Dear Auntie Helga,
My talk with my wife went better than I expected but then again I had no idea what to expect. I did talk about how much I love her and would do anything for her if she asked. I asked if she should allow me to take over the house hold duties including all the cleaning and all the laundry, ironing and cooking so she could relax, rest or go out with the girls when she felt up to it. She asked if I really wanted to do all of it for her. I agreed to take it off her shoulders. My wife thought I was giving her the maid she wanted without spending the money and having a stranger in the house. I went on to tell her about other men doing the same for their wives and many of them dressed the part. My wife is not stupid when she said did I mean maids or sissymaids. I said both which is when she aske me which one I wanted to be. My heart missed a beat as she waited for an answer. She said oh come on don't be shy if I want to do something for her then let her know. I replied sissymaid with a low voice which is when my wife said see that was hard was it. She asked me if I wanted to wear a sissy dress, pretty lingerie and heels like the pictures we looked at a long time ago for Halloween. Again I said more than she knew. I didn't know it but a girlfriend of hers had an uncle who was a sissymaid for her aunt until he passed away. I went to get my list of sissymaid stuff I wanted to buy some day showing it to my wife. We went on the computer to look at what I had chosen. Without notice she called a girlfriend and then another asking questions about sissy maid dresses, lingerie and shoes. She wrote down store names beside the items I had on my list and names of who to talk with. My wife knows women in all kinds of businesses as many are girlfriends. She called her friend whose uncle was a sissymaid sharing the news with me turing beat red. After hanging up my wife told me Donna agreed to go shopping with me today but I had to go shave all my body hair first. My wife sent me to go do it and when I was finished a long while after she have me a pair of her panties to wear. I put them on so fast she was surprised. My wife told me to take my list with me and go to each store on the list asking for the woman's name she wrote down. She told me to ask Donna where to buy the chastity device I wanted and if it was a good one.
I picked up Donna blushing red when she got in the car but she was cool and didn't make a big deal. All she said was good on me to take on this challenge. Before we went to the first store on my list Donna recommended going to a uniform supply house where a friend of hers works. I just drove and followed knowing she knew more than me. We went their and the ladies talked for a minute then we went in the back room. The lady showed both of us 4 sissy dresses paid for over a year ago but never picked up. The lady looked at me and at the size tag figuring they might work. Donna said why not try one on while we are here taking my hand pulling me to the change room. I had that dress on in lighning speed and it fit with more room up top than I thought I needed. Donna asked if she could have a look to check the fitment. I was hesitant to open the door but did. Donna looked at me telling me it looked very pretty on me. Long story short Donna got a great deal for all of them from her friend and off we went. Next we went to a woman's store on the list asking for Gilda who took us to the back where there we no customers. Gilda talked to me about sizes and styles of bras and panties then went to get some of each. She wanted to measure me for the bras and did so with my shirt on. When she came back I went in the change room taking off my shirt as she instructed and tried on 4 bras with her talking to me through the door. When I was done she wanted me to leave on the one I liked and fitted the best. I opened the door so she could check it and make adjustments. Donna went to get one of the sissy dresses as they were talking cup size. When Gilda saw the sissy dress she agreed with Donna a D would work best with the dress.
Gilda returned with a the same bra but with a D aksing me to try it on with her helping. Donna commented on my shaving job with a wink. Gilda put a pair of silicone breast forms in the bra to check for size asking me if it was what I wanted or my wife wanted with a smile. Next she explained most crossdressers and sissymaids wear full brief nylon panties showing me 3 kinds. Donna picked the ones with some lace on them. We were all finshed there then on to the shoe store where we met Ann who had a few pairs ready for me to try on. I stood up with each pair so Ann could check how they fit. Donna suggested 2 pair one with a 4" and one with a 3" heel. Our next stop was to look at chastity devices. I saw the one I thought was a good one but the lady in the store showed us a newer model that wouldn't come off without a key. I bought that one and we headed to another store to pick up stockings, pantyhose and a garter belt. By the time we got back to my place my wife had called asking if Donna wanted to stay for dinner which is why I was taking her with me. We showed my wife all the purchases and how helpful her friends were so it was all left on the bed. I wanted to get started so bad but my wife told me after Donna leaves. She said Donna will see me another day don't worry.
After dinner I took Donna home and thanked her for helping us with the shopping. She enjoyed the day and wished me luck as a sissymaid remindind me to always obey my wife. When I got back my wife was waiting looking through everything. She told me to take off my clothes so she could help me slip into my new dudds. Oddly enough my wife wanted to put the chastity on me the most since I often bugged her about sex. My wife hasn't want me on top of her for months but I do get to give oral when she is feeling well. You would think she was an old pro the way she put the chastity on me moving my testicles and penis around. She locked it then looke dup at the ceiling saying out loud thank god then laughed. As she helped me with each item she asked was I sure I wanted to put it on teasing me. I would say yes and she would say ok. When she held up one of the sissy dresses she remakred how pretty it was slipping it over my head. By now my penis was starting to swell in the chastity device. Now I know what that feels like and it kind of hurt. Next came the heels which were the 3" ones as my wife thought I would need practice before the 4" ones. My wife asked me if I wanted to wear a wig or was I happy as is. I didn't know so she went to get one for a costume she wears to parties. When it was on she looked at me thinking out loud she liked the idea but maybe a better style would work better. She asked what about make up and did I want to go that far or let her make the decision. I agreed she should make all the decisions as my new Mistress.
My wife stood back looking at me smiling then said she only wanted to say this once just to get it out of her system. She said I looked rediculouslly cute in my sissy dress laughing. I asked her if it was all going to be okay and was it going to work for her. She told me it was going to be okay bit give her some time to get used to it. I asked if she wanted to read more about sissymaids or do things he own way. I was trying to hand the reins to her as the decision maker. My wife said sure but she wanted to go have a nap first. In the meantime I was to get busy and be the sisymaid I wanted to be and clean her house. I did a few things then sat down to write this long email. Auntie Helga my heart is racing with excitement as it is more than I thought. I have no idea how and why these feelings in me ocurred but they did and so powerful. I am excited like horny but no erection even though the chastity is on tight enough one would never happen I can still feel it is more mental for me than physical. I am so happy I wrote to you and soon my wife will be too. I had no idea of what to expect from you, my wife or any of the wonderful women I met today. None of you made fun of me in any way which shows how special women really are in the world we live in. I am looking so forward to helping my wife live without the worry of cleaning and laundry anymore. I am sure she will get used to my role very soon and my appearance too knowing how happy it makes me which in turn makes her happy. I love the feeling of what I am wearing as foreign to me as it is today.
Thank you for all of yout advice and openess to help a confused husband.
Thank you for your letter Mike. Many men have this desire, you are not alone and its very possible you could live out your days as a sissymaid in service to your loving wife. Most any woman would love to have a sissymaid once they can see the upside for them and though it might surprise them at first, most come to love being a Mistress.