The benefit a new headmaster brings

I was eighteen years old when I got my first and only school caning although I had been fantasying about a trip to the headmaster’s study for six-of-the-best since I was a small child. The problem I had was that my school was not what was generally known as a “caning school”, that is corporal punishment in all its forms although not banned was hardly ever used. Then, quite unexpectedly, our headmaster retired to be replaced by Mr Douglas-Pennant, a younger more aggressive model. Caning was back on the agenda.

A few weeks later, in the spring term I found myself alongside my pal Donald on the carpet in the headmaster’s study. I’d never been there before and it was actually much more modern than I had imagined with a light wood desk and matching bookcase, cupboards and chairs. Hanging from a hook on the wall was a standard school cane of the period; about three feet long with a curved handle and as thick as a pencil. Even from a distance I could see it was an awesome weapon. I think my face paled, certainly I was immediately aware the palms of my hands were sweating. I struggled to stop myself gaping at it.

Mr Douglas-Pennant was an “actions speak louder than words” type of man, he didn’t have much to say. We had been caught in town after the headmaster expressly said sixth-formers were required to stay on school premises all day even if they had no lessons timetabled.

We had no excuse. Mr Douglas-Pennant had only recently arrived at the school and he was keen to impress upon us all that his word was law. I had been banking on that. He couldn’t let us get away with disobeying his direct instructions. It would be a caning for certain. At last my fantasy would be fulfilled. I suppose it was a bit mean on Donald. It had been my idea to go into town and I was determined that I would be away long enough to missed by Mr O’Reilly, the head of sixth-form. My summons to the headmaster’s study would then be inevitable. I could have insisted to Donald that I went into town alone, but we were best friends and he knew as well as I what the penalty would be if we were found out.

I stared transfixed as the headmaster slipped off his black gown and hung it on a hook behind the door, then took off his charcoal-grey suit jacket and hung that up too. He walked towards the centre of the study to move a coffee table into the corner. Then he reached up and took the cane from the hook. He obviously meant business. He paced up and down the large open space in the centre of the study all the time telling us of his shock and horror at our violating his expressed instruction. As he spoke he flexed the cane between his hands the whole time. He really was a bit of a ham.

Donald’s head bowed lower and lower and he clasped his hands behind his back as though trying to protect his tight bottom.

“Take off your blazers, put them on that chair,” Mr Douglas-Pennant’s curt command set my heart racing. We stumbled with the buttons but eventually both of us managed to do it. Donald wore a crisp white shirt that hugged his well-developed chest. His pale-grey trousers were a bit tight and short in the leg and they showed off his tight backside perfectly. He was slim, almost to the point of being thin. He had medium length dark brown hair, just long enough to start looking untidy, with a few curls around the ends. His face was cute, for a boy anyway, and his most noticeable feature was long eyelashes, which many girls would kill for.

“Mitchell, go and face the door. Mowbray, come here!” That meant Donald was going to go first. I would be able to witness my pal’s beating before enduring (or did I mean enjoying) my own caning. Donald and I cast rueful glances at one another. Donald looked pale and forlorn as he moved to the centre of the room.

“Stand there!” Mr Douglas-Pennant theatrically pointed with the cane to a spot on the carpet. Donald swayed slightly, his hands clenched and held rigidly against his hips.

“Now… bend over.”

Those magic words quickened my heartbeat yet again.

Donald swallowed so hard it sounded like a gulp a cartoon character might make. Then without a murmur he bent gracefully forward with arms outstretched until with fingers straight and body straining his fingertips just touched his toes. His tight pale-grey trousers strained against his thighs and buttocks which were round and, in this bent-over position, jutting out.

I watched savouring every second as the headmaster positioned himself on the far side of the bending boy and planted his feet a little way apart for balance. I wished that I had a movie camera, I wanted to record every moment to play over and over again. Instead, I would have to try to memorise it.

