The Cleveland Academy

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This work is intended for ADULTS ONLY. It may contain depictions of sexual activity involving minors. If you are not of a legal age in your locality to view such material or if such material does not appeal to you, do not read further, and do not save this story.
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Stephen Short, was just fifteen years old. Four years ago, he had won a scholarship to one of the top boarding schools, ‘The Cleveland Academy’ situated in San Diego. He had been an above average student through each of his four school years at TCA. He had been described as responsible, hard-working and honest in every single one of the private reports that circulated amongst the staff and governors of TCA. He had grown in physical stature as well as academic achievement. Upright in integrity and upright in stature - had been a recent description used in one of the teaching staff reports. Stephen was one of only twelve male pupils in TCA as the academy historically, had admitted only girls.

When they had first admitted boys, they had decided upon fifty entrants. It had been quickly discovered that fifty boisterous boys would prove far too taxing for the all-female staff, and gradually they had limited the male entrants to the present level. In fact, when looking at the ratio of one hundred and fifty girls to twelve boys, the admittance of males was a mere sop to sexual equality.

The Cleveland Academy had a strict regime. School uniforms were mandatory and had to be maintained to a high standard, often inspected for smartness and cleanliness. For the girls, short pleated skirts with white shirt and navy tie, ankle socks and patent low heeled shoes. For the boys, black shoes and grey socks, short trousers, white shirt and navy tie. The uniforms were the same, whatever the age of the pupil. Bare legs were the norm for both boys and girls and had been since the academy had first opened its doors. Underwear was exactly the same for both boys and girls. White cotton pants, reasonably brief, but generous enough to accommodate both sexes, with elasticated waist and legs. Boys were required to pull down their undies as there was no fly.

The strict regime regulated every aspect of a pupil’s life. Prefecture was in place and prefects were chosen by merit from the sixth and upper sixth forms. Prefects would perform the dormitory checks for the younger girls and room inspections for boys and older girls. Prefects had the power to administer hand spankings and the slipper to boys and girls, as no allowance had ever been made to the rules since the admittance of male entrants to TCA. Boys always had single or shared rooms as did older girls. Younger girls slept in dormitories of no more than six beds.

Discipline had changed little over the history of the school. The writing of lines and the curtailment of free time by detention was standard practise. Corporal punishment took the form of paddle, tawse or cane for older pupils, where younger pupils could endure slippering or over the knee hand spankings. All corporal punishment was administered on the bared buttocks of the pupil, male or female. The combination of punishments was severe enough to ensure instant obedience and the good general behaviour of all pupils.

Stephen until recently had enjoyed the academy. All the teachers were young and had excellent qualifications. Because the teaching staff were recent graduates themselves, their thinking and knowledge was very up to date. In sciences, for instance, new discoveries and research were always immediately incorporated into the course. Stephen excelled in science, his special interest… in actual fact he excelled in all of his subjects. Whereas, his reputation could not have been rated higher amongst the staff, it certainly had been elevated to celestial heights amongst the girls. Who looked upon his physicality in an entirely different light.

He had been blessed with a face and body that could only be described in degrees of perfection. He stood at five feet and eight inches, tall. Certainly not overly muscular or in any way descriptive of a jock, his body was smooth and strong, with long legs, a lean and toned mid-section which flared to a hairless chest and smoothly muscled arms. His skin was entirely without blemish.

His face was neatly featured: Hazel/green eyes and small trim ears laying close to his head. His mouth and nose taken in isolation, might have been described as feminine, but strong even teeth gave his face a boyish look when he smiled. His absolutely straight hair was not thick but rather lighter weight and more refined. The colour was naturally highlighted between dark brown and several variations of lighter tones. He would flick his head on occasions making his hair fall neatly into place. His good looks were very obvious to everyone except Stephen.

Stephen should have been well content with his school life but in actual fact the opposite was true. Puberty had descended heavily upon this naïve young boy, bringing with it, its plethora of myriad difficulties, both physical and mental. We have heard the expression, ‘raging hormones’ and for this young boy it was an all too real phenomenon. It had overtaken his mind and his body – and for once in his life he had been completely and utterly perplexed by his emotions.

