Having an Affair

Image from Susan G Komen
on Unsplash

Years ago I experienced having an affair during my marriage  with my second wife. 

Before you condemn me any more than I condemn myself,  the affair I am talking about was with myself. That is right, myself. It happened when my feminine inner soul began to take over my life. What I was doing at the time was rejecting the pledge I had made to her to never leave the house cross dressed again. I became so entranced with how natural I felt in my transgender womanhood, I left the house any chance I could which was often. It turned out, the more exploration I went through, the more I wanted to do. Seemingly nothing was out of reach in the new exciting gender world I found myself in. Sadly, even to the point of leaving the vows I made with my wife behind. 

Let me point out also, I had never stepped away from my marriage during the twenty-five years before to be with another woman. Imagine my shock when I finally did, the other woman would turn out to be me. 

As is the case with many affairs, the passion was real in the beginning. Then begins to lessen overtime. In my case, the opposite happened. The more I explored and lived as a transgender woman, the more I wanted to do. I had a real problem on my hands on what was I going to do. On one hand, my wife had told me in no uncertain terms she would not live with another woman and on the other, I did not have the courage to tell her she already was. If I had faced reality, I would have known it was time to jump off the old male ship and begin to live a new life in a feminine world. Even though most likely, it would have cost me our marriage, perhaps we could have at least become friends in the future if she had lived. You see, she died of a massive heart attack at the age of fifty. 

The only thing I did do out of desperation was try to purge myself of most of my female belongings before she passed away and I even grew a beard. It turned out to be my last tribute to her and the years we had together. 

As with all purges, they don't last for long and one of the first things I did was shave off the beard and turn inward to myself in the lonely tragic days after her death. It took awhile but my inner female took control and let me know everything would be fine. Finally I decided she was right and decided to give up all the guilt I was carrying over the affair I had with myself. 

Once I did, my new life as a transgender woman took over. I found new friends and moved on but it took me five plus years to do it. In the meantime, I found all the work I needed to do to play in the girls' sandbox was worth it. I needed to be better than the average cis-woman to survive in the world I chose to live in. I found a woman's life had so many layers to it, I faced a real challenge. As big a challenge as having an affair in your marriage. With yourself.

Was there Ever a Plan

Image from the JJ Hart
Archives

Looking back, I needed a very definite plan to follow as I transitioned into transgender womanhood. 

Similar to so many of you, I started by "borrowing" a few of my Mom's clothing when I could still fit into them. I would have added a sister in but I did not have one. When I became old enough to do it, I took on a newspaper delivery route in my neighborhood and combined my new meager funds with the allowance I received at home from my parents and with the money, I was able to buy a few clothes and my own makeup. Since we lived in a rural area outside of town, the plan was to stay a day or two with my Grandma who lived very close to stores *downtown where I could attempt to shop for what I wanted. The problem with the well thought out plan was my Dad worked downtown too and he was the last person I wanted to run into with my new "treasures." 

After I conquered my fear of shopping for cosmetics I did not really need, I was able to buy makeup which did not make me look like a clown. Another problem I had was, the only example I had of applying makeup came when I was able to watch my Mom do it. I wonder if she noticed me watching her. She was probably so entranced in her face, she did not notice I was entranced also. 

The older I became, the more entrenched the plan became. I was able to increase my small "collection" of feminine wardrobe and makeup as I went along and managed to hide it from my brother and the rest of my family. At the same time, I wanted to become better at the makeup arts and finding clothes which fit me. 

At the same time, I became comfortable with how I looked in the mirror and increasingly had thoughts of expanding into the world. I did try to come out fully dressed to one of the very few male friends who lived close by in the neighborhood but was quickly rejected and I scurried back into my dark, lonely gender closet. I stayed in the closet until several Halloween parties began to bring me out. From then on out, my plans really began to change.

During the parties, I learned how much I enjoyed my time out of the closet and I just knew I needed to figure out a way to live as a transgender woman without waiting for a whole year to go by. To do it, I knew I would need to start by telling my spouse what I was up to. So the plan was to find out what wife number one and two thought about me being a cross dresser before we were even married. It turned out wife one did not care and wife two was supportive to an extent which helped me along. 

The main rule I had with wife two was to never leave the house dressed as a woman. I started innocently enough before I veered off course and threatened our marriage of twenty-five years. I began going to women's clothing stores and malls where acceptance was easy to come by. Money was certainly more important than gender. I also would go to bookstores and even antique malls where I could browse with no problems to build my confidence. When my spirits went up, I planned ahead for my next big adventure which usually meant beginning to interact with more of the world as a transgender woman.

To do it, I began to stop and eat at restaurants along the way to make sure I had to communicate one on one with a server or bartender. Since I had an extensive background in the restaurant/bar business, I knew basically what I needed to do to survive. Just be nice, do not cause any trouble and tip well and I could be successful. 

