Tiny Spanking Story 2026 #23

Today was great, but exhausting. The first day of my period is always so uncomfortable and achey. I’m doing my best to stay on time, though!

o0o

When the door to the detention room opened, James startled and dropped the pencil he’d been chewing on, onto the desk.

He’d never been in trouble before and thus, had no idea what to expect. His Head of House, Mr. Sterling, stood in front of him, very well worn belt hanging limply from his right hand.

“Since this is the first time I’ve had to see you in detention, we’ll take care of this here. Stand next to your desk, Mr. Evans.”

James got to his feet and stood to the left of the desk, his bottom resting along its edge. Now, he was nervous. Perhaps if his bottom wasn’t visible, this wouldn’t happen?

“I suspect those cigarettes weren’t yours, Evans, and I find your stubborn loyalty admiral, but there are rules at this school and any boy caught with contraband is to get the belt alongside a week of detentions. Let’s make this unforgettable so perhaps you make a different choice in friends next time, hm?”

James barely breathed let alone responded.

“Over the desk then. Hands on the chair. If you move, we start over. A dozen should do the trick!”

James’ mouth fell open and he hesitated, before following Mr. Sterlings instructions. His short trousers pulled taught and rose up a few inches in such an awkward position and he kept shifting from foot to foot.

The first stroke of the tawse finally shocked him into sound and much to his dismay, he cried out – and never stopped. Mr. Sterling was thorough and fell easily into a rhythm, not giving James enough time to catch his breath between each stroke but pacing them so he felt each one before moving onto the next.

The last four angrily striped the backs of his thighs and would be visible under the hem of his shorts all week.

–

Running his hands over the bruising stripes later that evening, James looked in the mirror in awe. He was glad he’d finally found a way to get it before leaving school this year, without involving anyone else or making a fool of himself. He’d never even opened the pack of cigarettes after buying them. It was even easier than he thought to make sure Mr. Sterling saw him with them.

Because of his positive track record, it was automatically assumed he was staying silent out of loyalty, instead of risking self-incrimination and outing his plan of finally getting to feel the tawse before leaving.

o0o

The end. What a clever boy 🙂

—M

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