Dear Auntie Helga,
My name is Bill and I am 21 years old living with my mother. It is only my mother and me since I never knew my dad. I always missed having a dad which ended up me being closer to my mother and learning more about women than men. A few months ago while surfing the internet I was taken to a website with men wearing dresses. I showed my mother which led to a conversation about men and boys who dress like girls and women. My mother showed me one picture where a boy was with his mother and he was wearing a dress. Then another with a husband and wife both wearing dresses which I found somewhat odd yet interesting.
It was over a few days when my mother and me talked about it again with me showing more of an interest and so much she asked me if I wanted to try on one of her dresses for fun. I was very embarrassed as my mother noticed so she asked me again until I said okay. That night was the first time I wore a dress but part of me liked it. My mother liked it on me and gave me a few more things and bought me a few more including high heel shoes, stockings, a bra, a girdle and some panties. It was something we did at home with my mother adding bits here and there so I started to only wear women's clothes at home and to bed.
This past weekend I asked my mother what sissymaid meant since finding your website Auntie Helga. I mean I read it about it but was confused by the punishment and forcing aspect. My mother looked at the website with me explaining a few examples of men who wanted to be sissymaids and some who were indeed forced into it. I let my mother know I liked some of the sissy dresses and some of the ideas. She was surprised by me having an interest enough so that she asked me if I thought of being a sissymaid at home instead of just dressing in my new clothes. I asked her if it would be okay for me to think about it and read more to be sure when my mother agreed it might be better to give it more thought.
Auntie Helga, this is where I am now at the thinking stages while I continue to wear my dresses at home. Do you think it would be okay for my mother to be a Mistress and me to be her sissymaid? I thought you would know more about mothers and sons or have had others ask the same question. My mother mentioned to me sissymaids are extremely feminine which she could help me with if I wanted to be her sissymaid. The good thing as you can see is my mother is open to me being more feminine than most sons. She bought me some breast forms to help make my dresses look nicer on me. My mother has all kinds of ideas to help me look like a woman if I decide to accept them.
What do you think Auntie Helga? Would it be better if I just played dress up at home or better to be my mother's sissymaid?
Thank you for your letter Bill. What a wonderful and loving relationship with your mother, she obviously shares your love of women's clothing and being with you dressed.
I appreciate your contemplation about becoming your mother's sissymaid and of course I feel its a great idea, one you both can share in and would make her life so much easier. It happens fairly frequently that sons become their mother's sissymaid with all that implies. Dressing up is a game, becoming her sissymaid is real and would mean your obedience to her as your Mistress, I suggest you try it for a time.