2 comments/ 39985 views/ 1 favorites Six of the Best By: Topwork Alex stood outside Sister Veronica's office, his clammy hands clasped together behind his back. This wasn't a new experience for him, being summoned to explain his behaviour. In fact it was the second time this week, this being his final term at school. He'd been attending St. Margaret's Boarding School for Boys most of his teenage years, but since his 18th birthday, the shackles of authority were becoming more than he could bear. This restlessness had manifested itself in a number of ways but mostly he was just plain disobedient to his teachers. He'd also been known to play pranks on fellow pupils and had even left the school premises at night to cross the playing fields in search of a bar that would serve him alcohol without ID. This time he'd been caught red handed, daubing profane graffiti on the walls of the school chapel. To him, it was all the same, just something to distract him from the endless monotony of being at St. Margaret's, but his teachers had taken exception this time, He'd been summoned to the office of Sister Veronica, deputy headmistress and the bane of his life. He stood at the her office door, knowing full well that she was already inside there. He glanced over his shoulder and looked back down the empty hallway he'd just walked along; he could turn and run, but the thought quickly left his mind. No point delaying the inevitable, he reckoned and so he knocked twice then held his breath. "Enter," came the familiar voice of Sister Veronica. Alex exhaled and turned the round, brass knob, opening the door to see his austere teacher sat at her desk. She put down the black notebook she had been reading and with a gesture of her hand beckoned him inside. He stepped into the room and closed the door. She rose from her seat and walked over to the largest window in the room and stood with her back to him. She appeared to be watching something occurring outside, but from where he was standing, Alex couldn't say what it was. "You asked for me, Sister Veronica," said Alex, who had never felt comfortable calling a woman older than his mother 'sister.' It felt unusual saying the word, even though he understood that the title was correct. "What will we do with you, boy?" asked Sister Veronica, rhetorically. Before he could make a response, she turned to face him and her cold grey eyes told him that his opinion was not needed. She sighed and looked to the ceiling, "You do understand that my hands are tied on this matter? The endless red tape that binds our educational institutions these day, it really does make me want to weep. I shall have to inform Mother Superior and she, in turn, will have to inform your father. Alex swallowed audibly. He had been sent to boarding school by his father who wasn't inclined to have a troublesome teenager taking up his time and was more than happy to pay someone else to raise him. On more than one occasion his father had warned him that if he couldn't learn obedience from the Catholics, there was always his Uncle's farm in Nebraska. The thought of living in that wilderness made him shudder. "My father?" managed Alex, the fear in his voice was apparent. "Yes, your father," replied Sister Veronica. "You have much potential, boy, but you seem so very determined to squander your education. I shouldn't expect any less, your father was much the same, but at least in his day there were," she paused, "less bureaucratic ways of teaching discipline." She crossed the room in three strides then stooped so that her nose was only an inch away from Alex's. "When you were left with us, I made a promise to your father that we would mould you into the same calibre of man that he was. Perhaps you might find," another pause, "traditional treatment to be more instructive? What says you, boy?" He hesitated, uncertain as to whether this was another rhetorical question or if he was required to answer this time, She remained, unflinching at his eye level and so he began to speak. "I don't understand, Sister..." Alex began, but she cut him off in mid-sentence. "Don't play the fool with me boy, we both know that behind your sarcasm and your incessant insolence you're a good deal smarter than you'd like to admit. Since I know what worked for your father, I'll give you a choice; you have transgressed against the code of conduct enshrined in this institution for over a hundred years. This will not do." She straightened, but peered down at Alex over the round, copper coloured frames of her spectacles. "I am professionally obliged to ensure that your father is notified of your behaviour. However, I am honour bound to him that I must strive for your betterment. The decision you must make for yourself boy, is whether or not you are willing to take your punishment like he did?" Alex opened his mouth, but couldn't formulate the words to make articulate his thoughts. She seemed to be suggesting that if he agreed to whatever she had in mind, his father need not know a thing. This wasn't a decision he needed to dwell upon for long. "I want to be made better, Sister Veronica," said Alex and the woman pulled back her lips in a thin smile. "Very good then." She seemed pleased that he'd come to the right decision. Actually, that wasn't quite right, satisfied was probably closer to the truth. She pivoted quickly on the spot then walked over to a tall bookshelf in the far corner of the room. Reaching around the back, she