Pause and Reflect

 

Image from UnSplash.

Yesterday, as I waited for the doctor to see me, I had a chance to pause and reflect on my long gender journey so far.

In doing so, I had the opportunity to think about how scared I was in the early days of going to the doctor as well as other things. Naturally, I discovered some other things I was trying in the new world I was in, totally over my head at times. On occasion, I don’t think I point out enough how little I had to work with when I started my male to female gender journey. I was from a very male dominated family so there were no understanding moms or sisters to help me. In addition, my body was very testosterone poisoned which meant I had no effeminate body parts to work with, except my legs which I received several compliments on at various Halloween parties I went to as a woman. While I was flattered by the attention, I rapidly became more paranoid. I began to take compliments on my legs by thinking the people left out the part that I had on my legs as I had good legs as a man dressed as a woman.

As I reflect on those confusing days, I wondered how I had continued to persist as well as I did. I guess the reason was because what I was considering doing felt so natural even though it was so scary to me. I spent hours and hours pausing my life and reflecting on where I wanted to go. Too many hours, to be exact as I needed to be careful, I was missing out on my regular life as a man. Even though I did not worry about losing my male life the way it was. I wanted him to go away, but I needed to make sure I did it right. In doing so, I was selfish. I wanted to keep some of my male privilege and transition at the same time. All I did was hurt myself and those around me in the short and long term.

In the short term, I knew had problems dressing my body as a woman. I had the overweight thick torso and broad shoulders to worry about which would not go away no matter how much I attempted to display my legs. I was doomed to failure by wearing too many short miniskirts. My male ego was working overtime, and it cost me many embarrassing moments in the public’s eye before I finally learned my lesson and learned to blend with the percentage of the world I really needed to deal with, which were the other women. It is like the other women I dealt with at the VA yesterday, I made sure I thanked all of them for being there, and they really appreciated it and treated me better. In the past, I would have been too shy to do such a thing.

As I continued to reflect on my past evolution of my transfeminine person, I remembered again how self-conscious I was on my early visits to the VA clinics I went to for care. I was so afraid of being stared at, all the way to being laughed at. Which I never actually was. It took me several years of progress to overcome where I was in life. It took me the visits I made to the venues I went to when I left the gay bar scene I was involved with and moved on after I was tired of being mistaken for a drag queen. Which I had nothing against, but it just wasn’t me.

At this point, I was wondering exactly what to do. Some I have talked to mentioned the “courage” word with me when I thought of going out in the world. On the other hand, I thought pursuing a transgender life was in many ways, my destiny I had been working on for decades. As I reflected, I thought how right I was. From the mirror to the world, I had carefully followed my path and just had to keep doing it. Or, instead of courage, I would never forgive myself if I had never tried to try out living my dream. Especially when I had proved to myself that I could do it. I had a giant inferiority complex concerning my entire life as a trans woman which I had to conquer.

By this time, my doctor was ready to see me, and I needed to return to the reality of today’s world. At the advanced age of seventy-six, I view each annual exam as very important of course. Even though it was invading my time to pause and reflect.

 

No Way to Solve a Problem

 

Image from Babi on UnSplash.

When I discovered my true gender issues that were disrupting my life, I needed to try to solve the problems they created.

In order to do it, I set out on a lifetime journey of discovery. Like most of you, I began my explorations in my mom’s clothes and even tried my hand with her makeup samples. My mirror often lied to me and told me I presented as a pretty girl. Of course, in my pre-teen years before testosterone began to change me, I had an easier time of looking the best I could as a young girl.

When testosterone came along with puberty my problems became real. At the same time, I was becoming better at hiding my collection of feminine clothes I found and was able to buy from my meager allowance. I became very resourceful when it came to my cross-dressing desires, as I even resorted to a cheap Halloween costume wig to get me by for years until I could finally afford to buy one.

As I chased my feminine tail from one close call to another with my family, I wondered why I was cursed with the gender problems I had. In addition, I felt as if I was the only one who had them. I was trapped in a male dominated family who would never understand a boy who deeply wanted to be a girl. My only choice was to keep trying the best I could to solve my problem.

It took me years to realize my so-called problem was more of an opportunity than anything else. But first of all, I needed to face my problem woman to man. No more of my second wife telling me to be man enough to be a woman. It turned out, I was man enough to be a transgender woman, but it was going to be a real battle. By this time in my life, I had accumulated quite a bit of male privilege I knew I had to lose in order to be successful. Basically, for a while, my female self’s main strengths where she felt so alive and natural when given a chance to shine.

As she took advantage of her time in the public’s eye, almost all of my problems seemed to melt away, and I began to feel having the opportunity to experience both binary genders up close and personal in my life was not a problem at all. I just made it one due to my inability to deal with it. I just had too many gender obstacles to overcome. I had accumulated too much male baggage I doubted I would ever be able to live without. It turned out, I could live without most of them, and surprisingly, I could bring some of the baggage along. My prime example was my lifetime love of sports, which I found a group of cisgender women who were as serious about sports as I was, so I was able to fit right in and even have fun.

The new and improved me proved I had lived most of my life as a man as a lie. All the time I spent worrying about wearing dresses and makeup was a waste of time. I had my whole life backwards. My wife was right; I was not man enough to be a woman for the longest time. Once I was though, I never looked back. I can’t say I was prepared for all the changes I was about to make; I was excited about the opportunity I was given to make them. Which most people never get.

It was certainly never a way to solve a problem; I learned the hard way.

 

Planting the Gender Seeds

 

Image from Sebastian
Demitro on UnSplash.  

