Another story from the old site. It brought mixed responses when first published, but also has its origins in a true story.

By Kenny Walters

“Everything okay is it, Mrs Cuthbert?” Charles Oakes pulled his black gown around him as though protecting himself from the answer.

“Of course, headmaster.” The secretary appeared puzzled by the incursion. “Why wouldn’t it be?”

“Oh, just checking there have been no other little problems I might have to deal with.”

“No other problems, headmaster.” Mrs Cuthbert replied calmly.

While the middle-aged secretary returned to typing away at her keyboard, the rather dapper silver-haired headmaster withdrew into his office and closed the door firmly behind him.

Back behind his desk, Charles picked up the telephone and pressed the button for a direct outside line. Moments later, his call was answered.

“Mandy? Can you talk?”

“Charlie, darling! Yes, Bill’s still away on his business trip. Are you coming round? I’m wearing your favourite jodhpurs. You know, the white ones that are very tight.”

“You say the sweetest things, honeybunch!” Charles dreamed away for some seconds before shaking himself back to the matter in hand. “Sorry old girl, but we’ve got a bit of a problem. Millie’s been caught behind the bicycle sheds smoking a cannabis joint.”

“Oh, the stupid little bitch! Damn her! Damn her! Damn her! What does this mean, Charlie? Surely you don’t have to call the police or anything?”

“No, nothing like that, darling. By rights, though, I ought to expel her. But I might get away with suspending her for a few weeks, maybe four weeks?”

“And how are you going to pop round for your little moments of entertainment with my daughter at home? You simply can’t suspend her, Charlie. And if you expel her, then what reason can we give if you’re seen around here with everyone knowing my daughter is at another school? No, you have to think of something else, Charlie. You have to!”

Charles thought for a moment. “The only other thing I can think of is to cane her.”

“Can you still do that, Charlie? She is eighteen now, you know.”

“Oh yes, it’s still legal, even for sixth form girls. Damned unusual, of course, but still feasible.”

“And, as we both know, it wouldn’t be an exactly onerous task, would it? The little minx is quite attractive, don’t you think?”

An image of Millicent Saunders, pretty and dark-haired like her mother, dressed in her sixth form uniform of grey skirt or trousers and black blazer, occupied Charles’ mind before he once again composed his thoughts.

“I don’t know what you mean, Mandy. You know all my desires are reserved exclusively for you.”

“Yeah, right!”

“However, in all seriousness, a few good whacks of the cane would solve a multitude of problems.”

“That’s sorted then. And give her a couple of extra hard whacks on my behalf. Damned minx! By the way, Bill is still going to be away tomorrow too so if you’ve still got your afternoon free you could come round. Perhaps you could bring your cane with you, darling.”

Charles chuckled. “You’d like that, would you? Getting your bottom whacked with my cane so soon after your daughter has had a taste of it?”

Mandy Saunders laughed softly. “It sounds delightful, Charlie. I’ll look forward to it.”

Charles Oakes replaced the receiver and glanced at the clock. It was three-twenty. He buzzed his secretary on the intercom.

“Mrs Cuthbert, could you fetch Millie Saunders? I think you’ll find her in the Art Room.”

Minutes later, Millie stood in front of the headmaster’s desk worriedly twiddling her long wavy dark hair. Even the dull uniform grey trousers and black blazer failed to spoil her shapely figure.

“Millie, come and sit down.” Charles gestured her towards a chair positioned to one side of his desk.

“Are you going to expel me?” Millie asked anxiously.

“Expel you? Good heavens, no!” Charles laughed rather too loudly. “Of course not, Millie! One of our star girls? Gracious me, no!”

“Me? One of your star girls, sir?” Millie looked curiously down at her headmaster.

“Absolutely, old girl. Come on now, come and sit down. Fancy a coffee?”

“A coffee? Um. Yes, alright, sir.”

While Charles buzzed Mrs Cuthbert again and ordered their coffees, Millie suspiciously sat down on the edge of the chair. The two occupants of the room exchanged odd, faintly smiling glances until Mrs Cuthbert brought their coffees and retired to her outer office.

“Now look, old girl, we do have to have a little chat about your little situation when Miss Akehurst found you being a trifle bit naughty behind the bike sheds.”

“I beg your pardon, sir?”

“Eh? Oh, sorry! I mean, when you were found having a little cigarette of the ‘not entirely legal’ kind.

“Ah, that. Sorry, sir!”

