth living over the years and decades. I used to be a go with the flow type of person and if I got myself into some sort of a mess, I could get myself out of it. Probably now it is because I have to depend on my wife Liz for so much. Fortunately, most of my deepest fears came from pursuing my gender truth and when I came out to myself, I proved that I was the most important person of all to be truthful with. It was not until then did my life began to change for the better and I could live without all the fear I was experiencing.

 

 

 

 

Easter Envy

 

Image from Annie Spratt
on UnSplash. 

Once again, it is Easter and time for some ciswomen to model their new colorful, feminine dresses and accessories to the world.

Like most of you, I remember the envy I felt when once again I needed to be forced into a restrictive suit and tie for one of the rare occasions we went to church. Why couldn’t I be one of the girls in their Easter finery. All the envy in the world I felt did me no good as off to church we went. My parents thought I just did not want to go to church (which I didn’t) but did not realize the real reason. I was just jealous of the girls.

Back in those days, I had very little inkling of how my desire to look like the other girls ran much deeper than I ever thought it would. I was scratching the surface of where I would end up in life as a fulltime transgender woman. I thought it was an innocent hobby that perhaps some day I would grow out of when the opposite happened. I grew into it. If I had any idea of all the growing pains I would feel over the years as I grew into my true self, I don’t know if I would ever undertake the gender path I did.

The truth of the matter is that I did not think I had any choice. I was born into an unforgiving male world that I was expected to excel at. I knew too that if my cross-dressing or gender secret was uncovered, I would be sent to a psychiatrist and told I was mentally ill. I did not know exactly what was going on with me, but I knew I was not mentally ill for just wanting to be feminine. On the other hand, I knew my WWII/Depression era parents would have any idea of what was going on with their eldest son to take any creative measures to help. The first measure would be acceptance. In my wildest dreams, did I ever think they would buy me a pretty new dress for Easter and do away with my suit and tie forever. My parents were simply not built that way so that they could step out of their rigid parenting box to help me. I was stuck in a male world until I could figure a way out on my own.

Over the years, regardless of setbacks such as military service, I was fairly successful in my male life. Which ironically made it harder for me to give it all up and cross the gender border when the time came. One thing I never lost was the envy I felt for all ciswomen who inherited from birth what I wanted so bad. I kept remembering the girls and women in their Easter dresses, even though I rarely wore a dress as I attempted to blend into the world as a woman. It seemed fashion had gone away from the frilly feminine basics once I arrived at the point where I could take advantage of the new world I was in. For years what I did take advantage of was the fashion trend where I could wear oversized sweaters with miniskirts, flats and opaque tights. Sadly, fashion moved on, and I needed to also if I was still going to blend in with the world as a transgender woman. Not only did I have to try to equal the cis women I was around, I needed to be better. So, I went with denim mini’s with long flowing tops to attempt to hide my oversized male torso.

Even with all the effort I was putting in, it never seemed to be enough to compensate myself for not being the pretty girl in her new dress at Easter. Ironically, then I found out from my wife Liz how she was a tomboy and did not like all the frilly Easter fashion she had to wear and was always under inspection from her mom on getting her new white tights dirty. I learned the view of the other gender side was not always the better one. It left the door open for a greater understanding of what females go through to be socialized into women and why some never make it.

This Easter, if you are religious, I hope you have the opportunity to celebrate the true message of the day and you don’t get hung up on what the ciswomen and girls around you are wearing. Although, I don’t see many women getting all dressed up for any reason anymore. Maybe if I attended any sort of church services at all, I would.

At any rate, celebrate Easter in your world the best you can!

 

 

 

 

 

Transgender Day of Visibility

 

JJ Hart doing trans outreach work. 

Transgender Day of Visibility was yesterday, and I did not post because I was out most of the day being visible.  Which was a change for me.

In the morning, I had several low impact visits to venues I feel secure in, so I did not feel any undo stress in going.  My first visit was to my local Veteran’s Administration Clinic to have my annual hearing check.  Even if my wife Liz perhaps may disagree, my hearing stayed the same and my next appointment was set for two years from now. From the VA, my next stop was at our bank where I needed to pick up a certified check. I was surprised when the bank was relatively busy and I needed to wait. Which is a problem with my mobility issues. Two very nice women helped me out by directing me to a chair saying they would guard my place in line if anyone else came in and tried to cut ahead of me. From there, it was clear sailing because the teller I went to was young and did her job very well and I was out the door before I knew it and there was no reason for anyone to question my gender. I was just a woman running errands as me. The best possible response I could have to my day of Transgender Visibility.

I knew my next stop would be easy because I was going to our favorite coffee shop to pick up a late breakfast and coffee of course. Over the space of time I have been going there, I have never had any problems with any of the staff concerning who I really was. The staff is always immersed in what they are doing to be concerned about me and even had a LGBTQ flag on their wall for a while when they had a decidedly non-binary manager in charge which was good to see.

