Another head girl in trouble with her headmaster – and her mother too!

By Kenny Walters

“Jessica! Two girls on the end table messing about.”

“Yes, Charlotte.”

“Henrietta! Can we hurry the third form on a bit, please.”

“Yes, Charlotte.”

The head girl waited and watched until all the girls were seated at their refectory tables and the second lunch service could begin.

“Sarah, could I have a word please?”

“Yes, Charlotte.”

“Sarah, could you take over from me for a while, please?” Charlotte Tomkinson spoke quietly to the slightly shorter, slightly curvier girl with the red hair that now stood in front of her.

“Yes, of course Charlotte.” Sarah Matthews, the deputy head girl, looked puzzled. “Problem?”

“No, nothing.” Charlotte reassured the other girl. “Just got to pop along and see Mr Withers. I shouldn’t be long.”

“Oh, right.” Sarah watched as the tall, dark-haired girl walked away, still somewhat bemused her colleague on the high table of the prefects’ common room should be going off to see the headmaster right in the middle of supervising the lunch service.

* * *

“But it was a complete accident, headmaster.”

“I know that, Charlotte.” The fifty-something headmaster leaned back in one armchair while the attractive head girl sat on the edge of an identical armchair on opposite sides of the fireplace and comfortably away from the working area that surrounded his large desk. “But, when I go to explain exactly why I’ve had to authorise a rather large bill for repairing a torn oil painting the governors are going to want a culprit.”

“Well, yes, of course you must tell them it was me.” Charlotte frowned, not seeing the difficulty. “And obviously you must give them my sincere apologies when you explain it was an accident.”

“Ah, but you see, Charlotte, they’ll want to know why you took the painting down in the first place. That being totally against school rules, of course.”

“Is it? I didn’t know that.” Charlotte continued frowning, an expression that did nothing to detract from her intelligent good looks.

“Oh, indeed it is, Charlotte, indeed it is. Right where it says girls shall not remove, interfere with, or deface school fixtures and fittings.”

“But I only took it down because we were holding a dress rehearsal for our 1960s jazz revival concert and a portrait of Miss Dawkins-Henderson, headmistress from 1954 to 1989, seemed rather overly sombre and inappropriate. It was hardly my fault a music stand fell over and slashed the painting. If it had been a better portrait, I wouldn’t have needed to take it down.”

“It is, I am told, a particularly accurate representation of our formidable and much beloved predecessor, Charlotte.”

“She must have been a fierce old cow, then.” Charlotte exclaimed without thinking.

“Charlotte! That will do! In the situation you are in, I hardly think it’s a good idea to add insult to injury by insulting the good Miss Dawkins-Henderson deceased.”

“Situation? What situation?”

“The matter of appropriate punishment, Charlotte.”

“Punishment! What punishment? For a total accident?”

“Of course, things aren’t helped by the fact it was your music stand that fell and damaged the painting. That is so, isn’t it?”

“Well, yes headmaster.” Charlotte admitted. “But that still doesn’t mean I meant to rip the damned painting with it.”

“Language, Charlotte!” Mr Withers cautioned with a raised voice.

“Sorry, headmaster.” Charlotte took a deep breath and calmed herself down. “Okay, so what is to be my punishment, headmaster?” The look on the head girl’s face left no doubt that she felt any penalty was totally unnecessary. “I’m sure you are quite aware it is going to be absolutely humiliating for me to have to perform some menial task in front of the other girls.”

“I’m not so sure we’re talking about half an hour picking up litter in the school grounds, Charlotte. I’m aware you regard this as a trivial matter by your attitude during this conversation. However, the governors and I regard the expenditure of nearly two thousand pounds as far from trivial.”

“Two thousand pounds! That’s more than the damn thing is worth, headmaster.”

“To the school, it is priceless, Charlotte. It is the only portrait we have of our dear beloved Miss Dawkins-Henderson.”

“I’m not sure ‘beloved’ would be the description some of our old girls would use, headmaster.” Charlotte retorted. “Anyway, I’m certain my parents would be quite happy to reimburse the school. I’ll have a word with my mother.”

“That might help, Charlotte. However, it is still money being spent needlessly and the governors are going to need to know the matter has been suitably dealt with.”

“That I’ve been suitably punished, you mean.”

“Exactly, Charlotte.”

For the second time, Charlotte took a deep breath to pacify her annoyance. “Okay, headmaster. Tell me. What is my punishment to be?”

