Reminiscences of a Headmaster -8


by Jamie <Woodthorne@csi.com>

Readers, if you want this rather long story to be continued please let me know. In the absence of feedback I shall not waste your time or space on MMSA Stories site and will post only to those who wrote after my last request for feedback. Cheers, Jamie

8. Alexander's first narrative

Standing before my erstwhile fellow 'judges' of our Society, and although James was at my side, I felt quite bewildered and rather astonished at firstly, James' father had spoken out and, secondly, that such a chorus of approval arose as we were directed to where we now stood. I brushed James' hand with mine as if to apologise for allowing my bravado and stupidity to bring us to this position and, with that touch, emotions and memories flooded back.

I had met James upon entering the School at the age of twelve and by the time my youthful innocence started to be replaced by a new sense of awareness, James had become my major goal in life. He was, and is, quite simply the most handsome boy/man I have ever known. And by the time we were fourteen we shared the same dormitory and shared the same adventures.

Our relationship developed quietly, almost silently. We never spoke of lust or longings until we were firmly devoted to each other but in those formative stages we simply looked across a football field or schoolroom at each other and communicated by gradually creating opportunities to be in the same place as one another. We would walk into town, one trailing the other at a discreet distance, and visit the same shops.

We would see one another from time to time as we exchanged occupancy of one or other of the Prefect's rooms, one of us teary eyed and the other scared and ashen faced. We bathed and displayed our stripes to our fellow classmates as custom required and took our time when changing our gear in the same room so that we might exchange surreptitious glances at one another's body.

As time went by we allowed ourselves to briefly rub shoulders and then, one evening after prep, the inevitable happened. I walked through a doorway as James came from the opposite direction, we knocked against each other and reached out to steady ourselves by holding the other and, in that instant, our fate was decided. The charge which exploded as we touched was so overwhelming that I knew what it was to be in love so deeply that I could have no other choice than to allow myself to totally consumed.

We were fifteen when we finally pronounced to one another our devotion and paid a heavy price for doing so.

The matter arose at the shed in which we housed the cricket equipment behind the scoreboard at the School oval. Without any premeditation, James and I arrived each with an arm load of stumps, balls, bats and other paraphernalia. I looked a James and he blushed. I blushed, James dropped the equipment he carried, I followed suit and suddenly our lips and arms were joined as those of only lovers can be. The shed was of course vacant and we prolonged that first embrace as long as we dared, given that other boys might be equally drafted into returning equipment to the shed.

We spoke as new found lovers do I suppose as we disentangled out bodies and went about the business of putting the equipment in its proper place. We shared our feeling and our anxiety about those feelings, we laughed at each other's hesitancy and quietly planned out how it might be best that we met in future.

It was the last embrace that caused the trouble for, it being clear that no other boys would be returning equipment that evening, we tarried longer than was proper or prudent and were spied by one of the Prefects as we hastened to make up time in returning to our dorm and bathing before supper.

Clemens was the Prefect's name and he was one of those prudes who suspects everyone of illicit thoughts and actions whilst fearing to admit his own true nature. His frustration he vented with a cane that he applied with venom to naked posteriors as often as possible.

That evening, James and I were his victims and he intercepted our return to advise us that we were required to attend upon him after supper.

James and I were so happy with our new found relationship and mutual admiration that we had not supposed that the ordeal we were to endure that evening might be so terrible as to weaken our resolve to see more of each other.

A thrashing by Clemens was a well listened to event by our fellow students who would be in prep as miscreants had their posteriors attended to because Clemens study was right above the main prep room and the sounds echoed through the wooden floors and along stone walls with astonishing clarity. And that evening it was to be James' and my posteriors that were to be the object of Clemens' sublimated frustration.

During supper, James and I could hardly keep our eyes from each other, such was our all consuming passion, and it was not until the bell went for prep that suddenly the reality of our world dawned upon us. James' face went pale as he rose and made for the doorway that opened the way to the corridor and stairs upon which we had to tread. I followed, wiping the moisture that oozed from my palms upon my trousers while all the time admiring the perfectly formed posterior that proceeded me. As we trudged towards our doom, James brushed my hand with his as if to reassure me that whatever might befall us, it could not surpass our bond. I responded to the pressure of James' hand to provide him with some minor testimony to my fellowship and support.

