The Caring Headmaster - Cover

The Caring Headmaster

by John Key

Copyright© 2023 by John Key

Erotica Sex Story: Naughty new school master's wife meets the headmaster.

Caution: This Erotica Sex Story contains strong sexual content, including Blackmail   Coercion   Heterosexual   Mystery   School   Workplace   Cheating   Cuckold   Sharing   Wife Watching   Wimp Husband   BDSM   MaleDom   Humiliation   Spanking   Swinging   Exhibitionism   Petting   Voyeurism   .

“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 virtually 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 and throbbed 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, giggling 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 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, 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.

‘Future job offers’ might take forever, thought Dorothy, with a self-righteous smirk as 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 until now 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, 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...”

Dorothy’s heart raced as she stifled a gasp ... but 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, 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, Alan 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. “ ... 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 your husband.”

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 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 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 and shame that she’d been the architect of the poor secretary’s six stroke caning.

“Oh yes she is, she 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. 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 Alan ... he knows nothing about it ... I’m so sorry sir”

“You’re sorry? How dare you, how dare you Dorothy? ‘I’m sooooo sorry sir’...” 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 young lady ... and don’t you dare come back here until you’ve thought about what you’ve done...”

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... ‘never in all my years... ‘

Her urge to walk away was overpowering but she knew she couldn’t, she just couldn’t let her husband down. Alan was her husband, her clever handsome husband and there was no way in hell she’d ever let him down.

“Please headmaster, I’m truly sorry, I’ve been such a fool, 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 young lady. 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 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 ... 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 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.”

 
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