took something from behind it that Alex couldn't see at first. When she turned back to him he understood in an instant what it was and why she kept it hidden from view. It was a thin, rattan cane and Alex felt his mouth involuntarily fall open as she held it horizontally in front of her at arm's length. She flexed the cane, making her knuckles whiten as she gripped it. "Go face the window boy," instructed Sister Veronica. Alex, in an almost trance like state, did as she asked and looked out across the school playing fields. Two teams of first years were being taught rugby. "I'm ready," said Alex. "Bend over and show me your backside," Sister Veronica told him. Slowly, Alex doubled over and looked down at his feet. The seconds passed until he realised what was expected of him. He unbuckled his belt then unfastened his trousers and slid them down past his knees, letting them fall around his ankles. Taking a short breath, he hooked his thumbs into the elasticated waistband of his briefs and pulled them down too, bringing them to rest just below his shins. He could feel the cool air of the room on his buttocks now. Alex thought that his flaccid penis was probably out of her sight, but he was sure Sister Veronica would be able to see his balls, hanging between his thighs, exposed and unprotected. He heard her footsteps as she approached him and the skin of his scrotum tightened, a wave of nervous anticipation washing over him. "You'll want to bite on this." Alex turned his head at the sound of her voice and something cold and hard was pushed into his mouth. The sour tang of old wood met his tongue and he recognised it was a ruler, twelve imperial inches long. He bit down and fixed his eyes at the floor, his hands resting on his knees to maintain his balance. "This is for your own good, boy," she told him. The first stroke was so sudden, that Alex felt it on his skin before his ears told him that he had already heard it whistle through the air. His jaw clamped down harder on the ruler and his teeth dug into the soft wood. Again, the cane struck and an involuntary noise rose up at the back of his throat as the pain burned its way through his body. Sister Veronica brought the cane down once more and Alex felt the strength in his legs weakening. The fourth stroke hit him lower and glanced across his balls sending a new kind of ache up into the base of his gut. Another stroke and the sound of the cane was followed by the wet splatter of urine hitting the tiled floor as Alex lost control of his bladder. A warm sensation splashed against the inside of his legs and a small pool formed between his shoes that spread out around his soaking trousers. The final stroke hit him squarely across the buttocks and with a sharp cough, he spat out the ruler which clattered nosily as it landed. Wordless quiet filled the room, broken only by the sound of Alex's breathing. Slowly raising himself upright. Alex cupped his damp genitals in his right hand before he shuffled around to look at his teacher. He watched her as she returned the cane back to its original place behind the book shelf. She sat down at her desk again and resumed reading from her black notebook. Half a minute passed and still Alex waited. "You may go now, boy," said Sister Veronica without lifting her eyes from the page. Alex bent down pulled up his soiled clothes, wincing as he gingerly lifted them over his sore buttocks. The cold, clammy material was uncomfortable on his skin but continued to dress himself nonetheless. Once done, he walked over to the door, leaving a trail of wet footprints behind him but he didn't look back at them. He turned the round, brass knob and stepped through, closing it behind him. The End Six of the Best 'Ah. Mrs Preston. Do come in.' The Headmaster rose slightly from behind his large desk but the late-afternoon light flooding in through the windows behind him made it difficult for Mrs Preston to see him properly. There was, however, no mistaking his rich authoritative voice. 'It's Dale, isn't it?' 'Delia,' Mrs Preston said. The Headmaster turned his head to study the free-standing monitor that was set at an angle of 45 degrees on the right-hand side of his desk. With his head turned, the combination of the light from the window and the reflection from the monitor highlighted his profile. He seemed to be frowning. 'Delia?' Mrs Preston nodded. 'Oh, yes. Your name. Yes. I see what you mean,' he said. And then he added: 'But I was referring to your boy.' 'My son's name is David,' Mrs Preston said. The Headmaster nodded. 'Hmm. Yes. David, Dale, Delia -- so many Ds, Mrs Preston. So many Ds.' Mrs Preston laughed nervously. 'Here at Sebastian House we are not fond of Ds, Mrs Preston. D is the initial letter of both dunce and dullard. And here at Sebastian House we do not like dunces or dullards. They lower the tone; spoil the average; ruin the reputation. Is your boy a dullard, Mrs Preston?' 'No. Far from it, Headmaster!' 'And yet I see that last term he got a D in Divinity. D for dunce; D for dullard; and a D for Divinity. Why do you think that might be, Mrs Preston?' 'I can only surmise that The Rector disapproves of his atheism.' 'Hmm. You surmise do you? He's a little young to be an atheist, isn't he? Dale, I mean -- not The Rector. The Rector is old enough to be whatever he wants to be.' 'A little young? No, I don't think so. I would prefer to think that Harry Potter is a little young to be a wizard,' Mrs Preston said. 