I first began crossdressing around 7 or 8 years old. I don’t quite remember exactly when, but I do remember going into my mother’s room when nobody else was home (except my sister) and putting on a dress that was folded up at the bottom of the drawer. I also grabbed a brown bath towel to wrap it around my head, pretending it was long hair. Thus began my descent into this exciting state of being.
As the years went by, I dressed occasionally. It was always when my parents were away and involved sneaking into a room, looking through a closet or drawer looking for something to try on. Of course, through these times I felt very confused about who I was and where I was going with all of this. For a young boy into playing sports and hanging with the guys, it was difficult to comprehend the compulsion to put on a dress! However, I kept doing it from time to time, sometimes ‘borrowing’ clothes for a few weeks (hiding them in my closet in a box). Essentially, during these years I crossdressed infrequently while constantly hiding my true feelings from everyone.
A lot changed the day I got my car, because I planned to go to a store to buy my own clothing for the first time ever. This was such an exciting time for me because I would finally actually possess my very own stuff.
I decided that I would go to a clothing store and tell the checkout clerk that I had lost a bet on the NBA championship and would have to dress up like a girl. I wandered into the store nervous as hell but still excited for this unique experience. I remember swiftly walking through the aisles while trying to discern what would be right for me to purchase. I ended up grabbing a t-shirt and a skirt before heading to the lingerie aisle to browse. This was the most nerve wracking part of the whole shopping trip, because I was so sure that everyone was looking right at me, even though in reality only a few were. Anyway, I was able to pick up some underwear in the midst of all my craziness.
After scurrying to the register, I remember kind of fumbling with my words. The cashier didn’t say anything back to me, but luckily didn’t make a big deal as she scanned my items. I quickly paid and then left with my new clothes.
From this point on, dressing was as simple as locking my bedroom door and grabbing clothes out of my hiding spot. To many, this seems like a very small thing, but in the life of a crossdresser, it truly is a fantastic step.
Stay tuned for more of my personal journey, next time I will talk about my college years.
I appreciate any feedback and would love to hear your stories about your first experiences in this wonderful world of crossdressing. Feel free to comment or send me email.
JessicaWhoHD
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