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| Image from Christian Lue on UnSplash. |
I had a good question on one of the blogging platforms I write for the other day. The person asked a simple but relevant question about what kind of a man I was before I went down the strenuous male to female femininization I chose for my life.
Here is how I replied: Thanks for the question. In my former
male life, I did the best I could to be successful and hide my true self from
the world. Early on, I played football and worked on cars to essentially build
a wall to keep the teenaged bullies away. From there, I went off to college and
earned my first degree, a bachelor’s in history before I was swept off into the
Army during the Vietnam years.
After the Army which I was honorably discharged from after
three years away from being able to express my feminine self, I ended up jumping
back into my cross-dressing ways and eventually getting married for the first
time and fathering a daughter. Once again, I was doing my best to do the all
the right things to make the world think I was a “normal” male which of course
I always struggled with.
From there, I jumped out of the radio business and into the
tavern venue world when a friend of mine and I bought a small neighborhood bar
where we lived. My dad described it best by saying it had two doors, so the flies
did not have to stop when they went through the bar. He always had away with
words. At any rate, the bar did not make it long, but my ownership of the building
did. Initially I did not want the responsibility of property ownership but was
talked into it by my dad. I think at the time, I did not want the extra
pressure of owning anything I would have to get rid of as extra baggage if I
decided to make the jump from one gender border to another.
I stayed in my male mode and managed to turn the failed bar
into a successful pizzeria until I was drinking too much and lost it too. I was
trying to over medicate myself as I ran from my depression and anxiety issues,
along with the major problem I had which was of course I wanted to be a woman
more than anything else. During this time also, I managed to sneak in another
degree, an associates in business, from a local college to take advantage of my
veterans’ benefits.
By this time, you can see the theme of my life was not a
good one. Anything successful I did, I managed to destroy because of my gender
issues. I even lost our house I bought off the GI bill.
Ironically, my life began to turn around when I met the first
of the two most influential women in my life. The woman I met worked at a radio
station I worked for after I was discharged from the Army and was trying to run
the pizzeria successfully. I was literally swept off my feet and ended up
divorcing my first wife and marrying the second woman. By the way, both women
knew of my cross-dressing desires before we were married. It turned out I was
man enough to stay married to her for twenty-five years before she suddenly
passed away, wrecking my life for several years before I could rebuild it.
During the twenty-five years I went through with my second
wife, I began to really learn I was not the man I used to be as I felt myself
transitioning again from cross-dresser to transgender woman. In the meantime, I
had thrown my old baggage caution to the side and had built a successful career
for myself in the restaurant industry. By the time she passed on, I had built
was too much spousal support, family, friends and jobs to casually risk it all
and transition. Although it was always my dream to do so. Being the man I was
meant I would have to give up the positions I held with civic organizations in
town too. I felt flattered to be a part but at the same time never felt really
at home there.
After I had given up any hope of ever finding anyone else to
be with the rest of my life, I met my future wife Liz, and she was instrumental
in pushing me into pursuing HRT by telling me she had never seen any male in me
to start with. Her gentle push was all I needed to give away all my male
clothes and stop the charade I was living life as a man.
I guess you could say that although I tried hard to be a
successful man, I kept trying to destroy any success I had. It took a series of
good women to show me the way to where I should have been all along, living my
dream of being a transfeminine person fulltime.
My first wife went with the flow and did not seem to care
what I did, my second wife approved of my cross-dressing but totally disapproved
of HRT and any idea I was transgender, and my third wife totally helped me
along. Out of the manhood I never wanted. The only woman left to mention was my
internal one who (not so patiently) had to wait for her turn to do more than
survive as she needed to thrive for a change.
I hope this answers the question of what kind of man I was
before a jumped out of the man’s club and into the girl’s sandbox. I led a
complex life of failure and success as a man but never felt as if I was doing
the right thing. I was fortunate when good people came along to save me from my
self-destructive self. Without them, I doubt if I could have ever made it to the
place, I am today.
Thanks for the question! I appreciate any response I get
from all of you plus any claps and subscriptions you send my way.












