Dear Auntie Helga,
When Donna walked through the door with me on my knees wearing a pair of her pink panties she squealed with joy giving me a huge hug and kiss. She asked me what made me decide all of a sudden which I explained has been on my mind for a long time but I was chicken. I also let Donna know that Auntie Helga helped me make the right decision. Donna took my hand down in the basement to crawl space pointing at 2 boxes that said Christmas on them. I would have never looked in those boxes and Donna knew it. I took the boxes upstairs then have Donna a few minutes to organize the contents. A few minutes later I heard ready Sandy so I went in still wearing her pink panties. She took her panties back then pulled out what I feared the most was a stainless chastity device that looked like a cage. Donna slipped it over my penis packing my penis into it then locked it. I asked how did she know the size when she said she measured me in my sleep months ago.
Donna looked at me telling me before I ask the device is on for a month as of today. I asked why a month when she told me to shut up then called me sissy. Donna passed me a pair of pink panties with lace around the waist and leg openings while putting the rest in my drawer and tossing my boxers on the floor.
Donna held up the bras telling me they were my new bras tossing me one to put on. I had never worn a bra before which is when Donna stepped in to help. She passed me these what I thought were large silicone breast forms telling me I like big ones so now I have a pair.
Donna showed me an open bottom girdle and a panty girdle both with garters ordering me to put on one. I couldn't understand why women would wear girdles, now I do, they suck it all in. Donna passed me some stockings putting the rest in my drawer. She has to show me how to put them on and hook the stockings.
Donna pulled out a pink lace covered sissy dress then passed me a white slip to put on first. She adjusted the straps and fixed my breast forms as I didn't have nipples lined up right. Over my head went the sissy dress with Donna pulling and adjusting it before zipping it up. I heard a click as she locked the dress on me. I wasn't going anywhere but decided to shut up and let her do her thing.
Donna passed me a pair of pink high heels and suggested I sit in the bed to put them on which I did. I asked how high were the heels on them when she smiled only 4" Sandy. Thinking Donna was finished, silly me she pulled out a shoulder length curly brown wig almost the same color as my own hair. Donna brushed it out then on it went on my head.
She ordered me to stand up and turn around so she could look at me. All I heard was perfect, love it. Donna showed me everything else including my new nightgowns, slippers, another pair of high heels, and some other odds and ends.
Donna stood back asking how I left with a loud Finally. I admitted it felt much different than I thought and maybe some of that was the loss of hair on my legs and chest. Donna hung the other 3 sissy dresses in the closet removing my other clothes. She took my hand as we walked into the office.
Donna pulled out the contract she got from the internet 6 months ago then started checking off some of the boxes. I had never read it in detail before now so we went over it with me initialing along the way. The contract basically said I was Mistress Donna sissymaid now and forever more with no end date to the contract. I agreed to do everything laid out on the contract including signing over the cars, house and bank accounts except my own account.
I also agreed to donate all my old clothes and to live in my sissymaid clothes or anything else Donna bought for me. That was the hard part but it was sign or stay in chastity for a year. I agreed to allow Donna to feminize me in any ways she chose including surgeries. I didn't want to sign that part but she told me it was standard on all contracts and probably wouldn't be used unless I wanted to do it for her.
Donna took my wallet and all credit cards then put my id and some cash into a purse that she called mine. I signed the contract with Donna making a copy then slipping it into a frame. It was like she had planned all this 6 months ago and now I see why she was angry when I wimped out on her.
We sat in the office for a while talking about why she wanted me to be her sissymaid 6 months ago and that the reason only got stronger. She did tell me I looked pretty in pink as she figured I would. Donna walked me through her idea of a sissymaid that did not involve disrespect and humiliation unless it was necessary to get me to listen to her.
Donna showed me a strap that she was going to keep handy hoping I would not give her a reason to use it on my bare ass. She went on to tell me that I had 6 months to prepare so there had better not be anymore excuses now. Donna told me she had time to teach me to cook but cleaning and laundry duties were going to be taught by a friend of hers who is a professional maid. My mouth was open thinking I am dressed like this and going to be trained by a real maid.
Donna told me her name is Lucy and I can expect her call before Monday and the training last at least a week. That being said I was expected to get up, get dressed and make breakfast every morning to get me into a routine. Donna gave me a hug and kiss letting me know she wanted this for a long time and that if I applied myself I would learn to enjoy it. I asked what about when her mother drops by with Donna looking at me wondering was that a question.
Donna told me as of now I was to be a full time sissymaid and that is what it meant, full time. She smiled at me letting me know if it made me feel any better her mom, sisters and girlfriends have known for months I was going to be her sissymaid.
Donna left to do some shopping giving me permission to write this email while getting used to my new outfit. All I know Auntie Helga is I am in for a wild ride now. At least Donna loves me very much not like a Dominatrix who just wants to beat me all day. I am going to try hard to make her happy so she knows this wasn't all for nothing. It was her dream far more than mine but now it is here my job begins.
Thank you for your letter Sandy. I am so delighted to hear your decision and I feel that this really is the best way forward for both of you. Best of luck in your sign of devotion and acceptance and so long as you are obedient you will do fine. I know our readers and I would love an update at some point.