Dear Auntie Helga,
My name is Tommy a 19 year old who lives with his mother, a single parent. When I was younger I used help my mother fold the laundry and I was always interested in her lingerie. It was so pretty and soft and smelled nice that it was my favorite part of helping with the laundry. One day when I was around 15 years old I started to ask my mother about her pretty lingerie so being a mother she gave me the answers to my questions. Without thinking or being caught up in the moment I asked her if I could try something on to see what it felt like. Mother looked at me thinking I was kidding so she asked if I was kidding. By then I was blushing which she noticed then said okay what did I want to try on.
Blushing as I was I asked for this particular nightgown so mother asked if why I liked that one as she passed it to me. I was about to put it on when mother said that I should take my clothes off to feel how nice it is on my skin. She helped me leaving my underpants on then she put the nightgown over my head with a smile and a laugh. She said it looked cute on me so again without thinking I agreed. Mother let me leave it on while we folded the rest of the laundry. She asked for her nightgown back helping me take it off.
Nothing was said until laundry day the next week when I asked if I could try something again. Mother looked at me, thought for a minute then said okay Tommy. Mother let me pick out a different nightgown and a pair of panties this time. I took my clothes off leaving my underpants when mother stopped me telling me underpants should come off too. I put on her panties and nightgown continuing to help her fold the laundry. This time mother asked me why I like her lingerie but I didn't know I just did. Mother asked me if there was anything else I wanted to try on but I was too embarrassed to answer her.
She asked me to wait there while she went looking in her closet and drawers coming back with a bra some stockings and shoes. Mother asked me to take off the nightgown so she could put her bra on me. She made a few adjustments then slipped the stockings on me but they would stay up until she came back with a garter belt. Mother looked at me thinking then asked me if I wanted to try on a dress that she didn't wear anymore. It was too big for me but not by much since mother is a petite woman. She put the shoes on me that were a high heel. Mother looked at me asking what did I think? She asked if I liked wearing her clothes or just nightgowns. I was blushing so she said it was alright to be honest as she wasn't going to tell anyone or laugh.
Mother talked to me about trying on her clothes and wanted to know if I wanted to keep them on for the rest of the day. I replied yes without even thinking, so she agreed. That was the beginning of mother allowing me dress in women's clothes with her buying me my own in the right sizes. I didn't wear them all the time even though I wanted to. As a boy I went through cycles of getting in trouble at school so mother would ground me and forbid me to dress. In fact mother stopped me from dressing for over a year.
Then one day to my surprise she told me to take a bubble bath which I enjoyed. Mother came in to the bathroom to share the bath with me which she had not done for years. She shave her legs and underarms then handed the razor to me to do the same. I paused not sure if she was kidding but she insisted so I did it while she watched and relaxed. When I was finished mother told me to stand so she could get the areas I missed. I didn't have much hair on my chest or any on my back so mother rinsed me off then I got out to dry myself. There was no conversation yet about why I was asked to do this which had me confused. Mother told me to put on my blue nightgown then go watch TV while she got dried off.
When mother joined me I asked what was going on with a smile as I was happy inside to wear my nightgown again. Mother explained that me being allowed to dress with the clothes she bought me was always a treat that I didn't deserve last year. She knew that by taking away my clothes it was punishing me. Mother has decided to allow me to dress again and with it being the summer holidays she wanted me only wear my special clothes as she called them. She explained that it was time for me to learn that clothes are not the thing that make a woman. Mother explained she wanted to teach me how to do more than fold laundry if I would do that for her.
All I could think about was having the opportunity to wear my clothes again so I agreed. Slowly mother taught me how to do the laundry and cook and even iron the clothes. Then a few weeks ago mother said that she wanted me to become her sissymaid which I didn't know much about. We started to look at websites with sissy stories then branching out to femdom which was scaring me. Then mother went to the petticoated website showing me pictures, dressed and letters from people. The more I read the more it scared me to be a sissymaid for my mother.
She said it wouldn't be much different than what I was already doing except more personal services like bathing, dressing, her hair and nails and some very personal type services. I asked her why would she want me to be a sissymaid and wear a maid dress. Mother let me know that she felt I was born to serve and she felt I was old enough to get started. Mother doesn't know I am writing to you Auntie Helga not that I am hiding it from her. I will let her know if I get answer back from you though. I do agree that my mother could use some help around the house just not sure I need to be a sissymaid to do it.
Auntie Helga can you tell me if this is a normal request for a mother to ask her son? Is this common or is mother dreaming? Mother and I have been so close over the years having each other with no father in the picture. Is this my fault for asking to wear her nightgown years ago? I am not going anywhere as I love my mother with all my heart just not in a sissymaid kind of way if that makes sense. Performing a sexual act on my mother isn't something I ever dreamed of Auntie Helga. She is a beautiful women with a lovely figure but I am her son.
Thank you for your letter Tommy and for writing with your concerns as well as providing the very helpful background information. I understand your anxiety and would ask in return why wouldn't you want to do this for her? There is no 'fault' not yours or at all, this is a common progression from your natural curiosity and answered by a loving mother, you don't really need to think of it in those terms, its more complicated than that. Once you become her sissymaid she will become your Mistress and taking your relationship to a whole new level, as the readers would agree, you should give it a try.