Are We Having Fun Yet?

 

Image from Katie Treadway
on UnSplash.

Having fun as a transgender woman or transgender man can be difficult to define. First, let’s define fun as something that provides mirth and amusement. Which comes from “Dictionary.com.”

In my case, I cannot remember finding much “mirth and amusement” when I was cross dressing as much as I could to present as an attractive girl. All I can remember was that I was experiencing deep satisfaction when I thought I had succeeded. As I began to search for a better term, I went back to the “Dictionary.Com” to look up the definition of happy. Because happy is how I felt when I thought I had succeeded into transforming myself into a pretty girl. I was right when the definition of happy was “delighted, pleased or glad” when something was accomplished. It fit me totally because it worked in all aspects of what I was trying to do. Actually, it was all three of the delighted, pleased or glad definitions which fit me exactly.

The problem I was having was getting to the point where I could be happy about trying to cross the gender border. I severely struggled to find the fine line where I could disguise my broad shoulders and narrow hips of my testosterone poisoned body. I certainly was not happy or having any fun when I was brutally laughed at by the way I was trying to present myself as a woman in the world. As I always point out, back then teenaged girls were the biggest test I faced when I went to the malls and they seemed to be attracted to me like magnets, for all the wrong reasons. It took me a while to realize I was trying to dress like teenagers, which brought me completely undo attention. There was no way I could be happy.

What I also did not understand was that fun or being happy was a fleeting thing for me. Sort of what had you have done for me recently, type of thinking which I was very used to from how I was raised. For the most part, I was never allowed to be happy, so I did not miss it at all. I also say for the most part because slowly I began to discover I could feel happy when I was cross-dressing as a man into my true feminine self. When I was able to find the proper clothes, shoes and wigs which helped me with my appearance with my makeup, I could relax and enjoy a new world I had only dreamed of.  Fun became to me when I could escape the male world, I was forced to spend so much time in and explore all the new facets of being a confident transfeminine person. It made me happy to discover who I really was destined to be in life.

As I headed past the fun and happy part of discovering myself as a transgender woman, I needed to mention the satisfaction I felt when I had reached the point where my diet had kicked in and I could buy more stylish clothes in my own size for the first time ever in my life. I was ecstatic in my pre-hormonal HRT days when a cross-dresser friend of mine purged his feminine belongings and gifted me a set of silicone breast forms that I needed to run out and size just the right bra for.

Those were the early days of my explorations in Columbus, Ohio when I could attend very diverse by invitation only parties where I could see everyone from lesbians to transgender women considering gender realignment surgeries so I could have a idea of how I might want to live my life in the future. Almost every party I went to was to be a fun learning experience, and I could not wait for the next one. At the same time, I was thinking if I was having this much fun, how could it be wrong to have it.

The only negative I experienced was the night I was cornered in a narrow hallway by a huge admirer of crossdressers and almost learned the hard way about what ciswomen learn at an early age. To not put yourself in compromising positions with men which could possibly overpower you and get yourself into deep trouble. I was lucky that my wife came along to bail me out of the situation I unknowingly put myself into.  It was no fun hearing her, I told you so’s all the way home. Mainly because she did not approve of what I was wearing.

As my life progressed towards the ultimate goal of leading a fulltime life as a transgender woman, unfortunately, my wife stood right in my way of progressing.  Which meant I needed to cheat on her with another woman which was me. Every time I slipped out of the house in my heels, jeans or boots, I normally had a good time as I was finally having fun as a trans woman and did not want to ever give it up,  I had gone too far to ever look back to an old male life I never had a choice on living to start with. Like it or not, my life had put me on a collision course of having to decide what I was going to do about my marriage. The course was disrupted when my wife unexpectedly passed away from a massive heart attack leaving me tragically alone after twenty-five years of marriage.

Most certainly, those days of my life were no fun, and not filled with happiness. On the other hand, they were filled with uncertainty and loneliness until I could find my way home again. Thanks in no small part to my inner feminine self who took over my life and others such as my daughter and future wife Liz. Who helped to pull me from my major pity party. When that happened, life became fun again as I was able to lead a life in the feminine world I always wanted to be part of.

 

 

                               

 

 

Graduation Season

 

Image from Logan Isbell
on UnSplash.

It is graduation season around me, and it brought up all sorts of memories of my own graduations. Many far from the usual school graduations everyone thinks about when we think about moving on with life. Plus, it goes much further than just thinking about the pretty new fashions women get to wear on their celebration days. If they choose to do it.