Charles took a deep breath. “I’m afraid, Millie, I am going to have to do something about that, you know. Breach of school rules and all that. Smoking on the school premises is definitely taboo, especially when it isn’t exactly Virginia’s finest.”

“Who’s Virginia, sir?”

“It’s a state in the USA, Millie. Famous for growing tobacco. Which, unfortunately, isn’t what Miss Akehurst smelt when she caught you. A bit more spice to it, if you catch my drift.”

Millie blushed and looked down at the carpet. “So, if you’re not going to expel me then, presumably I’m in for a long spell of suspension, am I? Mummy will be furious. She hates me around the place getting in the way of her riding sessions and the friends she likes to invite round.”

“Yes, actually I took the precaution of telephoning your mother before I spoke to you. I gathered she wouldn’t be at all happy about you being suspended. Then there’s the detrimental effect it would have on your school work, of course.”

Millie drained her cup of coffee, replaced the cup in its saucer on the edge of the desk, and leaned back in the chair. “So, if you’re not going to expel me, sir, and you’re not going to suspend me, what else is there? Presumably you are going to punish me in some way?”

“Yes. I have to set an example to the other girls, Millie. I’m sure you understand.”

“Detention, sir?” Millie Saunders exclaimed, amazed that her serious offence could merit something as mild as detention. Unless it meant she would serve every Monday and Thursday evening in detention for the rest of her school life.

“Not detention, Millie. That would hardly be appropriate as I’m sure you realise. No, your mother and I have agreed the best thing is for you to be caned.”

“Caned?”

“Yes.”

“Caned, sir?”

“Yes, Millie.”

“You’re not serious?”

“Very serious, Millie.”

Millie looked suspiciously at the headmaster. “You really mean it, don’t you sir?” The eighteen year old searched her headmaster’s face for some sign that what her ears told her wasn’t true. She met with a quite sympathetic but nonetheless steadfast expression.

“As I said, Millie, I have spoken to your mother and we both agree this would be the best option. A few moments of discomfort will enable you to stay at this school and avoid any interruption to your schooling. It’s for the best, Millie.”

“I can’t even remember when a girl was last caned, sir. Certainly not a girl in the sixth form.”

“It was last year, actually Millie. I gave a girl six strokes for, funnily enough, smoking in school.”

Millie saw nothing funny about it. Her face was like thunder. “Presumably that was for smoking tobacco?”

“Good point, Millie. Yes, it was. Perhaps we need to make it eight strokes in your case due to the, shall we say, slightly illegal nature of the substance involved in your case.”

“Eight strokes! That’s going to bloody hurt! Sorry, hurt sir.”

“Yes, I’m sure it will. But, like I say, it seems the better option, taking into account your own best interests in terms of your education.”

“A short, sharp shock, you mean, sir?”

“Exactly, Millie.”

Millie looked down again, considering her options. When, realising she couldn’t think of any other choice, she finally looked up she glared straight at her headmaster. “And there’s nothing I can say that will make you change your mind, sir?”

“I’m afraid not, Millie.”

Millie nodded, trying to come to terms with her sentence. Then another question sprang to mind. “When are you going to do it, sir?”

“Right now, Millie. Pretty well right now.”

“Oh!” Panic filled the eighteen year old and she sat bolt upright in her chair. After a few moments, the inevitability of what was going to happen settled within her and brought forth another question. “In that case, sir, can we get on with it?”

“Of course, Millie.” The headmaster paused. “There’s only one thing, Millie. Eight strokes of the cane mean, of course, that I’ll be administering the punishment across your bottom. You do realise that, don’t you Millie?”

Millie blushed deep crimson. When, finally, she spoke, she whispered: “Yes, sir. I did realise that.”

“Now Millie, the policy of this school is that the cane is applied only over one layer of clothing so that it’s fair for all and no-one can receive a lesser punishment by, well, wearing thicker clothing and that sort of thing.”

“Right.” Millie screwed her face in confusion. “What does that mean exactly, sir?”

“Perhaps you could pop out and change into gym shorts? Nothing underneath, I’m afraid.”

“And have to parade through the school in my gym shorts? That’s not fair, sir! And I’m not even sure I’ve brought my games kit in with me.”

“Well, I suppose we could postpone your punishment until tomorrow, Millie. Then you could bring something suitable.”

“What would you call suitable, sir?”

“Gym shorts, thin ones, like I said, Millie. Or perhaps pyjama trousers if you prefer.”

