This Will Teach You a Lesson

A new deputy headmaster gets advice from the headmaster. By a new writer to us, but a long standing writer in the world of CP

by Andy Nixon

“Ah, Harborn!” Dr Benjamin said, looking up from his desk and peering at me over his half spectacles. “Sorry to interrupt your free period. Do sit down. Settling in alright are we? Any problems? No? Good.”

I wasn’t really sure whether I was expected to answer, so I just smiled.

“First week, I know, but an ideal opportunity has cropped up, don’t you see. You see, there are certain duties, as my Deputy Headmaster, that I expect you to help out with. Tricky Johnny discipline! Not much corporal punishment at your old comprehensive, shouldn’t wonder. No? Thought not! More’s the pity, I say.”

The old boy had made his attitude towards strict discipline quite clear at the very first interview, and, I had to admit, I found it quite amazing at an all girls’ private school; and, not least, a little exciting.

“Miss Aldridge usually deals with the younger gals. Although she sends the juniors to me if it’s something really serious. But it’s the sixth formers that need a firmer hand. Short sharp shock from a daunting chap they respect brings ‘em up smart, and gives ‘em something to think about, don’t you know? Best thing’s learn from me. Get your confidence. Then you’re on your own. Any questions Harborn?”

“Err, that is, well, err, no, Dr Benjamin, I suppose not.” All this talk of girls’ punishment was flustering to say the very least.

“Good show old chap! Ideal opportunity this morning. This will teach you a lesson.”

‘A lesson I’ll never forget!’ I mused wryly, getting into the lingo already.

“Mmm. Thing is, give ‘em a good wigging on the day of capture, so to speak. Summon them to your study. Make them wait when they knock. Put on all your regalia; mortar board, gown; frightens the living daylights out of ‘em! Stand ‘em in front of your desk and pace around ‘em; give ‘em a real dressing down! Then look ‘em in the eye and pass sentence in a grave voice. And watch ‘em crumple. Works every time! Maybe show ‘em what they’re going to get, then tell ‘em to come back after assembly next morning. Let ‘em sweat overnight; most salutary! Two this morning. Wigged ‘em yesterday. A lower 6th form blackboard poet and a compulsive smoker from the Upper 6th.”

I crossed my legs and coughed uncomfortably.

“Should be a few butterflies in those two’s tummies just at this moment.”

There were one or two in mine!

“Skulking outside when you arrived, were they? Look a bit sheepish, did they, ey what? Good reason! Keep ‘em waiting, y’see.”

There had been two very shame-faced looking girls hanging about further down the corridor when I’d arrived for my unexpected early morning summons to the great man’s study, but I’d never imagined…

“One at a time, as it’s different misdeeds. Deal with ‘em together if there’s more than one being punished for the same thing. Caned the whole Upper 6th in the gym once,” the eccentric old disciplinarian murmured to himself as he strode to the door in almost military fashion, opening it and calling sternly: “Ashdown! IN!”

A somewhat pale-faced girl with shortish mousy-coloured hair shuffled into the spacious oak-panelled study, glanced at me with big brown fearful eyes, and then looked down at her feet. How daunting that study must have felt to the pretty lower sixth former just at that moment. She was very shapely under her neat school uniform, and her young breasts heaved up and down as she breathed deeply, clearly in a state of real agitation.

“Now Mr Harborn, may I introduce the suddenly-very-quiet, but usually somewhat-cheeky Katy Ashdown from 6b. And, Katy Ashdown from 6b, would you care to tell Mr Harborn what you did yesterday?”

The petite girl cleared her throat nervously and murmured: “Wrote a poem on the blackboard, sir.”

“And this poem; Shelley perhaps? Keats was it? Or Byron?”

“No, Headmaster,” she blushed.

“No Headmaster! Well I won’t ask you to repeat it, because I don’t want any such lascivious smut ever repeating again in this school. D’ya hear me girl?”

“No sir, I mean, yes sir.”

“And, to help you to remember not to repeat your dirty little ditty, I’m going to give you a swift, but painful reminder. Anything to say, Ashdown?”

“N-no, Headmaster.”

“Right! Cane, we said, didn’t we?” He muttered to himself, as he opened a tall cupboard. Behind the cupboard door was an impressive array of implements of corporal punishment; a myriad of crook-handled school canes of varying lengths and thicknesses, several leather straps, and a large well-worn plimsoll, which was propped up against the back wall of the cupboard.

