Weeping Willows Prep School for Boys 7 - the Deal 1


by Tristan <Yobo30@hotmail.com>

The boy and his teacher were alone in the classroom, the incriminating papers spread out on the teachers desk. The man sat, staring at the boy, but the sniffling 11 year old child could not meet his teachers gaze. He knew that he was in very serious trouble, and for once not even he could think of a way to get out of this predicament. Cavin was an intelligent little boy, but his behaviour was poor and marked with an element of dishonesty that his teacher and parents were regularly concerned about. An arrangement had been made whereby the teacher would send Cavin directly to the headmaster whenever the boy lied or cheated, to be caned. The headmaster would sign the note that the teacher had sent with Cavin after he had whipped the boy's bottom, then the same note would be sent home to Cavins father. Inevitably, Cavins dad would soundly belt his son's already bruised backside. It was hoped that this double hiding would cure the grade six boy of his bad habits.

This arrangement had worked well, but only twice. Cavin had made a plan of his own. The pretty blonde child had submitted to a good caning followed by a sound bare bottom thrashing from his father's belt only twice. He had quickly worked out that the best way to avoid bending over and paying a painful price for his dishonesty was to leave the classroom with the teachers note, wait for 20 minutes in the toilets, then forge the head master's signature and return to class. He was an accomplished liar therefore a good actor and had no trouble putting on a tearful expression, just like a boy who has just had a good hiding. He repeated the procedure at home, easily copying his father's signature so that his teacher would think that he had received his domestic thrashings as well. On at least 10 separate occasions Cavin had successfully pulled off this plan. For months his slim, pale young bottom had been free of whippings - although such punishments had been richly deserved!

But such dishonesty cannot go on forever. In casual conversation during a school rugby match, Cavins father had mentioned to his son's teacher how just the two hidings at the start of the year had seemed to have cured Cavin of his little problem. The teacher realised immediately what was going on, but said nothing. By his count, Cavin should have been thrashed at least a dozen times, and the punishments were doing little to sort the boy out. Now he knew why even the threat of a good caning and a belting at home didn't seem to worry the 11 year-old. He wasn't getting his hidings!

So it was at lunchtime the following Monday that the teacher took out all the notes that he had carefully filed and confronted the boy. Not even Cavin, with all his skills at evading punishment could deny the evidence.

"You know what this means," spoke the man, "don't you, Cavin?"

"Yes sir," the boy whispered, his fine blond hair damp with his nervousness, "I'll be expelled."

The teacher doubted if this was necessarily true, but it was definitely a likelihood, and it was a good thing that Cavin believed it. It was far more likely that the 11 year old would be whipped in assembly, like those two youngsters who had been involved with smoking had been, even although he was a day boy, not a boarder. He admired the child before him. Cavin was a tall boy for his age, a little thin, typical of a keen cross-country runner. He was by far the best runner in his age group in the school, and his physique was perfect for his choice of sport. The man let the boy stand there without saying anything. In all honesty, he did not know what to do with the lad. Despite all the trouble that Cavin gave him, he was genuinely fond of the boy. An old fashioned educator, the man believed that the boy should receive a hiding that he would never forget, but would the headmaster and boy's father do the right thing? The teacher himself was not officially allowed to administer corporal punishment - the school policy expressly prohibited any first or second year teachers to thrash the boys at school – it was felt that although Weeping Willows discipline policy was heavily based on corporal punishment, younger teachers needed some experience in the handling of the lads without immediate recourse to hidings. But the teacher had occasionally swatted a deserving backside, and even put a boy over his knee for a firm spanking a couple of times. In fact, he had even spanked Cavin once or twice. Boys in his class adored him, and almost willingly draped themselves over his knees rather than going to detention or being sent off to the headmaster. All these punishment were of course completely unofficial, and there was an unspoken pact among the grade six boys in the class that their teachers spankings were never spoken of to others. Particularly since all break time spankings were administered over underpants only!

