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The Caring Headmaster

"The beautiful new schoolmaster's wife, meets the headmaster."

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"Oh, Oliver, this stuffy old school gives me the creeps," said Dorothy to her handsome husband, the new schoolmaster of the dreaded upper sixth.

Oliver agreed with his beautiful wife, "It is a bit old-fashioned, Dorothy, rigidly maintaining the 'traditional' school values, as everyone keeps endlessly repeating."

They were alone now in the school master's quarters after spending a tiring day being shown around the ancient academy. The first term hadn't started yet, so the school was virtually empty, apart from a few staff members and the headmaster.

The headmaster was friendly enough and eager to help, but they'd both had to pretend not to notice as the doddering old boy constantly gawked at Dorothy's bottom with undisguised relish at every opportunity.

"The other teachers seem OK, I suppose, Oliver, but I hate the way the headmaster kept staring at my bum."

"Well, it is a rather pretty peach, Dorothy. Can you really blame the old boy for drooling over your beautiful bottom? I bet his wrinkly old penis stiffened and throbbed that time you bent over to pick up the duster you'd carelessly knocked off the blackboard," teased Oliver to lighten the mood.

Dorothy responded with a shocked expression before a big, sexy smile split her pretty face as she playfully slapped his arm.

"Don't you mind that the old codger was ogling your wife's 'peach' and mentally undressing me? His beady little eyes twinkled as he thought of lifting my dress, peeling my skimpy panties down, and feasting his eyes on my bare married bottom."

"Not at all," countered her husband with a cheeky grin in response to his wife's sexy teasing. "As long as I'm the only one actually lifting your dress above your lovely, shapely legs, right up over your scrumptious peach." He said this as he teasingly raised her skirt above her waist. She spun around and saucily wiggled her bouncy bottom for him, giggling at her naughty tease.

"Oh, my word, you weren't joking about the skimpy little panties, Dorothy. The dirty old man can ogle all he wants, as long as I'm the only one who'll enjoy the pleasure of your sizzling hot bot. Dorothy, you really are such a naughty schoolmaster's wife. Imagine walking around in this short swirly dress with only a tiddly tiny thong to hide your modesty."

The old four-poster bed was surprisingly comfortable, with not so much as a squeak from the bedsprings, which was just as well.

"It looks like it's just you and the headmaster today, Dorothy. I have to meet up with the other teachers in the assembly hall to go over the curriculum for next term, which I strongly suspect will be at least as boring as it sounds. You, on the other hand, Dorothy, have the pleasure of reporting to the headmaster's study. Apparently, he likes to meet the wives for a pep talk and no doubt emphasises the importance of the 'old traditional school values'.

"The old traditional school values are so important at this institution, Dorothy; I really cannot emphasise that enough," droned the headmaster as poor Dorothy nodded solemnly.

"We pride ourselves on maintaining standards and discipline here. I, for one, take great satisfaction in the fact that this is the only school in the country with a corporal punishment license. It's never taken lightly, of course, but when a caning is required, then a caning there shall be."

"I didn't know caning was still allowed, headmaster; I'm not sure I approve."

"Oh, I find it's a very effective deterrent, Dorothy, and I'm sure you'll agree that it's so much better to get the problem dealt with straight away, rather than detention, lines, or, God forbid, expulsion."

The headmaster eagerly produced a crook-handled cane from the cabinet behind him. He swished the rattan cane through the air with an evil grin on his wickedly beaming face before he cracked it down hard on the papers, lying on his desk with a fearsome 'thwack,' which made Dorothy jump.

"I find that six stinging strokes from this little joystick will sort out any problem once and for all. Now then, let me just check that I have all the correct paperwork here," continued the headmaster as Dorothy stared wide-eyed at the ferocious yellowed cane. The headmaster had donned his gown and mortarboard for their interview that morning, and seeing him eagerly swishing his cane with that wicked expression on his fearsome face scared the hell out of her.

"Well, this can't be right?" Said the headmaster, frowning and startling Dorothy out of her daydream. "Ten years is written down here, but it looks like your husband has only nine years of teaching experience. The advertisement and job description clearly stated that a minimum of ten years was required at the coal face, or chalk face, as I like to call it."