After my initial experiments with my mom’s clothes, I blamed the cross dressing and started to plant my gender seeds, as I wanted to be feminine all the time. Sadly, for me, it took me decades to realize the seeds were already planted and were growing. All along, I had an idea that was the case, but I was afraid to do anything about it. Mainly, because I had no one to turn to for understanding. The times were very dark in the 1950’s when I was growing up for any understanding of gender issues at all. As I always mention too, I grew up as the oldest son in a male dominated family, so my goals were set for me as a boy.

It wasn’t until much later in life that I had served my time in the military that I was able to water my gender seeds and watch them grow. My first realization I could come out of my gender closet came in the final months of my time in Germany in the Army when I went to a Halloween party thrown by the nearby hospital staff dressed completely as a woman with shaved legs and all. The biggest moment came weeks later when I admitted to my closest friends, my costume was not a costume at all. I loved to dress as a woman and was a transvestite as we were called back then. In the 1970’s.

The best part was, my friends could care less and more importantly, the higher up’s in the Army never found out and I was honorably discharged after my three years were up on time with no problems. Coming out to my friends really set me up for success in growing more and diverse gender seeds…until my mom came along and tried to kill them. I was emboldened by my recent success in coming out and one night I decided to tell her. She responded the expected way with shock and the added offer of paying for a trip to a psychiatrist. From there, the discussion rapidly ended, never to be brought up again for the rest of her life. I knew deep down I was not crazy and did not need a mental health professional to tell me I was.

With that knowledge, my gender seeds continued to develop, even though they were in the darkness of my closet for the most part. Until I could stand it no longer, the only times I ventured out in public as a novice transgender woman was the occasional Halloween party and business trip I went on. Somehow, I was able to smuggle my feminine wardrobe, wig, and makeup past my wife and enjoy a night out on the town when I arrived there. For the most part, the experiences I went through helped me to nourish my transgender seeds and come away with a better understanding of where I fit into the world as a transfeminine person.

Even though I was becoming more successful in chasing my dream to ever live as a trans woman, I kept finding I had a long way to go. In order to see my seeds finally bloom, I needed to have the cisgender alpha females I encountered to accept me. They closely examined me and let me in to play in the girl’s sandbox. To get there, I needed to tend to my seeds which were still blooming. The mistakes I made all centered around when I was overconfident about where I was headed and I got burnt. Fortunately, I was able to reach down and pick one of my flowers and offer it as a peace offering. The flower was enough to move my life along.

My garden proved to me to be worth all the effort I put into it. All the tears I suffered early on when I went out into the world as a transfeminine person were used to water my seeds and watch them grow. Plus, all the time and effort I put into learning the makeup arts after looking like a clown in drag came back to help me. I took the time also to plant diverse seeds which helped me when I encountered difficult situations. Which I never knew where and when they were coming from.

It turned out that I never had much of a green thumb in my male life, but a flourishing trans thumb when it counted the most. It was quite the discovery for me when I discovered how layered and complex the women’s world I was in. I also benefited from the careful job I did of planting and protecting my young seeds. On occasion, I regret the time it took them to grow, but in many ways, I was the prisoner of when I grew up in the dark days in the pre-internet era. But taking the extra time to become strong and thrive in my new life was worth it. As I said, the seeds were there all along, all I needed to do was nourish them. 

 

 

Gender Immigration

 

L'eggs said it best.

With all the negative publicity being brought to the new immigrants to this country by the orange felon/pedo in Washington, I thought it might be time to connect the dots to my own immigration. A gender one.

My immigration plans began as a vacation. I was tired of the male world I was competing in and taking a break as a cross-dressed girl in makeup was a great way to escape my life. Little did I know, from these humble beginnings, I was starting a lifelong journey which in many ways, I am still on over a half a century later. Had I known, I would have ever attempted to undertake such a radical immigration.

Early on, I was just looking to grab the so-called low hanging fruit of cross dressing. I enjoyed the feel of the clothes, all the way to the thrill of hose on my freshly shaven legs. Then, I slowly began to realize so much else was happening. Increasingly I wanted to be more and more like a girl and started to wonder about pushing my male self out. It was difficult because I came from a highly male dominated family. As I pushed forward, my immigration into the feminine side of life became more intense. I tried my best to acquire new more fashionable clothes and even bought my own makeup and panty hose. Do you remember the “L'eggs” panty hose which came in plastic egg shaped containers which it seemed you could buy everywhere, and is still made today. I learned the hard way; how easy it was to destroy a pair when I unfortunately ran one of the legs. Ruining my outfit.

Progression was slowed by a late-teen collision with serving time in the military due to the Vietnam war. Obviously, I could not bring any of my “stash” of women’s clothes or makeup with me, so I was stuck. No more gender immigration for at least three years of my young life. There were several major positive things which happened for me while I was stuck being a man in the Army. A prime example was all the traveling I was able to do around the world in places such as Thailand and Europe (Germany). The whole process enabled me to keep my mind off my gender issues and set me up with the idea I could outrun my problems. Which, of course, turned out to be impossible. Which should be the topic for another blog post.

After the Army, my life changed again as I entered the world of parenthood. Being a parent of a daughter was an unexpected but pleasant surprise, and my gender immigration was put on hold briefly again. I say briefly, because I discovered my transgender issues ran deeper than I had thought. My presentation as a novice transfeminine person was coming along. My first wife did not care, and I was able to explore my potential future as a gender immigrant at events such as Halloween parties. Each party to me represented a chance to see how I was being accepted as a woman in society.

After a few years, I ended up divorcing my first wife and marrying my second. She also knew about and accepted my cross dressing from the beginning of our relationship but never accepted me being transgender as I immigrated towards being a woman. My male side was like being the Titanic, slowly sinking and then picking up speed with her fighting me all the way. It turned out, the issues I was facing were like the tip of the iceberg. With most of it being hidden from everyone. Including me. She tragically passed away before the final resolution in our relationship was ever decided.

