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Look Before You Leap

by Jason Land

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 27 Feb 2018

Look Before You Leap

An Erotic Short Story
Jason Land

It was with that horrible sinking feeling in his stomach and with his heart in his mouth that Willie Wagstaff: William Henry Alexander Wagstaff to give him his full name, made his way haltingly towards the Headmaster’s Study. It was now a quarter to eight in the evening; his appointment with the Headmaster was at eight and Willie did not want to be late. It was bad enough as it was to have to report to the Headmaster for what every boy knew would be a very painful meeting – for the boy that is – and to be late might lead to an increase in the already severe penalty which Willie knew he faced. Willie was now twelve years old and in his penultimate year as a pupil at the prestigious preparatory school for boys, Frogmore Court situated in the City of York. Next year would be his final year at Frogmore Court before he transferred to the upper public school, Frogmore Academy for Boys, located in the village of Frogmore a few miles from the city itself.

The Headmaster, Mr. Barton: Mr Edward Barton to be precise: a youngish man of some thirty five or so years was a strict disciplinarian and believed fervently in the beneficial effects of the rattan cane when applied vigorously to to the naked buttocks of recalcitrant boys, which was the fate Willie was dreading. The Headmaster, generally known as Basher Barton, was usually referred to by the boys as The Basher, an epithet which was largely justified by the way he dispensed his percussive largesse with a well-applied rattan cane on the naked bottom of any boy who appeared before him. Justice, if that is the correct word for what happened in The Basher’s study, was dispensed starting at eight o’clock each evening Monday-Friday, when boys who had received a punishment slip from one or other of the masters, assembled in the corridor outside the Headmaster’s study; there under the eagle eye of a final year, thirteen year old monitor they were marshalled into shape, youngest first and oldest last and awaited their turn to be called in to the face the Headmaster and meet their doom.

As Willie rounded the corner and entered what might be described as the home-stretch leading to the Headmaster’s door, he saw that on this particular evening there was only one other boy waiting there under the autocratic gaze of the duty monitor: a boy called Jeremy Hallam. Apart from keeping the boys in order whilst they waited in turn in the corridor to be called in to face the Headmaster, the monitor was also responsible for seeing that all the boys to be punished were correctly dressed for the occasion. Along with many other public schools, Frogmore had adopted what was referred to as the appropriate attire which was what a boy who was slated to have his backside beaten by his headmaster had to wear. The appropriate attire consisted of a pair of cotton gym-shorts and a gym-vest; and nothing more. The shorts were easily removed giving immediate access to a lad’s bottom, bum or arse, as it was variously referred to depending on who was speaking. Mr. Barton, the Headmaster at Frogmore Court, invariably referred that part of a boy’s anatomy on which he was to lavish his attention, as his bottom; but when he was applying his cane to the lads nakedness, he secretly thought of in terms of a well beaten arse as his objective; though – but but never voiced! Bum was what the lads at prep school called their backsides; whilst the upper school pupils normally preferred the more vulgar designation: arse.

As Willie arrived before the Headmaster’s door, Hallam, the monitor in charge of what might best be called the punishment platoon, quickly observed that Willie was not wearing the appropriate attire but had arrived wearing his normal school uniform. Like many a lad invested with the minimum authority, Hallam exercised his to the full, as he autocratically told Willie to go and get changed into his gym strip. Wagstaff, don’t you know anything about the way things are done in this place. When you are going to get you bum beaten by the Headmaster, you must wear the appropriate attire: your gym strip and nothing else. Now go and get changed immediately.

Willie was already very nervous about what was going to happen to him and very foolishly, without stopping to think dashed off down the corridor to return to his dormitory where he kept his clothes. Had he thought before setting of in a mad dash, he would have realised that there was plenty of time for him to get changed as it was only a quarter to eight. But he did not think; he panicked and in typical Willie fashion, leapt before he looked. Well as luck would have it – the bad variety alas – he ran slap into the Headmaster who was just on the way back to his study to deal with that evening’s miscreants. He attempted to explain to the Headmaster why he was running in the corridor; but to no avail.

Wagstaff, you are fully aware that running anywhere inside the school buildings is strictly forbidden and if a boy is caught breaking that rule, there are severe penalties incurred. Now go and get yourself changed into the appropriate attire for our meeting this evening and get back in line outside my study. You Wagstaff, have a lot to answer for this evening.