His single roomed study with tasteful furnishings of modern desk and chair. Scandinavian cupboards and shelving and bed with padded headboard, was a comfortable retreat for the troubled boy. His full-length mirror had become his companion, as he would lock his door and undress to examine himself. His short trousers and underpants would fall to the floor to instantly reveal the shameful developments that had overtaken his body.

His objects of interest and consternation had been the changes to his penis and testicles. His scrotum bulged; the pale skin now stretched tightly around the swollen orbs of his testes. His penis hung long and heavy over his scrotum, the skin smooth and pale. Unusually, his pubis was still entirely hairless, as were his armpits. Such was the intensity of his sexual epiphany, that he dare not even touch himself, knowing that the slightest stimulus would result in his penis erecting and standing out from his body in such a blatant display that it shamed him to look at himself.

If he caught sight of his face in the mirror, it would be bright red with shame and utter embarrassment. His morning erections became a constant worry. He would anxiously wonder whether the prolonged ice-cold shower would alleviate and retract his erect penis in time for him to don his tight short school trousers and allow him to dress for his lessons.

Stephen was naïve, especially where the wiles of young girls were concerned. Lately he had seemed to be the centre of attention for giggling comments, knowing looks and a variety of other little intrusions upon his private space.

It had been on Friday afternoon that Miss Roberts was handing out the history assignments.
Stephen had noticed that Stephanie Collins, one of the prettiest of all the pretty girls in the academy, had come to sit next to him. She had placed her hand upon the nape of his neck and stroked it gently with her fingertips. Stephen had blushed and looked at her in confusion. She whispered to him. “I think you have sunburn on the back of your neck, Stephen. Do you think it was from running so many laps of the track on Wednesday afternoon?” Because of her status as a senior prefect, Stephen did not question her motive and took her at face value.

She continued stroking his neck and Stephen seemed to succumb quickly to the sensuality of her touch. Of course, he had no idea that she was deliberately arousing him. He did not see her look down at his short trousers. She smiled to herself as she saw the evidence of her success. It was blatantly obvious to her, as his trousers bulged and tented, that he was in acute discomfort as he tried to shift himself in his seat. She could tell that he was desperate to alleviate the constriction he was feeling.

Her hand did not leave his neck until Miss Roberts approached their desk. She handed them two folders each and repeated the instruction that she had given to each pupil. “B is required on Monday and A will be due at the end of term.” His consternation at his arousal hardly allowed him to say, a very hoarse, “Thank you, Miss Roberts.”

It was now Monday morning. He had been working all weekend on his history assignment. He could not understand, as he had looked at the homework on the Friday night, how Miss. Roberts could have expected pupils to produce such a large complicated project over one weekend. They had been given two assignments, the other not being required until the end of term. He had not glanced at the second folder, merely assuming A came before B and busy as he was with producing his usual immaculate standard to the piece of work, he gave it no more thought.

It was just before lunch that Miss Roberts entered the office of Doctor Frost, the headmistress. “Would you just have a look at this Miss Frost and give me your opinion.”

After perusing several pages of the thirty-page assignment she turned to the back and noted that every quotation and fact had been clearly attributed. “A beautiful piece of work, concise and yet each section has been covered perfectly. Is there a reason for showing me this?” Miss Roberts smiled. “Yes. Headmistress, he has completed the wrong piece of work. The assignment that was due today, was at the most a couple of hours work! This assignment was not due until the end of term. So, in fact, he has failed to produce his homework. I am showing you this before I report him to your office.”

“I am not going to ask you whether the instructions were clear, because I am sure they were. You will have to notify me as normal.”

She smiled. “But I am pleased that you took the time to get my opinion.”

Louise Frost would never have believed of herself, before she took over the role of headmistress, that she had any sadistic tendencies. And yet, as she had shadowed the outgoing headmistress, she was astounded by the thrill she felt as the headmistress caned the lush bare bottom of one of the girls.

