After much browsing the internet I finally found what might be the answer to my husband's fantasy. You see a few weeks back while we were enjoying a night together a guy on TV asked his girlfriend what types of childhood fantasies did she have or did she even have one. One thing let to another where my husband asked me the same thing then I asked him. Mine was to become a princess and marry a rich man. My husband's shocked me when he admitted dressing up as a girl then being caught by his mother. We laughed about it now that we are in our 30's we are no longer kids.
A few days later I asked my husband more about his fantasy with him just wanting to forget about it maybe feeling somewhat embarrassed. I probed him to tell me more about it starting with how he imagined being dressed. He shared his interest years ago with the thought of wearing a dress, blouse and skirt as well. I had never heard a guy express himself like this before so I probed for more. This talk went on for a while with my husband having those thoughts as he got older by the clothes he described. By the time we were finished my husband explained that he always fantasized about dressing as a woman.
Not wanting to let this go with my own curiosity eating away at me I decided to do some reading about men that dress as women. Learning about cross dressing, then forced cross dressing and femdom was certainly an eye opener for me. Growing up we all hear of these terms however I don't think most of us give it a second thought. I thought it might be fun to allow John to enjoy his fantasy with me then maybe take it to another level. That night I asked John if he would mind if I bought him an outfit so he could wear it for me. He was dumb founded although didn't say yes or no. I went on to let John know my thoughts were to allow him to fulfill his life long fantasy. With that I went to get my measuring tape while John allowed me to measure him up.
It was about a week later than I had purchased enough to get John started. One Saturday morning I brought everything out for John to wear. He had his choice of a pretty dress or blouse and skirt. I started helping John with panties and bra joking at how cute he looked in them. John was bright red with embarrassment however it didn't bother me as I kept helping him until he was finished. He spent the day wearing a blouse and skirt for the first time in his life. John did alright in heels surprising me but then giving me other ideas. Each weekend I let John wear either his dress or blouse and skirt as he began to enjoy it and to be honest so did I.
Now Helga what do you think about introducing John to some petticoat training? I am impressed with what other women have done training their husbands to be sissymaids. John enjoys wearing his new clothes however I would like to add a sissy dress then train him to be my sissymaid. I think he will accept my offer even though he won't like a sissy dress right off the bat. What do you think about my idea?
Thank you for your letter Brenda. I hope the site and I can live up to your expectations. That is so interesting to hear about his childhood, many boys have these desires, often starting with simple curiosity about the clothes girls wear, to trying them on and finding that they love the feeling, that also might have been difficult for him to admit.
A wife wants her husband to be happy and to explore each other's fantasies though we are often surprised when we learn what they are, your willingness to explore his is very encouraging.
As you might expect I am all for your idea to explore training him to become your sissymaid, when you have a willing participant as you seem to, it should be pretty much smooth sailing, though this may change the dynamics of your relationship as he takes on this role and you take on the role of Mistress. Of course there are far more upsides than down, at least for you and since he loves pretty clothes, he should be okay with it.