“I’m afraid there’s going to have to be a smacked bottom, Charlotte. A fairly firmly smacked bottom.”

“What!” Charlotte looked at the headmaster incredulously. His solemn thoughtful expression left her in no doubt he was being completely serious. In case there had been the slightest uncertainty, Mr Withers nodded gently. “No way! Definitely not! Not for a complete accident.”

“That might make your continuing at this school somewhat doubtful, Charlotte. Of course, that would be up to the governors, not me, to make that decision.”

“You’d expel me? Over something as trivial as this?”

“You might regard the matter as trivial, Charlotte. That, as I hope I’ve already indicated, is not how I or the governors see it.”

“But I’ve already said my mother will sort out the bill for the repair of the painting. Surely that’s an end to the matter.”

“And as I have already said, that is a gesture that would be much appreciated but it would not absolve you from the need to be punished for your wanton carelessness. You should not have taken the painting off the wall in the first place, but having done so the very least you could have done was to take all necessary steps to ensure no harm could come to it.”

Charlotte sighed as her mind battled against the brick wall presented by the headmaster, a barrier that all her arguments seemed unable to surmount. This was supposed to be her glory year, a year spent as the most senior girl with all the benefits that position gave her. Now, it seemed, all her years of exceptional hard work were in danger of being thrown away, all for the sake of one stupid painting she loathed the sight of anyway. There was just one approach left.

“Okay, headmaster, I accept I was wrong to have taken the painting off the wall and I accept it was my responsibility to take care of it. I failed. Therefore, perhaps I should face some punishment.”

Charlotte paused. The next bit was going to be hard. Mr Withers sat with his chin raised, feeling he had at least won the head girl partially over to his way of thinking, yet not at all certain what precise thread she was taking.

With her thoughts together again, Charlotte continued. “If I were, as you put it, to have my bottom smacked, which you say is the only course of action the governors would accept, what exactly are we talking about here? I mean, what is the exact nature of the punishment you are proposing?”

“A fair question, Charlotte.” The headmaster replied, feeling inwardly he was winning the battle. “We’d have to be thinking about the traditional six. With the cane, of course, in view of the seriousness of the offence.”

If the headmaster was expecting the head girl to be dismayed by the very mention of six strokes of the cane, he was to be disappointed. Charlotte took the information totally in her stride, her mind focusing far more on the words ‘have to be thinking’ and noting the cane had been mentioned more as an afterthought, even if the headmaster hadn’t been able to resist reminding her how seriously the matter was being regarded.

Charlotte nodded gently as she mulled over her proposed punishment, while Mr Withers seemed slightly the more anxious as he awaited Charlotte’s reaction.

“And what sort of announcement would be made about my punishment, headmaster?”

Mr Withers smiled inwardly, sensing he had the measure of Charlotte’s thinking. “Oh, I hardly think an announcement would be needed, Charlotte. No, I think this is a matter best resolved behind closed doors, so to speak.”

“I think I would like to speak to my mother before I come to a decision, headmaster.”

That surprised Mr Withers and he could only reply with some stuttering. “Oh! Oh, yes. Well, I’m sure that would be fine, Charlotte. Yes, indeed.”

* * *

“Hello mummy. How’s things?” Charlotte looked around as she spoke on the telephone, anxious not to be overheard even though Mr Withers had left her alone in his office to make the call. Charlotte explained her predicament with the oil painting as rapidly as she could and was able to avoid much of her mother’s anger at being landed with the bill for repairing the damage by simply not mentioning the amount. The next bit might prove a little trickier.

“Now, I know I’ve been a silly girl, mummy, and I know I should never have taken the wretched painting off the wall, but, well, perhaps you’ll be less angry with me when you know I am going to be punished for it because that’s only fair.

“How? Oh, I don’t know. Some awful task, I expect. Picking up litter or running round the playing field umpteen times, you know the sort of thing. It will be something horribly public and humiliating.

“Yes, I know it would be terribly embarrassing for someone in my position. But, that’s the punishment, of course.

“Yes, I know it will affect my standing with the other girls but what else can I do? I have to be punished. That’s only fair. Actually, that was something I wanted to ask your advice on.

“I was wondering, mummy, whether you’d agree to my letting Mr Withers give me a private dose of the slipper. You know, a quick short sharp shock. That sort of thing. Then I would avoid the public humiliation and keep the respect of the other girls in one foul swoop. What do you think?

