A headmaster struggles to change a girl’s behaviour. Then her mother has an idea.

(Part 6 of the series)


It was approaching the end of the Michaelmas Term and, apart from the unexpected problem back in September when three girls had been caught drinking under-age and the Police had been involved, James Simmons felt things had gone smoothly. The New Head Girl, Stephanie French, had proved a worthy successor to Helen Brown. The traditions of Archdean Lodge had been upheld with all misdemeanours being dealt with by Corporal Punishment. The school had a policy of no detentions, no suspensions and no expulsions. The vast majority of punishments had been kept within the prefecture and from his records he could see that Stephanie French had slippered ten girls, all of which were fifth form or below, and that she had caned eight girls.

Apart from that early problem of the three girls, made so much worse because a young teacher was also involved, only four girls had so far been sent by the Head Girl to the Headmaster for the ultimate punishment of six strokes of the cane on the bare bottom, all of which were sixth formers.

But he knew that at lunchtime that day his services were again going to be needed as Stephanie French had already informed him she was bringing Annabel Hunt along for punishment. Simmons had already given Annabel the cane almost ten moths ago and he remembered that she took her thrashing without a sound and stayed completely still throughout which was very unusual, and which had made him slightly suspicious as to her motives.

At 12.15 on the dot Stephanie and another Senior Prefect arrived with Annabel and they were showed into the Headmaster’s study. Closing the door behind her, Stephanie addressed James Simmons, telling him that the Prefecture had become exasperated with Annabel whose insolence had just got worse and worse. She noted that Annabel had been caned a while ago in this very study and been given the slipper twice since. In her opinion the only course of action was that she once again be given the ultimate punishment of a Headmaster’s caning.

Simmons asked Annabel if she had anything to say, to which she simply said: “No, nothing to add.”

The Headmaster rose from his chair and went to his cupboard to extract his dragon cane, hoping that by selecting the most severe weapon available that he might just teach this girl a lesson once and for all.

Turning back with the cane in his hands, he instructed Annabel to remove her blazer and everything below the waist. It was a look of complete defiance from Annabel’s face as she did as instructed, removing her blazer before kicking her shoes off and unzipping her skirt. As she stepped out of her skirt there was a surprise for both the Head and Stephanie as it became apparent that Annabel was not wearing any knickers. The obvious question followed from Stephanie.

“Why, Annabel, are you not wearing underwear?”

To which the reply came with the same attitude that was synonymous with this girl. “There is no point as I know that in here the cane is given on the bare bottom.”

Stephanie responded: “That is not the point. You are required to wear regulation pants at all times. If you had chosen to wear non-regulation knickers you would be awarded two extra strokes.”

Turning to the Headmaster, Stephanie told him that she felt this blatant breaking of the rules deserved extra strokes, two at the very least.

James Simmons turned to Annabel, who was standing naked from the waist down with her shapely legs flaring up to her hips and dark whispy triangle at the apex, and said: “Eight strokes it is. Please get into position over the stool.”

As Annabel stepped toward the stool she was expressionless as she bent right over, reaching down the far side to hold onto the base of each stool leg and at the same time stretching her own legs out straight behind her.

With the Head Girl and the other prefect standing behind and to the right, Simmons took his position to Annabel’s left and took in the view. However irritating her behaviour was, he had to admit she had a superb bottom, not too slim but certainly not large in any way.

Lining up the Dragon Cane, and remembering that last time she did not make a sound, he had decided that on this occasion he was going to deliver a harder caning than normal. As he took the cane back for the first time he brought it down with speed to strike Annabel right across the centre of her bottom. For the first time he actually extracted a gasp from the girl. Whether it was because she had not been caned for a year, or he was using the Dragon cane, or whether he had simply thrashed her bottom harder, was difficult to say.

Thirty seconds later Simmons gave her a second mighty stroke, slightly below the centre of her bottom, but this time without any response. The third stroke was delivered lower down, above the crease, and formed another red stripe. Annabel’s only response was to slightly widen her legs. For Stephanie and the other prefect, they were witnessing a caning of considerable ferocity and certainly more severe than either had seen before.

The Headmaster decided to put the next two strokes higher up, which came thirty seconds apart, but neither got a response of any kind. Nobody in the room had ever seen a caning given with so little reaction.

