Having to witness a boy being caned, the secretary is reminded of her own schooldays.

By Pat Greenham

The first part of this story is based on an incident that took place in the early seventies. The second part is entirely based on my imagination.

There were several mandatory crimes that led automatically to being caned by the Headmaster at my school. These included bullying, truancy, stealing and usually smoking. Additionally, if you were sent-off in a competitive game of rugby the result was always an instruction from the Rugby Master to go directly to the changing room, remove your boots and report to the Headmaster.

Brian Gibbons was in the upper sixth and playing back row. He always had a tendency to be a bit of a dirty player, and on this particular occasion he was being well and truly wound up by the opposition hooker. After the third or fourth remark, Gibbons lost his temper and hit the smaller boy that was playing hooker for the other school and knocked him to the ground. The referee saw the incident and immediately dismissed Gibbons from the field.

As expected, the Rugby Master told him that he knew what to do and five minutes later he was knocking on the door to the Headmaster’s secretary’s outer office. The secretary was actually with the Headmaster taking dictation, came to open the door and showed Gibbons directly in the Head’s Study.

Having already been briefed by the Rugby Master by phone from the pavilion, the Head was fully in the picture. He told Gibbons that he had let the school down, let himself down and that the consequences were that he could expect an immediate caning. The Head told Gibbons to face the window and bend over and touch his toes, and added that as this was the third time he had been caned since being in the sixth form, almost a record in itself, he should drop his rugby shorts. Gibbons said that he only had a jock strap on underneath his shorts.

“Just do as I instructed,” said the Headmaster. “Unless you want to come back tomorrow for a second dose.”

Moments later, Gibbons had indeed dropped his shorts and was told to bend over and touch his toes with his feet twelve inches apart. What made all this worse was that Julie Field, the Headmaster’s secretary, was still in the room and had been told to stay where she was so that she could witness exactly what happens to boys that commit violence on the rugby field.

The Headmaster went to his cupboard and selected a 36 inch sixth form cane, walked to Gibbons left hand side and after lining up the rod gave him an almighty stroke across the centre of his effectively bare bottom. Julie Field looked on with fascination and actually felt that Gibbons had a very cute bottom. Over the next minute, he received five more severe and painful strokes that resulted in six distinct cane weals across his bottom.

Having been caned before, but not previously on effectively his bare bottom, Gibbons knew what to expect but this had been harder and embarrassingly was in front of the Headmaster’s secretary who, apart from anything else, was a very attractive lady in her late twenties.

In the showers a little later, the rest of the team admired his stripes and could not believe he had been caned in front of the highly fanciable Julie Field.

(Now to my imagination)

Julie Field had found the whole incident very enlightening. She had for a few years sat outside the Headmaster’s office as he dealt with boys who had earned a caning, listening to the unmistakable sound of the cane striking a bottom. As part of her job she kept the punishment book and was always briefed in advance of what to enter; the boys name, his crime, the number of strokes and in the last column a T standing for trousers retained, P standing for pants only and B for the very rare times a boy was to be thrashed on his bare bottom. She had often wished she could have watched, but now she had done just that and had watched a severe six stroke caning effectively to the boy’s bare bottom.

It had brought back memories of her time at school when she had been whacked three times by the Headmistress with the slipper, which was actually a gym shoe. The first time had been six whacks across the seat of her skirt when she was about fifteen and had been surprised how painful the experience had been. The second time was a year later when she was again whacked with the gym shoe for disrespectful behaviour to a teacher, but this time she was instructed by the Headmistress to: “Step out of your skirt,” before bending over the desk for another six painful whacks. The third time was when she was in the lower sixth, and she had been told she was extremely close to being caned, with the Headmistress adding that she only resorted to using the cane in the most extreme circumstances. Having been told to once again: “Step out of your skirt,” Julie had once again been told to bend over the desk before the Headmistress had suddenly tugged her knickers down below her knees leaving her bottom completely bare. The six whacks that followed were very painful, but despite everything she remembered being slightly disappointed not to have experienced the cane, having heard about it from the few other girls that had experienced six-of-the-best from the Headmistress.