From then on, I endlessly planned on what I was going to to next and how I could challenge myself in the feminine world. Sometimes I was successful, sometimes I was not but I always learned from the experience. In my life as a man, I had never really planned ahead on anything, so this was a big difference. Perhaps it was because I could not wait to try again to live out my dream of transgender womanhood.

*Those were the days of strong vibrant downtowns in many cities, including mine. Before malls took over and they tore the downtowns apart. 

All I Ever Knew

Circa 1940 image
of Virginia Prince

 Every once in a while I receive the question when did I know I was transgender.

The easy answer is I always knew but I needed to figure it all out. The more complex answer is I needed to figure it out after a series of transitions during my life. Two major ones occurred when I made the jump from from a very serious cross dresser all the way to a novice transgender woman. The second problem I had was back in those days, terminology to define a transgender woman or man had not yet been invented. Basically back in the pre-internet days when all we had was the preaching of Virginia Prince and her Transvestia publication which I could not wait to receive in the mail. Seeing all the pretty cross dressers just made me want to do more to improve my feminine appearance.   

I worked harder on my appearance than any thing I had ever done before and slowly began to see improvement over my testosterone damaged male body. It was all I ever knew. 

As I entered my transgender womanhood, I felt deep down inside I was doing all the right things, even though I was jeopardizing all the facets of my male life I had worked so hard to put together. What would I do when my family, friends and bosses discovered my deep secret. It ran so much deeper than just wanting to wear women's clothing. I wanted to be a woman and live a feminine life. 

During that portion of my life, I basically went into attack mode, doing every thing I could to learn how being a transgender woman would affect me. Every free moment I had, either I was out in the world as a woman or day dreaming of the times when I could. Naturally, I learned a lot, good and bad about what life had in store for me if I kept on going towards my gender dreams. I found the grass wasn't always going to be greener on the other side of the gender border as I lost all of my male privileges but hadn't gained any of the female ones. 

Soon I learned, it was truly all I ever knew. Somehow I was born to be feminine and not masculine. Which meant years of struggle to right the gender wrongs I was living. The struggles on occasion were crushing and keeping going was very difficult but I did. Probably because I was behind before I even started. I was born into a very male dominated family which had very few girls to play with. Plus, I never had any feminine characteristics myself to begin with. Add it all up, then include me never having any girl time with anyone all teamed up for a rough start for me on my gender journey.

Even still, my gender path was all I ever knew and staying on it finally made me successful. 

It is In Your Nature

Image from Hannah Popowoski on 
UnSplash

Following my fifty year battle with my gender issues, I just gave up and went with what felt so natural to me and completed my transition into transgender womanhood.

It was certainly a long drawn out journey of self discovery. It was full of ups and downs as I gained my footing along with confidence as I learned to just be myself. Looking back, I don't know what took me so long. Perhaps I can blame it on my male self wanting to hold on to the lifestyle he worked so hard to survive in. He put up quite the battle before giving in. But give in he finally did. 

When I finally began to explore the world, I learned how much of it was run by women and in order for me to survive, I needed to get along one on one with the other women around me since men rarely showed me any interest as a person. Women on the other hand were curious why I was in their world and I was somehow valued for being there. Perhaps it was my honesty showing through, which I gained from jumping the gender border into their world. I don't know for sure but I loved the attention I was getting. 

It was in my nature, because I had always valued the women friends I had over the very few men friends I ever was capable of having. I just did not fully ever recognize why until I was fully allowed to play in the girl's sandbox. Before I was allowed in though, I needed to earn my way in. I had to show my true nature was feminine and I needed to learn the rules of a brand new gender game. For example, I found myself in a world where passive aggressiveness ruled and a smiling face did not mean it was a friendly face. Much different in the world of men I was used to. It all was more of a mental game than I was used to also as I tried to anticipate where another woman was coming from. Especially when I came down to interacting with their men. On a few occasions, I came too close and felt the claw marks down my back for doing so.

The whole process just made me stronger and more confident in the woman I was becoming. Quickly I felt as comfortable in the new world I was in as I learned how the gender game was played. Women are more apt to form cliques than men who form teams and instead of finding the alpha male for acceptance, I needed to find the alpha female who was running the clique and I was in. 

Once I was in, my life became so much easier. Primarily because I did not have to fight being two genders anymore and the inner woman I was hiding for so long had her chance to run the show. She took to the process naturally. The only thing she did not do was harass me about why it took me so long for her to take over. Which she had every right to do. More importantly, I found she was a good person and got along with people including the all important world of other women. Essentially I found I good set and enjoy the show.

Of course before I could enjoy the show, I needed to understand the process of how to blend in with the world as a transgender woman. It was difficult putting my old male ego aside and realizing I was never going to be the most attractive woman in the room, I could present well enough to survive if I had the confidence to do so. 

What I really learned was, it was all in my nature to do so and if I relied upon it, I would be fine.

Breaking the Gender Chains

 

Image from Arlem Lambunsky
on UnSplash.

For years and years I blamed myself for my transgender issues. 