A startled Dorothy remembered the discrepancy on the job application for this post. She blushed guiltily, recalling how she'd tried to persuade her husband to apply anyway. The starting salary was so generous, and the thought of all those lovely long holidays was just too tempting.

Despite Dorothy's pleas, Oliver had said no. He'd talked to a few of his fellow teachers, and they'd been adamant that the application would be flatly rejected and might jeopardise any future job offers.

'Future job offers' might take forever, thought Dorothy, with a self-righteous smirk as she secretly sent off his application, stating that Oliver had actually been teaching for ten years.

An interview with the board of governors was arranged, and her 'super smart' husband passed with flying colours. Oliver applied for so many teaching posts that he didn't realise this was the position that demanded ten years of experience.

Dorothy was relieved and actually felt a little tingly thrill at how clever she'd been. The ten-year requirement was never mentioned again, and until this moment, she'd forgotten all about it. 'We're here now anyway, so it's no longer an issue,' Dorothy thought reasonably, 'so I'll just say it was a silly mistake.'

Dorothy didn't know why she was saying it, even as she was saying it, and she was the one saying it, but she just blurted out the same blatant lie.

"Oh no, Oliver definitely has ten years of teaching experience, headmaster."

The headmaster stared at Dorothy with his piercing blue eyes. Dorothy felt her face redden with shame and embarrassment at this silly lie. 'God, what was I thinking? Surely it doesn't matter now if it's nine years or ten; Oliver's already got the job. Why didn't I just admit the 'mistake' and laugh it off?'

"Was your husband teaching before he left university?"

"Oh, I'm so sorry, headmaster. I was confused. It's been nine years, yes, you're right, Oliver has been teaching for nine years."

"I'm very sorry, Dorothy, but the school tradition is quite clear on this: The master for the upper sixth must have at least ten years of teaching experience. I think I know how this awful mix-up happened."

Dorothy's heart raced as she stifled a gasp. 'Oh my God, he knows, he knows what I did,' but she breathed a huge sigh of relief as the headmaster continued.

"It's our new secretary, we had so much trouble with her when she first arrived. She should have rejected your husband's application, it's basic mathematics, and instead, it appears she sent off an interview request, and the rest, as they say, is history. Of course, you can both stay here tonight, and we'll arrange transport for you back to the station in the morning.

Dorothy was horrified. Oliver had already left his last teaching job for this very well-paid position, and it was clearly too late for him to apply for another post before the start of term.

"Oh, please, headmaster, surely that isn't necessary, Oliver so deserves this job." Dorothy was desperate now, clutching at straws but determined to find a way out of the horrible mess she'd made.

"And really, it was the secretary's fault; you said so yourself, headmaster. Of course, I don't want her sacked or anything, but surely she should be punished for this and not my husband?"

"I don't know about that, Dorothy," frowned the headmaster, deep in thought, "Well perhaps." He tapped his fingers on his desk with a faraway look in his steel-blue eyes. "Yes, OK, then. I'll talk to the secretary and see what she has to say about this unfortunate pickle. Report back here at three o'clock sharp, Dorothy, and I promise I'll have a solution for this fiasco."

Dorothy's heart was thumping in her chest as she built up her courage outside the headmaster's office. She couldn't help feeling like a naughty schoolgirl, anxiously waiting to hear the headmaster's decision.

Tap, tap, "Ah yes, do come in, Dorothy, and have a seat."

"I've spoken to the secretary and told her that you felt she was the one who should be punished for the lie about the ten years of experience and not your husband."

Dorothy's face blushed bright pink. God, this was so awkward. Talking about lies and punishments and who's to blame had her heart racing like a naughty schoolgirl again.

"Good news, she accepted that she should have rejected the application and agreed to her punishment. Yes, it was a careless mistake, and she paid the penalty in full. Here's the signed punishment slip."

Dorothy took hold of the sheet of paper the headmaster handed her with growing unease. She gasped when she read the 'penalty' meted out to the unfortunate secretary, as dictated by the 'punishment slip.'

