How Many Strokes Will it Be?

z used cane holding (15)

Newbury wondered how many strokes it would be. He stood to attention, heart beating far too quickly, watching through rapidly blinking eyelids as the headmaster made his preparations. Dr Fortescue had been at the school less than two weeks. Already the boys had Christened him The Tyrant Headmaster.

Newbury sucked in a lung full of air. The room was stifling; not hot, but airless. Did the headmaster ever open the windows of his study? Dr Fortescue ruled the school with a rod of iron. No, that was not quite true, he ruled with rods of bamboos, Malacca, rattan and ash. Newbury stood in silence. Dr Fortescue busied himself at a cupboard. His collection of canes was extensive, he must select just the right one for the job in hand. He took one, dark yellow in colour, dense but whippy, three feet and more in length, a traditional crook handle. He swished it through the air, then flexed it between his hands. It was as if he had never met the rod’s acquaintance before. He peered at it intently, stone-faced; his white moustache bristled and his knitted white brows frowned.

Newbury licked his dry lips, waiting patiently. Dr Fortescue was an elderly man dressed in an old-fashioned, untidy academic gown. He was a commanding figure, rumour was he had once played prop forward in rugby. He was a tall, grim man and as strong as an ox. The senior boys of St Septimius could testify to that.

The headmaster had made it his business to raise standards from the moment he arrived. The school was going downhill, it needed drastic action. That was what the governors had told him when they appointed him. “Clean it up man,” were his orders. So, he started at the top, with the sixth-formers. Many of them, like Newbury, might be eighteen years old but they were still school pupils, still children. And they had better not forget that.

Newbury watched intently as the headmaster replaced the cane in the cupboard and selected another. To Newbury it looked exactly like the one he had returned, but the headmaster seemed to discover new properties it. He let it fly through empty air. It made a terrific swoosh! It looked like the one Dr Fortescue had used to thrash Rodriquez on his very first day at the school. Newbury blanched at the memory. Rodriquez prone across the table in front of the entire sixth-form, trousers down, buttock cheeks stretching his tight, white underpants and the headmaster flogging that very same Dragon cane into the firm young bum. Newbury clasped his hands behind his back to stop them shaking. The memory of his pal was all too recent.

The agony of the caning was so great Rodriquez had leapt to his feet. Two sixth-formers were ordered to hold him down, then the headmaster slowly bared Rodriquez’ bottom and whipped him with all his force. He had to be half-carried from the room at the end.

Newbury coughed dryly. Dr Fortescue had selected his weapon of choice, now he was making his preparations. The teenager took close note of how the headmaster’s arm muscles tensed as he picked up a heavy straight-backed chair and set it down in the centre of the room. His shoulder muscles tensed when he gripped a second chair and manoeuvred it so it stood back-to-back with the first. Satisfied they were in the required position, he ambled across to the bookcase and selected the first volume of the Encyclopaedia Britannica. It was a heavy book and several inches thick. He knew it would do the job in hand. He had no intention of reading it, he turned, walked across the study and set it down on the hard wooden seat of the first chair. Then he rested the cane on the top of his desk.

“Thieving Newbury,” Dr Fortescue snarled. “Such disgraceful behaviour.”

Newbury stared down at his shoes, embarrassed into silence. There was nothing he could say. He had been caught red-handed filching cigarettes from the corner shop. He wore his distinctive blue and white school blazer, there was no escape.

The headmaster frowned, his white whiskered quivered. “Theft is crime. You should go to court. You will have a record,” he leaned forward and Newbury recoiled. “There goes your place at university. Any hope of a decent career. You stupid, stupid boy.”

Tears formed behind Newbury’s eyes. Criminal record, a life ruined. It had never entered his head.

The headmaster paced the room slowly, tutting to himself; like so many schoolmasters he was a ham actor at heart. “But, Newbury,” he took hold of a hem of his gown and swished it across his body, rather like a magician about to complete a trick. “Help is at hand.” He straightened his back, shoved his shoulders forwards and (he liked to think) rather like his hero Winston Churchill, he barked, “Mr Scrimshaw, the shopkeeper, has agreed not to go to the police.”

Newbury’s heart skipped, this time with something approaching joy, not terror. “He will not press charges, if he is to be present at your beating.” The headmaster  strode to the door of an anteroom and with a flourish opened it. “Come in please, Mr Scrimshaw.”

A wizened man, hunchbacked, with a long sharp nose and pointed nose, shuffled into the room. His beaky eyes peered around the room as if he had transferred from a dark cave into a brightly-lit room. He stopped three feet in front of Newbury and very deliberately he examined the boy’s features as if ensuring that he was indeed the culprit who tried to make off with then Woodbines without payment.

