A mother looking for a school for her son has a strange request. By a new writer to us.

By Ricky Richards

It was a late June morning in 1956 and John Jackson, Headmaster of Westwood School, was feeling contented. The term was coming to an end, only Speech Day to get through, and applications from parents who wanted to send their sons to his school looked very promising. He had interviewed several prospective parents already this week and was sure they had been impressed. There was a knock on the door.

“Come in,” he called, and his secretary, Mary Fitzpatrick, a very slight and demure 25-year-old, entered.

“Mrs Robinson is here to see you, Headmaster.”

John had forgotten there was one more parent coming to see him that morning. “Ah,” he said, looking at his watch. “Please send her in.”

Mrs Robinson came through the door and John stood up to greet her. “Good morning, Mrs Robinson, how nice to meet you. Has my secretary given you a coffee?”

“I’ve been very well looked after, thank you, Headmaster.” She had a low voice and a tanned figure, which suggested either lots of foreign holidays or lots of sunbeds. She was blonde, slim, mid-thirties, wearing a long summer floral dress.

“Please take a seat, Mrs Robinson,” said John.

“Please call me Karen, Headmaster,” she said.

“Right, said John. “Let’s get started. I gather you are interested in sending your son here the year after next?”

“That’s right,” said Karen. “I’m a single parent and feel that a good boarding school can offer more than I can. I’ve asked around and everyone speaks very highly of you and your school; your exam results are clearly very good and your fees compare well with those of other schools in the area.”

“That’s very good to hear,” said the Headmaster. “So what other information can I let you have?”

“Well,” said Karen, “I was wondering about things like pastoral care, attitude towards bullying, discipline and so on.”

“Ok,” said John. Bullying is not tolerated at all and perpetrators will be severely punished. Fortunately, it hardly ever happens.”

“And what form does the punishment take?”

“Well, for minor misdemeanours there is usually detention or litter-picking in the grounds of the school. For the very rare cases involving, what shall we call it, acts of immorality, like bullying, cheating or gross behaviour, then corporal punishment is the ultimate sanction.”

“You mean, you whack the boys or something?”

“Well, yes, but it’s rather more technical than that. I have a cane and I usually deliver three strokes.”

“On the hands?”

“Absolutely not. Only on the bottom. Caning pupils on their hands is hideously painful and can result in long-lasting injury. No, they bend over, touch their toes and receive, usually, three strokes. This is painful, but because it is the final sanction and happens only two or three times a year, it is essential that it should hurt; it is both a deterrent and a punishment, and something which I think all parents can understand. But I must stress that it is highly unlikely that I would ever have to cane your son.”

“Do you think I could have a look at the cane,” said Karen.

“Of course,” said John, and walked over to a cupboard before extracting a standard three-foot slim and whippy cane.

“Not a crook-handled cane, then,” said Karen.

“No, they are more just for show and probably instil more fear than pain. But actually, they are rather impractical. However, if you are still worried, I can show you the punishment book in which all canings are recorded and which is regularly inspected by the school’s governors.”

He opened his desk drawer and handed Karen a large leather-bound book. She started looking through it.

‘He is quite right,’ she thought, ‘he really doesn’t seem to cane boys very often.’ She glanced through the names and the offences. Most of them were three strokes of the cane for bullying, or cheating, or swearing at a teacher.

“So, anything else you would like to know?” asked John.

Karen was silent for a minute, considering. Then she said, “Headmaster, I’m still interested in the caning procedure. Is there any special technique involved?”

“Oh, indeed,” replied the Headmaster. “You have to take into account a number of things. Firstly, what size is the bottom? If it’s very small, great care needs to be taken not to strike too high or too low. I always try to make sure the strokes do not fall on top of each other, which was not always the case, I may add, when I was at school. The tip of the cane must not wrap itself round to the hip, because this would cause unnecessary distress. I usually bend a little myself to make sure that the stroke arrives horizontally, which is also very important.”

“My goodness, you make it sound quite a science!”

“Well, it is, actually,” he replied. “It should be a very painful short, sharp shock with no prolonged after-effects. Mind you, the stripes will usually last two or three days. Again, if I recall my own schooldays, there is quite a cachet to wandering into the showers sporting well-bruised buttocks, and I have no doubt the same thing applies here.”

Karen sat for a bit in silence, biting her lower lip. Then she spoke.

