Dear Auntie Helga,
When I was 16 years old my body started to grow breasts just like the girls my age. It was a terrifying ordeal which lead my mother to have me looked at by a doctor who confirmed Gynecomastia. It was a series of appointments to look at surgery and also drugs to help me get rid of my growing breasts. None of them turned out to be an option for me due to drug allergies and my blood type. My mother was very supportive of my problem helping me discover ways to hide my breasts. Once again over time there was no hiding them as they continued to grow and develop. Most of the time I wore a binder or sports bra and then spent most of my time at home afraid to be seen in public.
One day a few years later an old friend moved back to town surprising me one day at the door. Norma was equally surprised as she stood there looking at my breasts wondering what happened. After a few hours of conversation with my mother Norma understood my problem. My mother offered Norma a place to live until she got settled with a job and her own place. Norma and I spent a lot of time together getting to know each other again. It was Norma's idea she take me to have a proper bra fitting and for me to be proud of my breasts instead of trying to hide them.
Reluctantly I went with her one day to a shop where the owner took the time to measure me properly. An hour later Norma and I walked out with me wearing a full support underwire bra showing off my breasts. The good thing was Norma's car was outside the door of the shop. When we got back home my mother was shocked at my appearance not knowing how large my breasts had grown with me hiding them before. I always wore shirts too big for me to help hide my breasts. My mother had an idea of me trying on one of her sweaters just to see what kind of shape I had with one of my new bras. To her surprise the sweater fit and according to her and Norma it looked perfect on me.
This began a series of times when my mother or Norma would have me try on certain articles of women's clothing. With me not being a very masculine guy my mother and Norma hinted at me wearing more and more women's clothing around the house. They had me in dresses, skirts, blouses and heels within a week. Oh, I tried to talk them out of their ideas with no success. One day Norma convinced me to let her apply makeup to my face just to see how feminine she could make me look. Silly me agreed which was the beginning of my new life after my mother took a look at me. My mother told me I looked better in makeup and wearing women's clothing than in oversized shirts. My mother convinced me to try living as a girl for a while just to see if I liked it and if I could pull it off.
Before long my mother and Norma filled my closet with outfits, shoes and my drawers with panties and bras. I began living as one of them with my mother and Norma helping me learn. My mother taught me how to look after the housework from cleaning to laundry while Norma taught me makeup and clothing. I wore a maid uniform in the daytime while working for my mother and skirts and dresses at nights and times I was with Norma.
It was overwhelming to say the least but I learned more as time went on. A friend of mine who also has Gynecomastia convinced me my mother and Norma were planning on making me their sissymaid but I wasn't so sure. It was on the back of my mind every morning when I put on my maid uniform however I thought my mother and Norma were just training me how to be a girl. For some reason I never thought my maid uniform was a step toward me being a sissymaid until one day I was put into chastity.
Although I followed my mother's orders she had other plans for me with the help of my friend Norma they started to train me to be their sissymaid. They had done their homework where I thought it was to train me how to be a girl. My mother arranged for me to have my body hair removed by laser in an attempt to feminize me more. Weeks later I had my hair done after years of wearing long hair my mother took advantage of it.
It's been months now with me living as a sissymaid and Norma's girlfriend. My mother and Norma take me shopping at least once a week with me wearing something other than a sissy dress. Oh yes I forgot to mention I graduated from maid uniform to sissy dress at home. Neither my mother or Norma have any plans of taking me out in public in a sissy dress but I am expected to go out in a dress or skirt when requested. It's still terrifying to walk with Norma or my mother though a mall clicking my heels as they do.
My mother is convinced I'm a happier person living in a feminine world where I can feel free to walk in public something I hadn't done for years. She is also happy to have a maid which gives her time to go out with friends and come home to a clean house. Learning to do the housework took me a while but I have it down pat now. I don't mind spending an afternoon ironing for my mother and Norma while they are at work. Seeing the smile on their faces each night when dinner if ready and the house is clean makes me feel great.
My mother plans for me to marry Norma in the future where I will live as her sissymaid for the rest of my life. For those boys or men thinking of becoming a sissymaid for mothers or wives I strongly suggest you share your feelings with them. You will be surprised most women would love to be your Mistress even if you don't think so. I myself never thought my mother wanted to be my Mistress or wanted me as her sissymaid. I'm lucky to have a mother and a girlfriend who love me as their sissymaid. They have taught me how strong willed women can be.
Thank you for your letter Liliana. I understand how difficult it must be to grow up as a boy only to discover you're growing breasts, coming to terms with this condition had to be challenging for your mother as well. Norma has been a big help and now that you have found your true purpose and direction in life, given the circumstances along with the love and support you've received from them both, you have a long happy life ahead and we are all thrilled for you.