When I look all the way back to my high school graduation days, I always tie it with the prom season which was very close to it. My senior year was actually my second prom, but nothing really changed. I was still very envious of my date’s beautiful prom dress and corsage (which I had to buy her) to add insult to injury. No matter how hard I tried, I wanted the high heeled shoe to be on my foot and not hers and I would be taken out for the evening. Graduation was not as bad as prom because every graduate had to wear the same black gowns, hiding their new fashions until they went to an after-graduation party. But, even so, I still had misgivings about what I was facing following my graduation. As I faced hurdles such as surviving college and the military service which sometime made my gender issues pale in comparison.

Even though I realized a college graduation was in my future too, I did not think of all the other times I would have to graduate in life to survive. Examples included the times in the Army when I needed to graduate basic training all the way to making my way through the “Defense Information School” in Indianapolis. Time was flying by as I transitioned from the college world to the Army and back again three years later when I pursued my second college degree. Aside from brief moments of regression and purging, my desire to be a transfeminine person never went away and was in fact getting stronger. Little did I know I was facing more graduations confined only to how I viewed myself as a person.

Backtracking a bit and going back to my very first time I saw myself in girl’s clothes and makeup in front of a mirror. I realized I had graduated from being a so called “normal” boy forever. Plus, there would be several future gender graduations when I transitioned from being a cross-dresser to a transgender woman and when I began to take HRT or gender affirming hormones under a doctor’s care and took another major step towards my dream of being a fulltime trans woman.

By the time I had gone through all these graduations, even I would have thought I would have grown tired of the process. But I did not. I started to crave the next step in my occupation and my life as a transgender woman. Which put me on a collision course for my future. It came down to which one I would save after the major gender collision in my life. Following years and years of success, one would just have to go. Just trying to look ahead up my winding gender path became a major problem as increasingly carving out a life as a novice transfeminine person on my own terms became a priority over every thing else, I loved in my life.

At this point, my graduations began to slow down and became smaller in nature. Every time I was successful at trying to be the person I always wanted to be, I celebrated my own mini gender victory and resolved to do better on my path. No longer did I have to be envious of the ciswomen around me, since I was allowed to be behind the gender curtain. Which was another graduation for me, as I loved it. It was a major reward for all the work I put into filling out my gender workbook. As a matter of fact, it was the best graduation I had ever had in my life.  If I wanted to, I could wear the pretty dress all the other women around me were wearing.

Until then, I think I was taking all the graduations and transitions I was taking for granted. I was not raised to think anything I did was good enough, so being pleased with my progress towards my dream and being happy about it was a first for me. Ironically, I even was able to use the same restroom in the dinner club I took my second prom date to years later when it became a gay venue. It was as close as I could ever come to reliving the inadequacies I felt so long ago as I looked at myself in the women’s restroom mirror.

Humans are blessed to be able to graduate to many different levels as they transition through life. It is sad because of whatever reason, some people (men and women) are never socialized to make it to a point when they can claim the status of being a man or a woman. They are doomed to never making it past the stage of being male or female and never took the opportunity to graduate to the next level of life. They are the ones who are jealous of and hate transgender women and transgender men for reasons they do not even understand. Often, they are stuck in the past and never have the chance to escape.

If you are busy trying to figure out your next stop on your gender journey, I hope you can take the next careful step and graduate to the level you want to be. In the end, graduation is much more than having a framed certificate for your wall and who would consider having a framed certificate saying you made it to your own form of womanhood above your desk anyhow. Wouldn’t that be something?

Your destination should be your own sense of satisfaction or even happiness because you undertook one of the most difficult journeys a human can take. Congratulations!

 

 

 

 

 

 

                                       

 

Trans Girl on the High Gender Board

 

Image from Navy Medicine
on UnSplash.

I remember completely when I was a kid, intensely afraid of heights, and my mom made me jump off the high diving board at the swimming pool we were at. It was the last thing I wanted to do, and I still don’t know till this day how she convinced me to do it. But she did. I am sure she thought that once I did it, I could do it again, which I never did.

Perhaps, by this time, you are thinking what does this have to do with being transgender but of course I can connect the lines as always. Fast forward to the days when I was first gathering all the courage, I could muster to leave the house and attempt to explore the world as a woman. To do it, I needed to jump off that high diving board again and again. Plus, I would have to raise the diving board even higher every time I tried it.

As I did, I discovered little pockets of cross-dressing acceptance I could exist in. Such as the women’s clothing stores where almost everyone was nice to me. It took me awhile to realize the clerks who waited on me were not being nice just because I was another woman, they were being nice because I had money to spend. To them, my gender was not trans, it was green. Even though I took acceptance and built on it to other potentially mellow venues in malls such as bookstores and coffee shops. I was successful in them and was able to build my confidence from there and move up to a higher diving board and jump off. No matter how scared I was, I needed to force myself to climb and jump.

