Dating a boyfriend gets a girl and her friend into her headmaster’s bad books. An old story re-published.

By Kenny Walters

“Bye Rodney.”

“Bye Honeybunch.”

The moment the door slammed shut, Rodney thrust the little sports car into gear and roared away down the drive. The tall girl with the honey blonde hair waved after him as the red MG disappeared into the darkness through the wrought iron gates, then turned towards the heavy oak door at the front of the large mansion-like building.

“Good evening, er, honeybunch.”

Rachel Withercote jumped.

“Oh, Miss Harpethorne! You startled me.” Rachel ignored the sarcasm.

“Did I, Rachel?” Miss Harpethorne stood barring the way to the front door, her arms folded across her stout figure, clothed as always in a heavy tweed suit. “Did I indeed?”

“Yes, well, I really must get to bed, Miss Harpethorne. School day tomorrow, you know.” Rachel smoothed her hands down the sides of her tight short red dress and tried to step round the formidable teacher.

“Haven’t we forgotten something, Rachel?”

The very attractive eighteen year old’s shoulder-length honey-blonde hair shimmered in the moonlight as she shuddered inwardly at the senior teacher’s tormenting tone.

“No, I don’t think so, Miss Harpethorne.” Rachel replied innocently.

“Shouldn’t you have been on dormitory duty this evening, Rachel?” Miss Harpethorne smiled, enjoying having caught the sixth form prefect out. “You know, making sure all the junior girls are safely accounted for and that none of the sixth from girls arrive back later than ten o’clock?”

“Yes, I do know what’s required of a dormitory duty, Miss Harpethorne.” Rachel answered with less than sensible brusqueness. “I just hadn’t realised it was after ten o’clock.”

“Really? Well, it is actually ten minutes past midnight and you should be performing the task that I am now undertaking on your behalf.”

“Oh. Sorry, Miss Harpethorne.”

“Oh indeed, Rachel. This will have to be reported to Mr Grimes. For now, I suggest you get of to bed at once.”

The following morning, at eleven o’clock, Rachel tapped lightly on the headmaster’s study door.

“You wanted to see me, sir?” Rachel closed the door quietly behind her, turned and took the few short paces across the deep-pile carpet until she stood before Mr Arthur Grimes’ large mahogany desk. Gone was the seductive tiny red dress and the flowing hair of the previous evening, replaced for this meeting by a smart charcoal grey business suit of tight, almost knee length skirt, jacket and freshly ironed white blouse. Even her honey-blonde hair was neatly tied back in a ponytail.

“So I did, Rachel. So I did.”

Arthur Grimes was nearly sixty years old, plump and short, with greasy black hair that everyone was certain was maintained with the help of a bottle from the local chemist. Rachel looked demurely down at the headmaster, hoping for the usual invitation to sit on one of the comfortable chairs placed around the desk.

“Miss Harpethorne tells me you absconded from dormitory duty last night, Rachel. Not only that but you were also back late, well past curfew indeed. Is that true?”

“Well, yes. Sort of, sir.” Rachel fidgeted, feeling particularly awkward and uncomfortable. “It was all a bit of a mix-up, actually sir. I thought it was Helen Hardcastle’s turn to do the dorm patrol and so I went out. Then my watch must have stopped and I was late getting back.”

“You didn’t just forget, then Rachel?” Mr Grimes looked at the eighteen year old prefect, his head tilted. “I do realise how a young lady can forget these things when she has other things on her mind.” He smiled reassuringly.

“Well sir.” Rachel’s mind raced as she calculated whether it might be better to come clean than hold out with her somewhat flimsy excuse. “Actually, yes, that is what happened. I am very sorry, sir.”

“I see.” Mr Grimes rubbed his hands together and Rachel knew he was contemplating her fate. “I think, Rachel, we need a little something to improve the memory, don’t we?”

The eighteen year old’s heart beat a little faster as her headmaster stood up, extending himself to his full five feet five inches, just four inches shorter than Rachel. She watched with increasing panic as he sauntered over to a tall corner cupboard.

“Sir! You’re not….?”

Arthur Grimes turned to face her, a bunch of keys already out of his pocket and being sorted to find the correct one.

“I think it would be appropriate, don’t you Rachel?”

“No, sir.” Rachel heard her voice almost shout with anxiety. “That’s not fair, sir.”

“What would you suggest, then Rachel?” Mr Grimes put both his hands in his pockets.

“Five days extra dorm duty, sir?” Rachel offered. “That would seem quite appropriate in the circumstances.”

The headmaster smiled. Much to Rachel’s relief, he began to walk back to his desk.

“Five days extra dorm duty, plus you will revert to school uniform for those five days. Your choice, Rachel.”

“But sir! I’m a prefect. That would be so humiliating.”