“I’m going to look a bit odd coming to your study in my pyjama bottoms, aren’t I sir?” Millie laughed loudly, almost hysterically.

Charles smiled as he, too, saw the humour. “Whatever, Millie. Just so you can present yourself to be caned in one layer of thin clothing. That’s all I require.”

“Why don’t I just drop my trousers, sir? I hear that’s how they do it at the boys school.”

“I hardly think that would be appropriate, Millie.”

“Why not, sir? I’m wearing knickers under my trousers. They’re thin. And you are a friend of the family after all, sir.”

Charles sighed as he looked back at the girl, clearly a younger version of her mother. “Well, if you would be happy doing that, Millie, then perhaps it would be better to get it over with now and not leave you to dwell on things all through tomorrow.”

“I would prefer it if it could be done as soon as possible, sir. Like now, I mean.”

“Of course, Millie. I quite understand.”

“So, what do I have to do?” Millie stood up, one hand ready to unfasten the button at the front of her trousers.

“One moment, Millie.” Charles Oakes pressed the intercom button and spoke to his secretary. “Mrs Cuthbert, would you bring me a cane and the school punishment book, please?”

“Yes, headmaster.” Mrs Cuthbert’s voice crackled from the intercom, her tone confirming her surprise to receive such a request. “Right away, headmaster.”

A few moments passed while Millie and Charles Oakes stared at different spots on the walls of the headmaster’s study, then there was a slight tap on the door and Mrs Cuthbert entered carrying a slender pale tan coloured cane and a red exercise book. Millie couldn’t help herself look round to catch an early sight of the cane, which meant she also had to catch the stare of Mrs Cuthbert as the secretary placed cane and book down on the desk.

“Is that all, headmaster?” Mrs Cuthbert continued looking at Millie, who lowered her head shyly.

“Thank you, Mrs Cuthbert. Yes, that will be all.”

“Thank heavens!” Millie declared, after the secretary had left the room and closed the door firmly behind her. “For one awful moment I thought you were going to ask her to stay.”

“You are entitled to have someone else present if you prefer, Millie.”

“No thank you, sir! This is going to be humiliating enough without that!”

Charles leaned back in his chair, savouring the moment. Millie let a few moments pass, became doubtful of the smug look on her headmaster’s face and glared.

“Right!” The headmaster suddenly sprang to his feet. “Let’s get on with it.”

Millie watched as the headmaster pulled a similar chair to the one she had been sitting on away from its position by the wall and moved it out into the centre of the room.

“That’s what you’re going to make me bend over, is it?” Millie asked the obvious, more to make conversation.

“That’s correct, Millie. Now would you kindly remove your blazer, please? You can wrap it around the back of your chair by my desk.”

The girl complied, feeling a little uneasy in just her grey trousers and white blouse. “It’s much thinner than I thought. It’s shorter too.” Millie stared down at the cane lying on the desk, a length of rattan cane about two and a half feet long and little more than a quarter of an inch thick.

“It’s a normal school cane, Millie. It will do the trick.”

Millie grimaced. “Yes, sir.”

“Now please come over here, Mille and stand behind the chair.”

“Don’t I have to take my trousers off, sir?”

“It’s up to you, Millie. You can either take them off or come over here and slip them down.”

“I’d better take them off, sir. Mummy will only complain if I let them get creased up while they’re round my ankles.”

“Very well, Millie,” Charles said with a hint of impatience.

The headmaster watched while the girl carefully unzipped her trousers, slipped them down and off, folded them and placed them carefully on the seat of the chair. The hem of her blouse was fairly short and he soon spotted the very brief black panties as Millie dealt with her trousers.

“I think I’m ready, sir.” Millie suddenly turned and caught her headmaster staring at her underwear. She gave the blouse a tug downward, but that still didn’t fully conceal her panties.

“Good. Come over here then, Millie. Stand behind the chair.”

Millie complied in sprightly fashion, her moves just that little too agile to hide her nervousness. She held on to the back rail of the chair. “Do I bend over now, sir?”

“One moment please, Millie. Now, when I ask you to bend over, I want you to get your head nice and low and your bottom well up.”

“That should make a nice target, sir.”

Charles ignored the cheeky comment. “It’s better for you if the strokes land on your bottom rather than the tops of your thighs so I want you, when you’re bending over; to keep nice and still and make sure your bottom is sticking out. Do you understand?”

“Yes, sir.” Millie answered glumly, realising fully how much this experience would hurt.

