Robyn’s Entry – this is an entry for one of my writing competition.

You will know Robyn if you follow my blog, she is my editor. What she does to my stories is quite remarkable.

To see the rest of the entries to this, my first competition, click here…

Robyn’s Entry…


The Head Girl, Samantha, sat in the corner gazing intently at Charlotte bent over Mr Jones’s punishment stool. Finally she had managed to bring about Charlotte’s comeuppance. She had caught Charlotte bullying one of the younger girls in the dormitory just before lights out. Up until now Charlotte had been very clever and had managed to avoid detection for numerous ‘crimes’. However, Samantha had finally caught her in the act and had ‘nailed’ her. She had reported the incident to the headmaster, Mr Jones, and was instructed to bring Charlotte to his study after morning assembly the following day. He took instances of bullying very seriously.

On arrival, Mr Jones had asked Samantha to stay to act as a witness to Charlotte’s forthcoming punishment. Predictably Charlotte had tried to lie her way out of the punishment, but Mr Jones was having none of it. He trusted his head girl’s account of the affair and that was the end of it. She was firmly told that she had better own up, otherwise 12 strokes of his senior cane would be raised to 18 strokes. Charlotte rapidly capitulated, not wishing to run the risk of incurring extra strokes on top of what was already a severe punishment.

Mr Jones ordered her to bend over the punishment stool and requested Samantha to ‘prepare’ the ‘wretched girl’ for her caning. Samantha gladly complied, proceeding to slowly roll up Charlotte’s grey pleated school skirt over her back. As she did so, she whispered, “I’m going to enjoy watching your caning. I hope it hurts like hell. You deserve it.”

Charlotte muttered back under her breath, “You bitch!”

Ignoring the comment, Samantha asked Mr Jones loudly, “Shall I pull her knickers down, Mr Jones? I assume that you want to cane her on the bare?” She knew full well what the answer would be, as Mr Jones always caned pupils on the bare. However, it was her way of getting back at Charlotte.

‘“Yes please, Samantha. Thank you.

Samantha inserted her fingers in the waistband of Charlotte’s knickers and slowly drew them down over her pale unblemished white bottom, whispering again in Charlotte’s ear as she did so, “Your bottom is really going to smart when he gets going. Enjoy!”

This time Charlotte was too nervous to respond to Samantha’s taunt. She felt very vulnerable bent over the punishment stool with her now bared bottom presented beautifully. Her long slender legs stretched out behind her, with her white school knickers hanging limply around her ankles. ‘Oh, why had she been caught by that nasty bitch? This is going to hurt dreadfully. Twelve bloody strokes! I’ve never had more than four before,’ she thought.

“Thank you, Samantha. Now will you sit over there out of the way in the corner whilst I cane this young lady. I don’t want to hit you by mistake,” said Mr Jones.

Samantha reluctantly moved into the corner and sat down facing Charlotte’s head. She had hoped to be able to watch Charlotte’s caning from the other end. She would have loved to watch Charlotte’s naked buttocks being thrashed. It would be a real turn on to see her bottom squirming and writhing across the punishment stool, red wheals steadily blossoming across her cheeks as successive cane strokes landed across her quivering flesh.

Unfortunately that was not to be. Oh well, she would have to be content with watching Charlotte’s facial reactions and enjoy listening to the thrilling noise of the cane swishing down across the bitch’s rump and the resultant howls of pain. It was so annoying! Why couldn’t she stand at the other end of the room?

And then, Samantha saw something that she had never noticed before…a large free-standing mirror stood facing her at the other end of the room. ‘Gosh, this was a stroke of luck,’ she thought, as she realised that she could see Charlotte’s bottom clearly reflected in all its glorious pert rotundity! She would be able to witness Charlotte’s punishment after all from both ‘ends’!

Samantha was suddenly brought back from her reveries by the sound of Mr Jones swishing his cane through the air to loosen up his swing. She edged forward in her seat to ensure that she had a better view of Charlotte’s bottom in the mirror.

“Are you ready, Charlotte?” asked Mr Jones, tapping the cane across her bottom, making her cheeks visibly wobble.

“Yes, Sir…as ready as I ever will be!” replied Charlotte in a quavering voice.

Samantha held her breath as she watched the cane raised slowly over Mr Jones’s shoulder. It seemed to hover for ages before it suddenly came swooshing down and landed with a loud THWACK right across the meatiest portion of Charlotte’s bottom. Charlotte squealed as an horrendous stinging, burning sensation spread rapidly across her naked cheeks. Samantha’s eyes were riveted on the reflection of Charlotte’s buttocks. A white line left by the cane was steadily turning red and the muscles of her bottom cheeks were twitching involuntarily.