I can still remember all these years later that Mr Douglas-Pennant gripped the cane just below the crooked-handle, then he wobbled it a few inches away from Donald’s twitching bottom. The headmaster reached out with the cane and placed it across the centre of Donald’s buttocks; he was making sure he was the correct distance from his target.

The tension was unbelievable, I could hardly breathe as I watched him lay the final foot of the cane right across the centre of my pal’s beautifully-rounded bottom. Donald flinched at the first touch of the rattan, knowing it to be only seconds away from causing him extreme pain. Mr Douglas-Pennant tapped the cane three… four… five times on the same spot. Donald’s fleshy bottom-cheeks trembled with each tap.

Mr Douglas-Pennant suddenly set his face into an expression of steely determination. He swept the cane well back. Donald’s buttocks tensed and tightened as he anticipated the stroke.

Then, swiftly SWISH! THWACK!

Donald let out a yell like a scalded cat, shot bolt upright, clasped both hands to the seat of his backside and rubbed like hell.

I saw the headmaster’s mouth open wide with what I took to be a mixture of anger and astonishment. A boy was not supposed to react like that. There was some kind of honour code that said the boy took his punishment “like a man”. The name of the game was that the fellow wielding the cane was the master and the boy was the subordinate. The boy’s job was to submissively offer up his bum to the master for chastisement. The master duly lashed six strokes (universally known as six-of-the-best) across his stretched backside. The boy was to make no fuss; no matter how much it hurt he was not to let on to the master that he was in agony. At the end there might be a gentlemanly handshake between the two and the boy would be dismissed.

Clearly, Donald had not read the script. He rubbed and he rubbed. “Stop that this instance,” Mr Douglas-Pennant growled in the way that headmasters did in those days. “Bend back over and if you get up again you’ll get extra strokes. Do you understand boy?” Sorrowfully, Donald said that he did and with some fortitude he resumed the position, fingers against toecaps.

I watched intrigued to find out how Donald would take the second stroke. Tap, tap, tap… SWISH! THWACK!

He squealed after the whippy rod tore into the underpart of his bottom. The headmaster’s threat seemed to have worked because, although his fingers left his toes and his knees sagged slightly, Donald more or less maintained his undignified, submissive position. Within seconds he had regained his posture, even though he was making high-pitched moaning sounds which aroused me considerably.

Tap, tap, tap… SWISH! THWACK!

Now, Donald shrieked and I watched with my tongue lolling out as my pal frantically rubbed his thighs together which sent his scorched rear into a very erotic side to side wriggle. His hands made white-knuckled fists then slowly straightened out again.

The next tap, tap, tap was quite low down his bottom cheeks, then the headmaster took a fairly substantial swing back and suddenly the tip of the cane vanished in a blur as it travelled at incredible speed with a whistling Swish! punctuated abruptly by the satisfying (to me!) Thwack! of rattan against sensitive teenage-flesh.

Donald yelled loudly and he started crying quite considerably. When he yelled he jerked his head back. He made deep muffled sobs as Mr Douglas-Pennant prepared for the next stroke.

This one was so low down that he was tapping to get his aim almost on the rounded crease where bottom met the thighs.

The headmaster gave a sharper warning tap then he swept the cane swiftly back and flicked it sharply. This firmer whack of the rattan on Donald’s softer flesh was very distinctive, and the stick bit into more sensitive skin. Donald jerked as if he had received an electric shock but he manged to stifle the yell he almost certainly wanted to unleash

“Just one more, boy,” the headmaster said, almost kindly.

“Ohh… yes… yes… sir!” It was almost as if Donald was begging him to give it to him. I supposed he wanted the ordeal to come to an end. It was another real stinger like number five had been. Donald writhed and squealed with pain. Mr Douglas-Pennant nodded with some satisfaction. ‘Stand up!’ he ordered. My pal stood up, wincing. He stood before us, tears streaming down his cheeks, hand clasped to his bottom.

“Stand by the door,” the headmaster intoned. “Mitchell, take his place.” That was my cue to prepare for the beating I had craved for so long.