When it came to her turn to administer punishment she had found that the thrill had magnified in intensity, so much so, that her body had tingled and shivered in orgasmic delight.

Louise was only twenty-eight when she first administered corporal punishment.

The first boy she had punished, although only thirteen years old, she had hand spanked over her knees. As she stood the tearful boy upright she had had to make him turn around. Not to examine his buttocks, but to hide the orgasmic finale which coursed violently through her entire body.

Over time, Louise became adept at hiding her feelings and had found that, with tempering her excitement, her orgasms had become even more prolonged and satisfying. She found the humiliation and shaming of the recipients hugely exciting, particularly when she performed the ritualistic undressing and the baring of a young girl or boy added an anticipatory thrill that culminated in a true epitome of sexual excitement.

Over time she had added the technique of arousing the girl or boy. Often slipping her hand beneath their bodies as they bent over her desk or laid over her knees. She became almost cruel in arousing the recipients of her punishments so that they shivered and shook in utter abandonment.

Louise was not alone in her sexual proclivities. She noticed the very same predilection in many of her staff and in some of the prefects too. She knew that Stephanie Collins had seduced many of the girls in the academy and had often wondered what her entrée to her seduction was. One quiet afternoon, after classes had finished, she heard the sound of a firm hand spanking bared flesh. She had entered the room silently to find Stephanie Collins with a very pretty and delicious looking bottom over her knees.

Stephanie had merely looked up and had continued with her spanking. Louise was intrigued when she discovered that it was the very pretty and demure Priscilla Westwood that was the recipient pf Stephanie’s punishment. The Westwood family was one of the premier families in the state. As Louise had remained watching, Stephanie had stopped and explained. “This girl has decided that she will not be bound by the uniform code. The correct length of the skirt is fifteen inches from waist to hem. Miss modesty here has decided that hers will be eighteen inches.”

“Shall I continue, Headmistress?” Louise had smiled, especially as she saw that Stephanie had her other hand underneath the girl. She could clearly see the tips of her fingers protruding between the girls legs. The fingertips were just penetrating the girl’s labial lips. “Of course, Collins. We can’t have girls bending the rules to suit themselves.” She had looked at the florid face of the girl as she blushed furiously with her embarrassment and arousal.
Louise put her stamp of approval upon the punishment as she said. “Stephanie, dear. I would like you to ensure that your chastisement is thorough and memorable. Something that gets through to her false sense of modest behaviour.” Stephanie had smiled wickedly as she rested her hand upon the cheeks of the prone young girl. She rudely slipped her fingers between the crevice of the quivering and reddened bottom cheeks and pulled them apart. “Open your legs girl, I shall add extra strokes if you continue to clench your buttocks and squeeze your legs together.”

Louise winked at Stephanie as she spoke. “If you have cause to use your paddle. I would like you to massage her nether regions with cream when you have finished. If you apply it thoroughly enough, her bottom will benefit enormously, especially if she does not take heed of her lesson and you have to take her over your knees again.”

Stephanie immediately got the message, bright girl that she was. The fingers of her left hand began to move rapidly and intrusively dipping into the girl’s vagina. She had, once more, raised her right hand and had brought it down hard on the girl’s quivering bottom. Louise had smiled benevolently at Stephanie as she left the room to the sound of hard slaps and involuntary gasps and moans.

Louise was seated at her desk as her secretary buzzed through to say that Stephanie Collins wondered whether she could see her for a moment or two. Louise was always intrigued by Stephanie Collins and had often thought that her prefecture had been an excellent appointment. She replied in the affirmative and watched the astoundingly beautiful girl walk through.

Please take a seat Collins. “I trust that Miss Westwood was… erm overwhelmed by her experience”. Stephanie grinned wickedly. “Oh, several times, Headmistress. I can assure you that she no longer feels it necessary to dress so modestly. A true convert, I think.”

“Good, now to what do I owe the pleasure?”