“Mmm, 6b. Not exactly a junior any more, are we? Pick the implement to suit the crime, and the pupil, Mr Harborn. Something like this one should make a lasting impression on our blackboard poet, I think.” Dr Benjamin said, flexing a medium-length cane between his hands. It must have been about two and a half feet long, and it was about as thick as a pencil. “Not like your bamboo garden cane, y’see, all rigid. No, this is best quality rattan, ideal for the job. Swishier! So less effort for you, more sting for her.”

Katy Ashdown looked less than happy with the Head’s idle banter about her impending doom, and looked in horror as he swished the supple cane through the air, demonstrating its awesome flexibility.

“Right girl, slip off your blazer! Only get in the way Best off! Hang it behind the door, if you please, Ashdown.”

As the unfortunate 6th form girl reluctantly took off her maroon school blazer, piped with gold braid, and hung it where she had been instructed, the Head did the same with his jacket, and hung it over the back of his desk chair.

“Don’t want to restrict your swing, y’see, Mr Harborn. Roll up your right shirt sleeve too; show ‘em you mean business. You are right-handed I take it? Yes, thought so.”

With his right shirt sleeve rolled up, Dr Benjamin once again picked up the cane from his desk. Katy swallowed hard, her mouth obviously dry, standing there in her crisp white blouse; maroon and gold striped school tie; maroon skirt, fashionably above the knee; white knee socks, and shiny black heeled shoes; obviously feeling very vulnerable.

“Ceremony, y’see Harborn; all part of the punishment! Gives ‘em time to think about what’s to come. The sting in the tail comes soon enough, ey Ashdown? I don’t suppose you’re in any great hurry to bend, are you?”

The fidgeting girl blinked, but didn’t answer; she looked too nervous to speak just at that moment, and most of the Head’s questions didn’t seem to expect an answer anyway.

“Now, any questions so far, Mr Harborn?”

My pulse was racing at a new and exciting revelation that had come from his last diatribe. “Bend, Dr Benjamin? Do you always cane, err, that is, do you never? I mean I thought she’d have to hold out her…”

“Hand??!!” He boomed, finishing my question for me. “Oh no, no, no! Delicate devils, hands! Tricky business getting ‘em to hold still for an accurate stroke. They see the stick coming down, pull back and get it right across their fingers if they’re not careful. No! Gluteous Maximus! Made for the job! And the seniors are even more ‘Maximus’. No, very rarely cane hands. Can’t write then, y’see. No, no, no! Get to the bottom of the problem, if you get my meaning! Plenty to aim at, y’see. You can really put some weight behind it. Stings like stink of course, but no danger of real lasting damage.”

Poor Katy was even less reassured by this further information, and was blushing furiously at the size of her bottom being discussed so openly.

“Right, let’s get on with it. First-timer, ey Ashdown?”

“S-sir.?”

“First-timer in my study? Two or three encounters with Miss Aldridge’s slipper ,I understand. And it’s always cheek and impudence with you, isn’t it girl? First time for Jimmy Stick though?”

“Y-yes sir.”

“Well let’s make it your last! Two things about first-timers, Mr Harborn. Don’t be tempted to let ‘em off lightly, or they’ll be back again in no time. No deterrent, y’see. Make a girl’s first caning a crisp one, something that will make her not want a repeat performance, if you get my drift.”

Katy’s face was a picture. Any hope of leniency because she was a first-timer had just gone right out of the window.

“Second thing is, a first-timer will need something to bend over. I suggest a chair. Fetch that one from the corner, Ashdown! A high-backed one, y’see Harborn. Gets the target area at the right height, and gives ‘em something to cling on to when the old stick begins to bite. Bit of a shock for a gal, her first ever stroke of the cane. In the middle of the room, if you please Ashdown. Yes, there’s fine. Now stand behind it, behind the back girl! That’s right. Now, how many did we say? How many strokes, Ashdown?”

“Four, whispered the girl, in a tiny voice.

“What was that, girl?”

“Four – Four sir.”

“Yes, four good hard whacks to make you learn the error of your ways. Four strokes, Mr Harborn; a reasonable sentence as she is a first-timer. But, like I said, they must be crisp ones. No respect for going soft on ‘em! Alright, you stupid girl, let’s teach you a lesson you won’t forget in a hurry! Let’s see the target area. Lift up and gather…”

I could hardly believe my ears. Presumably Katy Ashdown couldn’t believe her ears either.

“Raise your skirt girl!!” He boomed. “To the waist. That’s it. Come along. Higher. Right.”

The lower sixth former reluctantly revealed a pair of luscious thighs, and even more reluctantly a pair of white cotton knickers, encasing an entrancingly and nicely rounded bottom.

