Dear Auntie Helga,
My grandmother asked me if I wanted to go out for an early dinner then go shopping with her so I was all over going out to eat. At dinner we were talking about lots of things when she asked me about the sissymaid thing again. My grandmother is a bit old fashioned so when I show her stuff on the computer it is like from another world to her and it takes a while for her to digest it. I also think she likes protecting me from making a mistake from not really knowing what I want to do. My grandmother was trying to get an idea based on what we talked about and the thought of me wearing women's stuff.
So we went shopping with my grandmother taking me right into the women's section to look at dresses and skirts. We were talking about what I might wear to be a sissymaid without finding what my grandmother had in mind. Then we went to look at women's undies and bras with me picking out what I thought would be best for me not having any experience. I was focusing on looks and my grandmother educated me on the types of bras and what she knew would work best. She took me to the change room to try on a few bras but I was too chicken to go in with other women there. My grandmother reminded me she wanted me to do most of the shopping so picked 2 bras and 5 panties and a slip and pantyhose then head to the cash. She told me I did good for a first time buying women's stuff.
Next we went to the shoe store to look for shoes for a sissymaid but they didn't really sell sissymaid shoes there. Once again I picked out a couple of pairs with my grandmother picking out a couple too. I sat down and tried the shoes on where people didn't notice me. I bought a pair of high heel shoes higher than my grandmother wears. We loaded up the car with my grandmother asking me how I felt about what we bought. On the way home she made a turn we don't normally take so I asked her where we were going. She knew but wanted to make it a surprise. We parked in a parking lot with me still not knowing where we were going with grandmother talking to me about our challenge finding a dress.
She asked me again why I wanted to be a sissymaid and how close was a sissymaid to a regular maid. In my own words I went on to tell her they are similar with a sissymaid doing more for one person not like a maid does for lots of people. My grandmother opened the door and we went in this store that sold working clothes for men and women. She asked the lady in the store where the uniforms were and we went there to look at all kinds of uniforms for women and men but we looked at women's. My grandmother said to me if I was going to be a sissymaid I should wear a sissy dress or a maid uniform before anything else we looked at earlier. She told me many of the dresses we looked at were not good to work in but the maid uniform was designed for that purpose.
The lady in the store came to help so my grandmother talked to her about the maid uniforms. I heard my grandmother ask if I could try on a couple for size before buying. The lady smiled at me saying sure no problem and took me and a few uniforms to the change room. My grandmother told me to try each one on and let her know which one fit the best before taking it off. I was shaking from being nervous as I could hear them talking not far from me. The lady in the store asked me if I was making out alright and I said yes.
When I found the uniform that fit the best I called my grandmother to look and opened the door for her. The store lady was there too and I was blushing red but my grandmother was good about making me feel comfortable as they both looked at how the uniform fit me. I bought 2 of the uniforms in a pale blue shade paying for them with my own money and dealing with the same sales lady as grandmother waited at the door.
On the way home grandmother talked to me about her understanding of sissymaids based on what I told her and what we looked at on the computer. She pointed to my legs as I was wearing shorts and she saw my legs in the store with the uniform on. Grandmother asked what I thought of shaving my legs before trying on my new outfit. I was kind of blushing again when she let me know it was the right thing to do if I was going to be a sissymaid or any maid for that matter. I went to shave my legs like she suggested then grandmother helped me try on my outfits. I had never worn panties or bra or pantyhose or even a dress or high heels before. My grandmother didn't watch me put my panties on but she did help with the rest showing me how to put on pantyhose and a bra and the uniform after the slip. When I was done she asked me if it was what I wanted and did everything fit alright. I had no idea what to look for so she looked me over make a few adjustments to my bra straps and slip straps. She sent me to look in the mirror in her room with me walking in high heels for the first time. I came back laughing at myself seeing me in a maid uniform for the first time. Grandmother asked me if was laughing at myself and I admitted I was so she laughed too.
I asked my grandmother if she was alright with me dressed this way and she admitted it was a different side of me but nothing to worry about as long as I was happy with her help tonight. We talked for a while as I got used to my new outfit and my grandmother seeing me in it. She went on to ask about what I envisioned myself doing as a sissymaid. I thought about it and talked about learning to be her maid which she said would be wonderful. I wanted her to teach me how she did the cleaning, laundry, ironing and cooking. My grandmother was clapping her hands with joy I wanted to be her maid. I thought she was confusing sissymaid with crossdresser before. Now she knows I want her to teach me how to be her maid so she can relax more.
She asked me where to buy the sissy dresses because she didn't know of a place. We looked on ebay and your website store too Auntie Helga with my grandmother liking several of them. She made me laugh letting me know she wouldn't wear a sissy dress but she was willing to buy me a couple. I asked her if she wanted me to wear sissy dresses for her or just my new maid uniforms. She was starting to figure it all out as I could see by her expression.
Grandmother thought it would be best I had both kinds of dresses if I was going to be a sissymaid I would need to have lots of dresses. I read grandmother a couple of stories and letters out loud pausing when she had questions or remarks. By bedtime she had a much better idea of what a sissymaid does for their Mistress. We didn't buy any nighties because my grandmother didn't realize I needed to wear them so she gave me one of her nightgowns to wear to bed. When she saw me wearing it she said I could keep that one as she liked it on me better than her. It was a two piece set so she gave me both parts.
I'm sorry for writing a book here Auntie Helga and maybe I got carried away in excitement.
Thank you for your letter Colin. How nice to hear from you and I am so pleased to hear that you are such a loving grandson. Really I see no problems with you becoming her sissymaid, you seem to want to be a sissy and that's great, and you wish to serve the woman that means the most to you.