Dear Auntie Helga,
I hope you don't mind me writing to you after seeing your email address on the website petticoated.com. For the last couple of years I looked at a few times a month and even read some letters two and three times. I just turned 19 last month so I'm hoping to be old enough to learn more about sissies and Mistresses. It's only me and my mom at home which means we are very close. I think I know more about women than most guys my age having an open minded mom like I do. This summer we went to the Pride Parade for the first time which opened our eyes up on everything related to those with different lifestyles.
My mom told me on the way home she liked the whole day so I asked what she liked of the different lifestyles. To my surprise she liked the guys who dressed like girls and especially the sissymaids or anyone in a maid uniform. Then she asked the same question with my answer quite similar to hers. We agreed to talk about it more a few days later with both of us needing sleep from a long crazy day. It was a Thursday as I recall after dinner when my mom brought up the subject of the parade again. We started to talk about it and some of the people we saw. Then without me paying attention my mom asked me if I ever wanted to wear women's clothing or a maid uniform. I had not thought about it for me but admitted reading about those who do on Auntie Helga's website.
My mom and I looked through some pictures and read some letters together. We laughed at some things as they related more to us. My mom looked at me letting me know if I wanted to try it she was willing to help me. I didn't say much as I thought about the parade and how much fun my mom had talking with some of the feminine guys. My mom was good about it leaving me to think before pushing me into something new. I asked her what she had in mind so she mentioned a particular sissy we saw in the parade and how much she liked that look. We talked about it with me eager to learn more but not knowing a thing about what to ask or how to go about trying any part of it. My mom could tell I was interested but had no idea about the clothing part of it. She went to get her tape measure to take some measurements while talking about what she had in mind. I wasn't sure but trusted my mom with it anyways.
Over the next few days we went shopping to look at everything I would need to be my mom's sissymaid. She educated me on styles, fabrics and the look she wanted to create with me. Each day we brought home a few things getting closer to having it all. We also talked about my sissymaid role and my mom's role as my Mistress with her telling me how much fun it could be if we both agreed. It sounded like something we both were willing to try which was nice we both agreed on it without anyone pushing too much or pushing back to much.
On the fourth day we went to look at dresses which was letting me know it was real and was getting close to happening. We ended up looking at 4 used sissy dresses a woman was selling in my size. It was the first time I saw so much lace and frills on a dress. The women talked and before long my mom handed me the dresses to carry out to the car. My mom was pleased with the quality and the price she paid so off we went to the shoe store. We looked at high heels nothing I knew anything about but my mom educated me once again. She bought two pairs of high heels in my size she advised. It all seemed so strange t o go shopping for women's clothing with my mom.
There was one final stop before we went home for dinner only this time I was blushing. You might think everything else would have made me blush and it did a little. We were inside an adult store with my mom showing me chastity devices and talking with the girl behind the counter. I was blushing while they talked size, style and effectiveness. My mom said that small one to the girl and we went to pay for it. On the way home my mom talked to me about all we bought and how it was close to what we saw in the parade. I asked her what about the chastity thing and how did she know about them. Well a couple of letters talked about them and while she was in a washroom at the parade my mom talked with a woman who had her own sissy.
So we arrived at home with my mom working on dinner she sent me to have a bath handing me a razor to shave myself. I asked what to shave and my mom told me everything except my head like the other sissies. It was getting real by now but I agreed to play my part so my mom could play hers. We had a deal and I wasn't going to let her down even though I wanted to a couple of times. My mom called to see if I wanted help so I let her in to check my shaving job. With a few spots I couldn't reach well my mom took care of them. Leaving the door open my mom went to get the chastity device and a bag of frozen peas which I didn't see at first. The shining device sat on the counter while my mom put the peas on my pubic area. Well frozen anything on my penis made it shrink and me jump. My mom smiled holding the peas on my penis and balls until I begged her to take it away. She gave me the device and I put it on changing the rings until finding the right size. My mom put the peas on my penis once again to make it shrivel before sliding the chastity device over my penis and locking it in place. I looked down to see not much of a penis locked behind stainless steel. My mom laughed telling me she thought it was cute. My mom asked me if I was all ready to be her sissymaid and I said I thought so.
