Dear Auntie Helga,
When I was younger I advised my mother someday I wanted to work at the hotel with her and be a maid. My mother has worked at the hotel for 25 years as a senior maid. I don't remember talking to her about me being a maid but she told me about it last week when we were looking at old picture albums. She asked me if I still wanted to be a hotel maid like her when I laughed at the thought. In my defense I advised my mother that I am a guy and not a woman. Then I looking her asked if they have guy maids or was she fooling me. Mother looked over at me advising there are guy maids called sissy maids however none at the hotel.
When I asked what a sissy maid my mother gave me the run down telling me guys that dressed in women type dresses for their mothers and wives. She said some dress in French maid costume dresses and some actually wear a uniform like hers. Mother asked me why the interest in sissy maids when I didn't know just curious. My mother has a good sense of humor so she mentioned I could try on one her uniforms if I wanted to get an idea. I of course denied that offer pretty quick with my mother laughing. She told me that the offer stands anytime I want to try on one of her uniforms just let her know and she will help me.
Since then I found information on the web and eventually found your site Auntie Helga. My mother wasn't fooling when she told me about sissy maids. A couple of days ago my mother came home with a uniform in a size to fit me since hers would not fit me. I asked what was in the bag when she told me a uniform and a couple of other things just in case I decided to change my mind.
A few days later...
When my mother came home I let her know about your email which she wanted to read. After she read it she said see lots of sons are sissymaids and all she is asking that I try it.
I said I would try it for her and Auntie Helga when she gave me a hug. We went to my mothers room when the stuff was sitting. My mother passed me a pair of panties sending me to put them on and come back. Why panties I asked her. She told me I would have a hard time pulling pantyhose past boxes.
I came back wearing panties blushing to boot. My mother continued passing me things and showing me how to put on a bra and pantyhose. A few minutes later I was wearing a maid uniform like hers. I had on white maid shoes like hers. The number of times I wanted to be a maid when I was little was coming back to me. My mother thought I looked cute in a uniform. She talked me into trying out being her maid for the weekend. I had other plans but for my mother I thought okay.
My mother wants to show me what it is really like to be a hotel maid. She is going to teach me everything this weekend. Auntie Helga you know I don't feel embarrassed now that I am dressed. It was just the panties and bra when I was blushing. Maybe my mother will like me as her maid and I can do it more often. Would that a good idea to ask her later on in the weekend?
Thank you for your letter Wayne. Its not all that unusual for a mother to want her son to become a maid, in fact, many have their sons as sissymaids, happens all the time. Relax, try it for her, she sacrificed so much for you, you can do this for her. I suggest you thank her for it and ask her to help you learn.