Clemens' study was set to one side of the building on the second floor and its large oak door was foreboding as we approached. I knocked twice and heard the muted sound of Clemens' voice as he bade us enter. James opened the door to Clemens' study and preceded me into the chamber.

Clemens stood before us and waited until I had closed the door before commencing his sermon. Whilst our only crime had been to be a tad late in returning to the dorm, Clemens assumed, with a degree of accuracy I had to admit privately, that we had been up to some unspeakable indiscretion for which we were to be caned.

To his credit, Clemens subdued his natural cruelty because of the absence of any evidence of serious wrong doing on our part and permitted James and I to remain almost fully clothed. I was the first to endure his chastisement and was required to remove my shirt and vest from my trousers before leaning over the edge of his table and spreading my legs so that he might have the optimum target at which to aim his cane.

James stood some distance from me but within my field of vision. He looked beautiful, if somewhat pale as I watched Clemens go behind him and retrieve a senior school cane from his cupboard. James looked at my eyes and then slowly shifted his glance to my backside. As he did so, I quivered a little which I am sure Clemens took to be a movement of fear rather than a response to the quite different image that popped into my mind.

Clemens had decreed that James and I would each receive four strokes of the cane and he used the cane to lift the tail of my shirt and the end of my vest out of the way and then he delivered the first to my posterior with all the venom he could muster. A split second passed, as it does in such circumstances, before the pain registered in my brain but the explosion of fire that my brain registered was greater than I had known up to that time. I gripped the edges of the table with all my might and willed myself to contain the outrage which my tightened buttocks felt.

Clemens took his time and allowed each stroke to take full effect before visiting the cane once again upon my posterior. The second stroke caught me well prepared and did not seem as painful as the first but as time would tell it had an equal effect upon my rear. Tears were forming in my eyes and I had a blurred vision of the anguished look on James' face as he observed my punishment.

The third 'crack' of the cane caught me lower than either of the first and gave me a lasting impression of just how painful the crease between ones thighs and buttocks can become when a cane is firmly struck there. I let out a slight cry at the pain that throbbed from my posterior and was somewhat grateful when the fourth and final stroke tore across my rump.

My backside was pain incarnate as I stood and shook hands, as custom dictated, with my tormentor and then shuffled to exchange places with James. As we passed, the backs of our hands glanced off one another and, as I wiped the tears from my eyes with one hand and tried to rub the pain from my backside with the other, I heard, rather than saw, the first lash of the cane strike James' rounded buttocks.

I heard James let out a gush of air as the first blow fell and, as my vision cleared, I saw his wonderfully rotund but clothed backside clench in anticipation of the second stroke. Despite the fearsome pain in my own posterior, my lustful nature began to make itself evident as I watched James' wonderful arse and was moved by degrees to a more rampant state as each stroke descended. For his part, James was stoical but nonetheless greatly pained as each lash struck his pronounced buttocks and I could see the tears in his eyes and upon his cheeks as the final blow arrived and he was permitted to arise.

Suitably chastened, James and I shook hands with Clemens as custom required and departed his study with all possible haste.

James as I were each of a like mind, heading towards to bathroom as we wipes tears from our eyes and cleared the snot from our noses and, when we reached the privacy of the bathroom, furiously tried to rub the pain away from our own backsides. We each washed our faces under the soothing cold water and gradually restored a sense of equilibrium and it was at that juncture that James noticed the swelling in my trousers and gently placed his hand upon me which led to an inevitable, and mutually satisfactory, climax within the confines of one of the lavatory stalls.

Our lust attended to, we proceeded to attend prep where our demeanour was closely inspected by all our comrades and, by all accounts, we displayed an incongruous degree of composure as we took out places.

At bedtime, in accordance with tradition, James and I had each to display our beaten posteriors for the assembled multitude as we prepared for bed but it was Clemens' handiwork and skill, rather than our proud striped buttocks, that commanded comments of approval from our colleagues. This was a salutary lesson in the innate viciousness of the young mind, and I stored away for future reference the callous disregard for James and my discomfort that was displayed by our peers.

