When We were Against the Law

 

Phil Donohue on left with singer (male) 
Grae Phillips.

I am old enough to remember the days in Dayton, Ohio when transvestites and or cross dressing men were loaded into police vehicles and arrested. 

Since I was just discovering my attraction to feminine clothes, of course the whole process scared me. I did not want the police to come in and arrest me. Then, the Stonewall Riots happened in New York City in 1969 and all of a sudden there was a glimmer of hope for me again. The outside world was changing, or so I thought as I watched and learned from my home in faraway Ohio. I was in my second year of college and the world was changing for me also. As the world on occasion seemed to tip in our favor when movies such as "Tootsie" were released in 1982. 

Then there were the flood of talk shows from "Phil Donohue" to" Jerry Springer" who focused on the the so called married cross dresser and wives. Many were trash and did the transgender or cross dressing community any good.  Donohue ran from 1970 until 1996. Sadly we were left with being items of ridicule on "Springer. " We were not against the law but close. 

Now of  course we face the most difficult times a transgender woman can face. If the orange menace and his cronies find their way into power, we in the entire LGBTQ community face a real threat to our very existence. I live in Ohio and the anti-transgender political ads against Democratic Senator Brown have been ridiculous. In fact they out and out lie. What amazes me most is when I encounter a pro-tRumpt transgender person. I have had them tell me they believe him when he says he had nothing to do with Project 2025 and they are safe with him in office.

I stand with all women and support their right to control their own body. I also stand with the candidate which does not threaten our future existence as transgender women and trans men. I think you know who I am referring to. 

I know nothing I can say can influence your vote. In fact, you may have already done it. I just hope enough see through the barrage of lies and vote in our first woman president.  

Picking your Poison

 

Dinner with my wife Liz
on left. JJ Hart on right.

Before we get started on this post, let me repeat again and again a transgender woman's or trans man's path to living an authentic life is NOT a choice.

Somehow for reasons we are never aware of, we are born into it. At that point we are forced to pick our gender poison when we decide to follow our instincts and transition or decide to stay in our closets for whatever reason. 

Most of the reasons on either side are compelling and not wrong. Reasons include major implications include facing problems with employment, family and friends. When faced with any or all of these challenges make a closet a more comfortable place to be. Or is it? Do the problems ever go away? The answer of course is no and picking your poison becomes a bigger problem. In my case, I became increasingly caught between my own personal gender rock and the hard place. 

On one hand, I appreciated the unwanted but over appreciated male privileges I had earned the hard way. But, on the other hand, I increasingly felt natural and excited by the new feminine spirit I was feeling. The main problem I had was knowing deep down I could never go back to my male life but could not face my own truth and the process then began my poison. The longer I progressed on my gender path, the stronger my poison became and the only anti-venom I knew was to keep exploring the world as a transgender woman. I became so engrossed in my search on occasion I forgot my old male self altogether. In a short period of time I was facing cruel and unusual punishment. Mainly because I needed to internalize all my poison and the process was lonely and unfruitful. What about key questions such as my sexuality? What would my future life look like. 

All too soon, I knew my poison was also my strength. I just knew I had to stay on the path I was on to finally achieve my gender freedom. I was fortunate, I escaped my closet and was able to achieve my ultimate goal of earning my transgender womanhood. The entire process was not without stress and failure along the way. It was like I was living the ultimate trans woman's days out. I needed better times in my life just to survive in the world. Often I just was confused in how I was going to spit out my poison and achieve my dreams. As I said, I was on a lonely path and needed any light I could focus on to help find my way along. It was like I was carrying the darkness of my closet with me. 

As I was planning to go away and throw (or donate) my male clothes out, I needed to make sure I was picking the right poison when I found a trans woman's life was not all sweetness and light. Entering a woman's world meant I needed to be better than the average other woman just to survive. On the other hand, I found all the life I had lived on both sides of the binary gender border gave me more experience in the world as a whole which helped me to survive. 

In my world picking my poison and being able to escape my dark closet was the only way to go. Being a guy was always difficult for me and learning how to live as my authentic self was even more difficult but was so much more natural and enjoyable. 

Reaching Out for Truth

 

Image from Jen Theodore
on UnSplash.

As I transitioned into my form of transgender womanhood, first I needed to find my own truth. In order to do it, I was placed in a dilemma. 

