Tennis Anyone?

Image Courtesy Renith R
on UnSplash

 Years ago I felt the need to attempt to copy many of the most popular feminine mannerisms and/or activities I could find. This is a fun post describing one of those activities I was able to indirectly join in on. 

At the restaurant I was managing at the time during lunch we had several women come in for a late lunch and a cocktail (or two). During the warmer times of the year they were avid tennis fans and came in with their very sexy short tennis outfits. Of course, at the time, I wanted my own tennis outfit and be able to go out and show off my legs. 

What happened was, by total accident, I was able to piece together a passable (I thought) tennis outfit with everything in white excluding a tennis racket I didn't have or want. Since I had never really tried to play tennis at all. What happened was I found an all white, lite weight mini dress as a starter point. With it I was able to find all white tennis shoes which were very inexpensive in my size as well as a tunic of sorts (all white) to cover my arms which had tons of black hair I couldn't shave off back in those days because on certain days I needed to wear short sleeves for the kitchen work I had to do.  Hairy arms would not just work with the image I wanted to portray.  I even had to rely on trying to camouflage my hairy legs by wearing two pairs of panty hose as well as adding my own guilty pleasure, a pair of white thigh high stockings.  Because during this time I had agreed with my wife not to shave my legs during the summer. 

Of course, once I had my outfit together, I needed to find a venue to test it out. I finally decided on a nearby mall where I could test my new tennis look with my shoulder length blond wig. Once I got dressed and put my makeup on, naturally the mirror told me I was ready to go and I snuck out the back door while my wife was at work. When I was in the car and out of my hometown,  I began to breathe and enjoy the air on my legs and the drive to a faux tennis match. 

In no time I arrived at the mall, my anxiety over being "discovered" or even laughed at grew stronger as I wondered how I would be accepted. Little did I know during the time I was at the mall, it was nearly deserted. So I was stuck with "presenting" my new tennis look to a few old men who were there to walk around and get some exercise. Naturally, I was noticed and I tried to make it seem I was just in a hurry to pick something up and get back to my tennis. All in all the strategy seemed to work because outside of being stared at (as any woman would) nothing out of the ordinary happened. In no time at all I was back in my car heading home, loving my tennis experience.

These days with all the advanced conditioning available to athletic women, many appear to have developed more muscles with an resultant androgynous look, so a tennis outfit may not be as much fun. One way or another back then, I was able to check the whole experience off my bucket list of womanly things to do as a transgender woman. 

I Failed my Gender Assignment

Vintage Edition of
Transvestia Magazine

 My initial gender assignment was very simple. I was born a boy, now be one. The problem quickly became I was failing the assignment and I just didn't want to be the gender which was assigned to me. 

Instead of following all of the basic rules I was given about being male, sooner more than later I began to realize something was wrong and essentially I had no choice but to follow the rules. As they were presented to me. My parents were members of the "greatest generation" who survived a great economic depression and a world war.  They were well versed in taking what was presented to them and making the best of it. The same was expected from me. I had no way out when it came to my gender issues. I was alone with my problems. 

In response I did the best I could. I participated in sports and did my best to present myself as a so called "normal" boy. While I was doing it, I also was doing my best to use my limited funds to accumulate a small collection of makeup and feminine clothes which freed me up from helping myself to my Mom's belongings. Of course at the time I was outgrowing my Mom in all the size categories, so it was good to finally go out on my own when I could. I guess you could say, this was the first time I actually passed my gender assignment, in my chosen dream world of being feminine. 

At the same time, I learned the male so called attributes of being emotionally distant and keeping my feelings bottled up. I would carry those with me until I was able to more completely transition my gender.  I was able to not fail this part of my gender exam. In many ways, in order to receive a pass or fail grade in either gender, I needed to wait for the world to catch up to me. Since I was a part of the pre-internet generation, information of any kind was very limited. In fact, I was completely isolated in my closet until I learned of "Virginia Prince" and her "Transvestia" publication. I was so relieved when I found I wasn't alone in the world and there were other so called transvestites in the world and some even met for mixers in cities close enough for me to attend. 