Donald shuffled painfully over to the door and stood facing it then he put his hands behind him and massaged his flaming buttocks. He sobbed very quietly, uncomfortably shifting his weight from foot to foot as though he just didn’t know what to do with himself.

I moved forward. The Headmaster flexed his cane, “Bend over and touch your toes.” I swallowed hard. Before I had thought at this point in the proceedings I would unbutton my trousers, lower them to my shins and bend over, thereby offering the headmaster my bum wrapped in tight white cotton Y-fronts. It would be my way of saying, “Yes Sir. I have broken the rules, I deserve to be punished. I am ready to face the consequences. Beat me and beat me hard, I deserve it.”

It was a daft idea. Mr Douglas-Pennant would immediately smell a rat. A boy asking for punishment. A sixth-former, eighteen years old, begging for the cane on his underpants, that would be decidedly fishy.

Besides, I chickened out. I had witnessed Donald’s agony, I couldn’t be sure I could withstand the caning. In my fantasies I had only thought about how I would look spread-eagled across the headmaster’s desk or over the back of an armchair, or even touching toes. Now, I realised I had never actually considered how much pain a caning could inflict.

So, instead I bent forward from the waist and rested the palms of my hands on my knees.

“Further Mitchell,” the headmaster hissed. My buttock cheeks tingled as with a fast-beating heart I bent further forward to surrender my bottom even more prominently for punishment. I clenched my teeth so hard that my jaw started to ache. I could feel the sweat beading on my forehead. I stretched out my arms and touched the ends of my shoes with my fingertips. My legs were rigidly straight and I felt the smoothness of my tight trousers encase my meaty, rounded bottom.

I only had a view of my shoes and the floor beneath my feet but I could hear the headmaster moving around the study. I had witnessed Donald’s caning so I knew Mr Douglas-Pennant would be taking up his position to my left. He swished the cane through the air a few times as if he was trying to get my attention. He rested the cane about halfway down my bum and my bottom-cheeks tightened in reflex action but as the Head tap, tap, tapped the cane on the same spot the muscles relaxed again and my buttocks spread back to their full roundness.

Mr Douglas-Pennant drew back the cane then… SWISH! THWACK!

My body jerked slightly and I screwed my eyes tight shut, but I didn’t make a sound. It felt as though all the air had been forced from my lungs. It hurt like crazy, as if the headmaster had pressed a white hot wire cross my buttocks. A line of fire throbbed across my bottom.

Then, the cane was tapping a good two inches lower than the first stroke. I tensed myself as the Headmaster drew the whippy rattan cane backwards. I tensed and screwed my eyes shut again.

SWISH! THWACK! My body shuddered and I hissed so loudly I might have been mistaken for a steam engine settling down. To my own astonishment I still had not yapped. A bead of sweat formed on my brow and at the same time all saliva drained from my mouth.

Unexpectedly Mr Douglas-Pennant spoke. “You are taking this well, Mitchell. How many is that so far?” My head throbbed almost as much as my rear end and I didn’t immediately understand the question. Then I got it, “Two Sir,” I croaked.

Tap, tap, tap… SWISH! THWACK! This was a much harder whack and the sound of rattan sinking into my stretched bottom reverberated around the study and seemed to bounce off the walls. The pain was like an electric shock and this time I had to stifle the yelp my body demanded I make.

Absurdly, since my backside was blazing I noticed how the backs of my calves ached. The formal, traditional touch-your-toes position so beloved of headmasters when they caned schoolboys is very hard to maintain for any length of time. It would make more sense and not reduce the size of the target to allow boys to grab their ankles – isn’t that what the Americans meant when they said “assume the position”? I didn’t have much time to reflect on this because that damn cane was once more tap, tap, tapping against the fleshiest part of my bottom. I steeled myself for the inevitable wave of agony and it wasn’t long coming. SWISH! THWACK!