“Tighten your knickers, Ashdown. Tug ‘em up nice and tight, that’s it! Got to get rid of any wrinkles and creases; get ‘em stretched good and tight for Jimmy Stick to do the best job. Regulations say corporal punishment should be over at least one layer of clothing for modesty, so we don’t cane on the bare, but thin knickers aren’t going to take away any of the sting, so long as they’re tight as a drum! If you’re in any doubt about thicker materials, just get ‘em to go change into athletic shorts; thin nylon, and usually a good snug fit, if you understand me. Check there’s no signs of cheating; padding, a strategically-placed extra pair can dramatically reduce the effect you’re trying to achieve. Once bent a 6th former over to find not two, but three pairs!! Soon stamped that little game out, mind you. Caned her over the thinnest of the three pairs; really made her jump, I did. Then had her up in front of the whole school next morning for a sixer with the tawse for cheating; danced a merry dance on top of her stripes, I’ll tell you! Put a message out to all the gals though. Don’t think anyone’s tried it since.”

Poor Katy Ashdown was fidgeting with her rolled up skirt anxiously, no doubt feeling very exposed. She must have wished he’d just get on with it.

“Right girl. Bend over! Right over the back of the chair. That’s it. Now reach down and hold on to the seat. Can you reach the far edge? Yes? Good! A perfect position, do you see, Mr Harborn.”

“Indeed.” I mumbled. How right he was! The pretty seventeen year old was almost up on tiptoes to reach the far edge of the seat, and her naughty bottom positively invited the firm smack of a hand, or a sharp stroke of the cane.

“The hips rest on the chair back, thus presenting the gluteal contours at a perfect height and angle for the visitation of the cane. Hold on tight, Miss Ashdown. No point pretending this won’t hurt because, I’m afraid, it will hurt a great deal! Mr Harborn, come round this side, then you can see better. There, how’s that?”

“Perfect!” I croaked, hoping I didn’t sound as eager as I felt about this much improved view of the proceedings.

“Now you stand, feet slightly apart, like so. Measure your distance so that the tip of the rattan will connect with the centre of the far, er, cheek. Get the maximum effect from the length of the cane. Then address the target, just like you would a golf ball. Do you play golf by the way?”

I didn’t bother answering as he seemed to be concentrating hard on tapping the cane several times right along the centre of the bending girl’s tightly-stretched white knickers. Katy shuddered visibly at the touch and her buttocks clenched involuntarily, changing their shape.

“Brace your legs back, Ashdown! Straighten those knees! You’re clenching! Relax them!” Dr Benjamin urged, patting her suddenly tightly clenched buttocks with the cane.

With some difficulty and obvious hesitation the girl managed to relax the muscles in her buttocks, and her whole bottom softened and rounded once again, so that it rippled slightly now when it was tapped.

“Now this will teach you a lesson for being a very naughty and vulgar young woman!”

Without turning his head from his interesting task, he also continued my lesson. “Now swing well back, like so, and…”

With a sharp wristy swish and a very meaty ‘THWACK!’ the Headmaster snapped the cane smartly down, bang on target. I was amazed how hard! I think Katy was too, because her reaction was instant. She yelped and looked back in horror at her punisher, her big eyes wide with pain and shock. It had obviously been a most telling stroke.

“Pause to give the pain time to build. There’s a second burn builds within a few seconds and gives ‘em hell where it does the most good! Never rush a caning. Now, did you see how I used the whole of my arm, not just the wrist?”

The Head seemed oblivious to the bending girl who was now sucking air between her teeth to control the obviously agonising smart of her first ever cane stroke.

“Now number two, a little lower. Try to aim accurately; like so.”

Another blinding flash and an equally sharp swish and ‘THWACK!’ of impact was quickly followed by a second shrill yelp, and some very distressed wriggling from Katy Ashdown, the impudent blackboard poet, who must have already been regretting her cheeky chalking.

“Pause again, do y’see, before lining up lower down still.”

The girl’s breath was coming short and fast, and her bottom was twitching as the Headmaster tapped the cane again on a new line, lower down the soft under-curves of her pretty bottom.

SWISH! THWACK!!!

“AAAHHHHH!!” Shrieked Katy, involuntarily kicking one leg up high in the air.

I had actually watched the thin white cotton material briefly and dramatically indent at the moment of impact, and then shudder and ripple as the soft flesh underneath sprang back into shape. The suffering girl sniffed and gulped loudly.

