Dear Auntie Helga,
When I was little my mother used to put my sisters dresses on me. It was something she did when I was at home on the weekends but I never knew why she liked it so much. As I got older there was less of the dressing as it faded away. I never asked why it stopped or why it happened in the first place. My mother and I stayed close especially when my sister moved to Australia. One thing I never forgot was the feeling of wearing panties, dresses and leotards.
When I was 18 something came over that drew me back to having an interest in girl's clothes. It was then I found out about petticoating and sissymaids. One night while looking at one of the monthly letters my mother walked in to see what I was reading so I showed her thinking my mother was pretty cool. My mother was surprised to see a website with pictures showing grown men wear little girls dresses. She asked me what I thought about it and I admitted I found it interesting for some silly reason. Maybe it was wearing dresses as a little boy or having my mother there as a reminder. For as many times as I looked at pictures and read the letters the feeling I had was never as strong as it was when my mother was with me that night.
The next day my mother asked me if I remembered how she used to dress me up when I was younger. I said I remembered some of it and asked her if I liked it or if she made me do it. It wasn't a bad thing the way she described it to me as I never remembered it leaving bad memories. Out of the blue my mother asked me if I want to experience wearing women's clothing something like the pictures we looked at the night before. I could see my mother smiling so I thought she was joking with me. It wasn't something I wanted to do or didn't want to do but stayed on my mind.
It was later the same night when I went to have a shower when I found a pair of panties and a long nightgown on my bed. I hesitated then looked down the hall to see if my mother was watching but she was in bed. It was then I put the panties on and the nightgown. It felt really nice and had been such a long time with the memories coming back to me. The next morning my mother never mentioned it at breakfast and neither did I. While eating my breakfast my mother went to get dressed leaving me to think about the nightgown and panties I slept in the night before. When I finished breakfast and went to get dressed since I wore my pajamas to breakfast my mother had left a bra and another pair of panties on my bed.
I never wore a bra before and once again looked to see if my mother was in the hallway. The panties went on first as I looked at the bra trying to decide but I put it on. When I was dressed in my jeans and t-shirt I went to help clean up the kitchen which my mother and I always did together. I noticed my mother look to see if she could see if I was wearing the bra as it showed through my t-shirt. My mother didn't say anything until she was ready to go out shopping. She asked me if I wanted anything at the mall which was normal and my answer was the usual no thanks. Hours later my mother came home carrying a few bags so I helped her with them. I went back to surfing the internet reading more about sissymaids until my mother call me. When I walked in my room my mother told me she couldn't find a sissy dress but she did find me a maid uniform holding it up to show me. No questions were asked but instead an assumption I wanted to go further than a bra and panties which I was wearing. My mother motioned me to come in as I stood in the doorway. She asked me to take off my clothes so I could try on what she bought me. I don't know why I didn't say anything but instead I just did what she asked of me.
My mother showed me the several pairs of panties she bought me passing me a pair. She bought me 2 bras which she helped me put on to determine which one fit the best. I stood there like I was hypnotized with my mother showing me stuff and basically dressing me. My mother put stockings on my legs clipping them to a girdle that held me tightly around the stomach and bum. She put the maid uniform over my head and buttoned it up before giving me a couple of pairs of shoes to try on. One pair fit better than the other as I looked down at my legs and myself wearing heels like my mother. She took me to the full length mirror to look at myself wearing a real maid uniform with heels and stockings.
I stood there in shock not saying much with my mother asking me how I felt. I looked at my mother letting her know I felt like I had done this before. She asked me if it was what I thought it might be and if I happy she bought me the maid uniform. My mother told me I looked like a very pretty maid and I reminded her of when I was younger again. She showed me some of the other things she bought me which included a couple of baby doll nighties to sleep in. After putting everything away we went to talk in the family room. Once again my mother told me I looked so pretty and she was happy with my new look. My mother asked if I wanted to be her maid, sissymaid and did I want her to be my Mistress.
