Dear Auntie Helga,
I was able to talk with my wife this evening about me in a maid uniform. She rolled her eyes with a smile like here we go again with my thing for maid uniforms.
As we talked about it I asked her for real would she allow me to buy and wear a maid uniform if I agreed to be her maid. Linda looked at me wondering when I was going to drop the punch line. I asked her before she answered would she be willing to look at a website where other men gave themselves to their wives in a type of maid role. Rolling her eyes again smiling still Linda agreed to have a look with me. We reviewed the Gallery so she could actually see I wasn't the only one but I didn't want to wear a French maid or sissymaid dress. When we were finished Linda remarked something like 'so you want to be my maid looking after the entire house'. I replied I was more interested in wearing a maid uniform but if she would allow me to then yes I was willing to have her teach me real maid type duties.
Linda went on to repeat what she read about cleaning, laundry, ironing, cooking, dusting and so on with me having to agree. The more we read the more Linda picked up on the sissymaid specifics. When Linda had enough she looked at me saying 'let's go for it and see how it works'. She started making a list asking me about what uniform so I showed her on a website. We looked at shoes, lingerie, wigs with Linda writing down some of what I picked out and some of what she wanted from reading. Linda went back to a story we were reading pointing out a strapon and chastity. I reminded her I wanted to be her maid so I didn't need those things. Linda came back to remind me the phrase 'what was in it for her' and she could always say no way was I going to wear a maid uniform. She pointed out giving me some slack by not wanting to see me in a sissy dress at least right now. Linda did her usual come on Rob do it for me routine causing me to give in as usual.
With both of us off on Wednesdays Linda grabbed her purse asking if I was going with her shopping. I asked her if she meant right then, the answer was did I want a maid uniform or not. We went shopping to buy me my maid uniform first which turned out to be two of them. Linda had my attention as we shopped with me wanting to try one of those uniforms on right away. We went from store to store picking up items from panties to shoes before stopping to buy me a chastity device, breast forms and her a strapon. I felt like hiding in the stag shop having my wife by me a chastity device asking questions about them and the same with strapons and breast forms. Linda didn't see why I was so embarrassed since lots of people buy those things, just not me. Linda was beginning to scare me with the sudden interest with me in a maid uniform. You know how women tease men about women's things? It was that kind of teasing. By the time we got home I was excited, scared, embarrassed and humiliated.
We carried the bags to the bedroom when Linda surprised me again sending me to shower and take off all the hair on me. I had to ask her twice to be sure I heard her correctly. Linda was very clear on her request as she read sissymaids were supposed to be feminine and not covered in hair. Once again I heard the 'oh come on Rob do it for her' as she offered to help me. It took forever to shave myself and I was not that hairy like some men. I finished and cleaned up all the hair before going back to the bedroom where Linda was waiting and smiling seeing me with no hair on my body including my penis. Linda got down on her knees with me thinking you know what but it wasn't going to happen. She slipped a metal ring over my penis tucking my testicles in and around it then the chastity device applying lubricant to this tube and inserting a tube in my penis with a cage covering it. Linda took some time to get all of my penis in the cage before locking it tight. She looked up at me smiling letting me know it was Linda approved a joke we often said at home. Once that was done I started putting on the items we bought slowly getting closer to the maid uniform. It was always a fantasy or mine to wear a maid uniform and it was about to happen.
Linda started to laugh at how excited I was wearing a maid uniform almost like I won the lottery. I felt so amazing not even thinking about the bra, panties, stocking and heels. It was all about the maid uniform to me. Linda put this wig on my head of hers smiling at me even more. She asked me was it everything I always dreamed or was I disappointed with the end result. I thanked Linda for helping me live my dream and she thanked me for offering to fill one of her dreams calling me her new maid. That one hit home with the way she looked at me when it came out of her mouth. Linda told me to show her my walk with her laughing and offering to teach me how to walk properly. I wanted real maid shoes but Linda saw heels on sissymaids so I ended up with heels too. We talked about what I was wearing and what she thought I should wear from now on. In Linda's mind if she was going allow me to wear a maid uniform I was to wear one all the time.
We sat down while Linda wrote out some rules for me to follow as a way to thank her for allowing me to wear a maid uniform. Linda demanded I think of myself as her sissymaid immediately and get used to maid clothes and maid work. She was more than willing to play along with my fantasy however she expected it become more real than fantasy. I wasn't sure what all that meant when Linda told me she liked the idea of being called Mistress or Mistress Linda if I preferred and she would only call me sissy like she read on Auntie Helga's. Some of her rules were out there but when I brought it up she asked who was the Mistress her or me. Linda mentioned a few times it was me who introduced this whole thing and it was me who was going not only dress like the maid I wanted to be but I was going to be the maid she expected me to be. I wasn't going to give Linda any trouble since how many wives would allow their husbands to live out a fantasy involving wearing a maid uniform. Linda unpacked the bags making room for my new panties and bras in the drawer. She then surprised me with slippers and a couple of nighties she bought when I was in the washroom at the store.
Linda told me to follow her to the laundry room showing me how the machines worked and how to sort laundry. As she walked out of the room Linda looked back thanking me for sharing my fantasy with her smiling back at me. So I started the laundry and then it was cleaning the bathrooms with me wondering what did I get myself into here. As I worked away the chastity device on my penis was letting me know it was there so much that I asked Linda to take it off for a while. Linda laughed telling me it hadn't been more than a couple of hours and then I heard 'not happening Rob'. I tried again to talk to Linda about the maid uniform part and the maid part when she said I forgot the sissymaid part. Smiling at me Linda gave me the 'come on Rob at least try it for a few weeks before complaining'.
I ended up agreeing to Linda remembering if it wasn't for her I wouldn't have the opportunity to be her maid and wear my new uniform unless I did it behind her back and that wasn't my style. When it was bedtime Linda sent me to put my new nightie and slippers on so she could see them. It was cause for another laugh but not a cruel laugh. Linda said she was pleased with the results and I was going to make a super sissymaid for her. I am the one who goes to bed later so I thought it was a good idea to let you know what happened Auntie Helga. It was probably more than either of us thought but it happened making me think it could have happened years ago.
In the meantime Linda will experiment with things she read to gain a comfort level of this change in our relationship. As for me I couldn't be happier and more scared at the same time which I am sure is normal for a guy in my situation. It was a good idea you had earlier today about me having an honest conversation with Linda. It could have gone either way but with her knowing my thing for maid uniforms I was fairly confident she would let me try one on at the very least. Linda was pleased with me for asking you for assistance before talking with her in case you would have advised against my idea. For that Auntie Helga I have to say thank you very much. Time will tell if I continue to be so thankful won't it? Linda did surprise me as I never thought she would want to feminize me the way she was talking tonight but then again she had never read about sissymaids before. It goes back to what is in it for her and she loves most things that are feminine. I guess that is why she loves me too.
Thank you for your letter Robert. So it seems the conversation went well and now you not only dress like a maid, you are a maid and this is what you wanted. Your conversation with her was well done, providing her the information she needed to make an honest decision. Now you are going to become her sissymaid and that is going to be amazing for both of you. Congratulations.