“Don’t let tears put you off your stride, Mr Harborn. It’s meant to hurt. Tears are a sign you are doing a good job. Have no sympathy. They get themselves into these scrapes. Good girls don’t get caned, do they Ashdown? Come along girl, straighten your knees. Straighten them! Unclench! Last one now. And I hope this will teach you a lesson in classroom behaviour!”

SWISH!   THWACK!!!

As promised, despite the lower sixth form girl’s obviously mounting distress, he held back nothing, and another scorching stroke zipped home, low down, just above the crease where her bottom ended and her shapely thighs started.

Katy loudly yelped again and straightened like a spring, clasping her hands to her now scalding rump. She looked up to heaven, her face a picture of agony, her mouth opening and closing like a goldfish, and tears now freely streaming down her hot, flushed cheeks from tightly screwed up eyes.

How I wished I could have seen the damage she was nursing beneath those thin pants, damage that was causing the cute girl such acute distress.

“That’s a lesson she’ll not forget in a hurry. Sitting down will be a forgotten luxury for the rest of the morning, and, hopefully, the awful memory of the last couple of minutes will deter the young madam from any further transgressions. Cane ‘em hard, Mr Harborn! Then give ‘em a few moments to compose themselves. Bit of a state, young Ashdown here. Busy yourself, move the chair, fill in the punishment register.”

Dr Benjamin took a large black book from his desk drawer and opened it. Katy’s blubbing had already subsided into sniffs and snuffles, and she had let her skirt drop back down into place. With her left hand, she was dabbing her eyes with a hanky, but her right hand was still firmly clamped to her wounded rear.

The Head wrote and spoke at the same time. “Katy Ashdown, 6b, Misuse of school property and gross vulgarity, Four strokes, Medium cane, Seat”

That done, he looked up at the miserable girl. “Anything to say for yourself Ashdown?”

“No sir.” Sniffed Katy, flicking her mousy hair back off her damp cheeks.

“Hurt, did it?”

“Y-yes sir. A lot.”

“Yes. So we’ll behave in future, won’t we?”

“Yes, sir.”

“Or it’ll be six of the best next time. Understand?”

“Yes sir.”

“Get to your lessons then. Tell your teacher why you’re late, and don’t let me hear any more complaints about you. Run along then.”

Katy tried to thank him, but her lip trembled as though she was about to cry again, so she quickly turned, walked stiffly and uncomfortably towards the door and picked up her blazer. The chastened lower sixth former’s face was blotchy red and tear-stained, her hair now untidy and, as she disappeared round the door, she was still nursing her right buttock through the seat of her maroon school skirt.

“See how they clutch the right one, Harborn! That’s where the tip strikes if you use the whole length of the cane. Sore as blazes!! Another triumph of swishy rattan over female strong will! Always leave the worst offender till last. Our Upper 6th form miscreant outside will have heard enough of what’s just gone on to remind her of just how painful a visit to my study can be, and it will have given her the jitters already. And the sight of Miss Ashdown’s emergence, with her transformation from a cool, if somewhat downcast, young lady to a snivelling, red-faced little girl will have done nothing to calm her nerves.”

In the excitement of Katy’s ‘transformation’, as Dr Benjamin so aptly called it, I had quite forgotten that there was to be an encore. What a start to the day!

“Let her wait a moment. Don’t put the cane away though. Not a first-timer, this one. Different tactics, do you see? Don’t want ‘em ever to get blasé about a visit for a punishment. Wouldn’t want ‘em telling the others it’s a piece of cake.”

With that the experienced disciplinarian strode back to the door, opened it and beckoned.

“Wellesley! IN!”

A few seconds later the unfortunate girl from the Upper 6th walked non-too cheerfully into the forbidding study, her high heels clicking against the highly polished parquet flooring. The girl was stunning. A statuesque blonde with large blue eyes, and a pouting, full-lipped mouth, which looked very sulky just at this moment. And with good cause.

“Mr Harborn, next may I introduce Lesley-Anne Wellesley. A bright and charming 6th former with an unfortunate wilful nature that would try the patience of a saint! I won’t even try to catalogue all her misdeeds, but today she is making a return visit to my office for smoking on school property, and whilst in uniform. And I don’t like return visits because it suggests that my previous ministrations failed as a deterrent. Smoking is a revolting and abhorrent habit, and I will not be defied! Caught red-handed by Miss Dewhurst, bold as brass, smoking in the 6th form common room! Only last term, Wellesley, that I caned you for the exact same thing! Don’t you recall, girl?”

“Yes sir.” She mumbled.

