What was your attraction to being a sissy or wearing female clothes?

[transboy]

For me, my mom always wanted a daughter and she dressed me as a girl many times until I was about 6 and in school. I always thought it was nice to wear dresses and have long hair. I still love dressing up

[lizziesissie]

In the beginning it was the wedding dresses and the idea of being a bride, following by the quinceanera and communion gowns. After, I discovered the Sissy ABDL world and quickly got my likes too.

[Betty]

My kindergarten teacher used to punish kids by putting them in frilly girls baby clothes, complete with a diaper (nappy), girls socks, pacifier (dummy), & rattle. She was so popular in the school for doing it, the school would send older kids from the upper classes for her special punishment. She would stand the student on a table placed by the classroom door so everyone passing in the corridor would see the student. The kid was usually made to stand there a couple hours so when the older kids changed classes there would be hundreds passing the door to see the sissified student.

Yep, petticoat & diaper punishment really existed in my school until about 1967.

It scared the hell out of me, but by 7 y/o I had an attraction for it, but still would never want to get punished in school like that.

Then the spring before my 7th birthday everybody elected me to play an elf in the school play... with tights. Because I was the smallest kid in the entire school, they all thought I'd make the perfect elf. So there I was in a silly elf outfit & tights in front of about 1,200 people in a school play, in a spotlight.

In the summer that I turned 7, I tried on my sister's red & blue sailor dress with puffed sleeves & red tights. When I looked at the mirror wearing them, I almost fell over because I looked so pretty. I was hooked on it ever since. But even back then, there was always the fantasy in my mind that I was made to wear the girls clothes, or had to wear them for some reason, rather than just doing it willingly. Probably a twist caused by the kindergarten teacher, or being made to be an elf in the play.