I wasn't sure what I wanted from my mother even though I read about Mistresses and thought I wanted one. Was my mother the type to be a Mistress, I wasn't sure. I asked her if she wanted to be my Mistress which would make me her sissymaid. She looked at me asking did I want her to wear black and dress very sexy at times. I answered back letting her know if she wanted to learn to be my Mistress and dress sexy it was something I would like to see. My mother agreed to give it a try the next day. She asked me if I wanted to be a sissymaid like what we read about. I wasn't sure about what my mother was asking so I looked puzzled. She said you know a real sissymaid not just a maid. I thought about it and let her know I liked the stories of Mistresses controlling their sissymaids. My mother said okay, she was willing to try all of it to see if can be a sissymaid. She told me it would mean she was going to punish me when I made mistakes and make me wear a chastity device on my penis just like the other sissymaids. I didn't like the idea about punishment or chastity but my mother said I will either be a sissymaid or a maid. She waited for me to let her know and I said sissymaid. My mother said good she was looking forward to being a Mistress too.
My mother asked me to stand up while she looked me over playing the role of Mistress. She reminded me of an article we read together where the husband was just starting out and his wife sent him to shave all the hair off him because sissies are not allowed to have hair like men on their bodies. My mother told me to shave all of me too in the morning and let her inspect the job before getting dressed in my maid uniform. I thought wow, my mother is learning fast. The next morning I did as I was ordered to do and called my mother in to see me. She took a good look lifting my balls and checking the crack of my bum.
My mother opened a bag pulling out a shiny chastity device with my eyes looking at it. She reminded me I wanted to be her sissymaid and all sissymaids wear chastity devices right? I replied yes Mistress for the first time as she smiled at me letting me know she was pleased. Mistress took my balls in hand as she worked the chastity device around them then slid my penis in the cage part. Giving it a tug to make sure it wasn't going to fall off she closed the lock. Mistress told me to get dressed and be ready for inspection in 10 minutes. I called Mistress back to my room to show her I was ready and dressed. Mistress asked me to lift my uniform as she was checking to see I had on the girdle and all the garters were attached to my stockings.
Mistress told me I did a good job for a first time and to follow her to the laundry room. She explained as her new sissymaid my job was going to be just like any other maid working in a house. I was going to do all the laundry, change her bed every other day, iron her sheets and her clothes along with a lot of cleaning. It was then I started living as my mother's sissymaid learning all aspects of obeying a Mistress just as I had read.
Mistress was and is always fair with me and even asks me how I enjoy being her sissymaid once a week. She still acts like my mother with a Mistress twist to her. It was my dream or fantasy to become a sissymaid just from reading and thinking of my childhood with my mother. Mistress continued to read about her role trying different things out on me like weekly milkings while I remain in chastity. There has never been any talk of being released from chastity so I think it is here to stay. I do miss masturbating a lot however I realize sissymaids are not permitted to ejaculate for pleasure only through milking according to my Mistress.
The hasn't been any talk of me not living as a sissymaid either so I think it is my destiny for a very long time according to the way my Mistress talks about my future. My Mistress did hint about finding me a Mistress wife someday however it won't be anytime soon as she enjoys the life with me as her sissymaid. There are things I miss doing and have asked about them however my Mistress usually says she doesn't think so giving me the hint not to ask. For anyone out there who thinks having a mother for a Mistress is easier or if you think you can read her forget it. When my mother changed to Mistress it changed everything about her so I can no longer read her like I used to years ago. My mother is my Mistress and I am her sissymaid, her property and no longer her son.
All the best to Mistresses and their sissymaids. It's a great rewarding life if you work at it. If you don't be prepared to be punished severely.
Thank you for your letter Sissymaid Holly. What a wonderful turn of events, your childhood helped prepare you so well for your future, one of the many reasons we at PDQ advocate for petticoating at an early age and obviously in your case it was worthwhile. I am so happy for you both as you embark on this amazing adventure and so long as you remain obedient, your life as her sissymaid will succeed.