The dilemma was I needed to make sure my gender journey was taking me in the right direction. I needed to make a huge life changing decision so I needed time and experience to make certain I was taking my life in the right direction since essentially I was risking everything to do it. In other words I needed confidence. 

Gaining confidence proved to be a fragile thing to find. I would have it following a successful day out away from the mirror as a novice transgender woman when I seemed to do everything right. My makeup, wardrobe and wig were on point and I even carried myself fairly well. I was building the life I always had dreamed of and seemed to be within reach until the next time I went out and everything crashed and burned. Either I did something very unrealistic and was laughed at or my overall appearance just wasn't right. Whatever the problem was, my fragile confidence was shattered. And, as we all know, confidence is our most powerful accessory. Humans are similar to sharks, if they perceive something is wrong with you, chances are the other human could act on it. A big turning point for me was when I arrived at the point where I did not care what anyone else thought of me. 

Actually, let me re-phrase that. I did not care what men thought of me because for the most part they had all felt as if I was from another planet anyway and wanted nothing to do with me. On the other hand, I did care what other women thought about me. Since I needed other women's acceptance to exist in the same world they were in, I needed their approval. In order to survive, I needed to be honest to myself which in turn, made me honest to them. I was not hiding anything. I was upfront on what I was trying to achieve which was to give up my old life as a man. Very quickly I learned I appealed to more women as a friend than I ever had as a man. I thoroughly enjoyed my learning curve as a transgender woman and wanted to build on my truth even more.

Even still, on occasion, I was still having issues with living my truth. My biggest hurdle to conquer was myself. I was the last to know my truth because I hid it all so well. To my everlasting shame, I even lied excessively to my second wife about what I was really doing while she was working at night. So, by osmosis, I was lying to the two closest people to me. Something I am certainly not proud of. However, I am proud of the fact I did reach out and grasped my truth during my long life. 

It took me long enough to do it. I struggled for over fifty years as a cross dresser and went through so many stages of attempting to figure out who I really was. I was so much more than a man who liked to wear women's clothes, I wanted to be a transwoman wearing women's clothes. Once I learned this major truth about my life, finally everything came into focus. 

Into One Club and Out of Another

 

In the Women's Club. I am on the bottom row
to the left.

As I transitioned into transgender womanhood, I learned how quickly I could be pushed out of one gender club and make my way into another.

The first club I was quickly rejected from was the good old boys club which I was tired of anyhow. I quickly found many of the gender stereotypes were true. My primary example was and is when I am in a conversation with a man, I seemingly have lost a good portion of my intelligence. In many ways, I was expecting it because of the way I had seen many men around me in my life treat women. I wanted a change in the worst way.

Of course leaving one club and being accepted into another was not going to be the easiest thing I had ever done. As I set my course into the world of women, initially I was met with little resistance except for two key people in my life. Along with my second wife who hated the idea, of course my male self was dead against it also. He was the one who was getting kicked out of the club.

One of the first aspects of being accepted into the woman's club I learned was to look for the hidden knife behind the back trick. All of a sudden I was in the world of passive resistance. Some women did not like the way I looked or acted all the way to resented my presence in the club all together. Rather than tell me to my face, they worked behind my back to drive me away. I came away from the learning experience with many claw marks on my back. I considered it all as a initiation experience into a new exciting world where all I wanted to do was play in the girl's sandbox. What I never counted on was how complex the new world would be. I knew women were much more complex than men but slipping behind the gender curtain and living my dream proved it.

I fought hard to keep my dream from becoming a nightmare. First there was the problem with learning how to dress myself so I could stand a chance of blending in with the other women in the world. Then there was the problem with learning how to go with the flow, or practice moving like a woman and last but not least, there was the problem of learning to communicate with the world in my new club. The more I progressed with all of this, the more I did not want to be forced back into the male club because the pressure was constantly there. Going back meant leaving all the gender struggle behind me and regaining all the male privileges I had lost when I entered transgender womanhood. 

Somehow, I always managed to keep my dream alive and no matter how beneficial going back seemed to me at the time, maintaining my hard earned membership in my new club was more important to me. I had served my time in an unwanted male existence and had no desire to return. So I continued to spend time in my new club as a transgender woman and learn the benefits of living an authentic life. 

