Dear Auntie Helga,
I did tell Janice I like wearing the panties she bought me more than I did in the beginning. They are silky and I think they are nylon. I am happy to hear you have talked with Janice, my honey. She is getting to like this more than I thought. Janice showed me your website and pictures of other men wearing feminine clothes mostly maid dresses. She asked me to agree to try being her sissymaid for a few months. Janice picked out sissy dresses for me assuring me we would have fun with a role change. It was hard to say no when I could see Janice was enjoying me wearing women's clothes now every day.
I have to admit some of it feels very weird to me but when I am with Janice she makes me feel comfortable. Now I have an idea what it is like to dress like women do and walk in their shoes so to speak. Janice talked me into shaving my body nice and smooth like hers even my pubic area only has a small patch of hair now. It feels weird to me but Janice loves it very much. She told me that all sissymaids learn to be feminine so having hairy legs is not feminine at all.
One thing Janice asked of me was to keep an open mind and at least try every she tells me which I agreed to do for her. She was telling me that most sissymaids love their wives so much they will do anything after getting used to it. I can't say anything bad about it as it isn't painful or disrespectful and Janice is having fun with it. We went shopping today with me wearing my breast forms in my bra and that was something different that was for sure. Feeling them move and bounce as I walked gave me more of an idea what it would be like if I had real ones. Janice was joking with me telling me I should wear one of my dresses or skirts sometime. My response was no thank you Janice. She asked if I wanted to wear something pretty to her mother's house tomorrow but that was another no thank you Janice. We both laughed although I felt she might have been serious if I agreed to try it. I won't say no but she would have to make me look like a women before ever going out in a dress or skirt.
When we were shopping today Janice asked me which bra I liked to wear the most. She bought me another one as a treat which I can say most men don't get a new bra from their wives. Later on Janice bought me a new steam iron so I can start learning to iron for her. I didn't know she wanted me to iron clothes but she reminded me as a sissymaid it was something she wanted me to learn for her so I agreed. Janice ordered me sissy dresses for day to day wear so I don't put too much wear on my favorite blouse and skirt. She is really looking forward to seeing me wear a sissy dress for her. I don't mind the black one but the pink one will take some time for me to get used to I think.
Auntie Helga I am getting the feeling that Janice wants me to become her sissymaid for longer than a few months. I am not going to say anything as long as she enjoys it. They say a happy wife makes for a happy life which is good enough for me. Janice wants me to help her now. I hope you like my email and thank you for talking with Janice.
Thank you for your letter Reg. Being her sissymaid for the next few months will be amazing for both of you and so long as you do what you're told, it will be easy. She does seem to love you being feminine for her and I know you will try to be that way to make her happy, won't you? Maybe some day you will be able to wear something pretty to her mother's house, it would be so nice to be accepted and loved by the whole family and seeing how much they support your feminization.
She may want you to be her sissymaid for much longer, but don't worry too much about that right now, just go with it and obey her, this will make her very happy and I know you want to do that whatever it takes and for however long it lasts, right?