If it had been anything like he had just seen Katy Ashdown suffer, it would have been hard to forget.

“But you chose to defy me and smoke again.”

“I suppose so, sir.”

“So the punishment wasn’t severe enough for you, do I take it?”

“Yes sir, er, I mean, no sir. I mean…”

“How many last time?”

“Four, sir.”

“And how many did we say this time, Wellesley?” The Head enquired, picking up the cane from his desk, and flexing it menacingly.

“Six sir,” she muttered, swallowing and looking down.

“Six of the what?”

“Six of the best.” The beautiful blonde girl’s voice trailed away as she grudgingly uttered the words Dr Benjamin clearly wanted to hear.

“Six of the best girl! Six of the very best! I think this time we’d better teach you a lesson you’ll find much harder to forget. What do you say, Harborn?”

I didn’t know how to respond, so I simply nodded sagely and stammered: “Whatever you say, Headmaster.”

The girl glanced at me with a look of disdain, as though perhaps she had expected me to intervene on her behalf. Or perhaps she was just irritated that I was going to be witness to this more telling punishment. A punishment that she was clearly not looking forward to, despite her previous recalcitrant record.

Her attention was thankfully taken off me by Dr Benjamin moving across to the tall cupboard, and putting away the cane he had just used so efficiently on poor Katy Ashdown’s tender young bottom, and with such devastating effect. In its place he withdrew another one, a little thicker, and some six to eight inches longer.

“As I said, Mr Harborn, make the punishment fit the offence, and the offender. Wellesley here has chosen to ignore a previous chastisement, so we’re going to have to ‘hot things up a bit’. A sixer with this little beauty should see her sleeping face down tonight, and that might just make her buck up her ideas.”

The tall blonde was anxiously, and absent-mindedly, chewing her bottom lip as she eyed this new awesome looking instrument of senior schoolgirl corporal punishment. My eyes scanned the firm rounded swell at the back of her skirt, which suggested that there was a particularly inviting target area about to be revealed. Uncomfortably, but surreptitiously, I adjusted myself.

“Now Wellesley, to make your discomfort complete, I think we’ve progressed to toe-touchers.”

The poor girl licked her full lips nervously.

“Anything to say? No? Right, blazer off then.”

The stunning 6th former peeled off her blazer, just as Katy Ashdown had done only minutes earlier, but neatly draped it over a chair.

“Now stand just there,” the Head said, pointing to a spot in the middle of the floor with the vicious looking senior cane, and rolling his right shirt sleeve up a little further.

The atmosphere was electric as the gorgeous blonde slowly walked to the appointed place of execution, her young breast rising and falling nervously beneath her crisp white school blouse.

“Bend over!” Came the booming command.

Lesley-Anne didn’t hesitate, and bent at the waist, her long legs perfectly straight. She pressed her fingers down on to the toes of her black shoes, causing her short skirt to ride high up her firm and perfectly formed thighs, and the maroon material to stretch tightly over that tantalisingly rounded target.

“Skirt up, girl! Skirt up!” The Head snapped impatiently. “And pull up your knickers nice and tight. You know the form by now!”

Two reluctant and beautifully manicured hands reached back and flipped up the maroon skirt to reveal the most exquisite bottom imaginable, encased in a pair of satiny white briefs. The nervous hands then fumbled at the elasticated waist band and tugged up. The material stretched tight, moulding itself to those gorgeous contours like a second skin. As she tugged at both sides, the tiny briefs slid higher yet up her haunches, causing the chubby under cheeks to bounce free, quite bare, either side of the narrow white ‘V’. My heart pounded with anticipation. Lesley-Anne Wellesley then touched her toes once more.

All this time Dr Benjamin was flexing the cane between his hands and eyeing the target of his imminent ministrations. His eyes were bright as he watched the stunning blonde prepare herself, but then no man could fail to be moved by such a spectacle.

Without losing any professionalism, though, the Head then swished the longer and stiffer cane experimentally through the air a couple of times, with a scary whirring ‘swoosh’, then moved slowly round to the bending girl’s left, and planted his feet firmly apart.

“Trouble-maker, this one, Mr Harborn. Tough nut too. A history of slippering offences as a junior, third caning in just over a year, second one for smoking. Always check the girl’s record, and judge her punishment on what you discover. I’d like to think this will be Wellesley’s last caning, and, after six of the best with the senior cane, so will she. Make each visit less bearable than the last, y’see, till it’s done the trick. They have to learn. Legs straight, girl, brace ‘em back. Let’s see just how tough you are.”

