tagBDSMThe Caring Headmaster...

The Caring Headmaster...


"Oh Alan, this stuffy old school gives me the creeps." said Dorothy to her handsome Husband, the new school master of the dreaded upper sixth.

Alan agreed with his beautiful young 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 round the ancient academy. The first term hadn't started yet, so the school was completely empty apart from a few members of staff 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 gawked at Dorothy's bottom, at every opportunity.

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

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

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

"Don't you mind that the old codger was ogling your Wife's 'booty' and mentally undressing me? His beady little eyes twinkling as he thought of lifting my dress up and peeling my g-string 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 gorgeous bottom." He said as he teasingly raised her skirt up above her slender waist. She spun round and saucily wiggled her pert bottom for him, as she giggled at her naughty tease.

"Oh my word yes, you weren't joking about the tiny little g-string 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 school master's Wife. Imagine walking around in this short sexy skirt, with only a tiddly little g-string 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...

"...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 empathise the importance of the 'old traditional school values.'

"The old traditional school values are so important at this institution Dorothy, I really cannot empathise 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 much better to get the problem dealt with straight away, rather than detention or lines or God forbid expulsion."

The headmaster produced a crook handled cane from the cabinet behind him and cracked it down hard on the desk with a fearsome 'thwack' that 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've got all the correct paper work here..." continued the headmaster, as Dorothy stared wide-eyed at the ferocious yellowed cane.

"Well this can't be right?" said the headmaster frowning...

"...ten years is written down here but it looks like your Husband has only nine years teaching experience? The advertisement and job description clearly stated that a minimum of ten years was required at the coalface, or chalk face as I like to call it."

A startled Dorothy remembered the discrepancy at the time of applying for this post, as she 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, Alan 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.

Dorothy felt a little bit guilty, when she secretly sent off his application, stating that Alan 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. Alan applied for so many teaching posts, that he didn't realise this was the position that demanded ten years 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 she'd forgotten all about it. 'We're here now, 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, Alan definitely has ten years teaching experience headmaster."

The headmaster stared at Dorothy unblinking, 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, Alan'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 nine years, yes you're right, Alan 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 teaching experience..."

"...I think I know how this awful mix up happened, it's our new secretary, we had so much trouble with her when she first started. 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, Alan 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, it was all my fault, I made the mistake not Alan and he 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 me?"

"I don't know about that Dorothy," frowned the headmaster, "...well perhaps..." he tapped his fingers on his desk with a faraway look in his eye, "...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 school girl, 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 experience and not you Dorothy."

Dorothy's faced 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 school girl 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 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.

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

"But...but she's a grown woman..." stammered Dorothy in a state of shock and bewilderment and a gnawing sense of guilt 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, without a single complaint and barely a whimper. Now then Dorothy, I have your slip here somewhere, ah yes here it is." Said the headmaster as he nonchalantly handed her another 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 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, you're going to cane me aren't you headmaster? But I don't want to be caned...caned on my bottom, oh my dear God no, you're going to cane my bare bottom...but that's...that's just so embarrassing...and six strokes too, oh lord will it hurt headmaster?"

"A lovely firm young 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 never 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 Alan was mad about her...but she just didn't want to let him down. She couldn't bear the thought of his lovely puppy dog eyes looking so sad, as she confessed to him what she'd done.

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 barely 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 little school master's Wife was going to be caned and that was an end to 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, it's six strokes of the cane on your bare bottom for lying and cheating," said the headmaster 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 skirt right up over her slender waist. She heard him gasp out loud as he feasted his eyes on her creamy white bottom with just her skimpy little g-string 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 his bony fingers eagerly tugged at her g-string 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 peel Dorothy's titchy little g-string right down her sexy legs, all the way to her shapely 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 that's a splendid bare bottom,' he thought dreamily as he gazed at Dorothy's lovely milky white buttocks. 'This bountiful booty 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 Alan 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 and 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 eagerly lowered her panties like he was peeling the wrapper off a candy bar. He prepared and presented her bottom to receive six strokes 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 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 when the second stroke struck a withering blow. The fierce crack echoed around the room 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 whippy cane. She gasped as the headmaster's cold clammy palm gently rubbed her well caned bottom and it was such a relief, she let out a grateful sigh. She instinctively raised her bottom up 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 pretty pink pussy peeked out below her creamy marshmallow cheeks. So cute and sexy, 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 cane on the new school master'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 to the dance of his cane..."Three more strokes to come young lady," crowed the headmaster, quickly followed by a horrifying 'swish' and the fourth strike cracked down on Dorothy's quivering bottom.

The fifth stroke snarled and snapped at Dorothy's still jiggling bottom and her knuckles turn white as she held the desk bracing herself for fire cracker number six.

The sixth strike was an absolute corker that bit and nibbled at her blistered bottom and left her gasping for breath as she lay spent and panting across the headmaster's desk.

"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 with each other and a not unpleasant 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 just didn't care anymore. She'd been caned by an old man who was now eagerly rubbing cream all over her stripy bare bottom and it felt absolutely wonderful. Such a powerful release, a fantastic escape from the guilt of her lying and her 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, her guilty conscience completely cleared. She only wished she could tell her gorgeous Husband of 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 with the headmaster too.

Together they'd suffered the horrible humiliation 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 fire stick.

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 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 just felt so good she could have squealed with pleasure.

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byJOHNKEY2222© 1 comments/ 4683 views/ 3 favorites

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