Possibly the first of which occurred when I was probably no older than twelve. During that time of my life, I augmented my meager allowance by delivering newspapers in the rural area we lived. I was able to save enough money to attempt to buy my own cross dressing accessories such as makeup. As it turned out, my Grandma lived within walking distance of the medium sized town we lived close to.
Once I accumulated enough money, I figured out a way I could visit Grandma and spend the night. With my plan in place, I proceeded to do it. As I was to find out, that was the easy part. Finally the time arrived to try out my plan and needless to say I was equally thrilled and scared to go shopping for makeup for the first time ever. The downtown had several of the old school variety stores before Wal-Mart and the mall wiped them all out. I carefully chose one and after circling it several times, I decided to go in. My Dad didn't work too far away and he was the last person I wanted to run into! After I was fairly certain I didn't know anyone in the store, I found the makeup counter. Then I was truly in a panic. I had no idea of what to buy, there were so many choices.
Somehow, I calmed down enough to purchase a couple items and found the nerve to go pay for them. My worst fears were not founded as she barely checked out my treasures and sent me on my way.
I changed and grew dramatically on that day. I knew from then on I was capable of buying my own feminine items. Even tough countess times I bought the wrong thing, again I was changing and growing. As it turned out, my next big purchases were a pair of my own black tights and shoes.
Little did I know, this would only be the first of many chances to expand my transition in the years ahead.