Stephanie did not procrastinate, merely delivering her precise and accurate assumption. “I understand that Stephen Short is in trouble. I know of it through having a word with Miss Roberts and I feel responsible. I am sure that Stephen Short has recently reached puberty. He seems to be having a terrible time of it. Obviously, I am not privy to his intimate details, but I sort of checked it out for myself. It was at the same time that Miss Roberts was handing out the assignments. I stroked the nape of his neck, on the subterfuge of pretending he had sunburn there. He produced an instant erection in his short trousers. He was utterly distressed and embarrassed, I mean exceptionally so.”

She sat back and smiled at the headmistress. “I don’t have any facts, but I would be surprised if he was masturbating, or even knew how to. He is an excellent pupil as you well know. But he has not got the attitude of self-satisfaction. I saw him help one of the girls with her math. She is nearly two years older than Stephen and yet he explained everything clearly and more importantly, he did it with kindness. Even asking her, the answer after he had laid it out for her. Of course, she had grasped it, as he had really taken his time with her.”

Louise looked at her pretty protégé. “OK, so Stephanie… I will call you that while we are on our own. What are you asking me… to rescind his punishment?”

“Oh, no Headmistress, I would never be so presumptuous. Nor would I want to influence you to a leaner sentence. I wondered whether you could use it as a prelude to sorting out his angst. I mean Priscilla noticed it too. She came to me and said it was such a shame, that he was so mixed up and guilt-ridden.”

“Why did Priscilla come to you?”

“Well headmistress…” Stephanie was aware that the headmistress already knew the answer to that question. “…Priscilla was very grateful for me helping her with her… erm feelings.”

Louise smiled. “Leave it with me, Stephanie. I will give it some thought.”

It was a surprise when the form teacher for math, Miss Kahn, called for Stephanie Collins towards the end of the lesson. She presented her with a note. Stephanie walked back to her desk and looked at the note. She could not help the excitement that suddenly tingled through her body as she read the handwritten missive.

It was headed; Stephanie Collins and read; Please escort Stephen Short to my office at the end of the math period. Louise Frost. With only two minutes of the lesson left to go she stood and nodded to Miss Kahn and then walked back the few paces to Stephens desk. She bent low, resting her hand upon his shoulder and squeezed it gently as she placed her cheek next to his and whispered. “Please come with me, Stephen Sweetie, I have to take you to see the headmistress.”

She was delighted at his blushing face as he stood and stumbled down the aisle to the exit. As soon as they were outside the room, he turned to her. His face was as red as a beetroot and his breathing was laboured. “Erm… what…” Stephanie interrupted him. “Sorry Stephen, I don’t know any more than you do.” She stroked her hand up and down his back as they walked, feeling his intriguing body through the material of his shirt.

As they got to the outer office, Stephanie was surprised to see the pretty, young secretary standing by the side of her desk. Stephanie knew that she had only just turned eighteen, and yet she seemed cognizant of what was happening. She spoke clearly. “The headmistress has asked that you should go through.”

Stephanie placed her hand upon the small of Stephen’s back and ushered the bewildered young boy through the open doorway. The first thing Stephanie saw was that the young school nurse was in attendance. She was standing next to a trolley its, contents covered by a white cloth. In front of her she saw the headmistress seated at her desk. She was wearing a crisp white shirt and navy tie. Stephanie could not see the rest of her outfit but did notice the shapely legs and slender high heels, which were apparent beneath the headmistress’s desk. Stephanie whispered to Stephen, “Please stand to attention in front of her desk and wait for her to speak to you.”

Stephanie stood to the side and became aware of the young secretary entering the room and closing the door behind her. She had turned the key.

The headmistress’s voice was clear and not unkindly. “I have had a report from Miss Roberts, that you have failed to hand in your homework, Short. Am I correct in assuming that that is correct?” Stephen looked at her, his face already a deeper shade of red, if that was possible.

“Yes, Headmistress.”

“Have you an explanation, Short?”

