Missed Opportunities

Richard stood by his bedroom door listening. Any moment now the front door would close and he would be alone in the house.

He could hear his mother bustling in the kitchen. “Come on, come on,” he was impatient to get on with it.

At last, the front door clicked into place. The eighteen-year-old dashed to the bedroom window in time to see his mother hurry down the road. She would be at work all day.

The boy pulled a straight-back wooden chair that was resting against the wall. It was his favourite chair. Often, he fantasised about that chair. But not now. This time it had a practical purpose. He moved it close to the wardrobe, stepped up on it, extended himself on tip-toes and reached for the John Lewis bag he had hidden on top.

The chair wobbled a little, but Richard steadied himself. Within moments he was safely on the ground.

He reached inside the wardrobe; grabbed his school blazer and tie and hurried out of the room. Seconds later he stood excitedly in the hallway, in front of the full-length mirror. He had been waiting a long time for this.

Richard was not a typical eighteen-year-old. He was about five-feet-seven tall and a little on the thin side. His mother always said he could do with “fattening up”. His tousled fair hair needed cutting and his face was scarred with acne.

He put the plastic bag by his feet and pulled on the blazer. It was an ordinary black school blazer. If it wasn’t for the school crest on the pocket it would be just like the blazers worn by tens (possibly hundreds) of thousands of schoolboys up and down the land.

He pulled up the collar of his white shirt and wrapped his school tie around his neck. He did the top button of the collar up and pulled the tie tight. He never wore it like this at school, but soon he would be visiting the headmaster: he needed to look neat and tidy.

Satisfied, he clasped the buckle of his wide leather belt and unfastened it. His jeans were cut loosely and the weight of the belt made them slide over his hips. Without unfastening the buttons, Richard tugged the blue denims to his feet and stepped out of them.

He paused to admire himself in the mirror. His white Y-fronts hugged his body slightly and contrasted against his hairless sun-tanned legs.

His heart raced. He bent down for the plastic bag, reached inside and extracted a brand new pair of school short trousers. They were beautiful; the real deal. Dark grey with sharp creases down the front and back. He stepped into them and pulled them up. The half-elasticated waist ensured a snug fit.

It said on the label they would fit “15 years”. Which school made fifteen-year-old pupils wear short trousers? Richard wished it were his.

It had taken him all his courage to buy the short trousers at the John Lewis store. Surely, the sales assistant would think him odd. But she didn’t bat an eyelid. She hardly noticed he was there. Perhaps there really were lots of fifteen-year-olds in short trousers that he never knew about.

His cock stiffened as he admired himself in the mirror. The short trousers were perfect; they fell to just an inch above his knees.

His outfit was almost complete. He delved back into the bag and took out a pair of grey knee socks, with red bands at the top. He sat down on the stairs and pulled them on. Then he laced up his shiny black shoes. He was ready.


He returned to the mirror, turned his back to it and bent down and touched his toes. He was ready for his six-of-the-best.

Richard had fantasied about corporal punishment for as long as he could remember. His favourite was making a trip to the headmaster’s study. In his imagination it was always some elite public school, where the boys boarded. He knocked on the door of the headmaster’s study, waited for the call from within, turned the handle, and pushed it ajar.

“Come in Rodgers,” the headmaster barked.

It was a huge study. The headmaster, resplendent in his flowing academic gown, stood in the centre of the room. To one side was an old, rather battered, desk that dated back at least a hundred years.

Dr Vigar didn’t stand on ceremony when it came to dishing out corporal punishment. A boy on the receiving end had to stand on his own two feet. Literally. Or to put it another way, the boy about to get a beating had to stand, bend over touch his toes and he had better not jump about as the cane cut his backside or there would be Hell to pay.

Richard entered the study. In fact, the headmaster’s desk wasn’t the first thing he saw as he went in. Behind the desk was a hat stand, six feet tall at least, and hanging from the top were six punishment canes of various sizes and thicknesses, all dangling by their crook handles.

