Dear Auntie Helga,
My wife and I help with fund raisers a few times a year and one of stores we help is the lingerie shop where my wife and girlfriends shop. Last year I helped by collecting donations outside the store wearing a pink T-shirt and a bra like the women. This year my wife pulled a fast on me that went like this... again all to help breast cancer.
When I went to change in the back my wife took my clothes leaving me in my underwear in a lingerie store. Talking through the closed door she advised me the girls wanted me to wear something different this year so I was prepared for something funny. The change room door was open at the top so the girls in the store could pass things to you without opening the door.
My wife passed me a pair of panties of which I passed back again. She tried again telling me not to make a fuss and just put them on and pass her my bowers so she could put them with my other clothes. Next she passed me a bra and told me not to pass it back. I fiddled around until I got it on so she passed me breast forms to put in the bra so I did. A garter came next, stockings, pink dress covered in lace and ribbons with instructions to put it on so again I did. Jackie passed me a one at a time high heels which I put on asking if I was ready. I unlocked the door to see all the girls standing there clapping with Jackie clapping with them. All I could think about was total humiliation not raising money.
Jackie walked me out to the front of the store while we collected money from people walking by. Lots of them laughed but the women that did stop gave more money this year than last. The girls at the store were very happy with the money raised in the 5 hours I was there. Jackie convinced me to change at home while she went to get the car. I rode home dressed in a pink sissy dress, which is what I learned was on me. The girls at the store donated everything I was wearing only if I stayed the full 5 hours in it which I did not knowing I won myself a new outfit.
Since then Jackie has been on this kick for me to wear the sissy dress at home. She keeps hinting I be her sissymaid so I can dress like I did on the weekend every day. I don't to dress like that every day and she is lucky I dressed like that on the weekend when most guys would have said no way. Auntie Helga why does my wife want me to be her sissymaid and why does anyone want to be a sissymaid? I dressed like I did since I had no choice and for a good cause but why would any guy do it voluntarily? I figured you would know lots about this and what I best say to my wife to put this to bed once and for all.
Thank you for your letter Carl. That is so great that you help other people in need, thank you. So they dressed you as a sissymaid and now that your wife has seen the effect she may want to have you become her sissymaid for real, if I understand correctly.
I couldn't say why or even if your wife wants you to be her sissymaid but many wives do and for all sorts of reasons. Many men become sissymaids because they love their wife and she wants it, some because they enjoy dressing in the silky clothes, others because they wish to take a load off from their busy day, relax and let her make the decisions. I suggest you discuss this with your wife and keep an open mind.