Stephen did not hesitate. His voice was nervous but clear. “No, headmistress.”

“Well then Mr. Short. I have no alterative but to punish you.”

“Yes, Headmistress.”

Stephen looked glum but did not make any other remark.

“Miss Collins, as senior prefect, will you please prepare Mr. Short for corporal punishment.”

Stephanie was thrilled as she heard those words. She reached out and took Stephen by the arm. Her voice was crisp and authoritative. “Please stand with your arms at your side, Short.”

Stephen obeyed as he faced her square on. His lips were trembling, and his face was completely red. He breathed slowly and deeply as Stephanie flipped up his collar and began to undo his tie. She did not hurry as she knew that this exercise was not about expediency but rather about pure embarrassment. It was the same for any pupil who was about to be caned. Although usually there was only the prefect present.

He blushed as she handed the tie to the young secretary and begun unbuttoning the front of his shirt. When it was completely open she took each cuff and undid the button. She kneeled down in front of him and undid his shoelaces, and then opened up the leather until he could easily step out of them.

“Please step out of your shoes.”

Again, he obeyed without delay or comment. She took the shoes and again handed them to the young secretary.

She looked up at him, noting his shameful face as she spoke. “Please place your hands upon my shoulders, I am going to remove your socks, so lift your left foot first.”
She felt his tentative touch upon her shoulders. He put no pressure on her as he lifted first one foot and then the other.

She stood and placed her hand upon his belt, quickly and deftly undoing it and opening the fly of his short trousers. She could feel his body trembling, but he had not hindered her. She knew that his short trousers would stay up without support, as they still stretched tightly around his bottom. She pulled his shirt up and out of the gaping waistband. Then with a frisson of delight, she placed both of the palms of her hands flat upon his chest, feeling him shiver in embarrassment as she slid her hands up to his shoulder and then over and down his shoulder blades and the backs of his arms, taking the material with her.

She pulled the shirt from between his torso and his right arm and again handed the clothing to the secretary who seemed absolutely expectant at the results of this unusual event.

She kneeled on one knee, now acutely aware of his uneven breathing as she shimmied the short trousers until she was absolutely sure that they would not drag down his underwear.

She slid them down until they were at his feet. She had stroked over every inch of his thighs, gently easing the trousers down and at the same time, ensuring that her soft palms sensuously aroused him all the way down to his ankles. She knew that her strategy was completely successful as he gasped softly several times, drawing in his breath in a gasp, as she had let her fingertips trail against the backs of his knees.

She instructed him to step out of them and again handed her prize to the eager young secretary. Stephanie knew that there was no way that she could prepare herself for the complete baring of his beautiful body. But she was determined that he would remember exactly whose fingers had exacted this shameful deed. She stood close to him, face to face.

“I must now bare your body for your punishment, Stephen. Please keep still for me. I want you to put the palms of your hands flat upon your head.”

She somehow knew that the use of his Christian name had brought home the absolute shame of his exposure. She placed both palms against either side of his chest and slid them down to the hem of his plain white underpants. She waited until he had placed his hands upon his head.

Gently almost sensuously she slipped her fingertips inside the waist of his underwear and then in a little variation of her stance, she slid one hand inside and slipped it around until it was pressed against the cheeks of his bottom and then overtly and with a measured and humiliating signalling of her intentions, she slipped the other palm around until it was pressed against his penis and testicles. She held them there for several moments as she looked into his eyes. Her face betraying nothing of the thrill she felt as she slid the garment quickly down to the floor.

Her voice was cold and strict as she instructed him. “Step out of them please.” She slipped them from beneath his feet and handed them to the secretary. Not bothering to look at her eager young face.

Without waiting for instructions, she moved behind the boy and placed her hands upon his waist. She steered him with a light prompt of her fingers, to position his naked body about three feet in front of the headmistress’s desk.

“Spread your legs as wide as you can please.”

She kept her hand upon his hips as she waited for him to comply. Abruptly she slapped him across his buttocks.

“Wider than that, come along now.”

