Showing posts with label high heels.. Show all posts
Showing posts with label high heels.. Show all posts

Thursday, October 22, 2026

Sliding Down a Hill as a Trans Woman

 

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.

 

 

 

Sliding Down a Hill as a Trans Woman

  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...