When Willie came back dressed in just his gym strip, he saw that another boy had joined the line waiting to see the Headmaster. Hallam, with a distinct lack of empathy, having observed what had happened in the corridor between Willie and the Headmaster said with considerable relish: I would hate to be in your shoes tonight Wagstaff. When he gets you in there, he is going to take the skin of your bum; he’s a real crack with the cane you know. He really beats the living daylights out of any boy who goes in there; it’s not at all the same as a swishing any more; it’s really hard-core stuff he dishes out. I can tell you Wagstaff, your bum is going to be so sore by the time he has finished with you; you won’t be able to sit down for days. Anyway Wagstaff, you’ve got lots of time to think about what he’s going to do to your bum; you’re the oldest of the three to be beateb tonight; so you’ll go in last; it’s youngest first, eldest last; so he’ll be nicely warmed up by the time he gets to you. The Schadenfreude: pleasure at the misfortunes of others, just dripped like venom from Hallam’s lips.

But how in the first place, did Willie Wagstaff find himself on the Headmaster’s list that evening anyway? Well Willie was note for his ability to disrupt any class with is inane but often amusing comments; and he never ever shut up; he was a constant chatterer, never paying attention to what the masters were saying; and so Willie Wagstaff’s bum and the light cane, wielded by a whole list of different teachers, were regular communicants. Willie probably had the doubtful distinction of possessing the most-often swished bum in the school. Willie was never ever rude to anyone and was liked by one and all – classmates and teachers included. And the extraordinary thing about Willie Wagstaff was that in spite of his apparent lack of attention during lessons, when exam time came, or in any impromptu test for that matter, he came top of the class in every subject except one: Latin; where he shared joint first place with another boy.

On the day where the action is now taking place, Willie finally got his comeuppance: had his Waterloo so to speak. The teacher in question, Mr Hawkins was, in general, a relatively unpopular figure with the boys and was in the middle of a rather boring lesson on Roman history. He had an aptitude for making his lessons boring and on top of that he had a very short fuse. So he was one of the teachers who regularly hauled away boys from his class to the library, where he made them drop their trousers and swished their bare bums for not paying attention. He had just uttered that trite phrase, known to all: Rome was not built in a day, when he noticed that Willie Wagstaff had apparently fallen asleep.

Wagstaff, wake up boy and pay attention to what I am saying.

Willie pulled himself to attention as he had actually been dosing as Mr Hawkins droned on: Sir, I was not asleep; really sir, I wasn’t; I was just thinking about what you were saying.

I see, Wagstaff; well stand up boy and share the profundity of our thoughts with the rest of us, if you please.

Willie heaved himself up and wondered what on earth to say. But before he opened his mouth, Mr. Hawkins said: Perhaps Wagstaff, you would begin by repeating the last thing I said to the class and then we will take it from there. We are all ears boy; the floor is yours.

Willie had only a hazy recollection of what he had just heard as he really had been on the verge of dropping off to sleep with the utter boredom of the lesson, when suddenly it came to him like a miracle out of his clouded recollection what Mr. Hawkins had just said; or rather what he thought Mr. Hawkins had just said. So he brightened up and said: Certainly sir; sir, what you just said was: Rome was built in a day.

A loud titter went around the class as the boys all realised the mistake the Willie had made. By then Willie also knew he had boobed; but in typical Wagstaffian style, in for a penny, in for a pound, he leapt before he looked and suddenly found himself in very deep water. Lord knows from where he got the inspiration for what he now said, but it had the whole class– convulsed with laughter. Mr Hawkins, however, was clearly – to use a well-know phrase – was not amused.

Willie ploughed on regardless: Well sir, you see I don’t think you were right sir, when you said that Rome was built in a day. No one could have done it in a day, sir. But you know sir, I heard, from a reliable source, that it was was built over the three day August Bank Holiday Weekend in BC 593.

Of course on hearing this piece of utter nonsense, the boys could not stop laughing. When the boys finally quietened down, Mr Hawkins, who as everyone could see was by now seething with anger, said very quietly but with considerable menace in his voice: Well after that astounding revelation, shall we continue with the lesson, And and you, Wagstaff, if you would kindly remain behind at the end of the lesson when we break for lunch; you had I have some very pressing business we need to transact before you go to lunch.

Willie thought immediately that he was in for another swishing, which frankly in view of his little piece of theatre, he had just enacted, he thoroughly deserved. But when the class was dismissed, Mr. Hawkins beckoned him to his desk and said: Wagstaff; I have had enough of your disruptive inanities in my class. I have swished you I don’t know how many times to no avail; you boy, are incorrigible; and so young man, I am going to send you to the Headmaster this evening and let him deal with you in a more thorough manner.


Willie’s heart missed a beat and then started pounding in his chest as he realised the implications of what he had just heard. He was being sent the Headmaster: to the dreaded Basher Barton for a proper beating with a senior cane that very evening. Willie felt a cold shiver of fear run through him; he had never before ever been sent to see The Basher, who had a formidable reputation with the cane, which he apparently did not spare on any lad’s bum who was sent to him for punishment. Willie had seen the damage done by The Basher’s cane on the bum of one of his dormitory mate’s; it was a mess of deep welts turning red-blue and looked incredibly painful; it was in a different world to the swishings which he had experienced to date in his school career. Willie stood there trying to apologise to Mr. Hawkins for what he had done; he even suggested that Mr. Hawkins swish him right now, before lunch. But it was a plea which fell on deaf ears as Mr. Hawkins opened his desk and took out the dreaded book of punishment slips.

