The Gaffer of The Academy 2. In the chill of the night

A Gaffer of the Academy story. For more click here
A Gaffer of the Academy story. For more click here

Picture the scene: An empty classroom, late at night. Outside: dark, cold, snowy. Inside: The Gaffer, wearing his gown; me in my pyjamas, trousers around the ankles, bending over a sloping desk at the front of the room.

I had no one to blame but myself. The Gaffer had impressed the rules upon us time and again and we knew the penalty if we disobeyed. That morning I had been spotted out of bounds in the town by one of the junior masters and had shown insufficient regret.

And, that was how I came to be in the cold classroom after lights out with my bared bum up in the air. Moments earlier The Gaffer had given me his (by now) ritual sermon about unacceptable, disgraceful behaviour – totally unexpected of sixth-form boys who were also prefects. I listened in a dazed state – unable to take my eyes off the dreadful man in his greasy jacket and oversized academic gown. I despised the man, even as I was terrified that he could punish me in any way he wished with impunity.

His rehearsed speech completed, he got down to the main business of the evening.

The Gaffer walked to behind the schoolmaster’s desk and opened a cupboard. I could see a number of canes laid out on a shelf. He extracted the longest and thickest one, closing the door before returning to deal with me. This cane had become a favourite of The Gaffer’s in the short time he had been at The Academy. It was a crook-handled senior cane about the thickness of a pencil that he used on the older boys when he wished to ensure that his message was clearly understood.

This particular model had more spring than flexibility and this meant a significant degree of bite. Boys left with weals rather than stripes on their bottoms and it was very effective even when used across the seat of a boy wearing his trousers and underpants. Across the bare flesh it was agonising.

To me, the cane looked threatening with its long, fairly thick, sleek, shiny, slightly curved shape. I had heard boys describe how it curled itself around the buttocks and delivered long lines of smarting, stinging pain, which increased with each stroke until the agony was beyond human endurance. I had seen the results of such canings, emblazoned on the buttocks of fellow sixth formers.

I thought they were exaggerating the agony, many of the boys were ‘teenager poets’ after all. I had boasted to myself that when my time came (I was sure it would inevitably come to each and every member of the Sixth) I would not cringe, writhe or wail. I had taken a few canings in the fourth and fifth forms, and they had never been that bad. But, as it turned out my brave resolve was misplaced.

“Now I have very simple rules for this: you bend over the desk and grab hold of the legs. I cane you,” The Gaffer said. “Then you stay in position for the next stroke. Anything different and the stroke will not count: I repeat it and add another one to the overall total as well. Understood?”

It was probably meant as a rhetorical question, but I meekly answered nonetheless, “Yes, Sir.”

“Now take down your pyjama trousers and bend across that desk and present your bare backside to me,” he swished the cane as he pointed it at a single-seater desk in the front row.

This command had not been unexpected. After the shock of witnessing McCain’s over-the-knee spanking on his underpants we boys soon learned that The Gaffer specialised in cruel and unusual punishments.

I was shivering, but not only because of the freezing temperature inside the classroom. I had never been so scared in my life as my fingers fumbled with the pyjama drawstring and I let down the bottoms until they lay in a heap on top of my bedroom slippers.

“Six strokes. If I were feeling less lenient you would be about to receive twelve for your disobedience and rudeness,” he said.

I shuffled forward a step or two and lowered myself across the slopping school desk, in exactly the same way, grabbing the thin wooden legs one in each hand, as I had when the maths master Mr Thompson had caned me in the Fifth.

At my height I fitted perfectly across the desk, presenting my bottom at a forty-five degree angle to receive the lashes from the Gaffer’s cane. I had been in this position before, but never with a bared bottom and with my crack and balls on full display to my punisher. I felt totally humiliated. I really wanted to run away and despite promising myself to be brave, I found that tears were beginning to prickle the back of my eyes.

I wasn’t to know this, but The Gaffer took a few moments to size me up. He thoroughly enjoyed beating the backsides of teenaged boys and he very much admired the sight of me bent across the school desk, offering myself to him dressed in my red-and-white-striped-pyjamas with the trousers bunched at my feet.