“My little way of demonstrating to the whole school that you are being punished, as well as a warning to the other prefects that their duties and responsibilities are not to be taken lightly. It’s my final offer, Rachel. Unless you prefer…” Arthur Grimes nodded towards the corner cupboard.

“Very well, sir. Five days of extra dorm duty.” Rachel responded before that line could be taken any further. “I’ll accept that as my punishment, sir.”

“And five days back in uniform, Rachel?”

“Yes, sir. If I must!”

That evening, Rachel Withercote sneaked out through the main gates and got into the little red MG that was already waiting for her.

“What’s this?” Rodney’s eyes lit up. “You really know how to turn a chap on!”

Rachel brushed Rodney’s hand away as he tried to push her uniform grey pleated skirt up her shapely thigh.

“No, don’t start the engine, Rodney. I won’t be able to make it this evening.”

“Why not?”

“Because you bloody well got me late back last night. That’s why!”

“Ah, did the naughty schoolgirl get into trouble then?” Rodney teased her.

“Yes I did, actually.” Rachel snapped back. “That’s why I’m wearing this bloody school uniform.”

“Oh dear! Did you get your cute little botty smacked as well, by any chance?”

“Don’t tease me, Rodney. This is bad enough. I’ve got to wear this uniform for five whole days and do dorm patrol every evening as well. So, I’m afraid I won’t be able to see you again until next Tuesday.”

“Oh come on, Rachel! What can they do? Let’s go down the pub and talk about it.”

“No, Rodney. I don’t dare get into trouble again.”

Rachel and Rodney parted company soon after, leaving the eighteen year old prefect to return to her school duties. By the end of the third day, though, Rachel was becoming extremely tired of all the other girls tormenting her about having to wear school uniform of grey skirt or trousers and red blazer, as opposed to the prefects’ usual attire of dark grey or black trousers or skirt and black blazer. When Rodney telephoned her and asked her out again, she relented.

“Sarah.” Rachel grabbed the arm of her friend and fellow prefect, Sarah Armson. “Sarah, do us a favour?”

“What?” Sarah, a short dark-haired girl with a pretty face that was nearly always smiling, allowed her journey along the corridor towards the prefects rest room to be halted.

“Could you by any chance cover for me this evening?”

“You’re not serious?”

“Yes I am.”

“Trying to get me into trouble with old Grimes as well, are you?”

“Of course not. Look, I’ll take the blame if anything goes wrong.”

“I presume this is all to do with that boyfriend of yours, is it?”

“Rodney. Yes.” Rachel frowned. “Look, if I don’t get out and see him this evening he’ll be chatting up some barmaid somewhere and then I’ll lose him. It’s really important, Sarah.”

“Okay then, but just make sure you don’t get caught. That’s all.”

At half past eleven that evening, Rodney Wilkes turned the key and the MG’s engine burst into life.

“Nice night, honeybunch?”

“Don’t call me that. And, yes, it’s been great.”

Rodney selected first gear and the small car shot out of the car park of the ‘Anglers Arms’. Almost immediately there was a squeal of brakes as a large Rover saloon coming along the main road screeched to a halt, narrowly avoiding the little red sports car. The driver laid on the horn to demonstrate to Rodney what he thought of his lack of observation.

“Up yours! Silly old bugger!” Rodney held two fingers up and sped off down the road.

Rachel looked briefly in the direction of the other car, recognising instantly the short plump man sitting in the driver’s seat.

“Oh no, Rodney! That was old Grimes!” Rachel squealed. “My headmaster.”

“Oh, stuff him. He shouldn’t have been speeding along like that.”

“Rodney! I’m really for it now!”

“Why? What’s he going to do? Eh?”

Rachel remained tight-lipped.

“I suppose there’s no chance he could smack your sweet little bottom?” Rodney mused as he drove them back towards Rachel’s school. “I wouldn’t mind watching that.”

“Don’t be so silly!” Rachel answered tetchily.

The following day, Rachel was walking along the corridor when she caught up with her friend, Sarah, heading in the same direction.

“Sarah, I really am so sorry.”

“Huh!” For once, Sarah wasn’t smiling as she stopped and faced Rachel.

“Look, don’t worry, Sarah. I’ll take all the blame.”

“I don’t somehow think that’s going to cut too much ice with old Grimes, do you?”

“I’ll explain.”

“Just make sure you don’t get me into any more trouble than I’m already in, that’s all.”

The two eighteen year old prefects stopped together, outside the door to Mr Grimes’ study. They quickly checked their state of dress, Sarah in tight black leggings and white blouse, Rachel in charcoal grey pinstripe trousers and matching jacket.

“Ready?” Sarah held her knuckle to the door.

Rachel gave a nod and Sarah tapped on the door.


Within moments, the two girls stood shoulder to shoulder in front of the headmaster’s large mahogany desk. Mr Grimes continued reading a long typewritten letter until he had absorbed the entire contents. Only then did he pull his spectacles half way down his nose and peer up at the two smartly dressed prefects.

