"Oh, Thomas, what are you doing waiting outside the Head's Study?"
Thomas was 13 and very new to the school. With soft curly brown hair, blue eyes and a cherubic face, quite small for his age, he could definitely be described as a pretty little boy - and also a very naughty one.
James, who was speaking to him, was in the year above - and therefore not only experienced in the ways of the school, but also allowed to wear long trousers. Thomas wore brown cord shorts, white shirt and school tie, long khaki socks and brown sandals.
"I got caught stealing some money."
"Oh Thomas! You are in deep _s_h_i_t_. Do you know what happens here with that kind of offence. You are going to be so shamed up!"
At that moment, the green "Enter" light went on and Thomas entered his headmaster's study.
"Ah Thomas! I am afraid you are in very serious trouble. Do you know how we punish this level of misbehaviour?"
"Do I get the cane?"
"You certainly do."
"Right, where shall I bend over?"
"Ah Thomas! You do not just bend over."
"I don't?"
"You don't. You start by taking off your shorts."
"My shorts?" Thomas' jaw dropped.
"Yes, your shorts."
"What, here?"
"Yes."
"Now?"
"Yes."
"Oh. All right then."
Thomas took off his grey school shorts and put them on a chair.
"Do I bend over now?"
"No Thomas. You take off your shirt and tie."
"I.... oh. My shirt and tie, Sir."
"Your shirt and tie, Thomas."
"Here?"
"Here."
"Oh." Thomas undid his tie, unbuttoned his shirt and removed it. Now he was just in white cotton vest, white Y-Fronts, long socks and sandals. "Can I bend over now?"
"No Thomas." The Head pressed his intercom. "Miss Jennings, please bring all new boys to the hall for a special assembly."
"When do I bend over, Sir?" Thomas asked anxiously.
"Just go and stand in the corner..."
***
The ninety new boys were seated in the hall when the Head entered and walked onto the stage, holding a blushing Thomas, still in vest and pants, by the wrist.
"Boys - you will know Thomas here. He has been caught stealing. I expect he thought it was clever. He doesn't look very clever now, does he, in just his underpants? Stand further forward Thomas, so they can all see you."
Thomas stood forward. The Head stood behind him and pulled his underpants rapidly to his ankles. His vest was not long enough to conceal his small, circumcised dick. Thomas went bright red. The boys gasped and then giggled.
"Step out of your underpants and give them to me, Thomas."
Utterly humiliated, Thomas did as he was told.
"Now face the boys, take off your vest and give it to me."
Tears in his eyes, Thomas complied.
The Head moved his table toward the front of the stage. "Bend across the table with your legs apart and arms spread."
Thomas did this, presenting his pretty little bottom, with cheeks spread, for all to see.
The Head produced his cane and laid it on Thomas's buttocks. It felt cold and rough. He lifted the cane and brought it down hard. A vivid red line appeared across his buttocks.
The Head administered a second stroke. A new red line crossed the first.
He administered a third. Thomas cried out, "Ow!"
He administered a fourth. All of Thomas' little bottom was looking vividly red now. Tears were running down Thomas' face.
"Stand, apologise and shake my hand, Thomas."
Thomas stood, naked, and said "Sorry Sir", shaking the head's hand.
"Put your hands on your head and turn your bottom to the boys so that as they leave they can file past and see what happens when you do wrong."
The Head organised all the boys to file past, completing Thomas' humiliation.
***