I did not have access to the proper information to know otherwise. I thought somehow I was addicted to seeing myself in the mirror as a femininized person. The chains of being a male person weighed heavily on me. It was not until much later in life that I had the chance to learn I was completely wrong and I had never really had the choice to attempt to break all the chains which were restricting my life. All of this occurred in the pre-internet years and it was not until I bought my first computer did I finally began to see there were others just like me who struggled the same way in life.

At approximately the same time, I began to meet more and more diverse individuals in the new LGBTQ community. Primarily, I learned the difference between cross dressers and transgender women and men. Those involved in pursuing a life in transgender womanhood were much more serious than the average cross dresser who was actively embracing how they appeared as a woman. I was able to meet several impossibly feminine transgender women who embraced being a woman, not just looking like one. At the time I was intimidated and wondered if I could ever make the jump myself. Plus, I knew before I attempted such a radical move, I had quite a bit of work to do on myself.

I became the mistress of excuses of why I could not break my gender chains and move forward into the great unknown. What would I do about the remnants of my male life and what if anything would I do about my sexuality among with other important parts of my life. One thing I knew for certain was my desire to live as a fulltime transgender woman was more than an addiction because the process felt so natural and affirming. The entire process was stressful and damaging to my mental health because I was firmly stuck between the two main binary genders.  I would have not wished the stress I was feeling on my biggest enemy and the worst part of it all was  how I needed to internalize my feelings to the world. 

Life was so black and white at the time. Half of the time I was in the darkness of being chained to the wall of my old male life as I daydreamed of the lighter times when I could explore again and again the times I had as a woman. 

Through new woman friends and a good therapist, I was able to break out of my old gender chains and live my dream. Proving time and time again I was living the life I was meant to live. In no way did I have any lasting attraction to just wearing woman's clothes. The clothes were just a larger indication of how I wanted to live my life and were an external view to the world  which enabled me to open gender doors which were previously closed to me. 

I could not believe after the chains were broken and the new doors were opened, how much brighter my world became. Somedays I wonder if the wait was worth it. 

Outreach the Easy Way

 

Out with my wife Liz
on left.

Last night, I took Liz and her son out to a steak house for her belated birthday dinner. She is a big fan of a good steak. 

To show you how popular the place is, we needed to wait for an hour for a table. There were not even any seats in the waiting area, so we had to wait outside on a solid metal seat. Fortunately,  the weather was unseasonably warm and dry so all we had to do was watch the other customers come and go. By doing so, I was able to notice the amount of fancy pickup trucks in the parking lot. A fancy pickup truck in my mind will forever tell me the driver is a fan of the new president I dearly dislike so I wondered if I would face any negative feedback from being transgender in the restaurant.

Once we finally made it into the venue, the pressure was on to see what everyone else thought of me. My fears proved to be unfounded. Even though the other people in the lobby had nothing else to do but to people watch, nobody zeroed in on me. I was essentially invisible to the world which is what I wanted. Men, women and children ignored me as they fidgeted, all waiting for a seat.

To be sure, it was not always this easy for me. I went through years learning the art of makeup and fashion I needed to transition out of a male world and into a feminine one. I was stared at the least and laughed at the worst when I went out to eat. All along I was a woman on the inside just waiting to get out. I was in my own version of gender heaven and hell. It all paid off when I have experiences such as last night but sadly I still have scars from unpleasant past experiences. 

By this time, you may be thinking I am a person with a huge trans ego problem. My second wife was fond of  telling me my femininized life was not all about me. She in most senses was not wrong, I was going all out to be the best cross dresser or novice transgender woman I could be and I needed to watch the room and other people around me to judge how I was doing. There simply was no room for anything else in my life on most days. 

It took me years to learn to relax and enjoy my new transgender womanhood as I was too busy still trying to read the people around me. Last night was one of those rare evenings I could relax mainly because I felt I looked nice, sounded confident and even felt physically better which all contributed to a fun evening. A good night of transgender outreach to all those pickup drivers who saw us portrayed as monsters during the previous election. As I look to the future while I process my past. 

What did I wear? My The Ohio State University sweatshirt, jeans and tennis shoes to blend in with all the other Ohio State fans in the venue wearing their fan gear. However, I did step up my hair and makeup with eye makeup, foundation and lipstick. So I wasn't a total plain jane. 

Whatever it took, I needed to blend in with the masses at the steakhouse and I did, they were not interested in me which was good. Outreach invisibility at it's finest.

If You can see it You Can be It

 

Image from Trans Ohio party JJ Hart.

Long ago, when I first glimpsed myself in the mirror as a feminine person, very soon I realized just seeing myself was not enough, I wanted to be the girl I was watching. 

In the classic if I had known then what I know now, I would have known then I was less of a cross dresser and more of a transgender woman. Way before the term transgender was ever used. Now more than ever before, it is time for us to blend in with the public at large as transgender women or trans men. We just have to be better and better.