The next comfort zone I forced my way out of was by forcing myself to stop for lunch to see if I would be accepted. For the most part I was, because again, my money was green and I smiled and tipped well. The magic ingredients it turned out to be accepted into a challenging new feminine world. Or so I thought until I kept on climbing. It turned out the climbing part was the easiest. Once I arrived where I thought I wanted to be. I added “thought” in because once I made it to a higher board, the jumping part really scared me. Mainly because I was leaving so much behind me, along with all the male privileges I had worked so hard to gain. Such as fighting back when someone made fun of me for the way I looked. When it happened, the only recourse I had was to go back to my cross-dressing drawing board and try to determine what I was doing wrong.

Before long, my drawing board became quite littered with fashion mistakes I had made. Going through my cross-dressing adolescence was quite painful because I was a thirty-year-old male trying to do it before I learned otherwise. I was exhausting myself climbing up the high dive and then down when I discovered there was no water in the pool. Finally, I learned the hard way to cross-dress to blend with the other ciswomen around me because they ran the pool I wanted admission to.

It turned out that the pool was much farther down than I thought it was, and I had too much time to think about what I was trying to do before I hit the water. I had not made the time to build up the feminine muscle memory I would need to allow me admission to the world as a transgender woman. It did me no good at all if I vaguely looked like a woman if I could not move or communicate like a transfeminine person.

At that point, jumping off the high board became very real to me. I was rapidly coming to the point of decision about what I would do with my life. By this time, I was in my fifties and was beginning to carve out a respectable life as a trans woman. My new world knew what I was and did not care. About my present, or more importantly, my past as a man. I was able to bring what baggage I wanted from my male life without any interference. It made all the difference in the world to me when I needed support from wherever I could get it in the worst way.

As I lost my fear of the high dive, I began to consider other transgender alternatives such as taking advantage of therapy and HRT through the Veteran’s Administration health care system which I was already a part of. I wondered then what my mom would have thought (she had long since passed away), about teaching me to take the long and difficult path to the high board would come back to help me so much later in life. Especially when she was the one who was dead set about me coming out to her after the Army when I tried. Karma came back to help me when I needed it the most. I could jump off the highest diving board I could just to prove I could.

Of course, the final high board I jumped off was the one which saw me do away with all my male clothes and live life as a fulltime transgender woman. In reality, I was never a stylish swimmer or diver, but at least I made it to the point where I could make it in a woman’s world. A world which would prove to be much more complex and difficult for me to succeed in than I ever thought possible. Probably, because, for the most part (except for a few friends) I was filling out my gender workbook as I went along. Preparing myself for when I could achieve the ultimate goal, my lifetime dreams of living as a woman to the best of my ability.

At the least, I was happy I gathered enough courage to go ever higher on my gender diving board and more importantly jump.

 

 

 

Living in the Real World

 

Image from Jacqueline Mungala
on UnSplash.

Living in the real world became a challenge to me as I transitioned from a male existence to a feminine world. The main problem I had was figuring out what was right and what was wrong as I followed my path through many blind curves and stop signs.

One thing I never thought of completely was how different my life would be if I had ever had the chance to live as a fulltime transgender woman. Sure, I was not totally naïve and thought my world would basically involve pretty clothes and being chased by boys. When I finally was allowed behind the gender curtain, I discovered how complex and layered lives ciswomen really live. Very quickly, trying to live in the real world as a novice struggling trans woman got me in over my head. I would be remiss if I did not bring up how I tried to present myself. I thought trying to look like a sexy teen girl was the way to go, and fortunately my time in that cross-dressing phase of my life went away quickly. Often with brutal consequences of being laughed out of any venue I was trying to visit.

In other words, I put what my male self was telling me about presenting as a woman in the real world behind me and started to look around to what I needed to do to blend in with the other ciswomen around me. The challenge was not only did I have to be as good as the next woman, I needed to be better to survive in the real world I found myself in. With success, I brought confidence I could do more.

The next problem I faced was what was I going to do about my deteriorating (already fragile) mental health. As luck would have it, I was assigned a qualified therapist within the Veterans Administration who knew what she was doing and was able to separate my Bi-polar disorder from my gender dysphoria issues. She provided me with permission to begin HRT which is something I had always wanted and made the real world more livable for a transfeminine person like me.