Although Cavin knew that he was in a lot more trouble than just day to day fooling about, he decided to try and play everything down by provoking a spanking from sir. Without saying a word, the pre-teen dropped his shorts to his ankles and lowered himself across his teacher's knees. He had been in this position several times, and knew the procedure. He had made sure that his bottom was in the perfect place to be spanked by his favourite teachers big hand. The teacher was faced with a familiar sight. Cavins slim, rounded young bottom protected only by a pair of skimpy green underpants, looking a little threadbare. He had not expected Cavin to present himself for a spanking, although the boy fitted perfectly over his lap, and he loved the submissive theme of a good looking child almost on his teenage years bending himself over his knees. Instinctively, the man placed a hand on the boys perfectly presented bottom, enjoying the warmth and softness of the 11 year-olds rounded cheeks. His hand just about covered the entire surface area of his pupils backside!

"I'm afraid a simple spanking is not nearly sufficient punishment for your behaviour, young man!" the man announced, while gently kneading the child's bottom through his thin underpants.

"I know sir," Cavin answered, his voice slightly nasal from his position which put his head almost upside down, "but it's a start, sir. Please punish me yourself instead of telling the headmaster or my father."

The teacher carried on rubbing the young bottom so temptingly presented to him. He loved spanking his boys, and was aware that some of them, Cavin included, understood his little secret and played along. But he had always wanted to really thrash a pre-teen boys bottom, and now, just maybe, was his chance!

"How can a spanking from me be the start? What you need is a decent, bare bottom thrashing!"

"Youre right sir - but please, sir, you give it to me and keep it a secret! Please sir!"

The teacher gave the boy's bottom one last squeeze, and then he raised his hand and brought it down hard on his little target. It was one of the hardest spanks that he had ever given to a boy in his class, and Cavin yelped with the unexpected sting. His teacher had a very hard hand, and was a strong man.

The boy was well aware that spankings from his teacher stung, but had, like the rest of his classmates, always chosen the spankings rather than other punishments. Although they hurt, there was an element of illicit fun in the whole procedure of taking down school shorts and bending over his favourite teacher's knees for a spanking on his underpants rather than a more formal school punishment. By spanking the boys, completely contrary to the rules, the teacher was also seen as a bit naughty, just like the lads in the class. But this spank stung more than Cavin had expected! It was really sore!

Nine more times Cavin felt his teachers big hard hand crashing into his small soft bottom, but the boy kept his head down and his legs still. If he could get his teacher to give him a hiding but keep it a secret from the headmaster and particularly his father he would take a terrible thrashing willingly. It would be much better to have his bottom really pounded by this young teacher than have the humiliation and consequences of more official punishment. Besides, the 11 year old felt no guilt at lying to the headmaster and his dad – but was harboring some guilt about deceiving his teacher, so it was only right that his teacher should be the one punishing him!

The spanking stopped, and Cavin felt sirs hand once more rubbing his stinging bottom. The man couldnt resist rubbing his hand down the smooth, firmly muscled legs of the prone boy.

"Are you going to pull my underpants down and spank my bare bottom, sir?" enquired Cavin.

"Of course," it was an invitation that the man just had to take up, "but I still dont think just a hand spanking is enough punishment for you."

"I know sir. You will have to give me the belt, or even the cane. Or maybe both!" Cavin was desperate to show his teacher that he would take whatever punishment the man chose, anxious to show his complete submission, in exchange for amnesty from official sanction.

"The problem is, Cavin, that I cant do that at school. If I was found out, I would be in just as much trouble as you are!"

Cavin had the answer to that problem already worked out,

"Sir, you could come to my house – I live across the road from school! Rugby practice ends at 4, and my parents told me that they have a work thing on tonight, and will only be home after 9! Then you can give me a real hiding! You can even use my dads belt – but we dont have a cane, though."

The man said nothing – he was too busy enjoying slipping his fingers into the waist band of Cavins underpants, and slowly drawing the flimsy garment off the boys rounded little bottom and right down his legs to join his school shorts around his ankles. The preteens bum cheeks, although slim, were soft and perfectly curved. They had been startlingly white, but the spanking had already turned both buttocks into an angry pink, which contrasted nicely with the boys pale legs and lower back. Cavin was a very fair skinned lad, so there was not much of a tan line. Once again, he rubbed the 11 year olds small bottom, enjoying the direct contact with his hand on the naked flesh.

