Dear Auntie Helga,
I live with my mom and there is no father, just us two as it has always been. My mom works at a large department store managing the women's department. She tells me funny stories about people all the time but last year she told me about a man who buys all kinds of women's clothing from her who we will call Harry. Every so often she would tell me Harry was in again and what he bought. I started to ask her what she thought of men who bought women's clothes and if she thought they were for the men. Mom has seen a number of men buy clothes from her department knowing that the clothes were for them just by the size alone sometimes. One day my mom said to me that I seemed pretty interested in these stories and women's clothes too with a smile. I didn't say anything feeling caught but not admitting anything.
A few days later mom brought home a few bags that I helped her with. She was always bringing home samples to look at and ask me what I thought. It was later on that night she brought out the bags asking me to help her pick out what I would call nice. As she sorted everything out she came across a dress and pointed out it might just be my size. She asked me to try it on then model it for her. I felt excited but scared at the same time. Mom didn't like the fit so she gave me another to try on which met with her approval. She asked me what I thought of it so I talked about the material and colors. It was then that Mom said to me that she could see me wearing something like that if I wanted to. She told me not to be shy as she could tell I liked it.
Mom went to get another bag that she said were all brands that the store wasn't going to carry any longer. She reached in and pulled out a pair of panties, a bra and a slip then told me to take off the dress and put those items on for her. I was mortified in one way and excited in another but I did what she asked then put the dress back on. Mom pulled out a pair of pantyhose and helped me put them on and finally a couple boxes of shoes. One pair of high heels fit me as Mom looked at me asking what I though and how did I feel. That was the beginning of me wearing end of the line women's clothes at home every day. Mom brought home a few nightgown sets so I started to sleep in a nightgown too. Every week she would bring home something instead of sending it to a liquidation house as my closet filled up with dresses, skirts and blouses. Mom had to buy me a shoe rack for the all the shoes I had now.
Every day I came home from work Mom would help me change into something already in my closet or a sample she wanted to see on me before taking it back to the store. She used to bring samples home in her size but started to include my size as well. A few days ago I showed Mom your website with the men wearing maid dresses which she thought was fun. We did some reading together while learning more about petticoating. Mom asked me if I wanted to be her sissymaid or just stay being her daughter as she smiled at me. I said I wasn't sure about sissymaids and that I loved being her daughter when she said she knew I did too. Last might I was looking at the website again when Mom walked in so we talked about it again. Mom didn't think she would like to see me in one of those French maid or sissy dresses. She did say that a pretty maid uniform might be nice for me though with matching white pumps.
Mom thought there were some good ideas on your website Auntie Helga and she suggested I shave myself to look more like a woman. I asked if she thought it might be a good idea to ask Auntie Helga what she thought of where we are now and if I should be a sissymaid or not. Mom agreed that it might be a good idea to get a different perspective and if not it was fine with her that we continue to do what we have been doing. That is my story or should I say our story. What do you think now? Do you agree that my Mom dresses me in women's clothes and would I make a good sissymaid for her?
Thank you for your letter Mark. What a wonderful relationship you have with your loving mother, and her acceptance of your choices speaks to her open mind and playful nature. Not all maids are sissymaids of course and for a mother and son, starting out as a conventional maid makes sense, learning the proper procedures for the various tasks as well as the proper attitude of obedience commensurate with a subordinate position will help.