from Jade

Dear Auntie Helga,

I took your advice by talking with my wife after dinner tonight while I cleaned up the kitchen while she drank her coffee. She had noticed I did some laundry today and thanked me for it. I asked my wife if she would like me to take over the laundry and cleaning for her some day. My wife is no fool as she asked me if I was feeling alright when I admitted I was alright. I went on to let her know if she taught me how to iron the clothes I would be happy to learn. My wife not taking kindly to kidding about something I would have no intention of doing stopped me in my tracks telling me to come out with it. I told her I loved her more than anything and had done some reading where many other men became their wife's maids. My looked at me wanting to hear more so I explained in detail the type of maid I wanted to be was a sissymaid who would look after everything inside the home so she could spend more time doing things of enjoyment.

My wife had never heard of a sissymaid so I showed her what I meant asking her permission. She started to laugh seeing sissymaids dressed in pink satin wearing heels. My wife after a good laugh asked me if I wanted to dress in pink like the pictures and be a sissymaid for her. I didn't have to think about it so I said yes if she should allow me to serve her as a sissymaid. My wife went to the bathroom and when she returned had a few more questions mostly about what I wanted to do for her. I answered them to her satisfaction as she thought about it for a while.

The thing that bothered her was thinking of me dressed like other sissymaids but the trade off was worth it in the end. We talked about what a sissymaid was and what she would have to do to be my Mistress. When I shared a few pictures of Mistresses spanking and using strapons my wife asked me is that what I wanted her do to do me. I stood there blushing as she read my mind saying you do don't you Jade. My wife stood there looking at me admitting she had heard everything tonight.

Looking at a few pictures with me commenting on each of them and noticing most were wearing a chastity device my wife said if she agreed I would have to wear a chastity type device too. My wife is a smart woman and she was testing me and testing the waters to see if I was serious or full of it. I wanted to be her sissymaid so bad I agreed to everything she talked about as we looked at other sissymaids. She also noticed none of the sissymaids had hair on their legs or pubic areas making fun of them. My wife said I guess that is why they are called sissies right Jade.

My wife decided to accept my offer under a number of conditions all of which I agreed and was ready to accept. I still had to let my wife know about my sissymaid clothes and that I was ready to begin tonight if she wanted me to. Before I had a chance she made a comment thinking I already owned a pink dress wanting to know if she was right. Blushing I admitted having a complete wardrobe including a chastity device. My wife shook her head knowing me so well then telling me it was okay, she wanted to see me in my pink dress. I gave her a hug thanking her for allowing me to serve her from now on.

She wanted to see me but pointed to a picture of a sissymaid telling me to go shave myself first then come back dressed for her. Auntie Helga I was so scared and excited having let my secret out finally but I went to shave myself already feeling more submissive as I dried myself off. My wife was watching TV so I went to the basement to get ready starting with the chastity device locking it on tight to show her I was willing to give up my penis for her. Next was a pair of lace trimmed pink nylon panties, my bra with silicone forms and my open bottom girdle. My hands were shaking as I clipped the garters to my stockings. I slipped one of my sissy dresses over my head zipping up the back before putting on a pair of my highest heels. As I put my wig on I felt the fear of my wife waiting upstairs to see her new sissymaid. I started up the stairs in my heels shaking like a leaf counting how many stairs were left before opening the basement door to show my wife for the first time. I asked if she was ready but to my surprise my wife asked if I was ready as I stuttered with a yes I think so.

My wife told me to come in and stop taking so long. All I heard was OMG Jade you are a sissy just like the pictures. She got up looked me over lifted my dress and pulled my panties down to see my penis in chastity. My wife smiled then laughed letting me know I was screwed now. She asked where were the keys when I passed the same keys to her from the day before. My wife knew they were the same keys as she said she was so close to knowing yesterday. My wife told me my penis was going to stay in chastity longer because I lied about the keys yesterday. I said yes Mistress with her smiling at me.

She told me at first she thought I was fooling around but seeing me in pink was already something she liked. She looked at my bra and commented on my girdle and she liked my shoes too. Auntie Helga I guess I did a good job buying everything with only the internet to help me. My wife left the room returning with a basket of laundry ordering me to follow her. She set up the ironing board then started to show me how it worked. My wife watched me iron her clothes helping me understand the settings to be used with different clothes. Talking with me she asked how long I wanted to be her sissymaid so admitted a long time. My wife wanted to know why I didn't ask her sooner but I feared rejection of the idea.

Smiling at me she told me I had her blessing now and from now on for that matter. I finished the ironing so we sat reading about sissymaids and Mistresses where she learned about strapon training. My wife told me she was prepared to take this seriously if I wanted her too. I admitted to wanting to be the sissymaid she wanted me to be so she told me to be prepared. We went downstairs with her wanting to see what else I had hiding from her. My wife's eyes lit up when she saw all the panties, bras and dresses. Then she noticed the strapon and spanking paddles. She told me it surprised her in one way but knowing me for so long she wasn't surprised all that much. Holding the strapon my wife asked if I ever tried it out but I had saved it for her and she told me she was going to use it on me alright. She took a paddle then slapped my ass with it telling herself it was going to be fun having a sissymaid. My wife pulled out a couple of pink nighties telling me I was going to wear them to bed from now on. I said yes Mistress as she smiled again.

I asked if I could wear my pink slippers too which was a yes answer. We carried everything to the bedroom the made room in my drawers for my clothes. While my wife sat on the bed I changed into a nightie for her as she told me to leave my bra on. I was told to wear a bra 23 hrs a day from now on unless told otherwise so I replied yes Mistress. My Mistress outlined what she wanted me to do tomorrow as her sissymaid with me replying each time yes Mistress. I was told the only makeup to wear was bright red lipstick since I wasn't a woman but a sissymaid. Mistress told me in time she would want me to perform other duties but for now house work was to be on the top of my list every single day. Mistress learned quickly telling me every single mistake would be cause for disciplinary action. She asked me if it was clear to me what will happen each time as she hung a paddle near her side of the bed. Mistress sent me out of the room so she could fall a sleep. I usually wait a half hour before I go to bed and pray I don't wake her getting in bed.

Thank you Helga for getting me to be honest and not surprise my Mistress. You were right and I am glad I followed your advice in the end.


Thank you for your letter Jade. Congratulations, you are well on your way to fulfilling your dreams and all it took was a conversation, now the fun begins. She does seem to have come to see the benefits to her pretty quickly, so thats good.

So now into chastity you go at your wifes command, seems a fair trade. What a wonderful turn of events and I hope this email finds you with a big smile on your face and joy in your heart. I am so happy for you and thank you for such a heartwarming letter, my hope is that other men with secret desires might see that all you have to do is ask honestly.

Auntie Helga

Return to Index
Letter 1