MOTHER TRAINED ME TO BE HER SISSYMAID
from Christine

Dear Auntie Helga,

Here is my story of how my mother trained me to be her sissymaid. It began over a year ago where I had this urge to be a maid. I had seen pictures on the internet and for some unknown reason I wanted to be a maid. At that time I only saw pictures of men as housekeepers and traditional type maids. I wasn't aware of sissymaids or at least as a term. Anyways, I went to my mother with my thoughts of being her maid. She laughed at the idea I wanted to be a maid for anyone knowing it would be hard work. My mother wanted to know more about where I heard about men as maids so I showed her the website. Once again she laughed at the thought of men dressed as maids however she felt it was a good idea. We talked it over a few times before my mother agreed I could be her maid. Together we sat at the computer while my mother showed me the clothing items from panties to girdles. It was all new to me so I just listened and looked. In the end my mother decided if I was to be her maid I would look best in a commercial type maid uniform and not the French Maid costume type.

My mother took my measurements then made a deal with me. She would buy my lingerie since I had no clue about it and I would buy the uniforms and shoes. My mother found the stores I needed to go to and even called ahead to set things up for me, which I learned later. One morning before the stores opened I left the house to buy the list of items my mother gave me. I went to this store where they sold all kinds of uniforms. I looked around at first to get an idea where the maid uniforms were located. When I found them it was hard for me to look at the sizes without someone watching me. Well it wasn't long before a woman walked over to me to help me. She asked if I was Chris which startled me so I said yes. She explained my mother called to let her know I was on my way to buy three maid uniforms. I turned red just hearing the woman say that to me. Then she let me know it was no trouble at all as lately a few other men had bought maid uniforms from her. That made me feel better yet puzzled at the same time. It was long before I was finished shopping then headed home.

It was hours later that my mother came home with her purchases. My mother said to me I had better be sure I wanted to be her maid after all the shopping she did for me. My only reaction was I thought I did although all I had was pictures about it. My mother looked my uniforms with a smile on her face. She said it was fun shopping for me although she had to laugh a few times during the process. Then my mother showed me what she bought me. I couldn't believe all the stuff. My mother asked me to help her clear out some room in my drawers and closet. Then she picked out what I was to try on and we began. It wasn't long before I stood before my mother dressed as her maid. She had a good laugh as she helped me put the clothes on and when I was finished. Well that was the first day of my life as her maid.

As the days followed I learned how to get dressed on my own. My mother taught me how to apply makeup, shave myself from head toe and so on. She also taught me how to clean, cook, launder and iron our clothes. While I worked my mother learned more about boys and men as maids. She also learned about sissymaids well before me. I was happy to be my mother's maid although it was harder work than I thought. One day my mother talked with me about living as her maid fulltime. She meant getting rid of all my male clothes, growing out my hair and nails for starters. For me it was a big step to have a mother support my dream to be her maid but then she wanted me to really live as a maid. I always thought it was only clothes and if I wanted to stop it was easy. What my mother wanted me to do was live as her maid and no longer her son. It took a few conversations as I could see my mother was serious about it. When I agreed to do it she was so happy which made me feel good she was happy.

A few days later my mother showed me how to file my nails and paint them. She painted my toes as well. My mother showed me some hairstyles that would look good on me. While it took some time for my hair to grow my mother bought me a wig to wear in a style she liked. I never questioned my mother's taste since she knew more than me on what looked good. One Saturday morning before I got dressed my mother walked in my room. All I had on were my panties. She sat with me on the bed to let me know she bought something for me that was necessary to help me train as her maid. I was puzzled by the way she said it but I listened. My mother told me that most if not all male maids where something called a chastity device. With that she took it out of the bag to show me. I had never seen one before so I asked questions about it. I didn't ask why because I had gotten used to doing what my mother said. Within a few minutes my mother had slipped my penis into the device and it was locked in place. My mother explained the device was a training tool and she would take it off every few days to see how it worked. I had no idea what it was all about so I just wore it.

