Dear Auntie Helga,
I shaved my whole body this afternoon, like other sissymaids and cleaned up the tub before my mother came home. Well actually she didn't come home until after dinner carrying lots of bags like she was Christmas shopping. My mother was happy to see I was still wearing my nightgown but forbid me to look at what she bought. Once my mother got settled I decided to talk with her about sissymaids like you told me to do. I wrote down some of the things I wanted to say to help me get through it. Auntie Helga with my mother standing in the kitchen I got down on my knees with her wondering what was I doing. I took her hand letting her know how much I loved her for everything she had done and was doing for me. I talked about what a special mother she was for allowing me to wear women's clothing and offering to buy me more if I wanted her to. My mother was smiling but not saying too much except the odd thank you.
While I was talking she asked me if I shaved my legs while she was out and I showed her I shaved all of me. My mother was surprised but happy I listened to her about my leg hair. There was no turning back then so I asked my mother if she would permit me to be her sissymaid and submit to her as my Mistress. Mother asked me what was a sissymaid so I let her know and showed her some pictures. I could see my mother wasn't completely accepting of my idea so I explained all the things I wanted to do for her like all the housework, laundry, cooking, bathing and massages. Mother smiled letting me know it all sounded good but would I really do all of it for her or was I just wanting more clothes.
I kissed mother's feet begging her to allow me a chance to show her I wanted to be her sissymaid. My mother told me she wanted to think about it while she looked at the internet. She sent me to start a load of washing and I kissed her feet again thanking her. A short while later my mother called to talk with me about what she read and my understanding of what was involved if she permitted me to be her sissymaid. With a firm voice my mother told me if she agreed I was to always obey her and never ever talk back. My heart was beating faster with excitement and some sense of fear. Mother surprised me with some of her demands like she had read about sissymaids. She talked to me about living totally feminine and no more male clothes at home. Mother also told me I must be kept in chastity like the other sissymaids we saw in pictures. Finally mother told me wearing a pink sissy dress was also a must at home.
When mother was finished talking with me I told her I already bought a chastity device hoping some day to wear it with her holding the keys. Mother told me to go get it and show her which I did right away. She looked at it letting me know she liked the look of it and it looked expensive. Mother sent me to my room to put the chastity on which I had tried earlier. I had to get rid of my erection first and apologized for taking so long to get back to mother. Mother told me to show her so I lifted my nightgown and pulled my panties down. Mother pulled on it to make sure it was on there which it was snug like the directions said. I gave mother both keys which she put in her bra smiling at me. Auntie Helga for the first time I felt unsure and scared too. Mother told me to follow her to her bedroom which I did without question.
In her bedroom mother talked to me about being a sissymaid and always appearing pretty like I had started to do by wearing a nightgown, panties and a bra. Mother started to unpack the bags talking to herself about what was in each bag. Then without notice she told me to take off my nightgown and robe which I did shaking. Mother asked me how my bra fit which I replied fine so she handed me 3 more of them. she showed me more panties all of which were pink with lace accents. Mother gave me some bra forms with beads in them to fill my bra which looked and felt better. She showed me 2 girdles with garters, one was panty and the other open bottom. Mother wasn't sure if I could wear a panty girdle while in chastity so she told me to try it on to see. It was squeezing all of me and the chastity but mother said it was going to be fine. I put some stockings on which felt nice on my shaved legs. Mother asked me how I felt so far and I replied good. Then she said good what with me correcting myself with a good Mistress.
Mother told me she ordered my sissy dresses today but in the meantime she pulled out an old dress of hers to wear which I put on. Auntie Helga I was beat red and so embarrassed as my mother looked at me every step of the way. Mother pulled out 2 pairs of shoes both high heels telling me to try each pair on and let her know what felt best. I picked a pair so she put the others back in the box. Mother looked at me asking how I felt wearing the women's clothes I wanted to wear but was afraid to ask. Mother told me it was a good start and as time went on she would make sure I had more to wear. I got down on my knees to kiss her feet again thanking her for allowing me to serve her. Mother told me she was going to like being treated like a queen and I was going to love serving her as a sissymaid. Mother took some red lipstick then put it on me then handing it to me telling me it was mine to wear every day.
Next we went out to the kitchen to talk about how I was going to be her sissymaid and when she was going to train me to do everything in the house. I asked mother if she was happy to have me as her sissymaid because I wanted her to like it. Mother told me it was going to take both of us a while to learn our new roles but she was determined to help me with my dream. Mother said I looked pretty for a first time seeing me this way. I thanked her again. She asked me how much I read about sissymaids and Mistresses and I said lots. Mother told me she also read lots and was going to do what most Mistresses do with some things I may not like. Mother asked me earlier if I wanted to be a maid or a sissymaid which is why I might not like some things. I let her know sissymaid and hope I made the right decision.
I'm sorry for the long email but I wanted to let you know what happened so you can help me. My mother will start training me tomorrow with cleaning, ironing and more laundry.
Thank you for your letter Dustin. Well, congratulations, that didn't take long did it? You first wrote me only a few days ago and now you are serving your Mistress Mother, that is so wonderful and I know you will do your very best to please her in all things, just be sure to be obedient. Of course you will make mistakes, its inevitable, after all you're male, so mistakes are expected but know you will be punished if you do, this is meant to help you.
Your request and explanation to convince her of your desires was very sincere and its obvious how much you want this, really well done, I am so proud of you. (Previous letters in June and July 2017)