With that the Head laid the cane across the scantily-clad bottom to measure his distance, tapping it a couple of times, before bringing his arm right back. Lesley-Anne visibly tensed. Her fingers pressed hard on to the ends of her toes, her legs pushed back defiantly. Like Katy, her buttocks clenched instinctively as she sensed the imminent descent of the cane, and she held her breath as the wicked length of rattan zipped speedily bottomwards, to land with an extremely solid and meaty ‘THWACK!

The blonde 6th former gasped loudly and buckled at the knee, half straightening to clasp panicky hands to her stricken rear.

“As you know, Wellesley, the measure of a caning is judged by the first stroke, and now you have my measure. I’ll thank you to remain bending. Touch your toes!!”

Lesley-Anne’s hands were clearly reluctant to leave her already badly stinging bottom exposed to a further onslaught, but slowly the 6th form beauty straightened her legs and reached down for her toes.

Dr Benjamin wasted no time. He briefly measured his next stroke with a well practised eye and swished the cane sharply down with a second equally ferocious ‘THWACK!!’, causing the well-bent bottom-flesh to judder visibly.

Her high heels left the floor momentarily as the wicked stroke brought her up on to her toes. Lesley-Anne’s head jerked back and she drew breath sharply as the biting smart sunk in. Her fingers left her toes and her fists clenched tight, but somehow she managed to remain bent over.

“Call the strokes, Wellesley!” The Head commanded.

“Two,” the unfortunate 6th former said in a tight voice, pressing her fingers firmly back on to the toes of her shiny shoes.

“Two what, girl?”

“Two, Sir,” she hissed, breathing hard through her nose.

The Headmaster reached out with the cane, arm straight, to measure his distance for his next line of attack. The wicked old sod was aiming very low this time, tapping the cane with an ominous warning ‘plack, plack’ sound on the bared under-cheeks that had wobbled free when the girl tightened up her knickers. Lesley-Anne also obviously realised the significance of this next line of fire, and cast a nervous glance back at her punisher. In those few instants I got an enchanting glimpse of her flushed face, and the twisted curl of her pretty mouth as she chewed her bottom lip again.

The cane snickered skywards. The eighteen year old mature schoolgirl screwed her eyes shut and put her head down, her delightful bottom tensing expectantly.

There was a sibilant ‘SWISH!’, and an even crisper ‘WHACK!!’ than any before, as the pliant rattan sharply connected with startling accuracy on the virtually bared lower reaches of Lesley-Anne’s firm young behind. Her perfectly-toned buttocks wobbled for an instant, then clenched violently, and the girl gasped a louder gasp than ever.

“Three,” she managed in a breathy squeak, her right hand flying back to nurse the furthest point, where the tip of the cane had wrapped itself around and bitten deep with an excruciating fury. That was certainly going to bruise.

Dr Benjamin turned to me at that point. I closed my mouth quickly. He was flushed and bright-eyed. Well, who wouldn’t be?

“Those low ones are the ones that make them prefer standing to sitting for a day or so, Harborn,” he announced, flexing the supple cane with great relish. “Hard chairs in the classrooms too. Very uncomfortable for a gal nursing even a couple of scorchers on the lower sitters.”

It was hard for me to concentrate on the finer points of caning technique with the distraction going on behind him. Lesley-Anne had taken the opportunity of this brief respite, and Dr Benjamin’s turned back, to straighten up a little and nurse her wounded rear-end. And, much to my disappointment, she tugged the edges of her knickers down to once again cover those lovely soft chubby under-cheeks.

The Headmaster noticed my averted gaze and quickly turned.

“Oh no you don’t, Wellesley! Tighten them up again!!”

There followed a half-hearted fumbling with the waist band of her knickers.

“Tighten them! Now girl, or I’ll do it myself!!”

Both her shaky hands then tugged at either side of the satiny briefs, causing the smooth material to glide up even higher than before, her ‘lower sitters’ bouncing free once more. And, yes! Testament to the cane’s most recent cruel visitation, a red angry-looking swollen double tramline etched across the soft pink smoothness.

The girl was breathing hard now, and licking her sexy lips, still in her half-bent position. Dr Benjamin tapped the white satin covered mounds briskly, causing them to twitch and wobble.

“Touch toes, girl!”

She didn’t have time to tense up this time, because no sooner than her fingers touched her toes, the cane ‘swooshed’ down and whacked full across the middle of her relaxed, unclenched buttocks, which impacted and bounced at the sharply punishing stroke.