As the days and weeks went by my mother left the device on me for longer periods. The device bothered me in the mornings as it prevented me from getting an erection. Anyways I got used to it before long. Once day my mother told me it was time to get my hair done at her salon. She bought me a dress, skirt and a blouse for times outside the house. I was shocked that my mother wanted me to go out of the house dressed like a woman and go to a salon. We had not talked about that directly but my mother reminded me I agreed to live as her maid fulltime. She helped me get ready then off we went in the car. When we arrived at the salon I was terrified to get out of the car. My mother assured me everything was going to fine. Well a few hours later my hair was colored cut and styled. When the girl showed me in the mirror was floored at how I looked more feminine. My mother was so happy that I went along with her even though I had little choice.

As the weeks went by I learned how to look after my hair each day. I had mastered the maid life from my appearance to my duties. My mother wasn't finished with me. I began laser treatments so that there was no hair on my body anywhere. My mother was very good at explaining why it was necessary. About a month after all the laser treatments were done my mother talked to me about next steps. What possibly would next steps be as look at myself in the mirror. My mother talked to me about wearing breast forms and how it would be so much better if I had real breasts. One thing about breast forms that I didn't like was the moved around and I sweat wearing them. My mother told me that most maids get around to getting breast implants and she thought I would be happier with them. Somehow my mother had a way with making me believe what she recommended was always the best thing to do. I was terrified to be honest until I went with her to a clinic. The lady there was so professional and she had experience with men. Anyways by the time we left an appointment was made for me to get breast implants a week later. My mother assured me it was a good thing for me to do so I went through it for my mother. The first week at home was hard and painful but in time all that went away. My mother was right that having my own breasts turned out to be much better than wearing hot sticky breast forms. It took several weeks before I was able to get back to housework at least the bending over kind.

My mother took me to have a bra fitting after I was no longer required to wear a post-op bra. Once again I was embarrassed but the women at the shop were all professional and supportive. It shocked me to know that in general most women liked the thought of me as my mother's maid or maybe they thought I was transgender. We ended up leaving with a few pretty bras that I loved to wear. On our way home I thanked my mother for allowing me to be her maid and getting me breast implants. My mother asked me if I was happy as her maid. I was happy even though at times I was scared. We talked about all kinds of things that day one of which was me getting married some day. I knew I was going to be a maid fulltime more than ever after getting breasts.

My mother talked to me about how popular it was for men to surrender to their mothers and wives. The words my mother used were new to me so I listened. My mother told me I was well on my way to being a sissymaid and that she wanted to help me get there. My mother went into detail about total feminization and serving her before I get married. My mother told me that sissymaids are very much in demand and that I had no worries about meeting a lovely woman. Then she went on to tell me that there was a couple of things I had to do to prepare myself as her sissymaid and my future wife's sissymaid.

My mother was pleased with my progress as she loved that I was now a real sissymaid. My mother wanted me to meet a few women who expressed an interest in marrying a sissymaid. Without going into detail about the first one who was too dominant for me my mother introduced me to Helen. I spent a weekend with her then back home to my mother. Helen and my mother met a few times while I cleaned Helen's house. My mother wanted to be sure Helen was right for me and what I thought as well. I spent a week at Helen's and then a week at home with my mother. Last week now that I am current here Helen took me to try on bridal gowns which was once again embarrassing. We were the only customers there at the time with two ladies working in the shop. The owner told us that she fitted other guys in gowns before so not to worry or be nervous. She was however surprised when she saw my breasts. That changed the style of gowns she showed us to something that showed my breasts instead of a gown that showed no cleavage. We were there for a few hours by the time we headed home. Once home I was back in my uniform since Helen wanted me to know it was always a treat for me to wear a pretty dress or skirt out of the home. At home I was her sissymaid and needed to dress accordingly.

Auntie Helga, I wanted to thank you for all your support over the months. At times I was terrified to go down this path in life yet you continued to help me understand that it was the best thing for my mother and for me. Now I have Helen in my life who wants me to be her wife.

Thank you
Christine


Thank you for your letter Christine. What a wonderful story, thank you so much for sharing it with me and my readers. Along with the support of your loving mother, you became the maid of your dreams, so many men and boys have these desires, few get to fulfill them, you're proof it can and does happen.

Now you are well on your way, trained to be a proper sissymaid by the person best suited to do so, with her open mind and strong confident personality, your mother prepared you to be Mistress Helen's sissymaid husband. I know my readers would love an update at some point.

Auntie Helga

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