At the same time, I was trying to take every spare moment away from work to explore different venues as a trans woman. I was attempting to accomplish trying out (as much as possible) everything I would have to go through if I ever followed my dream into womanhood. What was a ciswoman’s life really like and how was it different than what I had already lived as a man. I was entering the scariest yet most exciting time of my life as for the most part I was successful when I went out. The biggest issue which eluded me, was being able to communicate effectively with the world of women I encountered. Learning all the nuances of non-verbal communication women use was the biggest challenge for me. For the first time in my life, I needed to really listen to what was being said to me and watch the other woman’s eyes at the same time to see if I could catch a clue of what she really meant.

Through this portion of my life, I had a powerful motivation to succeed as a woman in the real world. My second wife of twenty-five years had unexpectedly passed away to leave me completely alone with my gender issues. I had no spouse to worry about how to tell my truth about wanting to be a woman. Yet another terrifying yet exciting time of my life. What was I going to do about my newfound freedom. Since you are reading this post, you know what I decided to do. I started making plans to finally make the leap off the gender cliff I had thought of for some time and throw caution to the wind for the remainder of my life. I figured why not because my confidence was at an all-time high with my small circle of friends I had built up. Along with factoring in all the time and effort I put in exploring the real-world ciswomen live in because for once, I had earned my way (or forced my way) behind the so called “sacred” gender curtain.

Once I had made it to this point, after another stop sign on my transgender path, I found I still had more learning to do to really be ready to live in the real world. That is where my ciswomen (lesbian) friends came in which is a subject of another blog post. I will say, they taught me how to be validated as myself in the real world. It was another main transition to go from thinking I was a transgender woman to knowing I was just me. Which took me from cross-dresser to trans woman, back to a secure me during my lifetime. A long, often brutal journey which had a happy ending. I learned the person I had been running from much of my life was not such a bad person after all.

Maybe, most importantly, I discovered the one aspect of my life I never thought I could experience and that was having the ability to be happy. I never had a chance to learn it from my family, and I spent so much time trying to deny myself any satisfaction I could have had from a successful career as a man, there was no time to ever be happy. It turned out that when I turned the corner back to just being the true me, I allowed happiness to be part of my existence.

I had survived all the lessons I had learned as I followed my path to a brighter, more authentic gender future. Living in the real world was not such a bad thing after all. My only regret is that it took me so long (all the way till sixty) to have the courage to face my truth so I could live as I truly was.

 

 

 

The Ultimate Confirmation

 

Image from George Pagan III 
on UnSplash.

My ultimate confirmation in life came when I arrived at a point when I knew without a doubt, I needed to live out the remainder of my life as a transgender woman.

My journey took me to the age of sixty when I finally put my male clothes away and live my dream. Along the way of writing the blog, I have received many interesting comments. Many concerning why I took so long and equating my time as a very serious cross dresser as somehow meaning I was never actually transgender at all. The best all time comment I received was, I was just another old guy on hormones. The comment came so long ago, I do not even remember how I responded.

I can make many excuses as to why it took me so long to transition completely such as I had a wife, I dearly loved who was against it, and a job I worked years to get which paid me well. While those are the given reasons, my ultimate confirmation came from the fact, I just did not have the confidence in myself to do it. For years, I was still being laughed at any time I went out in the world as my femininized self. Before I became very serious about my presentation and lost nearly fifty pounds off my masculine frame and began to take better care of my skin so I could wear less makeup. At that point, the laughter stopped, and I began to acquire the all-important confidence I needed to live my new transgender womanhood. 

Without confidence, I had nothing and little by little, I began to acquire it by doing trips into the world which took me away from the easy malls and clothing stores I was accepted in for my money, to the restaurants which presented me with whole new challenges to overcome such as having to communicate with servers and bartenders one on one. I even went as far as to stop going to the gay bars I thought were safe and going back to the big sports bars I was used to going to as a man. At that point, my ultimate confirmation was establishing myself as a regular at a couple of key venues where I was even given restroom privileges. Obviously, my confidence skyrocketed to a point where it never had been before. I could not wait to do more and more. 

Even with my newfound confidence, a fulltime life as a transgender woman eluded me. There still were huge life questions such as what would I do to support myself, all the way to how I would tell my friends and family. It was about this time in my life when destiny stepped in and answered nearly all my problems. In the space of a couple tragic years, my wife passed away, along with nearly all of my close friends. Leaving me all alone to guide my life in any direction I wanted to. The direction it took me was straight to gender affirming hormones which the Veterans Administration health care system was just starting to prescribe. Since I already was a VA health member, I went through the approval steps and was approved for the HRT program. 

My male self was stubborn about letting to but even he could not fight the ultimate confirmation he was facing. He should have never been in my life to start with and once he got there and established himself, he was difficult to remove. 