“I don’t recall giving you permission to take Rachel’s place on dormitory duty last night, Sarah. Perhaps you could remind me when I did that.”

“You didn’t, sir.” Sarah hesitated for a moment, half expecting Rachel to break in with an answer on her behalf.

“And you were aware Rachel was doing extra duties as a part of a punishment, were you?”

“Yes, sir.”

“You’re not leaving me with a great deal of choice then, are you Sarah?”

“No, sir.”

“Please, sir.” Rachel finally spoke up. “Can I just say I take full responsibility for last night.”

“I’ll get to you when I’m good and ready, thank you Rachel.” The headmaster stood up and went over to the tall cupboard in the corner of his study. He continued speaking with his back towards the two girls. “Sarah is, I’m sure, only too aware she had no business doing your dormitory duty, especially when it formed part of your punishment. Is that not correct, Sarah?”

“Yes, sir.”

Sarah glared at Rachel when Mr Grimes turned holding a long slender length of pale yellow rattan, the end curled round into a crook handle.

“Three strokes, Sarah.” The headmaster looked the smaller girl straight in the eye. “Your choice.”

Sarah trembled visibly, stepped away from Rachel’s side and rubbed her hands together as though the room had suddenly become quite cold. She hesitated, and then took a couple of steps towards the large desk. With a quick glance towards the headmaster, she bent herself down across the desk.

“Sir! This isn’t fair, sir.” Rachel’s eyes stared down at the seat of Sarah’s tight black leggings, the garment moulded around the girl’s neat round bottom. “I’ve said I’ll take full responsibility.”

“And I’ve said I’ll get around to you in due course, Rachel.”

“But, it’s my fault Sarah got involved, sir. If I hadn’t begged her, she wouldn’t be in … in this situation, sir.” Rachel was so intent on trying to save Sarah from her punishment, she was practically in tears. “I realise I have to be caned but surely Sarah doesn’t have to suffer as well, sir.”

Mr Grimes smiled. “What would you suggest as a punishment for Sarah, then Rachel?”

“I don’t know, sir.” Rachel looked at the evil looking cane still in the headmaster’s hand. “Does Sarah have to be punished at all?”

“Oh, I do think so, Rachel. I feel we must provide some little deterrent in case any other girl takes it into her head to interfere with another girl’s punishment.”

“Could Sarah perhaps have to wear school uniform for a day or two? Maybe have to do an extra dorm duty or two?”

“Something like your punishment, Rachel? The one you thought so little of that you believed you could cheat your way out of it?”

“Yes, sir.” Rachel murmured.

“Very well.” Mr Grimes diverted his attention to the smaller girl still bending across his desk. “Sarah, you may have three days of wearing school uniform, plus three evenings of dorm duty. Does that sound fair?”

“Yes, sir.” Rachel confirmed her agreement before Sarah could speak. She looked down at Sarah, expecting her negotiations on behalf of her friend to receive some favourable reaction.

Sarah, though, stayed right where she was. “Thanks, Rachel, but I’d sooner take the three strokes, if that’s okay sir?”

“The choice is yours, Sarah.” Mr Grimes looked towards Rachel, curious at the girl’s shocked reaction.

While Rachel stood dumbfounded, the headmaster held the cane horizontally and lined up his first stroke. He drew the cane back and then whipped it down until it collided with the tight black seat of Sarah’s leggings.


After a delay of nine or ten seconds, Mr Grimes took aim again and lashed the thin rattan down until it cracked across Sarah’s waiting bottom.

“Ooouch!!” Sarah responded with a louder squeal.

Undeterred, Mr Grimes raised the cane for the final stroke, delivered with even more venom than the previous two.


“Thank you, Sarah.” Mr Grimes went round to the opposite side of his desk, laid the cane on the top, and sat down. Sarah, meanwhile, gently unfolded herself from her bending position and began gently feeling through the material of her thin black leggings as she explored the damage done to her bottom.

“Sorry.” Rachel mouthed the word silently as Sarah turned to glare at her.

“You may leave us, Sarah, if you wish.” Mr Grimes peered at the girl over the spectacles sitting halfway down his nose. “Or I’m sure Rachel would have no objections if you felt you wanted to wait and see justice administered to her.”

Sarah needed no second bidding, she stood aside for Rachel to take her place across the desk and made it clear she would be watching every moment. Rachel smiled wryly. Mr Grimes picked the cane up from his desk, at which point Rachel moved forward to stand close to the desk.

“Your punishment will of course be more substantial, Rachel. Six strokes.”

“Yes, sir.”

The tall prefect waited while Mr Grimes manouvered himself into a suitable position behind her and Sarah came round to the opposite side where she would get a better view. When both seemed satisfied with their locations, Rachel bent down over the desk and surrendered herself for punishment.

