Sissy Assistant

It was a dark day when I went into the boss's office and waited for her to come in from another meeting. She told me that there was a problem with my accounts. I worked for her accounting firm. I looked at her and ask what the problem was and she told me that two of my accounts were tampered with and that a loss of over a thousand dollars was missing. I knew that I had taken the money and that I had planed on replacing it in two days but there was a check up on my accounts before I could put it back. Miss Jones said that she would have to report this to the police and that I would be arrested for stealing from the accounts. I began to try to explain, but she said that this sort of thing would not be tolerated and she had to see to it I was punished and that the other accountants had to know that she would not let anyone off for stealing. I told her that I would do anything not to go to jail. She said there might be a way out of this, but it would be humiliating for me. I did not want to go to jail, so I said, "I will do it, just please don't send me to jail." I was told to come to her office after work. When I got to her office, there were three of the women that also worked in the office and all three were women I had harassed several times. Miss Jones told me that for the next thirty days I would be the assistant to these three women and that I would do everything they told me to do or I would go to jail. I stammered, "Okay," and they laughed. I was told to go to Maria's house that night for instructions. When I got there I found out that I would be their sissy assistant and that I would be wearing women's clothes for the whole month. I would be getting their coffee and going out to bring their lunch into to them. It was the most humiliating time of my life. I was dressed in panties, slips, bras, and dresses or skirts every day and the dresses and skirts were way to short. If I bent over at all, my panties showed. The other men in the office teased me by hitting on me and asking for oral sex. They told me that if I let them have some sex, they would help me with my accounting and they laughed their butts off every day at me. My wife said that she was going to carry on this punishment when she found out about my hitting on the women at work. She said if I had panties on, maybe I would not roam.

— Rob, 38

Love Library: Featured Articles