"Very well. You go straight home after rugby and have a shower – I dont want to thrash a stinky, sweaty boy! Ill come across to your house when Im finished here, and sort you out. Dont worry about a cane," the teacher added ominously, almost painfully squeezing the preteens very vulnerable feeling bare bum, "Ill handle that!"

As he had earlier, the teacher landed the first spank hard, and was rewarded for his effort by a surprised yelp from Cavin as the mans hard hand whacked onto his naked bottom. His head bobbed up with surprise, "Ow, sir! That hurt!"

"Of course it hurt!" the teacher had enjoyed giving his first bare bottom smack, "But remember, its only a warm up to the hiding youre getting later!"

Cavin put his head back down and gritted his teeth. It would not do to show weakness at this point. Although sirs hand spanking his bare bottom was far more painful than he had expected, he wanted to show his teacher that he could take his punishment – in the preteens mind, he was concerned that if he showed that he was in too much pain now, sir might decide to forget about their deal, and hand him over to the headmaster and then his father anyhow. The 11 year old was determined not to let that happen.

But he need not have worried. The teacher was in his element. He placed each hard spank carefully, making sure that he concentrated his efforts on the roundest, softest part of Cavins bare bottom – and he enjoyed the stifled yelps from the boy as he turned his sensitive little tail bright red. It was only the thought of thrashing Cavin "properly" with a belt and a cane that limited him to a dozen hefty swats.

The hand stopped falling on his stinging bottom, but Cavin remained as he was, draped half naked over his teachers lap. Instead of spanking him now, the boys teacher was gently rubbing his sore cheeks, and the young boy was enjoying the sensation. Had there been other boys his age in attendance, Cavin would have pretended to be horrified that sir was spending so much time feeling his bare bum – but since the two of them were alone, the preteen allowed himself to relax and enjoy the sensation. The sensation of being in such a submissive position and completely in the power of his teacher was deeply satisfying to the boy, and he started to actually look forward to having sir punish him in his home – he would be completely at sirs mercy, and Cavin found this strangely exciting!

"All right, up you get," the teacher ordered at last, lightly swatting the boys rather tender feeling bottom, "get dressed, and Ill see you later – then youll know what getting a hiding is really all about!"

Cavin slowly got off his teachers lap, and almost reluctantly pulled up his underpants and then his shorts. As he left, he glanced back at sir, rubbing his bottom with both hands, rather more theatrically than necessary. The grin on his face was cheeky, typical of the boy,

"Yes sir, Ill be ready sir!"

And then he left, off to play with his friends. But both man and boy knew that Cavin would be keeping his spanking, and the hiding to come, as a very special secret.

All through that afternoons lessons man and boy didnt meet each others eyes – the teacher taught his lessons as normal, but the boy was uncharacteristically quiet. He was on one hand excited by the hiding to come and the whole concept of being completely at the mercy of sir later, while on the other hand he was afraid. The bare bottom spanking at lunch had really stung – more than he had expected, and the child was concerned that he would not be able to maintain his dignity when sir thrashed him with the strap – and then, if sir managed to get one, a cane. Little did the sixth grader know that his dignity would mean nothing soon, and his teacher was determined to really break through his attitude, and enjoy doing it!

At rugby practice later on that afternoon, Cavin almost forgot about the coming session with his teacher – it was only when glancing across the field and spotting the man coaching a younger team that the 11 year olds heart felt like it stopped momentarily, and he felt the goose bumps of anticipation all over his body. The teacher was highly aware of Cavin in the next field, and every time the boy bent down to scrum (he was a flanker), he smiled to himself, admiring the childs rounded young bottom, protected by his dark blue shorts – shorts that would be out of sight in just an hour or so.

Rugby came to an end, and Cavin gathered his things. As he passed his teacher he once again smiled mischievously, rubbing his bottom, and then headed for home. The teacher himself headed for the staff changing room, and had a long, leisurely shower. He would make Cavin wait. After all, according to the boy, they had all evening! After he was once again dressed, the man headed for the main administration block of the school. He had to procure a cane, and had already determined that he would help himself to one from the basket that was always on display in the deputy headmasters office. The man had several, and wouldnt notice one missing. But as he approached the office, to his dismay, the door was closed, indicating that the man was still in, and there was a rather miserable looking boy standing, nose to the wall. He recognized the boy as Matthew, a pleasant, if rather silly 13 year old grade seven boarder. Matthew was a lad often in trouble for minor breaches of school rules, and it was not the first time that the teacher had seen the boy waiting for the headmaster or his deputy to warm up his bottom, but this was very inconvenient. He tried to ignore the boy and walk past him to the staff common room, but Matthew greeted him politely as he passed – the preteen must have heard him walk by, as he didnt move his nose from its position, pressing on the wall,

"Good afternoon, sir,"

"Good afternoon, Matthew," the man sighed, then to be polite to the obviously nervous boy, "why are you waiting for the deputy headmaster, young man?"