She was actually feeling slightly turned on just thinking about it when the Headmaster returned to the room to resume their work together. Before they started, he asked her if she had found witnessing the caning interesting. Julie could not help herself but to tell the Headmaster that it had reminded her of her own experiences and during the next few minutes she described the three times she had been whacked at school and that she had very nearly experienced the cane herself.

The Headmaster had always had a slightly flirtatious relationship with Julie who had worked for him for nearly five years and in truth he was finding the idea of his attractive secretary bending over and getting whacked with a gym shoe by her Headmistress quite an interesting idea. The conversation had moved well away from the tedious dictation and he was interested in her story but was unprepared for when Julie added that in many ways she had often wondered on the third occasion, when she had been told that she was a whisker away from getting the cane, what it would actually have been like and how much worse it would have been compared to the plimsoll. The Headmaster without giving his reply much thought said that if she ever wanted to satisfy her curiosity, she only had to ask.

Julie knew immediately that she did want exactly that, but suddenly felt a bit awkward asking him what he meant, stalling for time. He knew he had suggested something he should not have, and replied that if she wanted a couple of strokes across the seat of her skirt, he’d be happy to oblige. The conversation had gone too far and she knew that if she didn’t take this opportunity it would probably be gone forever. How could she possibly start another conversation on another day to get to this point?

She decided that it was now or never and told him she would love him to give her a couple of strokes as he had suggested. The Head had thrashed countless boys over the years and he simply regarded it as part of his job, and he had to admit the idea of giving Julie a couple of strokes was appealing. First, though, he asked if she was serious and if she really wanted to go through with it.

She replied: “It is probably now or never!”

Julie was wearing a tight black pencil skirt and blouse, and he told her to go to the same spot that Gibbons had bent over twenty minutes earlier and take up the same position. As she stood up she thought she had gone mad as she took the few steps to the middle of his study and, with her legs slightly apart, bent over and easily touched her toes, feeling her skirt tighten across her bottom.

The view presented to the Headmaster of her slim but womanly bottom was a delightful target. He picked up the cane he had used earlier and decided to give her nothing more than a medium weight stroke, firm enough to be felt but not too hard.

Meanwhile, the anticipation in Julie’s mind was building as he took the cane slowly back and whacked his secretary right across the middle of her bottom. Julie made not a sound as he left her in position for a while before asking her if the first stroke had been alright, to which she replied that she could take a slightly harder second whack. Thirty seconds later he again took the cane back and gave her a real stinger that at least got an ‘arrrrr’.

It had been twelve years since she had received her third and final beating at school, and she had wondered for all that time what it would have been like to be caned, and now she knew. The fact was she had enjoyed it!

The Head asked her if her curiosity had been satisfied, to which she said: “Indeed it had.”

But Julie wasn’t finished there as she asked how much more painful the cane would be with only one layer of clothing. She knew, and he knew, what she was asking. Julie was in a zone and was putting the Head in a slightly difficult position. He knew that he’d like to give her another two strokes, especially if she was going to take a layer of clothing off, but was it right?

No, was the answer, but then he thought: ‘We are both adults and she is simply asking for a bit of fun.’

He told her that if she wanted, and really wanted it, he would show her what another two strokes was like with just a single layer of clothing, but first he’d like her to write her request in a brief note that he could keep in case anything happened in the future that may compromise him. At the same time, he suggested that she lock the door to the corridor.

Julie went to her outer office, locked the door and sat down on her freshly caned bottom and jotted a note.

‘This note is to confirm that I have requested punishment with the cane from the Headmaster of my own free will and to satisfy my curiosity, and thank him for agreeing to my request.’

Returning to his study she handed him the note and asked if it was sufficient, to which he nodded. She then asked if she should remove her skirt, which was in any case too tight to have been pulled up.

“Go ahead,” he answered.

Undoing the side zip, Julie pushed the skirt down her legs before stepping out of it and giving the Head his first view of her long legs. Without asking, she then pushed her tights down and, one leg at a time, stepped out them. Julie was wearing a fairly skimpy pair of knickers that were partly see-through and she asked if she should bend over in the same spot.

“Go ahead,” the Headmaster repeated.

As Julie planted her legs twelve inches apart and reached down to effortlessly touch her toes, she gave the Head an ever better view now with just her knickers tightened across her superb bottom.