Once I did attend, my path to a different gender assignment became clearer. I was able to interact with others dealing with the same gender issues I was dealing with  and come up with a new plan for my life. It was about this time the transgender word became popular and I strongly believed it fit me. It was becoming increasingly evident I needed to take another gender exam. I was failing my initial male assignment and wanted so badly to attempt taking the new exciting feminine assignment or exam. Before I was able to, it turned out I had a lot more studying to do. Being a woman was a lot more than just looking like one. I can compare the process to higher education. Just being able to blend and mix in with the public as a transgender woman was similar to having an undergraduate degree. Then being able to communicate with other women one on one was the equivalent to obtaining a masters degree and so on.

Finally I accepted the fact I had failed my male assignment completely. No matter how hard I tried to succeed as a man, the whole process seemed to be an empty pursuit. Even though I was relatively successful in obtaining male privilege, I found I didn't want it. On the other hand, attempting to go as far as I could with a feminine gender assignment proved to be the answer to all my gender issues. Why? Primarily because the whole process felt so natural to me.

   

A Need or a Want

 

Image Courtesy Alexis Fauvet
on UnSplash

Beware, this post deals with semantics. Perhaps I should have put a "TW" or trigger warning in first. Semantics are difficult to deal with due to tendencies to paint problems or solutions with a broad stroke of a brush.

What I am getting to, is the question of being transgender  more of a need or a want. I have a tendency to think it is a need more than a want. Why? Because to me a want is more of a choice which anti transgender bigots who are trying to take our rights away often try to condemn us with. Down deep we transgender women and trans men know we never had a choice. Our lives were always destined to go down an often long and bumpy gender path to freedom. In other words, destiny equaled more of a need than a want.

As I look at the process, I can compare it also to the need to eat. Naturally we all have to eat to survive and that is exactly how I feel about my gender journey. The more I progressed down the path, the more I needed to keep going. Long ago in my journey did I stop thinking I was cross dressing simply because I wanted to. I learned the hard way I was so much more than a man who had an extra "hobby" which wasn't golf. Instead I was obsessed with the latest women's fashions and imagining how I would look in them. More and more, even though my wife knew I was a transvestite, I snuck away in our marriage. Essentially I was cheating on her with another woman who happened to be me. I always tried to live an honest life so lying to the one person I loved the most tore me up.

Through all the cheating I was doing, I never gave much thought to what was going on. Most certainly the whole gender process I was in was more of a need than a want. I needed to keep pursuing a feminine lifestyle which I had seen other transgender women around me try to do and were successful at doing. Watching and learning from them helped me to live a new life which was slowly but surely taking over my old unwanted male existence. No matter how I tried to tell myself I didn't want to be a fulltime woman and even with all the purges I went through, I kept coming back to the same place. I needed to live a feminine lifestyle.   

The rest of the story I write about often. My second wife tragically passed away from a major heart attack, leaving me so alone in the world. I was able to fall back to the other woman in my life who I needed also. My feminine strong soul took over and with the key help of several dear friends, I was able to undertake my key transition into a lifestyle I had only dreamed of. From there I never looked back. Secure in the fact my gender desires were more of a need than a want.

What I Intended to Be

Image from Jen Theodore
on UnSplash

Early on in my life, I was all in on pretending to be someone I thought I was not. (a girl) I was reinforced by all the lonely times I spent in front of an admiring mirror which was telling me I looked wonderful as a girl. All along, the mirror was just reinforcing what I was pretending to be. Feminine (or what I perceived it to be) dominated my free time thinking.  I wrote "what I perceived femininity to be" because as life went by and I acquired more experience cross dressing and/or being a transvestite. I was so protected back in those days, I didn't even have the time or access to really consider what either term meant. In either case, I discovered both were just labels anyhow.

The whole gender process I went through ended up taking me nearly a half a century to go through which sounds intimidating. The trip also was very laden with various ups and downs which I revisit frequently. I do it in the hope others who are considering such a venture can learn from my successes or failures. Similar to everything else in life, we have to learn from our failures and move on until we can finally experience the successes. I experienced more failures than successes before I finally  learned to present as well as I could as a woman in public. When I did, I needed to settle on one look and build my new self from it. 

