The number of guys who read these stories has obviously doubled recently because I have now had a second e-mail. This guy poses the question – have I ever had a request from a parent to cane a lad for something not connected with school? What a fascinating question I hear you all shout while trying to stifle a yawn. Well, that set me thinking and I had to put my glass of sherry down – the first today, you understand - while I rummaged through my memories.
There was one interesting instance of the above that comes to mind. I once had a visit from a Mr Knight whose son had been at the school for five years and was now in his first year in the sixth form. Now Mr Knight was a wealthy businessman who owned a chain of shops in the county. He sold beds and had the slogan – a good nights sleep with a good Knights bed! He doted on his boy, Simon, and I am not surprised because Simon was a lovely lad. He was a cute, tall lad with blond hair. I had caned him just once or twice for small misdemeanours in the past – but then everyone gets it sooner or later. I pity the poor lad who goes through his school life without ever experiencing the cane on his bottom. It is what they call a rite of passage. Now that caning has unfortunately been abolished in schools and discipline has suffered as a direct consequence – I read only a few days ago that some schools are even having to buy expensive scanners so that they can see if their pupils are carrying knives or guns to school! Can you believe it? In addition I am now seeing guys who have never been caned at school but who want to see what it was like! I digress again – perhaps it is the effect of that second glass of sherry....or is it my third? – so easy to lose count.....
I am beginning to recall the interview very clearly now. Mr Knight had made an appointment to see me one Monday morning early in the first term of the school year. I wondered what it could be about and I soon found out. Mr Knight was terribly concerned about his sons spending habits. He gave him a generous weekly amount of pocket money and he had a fair sum deposited in his post office savings account. At the end of every week the boy had not only spent all his pocket money but had dipped into his savings account so that there was virtually nothing left. Mr Knight was a successful businessman who had always been very careful with his money. He had built up this business so that he was now quite wealthy. He was upset that his son seemed to have no understanding of the value of money and feared that he would eventually go through all the fortune that he had built up over the years. He wanted me to help him as the boy had a great deal of respect for me as his headmaster. He also added that I could employ any punishment that I saw fit if the boy did not keep to the guidelines that I laid down. I perked up at this and I said I would think about it and I would try to help.
I sent for young Simon and told him what his father had said and asked him what he had to say about the matter. Simon just grinned and agreed that he was just hopeless when it came to money matters because it had always come so easy to him. That gave me an idea.
"Right," I said, " this is not a school matter but a private one. You will come to my cottage every Sunday. I will tell your father that he is only to pay you your regular pocket money once you have earned it and you are going to earn it by having to do chores around my cottage. In addition you are to make a list of your daily spending and keep it in an exercise book that I shall give you. You will deduct at least ten per cent of what you are given to be put away in your post office account and the rest of your money is to be divided up into seven – each day that you overspend your amount you will be punished. Understood? Report to my cottage this Sunday at nine oclock and be punctual. You may go."
Simon was not overjoyed at hearing all this but did not argue. He merely nodded his head in agreement and turned to go. I then eyed his figure from behind and decided that this could be fun.....
Sunday came and nine oclock rang out but there was no Simon. Fifteen minutes later and still no Simon. At nine thirty there was Simon looking rather dishevelled and a bit out of breath. "I am very sorry I am late, sir. I went out last night and overslept this morning."
" How unfortunate for you," I said. " We shall start the day off then with your being punished for lateness."
Simon did not look too happy at this turn of events but merely nodded his head and mumbled, "Yes, Sir."
"You are going over my knee to be spanked but first I want you completely stripped. Take all your clothes off and put them neatly over that chair."
Simon was not a very happy chappie. "Take them off, Sir? All of them?"
"You are not going deaf are you, boy? Take them off – all of them!" and Simon obeyed – rather reluctantly. Off came his tee shirt, off came his vest, off came his socks and shoes, down came his trousers and he was left standing in his white underpants when he hesitated - but as he could see that he had no option he slipped those off as well and he stood in front of me in all his glory. He was indeed a very well endowed young man and I realised that I was going to enjoy this regular Sunday meeting.
I sat myself on a high backed chair and I beckoned him to approach me and I put him over my knee so that his nice round bottom protruded nicely in the air. I felt both buttocks with my hand before I started to spank first one side then the other. I kept this up for quite some time until both buttocks had turned a lovely shade of red and he was beginning to squirm under the constant spanking that he was getting. When I felt he had enough for time being I told him he could get up. He stood up and rubbed his bottom for a while and then automatically went over to his clothes.
"I did not tell you to get dressed," I said.
"Sorry, Sir," he apologised and dropped the piece of clothing that he had taken. He stood still and waited for my next instruction.
"Let me see the exercise book I gave you where you have written down your daily expenditures."
He handed me the exercise book and I could see that he had neatly written down his daily expenditure.
"Show me your post office book so that I can see that you have deposited ten per cent of your pocket money."
"I am sorry, Sir. I went out last night and spent more that I had intended and I have nothing left over."
"In that case, I am going to cane you so that you will remember next week."
Simons face drained in colour and he was almost as pale as his blond hair. I ignored this fact and put two ordinary chairs back to back.
"I want you to kneel on this one, my lad, and I want you to bend over the backs of the chairs with your head down on the seat of the other chair."
The boy did as he was told and the effect, of course, was that his nice bottom was raised high in the air ready to receive my full attention. I then delivered six nice whacks across his pale buttocks and six lovely red lines appeared of their own accord! Simon was not used to this treatment and he yelled as each blow landed. He wriggled a lot as well - but made no attempt to get up until I allowed him to do so. He then rubbed his bottom vigorously.
"I enjoyed that," I said rubbing my hands with glee. "Now you can put your pants and trousers back on and go and wash my car."
"Yes, sir," mumbled the rueful Simon and I provided him with a sponge, leather and a bucket of water and let him get on with it. In fact, he worked hard and did an excellent job. When he was finished I poured us both a cup of hot coffee and we sat and chatted. I then decided that I would spank him some more and I ordered him to strip again and go over my knee. This time he took his clothes off without any hesitation and he was quickly over my knee. I felt his smooth buttocks and gently traced the curves down one side and then down the other. I could feel him getting harder. His bottom had resumed its former creamy colour although I could still make out the six red lines that the cane had imprinted. I spanked him nicely until his bottom was a nice bright red in colour. I then told him to get dressed and I would see him every Sunday for the same or similar treatment.
This went on for the two years that he was in the sixth form and we developed a nice bond over those two years. How successful was I? Well, I had quite an effect on him but not in the way that his father wanted! He never learned how to handle his finances. He was and is always in debt. When his father retired he did not give his business over to his son and was very wise in my opinion not to do so. He sold up and gave his son one quarter of what he realised but with this money he bought a property for his son so that he would always have a roof over his head and of course when Mr Knight eventually dies Simon will inherit the rest. In the meantime Simon has accrued debts from student loans, credit cards and numerous friends who were silly enough to lend him money. The one thing that Simon did learn from his weekly visits was that he loved being spanked and caned. He now goes to spanking clubs and sees various gentlemen who give him the punishment that so excites him and from time to time he even visits me just so that he can go over my knee for old times sake!