“Very well. Bend over.”

“The traditional command.” Millie’s observation was more to herself. She bent over the back of the chair and pressed her head well down, gripping the sides of the chair’s seat and feeling her brief black panties straining to contain the soft feminine curves of her bottom.

“Really grip the sides of the chair, Millie.” The headmaster advised. “This is going to hurt and it will be better if you can stay in position. Then we can get this over with nice and quickly.”

“Yes, sir.”

Millie felt her fingers aching as she held on to the edges of the chair for all she was worth. A brief swish ended in a crack, leaving the girl in no doubt the first stroke had been delivered.

“Ooooowww!! That hurt more than I was expecting!”

“I warned you it would be quite painful, Millie. Now hold still.”

The brief swish and crack were repeated and Millie snatched noticeably.

“Sheeeesh! That really smarts!”

“Keep still. You’re doing fine.”

“Okay, sir.” Millie barely had time to utter her response before a third stroke whipped across her bottom.

“Aaaaaaaaaargh!”

“Presumably your first experience of this sort of thing, Millie?” The headmaster paused as he studied the two, and now three, angry red weals forming on the bare portions of the girl’s bottom.

“Yes, sir.” Millie answered; alert for the swish that meant another painful dose of the cane was fast coming her way. She soon heard it.

“Aaaahh Aaaaaaaaaaaahh!” Millie rocked from side to side, believing this might in some way subdue the chronic pain.

“Never been spanked, Millie?”

“No, sir.” Millie stole a look round and saw Charles Oakes already taking aim at her bottom. She just managed to look down before the next stroke lashed across the seat of her black panties. “Sheeeeeeesh!!”

“Keep still, Millie.” The headmaster demanded as the girl wriggled from side to side.

“Sorry, sir.” Millie responded through gritted teeth. “How many is that, sir?”

“Five, Millie. You have three to go.”

Before the girl could speak again, another swish brought a fresh dose of burning pain across her entire bottom. “Aaaaaaaaahh!! God almighty!”

“Sorry, Millie, but it has to be done. You have to be punished.”

“I’m certainly being punished alright!” The girl declared. Any further response was halted by another swish. “Yeeeeeeeeeeoouuch!! Yee Gods!!”

With Millie swallowing deep gulps of air, Charles Oakes allowed her a few moments to compose herself. Eventually the deep breathing settled and Millie looked round.

“Is this the last one, sir?”

“Yes it is, Millie.”

“Thank God for that!”

“Hold still.”

Millie did indeed hold still, so that her ordeal could be concluded and she could think of getting dressed and coping with her burning bottom. A swish, longer and a little louder than before, ended with a louder crack that whipped into Millie’s bottom causing her to arch up with sheer agony.

“Oh my God!!!” Unashamedly, Millie grasped her buttocks in her hands and rubbed frantically. “Oooooooowww!!!”

“That’s it, Millie. All done.”

If Millie heard, she made no acknowledgement and continued to rub and massage her scorched bottom for all she was worth. Fully two minutes passed before she felt able to reduce her ministrations to a slow, pained, circular stroking motion. She realised that tears had trickled down her face and, after a wipe with the back of her hand, she realised too that her make-up was ruined. She knew she looked a mess when she turned to see what had become of her headmaster.

Charles Oakes looked up from behind his desk and paused, his pen hovering over the open red exercise book. “Just doing the paperwork,” he explained with a weak smile.

“Can I get dressed, sir?” Millie glowered back.

“Of course, Millie.”

The girl came back to the headmaster’s desk and snatched her trousers from the seat of the chair. She pulled them on in a mixture of pain and anger.

“Millie, I know you’re upset, but it had to be done. You’re the one who chose to smoke, and smoke cannabis too, on the school premises. You can hardly complain about being asked to pay the price.”

“It hurt!”

“I’m sure it did, Millie, but no more than you deserved.”

“Yes, sir.” The knowledge she had brought everything on herself did little to placate her; by the time she pulled her blazer back on, her anger had at least subsided.

“Would you like another coffee, Millie?”

“No, thank you, sir. May I go now?”

“Of course, Millie.”

The following afternoon, Charles Oakes was in bed. It wasn’t his own bed and he wasn’t alone. He and his companion were both naked. “So, how was it for you, darling?”

Mandy Saunders grimaced at the trite phraseology. “Not bad. Seven out of ten, perhaps?”

“Seven? Only seven? You little brat! I’m going to spank your bottom again.”

