Anonymous First Encounter #2

It was the summer that I was 7, my brother was 9 and our sister was 11, our father had just given my brother and me new bikes for getting good grades in school all year, as he had promised. At lunch, my brother and I started to argue about whose bike was faster and it was suggested that we have a race to decide whose was.

When our sister said that the winner could wear her clothes for the rest of the day, Mom laughed and said that it wasn't prize either of us would want and said it was more like a penalty; it was changed to the loser would have to wear her clothes for the rest of the day. My brother, sure that he would win, agreed to it. Mom told me not to, because I would loose, but I felt that I had to agree, because if I hadn't it would be like saying that I knew his bike was faster.

When I saw that I was loosing the race, I put every bit of energy that I had into winning, but my brother was clearly the winner. My sister and I got along very well, but neither of us liked our brother much -- he had a mean streak and was often very nasty. I was laying on the grass trying to catch my breath when my sister walked over and said that she was glad that I lost because she wouldn't have wanted our brother wearing her clothes. Then she told me that she would find me something really nice to wear, as if she was doing me some kind of favor.

Our mother had packed up all her best clothes as she outgrew them and stored them in the attic. When my sister told me to take a bath while she went to the attic and found something for me to wear, I went to my mother and told her that she wanted me to take a bath and that wasn't part of the bet. She told me that she understood why my sister didn't want me wearing her clothes all sweaty and smelly, that I should do it and that maybe it would all teach me not to make dumb bets that I couldn't win.

When I finished taking a bath and went to her room she had shoes, socks, blue panties, a full waist length petticoat, and blue dress laid out for me. I really was surprised, I had been thinking it would be shorts and a blouse or at worst a skirt. She told me to put on the petticoat then handed me the blue panties and told me to take off my underpants and put them on. When the dress was on, she saw that it was a little too small -- she said that she would be right back and went to the attic to get something else for me to wear.

Upon returning with a garment bag she told me that it was one of her prettiest dresses; then she opened it and took out a girl's very full pale pink petticoat, a darker pink nylon taffeta dress that had two layers of sheer organdy over the skirt and puff sleeves, pale pink panties with bright pink ruffles, a pair of pink single straps and pale pink socks with bright pink ruffles. When she handed me the ruffled panties and told me to take off the blue ones and put them on. I was dizzy and thought that I was going to pass out. As soon as I put the pink petticoat on over the white one and put the dress on over that she buttoned it, said that it fit me good, and told me to sit on the bed so she could put on the shoes and socks. I still remember the sound when I sat on the bed, it sounded so loud, everything crunched and crackled like I had sat on a pile of potato chips.

I looked for my mother to complain about the way she had dressed me -- everything felt so strange, nothing that I had ever worn felt anything like what I was wearing (my sneakers and clothes made no noise) and I was sure that the swishing and tapping of the shoes would be heard long before I found her. My mother wasn't sympathetic at all, she just told me that I looked very nice and that I should thank my sister for giving me some of her nicest clothes to wear.

When my brother saw me and started to tease me, I told him that it wasn't that bad to try to play it down. He said that if I liked wearing girls clothes, I was a sissy, I told him that didn't say that I liked it but I was sure that he would. Our sister told him that he didn't have to be jealous, she had lots of pretty clothes that he could wear and he went off in a huff all insulted.

When my father came home, saw me in my sister's clothes and found out what had transpired, I got a long lecture on how I shouldn't make stupid bets because I might loose. When he got done, I told him that wearing girls' clothes wasn't that bad and he shook his head and walked away.

In the middle of supper my father stopped eating, looked at me and said that I was to wear my sisters clothes for a week and then tell him that it wasn't that bad. Then I knew that I had gotten myself in a real mess.

It wasn't unusual for our father to take us all out for ice cream on nice Friday evenings during the summer. When after supper he said that we were going out for ice cream, I didn't want to go but I wasn't given a choice. I knew that, being dressed like a girl on Easter Sunday, everyone would look at me and, with my haircut, everyone would know that I was a boy.

I still remember the woman smiling as she handed me my ice cream cone and saying, "Your dress is very pretty, you're dressed very nice...for a boy! The worst part was my father didn't allow any eating in the car and I had to stand there eating ice cream with people coming and going and standing around until everyone was done eating their ice cream.

Sunday mornings my father slept in while we went to church. As soon as I got up, my sister dressed me up in some of her Sunday clothes. I begged my mother to let me wear my own clothes to church but she said no, my father would probably be up when we got back, but she did get a silk scarf and tied it under my chin to cover my boys haircut. There were enough girls all dressed up that I don't think that I was even noticed.

Several days later, our mother went grocery shopping and we all had to go to help carry the bags of groceries home. I was so afraid that one of my friends would see me that if I'd have come face to face with one of them, I'd have probably wet myself.

My sister always dressed me in two petticoats, a full waist length and girl's full length over it. At first the front of the petticoats would bounce up and down a lot. She had me take shorter steps, not bend my knees so much and swing my whole leg forward, Though I didn't realize it at the time she was teaching me to walk like a girl.

By the end of the week, I was getting used to having my sister dressing me up and walking around the house in her clothes and, instead of feeling strange, I think that I started to like the way they felt.

When my father asked me if I still thought that wearing girls' clothes wasn't that bad or did I need another week to think about it, I begged to wear my own clothes again. It wasn't because I didn't like wearing girls' clothes but because I hadn't gone out to play in a week.

The clothes went back to the attic for awhile, but then my sister started talking me into letting her dress me up when she and I were home alone. At first it wasn't bad, it made her happy, she was always very nice to me and made it seem like fun. One day, after nearly getting caught several times, our mother was downstairs doing laundry, and she wanted to dress me up. When I refused she said that she would tell our father that I liked wearing her clothes, and that he would probably make me wear them for a month, and then she could dress me up every day again. That changed everything -- when I felt that I had no choice it took all the fun out of it. It gradually tapered off, but it was almost two years before it stopped.