I started dating Dana in the seventh grade. It was not long after we started dating that she said she wanted me to do something for her. I asked her what she wanted. Her answer was to dress me as a girl. I said no way. But all the while my penis was standing up. It was only three inches long and kind of skinny but it was up. A few days later her parents were going to a wedding of her mother's sister. Her mother knew Dana had a school thing to go to and said she felt that Dana could stay by herself for one night. Dana assured her she would be OK. Dana told me a few days before that she would expect me to come over to her house at seven that evening.
When I arrived she was very bossy and told me to remove my male clothes. I did it but to this day don't know why but I was soon naked and she was laughing at my size. She took my clothes and put them in the closet and locked the door. She told me to get on my hands and knees and follow her. I crawled along behind her peeking up her skirt to see her beautiful butt swaying and move so wonderfully. She said stop looking at my butt, sissy. I looked down the rest of the way. When we got to her room she told me to stand.
Standing she handed me a picture of a little girl from back in the fifties, she was wearing a party dress and Mary Jane shoes and had bows in her hair. Dana said you will look like that before the night is done, sissy. I heard my mouth say "yes Madam". She smiled and said let us start with these she held out a pair of thick white panties. Before long I was looking in the mirror and saw that little girl in the picture. The only difference was I was crying and the girl in the picture was laughing.
I was her sissy for the evening and many days afterwards. I learned to curtsy and dance in a tutu. Dana took me out many times dressed in similar outfits and soon after she was dressing me as a teenage girl and making me flirt with boys. I became her husband and after that I met her boyfriend Charles. She said she had to have a maid and a man. I only fit one of those.
Some of my chores are to clean them up after they have sex, often using my tongue on both.
Betty Sue, Mistress Dana's sissymaid