From there I was able to move away from any thinking I was moving away from pretending and moving increasingly towards a life to be lived as it was intended to be. The main reason was the process felt so natural. Even though for the most part I was terrified to give up my old male life. Each step I took as a novice transgender woman proved I was on the right gender path. On the path I was able to carve out my own safe places to go to. I started out in gay venues. In which I quickly rejected for several reasons. The main one was I did not want to be mistaken for or treated as a drag queen. From that point I started to go to a few upscale bar/tavern venues similar to what I was used to managing in my restaurant days. I had one main positive going for me in that I knew the venues were primary revenue driven. And, if I did not cause any trouble and tipped well, I could survive if I did the best I could to dress to blend. I became a regular bar fly and was able to build from there. 

Again, the more I quit pretending to be a woman and started to believe I was one...transgender or not, the better I did. The new world I was in provided me many challenges to move forward into a feminine world I had only dreamed of. The whole process led me to quit pretending all together I was ever a male in the world and onward into a dream world of being a woman on my own terms. Sure I faced the haters who said I could never be a woman because I could never bear children to which I replied what about the cis women who for whatever reason can't have children either. For the most part, I never heard from them again.

As it turned out, life started all over for me once I made it to my early sixties and I was able to start all over and live my life as it was always intended to do.  

It's Complicated

 

Photo from the 
Jessie Hart Collection

Often I wonder why I chose such a difficult path in life. It all would have been so much easier if I had only followed the male journey which was set out for me. In other words, if I had been content to be the square peg fitting into the square hole would I have been happier.  Here I was stuck in a white world in a middle class family with all the expectations laid on me of a first born son. 

The problem was, for some unknown reason to me, I never had a choice. From the earliest age forward I always suffered from gender dysphoria. I just couldn't shake the fact I wanted so badly to be feminine. How much easier life would have been if I had accepted the male role I was thrown into without the uncertainty I faced if I had the courage to accept my true gender and build a new life. Compounding the problem was nothing changed when I became older, in fact things just became worse. The more I explored when I snuck out of my dark gender closet, the more I wanted to explore. The world just felt so much more natural when I was living as my feminine or transgender self. The more I explored and had to return to my increasingly unwanted male world, the more frustrated with life I became. Why was this happening to me.

What did happen was, when the pressure built to the point I couldn't handle it, I escaped to my secret feminine world which embraced me. The more I was embraced, of course the more I did not want to go back. The whole process caused me to dwell on the next time I could run to and escape the male world as a woman. When I was in what I call the "hell" times, I became mean and nasty and very difficult to live with. It became so bad, I even lost a job one time when I was being nasty to my crew. I often wish I had the time back when I was obsessing about being a woman as I was trying desperately to go forth and be a man.  How much farther could I have gone?

Again and again I am humored when I read someone who says all along I had a choice to be transgender and live with all the hell I lived with as I followed my path. I was driven hard to be a successful man as a father and a provider and gave it all up when I transitioned. The whole process was unbelievably complicated and stressful. Perhaps the worst part was I didn't completely understand what I was going through. The only thing which was obvious, come hell or high water, I needed to go through it. All I know is when I gave up all my hard earned male privileges to live a full time life as a transgender woman, I did the right thing. The ripping and tearing of my two genders fighting for supremacy just destroyed whatever life I was still trying to live. 

What I didn't understand was how complicated life would be as a transgender woman. I needed to look the part first, then learn all the nuances of a gender which is certainly the most complex of the two binary genders. Male and female. Just communicating with other women as an equal took me a long time to learn. Plus playing in a world built around passive aggression left me scarred on many occasions before I began to understand exactly where the claws were coming from. It was complicated but I was able to learn as it didn't take long for my long hidden female self to gain total control. 

It was my favorite time of my life. As I love to put it, I gained my right to play in the girls' sandbox. 

Transgender Bruising

Photo from
the Jessie Hart
Collection

As we all have experienced, the path we have chosen for ourselves to find and live as our authentic selves is often filled with walls, curves and potholes. Once we think we have conquered one obstacle, another pops up to bruise us. 

Even after all these decades, I still carry the mental bruises when I didn't pass and was stared at or even laughed at in public. Worse yet were the times I was told to leave a venue after a group of guys insisted on playing "Dude Looks Like a Lady" time after time on the juke box. Following my refusal to leave after all of that, I was asked to by a manager. Ironically, I had my revenge not long after that when a group of employees found me in a nearby venue and asked me to return. Telling me the manager who asked me to leave was fired for drug use. Even still, it took awhile for my gender bruising to go away. 