Fortunately, I had years of preparation to be ready to face the world. Since I had plenty of testosterone poisoning to overcome, there was work to be done and I needed the courage to do it. Along the way, I viewed the whole process as stairsteps towards what I perceived as an impossible dream of transgender womanhood. Facing the world with confidence was my biggest problem. Every time I took a positive step forward when I went out in the world as a novice transgender woman, it seemed then I faced several steps back. When I was on point with my fashion and makeup, I lost it with my voice. Or vice versa on other days when I caught myself slipping back into my old male ways and walking like a linebacker. Adding to my problems was I was still trying to maintain a life stuck between the two main binary genders which made my existence even more difficult. I needed to consciously think all of the time which gender I was dealing with the world as. I was in.

Very slowly, I worked through this phase of my life and found women friends who I could learn from. I learned I could relax with them while at the same time learning how it was in woman only spaces. At the time, when I looked in the mirror, I was seeing it and being it which felt wonderful and so natural I knew I was in the right place. For the first time in my life, I thought my dream of leading a feminine life could be realized.  

Through it all, I still needed to work on my makeup and fashion skills to blend in with what my lesbian friends were wearing. It was a challenge because I needed to look as if I was not wearing any makeup at all when I was. I needed to work harder than the average woman to succeed in the world. By this time, I was used to it and worked hard to instill confidence in what I was doing with my gender goals since there was so much at stake. I was playing a high risk game with my life. Was the grass really greener on the other side of the gender border. 

I found out indeed the grass was greener but often not so easy to enjoy. I met more than a few women who did not want me in their world and did not hold back on their dislike for me. When they did, I needed to quickly pull the knife out of my back, smile and move on to friendlier situations. 

By this time, I was so close to seeing my dream goal of transgender womanhood, I pushed on even harder. I started gender affirming hormones with my doctor's approval. When I did, the changes came quickly and naturally as my body adapted to the new feminine hormones. Predictable changes such as hair and breast growth were quickly proceeded by inner changes with emotions as my life suddenly became softer. With my softer skin my facial changes were fairly dramatic and I knew then I could see it and be it.

As with any other long journey, you wonder was it worth the time and effort. With me the trip from the mirror into the world and beyond was just finding my true self. 

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. 

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.  

Halloween and Gender Breakthroughs

Halloween
Image from
the JJ Hart
Archives. 

Back again we go to Halloween and the effects it had on me as I developed into a novice transgender woman.

Very early on I learned when I cross dressed head to toe as a woman for a Halloween party, I would be cut out of the male club and my male friends would ignore me. Very early signs of losing any male privilege I had built up over the years. On the other hand, I was not ignored by many of the other women I knew from before who took the time to comment on my shaved legs and "costume." Both were small but definite signs of what I would face in the future if and when I decided to enter the public as a transgender woman. 

Over the years, my tastes in Halloween "costumes" changed from just wanting to be slutty, all the way to trying to present myself as a cis-woman would at a party. Plus I needed to overcome any fears I had of going to the party as a woman and mostly giving up on having a traditional good time partying with friends I had known for years. Again, just a small dose of what it would be like to cut all ties with my old male life and start all over. 

Everything began to change when my "costumes" began to evolve. One party in particular stands out in my mind. It happened when my second wife and I were living in the metro New York City area and I was managing a food location. It just so happened I was invited by one of my assistant female managers to go with her and several of her friends to a Halloween party they were going to. Without hesitation I said yes and wondered how I was going to explain it away to my wife. She never was into Halloween much and turned out she did not much care so I set out to put together an outfit for the evening. I decided to go semi-sexy (or try to) and chose my short mini dress, heels and dark wig for the evening. Off I went into the great unknown of not knowing where I was going and with whom.

It turned out, where I ended up first of all was at the house of my manager and to my pleasant surprise I learned all of her friends who were going were all tall attractive women dressed approximately the same as I was. As I walked into the room where they all were waiting, you could have heard a pin drop as they all looked me over from head to toe. Once they realized who I was, off we went to the real party which was being held at a small bar near to her house. The first thing I thought of was how far was I going to have to walk in my heels but the distance was not too bad and I was on my own cloud nine. I mean, here I was with three other women my height dressed the same way headed for a party. I was scared but excited by the time we arrived at the venue. Once I got to the bar and had a drink or two I started to calm down and learned another couple of gender break throughs. 

The evening turned out to be my first ever girl's night out because I was able to blend in so well with the other women I was with and I learned the power of being able to blend in with the feminine world. The second big breakthrough I learned was how to handle being approached by a man who perhaps did not know he was talking to a transgender woman. I was even asked to dance by one man. Finally, I learned single women of a certain age have a tendency to mark out their own territory when it comes to attracting male companionship. Once we all arrived in the venue, I was left very much on my own. 

I did not know it then, but all of the gender lessons I learned would come back to help me later in life. So much more than an empty comment about how good my shaved legs looked. As my second wife kept trying to tell me, I hadn't paid my dues yet to be considered a good feminine person. Trans or not.   