“Headmaster, would you think it really weird of me if I asked you to cane me? I feel I need to know what I may possibly be letting my son in for. He has never even been mildly spanked.”

The Headmaster was amazed. “This is a most unusual request, but, if you are absolutely sure, maybe just one stroke to give you an idea? It can’t do too much harm. Normal strength?”

“No, a proper caning, please, Headmaster. The usual three whacks. It is important for me.”

“Well, you know best, though it is highly irregular, but it will hurt if I do it properly.”

“I know. So what should I do now?”

“I want you to go to the middle of the room, bend over and touch your toes.”

Karen did as she was bid, her flexible body having no trouble with touching her toes, her bottom sticking out.

“Ah,” said John. “I think we have a problem. Your long dress makes it difficult for me to see properly or to aim properly and it is important not to strike you too high or too low.”

“Shall I take the dress off, then?” asked Karen.

“If you are happy to to so, it would make things easier,” replied John.

With her back turned to him, Karen pulled her dress off over her head and bent down again. John was met with the sign of a very small, pert bottom clad just in skinny knickers.

“Ready, then?” he asked. “You realise your bottom is very small, but I will be as accurate as I can.”

“I think so, now or never,” came a somewhat anxious reply.

John raised the cane to shoulder height and swished it across the middle of Karen’s bottom.


The effect was electric. Karen leapt up with a howl of pain. “Ow, ow, ow,” she shrieked, clutching her buttocks, and hopping up and down. “My God, that stings,” she said, rubbing her bottom. “I didn’t realise how much it would hurt.”

“I did warn you,” said John. “So, I guess you will want to call it a day now?”

“Yes,” said Karen. Then, as the sting subsided to be replaced by a warm and quite pleasant glow, she added: “No, I asked for three so I will take three. As the man said, I’ve started so I’ll finish.”

She bent over again, touching the floor, her legs slightly apart this time, and said, “I’m ready.”

“Very well,” said John, “But this time I would like you to stay for the remaining two strokes. If any boy stands up during a caning, he gets an extra stroke.”

He once again raised the cane and slashed it across Karen’s bottom, an inch or so above where the first stroke had landed.


Karen gave a muffled cry, waggled her buttocks desperately but managed to stay in position this time. She awaited the final stroke, scarcely breathing, dreading the pain but at the same time somehow feeling a frisson of excitement at the thought of of bending over in front of this good looking man. John took aim, a little lower this time.


Karen’s whole body trembled; she stayed bending over, absorbing the pain flooding through her bottom. She was experiencing feelings unlike any other she had ever known.

“Well done,” said John. “You can stand up now.”

Karen stood up, facing him, rubbing her buttocks. “That was unbelievably painful, Headmaster. But I’m glad we did it.” As the immediate sting ebbed away, she said: “It is an amazing punishment. But I think it is not disproportional if somebody has behaved very badly.” She stroked her buttocks over her knickers, feeling the raised weals. “I can’t wait to get home and look in the mirror and see what my bottom looks like.”

“Is there anything else you would like to ask or find out about, Karen?” asked John. “Maybe my secretary could show you round the school for a while.”

He rang for her. His secretary came in. He wondered if she had been listening. “Could you show Mrs Robinson round the school for a bit, please, and then please bring her back her before she leaves.”

The door closed and John sat down, exhilarated but astonished by the recent turn of events. An hour later, there was a knock on the door and Karen was shown in.

“Most impressive,” she said. “I’m sure my son will enjoy it here and will thrive. And I hope for his sake that he does not get caned.”

“I’m sure he won’t,” replied John. “How is your bottom now?”

“The sting has almost died away now. But it still feels very hot,” she said. “Anyway, I had better leave you in peace. There may be other parents wanting the same treatment!”

“Highly unlikely,” said John. “But it was a pleasure to meet you.”

“Thank you,” said Karen. “Perhaps we can meet again? Socially, maybe? Oh, I forgot, you may have a significant other?”

“I don’t, in fact, and that would be very nice,” said John. “Maybe at the weekend sometime. Have a drink somewhere.”

“I have an even better idea. I’m on my own at present. Why not come round on Saturday and I’ll cook you a meal. You bring a bottle of something, preferably dry and white, and I’ll do the rest.”

“It’s a deal. I shall look forward to it.”

“Me, too,” said Karen. “And maybe you can check at the same time to see how my stripes are progressing?”

The End

© Ricky Richards 2018