Within moments, Rachel felt the back of her grey pinstripe jacket being lifted clear of her bottom and folded high up her back. She sighed, imagining the sight of her curvaceous bottom with the seat of her pinstripe trousers stretched so tightly as she bent over. “Is that really necessary, sir?”

“Indeed it is, Rachel.” Mr Grimes bellowed back. “I want nothing to interfere with the effectiveness of your punishment.”

Rachel braced herself. Immediately, she heard a sudden whoosh of air and an almighty crack as the cane whipped across the seat of her tight trousers.


The eighteen year old’s eyes widened as she felt the stinging sensation. She stretched her arms forward and gripped the further edge of the desk, which made her trousers stretch even more tightly across her bottom. A second swoosh heralded the next stroke.


Tears sprang to Rachel’s eyes as the stinging cane cracked across her stretched trousers seat, and she gripped the edge of the desk even tighter. The cane swished again.


Another couple of tears trickled down her cheeks as she felt the effects of the cane, stinging like nettles had been used instead of the pale yellow rattan.

Remorselessly, the sound of another stroke filled Rachel’s ears, instantly followed by the loud crack that echoed round the room.


Rachel’s knees sagged and her head bobbed up. She struggled to hold on to the edge of the desk, the knowledge that to stand up would be considered bad form and probably incur, at best, derogatory comments from the headmaster. At worst, there might be further sanctions.

“Please sir, can you stop for a moment? This is really hurting me!” She pleaded.

“That is the object of the exercise, Rachel.”

“I know, sir, but surely a brief respite wouldn’t do any harm.”

“Either we carry on, Rachel, or I ask Miss Harpethorne to come along and complete your punishment.” Rachel began to rise up from the desk, then paused as she pondered on the implications of that option. “Which would of course mean you would no longer be allowed the protection of your trousers!”

Rachel froze, then settled back down onto the desk again. Being caned by the robust senior teacher would not be any sort of easy alternative, and the idea of having to remove her trousers for the exercise made it even worse.

“Please continue, sir.”

After just a couple of seconds, Rachel heard the cane swishing down until it whipped across her tight trousers seat with an almighty crack.


A fresh bout of tears began to roll down Rachel’s face, and it was only knowing there was just one more stroke to take that kept the eighteen year old in position across the desk.

Rachel closed her eyes and waited. Finally she heard the whoosh of air, then the almighty crack, and then her whole bottom was set once more on fire by that stinging agony.


Rachel arched her back, causing her to half rise once more from the hard wooden surface of the desk. Tempted though she was to reach back and grip her aching backside, she resisted in case it angered her headmaster and led to yet more punishment.

“Yes, you may get up, Rachel.”

At last she had permission. Rachel eased herself up and began unashamedly massaging her sore bottom with both hands.

“Right, girls, you may both leave when you are ready.”

For the moment, Rachel continued ministering to her aching bottom. Mr Grimes returned the cane to the corner cupboard, and Sarah waited for Rachel. The sight of the headmaster coming back towards his desk was enough for Rachel to feel the urge to leave, whatever the state of her bottom.

“Thank you, sir.” She said grudgingly as she turned for the door.

“Thank you, sir.” Sarah repeated as she followed.

Mr Grimes merely grunted an acknowledgement.

The two girls walked slowly along the corridor, Rachel slightly ahead of Sarah, until Rachel heard the other girl’s voice in her ear.

“Quick! In here.”

Rachel stopped and turned, and found Sarah beckoning her into an empty classroom. They went in and Sarah closed the door securely behind them.

“That hurt!” Sarah commented, and in one swift move thumbed both her tight black leggings and brief white knickers down almost to her knees. They both inspected the three angry red stripes that lined Sarah’s creamy white bottom.

“I bet yours is worse.” Sarah hinted.

In response, Rachel unzipped her charcoal grey pinstripe trousers and let them slip to her ankles. She eased her pale blue panties down until her bottom was also quite bare, enabling them both to survey the six dark red weals that criss-crossed Rachel’s bottom.

“That should really turn Rodney on.” Sarah commented.

“Oh grief! How am I going to sit down on that bloody little car’s hard seat after this? And that suspension is so hard. I couldn’t bear the humiliation if Rodney found out about this.”

“Phone him up and tell him you can’t make it this evening.” Sarah suggested. “Tell him you’re being kept in or something. He’ll be expecting that after last night.”

“I don’t know.”

Just as the two girls began easing their underwear back into place, the door suddenly burst open.

“By the way.” Mr Grimes’ gruff voice made the two quickly pull up their trousers to cover themselves. “I shall be having a word with my nephew about his driving this evening, Rachel. Perhaps when I tell him the discomfort his actions have caused you two, he’ll drive with a little more courtesy. You did know Rodney is my nephew, didn’t you Rachel?”

The End