When she moved on to the other side of existence, it was left up to me to decide the future of my immigration. I had certainly paid my dues by taking on all the menial and not so menial work of being a woman. I was on gender affirming hormones and was living as much as I was able as a transgender woman, so I was close to filling out my immigration papers and was ready to go into a world I had only dreamed of. My presentation had improved to the point where I was not the most attractive woman in the room, but I could handle myself to the point where most of the world just did not notice me. So, my immigration was more successful than I ever thought possible.

Perhaps the best part of immigrating was learning to accept and love myself for who I really was. Which meant all the hassles I had over the years as I tested out the world, made my immigration worth it.

 

 

Confidence is your Main Accessory

 

Image from 
Jon Tyson on UnSplash.

Some assume I have reached the point of life I am at, through very few challenges.

The truth is that I faced many challenges along my very long gender journey to living fulltime as a transgender woman. I write about many of them often. As I look back, the one main challenge I faced was having the confidence to move forward to my strong dream. Perhaps the earliest confidence I needed was when I walked down our long driveway dressed as a girl to check the mail. Hoping someone would notice the girl in a miniskirt out of the house on a winter’s day without a coat. Then hoping no one would see me and somehow report me to my parents. Nothing ever happened, so I gained the confidence to keep doing it.

The problem was, there were only so many trips to the mailbox I could take to feel good about my cross-dressed feminine self. Here I was taking all that time and effort to feminize myself and having no outlet except the mirror. I was frustrated in my little closet which I had no idea of how to escape from. I was like a caged animal, I knew I wanted out of the cage, I just didn’t know where to go when I escaped.

As the years passed by, I traded going to the mailbox with a yearly trip to a Halloween party. Even though it took me years to get it right, I finally figured out how to figure out a “costume” which helped me to build my confidence that I could present well enough to get by in the world as a woman. My goal always became to be mistaken for a woman in a costume, not as a man dressed as a woman and I achieved it. From there, my problem became Halloween only happened once a year, and what would I do the rest of the year about my growing gender dysphoria. My final decision was a simple one, if I had the ability to do it. I would have to manufacture my own reasons to sample the world as a novice transgender woman and see if I had the same positive feedback I received on Halloween. I discovered most of the world did not care about how I was dressed, and I gained the confidence to do more.

I made it to the point where I began my “bucket list” of things to do as a transfeminine person. Or could I do other things that women do in their everyday lives and succeed. Every time I did something such as taking myself out to lunch, or negotiating a bookstore and buying a coffee, I checked them off my bucket list and proceeded to move on to more difficult interactions with the public.

Of course, not everything I did was a success. I was told to leave a venue I thought I was a regular in one night when three drunk guys thought it would be fun to play “Dude Looks Like a Lady” on the jukebox over and over again. Initially it hurt me, until I got my confidence back and found another venue right up the street. My success was complete when the crew of the place I was asked to leave found me one night. They told me the manager who told me to leave was fired for drug abuse and they wanted me back. Retribution was mine as well as a real boost to my confidence. It felt good to be wanted as their token transgender woman.

Even so, to this day, I wonder why my confidence is so fragile. In September, my wife Liz and I are taking another bus tour. It’s our fourth one, and this time we are traveling from Ohio to Boston and then up into New England by train. Even though, I have never had any real problems with anyone else on the trip before, in the back of my head I still worry about some right-wing woman questioning my gender and ruining my trip. I am sure I am just paranoid and should be worried about catching Covid again and ending up in another hospital. Which is how our last vacation ended up. Hopefully I can get an updated vaccine just before we go. Which will build that part of my confidence.

The only way I know to build your confidence is to keep being yourself and improving your presentation as a transgender woman or cross dresser if you prefer. Perhaps it will always be fragile like mine is and it is something we always will have to deal with. One thing is for sure; you cannot build it by hiding yourself away. Expect some setbacks and keep moving forward as you are building a new future. It is a huge step forward. Having nice fashion and applying beautiful makeup is wonderful but it all means nothing if you do not have the confidence to pull the picture together. Humans are like sharks and they will know something is wrong if you let them.

 

 

Low Risk...High Reward?

 

Image from Jayson 
Hinrichsen on UnSplash.

There are many things we do in the gender universe which represent a low risk, high reward effort.

For example, under the cross-dresser umbrella, we have the far-ranging participants who go from wearing panties under their male clothes, all the way to those who fully dress as transfeminine women in their spare time. At the least, there is more risk to the cross dresser who is fully dressing in feminine fashion and makeup than the person who simply needs to pull his pants up to cover his panties. At some point too, one must consider if wearing women’s clothes is simply a fetish or is there more to it. Which carries even further into the world of sissies and such which involves men who fantasize about forced femininization.

In my case, even though I deeply felt the pleasure of hose on my shaved legs, or other beginning thrills such as looking at myself in the mirror, deep down I knew there was so much more to what I was doing about my developing gender issues. I knew too, if I was ever caught with my clothes and makeup on, there would be no rewards, just risks, so I needed to be very careful. All the way to the point of never wearing panties under my male pants at school and on rare occasions dreaming about a woman forcing me to cross dress at all. Ironically, I talked a woman into dressing me head to toe as a woman only one time and I ended up thinking I could have done it better myself. The risk of telling her did not equal any reward at all.

The risks and rewards proportionally grew greater together as I grew older and my male life began to grow. Many times, without my feminine one who was still stuck in her mirror. It was in the Army of all places, when I first came out to a small group of friends that I was a transvestite and much more than the fully cross-dressed woman they were able to see at a Halloween party. Naturally, it was a huge risk to take because the Army could have taken measures to discharge me. The reward did come when I was able to finally feel the relief of telling someone else my deepest secret and no one cared.

