For about two years I watched my secretary Judy walk down the hall away from my office with my desk set so I could see her walking with her sexy wiggle. I often would go to the restroom and masturbate thinking of her ass moving so sweetly. With each step she would kind of flick her butt in a way that made me nuts. One morning I came in to find a package on my desk. I opened it to find a pair of sexy dark blue panties that upon checking them had been worn by a female. I saw a note in the box. I read her demands...
For so long you have watched me walk down the hall away from your office, you may have not known but I knew you were looking at my ass. I set up a camera in your restroom and have several CDs of you doing a very naughty thing after you had watched me walk away. Put on the panties and come to my office. When you get there get on your knees and be silent until I speak to you. Any sound coming from you before I speak you will be sent away and I will send out the movies to every employee of the company and some of your accounts. I thought for several minutes and knew I had to obey her demands. I then removed my clothes and put the panties on and replaced my clothes. The longest walk I ever took was to her office.
When I got there I knelt in front of her desk she continued to work at her computer for what seemed like an hour. She then looked at me and smiled, she said remove your pants. I stood and slowly removed them revealing the panties. She again smiled with a evil grin. She told me to turn around and she made me stand there with my backside to her. Judy told me to tell her how much she liked my butt and make sure she liked my every word or I knew what would happen. I said I loved her butt and loved watching her wiggle as she walked down the hallway.
She told me to tell her some of my thoughts I had when I was doing the naughty things in my restroom. I slowly began to tell her of wanting to kiss it and even lick her butt. She told me how gross that sounded. Judy told me to get on my knees and then she walked in front of me, I was told to kneel she turned her butt to my face and told me to show her how much I loved her butt. I began kissing her butt even through she was wearing her dress slacks. I kissed every inch of it many times.
Judy told me to go back to my office and that I was to be her personal slave as long as she desired and that she would be my boss. She made me call her Mistress Judy when no one was around. The new life began. I was made to wear women clothes under my suits every day at work, I also was to come to her house on weekends and dress in a French Maid uniform and clean her house including hand washing her panties and bras. After a few weeks her mother caught me. She had dropped by unannounced on a weekend I was there doing house work. That was a humiliating day for sure.
Shannon (Judy's mother) was almost as shocked as I was when she walked into the kitchen with me on my knees washing the floor in the maid's uniform. My butt was toward the door and at first she thought that it was Judy. When I turned she gasp. Judy walked in as if nothing was going on and said I see you have met Sissy. Her mother soon got all the information about my naughty doings. She agreed that I deserved this punishment. Shannon soon got into the act of humiliating me with words and she also perked up when Judy said I had missed a spot on the floor. Shannon said do you think she needs a spanking?
Judy reported with do you mean like you used to spank me when I was bad? Shannon said "OH YES". I was soon in the living room over her lap with my head low and her hand in my back so I could not move. My panties were down around my ankles and her hand hit my backside with great force. After many swats my tears were flowing and I was begging her to please stop. When my bottom was red she stopped and dumped me off onto the floor and I was curled up crying like a baby. They both laughed and kept calling me a sissy cry baby.
Many days were spent with me being punished by them and not long after that day Judy and I were wed and all of my assets were put in her name, I also took her last name. My first name remained the same at work but at home and in soon places where she wanted to humiliate me she called me Sissy Jackson. Mostly in women shops she would make me hold panties up to my body to make sure they fit. We now shop at a store where everyone knows about me and they love making me try on items while they all watch. Next week we are going to an adult shop to get some kind of toys.