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.