Happlily Ever After?

 

Image from Dave 
Goudreau on
UnSplash. 

When it comes to transgender women and trans men, is there ever a happy ending?

As we examine our lives , again and again, we inevitably encounter many pains as we make the transition from one gender to another. Most of us (including me) go through a period of time when we consider ourselves to be cross dressers or transvestites. We were in our own state of limbo, not knowing where we were going. I am amazed when anyone in the outside world thinks our life was so much easier and we were wearing the clothes of the opposite sex as some sort of a lark.

The fact remains, amidst the brief moments of gender euphoria in front of the mirror, we never actually had a choice when it came to our gender issues. In the case of many people such as me, my journey was very lonely and singular and I wondered if I could ever live happily ever after as a transgender woman. It seemed like the impossible dream and if I could ever arrive there, perhaps I could finally become happy. But happiness for me had always been fleeting. Probably because I had never seen much of happy in my family growing up. We were taught anything we did was never good enough. It carried over into my life as a novice transgender woman. 

No matter how attractive I thought I was, there always had to be more. I needed to be better as a trans woman. It turned out I did need to be better to survive in a new feminine world but getting there was a challenge when I went too far, too fast in the wrong direction. Primarily when I went over board in how I was dressing myself way too slutty and attracting the wrong attention to myself. It wasn't the type of validation I was seeking. It took me awhile to realize I could not make it to any semblance of happiness on the path I was on. 

I learned I never would have a chance to be happy in transgender womanhood, unless I began to change my ways and began to dress to blend in with the world. Once I did, I learned I had a whole new set of challenges I needed to face to be happy. Similar to many of you, I faced spousal issues as well as job, family and friends. I always considered changing my gender was a difficult task to take but I never knew all the nuances of making the change I would have to take. Being a woman, trans or not, was a very layered process and I would ever be happy if and when I ever arrived at my goal of living fulltime as my authentic self. 

Then there were the gender affirming hormones I decided to pursue. Before I could begin the meds, I needed permission from a doctor and a therapist to begin. Adding to the importance of the move but once I started the hormones, I knew I was in the right place and I would not turn back to my old unwanted male life.

Even with the HRT, happiness was still fleeting as I faced a wonderful new world. Most likely because there were still instances of public setbacks I still had to negotiate, which included times when my mind was playing gender tricks on me. I was still influenced by sixty years of living a male life and being conditioned to never be happy.

Now, at the age o seventy five, I know I certainly have fewer years ahead than behind me. Now I have to make a concerted effort to be happy. If I don't, it will be too late.

Gender Shape Shifter

 

Witches Ball Halloween
Image,

For years I obsessed with  the idea I basically was  just a shape shifter between my male and female selves. 

All of this coincided with the time I spent as a very serious cross dresser. Basically, all if my idle thoughts were grounded in my feminine appearance. Time I wished I could get back. As my feminized presentation became better, the more I felt more than just a shape shifter. Especially when I began to explore the world as a transgender woman.

My gender ideas were changing primarily because I quit thinking I was fooling the world and began to know I was living as my authentic self. So if the other person was a transphobe and did not like me, it was their problem, not mine. My mind had made a difficult yet important shift when I began to believe in myself. 

At the same time, ironically, my shape shifting became easier. I became more comfortable in the world and at the same time more confident. I found confidence to be my main feminine accessory. Much more so than my favorite jewelry, heels or wigs. Looking another in the eye was much more important when I used the women's room and other places I needed to communicate. Without confidence, I might as well just stayed home and watched television with my miserable male self. I was not shape shifting any longer, I was me.

When I did, I found I was so much happier and I wanted to push the feminine envelope I was living farther and farther. It was all good, until all of my actions put me on a collision course with my second wife who never approved of any ideas of me transitioning any more into a transgender world. I had put myself firmly between the rock and the hard place when it came to my gender issues. To attempt to survive, I did the best I could to live out my dual life I was living. I would over achieve in my work world as a man, then at the same time try to explore the world as a woman.

The more in-depth I became living a dual life as an accomplished shape shifter, the more pressure I felt to do something about it. In the meantime, I was doing things such as shopping for my wife's Christmas gifts as a woman. When I was successful, I was encouraged to do more and more as I suddenly began to feel secure in the world. 

Finally, I came to the point when I cross dressed as a man, I felt foreign as if I was shape shifting again and wanted no part of it. Happily, by that time I was able to try gender affirming hormones which femininized me even further. I enjoyed the effects so much, it was an easy decision for me to never go back to my male world. Being free of gender shape shifting was quite the enlightening experience.