We went to the living room where I saw everything we bought over the week. I didn't have to do anything while my mom started to dress me from top to bottom. It all felt very odd from panties to stockings and bra to heels. Before long I was all dressed in a pink lace covered sissy dress trying to stand in high heels for the very first time. My mom looked me over telling me how sweet I looked and hinting I be in the parade next year. We went to have dinner with me having troubles with my new high heels. For the rest of the night we talked about what I was wearing and how it would play a part in who I was becoming. Little did I know to be a sissymaid it wasn't just about clothes. My mom taught me to call her Mistress and as the next few days passed I learned more about what a Mistress expects from her virgin sissymaid. My mom made sure I only wore my new clothes and nothing else from my previous life. At night I slept in baby doll nighties and by day I wore only sissy dresses.
After the first week my walking in heels got better and so did my understanding of what it was like to be my mom's sissymaid. My mom started to experiment with her role as my Mistress wearing black skirts and high heels around the house. Once in a while she would slap me with her walking stick to let me know she was my Mistress. The other night while we had dinner I thought it was time to let my Mistress know I had fulfilled my side of the deal and wanted to take a break from sissymaid life. It was then I learned my mom had become a real Mistress. She looked at me laughing telling me there was no break as her sissymaid. I thought she was kidding a little but I was wrong. My Mistress had been reading and talking to other Mistresses about training a son to be her sissymaid.
I knew then I was going to spend a long time as her sissymaid after reading about other who had the same fate. My Mistress agreed to be fair to me and not take advantage of me like some we read about as long as I agreed to be her sissymaid and do what she demanded. What choice did I have I thought to myself shaking my head yes to her. Mistress pointed out we made a deal before starting I would be her sissymaid and she be my Mistress. I remembered that conversation and remembered how we both agreed without any pushing each other into it. Having said that I learned how quickly my mom became a Mistress. I spend my days looking after the cleaning and laundry while learning to cook and sew for my Mistress. She on the other hand spends more time with her girlfriends and shopping for me lately.
Auntie Helga when I first read some of the letters on your website I didn't think they were true. It didn't make sense to me mothers or wives would turn their men into sissymaids and the men and boys liked it. When my mom and I went to the Pride parade it started to make more sense. I thought it was boys and men wanting to be sissymaids which puzzled me. Then after actually seeing them in a parade I realized some liked it and some were there because of strong women like their mothers or wives.
In my case my mom is thrilled I am her sissymaid more than I am. My mom is so much happier with me and life in general even when we had a great relationship before the Pride parade. I mean if we weren't so close why would a mother and son go to a Pride parade. My mom continues to show me her dominant side and we talk about our roles every day. One thing my mom demanded was me not asking about making changes, take off the chastity device or ending my life as her sissymaid. She made it quite clear I am her sissymaid period and will continue to be until she decides otherwise. After hearing my mom show me who is really the boss I have accepted her position as Mistress and mine as sissymaid.
Thank you for having such a great website help sissymaids like me understand our roles in life.
Thank you for your letter Sissymaid Allison. Your natural curiosity about sissies tells me that you are at heart a sissy and personally, I love sissies, it would seem your mother does as well, lucky for you. The Pride Parades are perfect for opening minds and showing people that it is okay to express yourself, I am so happy for you both that you have this opportunity to share something truly unique.
I am very encouraged to hear how well your mom has taken to her new role as your Mistress, she obviously has given this a great deal of thought. You serving her is going to make her life so much easier, giving her more free time to do as pleases. I love her choice of wardrobe, keep in mind that this is as much about her as it is you and will change her as well.