Rupert’s Punishment

Rupert was not a young man, consequently he had vivid recollections of being caned at school. Try as he might he had never been able to quite shake off the memory. Over the years it had developed almost into an obsession and slowly it changed from the judicial recollection it used to be to something more extreme which had puzzled him, but he had reached the stage at nearly 70 where he felt he needed to explore the feeling. He wasn’t convinced it was even something that would satisfy this craving, but he knew if he didn’t explore that he would always regret it.

These feelings are what had resulted in him finding himself standing outside Mistress Sofia’s door. The journey had taken him about two hours and to his mind he felt it was possibly worse than the impending punishment he would be receiving.

His mouth had been dry for the whole journey no matter how many sips of water he took. His stomach churned until it ached, surely nothing could be worse.

Rupert straightened his tie, lifting one foot he polished the toe on the back of his trousers, repeating the procedure with the other foot, just as he did all those years ago as a young boy. Then Rupert knocked on the door. “Enter” the voice was soft but stern. He opened the door and stepped into the room. Miss Sofia didn’t look up, she was busy writing in a notebook. It gave Rupert the chance to look around the room. His eyes fixed on the tubular container which was filled with every cane imaginable, but his eyes focused on the crook handle cane, which immediately took him back to the study he was caned in as a boy.

It was confirmed when he saw the 1960 school desk, with the ink well and the lift up lid. He knew this was where he would soon be bending over. He felt a s slight shiver go down his body. He focused his attention onto Mistress Sofia. Her legs were crossed, she wore beautiful patent leather shoes black shining with a slim heel and pointed toe, sheer stocking and a fitted black skirt. He loved the crisp white blouse she wore with the collar slightly turned up. Her hair was shoulder length silver grey showing the maturity he was desperately seeking.

She put down her pen and slowly closed her notebook. Raising her head Miss Sofia surveyed Rupert with the slightest hint of a smile. He shuffled from side to side.

“Well Rupert, i hear you have been making a nuisance of yourself. Your teacher has found it necessary to send you to see me. What have you got to say for yourself ?”

“I’m very sorry Miss, i know i have been disruptive in class. If you could let me off punishment i promise to improve my behaviour”

Mistress Sofia laughed softly “i dont think that would do at all Rupert. You have been sent to me for punishment and punishment you will get”

Miss Sofia put down her notebook, stood up, and advanced towards the array of canes. Her hand hovered over them for a few moments and then she slowly withdrew a beautiful crook handled dragon cane. Rupert watched as Miss slowly and lovingly stroked the cane and then without warning she lifted it high and brought it down through the air. The sound immediately transported Rupert back to his school days.

“Take off your jacket boy, position yourself at the desk then drop your trousers”

Rupert did as he was told “Now, bend over boy” He bent over and was surprised when Miss Sofia stood behind him and pulled down his boxers, he was expecting to be caned over them but knew it would be fruitless to object. Miss Sofia positioned herself and slowly drew back her arm. Rupert felt the first blow as the cane met it’s target with perfect precision. There was a sharp intake of breath as Rupert felt the first searing pain, it flashed through his mind what the hell was he doing here. The welt was immediate, it was beautifully positioned absolutely in the centre of his bottom. After that each stroke came in unison, there was no time between each stroke for Rupert to collect his thoughts. He wasn’t even aware of the amount of stroked administered.

Then it was over. Miss Sofia admired her handy work, Rupert’s bottom was beautifully marked, every welt evenly placed. She smiled then slowly gave his bottom a gentle caress. She pulled up his boxer shorts. “Now get dressed boy” Rupert obeyed then turned to Miss Sofia, he stood straight, hands by his sides and looked at her with new admiration in his eyes.

“Well boy, i hope you have learned your lession”

“Yes Miss”

“Then you may leave”

Rupert opened the door, stepped outside and shut the door. It was only then he realised he was smiling. He would definitely return.


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