“Oh, I think Mr Withers would agree, mummy. I know he’s rather opposed to using corporal punishment but if I just asked for three whacks I think I might be able to persuade him.”

“No, I don’t mind, mummy. It will be better than being publicly humiliated and anyway I think I probably deserve a smacked bottom for being so silly. Don’t you think so?”

“No, leave it with me, mummy. Mr Withers has had to go off and deal with something or other. When he gets back I’ll explain everything. I’ll tell him you’ll sort a cheque out in due course. Think of me when I’m having my bottom smacked, won’t you?” Charlotte giggled. “Thanks, mummy. ‘Bye.”

* * *

Charlotte replaced the receiver and took a few minutes to work out her plan of action. When she was ready, she opened the door and invited Mr Withers in so they could continue their conversation.

“So, Charlotte, how do you feel now you’ve had a chance to talk things over with your mother?” Mr Withers resumed as they sat down in the armchairs again.

“Well, as you can imagine, headmaster, mummy was not best pleased. It took quite a while for me to placate her, I can tell you.”

“Right.” Mr Withers said, uncertainly. “So how do we stand? If I may put it bluntly, do we sack you or whack you?”

Charlotte swallowed. “Firstly, headmaster, I’ve asked my mother to send you a cheque for two thousand five hundred pounds. That should pay for the repairs to the painting and leave something over for the school to spend as it wishes. Perhaps we could call it compensation for my stupidity.”

“That’s very generous, Charlotte. I must write and thank your mother for her kindness.”

“Oh, that’s not necessary, headmaster. She can afford it and she’s only too willing to try and make up for the silly thing I did.” Charlotte risked a gentle smile; she’d worry about how to clear this with her mother later.

“Yes, Charlotte, but our conversation wasn’t just about compensation, was it?”

“Sorry, headmaster?” Charlotte asked innocently.

“Your punishment, Charlotte.”

“Ah, well that was a bit trickier, headmaster. You see, my parents and especially my mother are very against corporal punishment. That’s really what the extra money is for. I’m sure they’ll have me doing all sorts of things around the house during the spring holiday so as to punish me then.”

“I’m not sure that will suffice, Charlotte.”

“That’s exactly what I told my mother, headmaster.” Charlotte spoke up before Mr Withers could say too much. I pointed out that any other girl in the school would not have been let off that lightly and that there should be no special treatment for me just because I’m the head girl. So, reluctantly, because she is so against corporal punishment, I was able to finally persuade my mother to allow me to receive three whacks with the slipper. It took a lot of doing, headmaster, but she did finally agree to that.”

“I see.” Mr Withers considered thoughtfully. “I see. I have to say three whacks with the slipper doesn’t seem a great deal for wrecking a very valuable painting, Charlotte.”

“No.” Charlotte answered equally pensively. “But then the school is getting somewhat more than simply the cost of repairing the painting, headmaster.”

“So it is, Charlotte. So it is.” I think I need to reflect on this, Charlotte. Come and see me after school tomorrow and I’ll let you have my decision. If I accept your argument, you will receive your punishment then.”

Charlotte was clearly disappointed. “Can’t I have my whacking now, headmaster?”

“No, Charlotte. It will keep until tomorrow.”

* * *

“Is he in?” Charlotte entered the school secretary’s office and cast her question breezily to Mrs Thomson who was busily tapping away at her computer keyboard.

“Yes, they’re all ready for you, Charlotte.” Mrs Thomson answered without looking up.

Even as Charlotte tapped on the headmaster’s door and heard Mr Withers’ voice calling her in, she reflected that Mrs Thomson had used the word ‘they’ not ‘he’. Too late, Charlotte had opened the door and discovered the headmaster in conversation with her mother.

“Mummy! What are you doing here?”

“Pull up a chair and join us, Charlotte.” Mr Withers motioned the girl to fetch a small chair standing in the corner, the headmaster and Charlotte’s mother occupying the two armchairs.

Mrs Tomkinson spoke first before anyone else had the chance. “I’ve come along, Charlotte, because when Mr Withers telephoned me to thank me for my very generous assistance I didn’t have the faintest idea what he was talking about. There seems to be some sort of misunderstanding all round. Perhaps you can enlighten us, Charlotte.”

“Well, mummy, I just said that you’d be willing to pay for the repairs to the painting I damaged and that perhaps there might be a pound or two left over for something the school might like to spend on a little treat or something. That’s all.”

