Dear Auntie Helga,
My name is Blake a recently married sissymaid to my beautiful wife and my mother. I didn't start out to be a sissymaid, in fact I had no idea there were sissymaids until my mother talked to me about it. Let me go back in time which might help you make sense of my letter. I was raised by my mother who worked very hard at a women's and young girls store. With money always tight and my mother getting a discount on clothes where she worked I was introduced to wearing girls panties and undershirts, later to be camisoles. I never knew what other boys and men wore having been in panties most of my life.
When I met my girlfriend who would become my wife and recently my Mistress, she found it hard to understand seeing me in panties. She talked to my mother about it learning I had always worn women's panties so my wife adopted the same for me. One weekend my wife picked up a camisole from my mother's house that was discounted like all of our under things. This time the camisole had a built in bra which I showed my wife. She didn't see it as a big deal and rather than inconvenience my mother having to return it my wife suggested I wear it. Christmas was around the corner so my mother and wife decided to buy me a few more feminine items of clothing. They also bought me women's slacks and tops that were close to unisex clothing.
As time went on I was encouraged to wear more women's clothing giving me the impression either my mother or my wife would end up buying me a dress and high heels. I was at her house one night, since she lives only a block away, when I asked if she was planning on buying me a dress and high heels. My mother smiled assuring me it wasn't in the immediate plan unless I wanted her to buy them for me.
A week after having that thought one afternoon my mother sent me a text asking me to drop by on my way home. When I arrived my mother showed me a dress, slip and high heels asking me what I thought of her choices. Silly me thought they were for her but no they were for me. One thing led to another as you can imagine with me ending up modeling the dress and shoes for my mother. I always have done what my mother asked or told me to do so trying on a dress was just doing what she wanted me to do. Needless to say the dress and shoes fit me with my mother liking her purchases on me. It wasn't long after that my wife was involved and I began to wear dresses at home and at my mother's house. Part of it didn't bother me that much growing up wearing women's and girl's under things. It got to be a regular thing with me wearing dresses every day while my mother coached me on becoming more feminine for my wife. I began shaving my legs and armpits just like my wife did and at times we did it together.
One day when I was at my mother's house I asked her if she was planning with my wife to turn me into a sissymaid. I had been reading about mothers and wives dressing the sons and husbands and also began talking to Auntie Helga for guidance. It surprised me that my own mother knew what a sissymaid was and we were talking about it. My mother talked to me about becoming a sissymaid for her and my wife. She shared how much of an opportunity it would be and how much my wife would love a sissymaid husband.
At home my wife started to discuss me becoming a sissymaid so I was getting it from my mother and wife. I could feel the pressure from my wife and the encouragement from my mother. This went for a few days until one day when I was home on a vacation day my mother called me to have a chat. By the end of our conversation she convinced me to take a shower and remove all my body hair then call her back. I felt stupid shaving myself even after she explained how to do it and to shave everything. When I was finished I called my mother back like she wanted me to do. She asked me nicely to put on a dress she bought me with bra, slip, pantyhose and high heels then drive to her house. I couldn't believe she wanted me to go out alone but I did what she wanted showing up at her house a few minutes later looking over my shoulder to see if her neighbors were looking out the window.
When I walked in my mother's house she was waiting for me complimenting me for following her demands. She sat me down asking me to pull down my pantyhose and panties for her to see if I shaved everything which I did. My mother put this ring over my penis and then tried another until I heard her tell me she found the right one. Then I felt this cold thing going in my pee hole of my penis and over outside at the same time. A couple of minutes later she asked me to pull my dress higher so I could see what she bought me as I heard a click. Looking down I saw a shiny metal cage like thing over my penis that had a tube that went inside. I asked my mother what is that on my penis when she told me that all sissymaids wear a chastity device. I later learned my mother bought that device years ago when she wanted me to be her sissymaid but didn't have the time with her work load. Now that I am married she involved my wife to make it happen. As of just a few days ago I have become their sissymaid learning to look after the housework and laundry at both houses. I do know they ordered my sissy dresses for me to wear every day after work. This is all new to me as I try to learn what they both want me to do for them.
My mother has explained that as a sissymaid I will learn about punishment and strapon play while training to be their sissymaid. I can't say I like my situation however I will always do anything for my mother and wife. Now that they both want me to be their sissymaid I am prepared to try my best and not let them down. My mother is very patient with me and promises to teach me how to be a very good sissymaid. With her dedication I am sure it will happen.
Thank you for your letter Blake. I would agree, you were petticoated as a child and that seems to have been a positive experience. Now you have this wonderful opportunity to express your appreciation to your loving mother as well as serve your Mistress wife, an opportunity I'm sure many readers would envy.