The girl was taken completely unawares and squeaked and gasped. “Ooohh! Ohhhh!!” Desperately not wanting to give full vent to her true emotions. Her hand flew back with wide-eyed agony as she half-straightened yet again. There were several seconds of urgent gasping and panting before she managed to breathe.

“F-four, s-sir.”

The 6th former’s hands were trembling now as she forced herself back to the ‘bend over’ position. Her long blonde hair was quite tousled, and her breathing was short and fast as the cane lined up once more across her quivering buttocks. Fairly low, now partially uncovered, since the latest lingerie rearrangement.

SWISH!   THWACK!!!

An agonised grunt was forced from Lesley-Anne’s tight lips as the rattan exploded against already extremely tender bared flesh. Her knees bent, one high-heeled foot raising back. There was a soft groan as the awful pain mounted and sunk in.

“Five, sir,” she bravely sniffed as the red line slowly appeared emerging from behind the thin wispy knickers. Lesley-Anne sniffed again loudly and turned anxiously to see what the Headmaster was up to. Her eyes were clearly bright with tears. And no wonder. This was one hell of a caning. The old boy certainly knew what he was doing.

“I hope this is doing more to stop you smoking than your last dose of the cane my girl! Six of the best should prove more memorable. One more right where you sit will act as a final reminder,” he muttered, tapping the tender crease where her thighs ended and her bottom began. Completely bare flesh!!

“Bend further down, Wellesley! Straighten your knees girl.”

Lesley-Anne was now finding it much harder to get her fingers to her toes, in her present distraught state.

“Grasp your ankles. That’s it. Good.”

I gazed on, entranced. All the visible area of the stunning eighteen year old’s gorgeous and previously unblemished bottom was now suffused an angry blushing pink, decorated by two very clearly raised pairs of dark reddening, almost purple tramlines. It looked excruciatingly sore and swollen.

As the cane arced back for the last time, not only were the girl’s buttocks quivering, but her long shapely thighs twitched spasmodically too. The now desperate panting and sniffing from the well-bent 6th former suddenly stopped as she held her breath and tensed in anticipation of this awful climax.

Dr Benjamin’s fast rasping breathing was the only thing to be heard for a few seconds. It seemed like time had stopped. The striped young burning bottom twitched and clenched and unclenched feverishly.

Then the Head let rip. What a scorcher!! The supple rattan seemed to wrap itself momentarily around the lowest curves, exactly on target. It had the desired effect too. Instantaneously, the girl leapt upright, threw her head back, and yelped like a scalded cat. For an instant she froze, rigid, her hands clasped low down, grabbing the under-creases of her bum. She was almost bent backwards, her wet eyes screwed tightly shut, and her mouth twisting and contorting in sheer blazing agony. After a few moments she began to hop up and down on the spot, vigorously massaging her well-striped seat for all she was worth, her breasts bouncing intriguingly as she did so. Then the tears started to flow.

“S-six,” she sobbed jerkily. “Six sir, six, six, six!!” repeating it over and over in case anybody thought she might have some more to come.

“Mmm! Six of the best, Wellesley. Hot enough for you, was it?”

The tears were now running freely down her scarlet cheeks. Her maroon school skirt was still up around her waist, because her hands were still firmly clasped to her buttocks, preventing it from falling, giving me one last lingering look at the statuesque blonde beauty’s fabulously long and shapely legs.

Dr Benjamin was scarlet now too. So was I come to that. The Head dropped the cane down on his desk with a dramatic clatter.

“Miss Wellesley will not feel much like smoking again for quite some time. And she won’t feel much like sitting, I’ll wager, for quite some time either; ey, Harborn?!” He added, somewhat cruelly. “What do you say?”

“Errmm, no, Headmaster, she won’t feel much like sitting, I’m sure.”

“No. So, do you think we have taught her a lesson this morning?”

“Well it certainly was a, ermm, very good, er, very stiff, er, very sound punishment, headmaster.” It seemed inappropriate to use the word ‘stiff’ just at that moment.

“Have you anything to say for yourself, Wellesley?”

“No sir,” sniffled Lesley-Anne, looking down to avert his searching gaze. The girl wiped her eyes with the backs of her hands, letting her skirt drop back down.

“Tears Wellesley? You took your last whacking rather more easily, ey? A sixer with my number one cane is not so easy to grin and bear is it? And, if you ever feel like defying me again, just think what seven, eight, or even nine strokes would be like.”

The now quite bedraggled 6th former just sniffed and brushed away another tear with her left hand, nursing the burning throbbing right cheek of her shapely bottom with her right hand.

Dr Benjamin sat at his desk and picked up his pen and wrote in the punishment register, once again slowly speaking the words out loud.

