A curious mix-up indeed

By Hickory

Miss Moran, the assistant school secretary, walked confidently down the corridor to the Headmaster’s study. After turning the corner to arrive at her destination, she noticed a 6th form boy she knew as Morgan, waiting anxiously to the right of the large oak-panelled door. She shot him a quick glance, noticing his focus quickly drop with shyness as their eyes met.

Urgently seizing the large brass door knob, she swept into the Headmaster’s office. Mr Bloomsbury was seated at his desk writing an entry into a book.

“Get out, Morgan! I expect you to knock before entering, you rude individual!” not even lifting his head as he continued with his writing.

The sharpness of his expression and raised angry tone had jolted Miss Moran into contrition. Amazed at her forgetfulness, she silently chastised herself.

Without saying a word to the Headmaster, she realised she’d been mistaken for Morgan, the recalcitrant 6th former. Hoping not to be noticed, she hastily left the office, closing the door behind her.

Once outside, she again exchanged glances with Morgan and could feel her cheeks burning. The thought crossed her mind that Morgan would be feeling his cheeks burning soon in a rather more painful way, not least because of her actions of entering the office without knocking. This thought amused her greatly.

Straightening her back, she breathed in and raised her chin. She knocked the dark wooden door loudly and awaited the reply, her breath shortened as she gazed straight ahead. She ignored the jovial comment made by Morgan of: “Umm, I think he’s busy, Miss,” plus: “I’m a bit early.”

Eventually the word “Enter” was heard loud and clear. Miss Moran was again standing on the large round carpet some metres from the Head’s desk, her presence totally unacknowledged as she watched him continue his writing.

Miss Moran found her Headmaster a slightly intimidating man, tall with a commanding presence. His round thick-rimmed glasses betrayed his appalling eyesight. The whole school knew he was as blind as a bat.

He was her about father’s age and reminded her of a Hollywood film star, a bit like Paul Newman, a bit greyer and older, but they looked similar. Strangely, behind those glasses, he was, as she’d say, ‘quite dishy’.

In a well-practiced movement, the mortar board came swiftly off that fine head, the writing stopped abruptly and a long flexible crook-handled cane was plucked from a coat stand behind his desk.

“Bend over, Morgan; 4 strokes and 2 extra for not knocking.”

He was still not looking directly at her. Miss Moran stood still with her arms by her side. She smiled sweetly, hoping he was joking or was about to notice his error.

Nervously, she cleared her throat and stood her ground. “B-but Headmaster, I’ve umm…” She stuttered.

“Bend over, boy. This instant!” he shouted.

Nervously, she saw him flex his cane with a casual air of mundane resignation. He was now standing, but still some distance from her in the spacious office, and remained behind his desk. She noticed he faced slightly to her left, still not looking directly at her.

He began to take practice swings, testing the flex and balance of the long crook-handled cane, cutting the air with a vicious swishing sound, a bit like a golfer practicing a swing.

Her jaw dropped and her eyes widened. With an urge to obey, she quickly touched her toes. Surely this was all part of the game, but what a funny game this was, she thought. She felt a nervous grin stretch across her pretty features. Her shapely athletic legs kept straight, her hands grasped her ankles with her full round bottom presented high in the air.

Suddenly it dawned on her, the way she’d dressed today along with her short blonde bobbed haircut, light grey trouser suit, white shirt and school tie, she looked remarkably like Morgan, the 6th form boy waiting outside the office.

She was even wearing black brogues. Her enviable curves kept a feminine sexiness to her look, even when she dressed as a young male. Trying to slow her breathing, she felt the excitement rising, helping her keep her nerve and see this through, even have the last laugh. This must be a joke! Surely?”

It occurred to her that Mr Bloomsbury, with his appalling eyesight, might think that her curvy 22-year-old bottom, encased in tight grey flannel trousers, was that of a 16 year old boy and it was about to be thrashed! But surely not?

She heard him approaching her from her left. He positioned himself and addressed her bottom with the cane, again reminding her of a golfer when about to strike a golf ball. She felt a slight tapping sensation across her taut bottom.

The first stroke landed with a familiar swishing sound and a loud crack like a rifle shot.

‘My god that stung!’ thought Miss Moran, but not unreasonably so. She pursed her lips as if about to whistle, her eyes wide open and totally unfocused.

A sexy, exciting feeling mixed with adrenaline, caused butterflies and seemed to negate the burning feeling across her upturned bottom.

The reality had now sunk in. This was actually happening! With expert timing, the cane was aligned upon the tight woollen curvy dream of a target for the second stroke, allowing Miss Moran to feel the fire-like sensation across her bottom mature and her composure to return slightly.

