Sitting Pretty

Image from JJ Hart.

It never took me being a genius to figure out my appearance as a woman would cost me much more than my male self ever did. 

I started out my feminine life innocently enough as I began to save my meager allowance to buy a few articles for my girl wardrobe. I even took on a rural newspaper route to add a few dollars every week to spend on whatever I wanted. The problem was, finding my way to a store where I could attempt to spend my hard earned money. 

Our family home was actually in a rural area outside of town and I needed to figure some sort of an excuse to make it into town by myself because all I had was my bicycle. I figured out the answer which came to me when I was asked to go in town and visit my Grandma. She just happened to live very close to the downtown area and probably would not resist any attempts on my part to go downtown alone. I knew also, there were several stores downtown which sold makeup as well as other feminine accessories. So close but so far.

Predictably Grandma didn't and I had free reign to go shopping on my own. Then, the next biggest hurdle came along when I had to actually go into a store and shop for any makeup I found that may be suitable. The first time I was brave enough to shop for my own makeup, I was panicked and just wanted to buy something and get out of the store. Another problem was my Dad worked a short distance from where I was shopping and if I was caught, I would have no answer to why I was buying makeup. He never did catch me and the only hurdle I needed to face was the clerk who would be checking me out with my purchases. 

I was able to visit Grandma and do my shopping with no problems except for my extremely limited financial resources. Even though I managed to buy appropriate makeup, panty hose and even shoes, there was no way I could ever afford a suitable wig. For years, the wig of my dreams was just a fantasy of mine. Even so, time flew by and I managed to survive, even with my gender issues. It wasn't until I was out of the military did I realize how much sitting pretty would cost me. 

Dressing head to toe as a woman still proved a challenge for me to afford. Most of my needs would be met by going to thrift stores in our area. By doing so, I was able to find fashion "treasures" which were added to my growing wardrobe. While the thrift stores were cost effective for me, so many other aspects of cross dressing myself were not. Due to the size of my feet, thrift stores were out and I needed to shop retail. The whole process of adding new makeup, accessories such as purses and jewelry was a challenge because for the most part, my wife had control of the family finances. Through it all, going to a wig shop and buying a wig was still very difficult and frustrating. What I mean is, once I was able to put together a quality outfit, I was still struggling with having a wig to finish off my look. 

Finally, my financial situation improved to the point where I could afford a quality wig but then I needed to figure out which wig I could buy. Initially, I was like a kid in a candy store and picked out the wrong wigs which made me look like a clown. Through all my fashion errors when I was out in public for the first time, I finally was able to buy the correct wig which fit me well and framed my face correctly. It turned out the wig was the final piece of my presentation puzzle. 

For the first time ever, I was able to do my best and sit pretty as a novice transgender woman.