'And my son's name is David, not Dale.' It was hard to tell, but she thought that The Headmaster may have smiled. 'Well, I suppose we had better get on with it,' The Headmaster said. He eased himself out of his high-backed leather chair and stepped out from behind the desk. 'That skirt suits you,' he said. 'It suits you very well indeed. I like a nicely-tailored pencil skirt on a woman. Very smart. Although, of course totally unsuitable for this situation.' 'I assumed that I would remove it,' Mrs Preston said. The Headmaster nodded. 'Assumed, did you? Well, yes. Yes, of course. When you're ready then,' he said. Mrs Preston reached across her body with her right hand and, slowly, lowered the zip that ran from her slim waist and over her elegant left hip. The Headmaster watched intently, waiting for the magic moment when all would be revealed. For a moment or two, Mrs Preston just stood there, watching the watcher, her zip unzipped, but her left hand keeping her skirt discreetly in place. And then, with a slight teasing smile, she lowered the skirt to the ground and stepped out of it. She was wearing black lacy-topped stay-up stockings and plain black high-heeled shoes. But she was not wearing any knickers. From the smile on The Headmaster's face, he did not seem at all disappointed with what he saw. 'Right. Where would you like me?' Mrs Preston asked. The Headmaster indicated a smallish leather-covered chair with arms discoloured somewhat by the nervous sweat from many hands over many years. 'If you would be so kind as to bend over that chair,' he said. 'With your feet spread slightly and your posterior towards the light. I like to be able to see what I am doing.' Mrs Preston took up the position as requested. 'Like this?' she asked. 'Thank you. Perfect,' he said. Out of the corner of her eye, Mrs Preston observed The Headmaster unbuttoning the fly of his tweedy suit trousers and extracting his swelling penis from within. She assumed that the beginnings of his erection were, in part at least, prompted by the appearance of her slim-but-shapely naked backside and she took it as a compliment. The Headmaster selected a whippy cane of lightish weight from the extensive collection in the umbrella stand and swished it, briskly, a couple of times in the air above Mrs Preston's pale, exposed buttocks. A careful listener would have noted that, in addition to the airy whistle, the cane made a slight shuddering sound as it buffeted the air. 'Ready?' The headmaster enquired. But he didn't wait for a reply. Thwack! The first blow took Mrs Preston completely by surprise. She felt a sudden sharp sting across her buttocks, but then, after a couple of seconds, the sting was partially suffused by the beginnings of a warming glow. Thwack! A second blow followed. And then a third. Mrs Preston felt the warming glow spreading across her trim buttocks and down into the crevice between them. At the junction of her shapely thighs, she could feel her labia majora beginning to tingle and swell. The landing of the fourth blow -- thwack! -- caused her real pain. And yet she could also feel her labia majora continuing to swell and open, exposing her delicate pink labia minora within. Glancing back, she confirmed that The Headmaster, too, was enjoying a swelling of his own. Thwack! Five. Ouch! Now she had had enough. The pain was beginning to outweigh the pleasure. Or was it? Oh well ... one more. She waited, becoming acutely aware of the sharp contrast between her now hot and stinging glutei and the breeze-cooled surface of her dampening anus and vulva. Come on, man. What's keeping you? Mrs Preston glanced behind her once more. The Headmaster was tapping the cane on his now almost fully-erect penis. 'Well done, my beauty,' he muttered. And then ... thwack! 'There. I'm pretty sure that makes six. And now, if you will just maintain that position for a little longer, I will summon Matron.' The Headmaster placed the cane back in the umbrella stand and returned to his desk, slowly stroking his penis as he went. Leaning forward, he pressed the button on the small intercom unit. 'When you're ready, Matron,' he said. Fifteen or 20 seconds later, the door opened and Matron -- fiftyish, upright, with a crisp white apron over her white-collared navy blue dress -- entered the study pushing a small stainless steel trolley. Parking the trolley conveniently near to Mrs Preston's striped and reddened bottom, Matron donned a pair of surgical gloves. 'No latex allergies?' Matron asked. 'Not that I am aware of,' Mrs Preston replied. Matron picked up one of the containers from the trolley and squirted some sort of clear gel-like substance onto a soft cloth. Gently -- but efficiently -- she began wiping Mrs Preston's posterior, paying particular attention to the crevice between her buttocks and to her sweat-glistened anus. Mrs Preston responded by relaxing her anus, and then relaxing it still further when Matron began to probe it gently with her gloved and lubricated finger. While Matron continued to work Mrs Preston's anus with one hand, her other hand reached under and parted and lubricated Mrs Preston's inner labia. Deftly, Matron's latexed finger located Mrs Preston's clitoris and began to massage it. The effect was almost instantaneous. Mrs Preston let out an involuntary squeal and shuddered with delight. Matron continued her expert ministrations for another two or three minutes, bringing Mrs Preston to at least two further small-but-not-unsatisfying orgasms. 