'I confirm that the application error was my fault and agree to my punishment of six strokes of the cane on my bare bottom, to be administered immediately.'

Dorothy read the punishment slip with mounting horror as she shifted her bottom nervously in her seat and stared in astonishment at the headmaster, eyes wide as saucers.

"Yes, she received those stripes very well, I must say," said the headmaster, smiling at the memory as he idly fingered the crook-handled cane, still lying across his desk.

"But, but, but she's a grown woman." stammered Dorothy in a state of shock and bewilderment and a gnawing sense of guilt and shame that she'd been the architect of the poor secretary's six-stroke caning.

"Oh yes, she is; she is indeed a grown woman, very much so," said the headmaster lecherously as he licked his lips. "She took her punishment accordingly, a six-stripe thrashing on the bare, without a single complaint and scarcely a whimper. So that explains how the erroneous application passed through our most rigorous standards, but alas, it doesn't excuse your husband from lying on his application form, I'm afraid."

"No, don't say it, headmaster. Please don't say it. It was my fault. It was me... I was the one. Oh, dear God, headmaster, I did it. I sent in the application for Oliver. He knows nothing about it, and it was only a tiny little mistake, and I'm sooo sorry."

"You're sorry? How dare you, how dare you, Dorothy? 'I'm sooo sorry,'" mimicked the headmaster in a whiny, pleading voice that made Dorothy cringe.

"Sorry doesn't cut it. Now get out, get out of my office, Dorothy, and don't you dare come back in here until you've thought about what you've done and are ready to atone for it."

Poor Dorothy slumped back against the headmaster's door, her face burning with shame and embarrassment. She could still hear the headmaster muttering to himself in his office, 'Never in all my years.'

Her urge to walk away was overpowering, but she knew she wouldn't. She just couldn't let Oliver down, not her Oliver, not her clever, handsome husband. There was no way in hell she'd ever let him down.

"Please, headmaster, I'm truly sorry. I've been such a fool; this is all my fault. Please forgive me, and I beg you not to fire my husband."

"Well, that's more like it, Dorothy. You seemed to have learned your manners and a little contrition, so I'm prepared to make an exception. Now then, Dorothy, I have your slip here somewhere; ah, yes, here it is." Said the headmaster as he nonchalantly handed her a sheet of crisp white paper.

Dorothy's breath caught, and she groaned out loud as she read her 'punishment slip,' with her heart pounding and blood rushing to her ears.

"But, but, but I'm a grown woman."

"Yes, yes, as is the secretary. I think we've already established this, Dorothy. Of course, we could still arrange for your transport to the station.

"Oh God, oh God, please no, I don't want to be caned, headmaster. I'm a grown woman; I can't be caned. You can't cane me; I'm, I'm a woman, fully grown." blubbered Dorothy.

"And why shouldn't a 'grown woman' be caned?" said the headmaster sternly as he gazed deep into Dorothy's pleading eyes.

"Oh, dear God, you're going to cane me, aren't you, headmaster? Oh no, no, no, I don't want to be caned, caned on my bottom. Oh Lord, no, you're going to cane my bottom, my bare bottom, but that's, that's, that's just so embarrassing, and six strokes too. Oh, Lord, will it hurt, headmaster?"

"A firm, round, plump bottom like yours, Dorothy, will really feel the sting of my cane. But I'm sure you'll agree that it's so much better to get this over and done with. We'll tear up your horrible, blotted copybook and wipe the slate completely clean. You'll have a nice, fresh start, Dorothy, and no one will ever know what you did. You're lying, and cheating will be completely forgotten, Dorothy and your devious deceit will never be mentioned again; it'll be our little secret."

Dorothy's heart thumped alarmingly as she squirmed in her seat. The thought of bending over to be caned, caned on her bottom, her bare bottom, was simply mortifying, but she didn't want her husband to find out what she'd done behind his back. He'd forgive her, of course. She knew Oliver was mad about her, but she just didn't want to let him down or for him to be disappointed in her. She couldn't bear the thought of his lovely puppy dog eyes looking so sad as they packed their bags after telling him what she'd done.

