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.

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