The reason was that, unbeknown to them, Annabel was in a world of her own, exploring that combination of extreme pain and extreme pleasure. She was finding the caning incredibly painful and had been shocked by the first stroke. But it was the feeling after each stroke as the pain exploded deep into her bottom that was delivering so much pleasure together with the anticipation of the next agonising blow to come.

Now with five clear red stripes there was one clear space above the centre of her bottom into which the Head delivered the sixth stroke, another fearsome blow which again did not get any sort of response. Throughout, Annabel had stayed completely still apart from parting her legs a little further.

There was a gap between the second and third strokes that could fit the last two whacks. Simmons remarked: “Now for the extra two strokes which you would not be getting had you turned up wearing regulation knickers.”

Annabel did not respond, simply saying to herself: ‘Make them as hard as you want because you will not break me.’

Normally Simmons would leave a longer gap between the penultimate and final strokes, but today decided on a different tactic. The seventh stroke was as hard as any and into the gap, but just as Annabel was getting used to the incredible pain he struck again with the final stroke less than five seconds later which had the effect of surprising the girl who actually gave an involuntary gasp. So he had succeeded in getting her to gasp twice, one after the first stroke and again after the quick succession final two strokes.

She was told to remain in place as he replaced the dragon cane back in the cupboard. Annabel had the most fantastic eight stripes across her delectable bottom in perfect symmetry. Returning to his chair, the Headmaster instructed Annabel to stand and face him, and again it was that look of defiance as she stood with her hands by her side and legs slightly apart with her frontal nudity and her perfectly trimmed pubic triangle on full view. He knew that her bottom must be red hot, but Annabel certainly was not going to show it.

After lecturing Annabel for a couple of minutes he told her to get dressed and, as she left, Simmons asked Stephanie to stay for a few moments. Once they were alone the Headmaster asked his Head Girl for her thoughts, adding that it was very difficult to get a reaction from Annabel Hunt and it was almost as if she wanted to suffer a really severe caning.

Stephanie told him she agreed and perhaps, whatever they gave her as punishment, it was not going to change her. Simmons almost asked if Stephanie thought there was any possibility that Annabel actually enjoyed being thrashed, but decided not to, although not for the first time he had his suspicions.

Nothing more happened that day, and it was the following morning that the Head’s secretary knocked on his door to say Penny Hunt, Annabel’s mother, was on the phone and wanted a word. It had happened once before that a parent had complained about their daughter being caned and James Simmons feared the worst.

Picking up the phone, he asked Penny Hunt how he could help her and was immediately reassured by her tone. Penny told him that she knew her daughter had been caned and wanted to apologise for her dreadful behaviour. She went onto to say that in her opinion it was a punishment that was long overdue and she wanted to express her support.

Penny Hunt then asked if it was possible for her to have an appointment to meet the Headmaster, perhaps after school one day soon. This was a request that he could not turn down and he said she could come later on that day if she wished.

At 5pm, the Head’s secretary once again knocked on his door to say that Penny Hunt was here and asked if she should make some tea before she left for the day.

James Simmons was very struck by Penny Hunt, a lady probably in her late thirties with a very similar but slightly more womanly figure compared to her daughter. She was wearing a striking dress above the knee that showed her figure off very well. They made small talk for a few minutes until after the secretary had delivered the tea and the Headmaster told her that he had nothing more for her to do and she could go home, leaving the two of them alone.

Penny Hunt came straight to the point telling the Head that she wanted to discuss three points. First, she told him she was having a difficult time at home with Annabel and was not at all surprised to hear she was in trouble at school. As such, she was pleased she had been caned and told him that she was extremely impressed with the symmetrical cane stripes on her daughter’s bottom which she had insisted in seeing for herself. What Annabel had not told her mother was the reason why she had eight stripes instead of the usual six, to which James Simmons explained it was policy to award two extra strokes for non-regulation underwear, but that her daughter had chosen not to wear any underwear of any description, which was the reason for the two extra strokes.

Annabel’s mother laughed in a slightly nervous way, and said: “Unfortunately I can see my own daughter in me.” She went onto explain that when she had been at school she had behaved in a not dissimilar way and had also been punished twice, once by the evil Deputy Headmistress and once by her Headmaster. She went on to to tell Simmons that seeing her daughter’s bottom the previous evening had brought back some memories of the two times she had been caned.