Dr Vigar spoke clearly and decisively. “Stand there,” he indicated a spot on the rug that covered bare, polished floorboards. The headmaster already had his weapon of choice in his hand. “Face that way,” he used the stick to indicate the far wall.

“Bend over, touch your toes.”

Richard ran every moment through his mind; dozens and dozens of times; night after night.

He was wearing a posh green-and-gold blazer and grey short trousers. Dr Vigar, a fifty-something, swished his cane, touched it against the boys left buttock, took aim, drew his arm back to above shoulder height and let fly.

Richard saw his own smooth hands extended as they stretched out so the tips of his fingers touched the toes of his shoes. They were plain black shoes, of course. Highly polished: polished every night, whether they needed to be or not.

Richard also saw his grey socks, with green-and-yellow tops pulled up as tight as they could go. Woe betides a boy who wore his socks in any other way. The socks went to just below the knee and between them and his short trousers was an area of cold white flesh, maybe two inches between socks and shorts.

And, dangling in front of his face as he struggled to keep in position hung his school tie. A narrow specimen with large diagonal stripes: alternate, one green, one yellow.

Richard lingered on every detail. “Bend over, touch your toes,” the head had commanded. In one continuous moment he was over, fingers touching toes.  WHACK! WHACK! WHACK! WHACK! WHACK! WHACK!

“Stand up, send in the next boy.” And that was it. No ceremony really, just a simple ritual, familiar to generations of schoolboys. In, out, and a searing pain in the bum at the end of it. And a stiff, aching cock.

Richard looked back at his reflection in the mirror. He had a nice bum; the grey short trousers showed it to great effect. He parted his legs to get a better view.

Richard had never been caned in his life and was never likely to be. They didn’t use corporal punishment at his comprehensive school. Nothing. No canes, no slippers, belts or tawses. Not like Albury Grammar where his younger brother Anthony went.

Albury was a traditional school. And that included traditional discipline: the cane. Lots of boys were caned at Anthony’s school. Once, Richard remembered there had been some kind of clampdown on smokers. One playtime the prefects had rounded up about a dozen kids who had sneaked behind the gym to light up.

Wasn’t that wonderful, Richard thought. All you had to do to get the cane at Albury was to smoke a cigarette. Wow, he would be a twenty-a-day man. Who cared about cancer?

A rattling at the letter box of the front door startled him away from his memories. Richard saw the outline of the postman in the opaque glass. Unsure whether the postman could see him, Richard dashed into the living room and waited for the coast to clear.

The postman’s next call was three houses along. There he momentarily disturbed Mr Alan Tuckworth, a thirty-five-year-old bachelor.

Alan too stood in his hallway in front of the mirror. He had no new outfit; he was very satisfied with his ageing and rather tatty academic gown. It hung loosely from his shoulders and covered his tweed jacket and most of his worn black-and-white-striped trousers. He rather liked the authentic schoolmaster’s mortar board that lay askew on his head. The tassel that dangled from one corner was especially pleasing. He looked exactly like the schoolmasters in the old boys’ storybooks he collected.

In his hand he thoughtfully flexed a thick, but whippy, crook-handled cane. It was quite easy to get the four-feet of rattan to form a bow. It was dark yellow and had notches every three or four inches along its length.

He swished the cane through empty air. In his imagination he was Dr Tuckworth of St Eiseldown public school. In front of him was a sixth-form troublemaker.

“You again.” He spoke out loud, for he lived alone. He flexed the cane once more, eyeing up the eighteen-year-old in front of him.

“Well you were beaten before. Six on the seat of the bags.” He swished the cane, admiring the swooshing sound it made. “It obviously was not enough.”

Another swish of the cane.

“So this time you will be caned on your underpants.”

Tuckworth’s imagination was in full flow.

Swish! Swish!

“Take your trousers down, bend over and touch your toes, Rodgers.”

In his mind’s eye, his eighteen-year-old neighbour, reached for his belt buckle …

Other stories you might like

First day of term

Late home from school

The fire-raiser




More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second


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