Transgender Instincts

Image from Atich Bana 
on Unspalsh. 

 First, I need to apologize for missing a post yesterday. I went to my primary provider at the local Veterans Administration clinic for my semi-annual checkup. While  I was there, I was able to receive my flu and Covid vaccines at the same time I was having my blood labs completed. By the time I had stopped and picked up lunch on the way home, I was pretty much ready for a nap and just laid down. By the time I woke up, I had ran out of time to do a post at all.

The visit itself was very mundane and I did not receive any negative responses at all and was never called "Sir." So I chalked it up to a win. In the past I wasn't so lucky and thought about reporting a couple people there for their transphobic behavior. For whatever reason, things have changed for the better. 

Now, onto instincts we have to develop as transgender women or trans men in order to survive in an often hostile world. Especially true for trans women. It seems we have to be on point at all times with our appearance just to get by and appearance is only the beginning. We need to move smoothly like a woman and learn to communicate one on one with mainly the other women we meet. I know I was petrified when I first was trying out the world as a transgender woman. Then, on a totally heightened level were the aspects of conquering and feeling comfortable in women's only spaces such as rest rooms. Which always is a topic for another blog post. Except when it came to the times when I was stuck in line at a restroom  and needed to make polite conversation with other women. 

These days, having your instincts about you as a woman, trans or not, is more important than ever before.  Depending on where you live, outspoken gender bigots have made our business their business. Plus as we transition into the feminine gender world, we need to be careful when it comes to our personal safety. In particular ignoring dark, deserted places such as sidewalks and parking lots. In particular, all things cis-women learn from a young age. Of course, I needed to find out the hard way about my own safety issues and was lucky I did not find myself in more serious harm than I did.

Sometimes, I feel interacting with the world as a transgender woman has meant developing a sixth sense. For me, my hearing improved as I strained to hear what someone else may be saying about me behind my back. From then on it is my decision on what do next. Recently, I have decided to stare the person down and even challenge them. I have spent too many years living to do anything else. 

Our instincts are powerful basics in our lives and changing genders brings a huge challenge. We have to start all over and learn our lives again. Being transgender women or trans men just brings a bigger challenge. On the other hand, learning to play in the other genders sandbox presents a unique challenge in life which very few humans will ever realize. 

Hopefully, we all can make the best of it and go though a safe and stable gender transition. 

Becoming Me

Image from the 
JJ Hart
Archives. 

As I bridged the gender gaps in my life to survive, I did what I perceived to be cross dressing as a woman in my family's mirror. 

Slowly I began to learn the makeup and fashion tricks the girls around me used to look their best. At times it seemed I was attempting the impossible as puberty set in and my body began to go through many unwanted male changes. Like it or not, I was stuck with testosterone poisoning and I would somehow have to get use to living with it. I was becoming a me which was very much unwanted. 

As I got by in life, I learned to camouflage my broad shoulders, and torso (among other negatives) and try to emphasize my positives, even if I needed to do it with feminine style padding in all the right areas. Since I was told I had good legs at the Halloween parties I went to, naturally I tried to emphasize my legs when I dressed. 

Sadly it took me many years to learn the truth about myself. Yes, it was true I was a cross dresser but not the way I always thought I was. In no way was I a male cross dressing as a female, all along I was a woman cross dressing as a man. Once I arrived at that point in my life, suddenly everything began to be so much clearer. I just wish I could have come to the realization so much earlier than I did. I always use the excuse to myself the world itself held me back in the pre-internet years before very little was being published or researched about gender issues. In fact, I still remember in my youth the news stories about the police rounding up and arresting men dressed as women. How could that be? 

Still I persisted and remember vividly the night I dressed up in a mini skirt, panty hose, heels wig and makeup and headed to a nearby gay bar when my wife was away. I was so scared and once I got there and was admitted through a locked door, I only had one drink and left before I even relaxed and I never had the opportunity to go back before the owner died and it closed. Even still, my adventure that night helped me to become the transgender person I wanted to be. At that point, the problem still was, I did not totally know who I was, or face up to her yet. But I was diligently working on the problem by researching my feminine life. 

To do the research, I needed to risk everything and leave the safe surroundings of the mirror and enter the world. I started with going to more gay venues and becoming quickly disillusioned when they all thought of me as a drag queen. Lesbian bars were better but I did not find true acceptance until I became brave enough to go to straight places. There I could watch my sports, drink my beer and become accepted as a regular fairly quickly by the staff. I minded my own business, tried to be friendly and tipped well and was in. Even though I knew they knew I was transgender. it did not matter and along the way I think it even helped me. One way or another, I was taking giant steps towards being me and I knew there was no way I could ever go back.

Perhaps the biggest step I ever took on the gender path to being me was when I started on gender affirming hormones. After being approved by a doctor, the changes occurred quickly.. In addition to the external changes such as breasts, hair and skin, I experienced internal changes also. My emotions changed as well as my whole life just softened. The entire time of gender adjustment was one of the most magical times of my life. 