Samantha clasped her hands together, pushed them down between her legs, pressing into her crotch and she started to gently rock. As she was doing so, her gaze met Charlotte’s already teary eyes. She realised that Charlotte must know what she was doing, but what the heck. She was so turned on by being able to witness the caning, she had to indulge her urges, just so long as Mr Jones didn’t see what she was doing! Hopefully he was far too engrossed aiming his cane across Charlotte’s naked bottom to notice what she was doing, and Charlotte would soon have other things to focus on as she saw the cane rise again.

Swish, Thwack! The cane came down for a second time, eliciting a louder cry of pain from Charlotte, “Yeowwhhhh!”

Samantha eyes widened as she witnessed this second stroke whip into Charlotte’s rump, creating a second parallel red wheal just below the first. ‘Ummhh, this is so exciting. I can’t wait for the next,’ she thought, rocking away gently in her seat, her hands pressing ever more tightly into her crotch.

Swish, Thwack! “YEOW, FUCK! Oh my god, that hurt! Please, please Mr Jones, no more!” Charlotte yelled out as she started to rise from the punishment stool.

“How dare you swear and try to get up! Get back over the stool this instance, young lady. That’ll be an extra two strokes,” shouted Mr Jones. “Samantha, would you be so kind as to hold Charlotte down. I don’t think she’ll be able to stay in position for the remaining ten strokes without your assistance.”

‘Drat,’ thought Samantha. ‘I won’t be able to ‘indulge’ myself, but still orders are orders!’

Samantha stood up and pushed down on Charlotte’s shoulders, making sure that she was still able to see the reflection of Charlotte’s bottom in the mirror behind Mr Jones. This was a most interesting position to witness a caning, facing the headmaster and seeing the top of Charlotte’s bottom from virtually above, as well as the full view in the mirror beyond.

And so the caning proceeded, every stroke causing Charlotte to writhe around under Samantha’s tight grasp. Samantha drank in the sights and sounds, feeling the shock waves of each stroke spread through Charlotte’s body as she howled her loud protests.

Finally the caning ended, leaving Charlotte sobbing and lying limply loudly across the stool, a ‘heat haze’ shimmering just above her well-striped and reddened buttocks. Samantha loosened her grip on Charlotte’s shoulders and stood up, wishing that she could find some relief for her now very moist, pulsating pussy.

After a few minutes, Mr Jones instructed Charlotte to rise and dress herself. He then dismissed her and they both watched her slowly limp out of his study, gently rubbing her well caned bottom.

“That was very well done, Sir,” said Samantha, her eyes gleaning. “She deserved every single stroke you gave her. It was most exhilarating to watch!”

“Thank you for your assistance, Samantha,” responded Mr Jones.

Samantha hesitated and then blurted out before she fully realised what she was saying, “Please Sir, could you please cane me like you have just caned Charlotte. I need some release!”

Mr Jones looked slightly taken aback, but realised from years of experience that many girls were turned on by the whole idea of corporal punishment, both as witnesses and recipients. He had also observed Samantha’s antics rocking in the chair at the start of Charlotte’s caning.

“Certainly Samantha. If that is what you wish. Kindly raise your skirt, lower your knickers and get your naughty little bottom over that punishment stool NOW! Shall we start with a round dozen?”

“Yes please, Sir. That would be lovely!” replied Samantha eagerly.

“Would you like to watch yourself being caned? I could angle that mirror you have been looking at throughout Charlotte’s caning so that you see yourself.”

“Oh, yes please Sir. That would be most exciting!”

Having moved the mirror into position, Mr Jones picked up his cane and proceeded to give Samantha the thrashing of her life. Although she cried out and wriggled around on the stool, she stayed in place and didn’t beg him to stop. After 12 strokes, he asked if she had had enough, but she pleaded with him to continue.

After a further dozen strokes, he noticed through her open legs that her pussy had become very moist. Dropping the cane, he started to gently caress her well welted buttocks. She murmured pleasurable noises, as he let his hand stray between her legs. She pushed her bottom back at him, clearly willing him to pleasure her. What a wanton hussy his head girl was! Despite his full-on erection, his professional conscience wouldn’t allow him to go as far as he might otherwise have done. Instead, he inserted his finger into her well lubricated cunt and started to stimulate her erect clitoris. Every now and again he slapped her bottom with his other hand, to which she offered no objection, just emitting loud gasps of pleasure until finally she arched her back and let out a loud drawn out scream of orgasmic pleasure. She then slumped totally satiated over the stool, whilst Mr Jones retired exhausted to sit at his desk admiring his handiwork across Samantha’s bottom. Life as a headmaster was so demanding!