She heard him expel his breath. As as if in resignation, he spread his legs as she moved around him and looked down at his penis and testicles. She was delighted that his penis was already full and turgid. She knew that it would not take long before it was standing upright and jutting out from his thighs. Without doubt, this would shame him to the core.

She pre-empted any move he might make to cover himself. “Please stay in that position and pay full attention to the headmistress.”

It must be unimaginable to many, she thought. Just how utterly degrading it is to be made to stand with your legs astride, displaying your penis and testicles, completely and fully exposed, between your widely spread thighs.

The absolute shame it must instil while in front of a young and extremely pretty headmistress, sitting at her desk, cool and aloof while she examines your naked body.

For Stephen the added humiliation was that he knew with utter certainty that his penis would, very soon, be shamefully erect. Not only displaying the most intimate part of his body, but also his innermost feelings of sexual excitement. A blatant and humiliating revelation of his shameful thoughts.

The headmistress looked up into his face. “Pay attention to me, Stephen. I am afraid that you are to be caned. Six hard strokes of the rattan upon your bared buttocks. I hope that this will be a lesson to you.” She stood up and went to her cupboard which was in full view of the young boy. She turned a small brass key and opened the finely grained, carved wood door. With deft precise movements, she reached down and withdrew a long slender bamboo cane. She held it by the curled handle and returned to her desk, deliberately laying the wicked implement of chastisement along the ornate leather surface. It was lying right in front of the boy, and she knew with certainty, that he would be unable to keep his eyes from it.

Stephanie could not help looking at his face as he viewed the mottled surface of the rattan bamboo. She wondered how he must feel as he stood staring bleakly at the wicked looking, length of cane.
She noticed that the young secretary had taken one of several hardbacked chairs from the side of the room and had placed it in front - and to the side of his right foot with the side of the seat facing towards him. She had returned to fetch a similar chair. This one, she placed with its seat facing the other, but a little nearer the desk. The nurse, meanwhile, had fetched a folded blanket which she had placed upon the edge of the desk’s surface, immediately in front of the blushing young boy.

The headmistress spoke to the naked and trembling miscreant, both she and Stephanie had noted that despite the boy’s apprehension, his penis was now fully erect.

“Because you are a boy, the nurse will hold your genitalia so that it is out of the way of the cane.” She paused while the nurse sat on the first chair. “Miss Collins your prefect, will hold your head so please turn your head to the left when you are bent over. Right boy, over you go stretch your arms out across the desk when your head is positioned upon the blanket.”

They all watched as the boy took his hands from his head and bent over. His head was perfectly positioned on the blanket and the headmistress motioned to Stephanie to sit upon the chair. Stephanie seated herself and realised that her body was pressing against the side of his ribs. She whispered to him. Turn your face a little more towards me and then I can hold your head properly. He turned his head and then gasped suddenly.

Stephanie realised the reason for his gasp was that the nurse had just taken a firm hold of his genitalia. She turned her head and peered under his body. The nurse was cupping his testicles, pulling them forward while her other hand was wrapped firmly around his erect penis.

Stephanie smiled knowing that with his penis erect, it did not need protection. She saw the headmistress walk around her desk and stand in position, she could see that she was directly in line and Stephanie could observe her expression quite clearly as she held the cane ready.

Louise was thrilled and excited by the sight of Stephen’s perfect buttocks, nicely spread by his wide stance. She peered between his legs, seeing the hands of the young nurse obscuring every inch of his genitalia. She had nodded to her secretary who reached across from behind her desk and took hold of his wrists firmly. Louise steeled herself as she stroked her left hand over the proud globes of his buttocks, she felt him shiver in dread. “Be a brave boy Stephen.” She saw him shiver again at her words.

“Swish… Crack” The sound echoed around the room and everyone heard the gasp of pain from the young boy. His breathing was quickening rapidly. The headmistress waited. She knew that the pain was building to a crescendo as his body quivered with unprecedented agonies Stephanie felt his head rear up, she held it firmly and smoothed hands over his hair and his cheeks, trying to comfort him in any way that she could.