“I see.” Charlotte’s mother seemed far from convinced. “And this business about the slipper, Charlotte. As I understand it, Mr Withers wanted to punish you with litter picking duty or some such, but you were going to ask him if he could slipper you instead. Is that right? I think you had in mind three whacks.”

“Um. I think three whacks were mentioned, mummy.” Charlotte spoke rather quietly, and coughed when she felt a tickle come to her throat.

While Mr Withers sat looking somewhat bemused, Charlotte’s mother dominated the conversation. “So, just how much is this painting going to cost to have repaired, Charlotte? Do you know? Have you been told?”

“I’m not sure, mummy….”

“Nearly two thousand pounds, Mrs Tomkinson.” Mr Withers interrupted Charlotte.

“Two thousand pounds!” Charlotte’s mother exclaimed. “And just how generous was I going to be giving the school ‘a little treat’ as I believe Charlotte put it?”

“Two thousand five hundred pounds was the figure Charlotte suggested, Mrs Tomkinson.”

“Was it indeed, Mr Withers?” Mrs Tomkinson gave Charlotte a cold sideways glare. “Something else I don’t understand, Mr Withers. Three whacks of the slipper seems a mighty small punishment for causing damage that will cost nearly two thousand pounds to put right.”

“I think I can enlighten you a little further, Mrs Tomkinson. The punishment I proposed was six strokes of the cane. Charlotte sought to reduce it to three of the slipper in return for your generosity over the compensation.”

“The generosity attributed to me that I was not aware of, you mean Mr Withers?”

“Apparently so, Mrs Tomkinson.”

“Do you have anything to say, Charlotte?” Mrs Tomkinson turned to her daughter.

“You can’t blame me for trying, mummy. Anyway, you’re always telling me to be creative and resourceful.”

“It goes without saying, Mr Withers.” Charlotte’s mother reverted her attention to the headmaster. “Charlotte will be accepting the punishment you offered her, plus two extra strokes for her attempted deception.”

“If that is what you wish, Mrs Tomkinson.” Mr Withers looked towards the lady’s daughter. “Charlotte?”

Charlotte nodded reluctantly.

“One other thing, Mr Withers.” Mrs Tomkinson continued. “Would you mind if I were present when you punish Charlotte?”

“Not at all, Mrs Tomkinson.” The headmaster replied, looking towards Charlotte.

“Oh mummy! That’s too awful!”

“Good!” Charlotte’s mother ignored her daughter’s protest. “That means we can follow the good Miss Dawkins-Henderson’s ideas when you administer the caning. It seems admirably appropriate in the circumstances.”

Both daughter and headmaster looked baffled.

“Of course.” Mrs Tomkinson chuckled to herself as she recalled her time at the school under Miss Dawkins-Henderson’s stewardship. “Neither of you will know what that means.”

“Charlotte, do you have decent underwear on, or are you wearing one of those dreadful thong things?”

“Mother!” Charlotte blushed again.


“Sort of brief panties actually.”

“Good! That means you won’t have to go and change.”

“Mummy. No, please.” Charlotte believed she had a fair idea of what her mother had in mind.

“Mr Withers. Are you ready to proceed?”

“Oh, well, yes, Mrs Tomkinson.”

“Then I suggest you give this daughter of mine the well smacked bottom she thoroughly deserves.”

Mr Withers stood up and went across to his desk. Charlotte, twisting round in her chair, watched as the headmaster slowly and methodically cleared the paperwork away into various drawers and a cabinet behind the desk.

“I can’t believe you’re subjecting me to this, this awful ordeal, mummy.”

Mrs Tomkinson ignored her daughter, and Charlotte then had to watch as Mr Withers went across to the far corner of the room and opened the door to a thin tall cupboard. Instantly, she could see about six or seven canes hanging from hooks inside.

“Oh, mummy.” Charlotte wailed as the headmaster selected a long slim cane with a crook handle from a hook near the right hand side of the cupboard and all too soon began to walk towards the two females. He stopped about six feet from them, holding the cane in one hand about half way down its length and balanced almost vertically.

“Charlotte, if you please.”

Charlotte slowly got up, and noticed her mother also getting up out of her chair.

“Please remove your jacket, Charlotte.”

The mood had turned quite sombre as Charlotte slowly took her black jacket off and laid it across the chair she had just vacated, leaving her in her tightish black trousers and a white blouse.

“Now go and stand by the side of my desk, please Charlotte.” Mr Withers commanded.

Even though Charlotte walked quite slowly, the short journey was over far too soon for the tall head girl’s liking. She stood facing the side of the desk, ready to bend across it. To have done anything else would have been quite pointless.