My third and final interaction for the day came with a young woman who was a bath consultant at a company we were considering putting in a new walk-in shower to replace a dangerous (for me) old bathtub we had enough of. While we were in the small talk get acquainted part of the process, she asked what I did with my time since I was retired. I said, mainly I write a blog, and I am writing a book for my family to read after I am gone on my life. She was interested in what I blogged about. Then I broke my own rule, outed myself and said I write mainly about what goes on in a transgender person’s life. Of course, I needed to say I was transgender and today happened to be the Trans Day of Visibility, so here I was. Since the consultant was young and wanted to sell us something she did not react negatively to the idea I was transgender and married to Liz.

I came away from my own limited day of visibility hopefully thinking I had done my own small part to further the cause of transgender women everywhere to contradict all the negative publicity we get from the politicians. It is important to show the world we are just people like they are attempting to live our lives with no problems. Sadly, with my mobility problems, I cannot be as active as I once was in the community and go to public events like I used to.

Plus, more and more at the age of seventy-six, I am actively becoming me finally in life. It was like going through another major transition. I went from me being a cross dresser to accepting myself as a transgender woman, and now I am completing the circle and going back to me again. Only this time, with a big difference. I am the feminine being I was always meant to be. I was just fortunate to live long enough to live my circle. And celebrate another Transgender Day of Visibility.  And, if you are in the process of thinking of escaping your closet and having your own day. Celebrate those who are leading the way for you! Plus, on a positive note, the younger generations seem to be blinder to gender bias than the older ones, so all is not lost for the future you. Then, you can be involved with your own day of visibility and feel good about yourself.

 

 

Was I being Selfish?

 

Image from UnSplash and
Brooke Balentine.

When I was a maturing cross-dresser, one of my wives made it a prime point of her argument against my cross-dressing at the time saying that I was just being selfish. The problem I had with her saying that was deep down, I knew it was true. Mainly because I was spending all my spare time thinking about or doing my cross-dressing activities. I felt guilty, but there was little I could do about it as I wanted to be feminine so bad. So, I went on with my daily activities ignoring the best I could what she said.

Sadly, my selfish problem only became worse the farther along I traveled up my gender path. I simply wanted more from my life than what I was getting and I was pursuing it. I thought to hell with the risk I was doing to my male world and life as I knew it if my secret was discovered as it almost was several times. Like when I almost ran head on into my wife’s boss going to a big box store in a small Ohio town we lived in at the time. I did not think he recognized me, but he did bring up seeing a a particularly “big” woman the other day when he left work to pick up supplies at a party we were attending at his house one weekend. Of course, I could not let on it was me he was talking about, but my wife knew and questioned me about it later. I don’t think she ever believed my denials, but life went on until I made it to the next level of being selfish.

When I was out in the world as a successful transfeminine person, just doing it a little bit was just not enough. Success bred success, and if I could not for some reason make it out into the world again, I grew angry and bitter with life and tried to take it out on the world around me. By doing so, I even almost lost jobs because of my attitude. Having a sullen selfish attitude got to be so bad, I even sought out gender therapy to help me from one of the few therapists in Ohio at the time who dealt with it. It turned out to be that she could not work miracles with my gender issues, but she did with my attitude which was influenced by being diagnosed with a Bi-Polar depression disorder. Following a few experiments with medication, I found one that worked and my life became better. Except for I did not magically quit my feminine ideas and remained on my selfish path to see if I could ever live my dream of going full-time in life.

What made matters even more frustrating was, even with all the mental energy which was going into my transgender issues my male self was still able to advance in his life too. Making it harder for me to think about moving along with my plans and even being selfish about them at all. Through it all, my guilt was building about why I was even cursed with being transgender at all. This was before I finally began to understand my gender problems were not a curse at all.

In the meantime, my wife and I were clashing every time she caught me being selfish and leaving the house as my feminine trans woman self. One time she was even mad enough to tell me why I wasn’t man enough to be a woman. If I was smart at the time, I would have listened to her advice. I should have faced my true self and started making plans for my ultimate male to female femininization project. I just was not ready for several reasons such I loved my wife very much and the life we had built together.

By now, you have probably noticed a theme here. I kept shooting myself in the foot by being supremely selfish when I set out to build a new life when I already had a perfectly good one with a loyal wife, good job and loving family. All of which helped to describe why I felt so much stress and tension during this portion of my life. All the therapy and medications in the world could not help me until I had the courage to face up to my true self as she looked at me in the mirror. She had been there all along, and I thought I needed to apply makeup to bring her out (which I did for the public) but one on one, she was very real to me. She appreciated all the outwardly things any ciswoman needs to survive but inwardly, she just needed to be recognized for the person she had the potential to become.

