Trial and Error

Over the past decades I have learned the hard way there is no easy way for most of us to feminize ourselves and face the public. I can't tell you how many times I was brought to tears by people snickering at me.

What happened though was I developed a thick skin while I learned to take better care of my own. Also ironically the more harassment I received, the more determined I became to present better in public as a woman. The more I progressed, the more natural I felt and over an extended period of two things happened. Probably the most important was gaining all an important confidence. More and more any resistance to me from the public was their problem, not mine.

Equally as important and a factor which took me years to research was how far reaching my possible transgender leanings went.  All of a sudden, I decided to throw my easy cross dressing trips shopping out the window. Even I learned clerks in stores didn't care who I was compared to how green my money was and easy trips to quiet book stores didn't really challenge by goal to be more feminine.

Finally I decided I had to take steps to establish myself as more than the occasional cross dresser if I was ever to explore if I could ever live full time as a transgender woman.

Here was my method as I have written about before here in Cyrsti's Condo. First I had to try to take a realistic look at what I wanted to accomplish. Little did I know how quickly I could establish myself after I quit doing dumb things like basically changing my name to match new wigs and going to gay bars looking for acceptance.  An example was when I dressed to match all the other single professional women that first night when I slid into an upscale bar stool at a Fridays outside of a close by busy mall. Make no mistake, I was scared to death! I still remember what I wore and each and every emotion like it was yesterday. Basically I wore a black pants suit with flats. With my restaurant/bar experience, I knew once I made it past the hostess stand with no problems all I had to worry about was finding a seat at the bar.

To make a long story short, I ended up becoming a semi regular at the venue and was treated well over the years.

Of course others have different yet similar experiences. Let's check in with Connie:

 "I must say that this is certainly the time for 2020 hindsight! :-)

There's so much more for a trans woman to change than just her clothes. If only it were that simple for most of us. When one becomes uncomfortable with what had once been her comfort level, pushing a few limits is then necessary. Although there are copious amounts of information and anecdotal stories that are readily available, we all must subject ourselves to some personal trial and error, if we expect any change. Learning to laugh at one's own mistakes, and to celebrate the successes, is a change for the better."

So true! Thanks!


  1. LOL Forgive me, but I'm laughing at your mistakes, too. Naming yourself according to the wig you were wearing! I think that the name of the first wig I got by mail order was "Sultry." I may have felt a little sultry in it, but I was far from being that way, I believe now. :-)

    I learned, pretty fast, that gay bars were not necessarily the friendliest places for a trans woman. Then, again, I also learned that they could be too friendly, when I was hit on by a very large drag queen one night. I was with two cross dressers, who did nothing but laugh at me, as the drag queen moved in on me with a vengeance. It was all I could do to resist the unwanted attempts of molestation and grinding against my hip as I sat on the stool. This is not one of the occasions for which I can look back and laugh, but it was definitely one from which I learned some things - about myself, as well as others.

    My first solo trip out was about six weeks after I had ventured out of the house to attend a cross dresser meeting for the first time. It was a trip to a grocery store across town to do the shopping for Thanksgiving dinner. I've always done the grocery shopping in our house, so there was some level of comfort in doing something that was routine to me. While sorting through the pile of frozen turkeys, a woman asked me how big of a bird I thought she would need for her large family. From there, after a rather long chat, I ended up writing out my cornbread stuffing recipe for her. Later, when I requested some cheese at the deli counter, the woman there responded with: Oh, that voice! Your voice is love it! No, I was not wearing my Sultry wig, but I do think I was making a rather cheesy attempt at feminizing my voice. :-)


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