Became Her Sissy

A while back I started my own business and had a small office. I realized I needed a secretary, so I hired an older woman to help me. She worked for me for five years and never once did either of us talk about sex or our personal lives. I have been a crossdresser since I was younger when I explored my mothers panties and pantyhose. One day, I dared myself to wear a pair of pantyhose to work. I was careful to have a pair of long socks over them. It started to rain, and I ran out to roll up my windows on my car. As I came back, I slipped and turned my ankle. My secretary helped me in and lifted my pant leg to look at my ankle. She could not help but see I had on nylons. I was embarrassed, but neither of us said anything. The next morning when I came to work, there was a new pair of pantyhose on my desk and a little note asking me to let her see them when I put them on. One thing led to another as I discovered that she had entertained a fantasy of being a dominant woman over a sissy. Within weeks, I became her sissy. She bought me everything. In the privacy of my office, I dressed daily and also orally serviced her daily. We even did some very kinky things. One day as I was dressing, she asked if I was ready yet to become a real sissy and do a man. I protested even though that was a major thought in my fantasy world. But by that afternoon, a very handsome young man came into my office, and I was introduced as Missy Sissy, Missy by my secretary. After a few formalities, she sat down and ordered her sissy to perform his first oral on another man. This went on for many years and it was so much fun. I am married now and no longer have my business but I am again lucky because my wife knows I crossdress and enjoys seeing me dressed and loves to explore with others. Check out our profile for more about us.
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2 Responses Jul 20, 2010

All married males should know what's it's like to dress like their wives and suck a **** increases their understanding of the female gender. Of course, once a cute wife knows her husband can be a good sissy, then she will be more likely to seek out a 'real man' for *******, pushing her husband into a secondary role in the bedroom...which is hot!

Well played in the end you got what you desired. Again you are so lucky to meet and have people like this in your life.