Dear Auntie Helga,
This is my first time sending a message to someone on the internet so please excuse me. I wanted to ask you a question about sissymaids and how it happens. You see I am a young guy at age 20 who lives with my 77 year old grandmother helping her with things she is longer able to do as good or alone. What I wanted to know is if I wanted to be my grandmother's sissymaid is that allowed? I am not sure from reading about sissymaids if I can be one for a grandmother or do I have to wait for a Mistress or a wife some day?
I like sissy dresses and when I see pictures of sissymaids cleaning and ironing something inside me tells me I am supposed to be like them. My grandmother is easy to talk to for me so I asked her what she would think of me if I wanted to dress like the pictures I showed her. At first grandmother thought I was joking around with her and it would have been easy for me to back off at that point with no harm done. I didn't push the issue to show respect for my grandmother in case it was something she was uncomfortable with at the time. The next day we were folding sheets when she asked me if I was serious about what I asked her or was I just testing her. One thing about my grandmother is she's smart and always can see through what people say to her. To answer her question I thought I wanted to be her sissymaid which was a term she had not heard before. We talked about what I wanted to do while looking at some pictures together. I felt comfortable talking with her and she was alright after looking at a few pictures. She did make a few remarks both positive and negative but that was okay. In the end my grandmother wanted to think about it more and for me to look into it with someone with some knowledge so that both of us understood the risks or challenges to our existing relationship.
Today grandmother wanted to know what I found out but I was too scared to send you a message Auntie Helga. My grandmother told me she wanted me to ask someone preferably a woman with experience. She went on to tell me depending on what I came back with she was alright with the idea as long as I bought all of my own clothes and lingerie. Grandmother told me most men will run away from lingerie in a store but she wanted me to know if I was going to be a sissymaid or maid of any kind my job was to buy my own everything. She would be willing to help but not do it for me. I thought that was fair if you end up telling me I can be a sissymaid for my grandmother. To do what she asked of me I am here sending you a message and hope that is alright.
Thank you for your letter Colin. I am so pleased to hear that you are such a loving grandson. Really I see no problems with you becoming her sissymaid, you seem to want to be a sissy and thats great, and you wish to serve the woman that means the most to you, so it seems best that you tell her you can be her sissymaid. Please do keep us informed and good luck.