Now, I really wished I was grabbing my ankles, that would give me something to hold onto and help me fight the burning desire to shoot bolt upright and perform an Irish jig while simultaneously kneading my backside with the palms of my hands. Somehow, and don’t ask me how because I simply do not know, I resisted that urgent need. I understood why Donald had jumped up and rubbed furiously at his bottom.

Instead, I shifted my weight slightly from foot to foot, but still maintained my position. My face was now on fire and I bit deeply into my lower lip as that dreadful tap, tap, tap began again. He aimed this stroke at the lowest curve of my bum. Slowly the cane went back. SWISH! THWACK! It was a corker; harder than all the previous strokes that day. Was it my imagination, was he beating me more severely than he had Donald?

My head jerked back and now I was swaying and my knees buckled. The pain was excruciating as another fiery red band burned alongside the others. My whole bottom scorched, it was as if I had been forced to sit in  bucket of boiling water. I had started to straighten in a reflex action, but as I regained my composure after the searing sting of that stroke, I touched my toes once more and straightened my legs.

As the old musical entertainer nearly said, “You ain’t felt nothing yet!” because Mr Douglas-Pennant laid the cane right along the natural line between my thighs and my backside. This is the sensitive “sit spot” where the bum connects with the chair when you sit down. I flinched at the touch of the cane and my buttocks clenched, it was their natural reaction and a fruitless exercise to try to stop the agony they were suffering.

“Easy boy, easy,” the headmaster whispered as he sawed the cane across his intended target. Somehow I manged to control the muscles in my bottom and it relaxed a little. My fingers trembled as I pushed them harder into my shoes in my determination not to leap to my feet the moment that cane lashed into me. My knuckles were white.

The room suddenly fell very silent. All I could hear was my own laboured breathing, even Donald had stopped whimpering. The silence was soon disturbed by the now familiar tap, tap, tap. To prolong my agony the headmaster tapped away for a much longer time. Tap, tap, tap, tap, tap, tap, tap, tap. Eventually he swept back the cane dramatically. I drew my breath sharply and held it… but the swish didn’t come.

After what seemed like an age I turned my head slightly to see what he was up to. Then SWISH! TTTHHHWAAAAAACK!!

I was caught totally unawares by an incredibly hard stroke and my whole frame jerked forward, my  head shot back, my mouth opened wide and as I gasped for breath my his eyes opened wide with shock.

Nervously and rapidly I gulped in air to control a scream of agony which almost emerged but was stifled. Instead, deliberately and just retaining control, but with great feeling, I simply said ‘Ooooucchh!’ out loud.

“Stand up,” the headmaster grunted. I shot to my feet desperately wanting to rub at my scorched bum, but I decided that would wait for later. I wouldn’t give Mr Douglas-Pennant the satisfaction of knowing he had hurt me. “Take your blazers and go,” it seemed he couldn’t wait to get us out of his study.

As we left the bell for afternoon school rang and Donald hurried off to his chemistry class. I had history and hobbled down the passageway gently touching my backside, through the trousers and pants I could feel six thick lines. I spent an uncomfortable afternoon shifting about on the hard wooden chairs in my classes as the welts of the cane remained hot and sore, I squirmed a few times as every movement seemed to bring the strokes back to life, this was not lost on my fellow students and I got quite a number of knowing looks and smirks from the other lads in class.

When I arrived home later that afternoon my bum was still unbelievably sore and I went straight to my room and took my trousers and pants down. I couldn’t believe how red and striped my poor bottom was. I had horizontal stripes from the top of my crack to my upper thighs. It was a uniform colour throughout.

That night, I masturbated furiously as I wriggled my sore bottom against the bed sheets. In fact, writing this story has brought it all back. Where did I leave the Kleenex?

Picture credit: Sting Pictures

Other stories you might like

Pyjama bottoms down. Bend over (again)

Max of the ‘Champion’ 3. The headmaster

A maintenance spanking

More stories from Charles Hamilton II are on the MMSA website

Also writing school stories as Scholastic here

Charles Hamilton the Second

charleshamiltonthesecond@gmail.com