I never really missed the benefits of living in the male world.  Then I needed to set out on the complicated process of telling all of those who thought I was still in the male club, I was not and please listen to the reason why. Some people and family I was successful with and some I was not but none of it kept me from trying. My main goal now is to keep my membership in good standing in the transgender woman's club.

What I Really Learned at Halloween

Kenny Eliason image from UnSplash.

 Sadly, since I have lived over ten years as a full-time transgender woman, Halloween has become just another day to pass out candy to any kids who may come by the house. The neighborhood is becoming older and we don't have the influx of kids we used to have years ago.

Regardless, I still have fond memories of when I went all out for Halloween. I used the experience as a testing ground to see if I could actually go out into the world as a woman and live. Throughout the month, I have focused on several Halloween adventures I had. When I first started, I thought dressing sexy would validate myself as a woman. Then I started to tone down my "costumes" all the way to going to the last party I remember dressed in feminine business casual attire which I was used to presenting in the upscale malls I was going to. 

The party itself was sort of a who's who of invitees held at a real live Victorian mansion in a restoration district in the town I lived in. I received my invitation because I was a fairly well known radio disc jockey in town at the time and happened to know the couple putting on the party. I knew immediately what I wanted to wear and just needed to decide who I wanted to invite to come with me. I knew my first wife was not into Halloween and wouldn't care if I invited someone else to go with me, so I invited the news-woman where I worked to go instead. An example of how easy going my wife really was. I always thought if I told her I was leaving for a month for gender realignment surgery, it would be fine with her. So the stage was set to be out and about as my authentic self. No playing around with a "costume", I wanted to be mistaken for the real deal.

Since there are no pictures from the party, my outfit consisted of a business suit, heels and blond shoulder length wig. Needless to say, my wife was not surprised but my date was completely. Mainly because of my shaved legs and how well I walked in the heels. When we arrived, thankfully, parking spots were not a problem and at the door, a coffin with a real skeleton greeted us . The mansion was really decorated well and we found a seat. 

Predictably, as the night went by, no one knew who I was and I blended in as a woman who arrived late from work and did not have a chance to find a costume. I was having a great time, when another couple came up and said how impressed they were with the way I looked and they thought I was a woman. Furthermore they were leaving soon to go to another party and wanted to know if we or I wanted to go along. Even though I was extremely flattered I turned them down but not before I found out who they were. The couple was a young congressman and his wife, leaving very soon to go back to Washington, DC. So I guess I destroyed any chance I had at a political career. 

What I really learned that Halloween was I could step out into the world as my authentic feminine self and survive. Very much worth all the time and effort I had put into to being a girl over the years. And, as far as the news-woman went, she never said a word.  

I guess you can say with out a doubt although the thrill is gone for my Halloween, the day more than any other one in my life served a wonderful need when I did not have any other outlet.

Set Her Free

Image from JJ Hart

Throughout my long life, which included fifty years of being a cross dresser, I could feel the stress and tension of not freeing my inner girl.

It all started innocently enough with trips in front of our family mirror in clothes I had borrowed from my Mom. Of course that all ended when I outgrew her sizes and I needed to strike out on my own to find fashion which fit. With my meager allowance and money I made from delivering newspapers to the neighborhood, I managed to get by and buy a few items to add to my wardrobe which then I needed to carefully hide away from my family.  Somehow I survived and my life as a male set in, no matter how much I did not want it to. 

The gender stress and tension continued over the years and even became worse with every success I had when I tried to set my inner self free. It finally became evident my entire gender life was backwards, I was not a man cross dressing as a woman, I was a woman cross dressing as a man and it was no wonder I was feeling the confusion and pain. I would not have wished the mental anguish I felt on my worst enemy. I found being transgender was far from being a choice and somehow I needed to set her free.

The problem was, I needed to face the same set of hurdles transgender women and trans men face. Such as family or spouses, friends and occupations. The longer you go in life, the more gender baggage you acquire, the more you have to get rid of. Or figure out how much you can keep. My prime example always is how I was able to maintain my love of sports when I fully transitioned into transgender womanhood. I had help when I learned the women around me loved sports as much as I did and I felt right at home. It was easier to set my woman free. 