The further reward of coming out of gender shell was the fact my first wife was in the group of friends I came out to. Our marriage then led to the greatest reward of my life…the birth of my daughter who supports me to this day.

As my male world kept expanding and threatened to take over my transfeminine experience, I was going through a wonderful period of great discoveries in my life. Those were the days when I first discovered the transgender term and what it meant to me. For the first time in my life, I found a community which I belonged in. I was too much woman for the average low risk cross dresser and too little for the risk it all world of the transsexuals who were headed for gender realignment surgery.

I was so comfortable in my new place in the world, I was prepared to take bigger and bigger risks. Much to the chagrin of my second wife who had no problem with my cross dressing but was totally against any thoughts of starting gender affirming hormones and living increasingly as a woman. Every time I went out to explore the new feminine world I was creating, I was risking my twenty-five-year marriage. Because I chose to lie to myself for many years of denying who I really was, I ended up making us both miserable.

My excuse was I knew I would be losing a great marriage, a substantial job and many hard-earned male privileges if I threw all my cards into the middle of the table and came out into the world as the person I was always meant to be. Finally, the choice ceased to be mine as I embraced my new feminine self. My wife had passed away, I reached the point where I could retire from my job, and I was eager to check out the world of female privilege. It was all a huge risk, but I had to take it as I was nearing the age of sixty and I figured I was near a now or never moment in my life.

I had never been a gambler of any sort, but I wished I had the courage to make the move I made earlier. One thing is for certain; you can never rewind your life to make up for past mistakes. You just have to do the best that you can of your past to plan ahead for the future risks you will have to take.

 

 

Why Not Me?

 

Image from Buddha Elemental 3D
on UnSplash. 

My life has been a series of why not me moments.

As a boy growing up in Ohio, I always wanted to be a better athlete, which turned out to be an impossible quest because there always seemed to be a better athlete in my world to take my place. Then there was my attempt to be more social in the world, but I was incredibly shy, and it was so difficult to do. So, I ended up hiding at home, thinking someday I would grow out of my shyness.

My greatest why not me moments came as I struggled with my gender identity. It became so bad with me that when a stranger asked me what I was going to be when I grew up, the only truthful answer I never gave was a woman. I internalized my thoughts and somehow hoped they would go away. Which of course, they never did. They just got worse because the main problem I had was wondering if I could do it at all. Information was incredibly difficult to come by in my sheltered male privileged world and for the most part I was lost, and I continued the path I was on. Doing my best to live a male life successfully, and at the same time, steal away moments of privacy to cross dress in front of the mirror.

Often, much to my surprise, I was semi-successful at both. I kept my increasingly gender fluid life in balance by improving my mirror image away from drag clown to beginning girl, while at the same time, keeping the bullies away from me by having an interest in sports and cars. I even went as far as dating a few girls in high school where I ended up attending both my junior and senior proms. Little did anyone know I wanted to be the one wearing the pretty gown and getting the flowers. As with the rest of my life, I got over it and moved on, no matter how difficult it was. Why not me was not working, I was still stuck in my gender quicksand and there was no handsome cowboy coming to help me out. Or strong woman as it turned out.

When I finally had had enough of being a gender victim, I opened my closet door and looked around for the first time in my life. I knew I needed to move past the once-a-year Halloween parties I was attending as my novice transfeminine self and try more ways to get out into the world to see if I could be successful or would my dream of life as a woman always must be a dream. I was ever so cautious as I began by shopping in malls and bookstores which turned out to be low impact areas for novice cross dressers or transgender women. I went to places where my money was more important than my gender which gave me the confidence to do more. More meant testing the public with new and exciting ideas such as stopping at restaurants to eat to see if I had any push back at all. I did not and moved on. Maybe, my why not me was coming true after all.

Sadly, dreams being dreams are not so easy to achieve I found out. Especially in the world of gender change. There was no way I could gloss over all the nuances of being a true transgender woman would entail. Many times, I ended up getting my new high heels stuck in more quicksand than I could have imagined and was fortunate to have found my way out, which I have written about in several blog posts. It occurred when I suffered the loss of male security privilege. However, by this time, I was able to take the good with the bad which was beginning to lessen, and I could see my dream being reality.  Which I had never thought possible.

For the first time in my life, I was beginning to live my why not me moments. I was at the threshold of living the life I had always wanted. Free from the male shackles which had tied me down. Sure, at times, it was unbelievably confusing to do, but with the help of a few women friends I always mention, I made it and was able to get out of the quicksand all together and rebuild my life.

Today, I am a woman who happened to come from a different background than most. But it was my dream to make it, and I did. As I said, I never thought I could or would.

 

 

 

 

What a Rush!!!

 

Vintage Transvestia Magazine

I encountered a real problem when my cross-dressing urges went from being a real adrenaline rush, all the way down to what I experience now.

I do remember the process did not take so long for me and I should have known then my cross-dressing activities were much more than a harmless innocent hobby I was involved with. If I had the information available to me then which became available later, I would have had an idea I was transgender. Of course, back in those days, the internet had not been invented along with all the social media rooms which came with it. I was in the dark ages of information and was very sure I was alone in the world with my gender desires. I always give credit to “Virginia Prince” and Transvestia Magazine for initially opening my closet door and showing me there were others in the world called transsexuals and transvestites.

During times of depression with my life, I could always fall back to my well-worn issues of Transvestia to lift my spirits. Plus, I discovered groups hosted transvestite mixers in Ohio I could attend with the proper preparation. I was ecstatic! I finally had a chance to meet others like me. Little did I know, I did not get that completely right, but that is another story all together.