The second point Penny Hunt raised was to do with Annabel feeling not included in anything and added she felt many of her problems stemmed from being a loner. She added: “I often see myself in my daughter and it is not helped by her father taking little interest in his daughter since he left home some years ago.”

She went on to say she was thinking of a carrot and stick approach and she would be grateful if he, as her Headmaster, could assist.

“My thinking is that if she starts to behave at home I will reward her, possibly by getting her a car. But I need to see an improvement here at school as well. In this vein, I wonder if there is anything you can do to make her feel more included, such as possibly asking her to be on the Social Committee.”

James Simmons looked thoughtful and said he would give it some thought.

Penny thanked him and added: “Of course if we see no improvement, there will no car and I’d be very grateful if, once you have explained things to Annabel, if she continues to be insolent here you should not hesitate to cane her again as many times as necessary.”

Penny Hunt then said: “That brings me to my third point. I actually blame myself for much of this and I have given myself a long hard look in the mirror. I spend far too many nights out with friends, with Annabel often at home alone. I feel that I am being a poor mother and, as such, would it be possible for you to give me a short sharp shock? I think that I would benefit from punishment much as my daughter received yesterday and I hope you will be able to do the honours.”

The Headmaster looked at her and asked if she was seriously asking him to cane her, to which she replied that that was exactly what she was asking. She added that nobody would need to know and it would be a secret between them. Reaching for her handbag, she pulled out a short letter addressed to the Head setting out her extraordinary request.

Penny went on to tell him the two times she had been caned at school nearly twenty years ago had been quite different. The first caning was given by the Deputy Headmistress who she hated and after being made to raise her skirt and touch her toes, the six rapid strokes that followed across her knickers simply made her more defiant. However, the second caning was given by the Headmaster, again across her knickers, but with her skirt removed. After being instructed to bend across his desk she was given six strokes in a slower and more controlled way. This was the punishment that had pulled her up short. She added that she was fond of the Head and actually felt ashamed to merit a caning from him. As such, the punishment had been effective and did have the effect of changing her attitude for the better. It was this that was behind her thinking and her request to put herself forward for punishment, as she was very much of the mind that she needed something, repeating herself, to be a short sharp shock.

James Simmons could not quite believe what he was being asked to do but at the same time how could he deny the wishes of this very attractive woman. Her also wondered if there was another agenda, and remembered thinking the previous day whether or not her daughter got any form of pleasure from being caned.

He decided to tell Penny Hunt that he would do as she requested, and asked if she wanted to take her ‘punishment’ right away. The answer was yes. He then asked her if she had any specific requests. She said she wanted to take the same caning that her daughter had been given the previous day, which she understood to have been eight strokes bent over a stool.

James Simmons stood up and asked if she was aware that all canings given in this study were with all clothes removed below the waist, and that she should prepare herself.

Unlike schoolgirls who would have to remove their skirt, Penny was wearing a tight fitting dress and she asked if should take it right off. Simmons nodded.

Penny Hunt unzipped her dress and stepped out of it to reveal her underwear. To the Head’s surprise, she was wearing stockings and suspenders together with a very skimpy but expensive looking bra and pants set. With a naughty grin she peeled her tiny knickers down and asked if he wanted her stockings removed, as he’d said everything below the waist.

He said: “No, that will not be necessary.”

In front of James Simmonds was a stunningly attractive woman in her mid thirties, now just in her bra, suspender belt and stockings. She had a lovely figure with nice firm looking breasts, a trim waist and womanly hips with a trimmed auburn triangle at the centre.

He told her Annabel had received the dragon cane, which is reserved for any sixth formers being caned for the second time, adding that the slightly stiffer dragon cane creates the best stripes and would be the most appropriate for a short sharp shock.

Penny was then told to bend over the stool. As she got into position she gave Simmons the view of her superb bare bottom framed by the tops of her stockings and the suspender belt, with her legs stretched out behind her. Just as round as Annabel’s bottom, Penny’s was more womanly. He told her he would give her a stroke every forty-five seconds and added that as she had requested this caning she could tell him if the caning was too much at any time.

Penny simply said: “No, I want to receive a severe caning and not be given the possibility of moderation. To me, this is a punishment I very much deserve.”

As she lay over the stool, she was excited about her bottom being so exposed and the anticipation as she waited for the caning to start was immense.