Finally, I arrived at the point where I could take it no longer. I ended up living more time as a trans woman than I did as my old male self. So much so, I was feeling totally out of place in a male world as a guy and would have rather attacked it as a woman. Plus I still had the age old problems of doing my best appearance wise as a feminine person. I began by losing nearly fifty pounds and taking better care of my skin on a daily basis and worked my way forward from there. Through days of trial and error, I was able to arrive at a point where I could provide a reasonable attempt at presenting as myself on a regular basis. The key was to settle in to what myself should look like which meant stopping doing things such as switching wigs on a regular basis. Finding who I was proved to be the key to setting myself free.

Once I did manage to set my dominant self free, she did all the rest. I learned to keep my old male self out of the way and let her go. Among other things, she picked my friends and lover and opened the door to a life I never thought possible.

It was like she was saying I told you so and should have done it sooner. 

Fall Leaves

Image from Alisa Anton
on UnSplash. 

I write substantially how fall is my favorite season of the year. I love the cooler temperatures, wardrobe changes and how the trees change into their brilliant colors. All before the colors go away and drab winter sets in.

Long ago, I felt all the seasonal changes deep down to my inner soul. Of course as a novice transgender woman the wardrobe fashion changes were challenging and fun. I learned I needed to look ahead for the best clothing bargains if I was to be successful in locating all the fashion firsts in sizes that fit me. After a few seasonal changes, I began to feel so natural, I automatically felt the changes coming on. Fall was especially fun when it was time to go through all of my leggings, boots and sweaters to see what I would have to add or subtract to make it through another season.

Even though fashion changes were exciting and fun, other aspects of the season just brought about melancholy depression. I vividly remember the nights when I went out and just drove around in my car watching all the leaves blow around in the headlights. Here I was still stuck in a gender I did not want to have anything to do with and not seeing a way out. Very soon, the fun of fall would turn into the depression of winter for me. My final fall before leaving for Army basic training was especially bad because I knew for a fact I would not be able to do anything about my transgender desires for a very long three years of my life. It seemed so unfair my new life into transgender womanhood would have to be put on hold through no fault of my own. I was bitter. 

Little did I know, after waiting over two years out of three in the Army, karma would come back to help me. During my last year I learned of a Halloween party which was being planned by a hospital group which my friends and I were invited to. Immediately my mind jumped to the possibility of me dressing up as a woman and going. Of course the problem arose how was I going to do it because I did not want to go halfway. I wanted to be the sexiest dressed woman at the party. Fortunately, I had access to an apartment where I could finally shave my legs and put on makeup with a wig I managed to buy at a downtown Stuttgart, Germany shop where I was stationed. Through it all, I knew I was risking harassment or worse by my superiors in the Army if the word got out about my so called "costume" which may have been a little too good. But nothing ever happened.

In fact, because of the Halloween party, my life changed nearly full circle that fall. A couple of days after the party, when my closest friends gathered once again over potent, tasty German beer I blurted out the costume I wore was more than a casual fun idea I came up with on the spur of the moment. I was a transvestite as we were known back in those days and I enjoyed wearing women's clothes, makeup and wigs. I knew at the time, again I would be risking what was left of the time I had left in the Army if what I said found it's way into the wrong hands. It did not matter at the time as the first time I left my gender closet felt so good. So good, I tried to come out to my Mom who promptly slammed me back into my closet. 

All of this happened during the fall which still remains my favorite season of the year. As a  transgender woman, I appreciate the re-birth of spring but summer is too hot and winter is too long and drab. It's why fall leaves are so important to me.  

Connections through Isolation?

 

My wife Liz on left
from the JJ Hart Archives

When I finally began to be successful in my femininized public pursuits away from the mirror, I was content to be alone in the world.

By being alone, I didn't have to face any communication problems with anyone else I faced. Essentially, I just passed through their world quickly and was gone. I did not want to know them better and have to challenge myself into interactions with strangers. Ironically, my idea did not last long as I was increasingly thrust into public interactions as a transgender woman I did not want. In the beginning, I just was not ready to look another person in the eye and risk ridicule.

I learned quickly, my public interactions would be overwhelmingly with other women. Initially, I interacted with clerks in clothing stores who were mainly interested in helping me with my money, except for the few who wanted to help me with my fashion. It did not take me long to realize what was going on and then move on. 