Overall, the discovery of who I really was as a transgender woman was a terrifying yet exciting journey. One I don't regret taking, once I faced up to her, I was so much happier.   

The Prom Gown

Image from Joeyy Lee
on UnSplash

Years ago, I received a prophetic statement from an unknowing doctor when our family was on vacation in Canada. 

When we were not out fishing with Dad, we played football on a hard-packed lot behind the fishing camp with a bunch of local kids. Being the budding football star I never was, I decided to try to play running back and was actually successful bulling my way through the opposing boys on the other team, for awhile. On a play I would learn to regret, I was picked up and thrown down on my shoulder and suffered a broken collar bone.

I say regret primarily because my Dad was not amused about having to interrupt his vacation to take me to a hospital for treatment. At the hospital, I had X-rays taken and was diagnosed with a broken collar bone. I was seen by a doctor and had my shoulder bandaged up in a sling and was told it would heal on it's own. Leaving only a tell tale bump which showed it had ever happened. Then the doctor said, since I would not be wearing any prom gowns in my future, it would not matter anyway.

I thought at the time, wait a minute! What if I wanted to wear one of the beautiful gowns I had seen on women in my future. What then. I think that comment hurt worse than the actual breaking of the bone. Plus, when I did go to proms and was stuck in an ugly tuxedo, I always looked at the girls around me for any tell-tale bumps to show a collar bone break. I never did see any. 

Along the way, I had several other instances of my feminine aura shining through. I have/had a nephew who from an early age developed a very unsavory attitude towards life which sometimes carried over to me. It started with my politics clashing with his right wing bigotry and going from there. On several occasions, he secretly complimented me by saying I threw a football like a girl. He even said one time when I bought my new Porsche Boxster, I had bought a girls car. Like I said, he was trying to hurt me but was secretly making me feel good. I could not wait to be the attractive blond woman in a sharp sports car.

There were other times when I was called feminine when I was doing my best to be a macho man. Several times at work, I was called "Ma'am" out of the clear blue sky in the middle of a normal conversation with a customer. Looking back, I think it was my feminine aura slipping through my male fence. 

Even though it took me years to realize my dream of living as a transgender woman was much more than living as a part-time cross dresser, I realized there were several tell-tale signs along the way. Maybe the doctor was trying to tell me someday I would want to actually wear a beautiful prom dress which showed off my collar bone break bump. Or my evil nephew would go on to having his own insecurities to deal with. I have not seen him for over a decade, so I don't know or care. He would probably just say he was right about calling me a girl. 

It turned out there were many people who saw through my disguise and at the least knew I wasn't who I was desperately trying to be. A stable, non toxic, productive man. I failed miserably and all I ever wanted was to be the one wearing the beautiful prom gown.   

Calling me a woman was the ultimate compliment. 

Feeling the Pain

 

Image from Eugenia 
Maximova 
on UnSplash.

Learning on the fly all I needed to know concerning my authentic life as a transgender woman often resulted in pain.

The pain, early on mainly materialized when I rushed the process of going out in public as a novice transgender woman or cross dresser. Many times I was reduced to tears following being stared at or even laughed at when I was simply out walking around. I felt the pain for years until I finally realized I was the problem and sought out the reasons why. The main reason was (as I always mention) my male ego was dictating my femininized fashion sense. He was thinking attempting to dress sexy would somehow validate myself as a woman. Of course, it didn't and just made me look ridiculous. On the other hand, when I dressed to blend in with other women, they validated me as a woman.

My frustration and pain increased until I became fed up with the entire process and changed it. My thrift shopping adventures began to change to reflect my new fashion sense. I was held back in many ways by my budget and knowledge of what fashion I was trying to buy. Sizing was an example, as I struggled to find what looked best on my testosterone poisoned body. I did not have the benefit of having any feminine characteristics to begin my journey so trial and lots of error is what I went through. Every time I learned a fashion choice I made  just would not work, I felt the pain return again.

My situation improved when my overall confidence improved to a point where I was able to use the women's changing rooms. When I could afford to go to a mall clothing store, I always checked with a clerk first to see if I was to be accepted so as not to feel the sting and embarrassment later. In the thrift stores I went to, the changing  rooms were not monitored anyhow, so I never had to ask. As I said, when I had the opportunity to try on clothes ahead of time, my improvement rate went way up and my fashion pain way down.

After conquering most of my fashion pain, next up came my paranoia over communicating as a transgender woman in the world. Of course I quickly discovered I had no idea of how women communicate between themselves. I found myself on several different levels when I dealt with the world. Once I figured out I was not "fooling" anyone else and just resorted to being myself, my life improved. One level of woman just did not care and basically ignored me while another level was curious and wondered what I was doing in their world. Overall, I was learning on the fly and had my share of pain such as the one transphobic woman I encountered at a party Liz and I attended many years ago. She was actively harassing me about what my dead name was. She was so evil, the experience still causes me pain to this day.

