Naughtiest boy in the school?


Roland was bent over, hands placed firmly on his hairy knees, legs planted apart, staring down at the shiny, highly-polished tan floorboards. His mid-grey trousers were in a puddle at his feet, hiding his scuffed black lace-up shoes. His green-and-gold-striped tie dangled in front of his face.

Roland could have been the naughtiest sixth-former at St. Francis Independent Grammar School. This wasn’t his first time he was in this position and it certainly wouldn’t be his last.

Mr. Trout had his rituals at such moments. He waited until a boy was bent double, hands on knees, backside jutted out. Then satisfied that the buttocks were perfectly positioned to receive the administrations of his whippy rattan cane, he would take hold of the elasticated waist of the white school-regulation Y-front underpants. He would pull them tight so they created a wedgie effect, drawing tight cotton up into his crack. An inexperienced boy might think Mr. Trout was preparing the underwear so that it formed a second skin against the meaty buttocks.

Frequent visitors to Mr. Trout’s room knew better. The elderly man was merely toying with the quivering boy, bent submissively before him. For Mr. Trout had only one intention. He would release his grip on the pants and then count silently up to ten. Then, in a flourish like a magician whipping away a cloth, he would retake his hold on the waistband and tug the underpants down, across the mounds until they rested at the thighs. Usually, gravity helped them to slip down to the boy’s knees. Only later, once the thrashing was underway would the writhing of the punished lad take them down to meet his trousers.

Another part of the ritual went like this. Mr. Trout had not yet selected the cane he would use. He liked to leave the boy bent over, bare arse to the wind, while he sauntered to a tall thin cupboard in one corner of the room. Roland, even in his prone position was able to watch Mr. Trout’s legs as he moved about his business. They were sturdy legs, encased in expensively-tailored black trousers with white stripes. Roland could not recall ever seeing such trousers worn by anyone but Mr. Trout. A tatty academic gown hung loosely from Mr. Trout’s shoulders. In his bent-over position, Roland could not see the mortar-board cap balanced precariously on the housemaster’s head.

Roland raised his body slightly, but still with his palms firmly pressed into his knees (for he did not want to give Mr. Trout cause to award him extra strokes) and watched as the elderly man rummaged into his own trouser pocket and retrieve a ring containing several keys. Mr. Trout fumbled until he found the correct one which he inserted into the cupboard lock.

Mr. Trout’s back obscured Roland’s view. It made little difference because Roland already knew what was contained therein: a selection of school punishment canes of various lengths, thicknesses and density. Mr. Trout scrutinised the inside of the cupboard. Roland heard the tell-tale rattle as canes were moved about to facilitate the elderly man’s search for the exact rod he wanted to take the misbehaving boy’s backside off.

Roland saw Mr. Trout’s feet shuffle as he reached in and took hold of his weapon of choice, then he closed the cupboard but did not lock it. His feet moved sideways as he slowly made his way back to where Roland waited submissively. This was the part Roland anticipated most. He had been beaten many times before, and not just with a whippy rattan cane. His backside had been blistered with leather tawes, rubber-soled gym shoes and wooden-backed hairbrushes. Each implement could inflict the severest pain, but each spanking and beating he had ever received – and there were too many for him to count – had its own unique property. At the point he waited for the first blow to land he could not know for sure just how painful it would be.

Mr. Trout liked to put a lot of beef into his beatings. It should be excruciatingly painful. What was the point, he would often say to Roland, of beating him otherwise? It should be awesome; something that the boy would not forget in a hurry.

Roland watched Mr. Trout’s feet. His brogue shoes were highly polished. They now stood to the boy’s left side. He could hear the elderly man swipe the cane through empty air. He stood so close to Roland the boy felt a breeze against his naked bum and legs as the rod whistled by. Mr. Trout planted his left foot firmly on the floorboards, and stretched the other away to the right, while also bending the knee. Roland took this as his cue. He couldn’t see, but he knew Mr. Trout was about to raise the cane way above his own head. The boy shut his eyes tightly, clenched his teeth and waited for the inevitable pain.

