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| Image from Alexander Mass on UnSplash. |
As I made my way into a very serious time in my life on my male to female femininization journey, I found myself on a hill with my male life slowly slip sliding away.
At first, as my male self-started to panic at losing his
footing in the world, my overall life was in panic mode also. That was until I
began to enjoy the process and realized it was nothing more than a normal progression
into a transgender woman’s life, if I truly wanted to go there.
Keep in mind, I was doing my sliding in a pair of new high
heels I was in love with, and for a long time I was on uneven footing. Then, I started
to do everything in my power to determine if the grass was greener on the
feminine side of the gender border for me or not. I even went to the extent of dating
cismen to see if I had any sexual attraction to them at all. For the most part,
finding a date with a quality man was difficult to do as most ciswomen know as
most men were turned off by having anything to do with a trans woman at all.
To go out with me, a man had to be willing to meet me in a
public place where I was already a regular in and go from there and I was stood
up many times. Which I got used to. The only exception was a man I met in a
group of people who had tried and failed to marry an exotic dancer who was beautiful
and in the social group. After the brief marriage which lasted only a week, the
man ended up getting made fun of by others in the group which I thought was
completely unfair because I saw how much he was hurting. After that, on
separate occasions when we happened to see each other at the bar, I tried to
comfort him the best I could. It turned out the big bear of a man who ran a
lumber yard and rode a Harley motorcycle was an interesting person that I liked
and we got along. Sadly, he moved on before we could get to know each other better
and I had a chance to ride on his Harley.
There were dates with other men which helped me slide down
my transgender path, but not many as most men avoided me like a disease since
they sensed I had left their club and were afraid of their frail sexuality
being challenged. But other men were attracted to women like me I discovered as
I was pushed along down my ever-steepening hill to my own feminine destiny. There
were men such as Dan and Bob who were willing to meet my demands of going on a
date at one of my regular straight venues I went to.
At first flipping the gender tables from male to female was
difficult for me and I was extremely nervous but slowly learned what I would
need to know to carry on a successful conversation from the other side of the binary
gender spectrum. I learned quickly not to push too hard to start communicating
and let the man lead the way and do my best to follow from there. I had to be
careful not to be too reticent to talk because I was building myself into a strong
feminine trans woman and did not want to give that up. I was a true contradiction
in terms. I found I did love being treated like a woman but always was worried
about what was coming next. I did not want to be the sort of woman who
seemingly just led men on for sport. I did not have to worry because both men
were gentlemen and we went upon our separate ways after a parting kiss. The
kisses were the first I ever experienced with a man, and I was interested to
see what if anything I felt after doing it. I did not and my sexuality was
never challenged. I did not even go out and buy bananas to practice with as my
ciswoman acquaintance Amy told me I needed to do.
This entire time of my walking my downhill gender path, I
was noticing the biggest surprise of all. As men were ignoring me, women were attracted
to me for any number of reasons. I think the main reason was women were curious
why I wanted to give up being a man to be in their world. Whatever the reason,
I found myself going to lesbian monthly mixers with friends and even being
asked to be one of my friends “wing-person” one night when she was afraid to approach
another woman for her phone number. I was overjoyed to do it and had another of
those once in a lifetime experience when I was accepted for who I really was.
The only problem I was experiencing was a big one. I was
still living parttime in a male world and slipping quickly down a hill into a
female one. I had people to tell and a job to deal with among other problematic
issues I had to take care of before I lost it all and plunged off a gender
cliff into an unknown, I knew nothing about. My cliff was so steep, I could not
see to the bottom.
By this time, proceeding carefully was out of the question. I
had survived the death of my wife as well as most of the few male friends that
I had and I was ready to make a change. Even then I could see which change was
coming and I would have to take the chance to seize the opportunity of a
lifetime to take it. So, I let go of everything that was holding me back and
took the leap over my gender cliff, not knowing what was going to happen. On
the other hand, I had done a lot of homework on what would happen if I did
jump. All the way from testing my sexuality with men to socializing with the
lesbian culture, I tried to cover all my transfeminine socialization bases as I
slid down my path. Never being totally out of control.
The best part was the reception I received when I took my
final gender leap. All the trust and time I had spent with women over the years
was completely repaid and they provided me with a soft landing into a world I
had only dreamed about as a transgender woman.
Hi! Thanks for reading along and no matter where you are on
your life’s journey, I hope it is a successful one for you.
Anytime you have for comments is appreciated.

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