A sequel to The New Headmaster, Two sisters caned, The Crisis, and Reflections on Year One for the Headmaster


The new term was barely three weeks old when James Simmons was faced with a significant problem. The Headmaster’s secretary received a call from the local police that three girls had been caught drinking under-age in one of the pubs in the local town. The real problem was that they were with Alison White who was a relatively new teacher and it was her that ordered the bottle of champagne, and it was only when she ordered a second bottle that she was asked for evidence that the three girls were eighteen.

As it then transpired that they were all seventeen and in the lower sixth. The pub refused to supply a second bottle and insisted on knowing the names of the three girls and the school they attended. Subsequently, the landlord of the pub called the police to inform them that his pub had served three under-age girls indirectly with alcohol and gave them the names and the fact that it was a teacher from Ashdean Lodge that had actually purchased the alcohol. The police had thanked him for the information and his honesty and said they would not be taking any action against the pub.

It was this call that led the police to contact the school and subsequently having a conversation with James Simmons. They told the Head that he should know about the incident, both regarding the three girls and that it had been a member of staff that had been responsible. It was agreed the Headmaster would deal with the matter internally and the police told him that on that basis they would be taking no further action.

James Simmons spoke to Stephanie French, his new Head-Girl and it was agreed that the Prefecture should punish each of the three girls. They subsequently received six strokes of the cane across their knickers in front of each other. This was the first time that Stephanie had used the cane as a punishment, apart from her practice session at the end of the previous term when she had caned the previous Head-Girl, Helen Brown.

When they arrived for their punishment, Stephanie decided that all three should remove their blazers and skirts at the same time before each was caned. With Jane Howard, Melissa Hall and Sandra Bennett now standing in a line before Stephanie French and one other Senior Prefect in just their school shirt and knickers, it was apparent that only Melissa was wearing regulation knickers. Jane was called forward first and told to get into position over the stool. She was a tall girl with an ample bottom and Stephanie thought about the instructions she had been given by the Headmaster when she had caned Helen Brown. She also remembered that Helen Brown had told her she had the authority to add two strokes for non-regulation knickers, but actually it was more effective to pull such knickers upward, which effectively bared the middle and lower part of their bottom, which in itself made the punishment worse.

Jane’s knickers were quite skimpy and once pulled up left her very exposed. Lining up the sixth form cane for the first time, Stephanie remembered the instructions; a slow back-swing and aim for the centre of the bottom. It was true to say she had remembered well as she struck Jane’s bottom right in the centre with some force which resulted in an anguished gasp from the girl over the stool.

Stephanie went slowly and Jane had been over the stool for over two minutes before she received the final stroke, leaving six excellent stripes all below the skimpy knickers. Jane was told to stand and move back in line without touching her damaged bottom.

Melissa was next to be told to get into position and, as she bent over the stool, it was clear that her regulation knickers were going to give significantly more protection. The girls could all appreciate that Melissa had a peach of a bottom and, as Stephanie delivered another methodical caning lasting at least two minutes, producing in the process some very loud gasps. The cane had actually left lines across her dark blue knickers and Melissa rose in considerable pain.

It was now Sandra’s turn who looked terrified as she stepped forward and bent over the stool feeling incredibly vulnerable. Like Jane, Sandra was not wearing regulation knickers and, like Jane, suffered the indignity of having her pants pulled up effectively baring her bottom. Hers was the smallest bottom of the three and Stephanie knew she must be accurate to avoid hitting too low or too high.

This was the fourth bottom that Stephanie had ever caned and she successfully got the first stroke into the centre of Sandra’s bottom, which resulted in another loud gasp and a perfect red stripe. With the smallest bottom, it was likely that she would feel the cane more than her two friends. However, Stephanie was not letting up as she struck for the second time, just above the first. She was concentrating on accuracy rather than force, but Sandra was certainly not getting away lightly. Again her caning lasted over two minutes and she had six visible stripes below the line of her knickers by the end.

It is true to say that all three left the Prefect’s Common Room in significant discomfort, each with red hot bottoms and the distinction that they had been the first girls to be caned by the new Head Girl.

This just left the teacher involved and James Simmons was giving great thought to what he should do. He asked his secretary to arrange a meeting at the end of the school day with Alison White.

At just after 4pm, Alison White came into the Head’s study looking very sheepish, knowing that this was going to be an uncomfortable meeting. By any stretch, this was a serious matter and James Simmons asked Alison what did she think the consequences might have been if the police had pressed charges? Saying that she was not really sure, the Headmaster told her she would have lost her job. Actually, the Head liked Alison a great deal and knew she was doing a very good job within the PE team. It was on the way back from a hockey match, when the school team had won a big game, that Alison had suggested celebrating with a bottle of champagne.

However, he felt he could not let this pass and as Alison was only in her second year at the school, and only twenty-four years old, he had decided on a radical course of action.

He told her: “By rights, I should dismiss you for this on a number of grounds, not the least that you purchased alcohol for three underage girls, but as you are still quite young I am prepared to offer you an unconventional alternative.” Pausing for effect, he went on to say: “I cannot let this matter pass without some form of discipline. You have caused the three girls in question to be caned by the Prefecture, so my alternative proposal to dismissing you is that you agree to be caned as well.”

To say Alison looked shocked would be an under statement, but she was horrified that she could lose her job. He added that if she wanted time to think about the two alternatives, she could see him tomorrow morning with her decision. But she knew that in reality she had no choice; she was just starting her second year in teaching, loved the school and the idea of being sacked was absolutely awful.

She looked at James Simmons and said she felt she had no choice and also told him she was very sorry for what had happened.

She asked: “When exactly will I be caned and how will it be carried out?”

This answer confirmed she was accepting the unconventional alternative.

