Sissy Training

This is a true story, looking back it is hard to believe it actually happened, but it did.

I was working for the government in DC and living in Maryland and my fiancé was up near Cape Cod. Just about every weekend she’d fly down or I’d fly up to spend the weekend together. We’d been doing this for about a year since I took the job in DC. Our sex life was fantastic. We’d role play, put each other in light bondage… all sorts of fun things. I knew she was bi and we occasionally would invite another woman to join us. She also knew I liked to dress up. We’d often go to the local thrift stores and buy sexy things for both of us. We even went to a shop in Georgetown and bought a pink satin maids outfit that she’d have me wear and serve her! Most of our fantasy talk in bed was either about me being dressed up or her being taken by a BBC or another woman.

One night we were relaxing having a glass of wine and watching a movie. Sue mentioned that she had seen an ad online for a place in downtown DC where a woman by the name of Lady Ann trained guys to be sissy maids. We talked about it for a bit and she could tell I was getting excited by the thoughts… we made love right there and it was fantastic! Sue didn’t mention it again and I pretty much forgot about it.
A few months later my birthday was coming up. Sue told me she had an awesome weekend planned for me. She told me she was taking the day off and flying down early Friday and was hoping I could at least take the afternoon off. I picked her up at the airport at noon and we went back to my apartment. We had lunch and the subject turned to the weekend plans. Sue pulled a piece of paper from her pocketbook and handed it to me. She told me that she had two possible plans… one if I agreed and signed the paper and another if I didn’t. The paper said that I agreed to do as she ordered me to do and if I did not follow her instructions I gave her permission to send photos of me to whoever she wanted. I asked her what it was she had in mind but she said I’d find out IF I signed the paper. So, I asked what the other plan was and she said a trip to the museums in DC. So I signed the paper….