Mr Withers now moved towards her, as Charlotte detected out of the corner of her eye. What she hadn’t realised was that her mother had also come across and now stood directly behind her. Thus she tensed when she heard her mother’s voice.

“This is where Miss Dawkins-Henderson’s bit comes into it, Charlotte. I think you’ve guessed what you need to do.”

“Mummy, this really is too much!”

“Just do it, Charlotte.”

As Charlotte began unfastening her trousers, Mrs Tomkinson turned to the headmaster and explained: “Miss Dawkins-Henderson always felt it was pointless caning a girl across her trousers, or skirt as it was more likely to be in those days. Too much protection, in her opinion.”

Mr Withers didn’t reply, his interest being taken more on the sight of Charlotte pushing her trousers down to her ankles and showing a flash of pale blue knicker material under her white blouse.

With Charlotte now standing tensely straight with just a hint of blue below the hem of her blouse that was just long enough to conceal most of her bottom, Mrs Tomkinson took a step back. “Mr Withers.”

“Yes. Right, Charlotte. Bend over, please.”

Because of her height, Charlotte found it awkward to bend over and get right down onto the surface of the desk but managed the task eventually by tucking her knees in and digging the toes of her shoes into the carpet. This manoeuvre still left the upper half of her bottom covered by the hem of her white blouse, a point noted by Mr Withers even though he found it difficult to find the words to point this out. Thankfully, Mrs Tomkinson came to his rescue.

“You’ll need to fold the back of your blouse up out of the way, Charlotte. Otherwise, the cane might strike you on your blouse rather than your knickers, and we can’t have that, can we?”

As Charlotte made the necessary adjustment, Her mother again turned to the headmaster and commented: “That was another of Miss Dawkins-Henderson’s little foibles, Mr Withers. She always made the girl prepare herself for the punishment. She used to think it concentrated the girl’s mind on what was about to be done to her, and why it was being done.”

With Charlotte’s pale blue panties now fully exposed, not to mention a fair portion of the lower parts of her bottom not covered by the skimpy underwear, the ensuing silence prompted Mr Withers into action.

“Are you ready, Charlotte?” The headmaster laid the cane gently across the head girl’s bottom to warn her the first stroke was imminent.

“Yes, sir.” The reply was very soft, quite miserable and totally resigned.

Quickly, Mr Withers swept the cane back and swished it rapidly down to crack sharply across Charlotte’s poorly protected bottom. A quick jerk and a grunt signified its effectiveness, and a red tramline appearing across the bare parts of the girl’s backside indicated precisely where the cane had landed.

The second stroke followed with little delay, aimed slightly lower and causing Charlotte to flinch and grunt again. The third went even lower and made Charlotte ouch her acknowledgement the stroke had been efficiently applied.

Now Mr Withers redirected his aim to the higher parts of the girl’s bottom and two more strokes followed at a fairly rapid pace. Increasingly perceptible snatches and grunts suggested the punishment was becoming increasingly painful.

For the sixth stroke, the headmaster reverted his attention to the centre portions of Charlotte’s bottom and the slightly harder stroke caused her to ouch a second time. The seventh stroke fell to the lower, more naked portions of her backside and brought forth an even louder ouch.

For the eighth and final stroke, Mr Withers applied an especially hard stroke right in the centre of Charlotte’s poor bottom and, together with a distinct arching of her back, she exclaimed: “Oh my God! That really hurt!”

“I think that was your headmaster’s intention, my dear.” Mrs Tomkinson responded approvingly as she moved forward and quickly placed a hand on Charlotte’s back, preventing her from getting up off the desk. “One moment, please Charlotte. I think I shall honour your pledge to Mr Withers after all.”

“I’m sorry?” Charlotte struggled to hold back the tears as she lay there, pinned to the desk.

“I said, I shall not only pay for the cost of repairs to the painting but pay Mr Withers the two thousand five hundred pounds you suggested.”

“Oh, that’s good.” Charlotte had more important things on her mind at that moment, like being able to get up and rub her very sore bottom and pull her trousers up.



“Mummy, what are you doing?

“Mummy, I’ve just been caned! This is hardly the time to give me a spanking as well!”

“No. Perhaps you’re right, Charlotte. I think I’ll leave it until the weekend. Then your bottom will be fit enough for me to give you a really good hiding. That will be something for both of us to look forward to, won’t it?”

The End