I began to stop and eat lunch to extend my shopping trips which meant ordering from a menu with a server and/or bartender. I found sitting at the bar made for a more personal experience unless the staff was very busy with other patrons and I could try out speaking with others as a trans woman. Very soon out of forced habit, I found myself relaxing more and even enjoying the experience. It was like I was completing a long lost part of my new personality as I left the mirror and entered the world. It was a challenge and I grew to love it. I discovered also many more women than men wanted to know more about me. Women were curious while men were scared of me it seemed and I loved it. 

Along the way, when I first began to communicate I tried to mimic the voices I was hearing from other women and try to repeat doing it until I thought I was doing it right. I even took voice lessons for awhile to improve my vocal presentation for my transgender womanhood.

Still, after my second wife passed away, I was extremely lonely. Not only was I facing finding another person I loved at the age of sixty, I also had the added pressure of doing it as my new version of my authentic feminine self. I was prepared to spend the rest of my life by myself. Little did I know I would not have to. Initially, when I went out to supposedly socialize and find new friends, I was going out to be by myself. If my gender was never challenged I would have taken the easy way out and would simply go back home to my two dogs. 

If it wasn't for a bartender at one of the venues I had become a regular in, I would have remained in the social rut I was in. One night not long after I arrived, she served me my first drink and quickly asked me if I would be interested in meeting her single lesbian mother. Of course I said yes, and a friendship  started that has continued over ten years till today. She is the woman who took me to the NFL Monday Night Football game. A very scary experience which cemented my arrival as a full-fledged transgender woman in the world. But that wasn't all that happened at my favorite venue. Another night, as I sat alone to be by myself, another woman came in to pick up her to-go order. While she was waiting, she slipped a note down the bar to me asking if I was interested in having a drink sometime. I said yes and the three of us ended up having a great time the next couple of years as we watched sports, drank too much and had fun at lesbian mixers. My two new friends ushered me into a world I never thought I could go.

Against all predictions, my connections through isolation worked very well for me. My new friends which included my wife Liz who also identifies as a lesbian, all helped me into my own important version of transgender womanhood. Destiny was certainly helping me during this period of my life.  

Seraching for Me

Image from Selcuk S
On UnSplash.

Ironically, during my life I have spent too much time searching for who the true me was.

Naturally, I am referring to finding the springboard I needed to determine which gender I was. When I was younger, I made the habit of waking up in the morning wondering if I was a boy or a girl. I was very gender fluid for years before I decided which gender direction was the correct one for me. The problem was I needed to put on my gender blinders and attack the world daily as a male. Something I never wanted to do.

It turned out the springboard I needed to find out the me I was looking for was still a long way in coming. I still needed to cross or follow many paths before I found me. More precisely, I had parenthood come into my life as well as many challenges such as military service, marriages and just life in many ways. I was constantly searching for my gender by going out and exploring the world to find out if I could ever achieve my dream of transgender womanhood. The journey was so difficult when I experienced negative feedback From stares and giggles, all the way to people singling me out for pictures, I did it all before I made a better effort to blend in with the rest of the world.

All in all, I found just being me was going to be much more complicated than I ever thought possible. It all started for me in the days when I always thought the grass was always going to be greener for me on the feminine side of the border. I discovered, even though my trip across the border was terrifying at times, on the other hand I felt so good and natural, I knew there could and would be no turning back. No matter how easy it would have been. At times, I was even a bit jealous of men who had never experienced any gender issues and were able to live out their lives enjoying male privileges. It all just was not in the cards for me during my life.

Just me, turned out to be so much more. I am a parent, a grandparent and a spouse to a supporting wife. In other words, I am so fortunate to be surrounded by people who care for me. Plus during my life I have been able to take an in-depth dive into how both main binary genders operate. What really breaks my heart is when one of the bigoted transphobic political commercials comes on with all it's lies. I want to tell the haters that even though I am a transgender woman, I have a life not so different from theirs. I am just busy being me.

Perhaps the problem is, since my life turned out to be more complex than the so-called norm, so people don't want to understand or care. 

By this time in my life, I have learned being just me will have to be good enough. I have worked too long and hard to give it up now. From having a gender fluid lonely youth to finding my true self in trans womanhood, I think I have been fortunate to end up where I am. Plus, I will continue to advocate for all transgender women or trans men such as my transgender grandchild with their whole life ahead. There is so much to do. Maybe I can just be a positive example to another novice transgender person still living firmly in their closet. Who knows? Maybe you can be next to escape and live as your authentic self.