Sheery the Crossdresser

Dear Mrs. Rainwater,

I’ve always been very curious when recalling my path leading up to becoming a crossdresser (and likely a future transvestite roaming the streets). It all seems to trace back to you as my teacher in my very first year of school when I was just five years old at the time. Actually those memories of you are still quite vivid in my mind.

I remember you would always wear those blue tights with sandals that would let those glorious hosed feet show. On those days, I would obsess over those gorgeous blue legs adding to the innocent boyhood crush I had on you. Of course, how could I forget, there was that one day where you lined up me and all of the other students and gave each one of us a big kiss on the cheek in appreciation of having us as students.

I’m sure you’re aware that doing that today would send you right to jail. However, I took it for what you intended it to be: reaffirming that crush I had on you was the real thing, even though I was five.

Since then, I wanted to be just like you, starting with the tights.

I became so obsessed with tights, that is, starting with the pairs I stole from my sister, who was catching on to my love for them. Then one day, I scrounged up my allowance money to buy my own pair of L’Eggs Sheer Energy pantyhose in an off-black color. My very own shiny, sensual, nylon-covered legs gave me such a thrill, almost as much as that smooch you laid on me years before.

Read more »

My first memories were blue
My first memories were blue (Flickr: Sumlin)

I’ll be so kind to admit it right now. I’m in my late thirties and, using my sharp math skills, have spent the better part of thirty years as a crossdresser. Even as a lot of time has passed since my first days across the border, I’ve always found myself trying to recall those first moments that would bend my gender the rest of the way.

No, I didn’t raid my mother’s drawer of bras and pantyhose. No, no one decided they would have some cruel fun, dress me all girly and proceed to laugh at me.

It actually can be traced back to first grade in grammar school and my beloved teacher, Mrs Rainwater. I can vaguely remember what she looked like. Things like her youthful face and short curly hair.

I remember one detail about her rather vividly and something that bonded me to her back then. She always wore blue knee-high socks on some days and on other days, blue pantyhose.

Read more »