The Tyrant Headmaster 1. The boy at the bar

The man sat hiding behind his newspaper. His second large gin and tonic was nearly drained. Sitting at the bar, his back to the man, was the mysterious boy.

He wore a distinctive blue-and-white blazer. He was obviously a schoolboy; almost certainly a sixth-former. The man could just make out the outline of the boy’s school cap in his blazer pocket. In his hand the boy held a beer.

They were the only customers at the George. The boy was in energetic conversation with the barman, a youth probably no older than himself.

Who was this boy? The lighting in the bar was not good. From where he sat the man thought the boy might be a little Indian. Or did he have some Spanish in him? Italian perhaps? The boy’s jet black, almost blue, wavy hair was cut short exposing a longish slim neck. Was he an athlete? He seemed to have quite a muscular back.

Suddenly the boy stood up from his stool and leaned across the bar. What a terrific sight. His mid-grey school trousers clung to the outline of his legs which went all the way up to tight muscular buttocks. Oh yes, the man thought, very spankable.

The boy found the book of matches he was searching for and he reached into the inside pocket of his blazer and extracted a cigarette, put it between his lips and confidently lit it.

Dear God, the man thought, a child drinking and smoking, in broad daylight and in his school uniform. That was the problem with schoolchildren these days, he thought, they think they are grown up. They are not: they are children and they should be treated like such. If he had his way boys would wear short trousers until the day they left school, even if that was at eighteen. Short trousers reminded a boy he was exactly that: a child, not grown up. He should behave like a child; he should respect his elders and betters and submit at all times to authority.

The boy would look great in short trousers and knee socks. They would show off his legs and bottom to perfection.

The man’s thoughts were interrupted by the sound of giggling. The boy and the barman were sharing a joke. Were they talking about him? Had they spotted him ogling the boy’s bum?

He dived behind his newspaper and pretended to read, but he could not ignore what he had seen; this gorgeous sixth-form schoolboy in full school uniform drinking and smoking before his very eyes. And, the teenager was not even trying to hide. The man thought he would at least have taken his distinctive blazer off and put it in a bag.

He remembered a story he had seen in a newspaper the other month. One of the Sunday scandal sheets reported that a group of boys from a public school (that is an elite private boarding school) had sneaked off one evening and gone to a pub. They were spotted and reported to the headmaster, who proceeded to award the boys six-of-the -best with his whippy rattan cane. Most of the boys were eighteen years old, and one was nineteen, but that did not deter the headmaster from his duty.

The newspaper did not report whether the thrashing was given “trousers up” or “trousers down,” but the man expected that white cotton underpants, or even bare flesh, had been on show in the study that day.

The man hated staying in hotels on his own; it was boring and there was nothing to do except drink. He picked up his empty glass and took it to the bar.

“Same again, Sir?” The barman was rather delicious too. He wore black trousers with a high waistband and a sparkling red waistcoat; a combination that showed off his flat, firm buttocks.

The man had just completed a long tiresome railway journey and he had not eaten for several hours. The gin was beginning to go to his head.

He stood and waited for the barman to perform his drink mixing duties and tried not to eye-up the boy sitting beside him; but failed.

“Good afternoon, Sir,” the boy in the blue blazer was embarrassed by the attention he was getting and flushed a little.

The accent was pure “English received.” He sounded like a minor member of the British Royal Family.

The man stumbled on his reply. Close up he could see the boy’s sparkling dark brown eyes and his very-kissable full lips. His skin was a little olive in colour. Perhaps he was English, but from somewhere he had a little Mediterranean blood.

“Sir,” he called me “Sir,” the man thought. At least he was not some guttersnipe lout.

“Good afternoon,” he replied. The following silence was intense. Neither man nor boy knew what to do next.

The man filled in the silence. “That’s a very distinctive blazer you are wearing. Is it some kind of sporting club?”

The boy smiled. His olive face and dark brown eyes shone. His lips parted into a wide smile. “Oh, no. It’s St Septimus Independent Grammar School,” he said with great emphasis on the word “Independent.”

Ye Gods! The man thought. He is not even trying to hide where he is from.

The boy was very proud of his school. “It is the most prestigious school in the whole county,” he beamed.

The man’s jaw quite literally dropped. St Septimus Independent Grammar School. The most prestigious in the county.

“Well,” he retorted tartly, “If it is the most prestigious school, why are you besmirching its name by drinking and smoking in public while wearing its uniform.”

The boy bristled. He did not expect to be spoken to like this by a drunken old man.

“What are you doing here? Are you even old enough to drink alcohol?”

The boy and barman exchanged glances. The barman’s look said, “Leave it alone,” but the boy could not.

“Frankly, Sir,” he said with mock politeness. “I don’t think that has anything whatsoever to do with you. Now, why don’t you take your drink and return to your newspaper.”

“Nothing to do with me. Nothing to do with me,” the man thought it twice for emphasis. “We shall see about that young man.”

He picked up his gin and tonic and returned to his table. At that moment another young man, about the boy’s age, but not dressed in school uniform, arrived and the two of them fell into relaxed conversation.

Fuming, the man gulped on his drink and unsteadily returned to his newspaper. He spent the next few moments imagining the boy in his blue-and-white blazer and clinging trousers bent across any one of the many large padded leather armchairs in the bar. Once he had the boy over the high bar stool and then again he was bent across the bar itself. Finally, in his imagination, the boy was bent touching toes in the middle of the bar. In all his imaginations and whatever position the boy was in, there was always the man himself swishing a stout cane before flogging it into the boy’s stretched buttocks.

Two hours later the man sat on the edge of his bed. The hotel room was spinning a little. He had taken wine with his meal and now he told himself he should collapse into bed. He could not get that boy out of his head. Even now, he imagined the boy draped across the armchair in his room; only this time the boy’s trousers and underpants were at his ankles and the man was lashing the cane with such force that blood was seeping from the resulting wounds.

The man’s penis stiffened. He was not proud of this. When this happened in the past, he found a facecloth dampened with cold water placed in the strategic spot usually dealt with the swelling. This night, however, he would use hand relief.

Eventually, he rolled into bed. He needed a good night’s sleep. He needed to be fresh in the morning. Tomorrow was his first day as the new headmaster at St Septimus Independent Grammar School.

Episode two of The Tyrant Headmaster s here

Other stories you might like

Six of the best caning stories 6. Unfinished business

High school reunion

The cartoonist’s painful memory


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second


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