The Head again picked up the cane and approached Julie. He could clearly make out the two earlier cane stripes visible through her semi-see through knickers. Bend over with her skirt on had been a great sight. Now, with just skimpy knickers, Julie’s bottom was an extremely great sight.

He decided to give her a whack similar to the harder second stroke and, making her wait for a few moments, he took the cane slowly back before bringing it back down and hitting her bottom a little lower. He was rewarded with another ‘arrrrr’.

It was clear that Julie was not overly troubled by the cane and he decided to see what she thought of a full force stroke similar to what he would deliver as a punishment to one of the sixth formers. Leaving a full 60 seconds, he touched her bottom to indicate the fourth was about to come before giving her a hard whack which elicited a much louder ‘arrrrrrrrr’.

Standing up, she said with a wicked smile: “That last stroke certainly told me!”

The Head replied: “You are certainly different, and it almost seemed as if you are enjoying the cane.”

“I have been curious for many years,” she answered. “But now I know and whilst I can’t claim to have enjoyed the actual cane strokes, there is a certain warmth in my bottom that is not unpleasant.”

Julie was standing in front of the Headmaster with nothing on below her waist but a pair of skimpy knickers as he told her she had better make herself decent.

Julie then had a further shock for him as she said: “Don’t you think we should complete the set?”

He looked at her and asked what she meant.

“My third whacking at school was with my knickers down, and as I now know how much worse the cane is without my skirt, I am curious to know what it feels like on my bare bottom. Would you mind giving me a final two strokes without my knickers to complete the set?”

The Head was astonished, but they had gone this far and he had her request in writing, so he said: “Julie, you are an extraordinary girl, but if that is what you want that is what you will get. You’d better lower you pants and get back into position.”

Without any embarrassment, Julie pushed her knickers down and stepped out of them giving the Headmaster the view of her frontal nudity with her sporty legs flaring up to her hips and her neatly trimmed pubic triangle at the apex of her legs. She turned and again planted her legs twelve inches apart and reached down to touch her toes, giving the Head an amazing view.

He picked up the cane and moved to Julie’s left. Administering the cane to deserving pupils was part of his job, and although knowing that he always delivered solid canings, he got no gratification from giving punishment. Caning his very attractive secretary at her request was very different, and he was enjoying himself and had to admit that Julie had a wonderful bottom. She had taken the last hard stroke without any protest, so he decided without asking to simply give her two further strokes of the same severity. Her bottom already had four cane weals and there were two perfect gaps.

He left her in position for a full 60 seconds before taking the cane back over his shoulder and bringing it down to strike Julie’s bottom in the centre of one of the gaps with considerable severity. She made another long ‘arrrrrr’ as the considerable pain from the stroke was absorbed.

The Head stepped back to admire his handiwork, leaving at least another minute before he touched her bottom in the one remaining gap and thrashed her one last time. Julie stayed in position as she thought about the gradual increase in the pain levels as she had removed layers of clothing. She also hoped that the Head had liked her bottom, which indeed he had.

The Head asked her to stand and as she faced him she had a glint in her eyes.

“You might think me strange,” She said. “But I enjoyed that experience very much.”

“Did you not find the cane painful?” He asked.

“Yes, each stroke was certainly painful, but not beyond what I could cope with. I’ve had twelve years of wondering what the cane felt like and that curiosity has now been satisfied.”

After a few moments, she added: “I liked the longish gaps between strokes which really built up the anticipation, and there is something very naughty about bending over to be caned especially for the final two strokes across my bare bottom.”

Whilst the Head was enjoying his secretary being naked below the waist, he suggested that she replace her clothes. They never did get back to dictation that day and Julie actually went home early.

In the privacy of her bedroom, she enjoyed looking at the stripes, which lasted for almost a week, across her bottom in the mirror.

The next day the Headmaster asked how her bottom was and, with a glint in her eyes, she told him she had six wonderful stripes and asked him if he wanted to see the damage. Moments later the trousers she was wearing that day together with her knickers were pushed down to her knees as she turned away and bent forward to show-off an impressive set of stripes.

The relationship between them changed and, whilst it was still professional, they became closer to each other. Julie wondered if she would ever experience the cane again, but knew for the time being her curiosity had been well and truly satisfied.

The End

© Pat Greenham 2015