"I was towel flicking, sir." Towel flicking in the change rooms after rugby was a common crime among the boys, and they had just recently been reminded that it was an activity strictly banned. The rationale behind the ban was that the edge of an over enthusiastically flicked towel could miss its intended target (the bare, wet bottom of another boy coming out of the showers), and take out an eye. Matthew was a skinny, tall boy – even thinner and slightly taller than Cavin, with golden brown hair. His young backside would without doubt be the target of the deputy headmasters cane within the next few minutes. The teacher just hoped it would be done quickly, so he could sneak in there and get a cane for himself!

Just as he turned from Matthew to resume his walk to the staff common room, the door opened, and the deputy headmaster emerged,

"Ah, Mr Wood," the great man greeted him, ignoring the nervous 13 year old standing next to the door, "I wonder if you have a minute?"

The teacher, of course, would never refuse a discussion with his boss, turned politely,

"Of course, sir. What can I do for you?"

"A rather unusual request, Im afraid. I need to dash off, and young Matthew here needs a hiding. Would you mind doing the honours? An appropriate cane is already on my desk."

"Um, yes, Id be delighted, I mean, certainly sir," the young teacher couldnt believe his luck – hed get to practice before he thrashed Cavin, "but Ive never caned a boy before!"

"Nothing to it," the deputy head was already disappearing down the corridor, "hes been towel flicking – again. Give him one on his shorts, two on his underpants and three on his bare backside. That ought to sort him out. Oh, and Wood – hit him hard!"

Then the deputy headmaster was gone, leaving the young teacher standing with a rather tearful little boy. Matthew was a veteran to hidings, but had only ever had one stroke on his bare bottom before. This was to be a terrible hiding – and Mr Wood looked far stronger than the deputy. He would hit very hard indeed!

"Well, in you go then," Mr Wood had recovered his composure, and ushered the very nervous 13 year old into the office, closing the door firmly behind him.

Matthew walked straight to the centre of the room, and stood, head down, hands clasped behind his back. This was the way that boys reported for the cane from the deputy head, and the preteen instinctively presented himself as he was accustomed. The teacher crossed to the deputy heads desk, and, sure enough, lying on the blotter was a cane. Made of the finest rattan, just short of three feet long, curved handle. A simple, effective junior cane, just like all the others stacked in the basket by the door. Perfect for the thrashing of a mischievous 13 year olds bottom – and of course a dishonest 11 year olds backside too! Things couldnt have worked out better!

"Right, Matthew," Mr Wood picked up the cane and flexed it, then swished it through the air to get the feel of the light stick, "bend over – like you would normally do in here!"

Mathew turned around to face the back wall of the office, and, with the natural movement borne from lots of practice, bent over. He kept his feet well apart – nearly half a meter, as the deputy head always insisted, grabbed his ankles and straightened his knees. The boy made sure that he kept his head down, eyes closed and bottom well up. He had resigned himself to his fate – Mr Wood would follow the deputy headmasters orders, and there would be no discussion entered into.

This was the first time that the teacher had had a boy presenting himself like this for punishment. He had always just spanked the boys over his knees, so this was a treat. The formality of the whole scene was very exciting to him. Slowly, he crossed the room to stand in position to the side of the bending boy, and tapped the tip of the cane gently on the tightly bent young bottom before him. Even through is school shorts and underpants, it was clear that although Matthew was a thin boy, his buttocks were beautifully rounded, their shape emphasized by his tight position. Concerned about his aim, he pulled the cane back, and cracked the stick across his young target, the crack of the lash loud in the big room.

