Dear Auntie Helga,
I am not sure where to start here telling you about my situation so bear with me while I jump around. My wife and I have been married for 22 years and for the most part have a great relationship. She spends some her time reading novels and now stories on the internet. One of the websites she visits often is yours as I found out months ago. It is no secret that she reads about sissymaids as she seems to enjoy the stories. I started to read some of the letters at times when my wife wasn't home. What I noticed was her taking notes about what she read which lead me to believe she was making plans.
My wife included items like maid uniform, pink sissy dress, bras, pink panties, heels, garter, stockings and so on. It was clear when I read the note under the keyboard she was making plans as I mentioned. I have never worn women's clothes of any kind and had no idea about them. What I did was send an email to a few stores just to see if anyone would answer me. Out of all the stores one lady did get back to me with information about helping crossdresser and sissymaids. I called her to talk about what my wife was planning to do and I might need some help.
Gail was her name, she talked to me about a few suggestions and agreed to help me with sizing if I would come to see her after the store closed. My wife goes out with the girls once a week so I picked the same night to go see Gail. All I knew was what I read on your website Auntie Helga and what notes my wife kept. I had also talked online to a women who makes and sells sissy dresses and knew she would need my measurements hoping Gail would help me in that area.
I went to see Gail feeling rather nervous and relieved that a woman was willing to help me before my wife surprised me in the near future. Gail was a nice older woman who showed me the type of bra she had in mind, panties, garters and girdles. Gail asked me to take off my shirt to try a few bras on for style and size which I did with a red face. She found the size and style then we looked at panties picking out I think they were called full briefs. Gail took measurements and gave me a couple of girdles to try on which I did .
Gail looked at both and decided on a panty girdle with garters for stockings. All the time we talked about what I thought my wife would like me to wear and how often. Gail told me most sissymaids need 3 or 4 bras, a dozen pairs of pink panties, a girdle or maybe 2, silicone breasts. 6 pairs of stockings, 2 sissy dresses and 2 maid uniforms. She was very good about telling me what my wife would probably want for me to get started. I mentioned needing measurements for the woman to make the sissy dresses which Gail gladly did for me.
By the time I was finished I spent $750.00 that also included the breast forms she ordered for me. Gail told me where to buy the uniforms, high heels and chastity device. I had time to buy the uniforms and chastity device which Gail recommended. The next day after work I went to buy a pair of high heels at a store that sells larger sizes. The woman at the small store asked me if Gail sent me when I admitted yes. She took me to the back so we had some privacy while I tried on a few pairs of high heels.
I was having troubles standing in them making the woman smile at me trying. She asked me what color my uniforms and sissy dresses were to help pick the right color for the high heels. With her recommendation I bought 2 pair so I would have the right color for each dress. The next night while my wife was working late I tried on my purchases thinking to myself how strange I felt not only wearing the stuff but looking at myself too.
It was a week later that Gail called for me to pick up the silicone breasts. She gave me a bra to try on, made sure the breasts fit the bras she already sold me and told me how to look after the breasts. Gail asked me if I was able to purchase everything she mentioned and I confirmed I had it all and was waiting for the sissy dresses to be made. She complimented me on getting it all done by myself.
Gail asked me when I was going to do my reveal when I laughed at that term. I was going to wait for the sissy dresses but she suggested I not wait for them. She thought it was a better idea to get started and have the sissy dresses as a surprise for my wife to show her my devotion. Gail also pointed out after seeing me without a shirt and pants to shave myself like all sissymaids end up doing. Gail explained shaving all of myself would show my wife I was ready to be her sissymaid instead of looking like a man under the pretty clothes. She told me that the chastity device I bought would also look so much nicer with everything clean shaven.
I waited until today with the weekend ahead before shaving myself since my wife would notice that right away. Earlier I called Gail to let her know I shaved like she suggested but I wasn't sure what to do next. She told me since shaving my wife was going to see me tonight so there was no more hiding the obvious. Gail told me to put the chastity on, put one key in an envelope and the other on one of my wife's gold chains. She also told me to get dressed and be ready for when my wife comes home.
