So Many Choices...So Little Time

 

Image from Drew Colins
on UnSplash.

One thing that I learned from experiencing decades of cross-dressing is that there were so many choices and so little time.

It all started when I had to scramble for any time, I could find by myself dressing as an imagined pretty girl in front of the mirror without discovery from my brother or worse yet my parents.  I was born as the eldest son into a very male dominated family, and I was expected to fit right in with that male mold. I had little idea at the time that I was destined to break that male mold during my life and it was not going to be easy.

Back in those days, I had very little income that I scraped together from doing household chores and a newspaper delivery route I had for several years. The first feminine items I could afford to buy on my own were makeup accessories but first I needed to figure out a way to get to a store undetected and then decide what to buy. After putting a lot of thought into my situation, I remembered that my grandma lived in town, fairly close to one of the old five and dime department stores that sold makeup. I used the excuse to visit grandma, then go and shop. Or try to.

The only problem with my plan was that my dad worked downtown close to the store I wanted to try to buy my first makeup in. I was tired of using my mom’s samples, That was all well and good until I gathered my courage and walked into the makeup selection of the store I was in. As I viewed the extensive selection of cosmetics, I almost panicked and walked quickly from the store. There were so many choices and so little time to choose anything that might help me during my novice beauty program. Somehow, I stood my ground and picked out some foundation and lipstick which fit in with my limited budget, gathered my courage and headed for the checkout counter. Just knowing I would get made fun of along the way. Amazingly, the person at the cash register did not give me a second look as she took my money and I was no longer a virgin in buying my own feminine supplies. I just wished I had more access and money to do more.

I would have more financial resources later in life along with the knowledge to go with it as I learned the fun of doing thrift shopping for just the right choice of clothes to add to my wardrobe.  Plus, the thrift experiences gave me a chance to be patient in many of the bigger stores with seemingly an endless supply of discarded fashion. When I took the time to try on a new item I had never tried to wear before, I had two benefits. I didn’t have to pay much for the item and two, I could see how well it either flattered my difficult to please male testosterone poisoned body or didn’t. It helped too, when I was able to streamline the shopping experience and give myself time to vary my day as a novice transfeminine person. Instead of just facing an endless amount of clothes. I actually had time to do other things like take myself out to lunch. Then, again I was faced with an almost never-ending choice of where I could eat. Since I had already tried too many fast food drive throughs with various amounts of success, I decided to step up my game and try to eat at one of the casual dining restaurants I had went to and even managed as a man. Since I was still on a gender time clock and had to be home by a certain time dictated by when my second wife would be off of work, I was still facing so many choices with so little time to enjoy myself as a transgender woman.

My plan was to just get by and improve myself a little at a time in a world of ciswomen I was just discovering. By doing so, I discovered that most ciswomen ignored me if I was dressing to blend in with them or were just curious of why I was in their world. Of course, I did run into the occasional TERF woman who hated me and wanted me out of her world, which I did. One way or another, I was encountering far more women in my quest to be part of their world than I ever did any men because I just wanted to be out of my long-standing membership in the men’s club and they knew it. The only thing I did know was that I was increasingly not so lonely when I went out in the world to my regular straight venues. All my lesbian places had closed up and the gay venues I used to go to just brought back bad memories of me being looked at as just a drag queen so I was stuck…just where I wanted to be and I was satisfied, until I went too far and tried too hard to be accepted.

In my search for acceptance, I began to become too overconfident in my ability to succeed a began to look for more choices of where to go in such a short ill-conceived amount of time. What I did was start going to redneck themed places thinking I could be accepted when I was not and even had the cops called me one night in a venue, I was just trying to drink a couple beers then pee before I went to another place I had been to a lot. It turned out that they would sell me the beer, just not let me get rid of it.

As it turned out, I was/am able to live a long life and see many of my choices gang up on me in a very short period of time. Destiny worked its magic and gave me a full circle of life to live with. Throwing in that I was a transgender woman just added a little spice.