My Mother’s Sissy

                My mother was not a willing participant in my conception; and while she never held it against me, it was always obvious I was not a ‘wanted’ child. Being born a boy certainly didn’t help either. My mom was always on me about not trying to act like a tough guy, and several times flat out admitted she would prefer I was a girl.

                By the time I was thirteen I was so stressed out by my life that I was wetting the bed nightly – another terrible MAN PROBLEM according to my mother. Regular beatings and forced diapering did nothing to help… but that didn’t stop her from trying. I learned to accept it as a part of my already messed up life. Then everything changed.

                “Absolutely not!” My mom yelled as she stared at me furiously. She had just walked in on me masturbating and this was more than she could take. “I WILL NOT have a dirty, nasty sex fiend man living in my house!” What followed next was the most brutal beating of my life, and much of it is to this day is blacked out in my mind. At some point I must have passed out, as it was the next morning before I awoke.

                I was on the floor, mostly naked, laying in a puddle of my own urine. I felt a tightness around my waist and looked down. I had a thick leather chastity belt on, pressing my penis uncomfortably against my body. Slowly, painfully, I got to my feet. I was dizzy and could see bruises on my legs and thighs from the beating I had taken the night before.  On my bed was a pair of jeans and a white blouse; along with a bra and white cotton panty. I left them there and instead went to my closet. It was empty. My dresser too. All my clothes were gone. I looked again at the bed and sighed.

                I stared at the outfit for a good ten minutes, shivering in my near-nakedness. Finally I picked up the bra and put it on. It was clearly designed for a guy as it’s cups were completely filled and the tag read “From He to a B.” At least she went with a modest size I thought with a burst of silent laughter that surprised myself. I picked up the panty, but found it to be more than I could deal with. Instead I reached under my nightstand and pulled out one of my night diapers and leaning against the wall, put it on. The blouse was next, and finally the jeans, which had some padding in the thighs and backside to fit more like a lady. I looked at myself in the mirror and had to smile. I was a cute girl, and my short haircut was surprisingly passable as a girl’s. Somehow the outfit felt and looked right on me. I mean, I had never really been a man’s man, but I hadn’t considered becoming a girl either.

                About that time my mom came into my room carrying a tray with cereal and juice on it. She looked at me and smiled, then looked at the bed. “Why didn’t you put the panty on?” She asked with an even tone.

                “I…uh… prefer the diapers.” I admitted shyly. She nodded and set the tray down on my bed. Then she came over to me and gave me a big hug “You’re going to be my little princess for now on, aren’t you?”

                I thought for a few seconds, and then answered. “Yes Ma’am.”

                Over the next few weeks my mom and I had a great time shopping for new clothes, and building a better relationship. We agreed that I could wear diapers instead of panties; and that bedwetting would no longer be a punishable offense.  She showed me how to apply make-up and how to walk and talk more femininely. As the summer turned to fall we started to build our story, knowing we’d have to get it right.

To Be Continued.