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Instead, she could avoid that awful guilty confession to her handsome husband, and all she has to do is bend over and take six strokes of the cane, and that's it finished. How bad can it be? Her caning will be in private, and nobody else will ever know. The secretary took her punishment 'with scarcely a whimper,' so perhaps it really is best just to get this over with, clear up the horrible mess she made, and move on.

Dorothy nodded to the headmaster as she signed her punishment slip and sealed her fate. The sexy new schoolmaster's wife was going to be caned, and that was the end of it. The headmaster's face lit up, with a twinkle in his eye, as he smacked his lips together in eager anticipation. A big, cheesy grin spread across his beaming face as he lifted his ferocious cane.

"Bend over my desk, Dorothy. Six strokes of the cane on your bare bottom for lying and cheating," the headmaster said sternly.

Dorothy's legs turned to jelly as she tottered unsteadily across to the headmaster's desk and bent over as ordered. He hummed to himself happily as he teasingly lifted her dress right up over her waist. She heard him gasp out loud as he feasted his eyes on her creamy white bottom with just her skimpy little thong nestled between her quivering bare buttocks, so teasingly pleasing.

"Please don't pull my panties down, headmaster," pleaded Dorothy. "Surely my panties won't protect me from your cane."

"I'm sorry, Dorothy. My hands are tied—school regulations, I'm afraid—a six of the best caning must be delivered on the bare."

Dorothy's face burned with embarrassment and shame as she felt his bony fingers eagerly tugging at the elastic waistband of her tiny pink thong, and she felt her panties sliding down her legs. Her last remnant of modesty nestled around her ankles, with her most secret and succulent parts laid bare. She slumped her head down in despair, vanquished and defeated by this horrifying humiliation.

The headmaster's cock twitched and throbbed as he peeled Dorothy's tiny little panties right down her sexy legs, all the way to her ankles. His mouth fell open in wonder and awe as he marvelled at the beauty and power of a grown woman's full, firm, quivering, bare bottom.

'Oh, my word, yes, please, that's a splendid bare bottom,' he thought dreamily as he gazed at Dorothy's lovely milky white buttocks. 'This beautiful bottom really is a juicy, succulent peach, ripe for the plucking.'

Dorothy was horrified and gasping for breath at this terrible injustice; she'd only told a tiny little fib to help her wonderful husband. Surely Oliver deserved this plum job for all his hard work over the years. Now here she was, bent over a stranger's desk, with her skirt up and her panties down, as a lecherous old man ogles her bare married bottom. 'Oh, my dear God, how did it come to this?' she thought miserably.

She shook with fear when the headmaster caned the air with a terrifying 'swish, swish, swish.' Dorothy wriggled her hips uneasily as her bottom squirmed with every horrifying swoosh. She stifled a gasp as a wave of tingles rippled through her, and she shivered in panic. Dorothy was afraid, bordering on petrified at the thought of what the Headmaster's monstrous cane could do to her poor bottom. She'd never felt so exposed and vulnerable before; she was completely helpless and totally at the mercy of this scary old man, who was determined to cane her.

The headmaster had excitedly lowered her panties like he was unwrapping an eagerly awaited birthday present. He prepared and presented her bottom to receive six stripes from his stinging fire stick, and there was nothing she could do about it. The shocking horror of being laid bare as her bottom was made ready for her punishment was truly terrifying, but the crazy floating-on-air feeling this total submission gave her was unbearably arousing. Her heart hit the floor, and her pussy pulsated and tingled when she felt that awful rattan cane tap, tap, tapping on her big, broad, bouncy, bare bubble bottom. 'Oh my God, oh my dear God, he's going to cane me, he's actually going to cane me.'

'Swish, crack,' and the first stroke landed across her jiggling jelly bottom like a squirt of fire. Dorothy gasped at the sting of the headmaster's ferocious cane as her bottom throbbed and quivered.

