Dear Auntie Helga,
When I first took an interest to mothers and wives helping their sons and husbands be sissymaids I thought there was something wrong with me. The more I read and the more I looked at pictures of mothers helping their sons put on maid uniforms and sissy dresses the more excited I became out it. I talked to my mom about it but she laughed as though I was kidding her. The weeks passed by with me gaining more of a desire as I read more and more. My mom noticed me reading about maids a few times but she didn't say much. I didn't want to hide it from her having let her know my desires so I kept reading about it. One day while we were out shopping my mom talked with me about my desire wanting to know how serious I was about it. I was open about what I thought my desires were while my mom shared some ideas with me of her own. Without me knowing my mom had been reading about mothers who trained their sons to be sissymaids. I was surprised my mom had read about it like me but also happy and not disappointed any longer.
My mom didn't agree with sissy dresses but did agree with a maid uniforms like maids in the business wore. My mom also agreed if I wanted her to train me I was going to need to wear everything a woman would wear like sissymaids but without the sissy dresses. So with me having the desires and my mom offering to help me we set out shopping for me instead of her for a change. While shopping my mom explained what she was looking to buy from razors to panties. I read about sissymaids but I was more interested in being a maid for my mom and not thinking of everything involved to get there. The idea I had was having my mother stand over me helping me put on a dress. After shopping on the way home I was nervous but kept thinking of the pictures I saw online. While at home my mom showed me a few pictures she has looked at on her own. Then my mom showed me a training document online with steps 1-10 which she read out loud to me.
When my mom was finished she sent me to have a bath and remove all my pubic hair like the sissymaids I read about. I was scared to start shaving but I ended up shaving everything off except my head hairs. My mom walked in the bathroom to see if I was shaving like she told me to do and smiled seeing I was already drying myself off. I went to mom's room with her following me to find she opened all the bags of stuff we bought already. My mom asked if I was sure about me wanting to go further and I could only say yes. Before long I was wearing panties, garter and stockings while my mom put a bra on me. She was having fun joking with me until the maid uniform went over my head. My mom did the buttons up while I seemed paralyzed.
A few minutes later my mom told me I looked cuter than she imagined I might. That was the day it all started for me as my mom's maid. My mom taught me all about looking after the cleaning and all the laundry for her. Each morning I put on one of my uniforms which expanded to several within weeks then went about the chores my mom left for me to do. Our relationship changed some with me more loyal to my mom than before. My mom kept buying me women's clothing and lingerie which according to her was what I desired. She convinced me to get rid of my Mark clothes to make more room for my Mary clothes. Part of me was confused why a mother would support her son's desire to be a maid but it worked for both of us.
My mom kept reading about sissymaids and male maids asking me what I thought about certain things. My mom started talking to me about going into chastity and wearing a device with a lock on it. My mom talked to me about becoming more of a sissymaid than I had been. My mom wants me to start bathing her and helping her get dressed from clothes to makeup but she said I will have to be in chastity first. We talked about it last night since I thought my desires were met when I became her maid. My mom told me she also has desires and she feels I'm ready to go to the next step for her. According to my mom sons who become sissymaids for their moms do so as a lifelong commitment which I didn't really know until last night.
Auntie Helga, up until now I have listened and followed everything that my mom laid out for me. I can see a husband bathing his wife more than I can see a son. My mom wants me to be her sissymaid and not just her maid. I wasn't expecting her to say it to me last night. Tomorrow my mom wants to take me to look at chastity devices so we can both pick the best one for me. I do have to say my mom treats me just like she always did and not like some Mistress moms I read about.
Do you think my mom is changing to a Mistress or just wanting me to explore more of the life I so desired in the beginning? I will do as she tells me and what you recommend too.
Mark (also Mary)
Thank you for your letter Mary. I am so happy to hear that you are training to be your mother's maid, I know this is going to be a very different life for you and for her, but many others have done so with great success.
Becoming a Mistress is a very attractive concept for many mothers and she seems to be thinking along those lines. I suggest you do as she desires and at all times be obedient.