Overall though, when I compare my transgender journey to others I read about, I suppose I have had it lucky. Even though I had suffered a lifetime's worth of pain when I lost my wife, several close friends and my business in a span of five years, I was able to find new friends and rebound. Mainly because the friends and Liz accepted me as my authentic feminine self. I guess karma was paying me back for a lifetime of wondering what I was doing about my transgender self. All the years of doubting my gender existence came back to be a strength when I quit being a victim in my own life. 

Sure I was transgender but suddenly it became a strength not a weakness and the pain was behind me. 

     

Transgender Inspiration

The late Lynn Conway.

 In my formative years growing from a beginning cross dresser into a novice transgender woman, there were very few inspirations for me to follow. One of the few I knew about was the very accomplished and talented Lynn Conway, a computer scientist and electrical engineer.  

Deep down I knew I was not on the same level as Conway and the very few I did know about followed the same path as most transsexuals face when they transition into a feminine life. We were expected to leave our past behind, have all the needed operations and relocate ourselves to start over. Since I was my usual stubborn self, I could not see me going down all of the same roads as well known transsexuals. In fact, I knew a couple trans women nearby who were ready to go down the surgical road and change their lives forever. 

As in most cases each of their lives were totally different than mine. So they were more of an interest to me than an inspiration. By getting to know them closer, I had hoped to gain more knowledge of what I would face if I decided to go further with my own gender transition. I did learn, as I went on, everything was different when I was living as a transgender woman. I had my own preconceived ideas of how it would be to live as a woman from all the years I had spent closely observing the women around me. However I found most of my conceptions were wrong as I slipped behind the gender curtain. The prime example was how I was presenting myself as a woman. I wasn't dressing to blend in and was drawing unneeded attention to myself. My efforts came from my old male ego dictating my fashion and wardrobe. I had no inspiration to guide me the correct way.

I think I tried to use my second wife as inspiration but I was just not in the proper mental space to accept her criticism. In other words, my feminine self had not had the chance to grow up past my adolescent years as a trans woman. During those years, happiness was looking very lonely as my wife and I constantly fought over my appearance among other things. I think she knew she was fighting a losing battle as my internal feminine self fought with her all the time. Every now and then, I did talk her in to going out to eat as two girls and I really tried to dress down for the date. As a matter of fact, if I dressed down any more, I might as well just have gone as my male self. 

I was getting nowhere fast in my quest to learn more about being a quality transgender woman, so I was forced out on my own. Which added in it's own set of problems. Primarily, here I was sneaking around behind my wife's back to see if I could live as a woman. In doing so, I found I could create another life. Furthering the divide between my wife and I.

The divide widened until her death and inspiration or not, I continued on with my search for my feminine self. What I discovered was, she was with me all along. Just waiting for a chance to live. When she did, she became my own inspiration and I never looked back. In many ways I found she adopted many of the mannerisms and personality of my Mom, who was very outspoken and not shy. I admired her so much, I took her first name as my middle name when I legally changed my gender markers. 

These days, with all the internet and social media access transgender inspiration is much easier to come by and we need the inspiration with all the negative coming our way from politicians. We have to do all we can to keep the positives coming.

I Am I Said

 

Archive Image, JJ Hart

One of my favorite Neil Diamond's songs is "I Am I Said". I particularly was drawn to the line saying I was lost between two shores. Neil was referring to New York and Los Angeles and I adapted it for me to signify being lost somewhere between being male and female.

The song's lyrics go on to say "I am, I said to no one there " I again felt the same way because I had no one to discuss my gender issues with other than the occasional therapist who went quickly through my life with little or no benefits until I reached a point much later in my life. In addition, the pressure to conform to the successful male life I was leading was intense. One of the few positives of my job was I was named a managerial training manager so I was able to take medium ranged business trips from my home in Ohio (yes I am from the much maligned Springfield) and travel by car to Lexington, Kentucky. Usually, I was asked once every six months to make the trip which I quickly saw as an opportunity to pack a few of my feminine items and cross dress. 

I usually worked it out with my second wife I was taking a second night at the company headquarters so I would not have to drive back at night. When I did, I was able to either cross dress and head out to one of the Lexington gay bars. It turned out, there were several back in those days, since the University of Kentucky is there. When I went out, at the least I didn't have to tell the chair or mirror I was actually someone feminine. On one occasion, I hit the jackpot and my training seminar just happened to coincide with Halloween. I thought ahead and when I packed away from my wife's prying eyes, I added a few slutty outfits to put together a Halloween "costume." The difference this Halloween was I was going to try my luck at going to a big straight club and not a gay venue. After a few wrong turns, I found the place and gathered my courage to go inside. Here I was dressed in an all black mini-dress with black heels, hose and blond wig doing my best to ignore all the guys pinching my behind as I walked across the dance floor, Since I needed to be up and fresh early the following morning, I needed to be back early to go to bed.