It was twenty seconds later that again, Louise stoked her hand down over his perfect buttocks, feeling the single raised welt, before raising her cane.

“Swish… Crack”

The force of the cane flattened his buttocks for a visible instance before leaving behind a livid red wheal. Louise realised that her expectancy of her innermost feelings did not remotely approach the tremendous surge of pleasure which coursed through her body. She realised that it was the perfection of his body that had heightened her pleasure to an elevated ecstatic surge. A deluge of unexpected sexual pleasure coursed keenly through her entire nervous system.

Stephanie could not help her own body trembling with selfish delight as she held his head firmly. Her hands were stroking and calming him. She ran her right hand over his shoulders in a comforting gesture and yet it was at odds with her own sadistic delight.

It was over twenty seconds before Louise again ran her hand over the quivering flesh of his buttocks. His writhing seemed to decline as her hand caressed the tortured flesh. She raised the cane, aiming at and finding the tender crease between thigh and buttock.

“Swish… crack.” His body shook and Louise saw that the insides of his thighs were shivering like an elongated facial tick that ran from the buttock to the knee of each of his legs.

She saw, that Stephanie was stroking his face, her head bent close to his whispering to him. Her other hand was caressing his shoulders as he struggled to cope with a seemingly unending torment. The nurse suddenly let go of his penis and squeezed his testicles firmly. She could not believe it, and yet the boy’s penis was throbbing so violently, that she dare not supply another single iota of stimulus to his hardened member for fear of him ejaculating instantly.

Again, the headmistress stroked her hand over the trembling and striated buttocks of the young boy’s reluctantly offered flesh. She had not varied the strength of her strokes but knew that the boy was suffering the cruel accumulation of persistent torment.

She raised the cane, nearly choking with the swift stab of unadulterated pleasure that engulfed her.

“Swish… Crack. The boy gasped and breathed in a huge gulp of air, seconds later expelling the air out through his chattering teeth in a high-pitched hiss. His body jerked within the confines of the hands that held him. Stephanie whispered into his ear… “Poor baby, it will soon be over. There, there.”

Jenny Simmons could not believe the intensity of the punishment that she was witnessing as she held his wrists even more firmly. Her face was flushed, and she could not help wondering why she felt so excited as the boy struggled involuntarily each time the cane bit into his flesh.

She could see that his mouth was open and that he was gasping for air. She watched the implacable face of the headmistress as she stroked her hand over the boy’s quivering buttocks. She waited, holding her breath, as did the young school nurse and the beautiful young prefect. There was complete silence in the room as the headmistress raised her cane for the fifth time. She knew, from experience, that the last two strokes were almost unbearable.
She raised the cane, aiming for the top of the buttocks. She waited those few extra seconds delighting in the baited, breath of everyone in the room, including the helpless and anguished young boy.

“Swish… Crack.” The guttural grunt that she heard from the boy’s anguished and opened mouth told her that it was as she had predicted, intolerable.

Stephanie stroked her hands over the Stephen cheeks, knowing that it was a mere sop to his abject misery. She slipped her right hand beneath him and smoothed her hand under his chest, paying attention to his nipples, which seemed to be hardened and erect.

They all awaited the final stroke but instead saw the headmistress whisper to the nurse, who nodded vigorously. Nurse Boyd had served the headmistress on previous occasions when she had caned boys. But she had never been given these particular instructions before.

She smiled to herself as she tentatively touched the shaft of the young boy’s penis. The straining flesh was hardened and yet the urgent throbbing had subsided somewhat. She wrapped her fingers around it and retracted the prepuce until it was tightly stretched back towards the base of the shaft.

Louise ran her hand across the five red welts of raised flesh. She heard the boy suck in his breath as she raised the cane. Stifling the thrill that threatened to engulf her emotions, she aimed for the under part of Stephens quivering bottom cheeks.