In the meantime, I read my brief moments of adrenaline rushes were really called gender euphoria. Regardless of the label, I still had a difficult time controlling mine. Most of my examples come from the time my wife and I moved to the New York City metro area. For some reason, she left me out on my own one night to go to a mixer out on Long Island. Much to my surprise, I had a difficult time being admitted to the mixer by two cisgender women running the door. I asked why I was not being allowed in and they said no real women were allowed and I needed to show them an identification card with a male picture on it to get in. I was shocked and promptly showed them my old male drivers license and had a great time…until the buzz wore off days later. Then, I became mean and difficult to live with because I was feeling sorry for myself because I felt increasingly sure of myself as a transfeminine woman.

About that time, Halloween rolled around again which gave me an excuse to leave my closet and explore the world as a trans woman. This Halloween, I was getting better at “costuming” to present well as a woman and not to thrill as a cross dresser. Again, I was able to be out on my own because my wife was not a fan of Halloween and by pure chance, I ended up in the middle of a group of cisgender women all as tall as I was and dressed about the same way. Again, I had a great time and was even asked to dance by a man who I wondered knew about me.

All I knew was gender euphoria was great, until I crashed and burned. Then I always slipped back into my usual gender dysphoria problems. It seemed I needed the constant reassurance of me being able to present well as a transfeminine woman just to get by. Which was no way to live.

In order to live, I needed to make difficult life changing choices such as exploring the world increasingly as a feminine transgender person. I needed to weigh the difficulty in what I was doing with my life with what would happen if I was discovered. To accomplish my dream, I began to make small mini “bucket lists” of things I needed to do, most to just see if I could and increase my gender euphoria or adrenalin rush. Surprisingly, very quickly again my bucket lists did not provide much euphoria but in their place, a deep sense of stability in my life. For the first time in my life, I even felt I could be happy as a person. Whatever I was doing as a transfeminine woman, I was doing it right. Or so I thought.

Naturally I was afraid to make the final move to sever all ties with my male self. I found myself wasting precious time as I was able to expand my own new world as a woman of my own making. I had successfully gone through transitions from innocent cross dresser, all the way to full time transgender woman with bumps and bruises I had earned along the way. But I learned from them and moved on to a better life. If I only lived once, I wanted to live what was left as a woman.

Sure, my initial doses of adrenaline did help until everyday life came in and rescued me. Now I have smoothed out my life with fewer peaks and valleys of euphoria and when I do experience the negative gender dysphoria, I am able to live with it much better.

 

 

 

Painting a Picture

 

Image from Vinicus Amix
Amano on UnSplash.

During my life, I have never been accused of being an artist. In fact, I would mess up drawing stick figures.

The best thing I could do was connect dots. Which I needed to do quite often in my gender conflicted life. Basically, the main dots I needed to connect were, was I a boy or a girl. It ended up taking me far too long to finally connect those dots and attempt to draw my gender picture.

When I began to experiment with makeup, I learned the basics of facial artwork and even I could make myself look better in the mirror. Mainly, though, I struggled along until I summoned the courage to request a makeover from a professional makeup person at one of the transgender-cross dresser mixers I went to. He did a miracle job and transformed me into a woman who I only had dreamed of. Most importantly, he was able to explain to me what he was doing in a step-by-step format that even I could understand. I looked so good, I was invited along by the “A” listers, as I called them when they went out to explore other venues after the mixer was over. I even got the last laugh over all of them when a man tried to pick me up in a venue we were in, and they were not.

Sadly, the success I felt from the mixer did not last long when I had to go back to the real world, I was a part of. When I did, I became mean and nasty to my wife and others around me. All the way to almost losing jobs because of my attitude. No way to paint a picture. Somehow, I needed to get better before I self-destructed my life.

I hung on until I did get better when I had the chance to leave my closet more than once a year for Halloween parties. I was aided by the fact that my artwork with makeup and clothes continued to improve until I looked better than some sort of a circus clown in drag. I simply had to if I was ever going to have the chance to live my dream. Through it all, it did occur to me how difficult the process was going to be. I was painting two pictures at the same time, one as a transfeminine woman. One as a successful man. The stress of doing so nearly killed me. Being a man was easier because of all the white male privileges I had gained but being a transfeminine woman felt so exciting and natural when I painted her.

By the time I had gotten this far, I found I had painted myself in a corner. I could see the finish line for a change, while at the same time, I had a wife I loved, a family I loved and a good job to protect as a man. Decisions, decisions were wearing me down. Primarily because it was so frustrating to me to have worked so hard throughout my life to paint two pictures, only to have to finally choose between the two. What I did was let the public choose which picture they preferred. Since my transgender woman had an unfair advantage, she won the contest easily. She got to start all over again and learn from all the mistakes her male counterpart made and go from there. Time and time again, the public picked her.

Putting the finishing touches on my feminine portrait proved to be easier said than done. First, I needed to come out of my closet to what was left of my blood family. I received a 50/50 reception when I was accepted by my daughter and rejected by my brother. By this time both of my parents were deceased. Predictably, both coming out events were scary and quickly resolved. My daughter wondered why she was the last to know while my brother did not have the courage to stand up for me to the rest of his extended family. We have not spoken now in over a decade. Sad but true, he never wanted to see my finished portrait. Conversely, my daughter and I are closer than ever.

But then again, are our portraits ever finished until we die. Shouldn’t we always be making small upgrades the best we can? Plus, age should put us in a better position to do it. Sure, painting two completely different gender portraits at the same time was difficult and at times required tons of skill to keep one hidden. But somehow, I was able to gain the artistic skill to make it happen.

The powerful draw of an overwhelming dream was all the motivation I needed to become a better artist and provide the background I needed to live a life as a transgender woman.

The Clash of Gender Ego's

 

Image from Sherest Gupta
on UnSplash. 

