First off I'm not a crossdresser. I discovered this site while searching for an embarrassing moments page a while back. I read several of these stories and found that mine fits right in.

When I was ten, I was going to be a pirate for the Halloween party at school and trick-or-treating. The day before, my Aunt Kay and my bratty cousin Angie came over. I couldn't stand Angie - she was a year younger than me and a real pest. It wasn't long before we were arguing and I shoved her, causing her to slip and fall. My mom and aunt were very upset, and Angie went on like she was hurt more than she was. I was made to give my cousin a half-hearted apology and Mom told me to forget about trick-or-treating, as I would be grounded all weekend. I protested, but Mom told me I was bucking for worse. Kay stepped in and said that she certainly didn't like me bullying Angie, but hated the thought of me missing out on Halloween. Mom told her that spankings never did any good and she didn't know what else to do. I suggested that I not wear my costume for school, but be allowed to trick-or-treat. My aunt frowned and Mom sarcastically said that I was being too hard on myself. Angie suggested to my mom that she make me dress as a girl for Halloween, and I screamed at her to keep her mouth shut. Kay told her to stay out of it, but Mom told me to keep my mouth shut. She said, "It would serve you right if I did send you out as a girl." I told her I wouldn't do it and she couldn't make me.

I knew I had really done it - talking back to her in front of company infuriated her. She grabbed my arm, shook me and said, "That does it young man! That is exactly what your punishment will be.  You're going to be a little girl for Halloween!" I tried to back down, apologizing and telling her I didn't mean to talk back, but she told me it was too late for that. My aunt asked her if she was serious, and she replied, "Absolutely!  Maybe this time he'll learn a lesson!"  Angie giggled with delight and Kay seemed thrilled as she looked me over. She told my mom if she really intended to do it, that she would bring over some of Angie's things in the morning and could get a wig from a friend of hers. I tried to talk my way out of it for the next hour or so. Then my aunt and cousin left and I was sent to bed early.

 The next morning I got up early and put on my pirate costume. I went downstairs, and after breakfast, Mom told me it was a nice try, but she hadn't forgotten a thing. Soon my aunt showed up with my evil cousin, dressed as a witch (very fitting). She carried in a box and asked if I was ready to get all dolled up. I tried again to get out of it, but to no avail. While Angie watched cartoons, I was taken to Mom's room and made to strip down to my under shorts. They dressed me in a petticoat, a lacey pink party dress, white ankle socks and black patent shoes with buckles on the sides. Kay put make-up on me and a long blonde wig with a pink ribbon tied on top behind the bangs. They made a big fuss, and I was embarrassed and shocked to see myself in the mirror. I looked just like a girl! I pleaded once more to be given another chance, but Mom wouldn't give in.

I was sent off to school on the bus, to begin the most humiliating day of my life. My teacher had a fit, telling me what an adorable little girl I made. She made me sit with her and the girls wearing dresses during dodge ball and took a picture of me. I had to endure harassment from the boys and some of the girls. A few girls told me it was a great costume and that other boys weren't brave enough to dress up like that. Of course, I didn't tell them I was forced into it. Trick-or-treating went worse, as I was asked several times why I wasn't in costume or what I was supposed to be, to which Angie happily announced, "He's dressed up as a girl!" It was very embarrassing!

Mom had little trouble out of me after that - all she had to do was threaten to dress me up again to make me behave!