The Making Of A Sissy
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 closet cross-dresser since I was eight when my mother put me in a dress for a costume part. 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 put the top up on my convertible. 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 now has been going on for almost fifteen years, and I lost count of the number of men.
— Butch, 62
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Dating, like it or not, is a game. And the boys who learn how to play it will fare better with the fairer sex than those who don't. So you might as well start studying these now.