Little did I know I was at a new point in my life as a novice transgender woman when I was just getting started. Only one aspect of my life remained the same and that was change. I had always been a person by nature to push the boundaries and I still did as I climbed my gender path out of my closet. Even though I was excited and at the same time terrified when I was exploring the feminine world, I took my bruises and moved on. Not knowing what the next experience would be. Amazingly, I was able to forget the nights I came home in tears and made myself ready to try again. The learning curve would vary from deep bruises all the way to small hits to the ego. 

Through it all, I was for the most part, learning on my own with no one to guide me. It seemed the path I was on had very few street lights or signs to help. During this period of my life, the internet was just getting established and I was in the middle of a twenty five year relationship with my second wife  who disapproved completely when I suggested in any way I was transgender. Two major obstacles I needed to work around if I was ever able to advance up my gender path without sustaining any other major bruising. Somehow I managed to keep moving forward until sadly my wife suddenly passed away and I had choices to make on my future.

On my path ahead I had already seen plenty of signs promoting HRT or hormone replacement therapy. As I considered the huge consequences of such a move, I thought maybe a increased dosage of estradiol in my system would make up for some of the bruising I had experienced in my past. I figured at the least, the hormone therapy would help to feminize my exterior self which was exposed to the public. Plus the process would help me sync up my inner woman with my exterior man. As I went up the gender path this time, at least I had HRT to help me. Plus, while I am on the subject of help, I always need to pause and thank all the women I met on the path after I started hormones. Without all the women I met, the bruising would have continued longer. My path was telling me I still had a long way to go to truly learn and embrace the layered feminine lifestyle I so desperately wanted. 

To make a long story short, my friends embraced me, healed my  gender bruises and helped shorten my pathway to living my dream life...a full time transgender woman. 

Maybe I was fortunate in that all of my bruises were mental. Not psychical like so many women trans or not have to go through. However mental bruises are hard enough to heal.  

  

My Own Worst Enemy

Image Courtesy Hisu Lee
on UnSplash

I don't know exactly why but during my gender transition from a dark and lonely closet, I was my own worst enemy. What I mean is everytime I made a considerable stride towards my goal of learning if I could really live a feminine life, somehow I would make a mistake in my presentation (or something) which would want to make me head back towards my closet. I even purged most all of my women's clothes, wigs and makeup several times. A "purge" is a term used by cross dressers and/or transvestites when they throw out or giveaway all their precious belongings and reassure themselves they would never journey to the woman side of life again.

In my case, I think I was mostly on the positive side when it came to purges. Or, as I remember, I received more gifts from transvestite friends than I threw away. In particular, one time I was gifted with a very nice set of silicone breast forms which I desperately needed. Especially if you remember the time my ill fated attempt at creating breasts from water balloons failed spectacularly in a venue I was a regular in. I just couldn't convince anyone I was pregnant and my water broke when it happened. 

Sadly, the water balloon instance was not the only time I attempted something I knew deep down was not the smartest thing to do.  Another example was when I had this short platinum blond wig which the mirror told me I looked great in but then discovered too late the wig was not long enough to cover my dark hair which showed in the back. Stunts like that, including poor fashion choices, led me to many set backs as time and time again I was my own worst enemy. Perhaps it was my own male self helping to set me up for failure. He in no way wanted me to succeed as a woman. For the longest time I was frustrated with the smallest of examples of how I was struggling to present convincingly as a woman. It seemed that once I conquered the artform of makeup, hair and clothes, I would destroy my feminine image with still walking like a guy or worse yet, talking like one.

Again and again I was my own worse enemy in my MtF gender transition. Even though I never really enjoyed the struggle to live a male life I went through, the privileges I had gained through hard work were difficult to just let go. The whole give and take gender process between the two main binary genders was very stressful to endure and affected my entire mental health at the time. I was attempting to live approximately three days as a woman and three plus as a man as well as still maintain my well paying male job. As I said, it was an exhausting process trying to remember which gender I was attempting to live in on which day and my lifestyle led me to a very serious suicide attempt. Finally I needed to accept my male self was just throwing any sort of obstacle he could just to hang on as long as he could. On the other hand, everytime I was successful in living my dream life as a transgender woman it felt so natural and I did not want to go back to part time living as a man.