Without more ado, James Simmons lined up the dragon cane and gave her an almighty whack right across the centre of her bottom, which immediately created a red stripe and a gasp from Penny. It had been twenty years since she had felt the cane, and had never before been caned on the bare bottom. It had been a genuine shock.

The second stroke was delivered just below the first and caused another gasp, but at least Penny knew what to expect. Now with two stripes quite close together, Simmons decided to deliver three strokes lower, and three higher. The next stroke was low down above the crease but perfectly parallel, and got another gasp from Penny. This caning was a lot more severe than she remembered from her schooldays.

The fourth stroke hit Penny’s bottom toward the top and created another perfect cane weal. Half way through now, he gave her a longer gap of well over a minute before he thrashed her for the fifth time in the gap above the crease. It caused another gasp from Penny.

It was interesting that the mother was displaying considerably more pain than her daughter. The pattern across her bottom was just as James would have liked, with a larger gap for the next two strokes above the centre, and one remaining gap below for the final stroke.

The sixth and seventh strokes were ones that Penny seemed to take better, almost without a sound, but he waited a full minute before delivering the hardest of all in the one remaining gap below the centre of her now striped bottom.

He told her to stand as he sat down behind his desk and asked her if she felt she had been suitably punished.

She replied: “Yes, I certainly have. I actually found it a lot more painful than I expected, but I told you that I wanted a severe caning which is certainly what you have given me.”

As she stood in front of his desk, her hands were rubbing her bottom with her frontal nudity completely exposed, apart from a semi see-through bra. She said she would look forward to seeing the stripes.

As much as the Headmaster was enjoying Penny Hunt being almost naked, he told her that perhaps she should get dressed, and asked if she would like a drink. Five minutes later Penny was sitting in the Head’s study with a glass of wine, fully dressed in her tight dress that fitted her very well. It was almost as if nothing had happened, apart from the fire that now existed in her bottom.

Before she left, she thanked him and asked: “If I ever again feel bad about my behaviour, would you consider a repeat?”

The answer was: “Of course.”

The Headmaster did find ways of getting Annabel more involved in the running of the school and the second caning from the Headmaster had made her more respectful. Her behaviour at home also improved. James Simmons wondered if Penny would one day return.

Penny’s Postscript:

I have to admit that being caned again after almost twenty years was a very much more painful experience than I remembered. But I am pleased I asked to be punished because I have suddenly realised how bad a mother I have become and, as strange as it might sound, I felt that I really did need a short, sharp shock to pull me up short, very much as my old Headmaster did when I myself was a sixth former.

James Simmons is authoritative and demands respect. As such, he was perfect to deliver my caning. Hopefully I will remember the experience of being thrashed severely with the cane every time I am tempted to leave my daughter home alone. At the same time as I look back and think about being caned, there was another agenda which was sparked when I saw the eight perfect stripes across Annabel’s bottom.

The truth is that I felt I deserved to have those stripes as well, and I have to admit that I did choose my sexiest dress together with a skimpy underwear set. I also gave my pubic triangle a quick trim before going to meet the Headmaster, hoping that I could persuade him to cane my bottom.

When he said he would comply with my request, there was wave of electricity that went through my body. As I undressed in front of him, I hoped he liked what he saw, especially when I slid my knickers down before stepping out of them. Strangely, I felt empowered and as I bent across the stool with my bare bottom so horribly exposed. I cannot deny I felt aroused and full of anticipation of what was about to happen, and I certainly cannot complain about not being properly thrashed!

James’s Postscript:

That was an extraordinary meeting with Penny Hunt. Caning Annabel Hunt the previous day had been a necessary and deserved punishment, and I hope that she learns to be more respectful. I will certainly take Penny Hunt’s comments into account and try and make Annabel feel more included within the school. Time will tell if Penny Hunt will change into a better mother.

Her request to be punished herself was truly extraordinary, but she was determined and I felt that I could not turn her request down. Penny Hunt is a very attractive women and she showed no sign of any embarrassment as she undressed. I was surprised, and slightly taken aback, that she was wearing stockings and what could only be described as very sexy underwear. After she stepped out of her knickers, the sight as she bent right over the stool with her bare bottom on full show was quite something. She told me she wanted a hard caning, and I hope that I succeeded.

The End

© PG 2017