Mr. Trout was an expert with the cane. His eye was perfect; not for him the constant tap, tap, tap of rattan against bare flesh as he took aim. Instead, he simply raised the cane high and brought it smashing down across the very centre of Roland’s two buttocks. Bullseye! The rod sank into Roland’s bum and immediately bounced off, leaving behind a white stripe. Mr. Trout waited; he was in no hurry. Within seconds the white had turned to a deep pink. The faintest welt was rising.

Roland rocked on the balls of his feet; his mouth opened and closed, but he made no sound. A sharp pain attacked his rear, but very quickly it turned to a warm glow. He had absorbed stroke number one. Mr. Trout had not announced a tariff; Roland had not been told how many cuts to expect. Of course, it was traditionally six-of-the-best. Schoolmasters across the ages had been punishing their charges in such a manner. But, Roland was a recidivist, a repeat offender, the days when Mr. Trout considered six strokes a sufficient punishment had long past.

Roland watched once more from the corner of his eye as Mr. Trout positioned his feet. When he had judged that the hurt was ebbing away: Swipe! Number two fell, maybe a quarter of an inch below the first, but there was still plenty of room on Roland’s bottom for lots more strokes. The pain rose sharply to a new peak.

By the time he had finished the whole of Roland’s bottom, from the top of the mounds, across the very apex of the cheeks and into the fleshiest underside where the bum nearly meets the thighs would be covered with perfectly parallel lines. That was only if the boy was able to maintain his position manfully under the onslaught.

If he could not and his bum wriggled and squirmed or his legs buckled and he hopped from foot to foot; or, if his hips swayed backward and forth. If the wretched boy made any of these movements, it would destroy Mr. Trout’s aim. If that happened strokes might land in the same place more than once. The pain Roland already experienced would transmute to intense agony, as the pain from an existing ridge would be reignited. Blood might also weep from wounds at the points where one weal intersected with another.

Roland had a high pain threshold. He could take one heck of a beating stoically. But Mr. Trout knew how to lay on a caning with some vim. The pain in Roland’s backside mounted as each successive stroke connected with his jutting backside. His heart raced, blood coursed through his arteries, he found it difficult to catch his breath.

Roland rarely yelped or yelled during a thrashing. Instead, he would hack a dry cough after each swipe bit deep into his stretched flesh. This was unusual for a boy being punished. The first time Mr. Trout thrashed him, the elderly man had become concerned. He genuinely feared the boy might be in need of medical attention. The last thing he wanted was for Roland to vomit all over his expensively-polished floorboards.

Two more cuts landed, one after another. “Yowch!” Roland gasped, his face scrunching up with the pain in his bum. But, he managed to stay in position, hands on knees, face down staring at the floorboards, bum jutted out. But, three strokes later, his knees buckled and his torso twisted and he let out a shrill scream. The agony was too much; even for him. The next cut had him fighting back the tears.

Eventually, Mr. Trout’s shiny shoes disappeared from his sight. He knew then that he was returning the cane to its place in the cupboard. But, still Roland waited, his bum ablaze with pain.

Mr. Trout had a ritual to end his canings. He slapped Roland with the palm of his hand on his raw, corrugated rear. “Ouch!” he cried, and wriggled his blistered bum from side to side. It hurt almost as much as a stroke of the cane.

“You may stand,” Mr. Trout intoned. Roland blinked and straightened up. He saw the elderly man gaze at his cock and balls. He had seen them many times before and much more besides while Roland presented to him his bared bottom.

Roland tugged first his Y-fronts and then his grey school trousers into place. “Thank you,” he smiled courteously.

“You’re welcome,” the housemaster replied as he rested his backside on the edge of his desk. “And how is your wife? I read she was recently appointed Under Secretary of State for something or other. It keeps her very busy in London, I presume.”

Roland nodded, “Yes, I hardly ever see her.”

Mr. Trout rubbed his hands, “I’ll be seeing to you again before she gets back, I presume?” he asked him with a big smile.

“Yes please,” smiled back the thirty-five-year-old former pupil of St. Francis’s. “If you don’t mind.”


Other stories you might like

The housebreaker

Late home from school

The casting couch


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second


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