She was still gulping for breath and desperately clinging to the desk when the second stroke struck a withering blow. The fierce crack echoed around the room like a pistol shot as she pressed herself down against the cold, hard desk and felt the fiery flames spread across her scorching bottom.

The third stroke licked and nibbled at her burning bottom as she trembled and wriggled her hips to ease the terrible sting of the headmaster's wickedly whippy cane. She gasped as the headmaster's cold, clammy palm gently rubbed her well-caned bottom, and it was such a relief that she let out a grateful sigh. She instinctively raised her bottom to meet his tender caress. First, those awful stinging strokes from his nasty cane, and then his lovely, wrinkly old hand gently soothing her burning buttocks.

The headmaster loved the feel of Dorothy's peachy bare bottom as he tenderly caressed her jiggling butties. She'd relaxed as he massaged her blazing booty and raised her bottom up unconsciously towards the blissful reprieve. His eyes were like saucers as her pussy peeked out below her creamy marshmallow cheeks. So pretty and pink, her honey pot glistened and shimmered for him as the headmaster eagerly rubbed her rosy-red bottom in big circular motions.

The headmaster chuckled happily to himself as he admired his handiwork; three sexy stripes streaked across Dorothy's bottom, equally spaced and glowing a pretty pink. The wonderful 'swish, crack, splat' of his whippy cane on the new schoolmaster's wife's splendid bare bottom was insanely exciting.

His cock had stiffened and throbbed uncontrollably as each stroke struck home, and Dorothy's bottom jiggled and danced for his stinging cane.

"Three more stripes to come, young lady," crowed the headmaster, quickly followed by a horrifying 'swish' and the fourth strike cracked down hard on Dorothy's quivering bottom.

The fifth stroke snarled and snapped at Dorothy's still jiggling bottom. Her knuckles turned white as she grasped the desk, bracing herself for firecracker number six. She'd tried to keep her legs together up until now to maintain her modesty. She did not want the headmaster to see her most secret and intimate parts, but she just didn't care anymore as she spread her legs, wriggled her hips, and jiggled her buttocks, trying to ease the scorching sting of the sizzling hot cane stripes. Dorothy's bumhole squirmed as her swollen plump clitoris throbbed uncontrollably. The pulsating, panic-induced pleasure spread through her pussy, as she orgasmed to the sixth shocking stripe, which bit and nibbled at her big, bare bottom. It felt like the headmaster was holding a red-hot poker across Dorothy's blistered buttocks, which left her gasping for breath. She lay spent and panting across the headmaster's desk, thoroughly thrashed and with her glistening pussy still gently throbbing, as she clenched and unclenched her piping hot bottom cheeks.

"There, there, poor Dorothy, that wasn't so bad, was it? Now then, I'll just apply a little of this soothing cream, as per school regulations, of course."

The creamy lotion that squirted onto Dorothy's stripy, bare bottom and quenched the fiery flames made her groan out loud. 'Oh God, yes, what a relief,' thought Dorothy, with a whimpered sigh.

Now that the horrible caning was over, she felt the cane strokes merging together and a tantalising tingle spreading across her bare buttocks. She was enjoying the gentle massage from the caring headmaster as his gnarly old hands tenderly applied the creamy solace.

Dorothy was still bent right over with her married bottom completely bare and on display, but it mattered not a jot. She'd been caned by an old man who was now eagerly rubbing cream all over her stripy, bare bottom, and it just felt wonderful. It was such a powerful release, a fantastic escape from the guilt of her lying and cheating and the poor secretary being punished for her mistake, and now that it was all over, she was buzzing.

She wanted to punch the air in a victory salute, she'd taken a six-stroke caning on her bare bottom without even a whimper. The slate had been wiped clean, and her guilty conscience was completely cleared. She only wished she could tell her gorgeous husband what a lovely, loyal wife she was, taking one for the team. Her chest swelled with pride at her achievement, and she also felt a strange sense of trust and understanding from the headmaster.

Together, they'd suffered the horrible indignity of Dorothy's bottom being bared in preparation for her caning, her panties lowered to reveal her milky white buttocks, presented for a thrashing. Privately, they'd endured those awful, sharp, snappy cane strokes, the horrifying swish, and the shocking crack of the headmaster's firestick.

