My Sister Taught Me To Crossdress ...my Mother Taught Me To Love It.At first, it was just a game. My sister wanted a girlfriend to play with and I was the only one around the house. I was 8 and Cin was probably 10. We had fun pretending and all day she dressed me in different skirts and dresses even though most were too big. At the end of the day getting ready for bed, sis wanted me to pretend I was visiting her for a week and she wanted me to wear some of her jammys. We lived at home with my stepmother as a single parent family and she thought it was harmless fun and was happy to see her real daughter, Cin, out of her mood. It was probably then that I began to feel closer to them than I ever felt before. And it gave me someone to bond with since my dad had passed. Somewhere along the line, mostly with my mother's encouragement, I learned to love how girl's clothes felt. Eventually, I even learned to find comfort in my mother teaching both my sister and I to be proper young girls.
Before "vacation" was over, I discovered the embarrassment and excitement of shopping for a new wardrobe of all new girlish clothes for me. By that time, Mother had put curls in my somewhat long hair and dressed me in a bright yellow sundress, flip-flops and pink painted toenails and eventually, even panties and a bra. I was embarrassed as she pulled me to the car ...then very definitely ashamed for the first time in my life as I stumbled through the mall seeing so many young boys my own age in jeans and tennis shoes. At some point, probably once I realized my secret was safe and with Cin pulling excitedly at my arm, it would be fair to say my emotions moved to being excited ...and then nothing less than thrilling. I think i remember every single store we went into that day.
Through the teenage years I was home schooled and learned to be comfortable in all sorts of girlish attire, and more importantly, with myself. Yes, of course, there were times I wanted to be a boy again, but my mother always found a way to remind me how much I loved being a girl. Now I am a few months out of my teen years living with my sister and trying to find where my heart will lead me.
kayleew2000 18-21 27 Responses 33 Mar 27, 2012