Dear Auntie Helga,
I was looking at the website called petticoated.com the other week and wanted to ask you if mothers and sons can practice this petticoating when the son being me is in my twenties. Is there an age limited for the son and the mother? Maybe it would be best I tell you about my mom and me if that helps. 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 or buying for their wives. 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 a nice dress. As she sorted everything out she came across a dress and pointed out it might just be my size. She asked me if I would like 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. I asked Mom is she was sure about me wearing a dress when she said lots of guys wear dresses. Mom told me not to be shy if I wanted to wear a dress she was willing to help me as long as it was just at home.
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 thought 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. I asked her a number of times if it was okay that I dress like a woman. She continued to say why not it was fun.
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 cool although she wasn't fond of some of the dresses. 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 night I was looking at the website again when Mom walked in so we talked about it once 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 pumps.
Mom thought there were some good ideas on your website Auntie Helga like body shaving which she suggested I shave myself to look more feminine. 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. I never thought my Mom would let me even try on a dress but now she wants me to wear one every day. I think Mom enjoys seeing me wear the clothes she brings home more than what I wear to work. Mom bought me more panties so that I had enough to stop wearing boxers.
Mom is having fun dressing me the way she likes and I don't mind it either. I am glad I asked her about Harry and other men that shop in her department. 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 Jimmie. Mothers petticoat their sons no matter the age. She seems interested in pursuing this concept further and your willingness to dress in the clothes she brings home from work leaves me to feel that becoming her maid would be a great idea.