When I look back on my fifty plus years of my life as a gender dysphoric person, I wonder why I did certain things. Many times I manage to come up with these memories in the middle of the night when I can't sleep. Along the way also, I try to come up with ideas for another post.
One of the most problematic times of my cross dressing life came when I became able to purchase different kinds of wigs. Similar to a kid in a candy store, I became addicted to deciding when and where to look for and buy new wigs. Sadly I was still in my "big" hair faze and ended up trying to buy and then wear the biggest hair pieces in the store. I persisted even though I had several clerks try to tell me I was making the wrong choice.
I was sure the next wig would help me to become the irresistible feminine person I just knew I was capable of becoming. To add insult to injury, by the time I tried to brush out and style a wig, I ended up ruining it further. Often all I ended up with was a clown wig suitable for Halloween, As in the picture I added.
Of course what was good enough for Halloween wasn't good enough for everyday life. What made matters even worse was when I first started to go out I would use a different name to match the wig I was wearing. For example (as I have written about before) I was Roxy when I wore my big blond wig and Darcy when I was wearing my dark wigs.
My collection also wasn't limited to big curly styles, I purchased a long dark wig once which actually matched my own hair color at the time. It was very thick and straight and resisted my attempts to ruin it. There were several good endings wearing that wig when I wore it on a girls night out with a group of servers from a regular sports bar venue I
frequented. Which you can see here.
Through it all I finally settled on a longish straight blond wig which was slightly longer than shoulder length. It wasn't till then I settled down to being the same feminine person as much as I could, without the clown hair. It enabled the public who I was beginning to meet frequently to settle in on seeing the same person.
One regret I do have is that I didn't save all the money on the wigs I did buy and invest in a a good/quality hairpiece. My excuse is I was still searching for the transgender person I was to become.
Now of course I am one of the lucky transgender women who does not suffer from any male pattern baldness. I have been able with the assistance of HRT to grow a full head of long wavy hair. Which is the envy of my daughter who has commented why she didn't inherit my hair.
Unfortunately, my experience with wigs wasn't the only ill advised stunt I tried when I transitioned but often it was the most visible one.