Tennis Anyone?

Image from Tony Luginsland
on UnSplash.

 Back when I managed a prominent casual dining/bar venue, we had two women who would frequently come to our bar after finishing their round of tennis. 

Of course, I always noticed and was jealous of their short tennis outfits. I immediately put acquiring some sort of a tennis outfit on my cross dressing to do list. Since I had always admired short mini skirts and dresses on women, finding a short mini white dress to wear as the primary part of a tennis outfit was a priority.

As luck would have it, I found the ideal dress at a women's clothing shop in a mall I always went to. Once I had the white dress, I discovered the rest of the outfit would be fairly easy to put together. I ended up finding an inexpensive pair of white tennis shoes and socks to go with the shoes. The only problem I had then was what I was going to do about the hair on my legs. 

Even though my wife knew I shaved my legs on occasion, she was not overjoyed when I shaved. Primarily because she worried, I was up to no good when I shaved my legs, and she was right. On this occasion, I could not wait to show off my legs and new tennis outfit in one of the malls I always went to. Before I went to the mall, as always, I needed to create the time to do it away from my wife's disapproving eyes. I waited until she was working a day shift, and I began the fairly intense process of shaving my face and legs. 

Once I completed the shave and applied my makeup and hair, I was ready to test out my new tennis look outfit on the world. Immediately, I felt the thrill of my shaved legs in the short white dress I was wearing. So out the door I went into the world. As I arrived in the mall, I noticed my supposedly admiring public was primarily made up of retired men in the mall just to walk and admire the view. Since I was the view, I wore a pair of sunglasses so I could watch their reaction to me without being obvious. It worked and I could see them staring at the tall blond in a tennis outfit.

As I saw it, I received all the pleasure from tennis without putting in all the work. Now all I needed to figure out was how to hide my extra women's clothing. On this occasion, I used a little used closet and hid my new treasured outfit among a set of my old male clothes I never wore. 

For a change, my ideas of how to come as close as I could to learning for myself how a woman would feel in a tennis outfit came together. I could show off my legs and have fun doing it. Plus, I could cross another item off my transgender bucket list. Quickly, I was off to another quest. 

Answering the Call

 

Image from Alexey Elfimov on UnSplash.

On occasion I am sorry to say it took me over a half a century to answer my gender call. But thankfully, I finally did take the call and listen to the urgent message. 

Please keep in mind I don't count all the years I attempted to cross dress my gender issues away. As I often write about, all cross dressing did was provide me with a quick fix. After I dressed as a girl, I felt better for a while before the same old tensions of life with gender dysphoria set in. The problem was, deep down I knew I wanted to do so much more than look feminine, I wanted to be feminine. 

One of the few good things which came from my gender struggles was practice made perfect. Even though I knew I was the only one who could see my progress with makeup and clothes, I stuck with trying to improve every time I cross dressed. It was so difficult for me since I only had the mirror to answer to when checking out my progress. The problem was the mirror was so good in telling me everything, but the truth and I tried to keep in mind I might look good, for a boy in drag. Not as an actual girl. In other words, I learned I needed to hold myself to a higher level than other cis women I observed if I was to survive among them. 

The entire process was so difficult for me since I had never been detailed orientated in my life. Just getting by was not going to be the way to go. I was fortunate when I encountered professionals in the makeup world who helped me along. One in particular came following a transvestite-transgender party mixer I attended near Cleveland, Ohio years ago. After the mixer slowed down, the organizers provided several makeup professionals to provide free tips to whoever had the nerve to ask. On that evening, I am happy I put my ego behind me and answered the call for much needed makeup assistance. The catch was I needed to remove all my makeup and wig and let the professional start over. His work and results were amazing, and I even understood all the tips he was trying to tell me. The end result was I was flooded with compliments and my gender euphoria soared to an all-time high. Furthermore, later on that evening, I was even hit on by a guy in a straight venue I went to with other transwomen from the mixer. 

That night, I did not answer the call to stay with the guy who showed interest in me. My reason was, I was in a strange town with a person I did not know, and I did not know if he realized I was transgender. Not a good place to be at two in the morning. On the other hand, I loved it when the other "A-listers" from the mixer were jealous of me for once.

Along the way, I ended up answering enough calls to barely keep myself going. There were plenty of times when I did not know if my mental health could take it, and I could keep going. It was then when I took the all-important call to begin gender affirming hormones and change my life forever. I was sixty by then and knew there would be no turning back. After I did, I learned taking the most important call of my life turned out to be a life survivor for me. I remember the evening when I decided to answer my phone for the last time. All of the sudden the voice told me I was free to live as my authentic self and the relief I felt was tremendous. All my previous misgivings were swept away. 

Gender House of Cards

 

Image from Erick Langfield on Unsplash.

Just when I thought I had my life altogether, the world collapsed on me.

For example, when I thought my makeup and hair was the best, I could do, I would walk or scowl like a linebacker and ruin my entire feminine image. Of course, then, I would have to recount my steps and see what I was doing wrong. It took me years to build a solid foundation to build my gender future on because my base was so weak.

What made matters worse was the fact at the same time, I was beginning to do so much better as a man with my career. It was like I was succeeding despite of myself. Down deep, I attempted to destroy everything I worked so hard to achieve. All the self-destruction really took a toll on me and my mental health. To make matters worse, on my worst days I would attempt to take my gender frustrations out on the people closest to me. I became so bad; I even lost a job over my actions. Perhaps the worst part was, I did not grasp what was happening to me. I kept repeating the same old stop-gap routine of cross dressing once or twice a week, feeling better for a day or two before I would revert back to my old gender frustrations again. Predictably, my frustrations would repeat, and my gender house of cards would come crashing down again. 

Finally, as I began to acquire more confidence in my transgender womanhood, I started to increasingly build a better base and feel better about the major struggles I knew were coming up ahead. Primarily, what was I going to do about my twenty-five-year marriage to a woman I loved and a successful job I would have to leave behind. And all of that just scratched the surface of all the obstacles I would need to face such as what would my sexuality be if I decided to live full-time as a transgender woman. The path ahead, at the least was very murky. 

Since I was a very social person, I needed to figure out how not to be so lonely anymore. I just could not keep going out to be alone. My dilemma was men did not approach me seriously and I did not know how to react if they did. My first date with a man was with a transgender man who afterwards said I was very scared. Which was true. The problem became when the only other path to being social for me came by approaching other cis women. Fortunately, I did not have a problem because more and more of them approached me. For whatever reason. Regardless, when I went out socially, I ended up at the least talking with other women. Just having the chance to practice my feminine communication helped me to build a better gender base to build from. 

From that point, life became easier, and my path became clearer. Increasingly I understood I needed to leave the male life I never really wanted behind and jump the gender border at whatever the cost. I was near the age of sixty and was so tired of living a lie and was to the point if I did not complete my transition, I would never have the chance to live my dream.

By this time, I was able to build a solid gender house of cards, so everything turned out successfully when I made the final move. Perhaps here would be a good time to quote Paula from the UK: "For some of us there is a real need not just dress as a woman, for the world to experience us, and accept us as a woman ~ it is not enough that in our mind we are women, we need to go all the way; and that is why we need to transition. I too remember my wife saying (with no intended irony at all) "It takes balls to be a woman"

Most certainly Paula our wives were right. That is the primary reason it takes a solid foundation to approach transgender womanhood. Thanks for the comment!