I had made my way to Cincinnati I was hitchhiking around the country just thinking I would like to see the world. I began to search for a job. My search did not take long I saw a sign in a window and walked in to see a woman at her table working on sewing some dresses. She looked up and wiped the sweat off of her forehead. She asked what I wanted and I told her that I saw her sign. She stood up straight and I saw she was about two heads taller than my five foot five. I told her I was wanting a job. She walked around me looking me up and down. I waited for her to complete her study of me. She asked me if I had ever been a model, I said no and ended it with why. She said her name was Miss Jones and if I wanted the job I would have to be able to follow orders without question. I heard my belly growl from lack of food and said I will do as you say. Miss Jones asked me if I was hungry, it did not take a second to say yes.
She gave me a ten dollar bill and said go get something to eat and come back. I took it wondering if she was testing me. Walking to the restaurant she told me of. I ate but not fast I thought of her as I ate. Her frame was one of a strong woman and her face soft as a flower. I remembered her hand that had touched mine it was firm but yet soft. I thought of her eyes and how they twinkled as she looked into mine. After eating I walked out the door, her place was left and the other well in my mind. I turned and walked into her shop, she looked up and smiled.
Miss Jones told me that she needed someone to work around the place cleaning and doing odd jobs for now. She took me about the shop and the other rooms that were dressing room and a stairway that lead to a two room apartment with a bathroom. Miss Jones told me I could have the apartment and the job with a small amount of money. It was then that she said I would also have to be her dressing helper by that she meant I would have to wear women's dresses that she would be fitting. She said I would have to shower every morning and shave all the hair off my body. As for the hair I had none except on my head. She walked to a dresser that was as I found out filled with women's under garments. She took out a pair of panties and asked if I had a problem wearing them, I thought for a second but the picture of her in my mind I was thinking I would do anything for her. I said no. She asked if I had ever worn female clothes before with a strong blush I said yes. Not missing a beat she ask me to tell her about it. Mind you here am I a small built man of nineteen and about to spill my sordid past as a lover of girls underthings. I had read books about males being dressed as a sissy for his lover, only to become her slave or even more her money maker. I had never been with a man OK I also had never had sex with anyone other than lady five fingers. I don't know how or why but I told her everything I could think of about my desire to be a girl. I was always teased about my body and hated other boys seeing me naked, my penis was only four inches hard.
She said go on tell me, I told her that the girl next door had stole one of my books and read it and the parts I underlined. She had blackmailed me into being her sissy slave. She made me come to her room after school and since her parents both worked about three hours and it took them one hour to drive home she had me put on her panties and a old fashion petticoat and a straight dress that she would giggle every time she saw dressed as her maid. I would wash the dishes and clean her room. She often made me wear only the panties and when I was done cleaning her house to make her mom think she had cleaned it all. Then she made me stand in her panties and stroke my small penis that she called baby girl. She would say now make baby girl dance, that meant that I was to jack*** until baby girl spit out her stuff.