“Again? Oh please! Let me get across your lap.” Mandy wriggled her naked body into position and pushed the bedclothes clear so Charles could swing his arm.

The headmaster playfully folded one of the woman’s arms behind her back as she lay across him and caressed the globes of her bottom. “Nice bottom you’ve got there!”

“As good as Millie’s?”

“Almost.”

“Only almost? You cheeky sod! Ouch!” Mandy sank her face into the soft mattress as Charles began to spank her already reddened bottom. “Why didn’t you bring your cane? I was really looking forward to that.”

“I did bring it, actually darling. It’s in the sleeve of my jacket downstairs.”

“Then go and get it! I want to be caned, just like Millie.”

“Millie kept her pants on, actually darling.”

“Her pants? Only her pants? You don’t mean to say you made her take her trousers down? You didn’t? You did, didn’t you?” Mandy grinned broadly at the thought.

“Actually it’s school policy. Only one layer of clothing allowed. Since Millie didn’t have her gym shorts with her, I gave her the option of being caned the following day. She volunteered to take her trousers off so it could be done without any delay.”

“I bet that stung! Anyway, what are you waiting for? Go and get your cane.”

Charles thought briefly about pulling on at least his underpants, decided against it, and went down the stairs two at a time to where his jacket hung on a hook in the hallway. The cane was almost completely concealed in the sleeve and it took just a moment or two to extract it. He bounced back up the stairs to find Mandy had placed a pillow over the end of the bed and was now bending across it, quite naked.

“Is this how it was for Millie?” Her mother asked.

“Not having a bed in my office, I had her bend over the back of a chair actually, darling.”

“Well, give me twelve of the best like this, then we can try it with me over the back of a chair.”

“Your wish is my command, darling.”

Charles swung the cane and delivered the first stroke rather more gently than the day before with Millie.

“Harder, harder! I can barely feel it!”

The headmaster continued the strokes with increasing verve until the cries from Mandy Saunders became a little too meaningful. “Shall we try it with you bending over the back of a chair now, darling?”

“Okay.” Mandy eased herself up from the pillow on the end of her bed and started rubbing her bottom. “What about the chair from my dressing table?”

Charles looked round and saw the small woven cane seated chair near the window. He brought it out into the centre of the room. “There we are. Now, bend over, girl!”

“Oh, you’re just so masterful!” Mandy stopped rubbing her bottom and bent over the back of the small chair, deliberately thrusting her bottom out. “Is this how it was for Millie?”

“Very similar, darling. Very similar.”

“Oh good! The little minx deserved a good hiding. I should have done it myself years ago.”

“So, do you deserve a good hiding, young lady?”

“I do, Charles. Very much so.”

“Then hold tight!”

Charles administered stroke after stroke, not too hard, but hard enough to cause Mandy to cry out each time the cane lashed down onto her naked bottom. Both participants were so engrossed in their pleasure they gave no thought to anything outside their own little domain.

“Good grief! Whatever is the meaning of this?”

Charles spun round towards the bedroom door and Mandy eased herself up from the chair.

“Bill! What are you doing home at this time of day?” Mandy asked, subconsciously rubbing her bottom and totally ignoring her nakedness. Looking beyond her irate husband, she saw her daughter standing wide-eyed.

“Mummy! Did I have to take a caning just so I wouldn’t get in the way of Mr Oakes coming round?”

“Oakes!” Mr Saunders roared. “Get your clothes and get out of here. You can put them on outside. Then get back to your school and, if you’ve any sense at all, you’ll write out a letter of resignation. Believe me, your days as headmaster are over!”

“Look, can’t we sort this out some other way. I’m dreadfully sorry.”

“Just get out, man! And count yourself lucky I don’t give you the hiding you deserve!”

Charles dropped the cane and quickly grabbed his clothes together while Mandy Saunders looked around for something to wear. She found her nightdress lying on the floor.

“You can leave that cane where it is!” Bill Saunders shouted when Charles stooped to pick it up. “Now, just get out!”

As the headmaster bolted through the door, Mandy Saunders searched for the sleeves of her nightdress to slip her arms through.

“You can forget that!” Her husband thundered. “Since you obviously like being caned and, so it seems, don’t mind your own daughter being caned too, you can bend yourself back over that chair. Be very certain, though, I shall be using much firmer strokes than lover boy! This will be one caning you won’t enjoy!”

The End

© Kenny Walters 2011