All along, I was learning what I was and was finding out the hard way what could happen if I dressed the wrong way. One night, I decided to stop at the halfway point on the way home which was Cincinnati. I got a hotel room and proceeded to seek out one of the more infamous gay bars in town for hookups, I thought since my black outfit worked so well before, I would try it again. This time, a very drunk guy at the bar tried to pick me up...until his wife showed up. I was embarrassed and was trying my best to back pedal from the whole situation when he made things worse by telling her why did she not have legs like mine. By this time, I headed for the restroom to hide and when I came out they were gone. As was the black outfit.

Through it all, all the lying I was doing to my wife was wrecking my moral code and when I asked who I was, I did not know. Which made the Diamond song so important to me. 

Finally, I did climb out of the pit I was in and was able to learn who I was but sadly was never able to reconcile my transgender life with my wife before she passed away. All along she was urging me to find myself and by the time I did, it was too late. I was no longer stuck between two gender shores. I had found myself and she was feminine. 

It Was Never Easy

I am amused when anyone thinks my gender journey has ever been an easy one. 

To begin with, I was born into a very male dominated family. Being the oldest son of two, I had heavy male expectations forced on me. Very early on, I learned I was in the wrong place at the wrong time. I did not belong in the male world at all. The problem was coming to the knowledge I did not belong as I was sneaking around my family's back to cross dress as a girl. As I remember, I had two hiding places for my small collection of feminine wardrobe and makeup. 

The first place was up in the attic of our family garage and the second was more creative when I discovered a hallowed out tree trunk in a woods next door to my house. What I did was use plastic trash bags to protect my precious belongings from the elements and it provided an extra way I could be alone and dress which relieved (for a day or two) my gender tension. So none of my drastic measures were easy but I survived without anyone detecting my secret, to my knowledge. 

As years went by and my life as a girl began to be more complex, I was pressured to do more and more to protect my life. Sneaking around became more intense as my wardrobe increased, along with my knowledge of the makeup arts. In all fairness to me, I attempted to ease my gender pain, I told my first and second wives ahead of our marriage I was a transvestite or cross dresser which I thought would help my world. My idea worked for awhile, until I essentially out grew the idea I simply wanted to wear women's clothes and makeup. More and more I wanted to be a woman.

Making the jump from cross dresser to transgender woman often was brutal. Partially because I still had my male life to contend with. It probably would have been easier on me if I was not involved in such a male intensive job which automatically would completely throw me totally and publicly back into a world I never wanted. Ironically, my life as a man I worked so hard to build was now in direct competition with a feminized life I was growing into. 

At the same time, my biggest challenge became was deciding if I was transgender at all, Could I continue a life where I lived in both binary genders temporarily or would I need to choose between being a man or a woman. I ran from the decision for years before I grew so tired of running I could go no farther. Making a decision was never an easy one but one I needed to make. Finally, one night I had yet another soul searching discussion with myself and decided to live a life as a transgender woman. The world as I knew it was showing me the way. For the first time in my life I was single and did not have to worry about a spouse to deal with when I changed.

I went even further and decided to go to a doctor to see if I was healthy enough to begin gender affirming hormones. I was and my body took to them very rapidly, making my decision to give away what was left of my male wardrobe to charity and add to my feminine wardrobe. It was not easy to make the decision but it was easy to live with the results. I only knew my new feminine life would never be easy but still would so much better than the life I had lived,

It was never an easy life and my gender dysphoria certainly did not make it any easier. Waking up in the morning after dreaming if I was a boy or a girl never got my day started on a good foot. All of it became some sort of a daily routine I never wanted. With all the highs and lows, somehow I learned to live with it all. 

Affirmation

 

Recently I had a very important reminder of my initial affirmation as a legal female in the world.

It came several years ago when I decided to have as many legal documents as I could changed to reflect my authentic feminine self. One of the major documents I needed changed was my Ohio driver's license. I made sure I acquired all the name change documents plus a letter from my therapist to insure I did not have any problems. The process was scary but exciting because among other things, I needed the picture ID of the license so I could vote. 

It just so happened my license was due to expire just ahead of the all-important election coming up in November so it was important for me not to procrastinate until the last minute so I can cast my vote against tRumpt. 

In many ways, being able to renew my license symbolically was similar to renewing my gender vows with myself. As far as completing the process, it was easy this time because I was already in the system as female and no one questioned me. Probably the most difficult part was having my picture taken because of all the insecurities I feel when it comes to my appearance. For the morning I chose one of my most feminine tops, applied a foundation, eye makeup, lipstick, blush and tied back my hair and was ready to go. I arrived early and only had to wait approximately fifteen minutes before being waited on. 

Even though I knew the process would be nearly painless, for some reason I was still suffering from needless paranoia. I was able to put it all behind me and reaffirm  myself as a legal transgender feminine person. 

Next stop is my upcoming mammogram appointment which is in the process of being scheduled now. I consider mammograms as a slightly unpleasant rite of passage I need to go through since my maternal grandmother died from breast cancer years ago.

Affirmation is good.