Ultimately, I outlived my second wife (and many family members and friends) which freed me up to not feel any selfishness at all about what I was doing with my femininization. I was just busy preparing my world for the truth I had so deeply known. I should have never been a male at all and was just a woman cross dressing as a man. Needless to say, it was an enlightening experience coming out of my gender shell and having the opportunity to live my feminine truth. Just having the chance to compete in a world of ciswomen on their level was an intimidating yet exciting experience which my true self was up to. After living life hidden away all so many years against her will. As with most all transgender women and transgender men, it is a major project to bring ourselves into the world and unfortunately, we must be selfish to do it. The good thing is, once we go through the selfish part of our lives, we have the potential to be good, loving partners. If we are destined to find that special someone to love.

Life dictates it is nothing but a circle, and we have to take the good with the bad. Selfish or not.

 

 

 

 

 

The Winds of Gender Change

 

Image from Taylor Flowe
on UnSplash. 

Per normal, we have had a very windy spring here in southwestern Ohio USA. For some reason, I have never associated spring with my gender changes like I have during the fall season. I remember vividly the fall evenings I spent driving around feeling melancholy about the fact that I was stuck in my old unwanted male life. Seemingly, forever. Maybe it was because of the trees losing their leaves which set the fall off from the spring. I just knew it was happening.

Fall was especially bad when I was on a six-month delay to go to the Army basic training at FT. Knox, Kentucky. It marked the time for me that I knew I would have three years away from my gender cross-dressing activities which kept me sane at the time. I was afraid of going to basic infantry training as well as losing my ties to my feminine self for the next three years. The only reality to me was that I had no choice but let the winds of change take me away to a new uncertain future.

When I was in the service, my theme song began to be “Call Me the Breeze” by Lynard Skynyrd because of all the moving I was doing from the US to Thailand, to Germany, I was truly able to feel the wind thanks to the efforts of Uncle Sam and his military. I did it so well that I was even offered a promotion if I stayed in an extra year, which I turned down. Instead, I got out and resumed my civilian life at a small radio station I worked at before the winds of gender change got the best of me, and I started to follow my instincts and began to explore the world as a transgender woman. Which was becoming increasingly evident to me was where I fit in in the gender spectrum.

In the beginning, all I had was Halloween parties to express my femininity and even there, I was not doing a good job of doing it. I was stuck trying to do a trashy look when in fact, my inner woman was pushing for a more realistic approach such as being a professional ciswoman. What did happen was, I got the basics of what it would take if I ever threw caution to the wind and went across the gender border from male to female. It was at those parties that I found that all of a sudden, the other women wanted to talk to me while the men left me alone which would be a theme for my life as I transitioned.

Once I left all the Halloween parties behind me, I started to attend small diverse LGBTQ mixers in nearby Columbus, Ohio. When I did, it was as if there was one of those huge Hollywood movie fans at my back pushing me forward. From lesbians to transsexuals, all were there so I could judge where I would be if I moved forward in the world. Due to the fact that I was still solidly married and had a very good job, I needed to shut the fan off, or at least put it on a slow speed so I could catch my breath and figure it all out because of the gender complexity it all presented. Did I want to give up my life of male privilege to be a trans woman, at that point in time I was undecided.

It turned out, indecision was my worst enemy as I entered the world to explore it as a transfeminine person. Most of my ventures were ill-advised attempts to be accepted in gay venues in Dayton, Ohio where I was barely welcomed and when I was, it was because they thought I was another drag queen. Which was far from the truth. It was not until the winds of change blew me through the doors of the same sports venues I enjoyed as a man did my world began to turn around for the best. To my amazement, I earned my acceptance in those places easier than the gay bars I was going to, or the lesbian bars which were closing due to lack of business. Before I knew it, I was treated like a regular. Even with the restroom privileges I needed so badly.

I was flying high until the winds of change dictated a change and I crashed to earth when everyone dear to me began to pass away in a two year period. Including my wife of twenty-five years. I was in shock and so lonely I drank too much and took unnecessary chances with my life as the winds of change continued to blow strongly. Every time I thought the winds were receding, they would pick up again threatening to blow me off my high heeled shoes.

I was fortunate when I saw the name of a doctor who would check me out and then prescribe HRT or gender affirming hormones and I took immediate advantage to do something I had wanted to do for a very long time. Sync up my inner person with an exterior which was feminized. Even with the minimum dosage I had to begin with, I could feel and immediate change in several areas such as with my emotions and breast growth. When I began to see myself as a different femininized person in the morning mirror, I was becoming more and more excited over the winds of change which were pushing me ahead into a new exciting world.  

The only part of my being who was not surprised by all the changes was my feminine self who had been hidden away all those years with no way to express herself as when she was in the Army. If patience is a virtue; she had it all as my male self-put on a tremendous fight to maintain what he had earned as far as privileges went. Fortunately, the winds were blowing in the right direction, and she won the ultimate battle for my life. I discovered that without her, I would not have had a life worth living.