“Please sit down Mr Scrimshaw,” the headmaster indicated a small comfortable armchair. Scrimshaw coughed a response and wheezing all the time settled himself down. He shifted his buttocks for comfort and leaned forward menacingly. He was making sure he had a perfect view of the drama about to unfold.

The headmaster picked up his cane and flexed it between his hands. “Whip him well Mr Headmaster, whip him well,” Spittle dribbled over Scrimshaw’s bottom lip. The headmaster’s eyebrows shot heavenwards, “Oh, I intend to Mr Scrimshaw, I intend to.” He turned toward Newbury and swished the cane through empty air, then pointed it at the two straight-backed chairs. “Stand there boy!”

Newbury clutched his hands behind his back, rather like the Duke of Edinburgh on a walk-about. Dr Fortescue stood close to him casting a show over the sixth-former’s body. Newbury caught the masculine aroma of stale whiskey, cigarette smoke and coal tar soap. “Lower your trousers and your underpants.” It was a simple, calm instruction. There was no need to engage in histrionics,  the headmaster was in charge, and he knew it.

Newbury turned his head slightly toward the headmaster, a look of incomprehension on his face. Dr Fortescue sneered, “Get on with it boy. Right down to the ankles, if you please.” Newbury’s head pounded, blood was rushing through his arteries to his temples. He felt unsteady on his feet. He gulped in air, afraid that he might faint to the floor. At last he got his shaking fingers to cooperate with his brain and the front of his trousers opened. He sensed Mr Scrimshaw lean forward in his chair.

Of their own accord the trousers slipped down his thighs and past his knees and settled in a puddle on top of his shoes. His white Y-front underpants were a little small and hugged the contours of his buttocks and cock. The musky aroma of the headmaster wafted into his nostrils. He gulped down saliva, slipped his thumbs into the waistband of his pants and guided them south. He had to bend his knees as he took them on their way, suddenly conscious that his bare bottom, crack and balls were on full display. A strange combination of a wheeze and a sneeze escaped Mr Scrimshaw’s mouth.

Newbury stood naked from the waist down, the long-ish tail of his shirt covering his privates and buttocks. The headmaster tapped his cane on the top of the encyclopaedia. “Lift up your shirt, kneel on the book and bend across the chairs.” Newbury stared at the cane in the headmaster’s right hand. It was about three feet in length, darkish yellow in colour and with the traditional crook handle. It was dense and had notches every three or so inches along its length. It was a terrific weapon, Newbury wondered if he might be permitted to stuff a handkerchief into his mouth.

“Over boy,” the headmaster’s patience was exhausted. He thwacked the cane across the book. Still, unsteady on his feet, Newbury gripped his shirt and hauled it up to his chest while simultaneously climbing onto the chair. The book was to rise his body so that his backside would be high, and as his body stretched across the chair backs, his buttocks would be at the correct height and angle to receive lashings into the underside (and most sensitive) part of the cheeks.

“Head down, bottom high,” Dr Fortescue intoned. Newbury wriggled into the required position and waited, conscious of his submissive position. His naked buttocks were twitching submissively, completely at the mercy of the powerful headmaster. There would be no mercy  that afternoon. Newbury was resigned to his fate.

Dr Fortescue stood a cane’s length from Newbury’s left side and began to saw the cane across the underside of the cheeks. He had beaten many buttocks in his career as an educator, the pair offered up to him now were quite typical. Newbury was well covered. He was in no way ‘fat’ but his bum has a certain amount of ‘give’ as the headmaster pressed his cane into the flesh as he took his aim. He tapped the cane smartly against a dimple that had formed under Newbury’s left cheek. The headmaster counted to five in his head, raised the cane high and with a strength nurtured over many years flogged the whippy rattan with maximum force across the centre of both cheeks. He was greeted by a thick dark pink line across the otherwise unblemished skin.

A hissing sound like a steam engine whistled through Newbury’s clenched teeth. He hands gripped the seat of the hard wooded seat. His back bucked, his head rose and fell. That hurt. That hurt a great deal. He heard the floorboards of the study creak as the headmaster paced. “Thank you Sir, may I have another,” Newbury spoke firmly. The headmaster paused pacing and glared. “What?” he did not say out loud. “I have never come across such a thing before. Such impertinence.” He took aim and the cane whistled as it flew though the air, the crack of rattan on stretched flesh bounced off the walls. Newbury repeated the buckling and the bouncing. This time a sharp yelp rang out. The headmaster paced.

