Tuesday, March 15, 2022

Did I Really do That?

 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.


  1. Being one of the unfortunate ones who began suffering from the effects of genetics and testosterone on my hairline in my teenage years, I have always been at the mercy of “helper hair.” I was, however, lucky to have had a mother who wore wigs, and I accessed them, along with her clothing and makeup, from the time I was 10 years old. My mother’s wigs were of pretty good quality, but they were definitely more mature in style than what a girl my age had. Actually, though, my desire was to be a grown woman, so it was fine with me (my dream was to be old enough to run away to another city to start a new life as a woman, and, I thought, the sooner the better). I also acquired a wig that I commandeered from a bandmate when I was 15. It was a rather moppy-looking black page style that was befitting of a rock musician in 1966. I taught myself how to curl and style it, though, and despite the fact that black hair did not look the best on me, I did a fairly good job of femininizing the style. By then, I had also acquired my own wardrobe, so it was quite a relief not to have to “borrow” anything from my mother’s bedroom.

    A couple years into really feeling I could be myself (not what I had been afraid was becoming some kind of Oedipus Complex), my mother found where I had hidden my clothes and makeup. I came home from school to find it all laid out on the kitchen table, and then she told me to pack it all up and take it directly to the county dump. I was so ashamed that I dutifully followed her instructions, but not so much that I would also include that wig, which had been hidden in another place. Nevertheless, that forced purge was to have been the beginning of my gender identity/dysphoria, which lasted a full seventeen years.

  2. PART TWO:

    At the age of 34, I was married with two young daughters. We’d just bought a house, and I was anxious to fix up the unfinished basement to make an office for my part-time business, as well as shelving for storing all of those seldomly used things, such as holiday decorations. I’d already put a door with a lock on it for my office, and then, late one night, I started organizing things on the shelves. When I got to the Halloween box, I took a peek inside. There it was: that black wig, along with all sorts of makeup. Now, I had worn that wig a few times on Halloween before, but it had been part of a monster-type of costume when I had. On this night, though, it brought back every memory of my feminine-self. I took the whole box, along with an old mirror that was in the basement, into my new office and locked the door behind me. Doing the best I could with what was available, I put the wig on my head and made up my face. Looking at myself in the mirror, I remember whispering, “You can do so much better than this.”

    Money was a little tight after just having had bought a house, but it was probably more on my mind to rebuild a feminine wardrobe and accessories as cheaply as possible out of my renewed guilt. My wife had a basket full of makeup that she’d given up on, so I could easily take what I needed from that. I ordered a dress, a pair of heels, and some undergarments from the Sears catalogue, which I could discreetly pick up at the store’s will call. A new wig, though, was more difficult to find without, I thought, outing myself. Somehow, I discovered that K-Mart sold wigs, so I got what I determined to be the best one that was available at the time. It was brown in color, just as my mother’s wigs were, and somewhat contemporary in style (as contemporary and stylish as one might expect to find at K-Mart, anyway). I remember shunning the blonde wig, at the time, as I thought it to be “overdoing it.” I bought that wig, along with a set of wrenches as an attempted cover, and thus began my return to the pursuit of womanhood.


    So, yet another seventeen years later, I was 51, and still in lonely pursuit of womanhood – still mostly within the confines of my basement office. I had made the office more legitimate by taking my business full-time, which also afforded me the luxury of creating my own schedule. A PO box gave me an address for receiving catalogue orders, so I could buy new wigs (and other things) without fear of being discovered. My collection of wigs included all different lengths and colors, each one procured as an effort to find “the one” for me. I had left the house only to drive around in the middle of the night, which was something I had done a number of times back when I was 14 – 16 (another story I’ve told before). Still, I wore only my most-conservative wig, so as not to draw too much attention at a stoplight, should someone look over to see me. My slutty look was only attempted behind closed doors, and those wigs and the tight clothing neither saw the light of day or the streetlights of night.

    I knew that I couldn’t wait another 17 years to make my next move, which, of course, was presenting my womanly self to the world. Still, it took a whole five years before I decided to attend a meeting of the local trans social group. By then, I had settled on a mid-length brownish with blonde highlights wig as the one for me. Going back to my conservative nature, however, I wore one that was the same color but shorter for the meeting. The old church, in which the group met, was in a residential area. The only parking I could find was 2 ½ blocks away, so I ended up walking in the dimming light of a sunset on an Indian summer evening, past many people and families enjoying the delightful weather. By the time I reached the old church, I had exchanged smiles and pleasantries with about a dozen people, and there was not even one detection of negativity. Walking in the door to the meeting room was anticlimactic, even though the trans women inside did make a big deal out of welcoming me.

    Within a year after my release from a self-imposed prison, I came to realize that all of the different looks I had created behind closed doors had been strictly for my own amusement. I never wanted to be the subject of someone else's amusement, and I’m so happy that I never exhibited my more-unsavory and less-than-flattering looks to the public. Despite the remark made by a cross dresser to me at one of those meetings, I am so much more that a “professional cross dresser” because I’d always have to wear a wig. I’ll admit to not like seeing myself with a bald head, and I have never been seen by anyone in the last 20 years without having something on my head, whether that be a wig or just a towel wrap.

    Instead of being the member of a cross dresser group now, I do interact with women who wear wigs in a Facebook group. One thing I’ve learned is that women who wear wigs can go through some of the same trial and error that I went through. Most of them wear wigs because of hair loss due to chemo, alopecia, Covid 19, or even a form of male pattern baldness. As far as I’m concerned, I’m in very good company. Under our “helper hair” we are all just women who want to be seen as feminine beings. Hair is important, but one does not need to flip her wig over it. ;-)

  4. I guess I can get awfully wordy sometimes, but your post really got me to take a long look back at myself and my wig journey (actually, my long road toward transition). Anyway, I had to submit my comment in three separate installments (since it's such a long hairy story?). :-)