Through most of my long life, I needed to deal with the clash of egos, doing battle for my existence.

On one side, I had my well-worn and battle tested male ego who was doing his best to make it in a world where he did not want to be. On the other, I had my deeply hidden feminine side who only made her appearance in front of the mirror and then went back into hiding. In other words, my male ego attempted to dominate while at the same time, my female ego was hiding, just exactly where she did not want to be.

For the longest time, to make matters worse, I did not think women had much of an ego at all. Except maybe with their appearance. As I made my way through life, I discovered how wrong I was. On several levels, As I always warn about, my male ego dictated how I dressed early in my life when I was going out in public. I fell in love with several compliments I received about my legs when I went to Halloween parties and made sure I showed them off to the extreme when I was going out for the first time. The idea was all well and good except I was doing nothing to overcome my broad shoulders and torso. I had no fashion balance, and it showed with the number of times I was made fun of in public. My male ego had failed me. I was dressing to his tastes and was failing.

It took years to do, but my female ego finally took control and slowly but surely, I began to blend in with the other women around me. For a moment, I even thought my clash of egos was over, but I was completely wrong. My male ego was very stubborn and still thought he had some sort of control over my life. He refused to believe he had lost all his male privileges and nearly got us in trouble several times before he learned the hard way what problems could exist.

One of the biggest issues was the idea of my sexuality and how it would or would not change with my new transgender life. Of course, Mr. Macho recoiled at any thought of intimacy with a man, but Ms. Self wasn’t so sure. Like many women, she had a spectrum of ideas about sex which were not so rigid and paranoid. In fact, I made a concerted effort to date a few men to see what (if any) excitement would happen. It just so happened women turned out to be much more interested in me as a trans woman, my choice was easy to make. For once, my male ego won. For the wrong reason.

One of the earliest instances I can remember of a lesbian woman approaching me happened one night at a mixer/party I went to at a friend’s house in Columbus, Ohio. At the mixer, I ended up approaching another woman and having a brief conversation before we decided to leave for a while and go to a big lesbian club to mingle even farther. We ended up having a good time that night, but since I still had a wife to go home to, I could not stay long enough but visiting with another ciswoman who happened to be a lesbian was a wonderful experience and would set the path for my future. Although, I did not know it at the time, primarily because my male and female egos were still clashing.

By now, you may be asking the question, who was winning the struggle? My woman was, even though my male self would win every now and then, it was as if he would take one step forward and two steps back. On the occasions when my second wife would catch me coming back from a night on the town, he would jump forward into purge mode. Vowing to never wear any female clothes ever again. All the time knowing there was no way possible he could ever keep his promise. I had crossed too many lines in my gender sand to go back, and the fact was becoming increasingly evident to him and my wife, there was nothing they could do. They were waiting for me to face my own reality.

Solving my final gender issue was easier said than done. My male self was hanging on for dear life until the very end, and he nearly pulled all of us down in the process until therapy and suicide came into play. Finally, I needed to pick a winner in my gender ego clash, and I was wise and picked the only way I could go. I put my old male self completely aside and begin to live a transfeminine life I had only dreamed of. I wondered why I did not pick the winning side years ago and live my truth.

 

 

What an Adventure!

Image from Phillip Rawstron
on UnSplash

 Admittedly, at the age of seventy-five, I spend a lot of time looking back at my life, attempting to look at all the successes and failures that I went through.

The end result is normally wow! Did I do all of that? I remember the adventures I went through when I first left the house in my short skirt with freshly shaven legs and felt the cool night air on my body. At the time, I felt as if there was no other feeling like it and I could not wait until I could do it again. Then, there were all of the Halloween parties I went to cross dressed as a woman from head to toe. The parties were exciting to say the least but also showed me I could possibly make it in the public's eye as a transgender woman in the near future. It is important to note, I went through the stages of trying to dress sexy as a woman to trying to encourage the others at the party I really was feminine. 

When I started to try to enter the world regularly, I found I had many adventures ahead as I went from being laughed at to my face to at least presenting well enough to blend in with the world at large. Out went the short miniskirts and in came the jeans and tops which other women were wearing on a regular basis to the venues I was going to. At the time, it was less fun for me but at the least, my new fashion choices were saving me the torment of coming home in tears. For the first time in my life, the public was not laughing at me for simply trying to be who I felt I should be. 

From there, the adventure really started for me as I made the second big transition in my life. From part time cross dresser to fulltime transgender woman, if only in my mind. The entire idea was huge in that it took me back to the earliest days of admiring my girl-self in the mirror, and thinking that was good, but there was still something missing. The missing part became evident over the years; I wanted to be the girl I saw in the mirror. Little did I know at that time; my gender path would be a long and intense process. Nearly fifty years to be exact before I was able to come to terms to who I really was as a person. 

Before I was able to build a small number of friends I saw on a regular basis, I was intensely lonely, and on many nights was just going out to be alone. Hoping no one would bother me. Fortunately, they did, and my life took an adventurous turn for the better.  I ended up being invited to lesbian mixers, the women's roller derby and even an NFL Monday Night football game. To say I was scared would be too easy a term. Excited would be another appropriate way to think about what I was going through. Where had all of this been all the time I was stuck in my closet? 

Another big adventure was evident when I discovered I had more than one gender closet to escape. There was the physical closet of fashion, makeup and presentation to overcome, and then the major hurdle of the intense mental closet I lived in. I experienced major problems with overcoming the life my male self-had built for me. He was intense and did not want to let go. By then, it was too late, and I was never going back. 

All my adventures proved to be worthwhile, and I succeeded in living my dream of transgender womanhood. Plus, for those of you who think you have waited too long to live your dream, I waited until I was sixty before I started. 

Transgender Adjustments

 

Image from Markus Winkler
on UnSplash.

