England 1970's
Although this story is fiction the events described in it are realistic. Perhaps it brings back some old memories..
I stood in front of the Headmaster scared _s_h_i_t_less. I had been caught tossing myself off in the lav and I knew that I was in real trouble. The prefect who had caught me stood at my side.
"What is it?" The Headmaster asked the prefect. The Headmaster had been relaxing in his study (sleeping probably) and was NOT happy to have been disturbed.
"I caught Williams masturbating in the lavatory sir." The prefect said. The Headmaster gave me his well-practiced look, designed to but the fear of God into me; and it did!
"Is this true Williams?" He asked me.
I started to blush and fixed my eyes on the floor.
"Yes sir." I mumbled.
"Speak up boy!" He shouted.
"Yes sir."
The Headmaster stood there looking at me.
"I will not tolerate such behaviour in this school Williams." He said. "On this occasion I will punish you. On the next occasion I will expel you. Is that understood?"
"Yes sir." I answered meekly.
My heart began to pound inside my chest. I had a very good idea of what my punishment would be.
The Headmaster turned to the prefect.
"Very well done." He told him. "This type of behaviour shows a negative selfish and unhealthy attitude to life and a total lack of respect for accepted morals. A boy who does not respect himself cannot respect the school of which he is part. Would you agree that a severe chastisement is called for?"
"Definitely sir." The prefect replied.
The Headmaster turned back to me.
"I'm going to cane your buttocks." He told me, turned around and walked over to the corner of the study where he kept his collection of canes. Returning with a heavy thick cane in his right hand, the Headmaster told me to take off my jacket and bend over the chair. I took off my jacket and stood in front of the chair. The Headmaster was standing behind me, the cane in his hand. The prefect was standing behind the Headmaster, grinning all over his face.
"Trousers and underpants down." He ordered.
Oh _s_h_i_t_. Not bare! I was really scared. I had never been caned bare before and I was sure that it was going to _f_u_c_k_ing hurt! More than once I had heard the screams of guys getting the cane trousers and pants down coming from the Headmaster's study and I had also seen the arses of some of my friends after they had taken a thrashing. There was always blood and their arses were covered with red welts and broken skin.
I undid the waistband of my grey trousers, unzipped my fly and pulled my trousers down to my knees to reveal my white Jockey Y-fronts (school rule: no coloured pants).
"Underpants down Williams" The Headmaster said.
I froze in fear and humiliation at bareing myself to the eyes of the Headmaster and the grinning prefect. I couldn't move my arms to drop my pants.
"Bare his buttocks" The Headmaster said to the prefect who came forward, grasped the waistband of my y-fronts in his fist and roughly pulled my pants down to join my trousers around my knees. I was bright red in total humiliation. My private parts were bared and everything was on show. I had been left with no modesty whatsoever.
"Bend him over"
The prefect pushed me down, positioned my hands on the arms of the armchair and lifted my shirt halfway up my back.
"Shall I hold him sir." The bastard asked.
"No. Not yet. They always get one chance to take it like a man." The Headmaster answered him.
I heard the sound of the cane swishing through the air. It cut deep into the tender white skin of my bare arse cheeks. I cried out in pain, my whole body jerked forwards and my _c_o_c_k_ and balls jumped up into the air. My buttocks were really stinging! I was in agony!
The Headmaster caned me a second time, even harder than before. I screamed. The pain from my ass was excruciating. I couldn't take it.
"Please stop sir." I begged.
The Headmaster administered the third stroke. My whole body jumped in the air. I turned round to face the Headmaster, grasping my wounded buttocks in my hands. "Please stop sir." I begged. "I can't take any more sir."
The Headmaster just looked at me.
"Turn round and bend over the chair." He said.
"No Sir. Please." I begged.
"I won't tell you again. " The Headmaster said. "Now bend over and stay bent over."
I realised that the Headmaster wasn't going to stop.
"Please sir. It hurts too much bare sir. Please let me take it on my trousers sir."
"If you don't bend back over immediately I'll get all of the prefects in here, you'll be stripped naked and held down for twelve strokes."
I had no choice but to obey him. I bent over and the fourth painful stroke was administered. I screamed and my arse jerked forwards. Those jerking movements were having an effect on my prick. Even though I was in agony beyond belief from my buttocks and really embarrassed at being made to take my pants down, my _c_o_c_k_ was growing in size! Thinking about my prick only made it grow more rapidly and by the time the fifth stroke landed I was more than semi-erect! There was nothing I could do to cover my _c_o_c_k_stand and I became even more embarrassed.
"Last stroke." The Headmaster said.
The cane landed on my bare ass cheeks with fantastic force. I screamed and jerked about in terrible agony. My _c_o_c_k_ stiffened up into a fully-fledged hard-on!
The punishment over, the Headmaster ordered me to stand up and face him. He took one look at my prick and told the prefect to make sure that I had an ice bath every night before bed for a week!
I was told to pull my trousers and pants up then thank the Headmaster for my punishment before leaving the study.
A week later I still had bloodstains on my pants.