Why Now? A Transgender Dilemma

Image from Karla Herandez on 
UnSplash

Every once in a while I see a transgender sister in my age bracket being hassled for starting to transition later in life. 

Since I didn't begin a very serious gender transition until I was in my early sixties, I feel their pain when someone mentions they aren't trans enough. For some reason, the person applying the pressure to be transgender enough doesn't realize why the transitioning person felt the need to wait before seriously going down their gender path. There are many reasons. Primarily, life gets in the way. Examples are many and simple such as families which come along as well as friends and employment. 

I was guilty of considering all of those as I put off finally transitioning. Plus, it was true on occasion, I did enjoy the benefits of attaining a certain level of success in my largely unwanted male world. By male standards I was bringing home a better than average income while I became fairly proficient at managing larger groups of people in stressful situations. I was able to use my spendable income to treat myself and my second wife to dining out as well as attending large select sporting events we both liked. Even though I was treading water as a male, nearly always something was always missing. I wondered how everything I did would feel if I did it as a woman. 

Another point I need to make in why I waited so long to finally complete my gender transition was along the way, I was experimenting with how I was doing as a woman. I attempt to explain away the years I was trying to see if I could make it as a transgender woman as the years I was a very serious cross dresser or transvestite. During my fifty year journey to my gender truth, I could say also the world caught up with me. When I started and for years after, there was no internet or social media to connect others to me with similar gender pursuits. From there I learned nearly anything could be possible if I worked hard enough to do it. I just had to figure it out.

Perhaps along the way, I was a slow learner as I refused to look my truths in the face and see feminine. Gender dysphoria was a huge problem too. Some days I did see feminine when I looked in the mirror and some days male. Which in many ways continues to this day. I was furthered confused by the public I dealt with in those days who referred to me in the feminine sense when they weren't even thinking. What was I to make of that? What I did make of that was they were seeing past my male exterior into who I truly was. 

The simplest answer to all the doubters of my "trans-ness" is get over yourself. Without a doubt I have been a transgender woman my entire life. My dilemma was trying to learn how to express it. 

   

New Wardrobe Items

 Since the weather is cooperating and the summer season seems to be upon us, I finally decided it was now or never when it came to ordering me some new summer fashion items. 

Of course after ordering from one site which specializes in bright colored "hippie style" clothing, I was flooded with offers from similar vendors.  The problem being I am not really sold on ordering clothing on line. My wife Liz does it all the time and is a big fan so I decided to give it a try. 

My biggest paranoia came from deciding what size to purchase from which site. Fortunately the sites I ordered from had in depth sizing charts and I was able to read reviews on how true the sizes ran. Most everybody wrote in good reviews on the sizing. 

Another problem I had before purchasing was deciding if I wanted to use any of my money during these times to do it at all. You see, I am on a fixed income with Social Security and with the government default problems coming up quickly, they are talking about SS payments being suspended until the spending problem is supposedly solved. I threw caution to the wind and decided to order the items plus one more which I will not show here. 

Unlike many other Social Security recipients, I am lucky to have Liz's regular income as a back up, so until and even if the government gets their act together I should be all right.  

In the meantime, I can replace several long overdue items in my summer wardrobe before the weather totally turns to it's normal hot and humid Ohio summer.

Changing my wardrobe for the seasons has always been one of my favorite pursuits when I entered the feminine world full time. No more old drab boring male fashions for me. Now also, I can go back to my formative years as a frustrated hippie when I was in the Army. With my long flowing hair I was never allowed to have, I can come as close as I can to reliving that time in my life. It is also a plus some of the fashions are returning in popularity. 

I just hope everything fits correctly when it arrives.

Climbing the Transgender Mountain

 

Photo from the 
Jessie Hart Collection

As time has gone by, I have began to think of my transgender journey as being some sort of a mountain climb.

Problems occurred along the way as I became greedy. I found the more I accomplished along my path, the more I wanted.  Many times I was guilty of trying to push the envelope too far and suffered negative responses from the public when I did. Those were the days of not knowing who I was cross dressing for and not having the skill to attempt to blend in with my feminine appearance. I was trying to dress sexy for the men in the world and failing miserably.  Climbing the mountain in those days was very painful and slow. However, destiny was playing a part in my climb because mixed in with the failures were just enough successes to encourage me to keep moving towards my impossible dream of living a life fulltime as a trans woman. I equate it to reaching a certain summit then looking around and deciding you can never go back.

Those were the days when I finally decided I was so much more than a casual cross dresser and when I was successful in my public presentation as a woman, I felt so natural. The best example I can remember is the night I went out on my own to get a drink at an upscale pub/tavern as a woman...not as someone pretending to be one. A huge difference to me at the time. The whole evening worked out so well for me, somehow I just knew I could never go back to my male lifestyle as I knew it at the time. The entire process was terrifying and exciting at the same time. After all the years of trying, I had reached a lower peak of my climb. A place where I could see clearly where I had come from and could see vaguely where I might have the chance to go. If I continued to climb upward.

Even though I am extremely fearful of heights I did continue my upward climb. Fighting me along the way was my increasing fear of totally giving up the male life I so desperately fought to keep over the years. I was just getting to the "Sir" stage of my life when privileges came from just surviving as long as I did as a white male. Even so, my feminine soul was calling me to move ever upward to my dream. 

As I often mention, my second wife of twenty five years was dead set against living with another woman. Especially if the other woman was me. When she unexpectedly passed away at the age of fifty, the  door was open for me to climb another peak in my gender transition and begin hormone replacement therapy or HRT. At that point, I couldn't or wouldn't turn back as miraculous changes began to go through my male body. In no time at all, I made the jump from macho male to androgynous person to looking feminine with softer skin, breasts and hair. I can equate the entire process to climbing my own personal Mt. Everest. 

Once I did scale my tallest gender mountain, I found the view to be breathtaking and at that point I was happy I made the climb. More importantly, I never wanted to go back.