My name is Donny and at the age of nineteen I struggled with my desire to feel the softness of ladies' underwear. I was working for a lady who was starting her business and needed someone to help her find things she needed for her thrift shop. Much of her income came from renting an area or section that they would rent. My job was to section off these areas for the renters.
My boss was so beautiful and she liked to wear low cut outfits and short in length. Her name was Jennifer but she liked to be call Miss Jen. Since the shop was not open yet she would come to the parts to see how things were going. I would often be on a ladder she would look up at me doing my work. One day she ask me to get down off the ladder so she could see over the whole building. She ask me to steady the ladder. You got it I did look up and there was her Satin panties they were a very soft Rose color and they covered the most beautiful butt I had ever seen. Not that I had seen a lot of butts. One of my fantasies was to run my hand over her panties cover hidden treasure. My mind ran a muck, the pictures that flashed before before my mind. Suddenly I heard a scream and a I looked up to see her falling. She fell into my arms and avoided bad fall. I held her in my arms and her face was so close to my face I almost kissed her red wet lips as she told me to put her down.
Miss Jen told me that I was not paying attention to what I was supposed to be doing instead of what she knew I had been doing. I begged her forgiveness but she walked away. Not long after the fall she called me over the speaker system to come to the office. When I arrived at her office she told me to sit down. I sat in a chair in front of her desk. She said she felt that she wanted to fire me for two things, number one I was supposed to be holding the ladder and number two I was looking up her dress. I hung my head and said yes Miss Jen I will pick up my tools and leave. She stood up and for the first time I noticed she was at least five inches taller than my 5' 5" frame that was also very small. She walked around the desk and she told me that I could redeem myself if I choose to instead of my leaving. I said I would do anything rather than being fired.
Miss Jen lead me out to an open space that she had set up for her things she was going to sell. One of the boxes was not opened, it was marked return home. She told me that she had brought this box by mistake. She went on to say that in the box was some of her personal garments. There was a stool that was kind of high I was told to move the stool closer to the box. Miss Jen opened the box and she sat down on the stool. (all I could think of was how lucky the stool was to have her butt on it). She watched me sweat as she opened the box and removed a pair of her sexy soft pink Satin panties and she held them up close to her body and pulled them tight across her and she looked down at my zipper the impression of my hard wet penis. I shuddered as I looked up and she was smiling I moved my hand in front of my pants. Miss Jen ask if I would like to feel the panties. Her voice lowered several octaves and her eyes twinkled as I moved my hand toward the panties. I took them in my hand. She ask if I liked them, my mind said "hell yes" but my mouth said no Ma'am and I swallowed about ten gallons of wetness. She look at me with her lip pouting like. She said I had hope you would want to wear them for her and in doing so I would not be fired. I almost shouted "YES I WILL WEAR THEM FOREVER".
Before I knew what I was doing I stood before her naked from the waist down. She knelt before me with her panties at my feet. I felt the softness of them as she slid them up my legs and over my butt yet the front was still below my (blushing) penis. She pulled the panties open and with her other hand she took my wet four inch penis and put it inside of the wonderful prison it were in. She stood up and looked down into my eyes and she said don't you like them on you? I said yes Ma'am.
Miss Jen sat down on the edge of the desk and she pushed me into the chair in front of her. She said you can do something for me if you want to. I said anything and I mean anything. She smiled and moved her skirt her ever knees and back toward her body. I looked directly at the stride of her panties they were wet so wet I though I could drink all of her cum. She pulled my head to her wetness I was thinking I had died and gone to Heaven. Just as my mouth touched her she pushed my head back. She said I don't think we should do this. I said I think it would be OK.
Miss Jen said that if I were her sissy slave it would be alright but you are not my sissy slave. Do you want to be my total sissy slave forever Donny. My mind said how did we get this far into this, my penis said shut up stupid go with it what else do you have. I found myself on my knees begging her to let me be her sissy slave. I was promising to do and be anything she wanted. Miss Jen looked down on me and said well we must think about how much you are willing to do for me. She went on to say if you start with this you will not be able to turn back. I got to thinking about my life the way it is now. My parents had died in a car accident and I had no other siblings in fact the only relative is a aunt that lived all the way across the country. I truly had no one to be with.
We closed the place and I followed her to her home. We pulled in the drive way and saw the biggest house I had ever seen. When we went inside I was amazed I had never set foot in a house this big. Miss Jen picked up the phone and a lady with a uniform like a maid at the hotel I had seen in the movies. She introduced us Betty this is my new pet, he is a sissy and it totally under my bidding. He will also be assisting you when he is home and I am not using him. I felt like a toy for her and Betty. She told Betty to take the evening off and please come back in a few days. Miss Jen handed Betty several dollars and off she went. Miss Jen said we will spend the weekend training you to be a good girl. I said Okay, she said you mean yes Ma'am, you will never call me Miss Jen again. She said she had some girlfriends of mine coming over to play so you go up stairs I called ahead while you were in the toilet at the shop. I had Betty lay out somethings on the bed in your room. Take a shower and get dressed and don't even think of trying to beg your way out of this do you hear me? I said yes Ma'am what shall I call you she said Ma'am will do unless I want to play other games with you.