Shopping 201

Image from Brett Jordan
on UnSplash

Over the years I did quite a bit of shopping in clothing stores and malls, mostly successfully.

It took a while but I finally learned much of my success had to do with the fact my money was more important than my gender to the average store clerk. Many I think worked on commission and anything they sold was added to their paycheck. Even still, the experience was valuable in building my confidence as a novice cross dresser in the days I was running from the idea I could be transgender. I was paying my way to people so they would be nice to me. Only one time did I run into any problems when an older clerk told me my skirt was too short. In response, I left and never returned since there were plenty of clothing stores to go to.

In a short period of time, I grew tired of the same old shopping I was doing and started to expand into stopping for lunch where I needed to interact one on one as a woman with servers. The entire process opened a whole new gender world to me and for the most part I was treated politely with respect. Overall the process took me to a whole different level of Shopping 101. I grew bored and was ready for a new course I called Shopping 201. 

The new course ended up providing me with endless possibilities to expand my horizons as a very serious cross dresser. At the time, I was searching for ways to do different things in the feminine world. One way to sneak around behind my wife's back was to start doing part of the grocery shopping. I would pick times I knew the grocery store we went to would not be busy and out I went. The women's fashion trends back in those days fit me well. I could wear one of my oversized soft sweaters along with a mini-skirt and flats and look like any other fashionable woman without going overboard. One morning in particular was memorable. 

On the day, I carefully shaved my legs and prepared my wig. After dressing and putting on a light amount of makeup I took off to the grocery when my wife was at work. I arrived at the store, grabbed a cart and proceeded to pick up a few needed items. Then I headed up to the register line to be checked out. This was back in the days before self checkout so there was only one way to go. At the register there was one older cashier and one kid bagging groceries. When he saw me, his eyes immediately went to my legs and when he noticed me watching him, he blushed and stammered something about helping with my groceries to the car. Never before and rarely since have I affected a male such as that. The cashier just gave me a knowing smile. 

From there, I couldn't resist reverting back to Shopping 101 and made a quick stop at a nearby big box store to pick up another pair of panty hose and shop for new makeup. By doing so, I was able to hide my expenditures along with what I spent at the grocery store. 

I was able to negotiate the morning as my feminine self and learn so many new things so I could graduate Shopping 201 and move on towards life in a transgender world.   

Going Back

Image of Liz on left and Daughter on right
from the Jessie Hart Archives.

 Recently I read a rather sad post from a person who was giving up her gender transition and going back to her original life. 

Even though I consider myself very fortunate in how my gender path turned out, I could understand the facts the person mentioned when it came to her new life. Among other things, the person related experiences which have haunted many of us following a transition. Such as having problems with loneliness, finances etc. So many transgender women are stuck in their houses, often with just having a computer to provide any contact with the outside world. This de-transitioner was older and provided a picture which showed a very presentable senior woman. My heart broke when I saw her image, I just can't imagine going back after putting so much work towards accomplishing a goal. Perhaps it is because I tried so hard and risked so much when I crossed the gender frontier. Plus, possibly for one of the few times in my life when I ever set specific goals, I was able to achieve what I set out to do. 

One of the major differences I saw when I read the post was how I approached the gender goals I was attempting to accomplish than most others. One of the examples was how I approached on-line dating services. I went all in with three or four services with the usual results of receiving tons of trash back in the process. I tried everything such as woman seeking woman to man seeking man. Amazingly, when I was giving up, some how I ended up meeting my current wife Liz who lived within driving distance in Cincinnati, a city I had always loved. That happened over ten years ago and it all started with a date to a drag show. As an aside, Liz identified as a lesbian witch so I was intrigued. 

In addition, the lucky move I made to create a new social life came when I decided to not go to anymore male gay venues and decided to go to the sports orientated big venues I was used to. I figured if I was going to risk being discriminated against, I might as well go to a place where I could enjoy myself. The gay bars aggravated me because I was always treated as a drag queen. What I don't recommend is the amount of alcohol I consumed along the way. On the other hand, I ended up meeting several other women in the venues who became friends. 

Very quickly, going back in my transition never had to be an option. By the time I decided to go all the way as a transgender woman, I knew my daughter would support me as well as Liz and my small circle of friends. As I made the final slide down the gender slope my landing turned out to be very soft. Even still, my heart goes out to those who are considering going back. Perhaps the whole experience could be thought of an ultimate experience which failed. Or maybe, they just wanted their old male privilege's back. 

Then again reversing my life again would be unthinkable because I would be so unhappy. I am afraid the person who did decide to go back would never be happy on either side of the binary gender border. 

Changing the Gender Locks

Image from Adam J
on UnSplash

It took awhile for me to change the locks on my old male self. He kept hanging on and on to the smallest reason not to go all the way with my gender border crossing.

Through it all, he was quite comfortable on occasion taking advantage of all the male privileges he had come to take for granted. He was used to taking personal security and even intelligence for granted. Age seemingly was the only prerequisite in gaining respect. When the locks were changed years ago, life changed with it. 

Changing ones' gender is nothing to be played with. I'm biased but I think transitioning as a transgender person (woman or man)is one of the hardest things a human can experience. All the cards are stacked against you as early in life you are forced into a square hole when you are certainly a round peg. Perhaps the interesting fact of the whole gender experience is when one door opened and you went through it, often it was slammed shut and locked behind you. You then had to be quick on your feet and learn what to do next. Surely mistakes were made but it was the only way to learn. Some would call it tough gender love. 

The farther I went in life as a novice transgender woman, the more locks I needed to change. The more I entered the world and was successful as a feminine person, I felt natural and couldn't wait to lock the old male door behind me. Even when it led me to potentially dangerous situations. I write often of the times I was on the verge of being seriously molested or worse in my early days of exploring the world. One night I was dressed way to skimpily and attracted the wrong set of man. My second wife needed to bail me out of the situation so I never heard the end of it. Even still I locked that door behind me and moved on with an important lesson learned. 

I was doing what I believed in so I was stubborn and any progress gave me hope. To follow in someone else's path would just have not worked. So I said to hell with the possible consequences such as losing my three "F's" family, friends and finances, I kept changing the locks behind me. I needed a huge lock as well as amazing amount of duress and thought before I decided to go through with donating all of my male clothes and deciding to live a fulltime life as a transgender woman. Also, hormone replacement therapy was in my future should I decide to explore the possibilities of furthering my femininity through HRT.

Along the way, I became very proficient at changing my gender locks and hiding them from the everyday world. Depending on the door, often I had to stop and look around at a totally new and exciting world. Once I did, I always decided to move on seeking a new door to go through.