Matthew didnt move. His fears of Mr Wood caning him much harder than the deputy head had been unfounded – the stroke had stung, but not nearly as much as he was used to in this office. The boy had to decide quickly what to do. He could pretend that the hiding was hurting, and get away with a fairly mild punishment, or he could inform the teacher that he had to hit much harder. The former was the obvious choice – except for one thing. Once before Matthew had been caned by someone else on the deputy headmasters orders, and the following day, the deputy had called the boy in to inspect the marks on his bottom to see that the proper job had been done. If the deputy did that again, Matthew would have to repeat the hiding, and it would no doubt be much worse – maybe even all six on his bare bottom! And he would be indirectly responsible for getting Mr Wood, probably the most popular teacher in the school, into trouble. So he did the brave thing,

"Sir?" he didnt move, hoping that Mr Wood would appreciate his words, "You must hit me much harder than that. The deputy head might check my bottom tomorrow, and if I dont have six good welts, Ill get a much worse hiding."

The teacher was more than a little surprised at the boys words, but understood at once the predicament that the bending boy had been in. When Matthew had been in his class the previous year, he had put the slim lad over his knee only once for a firm spanking, and had been impressed by the stoic way in which the preteen had taken his punishment. Unlike many of the boys, Matthew had made none of the silly comments and play acting scenes that so many others made, taking his whacks in the manner of a boy who completely accepts the decisions of his elders – if he was to be spanked, he would take his spanking seriously. He had just gone up even further in the teachers estimation. The silliness that was usually associated with the boy was gone now that he was getting a hiding.

"Thank you for telling me, Matthew. I shall start again."

Confident now in his aim and technique, Mr Wood blazed the cane across the 13 year olds bottom, and for a moment Matthew regretted the decision to ask the teacher to hit him harder. It hurt! Sir could really cane hard! Not quiet as hard as the headmaster – Matthew had knelt on those back to back chairs enough times to know that the head was without equal when it came to caning, but Mr Wood certainly caned harder than the deputy!

"Okay, Matthew," the teacher had enjoyed that, especially the yelp of the bending boy, and the way in which his body had jerked as the cane cracked across his tightly bent backside, "stand up and lower your shorts, then bend over again."

Quickly, Matthew stood, gave his bottom a quick rub, then unclipped his shorts. As he lowered them down to his ankles, the preteen glanced behind him at his punisher. Mr Wood was flexing the cane, a faint grin on his face. Nothing had changed – the boy remembered how obviously the man had enjoyed spanking the boys in his class last year – and now here was Matthew, his first ever cane victim. More slowly now, the grade seven boy bent over again, presenting a much more exposed feeling bottom to the cane wielding man behind him. He felt Mr Wood lift his shirt up his back, clear of the target area, and then the cane once again tapping his bottom.

The teacher was enjoying himself immensely. He remembered Matthews underpants clad bottom from the spanking he had given the boy, but it had grown slightly. In this tightly bent position, the lads slim, round cheeks were clearly outlined in his thin, light blue underpants. He caned the boy hard again, instinctively flicking his wrist as the stick got to its target, then following the stroke through. The boy sobbed out loud, the pain excruciating as the stick burnt across his thinly protected buttocks. The sound of the cane snapping across the boys upraised bottom was intoxicating, and from Mathews reaction, the teacher knew that he was getting it right this time.

Matthew was in agony. Again, the cane tore into his young bottom, and the boy cursed himself for encouraging Mr Wood to cane harder. He should have taken a chance and said nothing. This was almost as bad as the headmaster himself!

"Stand up and take down your underpants," the teachers voice was shaky with excitement. This was great fun.

"Please sir," Matthew, like most Weeping Willows boys, had enough experience with hidings to hold back the tears, but he was struggling, "may I give my bottom a quick rub?"

Mr Wood was uncertain of the procedure – but he grunted his approval. Matthew surprised him by quickly slipping his underpants down to his ankles, and only then grasping his slim round bottom cheeks, massaging the naked flesh firmly to try an rub some of the sting out, twisting his body. Matthew seemed not to mind that the teacher got a full view of his privates as he squirmed. The man noted that although the 13 year olds privates were undoubtedly bigger than the equipment that he had glimpsed when spanking Cavin, the child was still completely hairless.

