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As I matured as a person and a crossdresser, taking a vacation from my male gender became a reality for me.
It all started when I first felt the inclination to try on
articles of my mom’s clothing and moved on from there. Very soon, I spent as
much time as I could in front of the family’s full-length hallway mirror
imagining myself as one of the pretty girls I envied so much. Before my
unwanted male puberty set in, I did not have so far to go to be on vacation from
my boyhood self. Then the changes set in and I began to develop the body angles
and shape of a man as the girls around me were showing off their new curves in
pretty clothes.
At that point, vacations became harder to earn, as it was
becoming more difficult for me to look like a girl at all and try to work my
way around having no knowledge of makeup at all. That chapter of my transgender
notebook (like all the others) was empty, and I struggled not to look like a
clown in drag at the circus. In a very short time, I became aware that if I was
to ever reach my dream of living my life as a transgender woman, I had a long,
hard struggle ahead.
It did not make matters any easier when I went on family vacations
and saw other girls my age in cars on the highway. One young dark-haired beauty
still stands out as one I remember. As I saw her time and time again when we passed
on the highway, I so wanted to be like her and put my pillow over my head and
pretended to sleep. No imagined vacation for me on the real one. My gender
reality was with me all the time.
One way or another as life went on, I needed to do something
to survive. Somehow, I needed to break through the bonds of the increasingly complex
male life I was living and start to carve out a new transfeminine existence on
my own. If my reality was indeed female, I would have to do something about it.
What I did was begin to mix business with pleasure on my vacation. Business was
when I was learning that ciswomen ran the world I wanted into and pleasure was
when I was able to finally blend in until I was allowed behind the invisible
but so real gender curtain. To maintain
the lifestyle, I was trying to lead, I needed to do a lot of research and
repetition to see if I wanted to be there at all. Those were the nights when I
broke away from all the gay venues I was going to and started to see if I could
be accepted in lesbian and straight places.
The vacations I took into the world as a new transgender
woman turned out to be life changing for me. For once, I did not have to wonder
what if would be like to live in the world as a woman and just do it. My time
away from my old boring male world, took me into a wonderful new life as the
woman I always wanted to be. I was the trans woman at the big sports bar
enjoying my large beer as I watched my sports teams play on the big screen
televisions. Occasionally, I received some pushback from a toxic man, but it
was not enough to deter me from having a good time. Mainly, because of my confidence
in who I was building every time I was successful trying out the me, I always
should have been. I was not building anything new, just allowing my true self
to flourish in the world.
At that point, it occurred to me that my vacations were changing
drastically. Instead of believing I was taking vacations from my male self as a
trans woman, I was now taking time from my feminine world to allow my male self
to finish up important things such as working and keeping up a false image of a
man for the world to see until I could fully complete my male to female
transition. Since I had accumulated so much male baggage over the years, clean up
was not going to be easy. Finally, it occurred to me that transitioning to my
new life was going to be an all or nothing proposition…or was it?
A big decision I needed to make was involving my sexuality which
had never been a question for me in my male life as I had never been physically
attracted to another man ever. It did not help me when I got a suggestion from
ciswomen to buy bananas to get ready for a new sex life that never came. Even
though I had dates with several cismen, nothing ever sparked within me and we
never went anywhere except kissing, Women, on the other hand were different as
I still cherished their company which I found they enjoyed mine too as they
went on vacation with me. Since HRT hormones took away any possibly of
traditional sexual intercourse between me and another woman, by choice I took
it off the table.
It all led me to wonder what I would do about sports, the
one big passion left in my life. Could I still interact with the world as a
passionate sports loving woman or would I have to give it all up. It turned out
that no, I did not have to give up my passion, it just changed direction like
so many other things in my life. For example, when my lesbian friends and I
were talking sports, we did it on an equal footing. But when I talked sports
with a man, often I needed to take a back seat to his sports knowledge even though
I had plenty of my own. I learned my lessons and moved on.
Even though many of my vacations from life were just quick, cheap
escapes, many were extensive, expensive paths to my future life. Plus, they
handed out much needed respites for my often-battered mental health as I battled
depression and anxiety. It all helped me to survive and make it to my dream
goal I never thought I could make it to. A life as a transgender woman.
As always, thanks for not taking a vacation to read and
comment on my posts. Your input always means a lot to me!
