Six of the best

“If you can’t beat sense into a boy, you sometimes have to fuck sense into him.”

My name is David Kemp and I am fifteen years old, boarding at a public school in the middle of England. My parents live abroad, moving around, so for most of the year my home is school, and I have been going through a rebellious stage of misbehaviour. I am a bit short for my age, but well-built and athletic, with pectorals, deltoids and a six-pack, and a cock which is a shower. I play rugby at scrum half, I am in the gymnastics team, row, and bowl quite fast at cricket. I am also still very blond and blue-eyed, with a sallow, yellowish skin which takes a tan.

My latest misdemeanour had earned me six of the best, or so I thought. Six of the best means being caned on your bare arse, and whilst some of the schoolmasters tended to pull their punches a bit or even tried to give other punishments, my housemaster was a strict disciplinarian who enjoyed the sight of a trembling pair of boy’s buttocks, the whiter the better, and the swish of a cane, leaving a red weal on perfect skin, loving the sound of a boy in pain. The more the boy cried out, the better. I imagined that, as I was one of the cockiest boys in his house, he would put extra effort into those strokes to humiliate me. The problem was, I was quite turned on by the idea of the punishment, the ceremony, and the pain.

Caning was set for seven o’ clock in his study. On time, I arrived, and my housemaster was in his cloak and mortarboard, testing several canes.

“Drop our trousers and bend over the desk,” he ordered. I wanted now to run but did as I was told. I undid my belt, pulled down my trousers and underpants, and let them slide to the floor. My housemaster was not happy. He tapped my cheeks with a cane.

“You’ll need to take your trousers and underpants off and spread your legs a little,” he said. I obeyed, though I was nervous about what happened next. He was building up for a stroke which would split my arse in two. I took off my shoes.

“And the socks, whilst you’re there,” he said. I was now naked from me waist down. I leaned over the desk, aware that my arse was like a big practise target.

There was a knock on the door. A hushed conversation. I stayed where I was, focussed on my naked white arse, waiting for the sharp pain as the cane came down. My housemaster came back, and distracted me by stroking my buttocks with the cane.

Suddenly there were bodies everywhere. Two men held each arm whilst a third was ripping my pullover over my head. I went to cry out but a cloth gag was put over my mouth and tied tightly behind my head. I wriggled and writhed and struggled, but even though I was a strong lad I was nothing compared to a gang of adult men. My pullover came off, my shirt was unbuttoned and pulled away, and my arms were stretched and tied down. I was naked, vulnerable and at the mercy of half a dozen men.

“The boy loves this,” said one in a deep voice which I recognised as belonging to the maintenance man, a hairy brute with a big stomach. I felt his hand go down and feel my cock, which was as stiff as a poker. I wanted to cry and tell them to stop, but my body was letting me down. He wanked me with a big paw whilst a cold gooey substance, which turned out to be Vaseline, was rubbed into my hole. A huge thumb worked its way in, coating my virgin hole with jelly. My cock was getting stiffer, and I wanted the maintenance man to keep on rubbing my cock.

“Who’s first?” someone asked. It was the Geography teacher, a big, middle-aged man who had once been an Oxford rowing blue, and even as he pushed fifty looked good.

“Me,” said my housemaster, and I felt his cock breaking into me. He slid in slowly, causing me to gasp, stretching my sphincters. He began to ram his cock into me, harder and harder. His cock was average, but nice and hard, and I could feel it opening me up. At first it was uncomfortable, but this was a man who knew boy’s arses well, and I began to feel new, wonderful sensations, which ended a few minutes later as he shot spunk into me. He withdrew, wiped spunk on my cheeks, and invited the Geography teacher, who seemed to have a shorter, thicker cock, to fuck me. That was good to. Third up was a man I did not then know, but he seemed tall, with a long, slim cock which went further into me than the last two. A pair of strong arms, covered in tattoos, gripped my arms, but he was a man in a hurry. He came quickly, replaced by a man with exceptionally hairy arms whom I knew to be the PE teacher. He wasn’t the biggest, but he fucked like a bull, and wonderful sensations came back, so that I was close to coming when he roared and came in me. Next up was another man with tattooed forearms, very tanned, and short finger nails with dirt under them. He was the groundsman, and I remembered the time when I had seen him working with his shirt off, sweating in hot sun, muscles rippling under the skin. I was happy to be fucked by him and loved the way his cock worked my hole, but he too left me on the point of orgasm as he came. It was finally, when the maintenance man opened his overalls and pushed what felt to be the longest and thickest cock into me, that I came, just as he did, my mind a whirl of intense pleasure, gobbets of spunk spraying my housemaster’s desk and the carpet. The maintenance man withdrew. My hole felt sloppy, dripping with men’s cum and lubricant. My balls felt empty. My cock felt, for now, sated.

“Six of the best,” said my housemaster. “I will still have to cane you, of course, and the others will watch. Take your punishment, but there is more. You will have to stay here over half-term and help the maintenance man and the groundsman, both of whom have just fucked you. You will do exactly as they say.”

Yes please, I thought.

I took the six strokes of the cane. I was still held down, and I could see the groundsman, shirt off, holding one arm, and the maintenance man, overalls open to his bollocks, holding the other. I heard the swish of the cane and felt the first stroke cutting skin on my lilywhite arse. I grimaced under the gag. A few seconds later came the second, the third, the fourth, the fifth and finally the sixth strokes. I relaxed now and took in the intense, stinging pain. The other men dressed themselves and left the room as my housemaster cleaned up my arse and rubbed something soothing into the weals. In silence, I got dressed.

When I was ready, I looked at my housemaster.

“Dismissed,” he said.

Though it wasn’t over!