I was eighteen years old and had grown to my full height of 5ft 9ins and already weighed about ten stones (one hundred and forty pounds). When I bent across the sloping desk I presented smooth, very muscular thighs that spread almost imperceptibly into broad, meaty, hairless buttocks. My cheeks did not jut out much, but they provided much more padding than many backsides.

These buttocks, The Gaffer reckoned, could take a great deal of punishment. They were so meaty that it would be difficult to cause any damage. So, he could really give it to me – and he could not wait to get started with his cane. Roughly he gripped the tail of my pyjama jacket and dragged it a foot or so up so I was naked for him from the small of my back to my feet.

Then sounds of a cane being tested and swished through the air filled the silent vacuum of the classroom producing a chilling sound which made me shiver. After tapping my behind a few times to judge the distance, he raised it high and swished it hard into my trembling backside. I heard the swish then felt a searing white heat of pain across my bum cheeks as though a rapier had ripped across them and a burning throbbing welt began to swell, making me gasp for breath.

Once again the cane struck low down this time right across the top of my thighs, I yelped and the tears poured down my cheeks. As each stroke cut into the meaty flesh there was at first no pain and then within seconds I felt an excruciating stinging sensation. It was unbearable and much worse than any earlier caning I had endured.

The Gaffer was an expert with the cane. He started at the top of my buttocks and covered all the way down to the crease of my bottom and thighs before laying the sixth and final cut in a diagonal line right across the other five. Each stroke caused me to buck, but the last one just about lifted me off the desk and my feet left the ground. My bedroom slippers were kicked across the classroom as my feet stamped up and down as if performing a military dance.

Stunned, racked with pain, my finger nails dug into the palms of my tightly clenched hands as I held myself over the desk for dear life.

The Gaffer left me laying across the desk as I wheezed, gasping to catch my breath. The agony coursed through my entire body and I could feel deep welts now criss-crossed my buttocks. My tears would not stop and my shoulders heaved as I continued to cling tightly to the school desk.

The Gaffer took his time to admire his own handiwork. There were six angry lines of purple; five in parallel symmetry across my still vibrating cheeks and one going from the bottom left to the top right making the pattern of a five-bar gate: blood oozed at points where the final slash intersected with the previous ones.

Bruises had already formed across the edges of the cheeks where the tip of the cane had wrapped around the globes. The overall impression was that my bottom had been thoroughly whipped and now somewhat resembled raw hamburger meat.

I heard the cupboard open and the cane being replaced, but I stayed staring at worn floorboards. My buttocks agonized like crazy and I very much wanted to sit down in something very cold to try to relieve the aching.

The Gaffer was not a man to be rushed. As he looked down at the soft round bottom and the red striped mounds, he was in no doubt that I had been most severely punished.

After what seemed like an eternity The Gaffer ordered me to get up. I stood behind my desk and didn’t move. I just looked at the top of the desk. My backside was throbbing like I had never experienced in my other canings. At that moment I resolved that I never wanted another beating again while at this school. I didn’t realise that I was still naked from the waist down and The Gaffer had a full view of my swollen buttocks and my manhood.

It was not his style to lecture a boy at the end of a thrashing, so he simply told me to pull up my trousers and go, adding that if I wanted a repeat performance one day, I should expect twelve strokes.

I hobbled from the room very aware of the freezing cold. Checking to see that The Gaffer was not following me, I dashed out of the building, lowered my pyjama bottoms and sat down heavily on the frost-covered lawn.

That night in the dormitory I lay face down on the bed with the sheets rolled back allowing the air to cool my burning buttocks.

The next morning under the communal showers my battered backside with its five-bar gate and technicolour bruises was admired by one and all. I had survived my thrashing from The Gaffer, now we wondered which of us would be next.

For The gaffer of the Academy, Part 1, click here


Other school stories you might like.

Six of the best caning stories 1. The sixth-formers

Six of the best caning stories 6. Unfinished business

High school reunion


More stories from Charles Hamilton II are on the MMSA website

Charles Hamilton the Second

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