They alone had been through this incredibly intimate and deeply personal experience together, and Dorothy realised they'd shared something special between them. She knew intuitively that the headmaster felt the same way as he affectionately stroked and massaged her burning cheeks. She was so relieved that the awful blistering caning was over and the headmaster was clearly determined to rub her tender bottom all better that she arched her back and pushed her buttocks right up to welcome his soothing caress. This terrifying man, who'd unleashed wave after wave of biting bee stings across her dancing buttocks, was now gently fondling her bare bottom, and it felt so good she could have squealed with pleasure.

"Thank you, headmaster, thank you for caning me. I deserved to be punished, and it's such a relief to be free from the guilt and the shame of my lying and cheating."

The headmaster really enjoyed seeing the new schoolmaster's wife's beautiful round bottom, with the six scarlet stripes festooning her quivering cheeks. His heart raced at the feel of Dorothy's lovely, springy bare buttocks as he eagerly applied the refreshing cream. He wickedly lingered over areas where his merciless cane couldn't possibly have reached. 'Oh, I do enjoy a beautiful big broad bouncy bare bubble bottom,' he thought, smiling happily. 'This crisply caned and freshly creamed bottom is a tasty feast of eye candy. Oh my word, yes, her scrumptious bare buttocks really are double-delicious golden globes of joy. Dorothy's creamy pink and white, candy-striped bottom is just so achingly pretty.'

"Oh, there you are, Dorothy. Sorry, I'm so late. God, it's after six already," said Oliver, checking his watch as he greeted his wife with a kiss. "I got roped in with everybody else to give the retiring caretaker a good send-off. The old fool had a big dopey grin on his face too, as he heartily shook my hand, like he'd just won the lotto instead of his meager caretaker's pension."

"I'm glad to see you're smiling bravely after your pep talk with the 'headmaster' earlier. No matter what you had to endure, Dorothy, with that stupid old goat, I can guarantee you couldn't have had a worse time than me. I thought that meeting would never end."

"What do you mean, the 'headmaster'?" asked Dorothy, frowning as she mimicked her husband's annoying finger quotes around the word 'headmaster.'

"Oh, it's just so ridiculous; I fell for it too. It turns out the headmaster's been held up and isn't arriving until tomorrow. That doddering old fool we met is the caretaker. Apparently, they always let a retiring caretaker pretend to be the headmaster for any new members of staff. Everyone seems to think it's a great big joke, just another one of those ridiculous 'school traditions,' Still, I suppose it was all a bit of harmless fun.

Dorothy stamped her foot in anger. "Oh, that dirty old man," she seethed through gritted teeth.

"What do you mean, what happened, Dorothy?" asked Oliver, alarmed at his wife's sudden temper tantrum.

"I'll show you what happened," said Dorothy as she turned her back on her confused husband and bent over.

"This is what happened, Oliver, that bastard caned me," cried Dorothy as she lifted her dress.

Oliver gasped out loud as Dorothy's creamy bottom flashed into view with her tiny panties nestled deep between her quivering buttocks. Oliver's mouth fell open at the shocking sight of the six bright red cane stroke stripes emblazoned across his wife's bottom.

"He, he, he what, he caned you... but, but why, how?"

"He told me to bend over his desk, he lifted my dress and pulled my panties down, and then, God, I still can't believe it, he caned me. The 'headmaster' caned your wife, Oliver. Yes, that's right, Oliver, that dirty old man bared your wife's bottom and caned her."

Oliver's heart hit the floor as his cock swelled alarmingly. He was furious, seething with anger, but his penis was rock hard and pulsating uncontrollably as he gazed at his wife's quivering bottom. The thought of a stranger baring his wife's bottom and stroking her creamy, bare cheeks with his stinging cane was feverishly arousing.

"Oh, my God, yes," cried Oliver as he rubbed his hideously engorged shaft and squirted his piping hot cock juice all over Dorothy's stripy, bare bottom.

Published 
Written by JOHNKEY
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