Dear Auntie Helga,
In the past my mom offered me stuff before when I always said no thanks right and then I talked to my mom about me as a sissymaid. Here is the way I talked about it...
When she went to get changed like she does most nights at 9:30 I called her and she said she was in the bedroom. I walked in like normal while she was putting on her robe and without thinking too much I asked to try one on. She looked at me saying sure and which one opening her drawer. I picked the one I like but when I went to put it on my mom said I had to take my other clothes off and not wear it over clothes.
My mom said the material is best felt on bare skin not with clothes under it. When I took my clothes off my mom asked if i wanted panties too or just the nightie. I was turning red but I took a pair of panties. My mom told me they looked nice on me and she saw I liked them too because my penis was getting hard. My mom told me it was normal then she asked if I wanted to try on a bra too. I didn't answer but she picked one and put it on me.
We watched TV next when my mom asked how I liked her nightie and panties. I said they were nice and she said, see I told you. My mom wanted to know why I changed my mind all of a sudden. I thought it was okay to tell her about reading on the internet. I wanted to know if my mom heard of sissymaids before. She laughed letting me know of course, why did I want to be a sissymaid.
Auntie Helga I was without words with my mom taking my hand letting me know it was fine if I wanted to be one. She told me like you did Auntie lots of boys and even men are sissymaids for moms and wives. My mom wanted me to tell her about what I wanted to do and what to wear so I did. She was excited to hear me say sissy dress, high heels and panties. I talked with my mom for over an hour sitting in her nightie.
I showed her your website Auntie Helga and she was surprised I found it. I showed my mom a sissy dress I liked and she liked it too. Then my mom talked to me about the hard work to be a sissymaid not just looking pretty. I wanted to know if she was going to show me and help me. She said yes if I wanted to be a sissymaid she would help me. My mom asked me questions about sissymaids and told me no playing with my penis since it is not allowed for sissymaids. I read about it but my mom said it was true no penis play.
My mom said only if I am good and only when she permits it. I didn't care about my penis just to be a sissymaid. We went to my mom's bedroom where she picked out some things for me to take to my room. She gave me some of her old panties, 2 bras and another nightgown she did like anymore. My mom said she would shop for me but wanted to measure me first so I let her measure me all. My mom said I can start helping her tomorrow after school.
I am going to sleep now Auntie. Thanks for helping me talk with my mom.
Thank you for your letter Jordan. I am so happy for you, I know you have fantasized about this for a long long time. Her acceptance was obvious, giving you her clothes, I know how special it must have felt to be wearing the panties she had worn.
Okay, now it begins for real and there is much to discuss from teaching you the proper way to do actual housework to taking care of your mom. I am not surprised she had heard of sissymaids, its is becoming much more common now, also that she insisted on no masturbation, that will help you to concentrate on serving her.