No matter how you cut it, life is nothing if not a series of adjustments.

As we enter school and learn to adjust to the other kids around us, we discover the basic differences which go far past the genders. As far as boys go, we learn some are toxic, some are athletic, and others perceive themselves as leaders at an early age. I went to a very small rural school and basically went to class with the same students from kindergarten through the ninth grade. Plenty of time to form cliques such as who were the brains, the hell raisers, the athletes and yes, even the losers. 

The one clique which I never had the chance to join was the one with gender issues, or the boys who wanted to be with the girls. I was very sure I was the only one with such issues, so I needed to make whatever adjustments I needed to make on the down low. No other person could ever learn of the adjustments I truly wanted to make but could not. 

As I made it through my early school years, the complexity of my adjustments to gender increased. I remember going to a high school festival where I saw a male student in drag for the first time in my life and was fascinated. If he could do it, why couldn't I? It was around this time of my life also when I heard the rumors of one of my fellow students who had attended a Halloween party dressed as a girl and was prettier than his sister. All of it gave me a brief glimmer of hope for my future. Perhaps there were other males who wanted to be girls also. Sadly, it was just two instances of learning of an outside world of gender adjustments before "Virginia Prince" and her "Transvestia" Magazine came into my world.

"Transvestia" rocked my world with its articles and pictures of cross dressers or transvestites everywhere. Seemingly, the only acceptance requirement you needed to have been, was to be heterosexual which was no problem for me. Of more importance was the fact the side organization call "Tri-Ess" I believe, held monthly mixers in Ohio within driving distance of where I lived. All I needed to do was fill out an application and be approved to meet others with similar gender adjustments for the first time in my life. 

As I discovered, when I first began to attend the transvestite-cross dresser mixers, how much more adjusting I would need to do. I met so many others of differing backgrounds from basic admirers to ultra feminine transsexuals, my life was changed forever. Sadly, I had plenty of time between mixers to figure out how I was going to adjust to the new world I found myself in. The only realization I came up with was, there were very few at the mixer who were close to me in my desires and adjustments I wanted to make. Plus, I had a spouse to attempt to explain it all to. 

Sometimes, I am not as naive as I let on, and I knew all the action behind closed hotel room doors was not heterosexual in nature but beyond that, nothing I saw really surprised me. Like I said, I came away from the mixers knowing I had many more adjustments in my gender journey which in reality was only beginning. Little did I know, life would take me in so many different directions before I could settle into my transgender womanhood. I would have a daughter to raise, marriages to negotiate and jobs to take on in my life. 

In many ways, I am no different than the rest of the world except I have gender issues to contend with. I don't expect any special treatment but then again, I don't need to be discriminated against either. I was only doing what came natural to me by trying to survive in the only world I knew. 

I Made Nothing

 

Image from Camillo 
Contreras on UnSplash.

Several of my earliest memories of success as a cross dresser came during the Halloween parties I went to. 

When I wore my very short mini dresses, showing off my freshly shaven legs, I found I had several women come up to me and say, I "made" a good-looking woman. Years later, when I began to understand "woman speak" better, what they probably meant was I "made" a good-looking woman, for a man dressed as one. 

Furthermore, I soon came to realize, I was not making anything. I was simply being who I was. In order to learn that simple fact, I needed to live decades of life as a parttime cross dresser or novice transgender woman. Or I needed to live my gender truth before I could claim it. I needed to get out of the mirror and into the world to learn if I really belonged there. Those were the days when no one in the world around me would give me a break. The public was laughing at me (rightfully so) because for the most part, I was dressed like a clown in drag. Plus, my old male self, my second wife and my mirror did not want to let go of me. Making my life miserable and destroying what I had left of my mental health.

Juggling two genders at once was a tremendous challenge when I caught myself practicing living one gender when I should not have been. Being called "Ma'am" at my macho management job was certainly not cool or good but somehow, I survived to live on to the next day when I was determined to do better.  What happened was, I did keep getting better at my feminine side and increasingly began to leave my male side behind, which scared him.

Fear, as they say, is a powerful motivator and instead of giving up, my male side and my second wife grew increasingly close and forced a battle of the wills. In other words, neither one of them wanted to lose their place in the world. Which included my universe. It turns out, I did make something...a huge mental mess for myself. It is one of the excuses I make for taking nearly fifty years to break out of my gender bonds and flourish out of my closet and mirror. I just had to make sure I was making the right choice and there was so much pressure on me. 

As I grew out of the mental gender mess, I had made for myself, I gained the critical confidence I needed to establish myself as a secure transgender woman. Not just a femininized man. Since I had spent a lifetime getting there, the personal coming out was extra special to me. It was as if my feminine self was telling me what took so long. As it turned out, I shared her belief in wondering why I took so much time and wasted so much nervous energy I wish I had back. As we all know, worrying over what we did in the past is a waste of time, unless we are learning from our mistakes.

I felt better when I realized I did not make anything, when it came to my gender issues. Rather, I inherited them from some unknown source which made life a challenge. A challenge I needed to finally accept before the pressure I put on myself had grown too heavy to carry and I had to put it down and go with the life which made me feel natural and alive. When my transgender womanhood became secure thanks to friends I had, I felt so much better as I built a new life.

The Gender Envelope

 

Image from Alexandru
Zdobau on Unsplash.

Sure, I spent or waisted far too many years before I fully transitioned into transgender womanhood.

I was too slow for such a long time actually pushing my personal gender envelope when I was busy telling myself I was no more than part-time cross dresser. I saw no harm in just doing my best to look like a woman until it just wasn't the answer I was looking for. The more I cross dressed and improved my feminine presentation, the more I pushed the envelope and looked for more. Very quickly, my yearly Halloween adventures just were not enough.