"Alright, bend over," it was time to finish off this thrashing so that he could get to Cavin. Reluctantly, Matthew complied, releasing his burning cheeks and slowly bending back into position. Again, the 13 year old surprised the teacher by flicking his own shirt right up his back as he bent, giving the man an unhindered target area. Looking at the tightly bent boy, now naked from the top of his socks to the middle of his back, Mr Wood could clearly see that Matthew, although tall and slender, was still certainly prepubescent. The stripes on the boys bottom looked painful, but he felt no mercy. The welts would heal, and he intended to paint another three good ones on those lovely round little cheeks too!

Matthew closed his eyes as he felt the cane rubbing lightly on his now naked, and very vulnerable feeling sore bottom. Sometime having to bare ones bottom half way through a hiding was almost worse than getting the whole thrashing bare. The boy knew that although his bum was absolutely alight, now that he was to be caned on his totally unprotected young buttocks, the pain could only get worse. And there was no doubt about it – Mr Wood was quickly gaining in confidence, and each stroke was getting more and more expertly laid on. He was not disappointed. The cane lashed across his tail, burning a stripe of sheer, pure fire into the preteens bottom. The child squealed with the intensity of it, and despite himself, Matthew felt a tear escape his tightly closed eye, running down his face.

Mr Wood was indeed getting his confidence. Many teachers find wielding the cane for the first time somewhat intimidating – it is an implement that takes some practice to apply to a boys bottom with accuracy, especially when hitting hard. Matthews naked hindquarters were not a particularly big target, but the man had a good eye, and thrashed the 13 year olds bottom like an expert. The sob from the boy as he blazed the second bare bottom lash down showed the young teacher that he was indeed getting this right. Never before had he made a boy cry from a spanking, so the cane was effective. He put a special effort into the last lash, sad that the hiding was coming to an end, but looking forward to getting across to dealing with Cavin. The 11 year old was going to suffer – that was for sure.

Matthew remained bending over, throbbing, striped bottom on display, while Mr Wood admired the results of his efforts. The boys white tail made the six raised welts stand out beautifully, and it would be clear to an observer that the boys tail had indeed been well thrashed.

And there was an observer. Cavin had undressed as soon as he had arrived home, and had a leisurely shower. Then, with just a towel around his shoulders, the young boy had gone into his own bedroom. He had an unobstructed view of the school across the road, and he glanced, more out of habit than anything else, out of his window as he passed it. The boys bedroom was on the second floor of the house, and he had looked down, a little surprised to see right through the window of the deputy heads office. Usually, the window was covered with slatted blinds, but for some reason, the blinds had been left open. The boy had been just in time to see another lad – he had identified Matthew from the 13 year olds slim physique, release his bare bottom and bend over. Then, to Cavins amazement, Mr Wood had stepped up to the bending boy and slowly, methodically, caned Matthew three times, and very hard, by the looks of it! Cavin had grabbed a set of binoculars, and for a few seconds had been able to examine the very battered looking bottom of the older boy. He gulped – his voyeuristic excitement forgotten as he remembered that his teacher would be crossing the road shortly to deal with him! He put down the binoculars and absently gave is own still bare bottom a rub. This would be a very painful session indeed!

The teacher finally allowed Matthew to stand, and, without making any effort to pull up his underpants and shorts, the boy had turned and held out his hand to the man,

"Thank you for giving me a hiding, sir," the 13 year old had recited automatically, his face wet with his tears, then, with a faint grin, "youre a really good caner!"

That, coming from a Weeping Willows boy, was a great compliment indeed, and the teacher recognized it as such,

"Thank you, Matthew," the teacher had returned the young boys firm handshake, looking down and smiling broadly into the wide blue eyes of the child, "I always do my best to do a good job! Now get dressed an off you go."

Matthew had only then given his bottom a firm rub, all the while grinning at the teacher while the tears dried on his face. The punishment was over, he had managed to get through it, and his friendly, mischievous nature returned. Of course, his thrashed bottom still throbbed like crazy, but when the boy left the room, he was still grinning, even although he had both hands gripping his aching cheeks. Mr Wood waited for the boy to leave, then he carefully tucked the cane up the sleeve of his jacket, leaving the school through the main entrance, and crossing the road. It was time for his rendezvous with Cavin!


More stories by Tristan