I met Philips Dad when he responded to one of my web messages.
I had heard about his son who was doing well, but not well enough, at his 'little rich kids' prep school and so I did a deal. George was looking for a tutor and as I had just left university and don't have a job yet I offered to help out.
I remember George laughing as he delivered an absolute scorcher to my already sore behind and telling me that I had better not go too hard on his son. I think he found the idea of letting me have a 'caning limmit' as he put it, on young Philip, amusing. We agreed that Philip was not to know that I had a limit so as not to let the boy' concentration or effort lapse.
I had been looking forward to today for some time. George had discussed his son during our sessions together. He told me that the boy's backside reddened faster than mine and that Philip did not clench as tightly either. He also said he wanted me to shave closer so that my skin would be more like his son's which was hairless and smooth, even at age eleven.
I was not disappointed. Philip is very good looking and quite slim. Boys who are slim generally have smaller tighter bottoms and I was going to enjoy reviewing his work and punishing accordinfgly.
I loved the way he looked at me as I moved the cane about earlier. He knew he was going to be feeling it.
I also rather enjoyed the inspection routine. His Dad had started doing that to me shortly after we met. It made me feel quite little, as if I was being dressed again like a five year old. I could easily tell, when inspecting the back of Philips trousers that his bottom was a delightful shape for a caning (or a spanking) and envied George the fact that here was a delightful boy that he could punish any time, day or night, whenever he felt like it.
I looked at my watch. Why does the time pass so slowly when you want it to pass quickly. I adjusted my crotch ( I had worn one of my tightest thongs for the occasion), stood up and walked into the study. Philip had his head in his hands. His fringe was falling over his cute forehead. He looked up.
''Is it time already...sir'' he asked.
God he is cute I thought. What a credit to his Dad.
Ten minutes later I looked up at Philip who was reading the spelling list I had given him to learn.
''Get up and come and bend over the front of the desk young man'' I announced seriously. I picked up the cane.
Without saying a word the young boy got up and walked over to the front of the desk. I could tell he was no stranger to this but he had a 'hang dog' expression on his face. I wanted to smile but thought that perhaps I should not let the boy know how much pleasure I was getting form issuing this instruction.
Philip bent over the desk but kept his eyes on me. I sat still, playing with the thin whippy lenght of rattan that George had so kindly provided for me.
Philip kept his eyes on my as he bent over facing me. ''I am not satisfied with this work boy'' I announced. Philips eyes went from mine to the cane.
''I didn't think you would be sir...'' the boy said.
''What did you say Philip!!!!'' I shouted loundly.
The boy became red in the face and said quietly ''nothing sir''
''You will speak only when I tell you and for that rudeness I am going to have to cane you a little harder, aren't I?....answer me boy''
''Yes sir,'' Philip replied but retaining a look of defiance in his expression.
I got up from the desk and wlaked around to the boy.
''Stand up now'' I ordered. As he did so I pulled his trousers up his thin body until I felt that they would not go higher.
''Bend over again'' I told Philip and he obeyed. This time the this grey trousers streched better acroos his small bottom, defining each cheek nicely, a distict cleft between the nice buttocks. I wanted to reach down and foncle the delightful bottom, but decided that as this was supposed to be a serious ounishment that I would not.
I placed the cane across the middle of the bottom than was poking up towards me. Delightful. I pushed the whippy stck across the bottom, knowing exactly how distrubing this feeling is. I kept the cane hard on the surface tracing the boys nice round bottom with it.
I lifted the stick and brought it down, The 'swish' was music, the point it struck Philips young bottom was a crisp 'snapping' sound. The bottom flinced with the pain and a loud 'owwwwweeeee' sung out from the pretty boys lips. I loved it.
The boy kept his position. George had told me he would but that if Philip did touch his bottom I was to be careful as in all the years that Philip had been spanked and caned, he had learnt that it was unacceptable to touch his bottom until he was told he told do so.
I delivered the next five strokes slowly, loving every second. Philip did not know of the agreement with his Dad which gave me a 'caning limit' of six strokes each day. I had used them up quickly on day one because I was so keen to cane the young boy. I wondered how long it would take the boy to work out that he would receive six whacks each day of the holiday. After today I planned to spread them out more.
I kept Philip bending over the desk longer than necesarry so that I could admire the shape of his bottom for longer. I walked around to the front of the desk with cane in hand and saw that Philip was crying gently.
I looked at the boy and he looked up at me. The caning had clearly hurt him.
''I think you had better try harder with your spelling test. You have another twenty minutes to learn them, now get up and return to your chair'' I ordered.
Philip stood up slowly, pulled his trousers back down a little so that they were not so high up between his legs and walked, a little stiffly I thought, back to his chair. I knew very well how it felt to sit on a hard wooden chair after six whacks with a thin rattan cane and I felt for the child as he sat down cautiuosly and whinced as his bottom met the seat of the chair.
I know he saw me grin as he looked up at me with tear stains on his face. Well there was nothing he could do about it. He picked up the spelling book and stared at the words. His bottom must have been stinging and it is difficult to concentrate in that state.
I went off to the bathroom to change my thong for a new one and went back to watch more TV.