“Lesley-Anne Wellesley, Upper 6a, Smoking in school, Second offence, Six strokes, Number one cane, Seat.”

All this time the pretty blonde gingerly rubbed the aforementioned seat of her skirt and sniffed, her breathing still laboured and fast.

“Think you’ll be able to help out with punishments, then, Harborn? Dish out the odd sore bottom to unruly miscreants like Miss Wellesley here?”

“Err, yes, of course headmaster, certainly.” I hoped I didn’t sound too keen.

“Got to practise your aim. Don’t want to put the cane in the same place twice. A bit too much that. Mind you, with the slipper or a tawse that’s the only way to generate a lot of heat back there, and a bit of respect; repeated application to the same spot. Twelve with the slipper, six each side in a small area can get quite a vocal reaction, ey Wellesley?”

Lesley-Anne sniffed once again, ignoring the Head’s rhetorical question. Just then there was a knock on the door and in walked Miss Dewhurst.

“Ah, Miss Dewhurst, I have dealt with our Upper 6th form smoker.”

“Had her just desserts, has she, Headmaster?” Crowed the middle-aged spinster.

Then she turned to Lesley-Anne with a smug grin. “Will we be standing up for our history lesson this afternoon, Wellesley?”

“Bitch!” Muttered the still suffering blonde.

“What was that girl?!” Boomed the Head.

“Nothing, sir.”

“I am neither deaf nor am I stupid Wellesley!! How dare you use language like that to a member of my staff?!” Dr Benjamin leapt to his feet and advanced on Lesley-Anne. “In all my years of teaching, I have never come across anything quite like it!! I will not cane you again girl, although you richly deserve it,  however your gross insolence cannot go unpunished. Mr Harborn, bring me a chair.”

I placed a straight-backed chair behind the Headmaster, the very same one that Katy Ashdown had been bending over just a short time ago. To my absolute astonishment, the great man plonked himself right down on it and commanded: “Over my knee, Wellesley!!” And dragged the tall girl, sprawling over his lap.

“No sir! NO!!” Pleaded the suddenly panic-stricken blonde, trying to wriggle free.

“You will either return to my study tomorrow morning for a further six of the best with the cane, Wellesley, or you will take a damned good spanking right now”

The pretty girl groaned and went limp. Slowly she stretched her long legs backwards, and placed her hands submissively on the floor, her already scorched rear now perched up high over the Head’s lap.

Wasting no time, he flipped back the short uniform skirt, once again revealing the girl’s small satin white knickers, still high up on her haunches, and those beautifully red-striped under-cheeks.

Briskly Dr Benjamin spanked Lesley-Anne, first one side and then the other. Each crisp smack elicited a yelp or a cry from the unfortunate 6th former. The visible flesh began to glow crimson as the spanks rained down, her bottom juddering and bouncing with every smack.

I was so close to the action this time I could actually see the imprints of the Head’s fingers glowing amidst the livid tracks of the cane.

Lesley-Anne bucked and squirmed, and eventually burst into tears. At that pivotal point the spanking abruptly stopped.

The whole thing had probably taken less than two minutes, but I estimated the old boy must have delivered upwards of sixty crisp smacks in that short time. The girl’s hands instinctively came back and cupped each buttock. What a contrast! The fairness of her hands against the burning red glow of the lower reaches of her bottom.

“Stand up,” croaked Dr Benjamin, rather thickly.

The sobbing 6th form schoolgirl stood, letting her skirt fall once more. Her face was a picture of misery and pain.

“Say you’re sorry to Miss Dewhurst!”

The poor girl couldn’t really speak for crying, but she managed to blurt out an apology of sorts. Miss Dewhurst looked smugger than ever. Dr Benjamin looked quite flustered, hot and bothered; after all, his hand had been connecting with a rather luscious and very hot eighteen year old female bottom. Hot in every sense of the word.

I was rendered speechless by the whole display. And I simply couldn’t believe that I was being offered the opportunity of doing the same.

Lesley-Anne soon stopped crying and we were all hastily dismissed. Of course, I just had to walk in the same direction as the well-punished blonde 6th former, so that I could follow and enjoy the last few moments, as she walked very stiffly and carefully down the corridor, her hands clasped tightly to the seat of her well-filled skirt. She wasn’t going to sit comfortably any time soon, I reckoned.

My first experience of administering corporal punishment came even sooner than I had dreamed, but that’s another story.

The End

© Andy Nixon 2017     View Andy’s Spanking Library page, click here


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