She knew how the red line would quickly appear and that the hardened ridge would soon follow. She had seen it develop so often on so many bottoms. Now...though she could only feel the pain and knew Chloe would be the one enjoying the sight she was used to seeing. Worse was the humiliation of being caned by a woman so much younger than herself. Was it wrong or right though? Did age matter where discipline was concerned? Maybe not she supposed. As the second stroke landed Miss Castle’s mind was. I started to buy panties, stockings, bras, etc. and wear them at home. I was still living with my parents at this time and had to take care not to let them see what I was enjoying. I would dress up and get into bed at night and wank my self silly, fantasising that I was a woman and men wanted to fuck me. But it took a couple of years for me to pick up the courage to go out wearing undies and show myself to men.When 18 years old I went out one night with my undies on underneath my normal. More

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