Dear Auntie Helga,
When we got married 6 months ago I never heard of female led relationships, Mistresses or sissymaids. My new bride didn't waste anytime talking with me about her wanting to lead our marriage and me following. I was always more than willing to do my share around the house but soon Jen pushed me to do more. Kind of confused I shared it all with my twin sister on Wednesday nights when I normally had dinner at her house. It was difficult to tell my sister Jen was taking control but somehow Anne sensed something was on my mind. When I explained it all to Anne she totally understood where Jen was coming from and offered to help me. It was great to have my sister to help me learn how to do a better job cleaning and show me how to fold laundry neater.
Every Wednesday night Anne would talk with me about how the world was changing for both women and men. For years women looked after most if not all the housework and the man looked after the cars and outside the house. Anne explained today women take their cars to the car wash and pay someone to look after the landscaping at home. In the house the husband looks after laundry, cooking and cleaning for their wives which was new to me. Anne showed me some articles on the internet and introduced me to men as maids. She explained what Jen was doing was preparing me to be her sissymaid and there was nothing I could do about it except do it or leave her.
It was and is difficult for me to understand why women today want their men to be feminized and work as male maids. Anne took it upon herself to start me off wearing panties, a bra and an old dress of hers every Wednesday night for a few hours. I felt so embarrassed and uncomfortable the first few weeks but Anne took me under her wing. Anne decided to take me shopping one Wednesday night buying me all kinds of things from bras to shoes. We had fun or at least as much fun as a brother could have with his sister in women's stores. Anne showed me several sissy dresses online asking me which one I thought Jen would like me to wear but I wasn't sure. I really didn't want to wear a sissy dress but Anne assured me Jen would insist as all sissymaids wear them. Anne picked out one with all kinds of lace on it and chose pink as the color. Before I knew it the dress was ordered with Anne smiling at me then letting me know it was going to be fine.
A few weeks later Anne sent me a text to let me know my new sissy dress was at her house. I didn't feel good knowing on Wednesday Anne would be helping me put it on at her house. A few days later it happened with me putting on some of the new things we bought and then the pink dress. I stood there all dressed in pink trying to keep from falling while wearing heels for the first time. Anne took me to the mirror to show me and I almost had a stroke looking at myself. My sister holding my hand assured me I looked very pretty and Jen was going to love me this way for many years to come. It was all sinking in I was being prepped to be a sissymaid by my own sister.
For the next couple of Wednesday night's Anne helped me get dressed and I practiced walking and working in my sissy dress. At home life seemed normal with Jen keeping me busy with house work and learning to cook when she had time. During the week I talked with my sister about what women expected having sissymaid husbands. She was very good at explaining more why it was necessary and how I should act in front of Jen as I prepared to be her sissymaid.
Anne let me know she had a surprise for me for Wednesday night. When I arrived while taking a shower Anne talked me into shaving myself from head to toe letting me know all sissymaids have clean shaven bodies. I was so hesitant knowing my wife Jen would see me at some point. Anne explained it was my way of letting Jen know I was ready to be her sissymaid and it would actually make her happy.
I did what Anne wanted me to do even though I was scared to get caught at home. Before I got dressed Anne came in to make sure I shaved all of it while I was toweling myself off. Anne told me she bought something for me to try out holding up a chastity device which I had never seen. I asked why and what it was for with Anne smiling at me. She explained all sissymaids wear a chastity device at some point so she thought it just made sense for me to try one on. When I resisted Anne looked at me letting me know Jen might not be so nice in asking me. With some help I was able to put it on and Anne locked it for me. I spent the night dressed and locked with Anne talking with me about how cool it was going to be for me as a sissymaid.
Two nights went by until Jen noticed my smooth legs. To my surprise all she said was 'you shaved your legs Casey and she liked it'. I thought as my heart shrunk in my chest Jen was going to freak out on me. Catching me come out of the shower another comment about my smooth body and no pubic hair. I asked her if it was alright with her and she gave me a thumbs up. Later in the day when I talked with my sister about it Anne told me Jen was going to love me clean shaven and she was right after all. I felt relieved knowing my sister was right and Jen approved. Anne talked with me today about letting Jen know I'm ready to be her sissymaid and showing Jen my new sissy dress.
Anne thinks I should call Jen Wednesday and have her come over to Anne's place on the way home to see me in my sissy dress. I'm terrified but Anne told me I was ready and it was going to happen regardless so why hide it any longer. Jen did tell me a few times I was going to be her sissymaid dropping hints about it. That was the reason I talked with my sister. Anne thought having me all dressed and in chastity Jen was going to be so happy with both Anne and me. She also felt by me handing the keys to Jen while on my knees would definitely show Jen I was ready.
Auntie Helga is this as normal as Anne tells me it is with men of today? I love my sister and I know she would never do anything to go against me and I love my wife Jen too. The whole thing just makes me nervous to dress like a woman or sissymaid in front of Jen even though as Anne told me it is what Jen wants me to do. If you can offer any assistance I would love to hear from you.
Thank you for your letter Casey. More and more marriages are female led, all to the better it seems to me. It would appear that your sister has been in contact with your wife and that they have planned this introduction together. Anne obviously approves of the idea for you to become a sissymaid for for Jen and I feel before too long you will be standing before them both dressed properly in your sissy dress and ready to serve.
I can't say what's normal, who can, but I can say that its not unusual for a wife to have her husband become her sissymaid along with all that implies. Your nervousness is to be expected, all new things we do cause us concern and obviously dressing like a five year girl as an adult male is a daunting concept to say the least, that said, many have come before you and many will follow, you can and will adapt. It will be okay.