A Day I Remember

it was a rainy spring in my 4th grade year. when i came in from recess the teacher was angry that my pants legs were wet again from playing in the water puddles. she told me that the next time it happened, i would find myself wearing a dress until my pants legs dried.
try as i might, it was just a few days later that i came in with wet pant legs, which my teacher immediately noticed. she took me right into the cloak room, and looking down at me asked if i had remembered the conversation from earlier in the week. i was trembling and looking down at the floor. when she asked me again, i began to beg her to not put me in a dress, pleading that i would not let it happen again.
she would have nothing to do with my begging or pleading, and asked once more for me to tell her what she said. I said that she had told me i would have to wear a dress. i remember her smile, as she looked directly at me and told me to take off my shirt. as i slipped out of it, she slipped a jumper over my head. then she told me to remove my pants. i was trembling and humiliated. she told me that either i could remove my pants or she would do it, but either way, they had to come off so that they could dry. i slipped off my shoes and then my pants. "that's a good boy," she said. she hung the pants up in the cloak room and then took me by the hand back into the room, which was divided into a girls side and a boys side. she had me sit with girls. i still remember all the giggles from the girls and boys. the afternoon seemed to last forever. at the end of the day, i stayed in my desk until everyone left. the teacher came up to my desk and asked if i had learned my lesson. i whispered a yes. then she said, "now what will happen if you come in with wet pants again?" i said that i would have to wear the dress again. "that's right. now be a good boy and go get you pants and shirt on and head home."

when i got home my sisters were both already home. the teasing started immediiately, as they had heard what had happened to me. "so you like to wear dresses, eddie?" "wait until mom gets home and she hears the news." i begged and pleaded with them to not tell mom .. they agreed, provided i would do whatever they wanted. i felt trapped and agreed. for the next several school days, they would have me dress as a girl from the time i got home until just before mom came home from work. it began with just wearing a dress, but they soon were bored with that. they added panties and a bra, tights, and heels as the time went on. they also insisted that i wear panties to school every day. this went on for about a month, when they seemed to become bored with it, though they kept making me wear panties through over the next year.
ed424 ed424
36-40, M
1 Response Jan 8, 2013

Lovely story! I wonder if you deliberately got your pants wet that fateful day so you would have to wear that jumper? ...or was it just an accident?

Unfortunately it sounds like neither experience was a fun one for you, so perhaps hurt or delayed your enjoyment of girl/woman's wear. Hope it didn't.

But thanks for sharing this story!