I began to wonder if I made a good impression at Halloween, could I make the same impression if and when I tried to go out in public as a novice transgender woman. Following many trials and error experiences, I found I could survive a public which largely did not care about me. The big error I always point out is when I was not receiving any attention to speak of as a woman, I began to dress trashy to attract the wrong sort of attention. I was mistakenly pushing my gender envelope the wrong way. When I finally began to understand the best ways to dress my male body and apply the proper makeup, did I begin to be successful and blend in with other women in the world. 

Once I had accomplished all of the fashion, hair and makeup necessities, I allowed myself to further push my gender envelope. When I did, I found myself needing to understand how women exist in the world. Or how do they communicate with other women and men. I had a quite a bit of catching up to do since I was attempting to catch a moving train heading down the tracks. I did not have the benefit of growing up female with a mother or peer group to guide me. I always point out; the passive aggressive system of interaction most women operate under was the most difficult for me to learn. Since childhood, I was always used to the full-frontal confrontational world men operate in so I was attempting to survive in a whole new world.

Once I did survive, I began to push even harder, ignoring warnings from my wife on what would happen if I was ever caught. I put the male gay bars behind me and moved on to big sports bars and lesbian bars where I could actually be myself. I thought I had reached my peak when a dear friend of mine invited me to a trip to a NFL Monday Night Football game in Cincinnati. Even though I was very scared at the thought of going, I could not turn down a chance to empty my envelope and lay my gender cards on the table. Since I am not really a gambler, I hoped the lifetime of preparation I put into this moment would serve me well. 

The moment did serve me well. As always, I survived and became a better woman for it. Plus, I learned the game was only the beginning. The life in my transgender womanhood I was going to experience, would be extremely fulfilling and everything I thought it could be when I started pushing my gender envelope.

Opening Transgender Doors

 

Image from Sara Darcaj on Unplash.

To me, life is a process when we are born and doors open and when you die, and doors close.

For transgender women and trans men, sometimes the process is more intense. Depending upon where you view yourself in the gender process, we go through a series of doors until we reach our dreams. On a personal note, I think I went through at least three or four transitions before I arrived where I am today. The first realization I had was when I was quite young and understood when I looked in the mirror cross dressed, it was only the beginning. I wanted to do so much more than just look like a girl; I wanted to live her life also. I equated it to the problems I had with my gender roller coaster. When I was able to dress as my feminine self, I was satisfied and happy, for a couple days until I became depressed and moody again. Looking back, I equate the process with knowing I was transgender but back then, the information on being trans just wasn't available.

My second big transition came when I learned I did not have to wait another whole year between Halloweens to test the world as me. I was desperate not to have to wait a whole year before I could learn again the feminine lessons I needed to move on to my next major transition. I refer to it quite a bit as the time I suddenly realized I wasn't a part-time cross dresser at all, I was a much scarier prospect, I was a transgender woman. A term which was just being known and popularized. I say scarier because accepting the fact I was transgender meant I needed to apply a deeper understanding to who I was on another level. Not just reapplying myself to more effective feminine presentations. Along the way, I had reached the point when I could blend in with society as myself, so I had the time and inner energy to move my life forward towards my dream which involved my next transition. 

The important aspect of my next major door to go through was the simple knowledge I could indeed establish a new life on the other side of the gender frontier. Confidence was everything as I decided to knock on the door of gender affirming hormones. I bravely sought out a doctor who would prescribe my minimal dosages of the meds until he could see I had no adverse problems. At that point, it was obvious to me my body had taken to the new hormones in a very unprecedented way. It was as if I should have been on the new treatment all my life. 

In turn, the changes the hormones made were nothing short of amazing. I could and have written entire blog posts on the hormonal subject and what it meant to me. At the least, all the doors I was able to go through in my life, made life much less boring and interesting. Just wondering what would be behind the next door was scary but exciting since changing genders into what you always should have been, made life worthwhile for me. 

Without doors to encounter, my life began to slow, and I had a chance to enjoy my true self thanks to new friends I had made. Along with my desire to see what is behind the next door.

Now What?

 

Image from Kolos Kevie 
on UnSplash

During my long journey to transgender womanhood, I have encountered several "now what" moments. 

The first I can remember came during a Halloween party I was attending. For the party, I was dressed in a very short mini dress which showed off my freshly shaven legs completely. Even though the men mainly stayed away from me, several women took it upon themselves to compliment me on how good my legs looked. Now, I remember vividly telling one of the women thanks but a lot of good my legs will do me. I did not finish the thought by telling her having good legs will not do me much good if I need to wait another year to show them off again at Halloween.

As life flew by, I finally was able to show the public my authentic self, to very mixed reviews. Predictably, I went too far overboard building my wardrobe around my legs which was correct to do during the eighties when short skirts and oversized sweaters and tops were all the fashion vogue along with big hair. It was like the fashion gods were playing right into my hands as a novice transgender woman. 

As we all know, fashion trends change, and I was forced to also if I was to do my best to blend in with the other women around me. Finally, I needed to lengthen my skirts and adopt shorter wigs. I was not happy but had to adopt a new "now what" fashion mode. 

What came along to save me was a new realization about what presenting as my autentic self-meant to me. I began to survive on my new personality as the public began to want to know more about me. When I did, I began to encounter many new "now what" moments on a regular basis. In other words, I was in very deep trying my best to discover if I could or should attempt a gender transition into a new scary, exciting world. 

I discovered I very much did want to be in the new feminine world I was discovering, and I could not under any circumstances turn back to the old male life I was in. "Now what" had passed me by and it was too late. I had passed all my personal tests seeing if I could do it.

It was a long road, but I managed to do it. I just wish I had listened to my inner gender questions years or even decades ago.

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. 

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.