“Thank you Sir. May I have another,” croaked this time. Dr Fortescue’s face, never clear at the best of times turned puce. “What!” again thought but unsaid. “Is he saying my flogging is not hurting? He can take anything I might offer?” The third lash struck across the top of the curves; there were now three livid red welts running almost parallel across Newbury’s buttocks. The headmaster had a terrific aim. He was (as it were) a master master. “Thank you Sir, may I have another.” The headmaster paced the floor, this time noticing Mr Scrimshaw was himself red of face. He was leaning forward elbows resting on knees stretching himself to get as close to Newbury’s prone body as possible without actually leaving his chair.

The headmaster tapped his cane ready for the fourth stroke. Perspiration soaked Newbury’s short hair, it looked as if he had just emerged from the swimming pool. The eighteen-year-old’s face was deathly pale. His knuckles were turning white, the muscles of his arms were taut as he gripped the chair for dear life. All saliva had drained from the headmaster’s mouth. He ran his tongue around it trying to make some moisture, tasting a tang of whisky. He took a deep breath, found his aim and whacked the cane across Newbury’s dimple. There was no yelp this time; the boy had shut his teeth together with such force he feared they might crack. The thumping at his temples had disappeared replaced with a light-headedness he had never experienced.

“Thank you Sir. Please may I have another,” his voice sounded as if had travelled from miles away. It did not sound to Newbury as if the words were his. The headmaster paced. Perplexed. Never in his life had a boy asked for more. By the fourth stroke many a boy – seniors as well as juniors – would be begging for mercy, promising to do anything if only the headmaster would stop the beating.

More pacing followed by more tapping. Swish! Crack! “Thank you Sir. Please may I have another.” The intense agony had started at the buttocks and then travelled up and down his legs; soon his whole body ached with pain. But by cut number five something unexpected happened. Newbury heard the swish, he felt the cane sink into his flesh and then … Nothing. There was no pain. The boy lay breathing heavily. Was his body now so numb that he was immune? “Thank you Sir. Please may I have another.”

The headmaster paced. Number six. Six-of-the-best. The very best. Dr Fortescue always finished on a high note. His special headmaster’s caning had already become infamous at the school. Newbury was not surprised to feel the headmaster alter his position. Now, instead of tapping the cane from left to right across the bared bum, he laid it in a diagonal from the bottom left to the top right of the buttocks. He let fly. A thick red line intersected the previously-laid five, reigniting and adding to the severe pain already inflicted. Newbury hung on. His mind was playing tricks. It was as if were floating on the ceiling looking down at himself submissively positioned across the chair, buttocks blazing. The headmaster, a little unsteady was at his cupboard replacing the cane along with his collection. Mr Scrimshaw rocked gently back and forth in his chair.

The headmaster sat at his desk, opened a drawer and pulled out a hard-covered exercise book. He fished in the inside pocket of his jacket and pulled out a pen. All this time Newbury lay still, trying to figure out this feeling. Was this how it felt to take drugs? The headmaster found a page in the book, wrote some words and closed it. Still seated he called to Newbury, “That’s it. Get up and get dressed.”

Newbury climbed from the chair and un-self-consciously massaged his buttocks. He swivelled his body and saw six impressive welts. Mr Scrimshaw stared at him intently as cautiously Newbury rubbed his index finger across the lines. His bum felt like corrugated cardboard. The headmaster sat back a little in his chair observing his senior pupil.

Newbury turned his back to Dr Fortescue then bent down to retrieve his underpants. It gave the headmaster an uninterrupted view of his savaged buttocks, his crack and hole and his ballsack. Newbury took a moment more than necessary to get his pants back in their rightful place. He turned and faced the headmaster’s desk. His cock was hard and fought against the already stretched cotton. He looked directly at the headmaster who could not return his gaze. Newbury pulled up his trousers and buttoned up.

And that was how Newbury came to worship Dr Fortescue with all his heart and soul.

Picture credit: Unknown

 

More stories involving The Tyrant Headmaster are here.

 

Other stories you might like

Caught in their underpants

Milo, the grad student

Two for the taws

 

 

 

More stories from Charles Hamilton II are on the MMSA website

 Charles Hamilton the Second

charleshamiltonthesecond@gmail.com

 

2 thoughts on “How Many Strokes Will it Be?

  1. Ah What an awesome story
    Caning descriptions always do it for me ..my mind is racing with images of welted bottoms and Jimmy Edwards circa “Whacko!” type of Headmaster’s brandishing well used punishment paraphernalia
    Canes of varying thickness..straps..paddles…hairbrushes…all used to cause maximum discomfort to bared bottom cheeks …I’m enjoying these stories immensely
    Well done sir!

    Like

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