THWACK!! The second stroke sliced into her rear. Gritting her teeth with eyes now tightly shut, she hardly made a sound. She felt as if she wanted to remain unrecognised, like it was her in a dream who was watching that wretched boy Morgan being beaten, and to her delight it excited her!

The shock was dawning on her now. This was actually, really, damn well happening!  and was a complete but rather exciting surprise!

A third full-blooded cut of the cane was absorbed stoically by the generous proportions of her grateful bottom and thick flannel trousers. She felt herself gasp but kept her legs straight, shoulder-width apart with her hands still grasping both ankles, she held firm and proud.

“Trousers down, Morgan, for the final three, boy!”

Oh no! Now what to do? Quickly thinking what underwear she’d put on that morning. Would this give the game away? Surely he couldn’t cane her bare bottom? He’d notice, wouldn’t he? It might hurt much more. What will he do? Or what will he say?

“Now, boy, or I’ll bloody start again,” he bellowed.

Standing up slightly, she undid her button and zip, then pulled the tight-fitting woollen trousers quickly down to her ankles. Eagerly resuming her position, she knew her bottom would now be bared as her choice of underwear had been small white panties that had travelled south below her knees along with her trousers.

She felt the air in the room being disturbed by the Headmaster’s gown, cool on her bare bottom. She was proud of her bottom, high in the air, and her tanned athletic legs. My what a target for the blind old bugger to not appreciate!

Three red parallel stripes showed vividly on Miss Moran’s fine white cheeks.

“Forgot to wear underwear this morning, eh Morgan? Too bad, boy. Brace yourself.”

“Hmm, perhaps he’s not that blind,” she thought.

THHWAACK!! as the fourth stripe whistled across her naked bum, the pain was far more intense and she couldn’t help producing a sort of grunt followed by a yelp.

“Oh, sir,” she quickly uttered, immediately thinking how similar in tone she sounded to some teenage boys.

Stroke five followed in due course, and was well taken with her position maintained. A sort of “oh ah” left her lips. It even sounded to her as if she was enjoying it. She damn well was! It was some time before the final stroke was administered. The Headmaster took several practice swings before unleashing the final stripe with utmost venom.

SWIISH THWAAACK! It landed square in the middle of Miss Moran’s five parallel stripes, filling the final gap to display six perfectly aligned livid welts.

The cane had landed perfectly on Miss Moran’s sweet spot, and on doing so had not caused her quite the pain one might expect. Her polite “oh, ah, oh Sir,” would have had most pupils moaning in agony, but had only left her thinking she might like to do this again one day.

She remembered that it was bad form to stand up immediately after being beaten, having heard stories of pupils receiving extra strokes for this offence. She thought this might not worry her, however. Her position was exciting to her as she felt the Headmaster standing behind her, surely trying to focus on her bottom.

“Get your trousers up and get out, and if there’s a next time it will be six on the bare.”

His tone was masterful and confident. She felt he couldn’t possibly understand the feelings in her head at that moment, and wasn’t even sure if she would want him to. Her hands clasped her welted bottom, she bit her lip and gasped, her once smooth bottom felt like a ploughed field and evenly spread, very neatly done.

‘Maybe his eyesight isn’t that bad,’ she thought. Standing up, lifting her knickers and quickly fastening her trousers, she noticed he was now seated again quite far from her in the vast expanse of this beautiful office, his attention on some papers to the left of his desk.

Her identity still intact, Miss Moran felt this would be a good time to turn and leave quickly, to study the stripes on her bottom in the girls toilets. The stinging was causing the tingling excitement to intensify. It had been painful but so enjoyable. The matter she’d come to discuss could wait or be conducted by telephone.

As her shaking hand made to reach for the door handle, she heard a further comment from the far end of the large wood panelled office.

“You took that extremely well, Ms Moran. Send in Morgan on your way out.”

She felt an electric shock course through her already aroused body, and she’d quite forgotten about that bloody boy Morgan out there listening to it all! And on top of it all, the Headmaster knew he’d been caning her pretty female bare bottom!

‘The canny old sod,’ she thought, and ached to reply with a witty retort but her voice failed her. She quickly glanced over her shoulder and saw him smiling to himself. She exited quickly.

“Go straight in, Morgan,” she said, her face beetroot red as the astounded boy gazed open-mouthed at his attractive female look alike.

Turning the corner, she rubbed her welted bottom and thought, although her bum was rather sore, was this really a punishment? And how to inform Mr Bloomsbury that the new arrival of canes had been lost in the post. And that she’d rather enjoyed her first experience on the business end of a cane.

The End

© Hickory 2020


This writer welcomes contacts from readers and can be reached by email at: markmark_cane@mail.com