 |
| Image from Arun Sharma on UnSplash. |
On occasion, I look back at the early days of my cross-dressing past wistfully thinking those days were the innocent ones of my life before everything began to get more complicated.
In those days, all I needed to do was make sure I did not destroy
mom’s pantyhose or stockings and be careful to put back her clothes where I
found them. I guess I was successful because she never said anything to me. Using
her makeup was much easier because she always kept samples in a side drawer in
the bathroom, I could experiment with. At that time, the whole cross-dressing
experience seemed to be an innocent game. Except for my deep paranoia about
getting caught. Even the paranoia led me to being more creative about hiding my
feminine clothes and makeup. What I had of it.
When the reality of serving in the military during the
increasingly deadly Vietnam War slowly but surely made its way into my life,
much of my innocence began to go away. The stark reality of going without my
dresses and makeup for three years of my young life began to set in. After I
passed my draft, medical exams and tests there was nothing I could do about it.
Because I was not prepared to run to Canada to evade serving in the military. During
that time as well as many years after I was honorably discharged from the Army,
I continued to be quite naïve or innocent that all I needed to do to survive as
a transgender woman in the world was to do my best to look really feminine. These
were the days when my second wife and I battled back and forth about how I was
cross dressing as a woman. She always thought my makeup was overdone and I was
too fond of wearing “girly” fashion for her tastes. I tried to tone it down for
the occasions we went out as two women but her expectations of me were so
strict that if I followed her directions, I might as well not bother cross-dressing
at all.
Even though I lost most of the battles with her about my evolving
fashion sense, I won a few wars when she had to ask me for makeup guidance when
we were going out to a fancier setting. Revenge was sweet. For a while, life
was very routine for us as we both had challenging employment when we moved
from our native Ohio to the suburbs of New York City, a real culture shock to
us both. I was disappointed when the more liberal attitude I expected in the
big city never materialized because we had to rent from an elderly Italian man
and his wife who I knew would have never accepted a trans woman in their
apartment. Long story short, my wife loved NYC while I disliked it and started
my habit of rapidly changing jobs and moving to outrun my gender issues. Undoubtedly,
I had entered one of the most exhaustive phases of my life as I tried to
balance my growing transfeminine desires with a wife, a job and a family.
By this time, my growing one on one interactions with the public
were driving what I had left of my innocence away. I began to realize that I
was locked in a life-or-death gender struggle which may be impossible to
ignore. What did I do? I exchanged my exhausting job changing for settling down
in one great job opportunity, and at the same time begin to explore the new and
exciting world of being a trans woman fulltime. For a time, I was fulfilled by
both aspects of my new life until I began to be overwhelmed by the speed both
my job and me being able to carve out a life as a new trans woman was coming together.
I never imagined I would be so successful, and so terrified about what I would
do about them together.
I like to refer to the process I was going through as trying
to piece together a large, complex puzzle of life. On one hand, I had my male
side loving the financial increases he was seeing. Then my female side pushing
back to what was more important. Making money as an unhappy man or living a
softer more fulfilling life as a transgender woman. Almost daily I struggled
with finding the right pieces for my puzzle. All I accomplished was taking all
the satisfaction I was feeling from either side as they battled on.
As I faced the new world I was living in, I was determined
to be less self-destructive but that did not work either as I continued to do
things like go to my restaurant competitors dressed as my authentic trans woman self.
I was not that good, and it did not take long for the gossip to get out about
what I was doing. Sabotaging all that I had worked so hard to achieve in my career
to finally let people know who I really was. I was destroying once and for all
my male past and the innocence was gone. However, with the loss of innocence came
the deep feelings that I had finally made the right choice and everything I had
done in life directly or indirectly had influenced my future. My primary example
is fathering my daughter, who over the years has accepted me and I love very much.
Without being forced into the Army where I met her mother, I would never have
had the experience of my life. I am just fortunate that I was destined to live
as long as I have to have the chance to see the pieces of my puzzle come together
and have a chance to experience one of the most interesting and scary
experiences a human can take. That of course is crossing the gender border from
male to female to live on the other side.
I was never good with puzzles, especially my own, and to
lose my innocence finishing mine was a real treat.