I did everything Gail told me to do knowing it was what my wife wanted from me. Looking at her note again I saw she added chastity to it which confirmed with me my wife was in fact planning to have me as her sissymaid. I called Gail again since she wanted to hear from me after I got all dressed. She asked me how I felt and then suggested I practice walking in high heels before my wife got home. Gail told me it would look bad if I couldn't walk without holding the walls.
Gail suggested I prepare a few words to say to my wife when she got home because she would be surprised and maybe shocked at the same time. I was planning on letter her know how much I love her and how I wanted to worship her just like the sissymaids she has been reading about for so long. Gail also felt I should practice a curtsy and getting down on my knees and standing again without falling over.
Finally she told me to present my wife with the keys to the chastity device then lift my uniform enough to show her that chastity was already in place. Gail told me to drop by and see her from time to time and buy something for myself and my wife as a reward for her time helping me. I agreed to let my wife know how much she helped and suggest we shop there from now on.
Auntie Helga I am not sure if I am doing it all the right way having only read letters and talked to Gail who was a stranger to me not long ago. I have a few hours to get used to my appearance before my wife comes home. I am hoping this is what she wanted based on her interest in your website and the note pad I found. If not oh well I guess I own the clothes in case she changes her mind some day.
When my wife walked through the door I was standing there to greet her. Without thinking I dropped to my knees kissing her hand and got up again. She looked at me surprised as hell by asking what was going on. My heart dropped with me thinking did I misread her surfing habits and noted items. In my defense I admitted reading letters about petticoating and finding her note by accident.
I went into some detail about sending an email to a few women's store and getting a reply from Gail. It took a while to explain it all but my wife patiently listened to me. When I was finished I gave her an envelope and necklace with the key to my chastity device. She asked me to put the necklace on her which I did. She wanted to see the chastity so I lifted my dress showing the chastity bulging through my girdle.
My wife looked me up and down admiring my shopping skills which were Gail's not mine. I asked her is she wanted me to be her sissymaid or was it just a fantasy of hers. Smiling back at me she admitted wanting me to be her sissymaid for a while but wasn't sure when to tell me. I asked her if she was happy with my purchases just to be sure I didn't buy something she didn't want me to wear. The only thing she never thought of was my girdle which is when I let her know it was Gail's idea.
I showed my wife the other items I bought which made her happy. We talked for hours about what she had in mind for me outlining clothing to maid duties. I let her know two sissy dresses were ordered which again made her happy since she wanted me to wear sissy dresses more than maid uniforms. My wife also made it clear to me I was going to be her sissymaid full-time except family events or other times she would advise me of as needed.
I thought it would be the case after reading letters about other Mistresses and sissymaids. She did tell me she was very proud of me for taking this on without her involvement. It was her note that told me about her plan. My wife grabbed my locked away penis telling me to enjoy wearing my new chastity device since it was going to be there for a while as she smiled at me.
When we went to bed I took out one of the nightie I bought which again made my wife smile. She approved telling me no more PJs for me. My wife was turned on by it all so she ended up sitting on my face until I made her cum. Then it was off to sleep for both of us. This morning she wanted to see me coming out of the shower wearing nothing but my chastity device. She watched me get dressed into my maid uniform smiling all the while.
My wife decided to go in later to the office and spend time showing me things she wanted done. She left a few minutes ago so I wanted to let you know what happened. I am in shock of how things went down but happy that my wife was pleased to see me as her sissymaid. I am sure I have lots to learn so if you have nay tips for me please share.
Thank you for your letter Mitch. You did the right thing, you are a loving and caring husband that wants only for his wife to be happy, you saw an opportunity to do something she showed an interest in and followed through. Your efforts have turned out wonderfully and I'm sure you will make a perfect sissymaid. The main thing required of a sissymaid is obedience, do as you're told, smile and be pretty.