This fantasy (which I have realised more than once) stemmed from an actual experience in boarding school.

In about 1952, and aged 10, I was at a boarding school where the headmaster's leather slipper was in frequent use. Although pillow-fights were banned, we used to have them anyway in our dormitory of 10 boys -- but, on this one occasion, we were caught by the matron, a formidable and controlling woman. She sent one of the boys to ask the headmaster to come up to the dormitory and, guessing the purpose of the request, he brought his trusty slipper.

The matron was a much stronger character than the headmaster; so it was clear from the start that she was controlling the proceedings. We were all made to drop our pyjama bottoms and bend over the ends of our beds. We each got 4 hard whacks and there was a lot of howling and kicking of legs. My main recollection (apart from the pain, which was NOT enjoyable!) was of the matron, standing in the centre of the dormitory with her arms folded as she watched the headmaster progressing through the upturned behinds. Her expression was of simple satisfaction.

I told this story to my Mistress, who quickly understood that the image of the matron supervising discipline was a turn-on to me. The next time I visited her, she stopped me at the door and told me that we were going on an expedition. We got into a taxi which took us to a house I'd never seen before. I was told not to speak -- just to do as I was told. When the door opened, I saw a tall man in his sixties. My Mistress explained that she had brought me to him for a good caning. Without looking at me, he said that he would be happy to oblige. He led us to his study, where he took off his jacket and picked up a serious-looking cane. My mistress instructed me to drop my trousers and position myself over the desk. She came round behind me and sharply lowered my pants. "Please administer 12 hard strokes" she said -- and then stood back, arms folded, to watch the sentence being carried out. Just like my dormitory slippering, it hurt like hell -- and at the time I got no pleasure out of it. But, as we made our way back in the taxi, I was on a real 'high'. I was back there for another dose the following month!