That initial experience of lust and chastisement did not create a pattern as some of the fellows appeared to suppose although I was surprised that they so readily assumed that there was something more than a platonic relationship between James and myself. To my mind there was nothing that might have led the chaps to such a conclusion and it was when we were both punished for being absent from the cadet corps parade that forth a flow of comments which made it apparent that James and I were assumed to be engaging in more than the occasional feel or kiss. James was more concerned about the suggestion of our relationship reach the ears of his brother, or worse, his father, our Headmaster. For my part, I was concerned about our reputation, especially since our relationship until that time had not progressed terribly far.

Fortunately, from James viewpoint, our indiscretion was by one of the corps' "officers", a demon flogger by the name of Bentley. He sought us out and advised that our absence from the parade had been noted and that we should wait upon him that evening. During the late afternoon, James and I exchanged guesses about what Bentley might do to us. We reviewed every rumour that existed about Bentley's abilities with the cane, the suggestions that he chose to use a very heavy cane and some less than pleasant rumours about his predilection for using the over-sized organ that was said to hang between his legs for claiming the virginity of those whom he had the pleasure of chastising.

James and I, being "intact" at the time, pondered the last of these issues most carefully but assumed that rumours being what they are, the probabilities of this aspect of the rumours was probably a gross exaggeration. The balance of our time we spent making sure that we bathed thoroughly and were well dressed and presentable as we made our way to Bentley's study.

When we got there, we found that we were not the only miscreants to be the targets of Bentley's discipline, for another chap, Joshua by name who was at least a year older than us, was already standing outside the door awaiting his fate. I had experienced fantasies about Joshua for I admired the roundness of his posterior and the beautiful clarity of his skin. His face was, to say the very least, pretty and, although Jewish by religion, showed no signs of that fact in his features.

Joshua looked at James and I as we approached and gave us a weak smile that was both friendly and somewhat apprehensive. We greeted Joshua with equal apprehension and stood beside him whispering about our fears and the prospects that lay before us. To his credit, Joshua showed the maturity of his years by diverting the conversation from punishment to more personal matters by asking James and me whether we had, as rumour would believe, some form of intimacy between us. I recall James blushing terribly at the suggestion but, to his credit, or perhaps because of his views on Joshua's charms, James confirmed the rumour to which Joshua quietly nodded his head.

Despite the predicament that faced all three of us, Joshua continued to whisper to us about his lack of a "special friend" in his class and his loneliness and frustration. He admitted that he had often wanted to broach the subject with James and I but had never had the courage to do so. Abruptly James indicated that he would enjoy having some time with the older boy assuming I was agreeable. I indicated my consent to the implications of this suggestion and slipped my hand into James' and was reassured by the squeeze with which he replied. Joshua might become and intimate friend but would not interfere with James' and my love. James' reassuring gesture was suddenly broken as Bentley swung open the door of his study.

Bentley was a tall, solid man of eighteen, an athlete and almost revered as a major contributor to the success of our cricket and rugby teams. He dwarfed we three in size and was quite intimidating in every respect.

Bentley directed Joshua to go into his study and then ordered James and I to move well along the corridor in which we fearfully stood so that we might not hear Joshua's plight and find the sounds in some way erotic. While eroticism was the furthest thing from our minds at that precise moment, James and I complied and each of us noticed the long, senior school cane that was on display on Bentley's desk as we passed the open door.

James and I were perhaps some twenty feet from the door the Bentley's study and the thick oak panelling and stone walls ensured that sound from within Bentley's study were very muffled. Perhaps the pounding in our chests was louder than the muted sounds that began, after some time, to seep out of Bentley's rooms. The time between Bentley closing his door and the first muffled 'crack' of the cane as it struck the unfortunate Joshua was considerably longer than was required to deliver a lecture to the miscreant and the feint sound of the cane eventually reaching Joshua's backside explained the delay. Joshua was being caned on his bare posterior.

I heard six distinct 'cracks' of the cane on Joshua's backside and instinctively James and I began steeling ourselves for whatever would befall us. To our surprise and alarm, we heard two further strokes of the cane being applied. James and I exchanged fearful looks.

As one does in such circumstances, I started taking deep breaths in anticipation of Joshua's emergence from Bentley's study in an attempt to calm my nerves. As I did so I looked at James who had his head bent with his golden fine hair covering much of his face. I put my hand under James' chin, concerned that he might already be blubbing and raised his face so that his hair fell back. To my relief, James' face displayed no sign of tears but rather a steely determination and composure. I brushed his cheek with my hand and was surprised that he briefly gave me a one-armed hug in response. Had circumstances been otherwise I would have kissed him instantly.

