Dear Auntie Helga,
My mother makes dresses at home for part time money. Sometimes when the dress is a size that I fit into my mother asked me to model it while she makes adjustments. I have been doing this for a few years but more now as she makes more women's dresses. Some of the dresses are altered when a woman brings it back because she gained or lost weight. Another time is when my mom puts a bra on me and I wear high heels when it is a long dress she is making. I'm used to this after all these years.
A few weeks ago my mother got an order for a pink sissy dress which was something new for her to make. Once again my mother asked me to help out which I did wearing larger cup bra for this one. When I saw the dress on me mother made a comment that the lucky woman buying the dress was going to have her boyfriend wear it as her sissymaid.
That was something new to me when mother explained that she heard about petticoating many years ago but had not heard much lately. I asked what it was when she explained it all. I looked on the internet which led me to this website where I found you. It sounds like most mothers or wives would like to have a sissymaid.
I think my mother would like it too and was thinking of asking if she would make me my own sissy dress. Do you think if I show my mother your website that she will give it some thought? Should I tell my mother I like wearing dresses?
Thank you for your letter Gary. That is so sweet to help your mother like this, she seems a wonderful woman. Good to know she has at least heard about petticoating, I also like your comment about becoming her sissymaid. Do you really want to do this? This is a long term commitment. If on the other hand you just like wearing the dresses, which is good too, then lets see what we can do about that instead. (see Letter 4)