Willie had hitherto never seen this book, which in many ways was like a cheque book; it contained a space for the name of the boy to be punished; a space for the reason for his punishment and, like a cheque book a space for a number; but this number was not a sum of money but the recommended number of strokes of the cane to be inflicted on the bare bottom of unfortunate bearer of the note. Mr. Hawkins assiduously filled out the slip in full, tore it out the book and handed it to Willie, who in horror saw that Mr. Hawkins had recommended six-plus cuts of the cane to the Headmaster. Willie now had to take this missive and deposit it in the punishment-note box outside the Headmaster’s study; and then at the appointed hour of eight that evening, along with other unfortunate recipients of similar notes, present himself wearing only the appropriate attire of gym shorts and vest and wait in the corridor under the watchful eye of the monitor, to be summoned to enter the study and meet his fate. And so that is how Willie Wagstaff, wearing just his gym strip, came to be standing in the corridor outside the Headmaster’s study that evening, waiting his turn to be called in to face the dreaded Basher.

The green light on the door flashed on and a buzzer sounded. The monitor, Jeremy Hallam, knocked on the door entered and announced the first victim of the evening. The poor lad entered trembling and the monitor withdrew, his job completed for the moment. Whether by design or by accident the door was left partly ajar so that the two waiting lads, Willie and his younger companion could more or less hear what was happening inside the room. There was first a muffled conversation followed by a pause; then a few minutes later the inimitable sound of a cane mating with a boy’s naked bum was clearly heard; to be followed a split second later by the first howl of pain from the recipient. There was then a pause of some ten seconds or so, followed by another crack of rattan again meeting bare skin; and even louder cry of appreciation was emitted by the recipient.

And so at that slow pace, the beating continued. Willie by now almost petrified with fear, counted no less than a than another eight cuts before a few minutes silence, broken only by the sobbing of the poor lad who had just been beaten. Finally the door opened and the lad in question, sobbing uncontrollably and rubbing his bum vigorously in a vain attempt to alleviate the extreme pain which he clearly felt, was shown out by the Basher himself and the door was again closed. Then followed a wait of at least five minutes, which seemed like a lifetime to the two lads still shivering with fear in the corridor. The nervous tension in both lads had more or less built up to breaking point before the door was again opened and the monitor, Jeremy Hallam, ushered in the other lad to meet his fate at the hands of The Basher

Finally some twenty minutes after the first of the three boys had entered the Headmaster’s study, Willie’s turn arrived; he was ushered in to face the Headmaster by Jeremy Hallam, who portentously said: Wagstaff to see you Headmaster. Hallam then left and this time closed the door properly behind himself, leaving Willie standing there shivering with fear, facing the formidable Basher.

Willie had never before been in the presence of his Headmaster; in fact, he had until now, never ever spoken to him; he knew him only by sight as a remote authoritarian figure with a formidably frightening reputation with the cane. However, Willie realised that he was now to see – and, in all probability, feel – for himself whether The Basher really lived up to his reputation. Willie quickly learned standing there, trembling like a leaf in front of The Basher sitting behind his huge desk, that his Headmaster knew much more about him then he did about the Headmaster.

Well Wagstaff, I have here your personal file and I have to tell you that in many ways it makes very sad reading. Your teachers all report that you are regularly a disruptive force in class and in spite of numerous swishing since the time you arrived her as a new boy several years ago, you have not found it in yourself to reform your ways and stop making inane comments during the lessons. However, on the positive side, you are a very bright boy; and I see that you have been regularly top your class since you first arrived here several years ago. So as you can see, Wagstaff, there are two sides to your character which seem to contradict one another; with the apparent lack of attention you apparently pay during class, one would expect you to be that the bottom of the class but the converse is true; so Wagstaff, academically speaking you appear to have a bright and successful future ahead of you.

Willie had listened intently to this discourse and when he heard what apparent amounted to praise of his academic achievements, he brightened up and momentarily thought that perhaps he was going to escape with just a verbal warning from his Headmaster and that he might emerge with his bum unscathed from this interview. Alas, as he now learned, nothing could have been further from the truth.

The question is, Wagstaff, what am I to do with you, one of our brightest boys ever, to make you see that you cannot go on as you have been doing in the past. Things have got to change; being top of your class is just not enough; you have to learn to behave correctly in the society in which you currently live. Mr. Hawkins, to whom I have spoken, tells me that your remarks today were the final straw for him; he felt that he could no long