Our brief period of intimacy ended but Bentley's study door remained closed. After quite some time, during which James and I were completely unnerved, we heard a sharp cry from Bentley's study followed by a long wail and what sounded like protestations. Any number of thoughts flashed through my mind (and I'm sure James' as well) but we could only ponder the infinite possibilities of what was happening.

In due course, Joshua walked from Bentley's study, heading away from where James and I stood. His gait reflected his chastisement and suggested something more but James and I would not find out exactly what for some time.

9. Joshua's first narrative

Bentley picked on me, I think for being Jewish. Every little mistake or infringement was seemingly noticed and I had received from Bentley either four or six strokes of the cane on several occasions during the year. Today, my "crime" was to have threatened to engage in fisticuffs with a couple of chaps in my dorm who were clearly ill disposed of anyone who was not of Anglo Saxon stock. They threatened to beat me because I was Jewish and, despite the odds, I challenged them to carry out their threat. As I issued my challenge I raised my fists waiting for the first move but both of them stood quite still, smiling. There I was, in the courtyard of our House, fists _c_o_c_k_ed, looking aggressive as Bentley stormed into the courtyard. Instinctively I knew that this was a pre-arranged confrontation and so I offered no excuses when Bentley expressed the view that I was apparently looking for a fight.

Late in the afternoon I was waiting outside Bentley's study, pondering just how brutal he was going to be with me when the two beauties, James and Alexander, approached. I had had many an erection just thinking about these two boys who shared and affinity with each other that suggested intimacy beyond what anyone had apparently actually observed.

The School was full of rumours about what the boys did together and which played the male role. One rumour had James as the dominant partner, I suspect because he was the younger son of the Headmaster while another story had Alexander, the taller, dark haired one enjoying the delights of the blond's favours. Either version was possible but, as time would tell, neither rumour was correct. That they shared an empathy was undoubted and while we waited for Bentley to summon us, and to take their minds off the pain they must surely be about to endure, I enquired of them whether they were in fact intimate.

The blond, James, the son of the Headmaster, blushed at my impetuous question but then, surprisingly acknowledged the truth of the matter. Alexander seemed to confirm their relationship but neither gave any indication of just how intimate they were.

Giving way to my impetuosity and throwing caution to the wind, I told the boys that I had been infatuated with them and was secretly jealous of their relationship. I confessed my longing for someone to relate to in these circumstances and it was young James who suggested that we three might get acquainted at some future date. Charmingly, Alexander grasped the rather bold James' hand as if to seek reassurance and it was quite clear that any misgivings on Alexander's part were set aside as James clearly squeezed Alexander's hand in a tender and reassuring manner.

The moment was brief enough but lifted my spirits and when, moments later, Bentley appeared and directed me into his study I felt a mixture of feelings. As well as feeling the immediate fear of the punishment to come, I also felt a sense of relief at having found the courage to express my feelings to the youngsters and to have been so readily accepted by them.

Just before he closed the door, I vaguely heard Bentley order the two lads to move further down the corridor for some obscure reason as my attention was fixed upon the cane that lay upon Bentley's desk, to one side of where I stood. Four foot in length and thick yet flexible, the cane was that used only on senior boys. I had experienced its caress before and its sight caused me to shiver in fear.

Having closed the door, Bentley told me that I was to be punished for having sought to create a fight. He asked me whether there was any reason for his not beating me on my bare backside, a question for which there was no acceptable answer other than "no". Bentley had emphasised the word "bare" which I had never heard before in such a context. For a moment I pondered the question and then simply replied by removing my trousers, lowering my underwear and bending over the desk which I had frequented before.

Bentley took his time and I was almost moved to provoke him bay asking him whether he was enjoying himself as he lifted the tail of my shirt up onto my back so as to give him an unobstructed target. I restrained my natural impulse to question his motivation and all the while felt the cane sliding over my bared buttocks.

The first stroke came like lightening and rapidly sent a sheet of pain from my backside to my brain. I let out a grunt for the pain was far worse than any I had experienced over my clothed backside before.