Once I did make the final determination to leave what was left of my old male self behind, it felt as if a huge weight had been lifted from my shoulders. My mental health improved along with my life and I could live again. 

A Rare Night Out

Dining Out from the Jessie Hart
Collection.

Last night I talked my wife Liz into going to one  of our favorite Mexican restaurants.  She works hard and is very much a homebody so getting her to go out is rare. On the other hand, I consider getting in motion to go out and eat is one of my rare pleasures. 

The excuse I used last night was since we were already going to be out to vote anyway, I would treat her to dinner so she wouldn't have to cook. Since we always consider voting to be so important, I didn't have much convincing to do to get her to go out and eat. 

First of all, voting went quickly and I always consider the voting process an honor because of two reasons. The first is obvious because these days, with the spread of anti-transgender legislation, it is important to make sure we all get out the vote to combat it.  All means all of us. Even if you are still deep in your closet, you never know when the door will open and you will need the rights you voted for to live a quality life in the world. The second reason I like to vote is, it reminds me of the first real time I had to use my brand new Ohio Driver's License to vote and my license had the magical female (F) on it. I'm sure as long as I live, I will never forget the experience of voting the first time with my new I.D. 

As I said, voting went quickly and I was treated with respect so I felt good about continuing the evening in another venue we know so well.

These days, ordering from a restaurant menu is a little dicey because Liz and I are on a strict sugar and flower free diet. Using s little imagination we were able to order fajita's without the beans, rice or tortilla's and just had salads instead. Since I have tried to follow the diet the best I could, I enjoyed a mini celebration with a beer. Regardless of all of that, no one paid us any extra attention, which back in the day would have been a problem. Even though I very much am able to move through society without many problems these days, I still remember the days which I couldn't. 

Since Liz and I were able to enjoy a rare night out, I am hoping I can convince her to get out more often. She even orders most of our groceries and household items to be delivered. I am hoping the weight she is losing will fuel a new found confidence in her which will allow her to go out more often. Fortunately, she knows my feeling on the subject. I need to public acceptance to help my overall mental health about being a secure transgender woman. 

I am a big believer in success breeds success and soon I will be enjoying more nights out.    

I Never Looked Back

Image courtesy Rainier Ridao'
on UnSplash 

Once I freed myself from the remaining shackles of my male life, I was fortunate in that I never had the opportunity to look back. Rarely did I think I was doing anything wrong and my inner strong feminine self was ecstatic with the whole process she waited so long for. Perhaps the unique situation I was living in the at the time helped. 

First of all, I was just emerging from one of the darkest moments I had ever known in my life. I had just lost my business not so long after I lost my wife and several close friends mostly due to cancer. At the same time I was really becoming involved with the internet where I could check out the possibility of learning of others in similar situations. Especially in the relatively new world of transgender women. I spent hours when I was off work seeking new information on my computer. The more I saw, the more I wondered if I could pursue similar paths towards achieving my dream of living full time as a transgender woman. The whole process provided me with hope for the future.

It was during this period of my life too when I had very few obstacles in my way. Since my wife had passed away, there was no one close to me to stop me from doing serious experimentation with living life as a woman. I set about to refine my appearance and learn as much as I could about the feminine arts of public life. Primary examples included vocal communication and overall attempts to blend in with the at large public. The whole process was equally terrifying and exciting as well as it took my mind off of my overall problems. Now the process seems like a blur as my inner feminine self quickly took over my life. I decided then to undergo hormone replacement therapy which seemed like the best way to continue my MtF gender transition and never look back. 

I write often about how the hormones affected me and how quick the process was. Possibly because of the fact I was older (in my early sixties) and my testosterone was in decline anyhow. At any rate, even under mostly minimum dosages, I was surprised how fast the changes to my body began to appear. Before I knew it, I was reaching a point where I was a very androgynous human being. Again, I was excited and wanted permission from my doctors to do more. 

I did do more and more and never looked back. Primarily because there was no good reason to do so. Because always living a male life was such a struggle for me and living a new feminine life just felt so natural. My inner self was telling me in no uncertain terms I told you so and I loved it. The feelings continued into my everyday life as I found I could be successful in a woman's world. Finally, never looking back became part of my life as I set out to be the best new person I could be.