Theodore's in Trouble!


by The Headmaster <Glenharris3000@lycos.com>

I hope that you enjoy this story. I do not support child abuse and these stories are intended solely as a support to roleplay between consenting adults.

If you are a naughty "schoolboy" who loves stern handling, or a strict headmaster who believes that it is infinitely better "to give than to receive", or if you simply enjoyed this story, please drop me an email. I would love to hear from you. I am based in Natal, South Africa.

A firm hand grabbed poor Theodore, dragging him firmly towards the bed.

"Well really, Theodore! You're in trouble again. I shall have to cane you! And most severely!".

A moment later, Theodore was flung across the bed, his short legs protruding across the edge.

"Bend over and touch your toes, boy!" came the strict instruction, as final adjustments were made to Theodore's position.

"And I'm going to take your shorts down and cane your bare bottom, too!".

Theodore's small blue and white striped shorts were roughly pulled off and dropped on the floor.

"There! Now I'm going to cane you, boy! You're in trouble again!".

A cane was quickly retrieved from under the bed.

"All boys should get the cane, Theodore! Regularly. And you're no exception".

As if to reinforce the point, the cane was flexed and swished through the air.

"I've got a nice whippy cane today, Theodore. Your bottom's going to be very sore by the time I'm finished with you!".

The cane was tapped against Theodore's bottom, almost toppling him off the bed.

"Oh no, you don't, Theodore! Don't you dare trying to run away! I'll give you an extra six of the best for that! Now you are going to get twelve cuts of the cane!".

Theodore's position readjusted, the cane was raised.

"And you needn't cry, boy! A caning will do you good. All boys need the cane!".

And so it began. A furious flurry of angry strokes rained down across Theodore, some of them not too well aimed, but all landing with good effect.

"How do you like that, Theodore?".

"Take that!".

"I hope that it hurts!".

"I that your bottom is sore!".

In a few moments the caning was over. The only sound that of heavy breathing after exertion and angry sobs.

The door opened and the cane was quickly dropped to the floor and kicked under the bed with a furtive movement.

A pretty little girl in blonde pigtails peaked around the door.

"Daddy's home" she said with a smug grin, "And he wants to talk to you. You're in trouble again!". Giggling, she pulled the door closed and ran down the corridor, her footsteps disappearing towards her room.

The boy stood in the middle of his bedroom. Still breathing heavily from his exertions, two tear-stained streaks running down his red cheeks.

He heard his father's footsteps on the stairs and wiped his face with his shirt. He gave his cane, a stick cut from a garden hedge that morning, another quick kick to send it further under the bed. He was still standing next to his bed, head bowed, when his father entered the room.

A heavy hand fell on the boy's shoulder.

"You and I are going to have another of our little chats in my study, boy. Come along.".

The boy was led out of the door and down the stairs, leaving Theodore Teddy Bear, spread eagled across the bed and a small pair of blue and white shorts on the floor beneath him.


More stories by The Headmaster