The Headmaster told her she could be punished right away if she wanted to get it out of the way and that she would caned exactly as if she was in the sixth form, without adding that he proposed to use the dragon cane.

Alison was horrified about the prospect of being caned. She had never experienced any sort of corporal punishment before. Regardless, she replied that did not want it hanging over her and said she would like him to carry out the discipline right away. She added that she knew she deserved some kind of punishment and would do anything to avoid being sacked.

Standing up, the Headmaster placed the stool used for caning in the middle of the room and selected the dragon cane from the cupboard. Allison knew he always caned girls across their bare bottoms and was not surprised when he told her to remove everything below the waist. Kicking off her shoes, she undid her super tight black lycra exercise trousers and peeled them down one leg at a time. She was very VPL conscious and as such was actually wearing a thong. As it would give no protection, Alison asked if she could retain it.

The answer was no, an element of humiliation was an essential part of being caned and they were quickly removed. Being a PE teacher, Alison was very fit and the twenty-four old standing in front of James Simmons, naked from the waist down, was a sight indeed with her sporty legs flaring up to her shapely hips and a nicely trimmed triangle of auburn hair. He told her to turn round and get into position across the stool and, as she bent over, she was mortified by the thought of her bare bottom being presented to the Headmaster, a man she looked up to and respected. But, she had got herself into this position and had to take the consequences.

For James Simmons, Alison had a perfect bottom. So many that came before him for the cane, whilst being seventeen or eighteen, had bottoms that were very much those of teenagers. Alison, however, had the bottom of a young woman and was more defined and developed in a very good way. Positioned as she was, right over the stool and reaching down the far side to hold onto the bar low down, with her legs stretched out behind her, it was a sight that would stir any red blooded man. But he had a job to do and Alison very much deserved what was about to happen.

He had not mentioned he was using the dragon cane as opposed to the sixth form cane and lined it up against the target before taking the cane back over his shoulder and whipping it in hard to strike the centre of her bottom, causing a load gasp. Alison was very shocked by the sheer intensity of the pain caused by just one stroke, and wondered how exactly she was going to cope with five more. Simmons left her in position for well over thirty seconds before giving her the second stroke, equally as hard and just below the first already formed red stripe, causing another anguished gasp.

This was a rare treat for the Headmaster. Giving the cane to schoolgirls brought before him by the Head Girl was one thing, but caning probably the most attractive member of his female staff across her bare bottom in these exceptional circumstances with just the two of them in the room was wonderful. And to think that just over one year ago he had never used a cane.

Leaving Alison in position for almost a minute, Simmons thrashed her for the third time, striking just above the first stroke and causing another loud gasp as she absorbed the extreme pain caused by the dragon cane. Alison had now received three hard strokes of the cane as she lay across the stool and didn’t know whether she wanted him to hurry up or let her try and recover from the devastating pain caused by each stroke.

The Headmaster was in no hurry and in the last year he had become a master of the art of giving a very decent caning. He stepped back to take in the exceptional view of her superb bottom, now with three very symmetrical red stripes very much across the centre of Alison’s bottom.

After another thirty seconds, he touched her bottom lower down with the dragon cane and, taking it slowly back, thrashed her again causing another anguished gasp, this time striking above the crease and leaving a purposeful gap between the first three and the fourth, in his own mind reserving that space for the last stroke.

Alison meanwhile had moved her feet apart to give her better balance and in the process giving the Headmaster an even more revealing view. With two strokes left, Simmons again left at least a sixty seconds gap before measuring the dragon cane above the first three cane marks. Again taking the cane slowly back, he thrashed her again, just above the centre of her bottom. As Alison lay across the stool in a dreadfully revealing position, she knew that there was only one more to come and certainly wanted it to happen as quickly as possible.

But Simmons had different ideas. He had given fifteen canings in his first year to girls, mostly in the fifth and sixth forms, but all of them were given as part of his job. He had certainly appreciated some of the girls that had been across his stool had lovely bottoms, but they were still all teenagers. This was different. Alison was an adult with the most incredible bottom and, whilst she deserved the punishment and had avoided dismissal, he had to agree with himself that the situation had presented him with the most wonderful opportunity. But he knew he could not hang it out for ever and lined up the final stroke in the gap below the centre of her bottom. He gave her the final stroke which, in tradition, was the hardest of all and got the loudest gasp. He had succeeded in creating the most perfect set of six stripes across Alison’s bottom, while she just lay across the stool in a state of shock but also relief that it was over and wondering how long it might take for the pain to subside.

James Simmons told her to stand as he went behind his desk and took his seat. Alison stood before him with her hands gently rubbing her damaged bottom with her frontal nudity and auburn triangle on full display. It actually occurred to her that it was a good thing that had recently trimmed it.

She had thought that being caned would be painful, but told him that she also never thought it could possibly be quite so bad. He told her he had used the most severe cane available, which was actually reserved for sixth formers being caned for a second time, which may have contributed. He also told her that at least the matter was closed, the three lower sixth formers had each been caned by the Head Girl and she, Alison, had also been disciplined. He then lied when he told her that he regretted he had disciplined her in this way but it was at least better than being dismissed. The truth was, he had enjoyed himself enormously!

Whilst this conversation was taking place, Alison remained naked from the waist down as he gave her the normal post-caning lecture. Eventually she was allowed to get dressed and she very gingerly replaced her miniscule pants and tight exercise trousers. For the rest of the day and evening, Alison was reminded of the caning every time she sat down.

When she got home the first thing she did was to go upstairs to her bedroom and have a look at her bottom in the mirror. She was impressed, in a horrified way, by the six perfectly symmetrical stripes.

Alison went on to stay at the school for over ten years and continued to have an excellent relationship with James Simmons. But they both knew what had happened that day, a day neither would ever forget.

The End

© PG 2017