Bentley then proceeded to deliver five further strokes each of which challenged my ability to fight the natural instinct to cry out. Tears filled my eyes as I stood to restore my clothes but Bentley simply used the cane to push me chest back onto his desk. While 'six of the best' would normally be the maximum that any chap would have to endure in one session, Bentley made it apparent that I was only half way through my painful chastisement.

My spirit was broken as the thought of another six strokes registered in my brain and, to my disgrace, I begged Bentley for mercy.

Bentley stood there, his cane firmly held against my throbbing backside as if contemplating a compromise. Afterwards I would realise that this was all simply contrived but when Bentley proposed that he reduce the punishment to eight strokes in total in return for his having the pleasure of my bum, I nodded in agreement without realising what lay in store.

Two more strokes of the cane followed and my legs almost gave way as the pain reached new heights. I was oblivious to what else was happening as I lay across the desk, by brain consumed by the pain that throbbed from my backside.

As the pain started to level out into a single searing burn across my backside, I swallowed the muck that my tears were sending down my throat and moved to get up only to be told by Bentley that I had now to honour the rest of our bargain.

For a moment I was totally confused by Bentley's declaration but when I turned my head inquisitively to seek out what he meant, I immediately recalled the bargain I had made with the devil as I was greeted by the sight of Bentley, his trousers and underwear lowered, standing behind me with his inflamed organ in hand. For an eternity I watched fascinated and appalled as he applied his saliva to his aroused manhood and tried to fathom how he thought his long, thick organ was ever going to find a way into my innocent posterior.

During the years at School, I had known some boys who slept with older boys in return for favours or even, in some cases, for the sheer pleasure that they derived from intercourse of this nature. I had even wondered about such activity of the part of James and Alexander who were presumably waiting outside. But I had never experienced such a thing and would never have voluntarily contemplated such a monstrous piece of flesh entering me even for the most beautiful of men.

Bentley moved forward to claim his prize and I sung my head to the front and concentrated on the top of his desk as I felt him position himself between my nether cheeks. This large tip rested against my hole which I tried to keep clenched as tightly as possible in resistance to the increasing pressure being applied. I resisted as Bentley tried in vain to enter the portal but, with a chuckled, borne no doubt from experience, Bentley grabbed my throbbing cheeks and squeezed them. The throbbing pain was suddenly intensified seemingly a hundred fold but that was nothing to the incredible pain that came as my concentration lapsed and Bentley's organ entered my hole.

There is no way in which to describe the pain that I experienced but the scream that I emitted at this violation even surprised me. Bentley was obviously enjoying the sheer agony that I was experiencing and continued to ram into me. I let out a continuous wail of pain as slowly but surely his invading member split me in two and then I found myself begging for mercy.

Bentley obviously had difficulty impaling me entirely for he started to withdraw but then rammed back into me, making further progress towards his target. Time after time, he repeated this manoeuvre until I could feel his full weight upon my wretched backside and his pubic hair scraping where the cane had left its frightful impression. For a few moments Bentley rested as his sweat from his exertions dropped from his brow onto the exposed lower part of my back.

I knew what was to follow and as night follows day, Bentley proceeded to shag me for all he was worth. My continuing cries and groans of discomfort only served to inflame his enthusiasm for the task and he started to pound into me with greater and greater vigour. I could feel his organ swelling deep inside me as he neared his climax and then I felt his lust explode deep within my bowels. I sobbed wretchedly as Bentley lay on my back, panting from his labours and barley registered that his member was gradually subsiding in girth and length even as the last few drops of his discharge were released within me.

Satiated, Bentley withdrew and cleaned his organ on my shirt tail as I lay there feeling violated and weak. Bentley restored his clothes and then lightly slapped my ravaged backside and ordered me to get up and leave.

I cannot recall how, despite the pain and disgust I felt, I managed to dress and hobble out the door and down the corridor towards the nearest bathroom where I needed to expel Bentley's seed, use the cold water to take away some of the pain and also to wash the tail of my shirt which Bentley had abused in such a disgusting manner. I most certainly did not register Bentley's summoning of James and Alexander.

In view of recent tragic events, I would like to dedicate this story to a wonderful human being, Hugh Paul Keller, a long time friend and occasional play mate who, with eight others of our circle of friends, perished in New York City, 11 September, 2001. May they all rest in peace along with the 6,325 others who died with them and may we all be spared further horror and senseless madness of this kind. Jamie.


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