'I think we are almost ready,' Matron said. The Headmaster grunted approvingly. Matron removed her surgical gloves and discarded them into the small litter bin that was attached to one end of the trolley. She then briskly rubbed her hands on a clean cotton towel before donning a fresh pair of gloves. 'I think the small size will be adequate for Mrs Preston,' she said. Mrs Preston's brain was almost overloaded with sensations, but she did, fleetingly, wonder: 'small size what?' The answer came almost immediately as Matron removed the sterile packaging from a finest quality silicone anal plug (Size: Small) and smeared its business end with a generous coating of the clear gel. Deftly, the thumb and forefinger of Matron's left hand spread Mrs Preston's glowing buttocks while her right hand gently but firmly worked the plug into Mrs Preston's eagerly waiting anal passage. 'There,' she said. There, indeed, Mrs Preston thought. It was the first time that she had experienced an anal plug, but, having now crossed the street (as it were) she hoped that it would not be the last time. 'Ribbed or plain?' Matron asked The Headmaster. 'Hmm ... plain, I think,' he said. Matron reached down to the lower level of the trolley and retrieved a box of foil-wrapped, pre-lubed condoms. 'Shall I do the honours?' she enquired. 'Thank you,' The Headmaster replied. Matron removed one of the condoms from its packet and unrolled it, slowly, carefully, almost lovingly, down over The Headmaster's erect purple-headed penis. Then, with practiced ease, Matron parted Mrs Preston's puffy labia and introduced the head of The Headmaster's condom-clad penis into the glistening entrance to Mrs Preston's vagina. The Headmaster entered Mrs Preston in one long slow thrust. His penis was not of extravagant proportions but, with the anal plug already in place, Mrs Preston found it satisfactorily filling. 'Ah. Yes,' The Headmaster said. Meanwhile, with her contribution to the coupling completed, Matron took up a position in front of Mrs Preston and The Headmaster. Reaching down, she grasped the hems of both her skirt and her apron, and quickly rolled them upward until they formed a neat soft roll at her waist. An unseen manoeuvre behind her back secured the roll, leaving her gloved hands free to explore her vulva. (Like Mrs Preston, Matron had foregone the opportunity to wear knickers beneath her outer apparel.) While Mrs Preston was in no doubt that Matron's performance was first and foremost for the benefit of The Headmaster, she herself found it pleasantly arousing. Back in her university days, Mrs Preston had occasionally enjoyed a mutual masturbation session with her best friend, Hazel. The two young women would position themselves at opposite ends of one of their beds and, restricting themselves to just their fingers, they would hold informal competitions to see who could come first and who could come most. But that had been more than 15 years ago. And, anyway, watching Matron expertly fingering her fleshy, mature, hair-fringed cunt was very different to watching Hazel frigging her smooth, almost girlish slit. The Headmaster, too, seemed to appreciate Matron's performance. His long, slow strokes gave way to shorter and shorter, faster and faster thrusts accompanied by approving grunts. 'Oh, yes,' he said. 'Oh, yes. Oh, yes. Oh, fucking yes! Work that cunt, Matron! Work it, I say! Work it!' But Matron did not have to 'work that cunt' for very long. Another half a dozen or so strokes from The Headmaster and he was filling the condom with warm seminal fluid. Matron allowed herself a further few seconds of self pleasure before lowering and straightening her skirts. By the time The Headmaster had withdrawn, Matron was on hand to remove the condom and gently wipe down The Headmaster's wilting penis with a fresh wet wipe. 'Thank you, Matron,' he said. The Headmaster returned -- with a slightly unsteady gait -- to the high-backed chair behind his desk, while Matron selected yet another fresh pair of gloves and set about wiping down Mrs Preston's nether region. 'Shall I remove the plug?' Matron enquired. 'Or would you like to keep it in a for a little longer?' Mrs Preston straightened up and wriggled her hips slightly. 'You know ... I think I will keep it there for a little longer,' she said. 'Yes.' Matron nodded. 'As you wish.' And then, turning to The Headmaster, she asked: 'Will that be all?' The Headmaster nodded. 'For the moment, thank you, Matron. For the moment.' After Matron had left, Mrs Preston stood for a moment or two, enjoying the cool air on her freshly-washed pudendum. And then she shimmied -- gingerly -- back into her elegant pencil skirt. 'Thank you, Headmaster,' she said. 'And thank you, Mrs Preston,' The Headmaster replied. 'As you well know, we have a fine tradition to uphold here at Sebastian House and I feel that it is important that we involve the parents in the life of the school whenever and wherever possible.' Mrs Preston nodded. 'Oh ... and one little thing, Mrs Preston ... if you could perhaps encourage Dale -- sorry, I mean David -- to be a little less militant in his atheism ....' 'Well ... no promises, Headmaster, but I'll see what I can do,' Mrs Preston said. 'Thank you,' The Headmaster said. 'You know ... for the good of the school. Don't want people thinking that Sebastian House is in any way weird, do we?' 'Probably not,' Mrs Preston said.