Dear Auntie Helga,
My name is Tom and I live with my stepmom. We have lived together since I was 5 however when I was 14 my dad passed away. It was a hard time but thanks to my stepmom for keeping me together. She is not only a beautiful woman but the only mom I ever knew and I love her so much. Life with my stepmom was sometimes better than when my dad was alive only because he used to yell at me. My stepmom has never yelled at me because she showed me other ways to get what she wanted me do.
You are probably wondering why I have your email address so best I get on with it. As I said my stepmom is beautiful and I loved looking at her when she wasn't paying attention. I started to look at other moms on the internet and that led me to moms who kept their sons as servant boys. It made me think if only my stepmom would make me her servant. I looked at servant boys, then sissies and finally sissymaids on your website. I liked it very much except I had no idea if my stepmom would say yes or get angry at me.
Not long ago I held on long enough not letting my stepmom know what I was looking at and thinking of her at the same time. One night we were joking around watching a movie when I asked her if she ever wanted a servant in her life. She looked at me wondering what I was getting at first then she answered what kind of servant did I mean. I went on to let her know someone to help her with dressing, bathing and anything personal. She laughed telling me that would be a dream and then have the person clean her house and do the laundry too. My stepmom asked me where did that kind of question come from and had I seen something on the computer. In a typical son answer I replied 'kind of mom'. She wanted me to spit it out so I shared more.
I went to my computer to show my stepmom some moms with their boys helping brush their hair, dress them and a couple bathing their moms. My stepmom didn't think it was real at first but she kept looking and reading. We went back to watch TV when my stepmom asked me to tell her more about this servant thing and why my interest in it. It was hard for me to explain something inside of me wanted me to look into it more. When I did look into it the whole idea grew on me. My stepmom asked me if I thought she would let me be her servant and why would she allow it. I could tell my stepmom was not angry but curious about my thought process. I let my stepmom know she was a beautiful woman and I always had a crush on her so I wanted to serve her as my queen. My stepmom looked at me wondering if she heard me correctly.
My stepmom described what she thought she heard along with what she saw on my computer to me. It started something like I wanted to be my stepmom's servant so I would bath her, dress her, do her hair, shave her legs and anything else she wanted of me. By that time I was blushing but I said I thought so or at least dreamed about it someday. My stepmom asked if there was any sex in my dreams. I said no sex just serving you in all ways. My stepmom asked me if I ever saw her with no clothes on without her knowing but I said no. She asked me what kind of clothes did I see myself wearing as a servant. In some of the pictures the boys only wore aprons and underwear and in others they wore maid and sissy dresses. To answer my stepmom I said it was up to her if she approved of me as her servant.
My stepmom started to play along with me in a way. She suggested I be her servant and maid together and wear a maid uniform. Then she thought an apron for bathing her would be a must. My stepmom looked the computer again pointing out a man in a sissy dress in heels. I got nervous with my stepmom as she took over the conversation more than I expected. My stepmom laughed letting me know she could see I was scared of what she talked about. I had to admit being scared and surprised she picked up on it so fast. My stepmom looked at me after scaring me with an okay. I was shocked that my stepmom, my best friend said okay, okay to what though. I asked my stepmom what did okay mean. She said to me if I wanted to be her servant I also had to be her maid okay? I asked if that meant I had to dress like a maid too and my stepmom said of course or no deal. My stepmom said to me like maid not a sissy. My heart missed a beat because I was scared for her to tell me sissy dress more than anything.
My stepmom said we couldn't start until she went out to buy me an appropriate maid uniform and all the little things I would have to wear under it. She looked over at me then asked if it was what I wanted or had she missed something. I replied I wanted so much to be her servant and not so much her maid but okay I would do it if she showed me how. My stepmom gave me a big hug then told me we were going to have so much fun.
A couple of days went by as my stepmom brought home bags every day but told me not to look in them. Then on Saturday morning my stepmom told me to get showered. Part way through my shower my stepmom came in with a couple of razors for me to shave my legs and underarms. I was shocked but she insisted her maid not be a hairy one so I did what she told me. Not thinking anything of my stepmom still hanging around I walked into my room where she stood. The feeling I had of total embarrassment standing there with no leg hair and smooth underarms. She inspected then told me she was ready to get started and had purchased my maid attire. Within minutes my stepmom had me completely dressed like a female maid. I never wore panties, a bra, pantyhose, a dress or uniform never mind high heels. My stepmom explained what I she bought and how I was to wear it every day or at least during the day.
That was it as I started to be my stepmom's maid right then and there. I helped her out of her work clothes when she came home and into something casual. At night I bathed my stepmom and shaved her legs, underarms and vagina. She taught me how to do her hair and makeup which took weeks for me to learn. While at work I looked after the laundry, cleaning and all the ironing. I started dinner every day under my stepmom taught me to do it all by myself.
Unfortunately for me my stepmom had to put me in chastity since she didn't like seeing my erection every night when I bathed her. I didn't like it at first but my stepmom told me it was there for a good reason and she allowed me out of chastity on Sundays all day until her bath time. I had to put the chastity device back on and give my stepmom the key before bath time.
On Sundays we always went out for dinner which still remains the same today. It is the only day I don't have to be her maid but I still have to wear panties. My stepmom noticed once I tried to give her a hard time and not get dressed in my maid uniform, Since then as long as I am in panties every day it is easy for me to get dressed in my maid uniform. My stepmom told me panties are magical for boys.
My relationship with my stepmom has only gotten better as though this was meant to be for both of us. I love my stepmom more than anyone as she taught me more about making a mother happy or any other woman for that matter.
Thank you for your letter Tom. As I have noted many times the only way to realize your goals, especially if that involves another person, is an honest conversation and your case is a perfect example. I must say how thrilled I am for you and your stepmom to have taken this opportunity for you to serve as her maid. It seems to have turned out far better than you could have hoped.