“Swish… Crack.” The boy was silent for a moment and then he gasped and cried out in anguish. “Hoo…hoo hoo.” Stephanie saw the tears run down his cheeks and his lips tremble as his body shook. She could not believe the anguish on the young boy’s face. She was surprised at the rapidity in which the headmistress instructed Jenny Simmons to let go of his hands. “Stand him up Please nurse Boyd and Miss Collins.” As soon as he was standing Stephanie held her arms around his shaking body, unsure as to whether he would collapse.

She was utterly taken aback as the headmistress inserted her hand between the tortured cheeks of his bottom and nurse Boyd began a rapid assault upon his penis. The nurse spoke to her, winking as she gestured towards her hands which were rapidly running up and down the shaft of his penis. “Will you hold his testicles dear, firm squeezes while I extract his semen.” The nurse quickly pulled the prepuce back and held it, baring all of the boy’s sensitive membranes to the cruel stimulation of her other hand. Stephanie looked at the boy’s face after she had taken a firm grip of his testicles with both hands.

The head mistress held him with her hand around his waist from behind as she rapidly jabbed her fingers in an unending assault on his sphincter. It was not even thirty seconds before the young boy was made to ejaculate helplessly upon the surface of the desk. The young secretary was unable to escape the first jets of semen which landed upon her striped shirt, decorating it with large globules of sticky, thick semen. The boy’s head was thrown back and it seemed as if he was delirious as the nurse diligently increased the firmness and the speed of her assault upon his straining penis. It seemed endless and to anyone that did not know that this was a long overdue and virgin orgasm, cruelly procured from an anguished beating, it was a truly magnificent entrée to the adult world.

The headmistress gradually stilled her hand as the boy began to slump towards the floor she held him with both arms and steered him to Stephanie’s hastily vacated seat.

Stephanie saw the boy wince as his lacerated bottom touched the seat. She saw his penis throb once and emit another large globule of his torturously extracted semen.

The headmistress left the boy to the tender touches of Stephanie and the young nurse. She put away her cane, feeling fulfilled and satiated. She sat at her desk and watched the young boy delighting in his nakedness and his surfeit of anguished sensations. She watched Stephanie caress him and comfort him as the nurse wheeled her trolley out of her study. She had let her young secretary go to get tidied up as she spoke to Stephanie, thrilling the young girl with her instructions.

“I think, my dear, that you may inspect this young boy’s room, first thing every morning and then at lunchtime after you have both eaten and then just before lights out. A thorough extraction each time please. Gently for the first few days and then you may spank him and arouse him as you wish. I think that should get him back to work with his usual vigour. Let me know of your progress, although I am sure you will vary your routine to suit if you find that it is insufficient. Does that sound manageable to you?

Stephanie looked at her new mentor. “Oh yes headmistress, I am sure that it will ensure that we are both on top form. May I assume that I may ensure a full and complete evacuation of his scrummy boy juice. I was thinking that the nurse might provide me with a rubber glove and a suitable lubricant. I think a young boy like Stephen should feel the benefit of a thorough goading of his prostate.”

Louise looked at her in astonishment. “You have experience of that?”

“Oh, yes, Headmistress. I regularly ensure that my little brother gives his all. I don’t tolerate half-hearted emissions. A firm finger or two inside his little bottom ensures that he pays full attention to my ministrations.”

Louise raised her eyebrows in admiration. “Yes of course Stephanie dear, I am sure Nurse will provide everything you need, and Stephen must certainly pay attention to his duty to perform to his best ability.”

Stephen did not seem to have taken in any of the conversation. He looked dazed and bewildered. His face was blushing profusely as he sat helpless and drained upon the hardbacked chair.

The headmistress looked again at the boy’s naked form and smiled at her young prefect. “You may start on his regime today Stephanie, as I am sure the recuperative powers of youth will soon make themselves felt. He is obviously extremely malleable and quite timid.”

The headmistress looked at the bulging scrotum and the still turgid appendage lying between the boys legs.

“He certainly has the wrong surname don’t you think, Stephanie, dear?”

(End of File)