Reminiscences of a Headmaster-13


by Jamie <Woodthorne@csi.com>

OK. To the two people/cretins who issued threats last time, my good friends at the AG's office see no violation of any law with this story and will be paying you a visit regarding vilification statutes! So get stuffed!!

Standard disclaimers apply and don't read if you don't want to or are not legally able to do so or are certified bible-bashers. Everyone else, enjoy and feedback would be appreciated.

26 James

Joshua reminded us of his ordeal so many years ago and I thought back to those days and recalled privately our hols at Joshua's home and was quite startled to think of the adventures we had had and the fact that Joshua had only just lost his virginity and in such a despicable manner. He had never mentioned it until now and all the while I had assumed that Alexander had been the first into Joshua's hole. I could not recall any signs from Joshua during the hols that he had experienced such trauma and, indeed, he happily participated in our ever-expanding _s_e_x_ual activities.

I recall the very day that Alexander, Joshua and I first went beyond kissing and sucking and got down to the serious business of intercourse. Joshua's father was absent from the house attending to business in the City and we three lounged about in the great hall that looked out upon the gardens.

_s_e_x_, never being far from our minds, leapt into our rambling conversation and quickly became the dominant subject. We three has soon locked the doors into the hall and were naked and sporting erections. General play became more focussed as Alexander began to rub his swollen member along my crack and, using his spittle for lubrication started to ease his fingers into my arse. Joshua got into the act by starting to give oral stimulation to Alexander and one thing led to the next and soon it became evident that Alexander was intent on seeing the act through to conclusion.

Joshua sought out some butter from the kitchens and liberally applied it to Alexander's throbbing organ. Despite the preparation and the lubrication, the instant that Alexander started pushing into me was painful in the extreme and as he filled me with more and more greater discomfort ensued. Joshua urged Alexander to take his time and to pause in order that I might adjust to the intrusion, but Alexander was too impatient. Waves of pain spread through me as Alexander commenced his rogering of my no-longer virgin arse and, mercifully, spent himself within a few minutes, such was his excitement.

I had not enjoyed the experience at all and scolded Alexander for being too enraptured with his own please to give me any thought at all. Joshua agreed that Alexander's performance was selfish in the extreme (I having no knowledge of his own experience) and determined that he and I should punish Alexander accordingly.

Being the dominant one in our relationship, I had full command of Alexander's attention and obedience. Despite his apologies, Alexander knew that he would be punished and the only question in his mind, I am sure, was what form of discipline I had in mind.

I took Joshua to the far end of the large room and quietly enquired if he had anything suitable for the purpose of punishing Alexander. He responded that his father kept a stock of canes which he used to punish Joshua when a significant transgression occurred and I sent him to fetch a suitably heavy one so that I might impress upon Alexander the error of his ways.

Joshua soon returned with a heavy cane such as one that a Prefect at School might use upon the clothed buttocks of a senior boy and Alexander was shocked when he realised that I intended to use it on his naked backside. I directed Alexander across the ark of one of the chairs and asked Joshua to hold him down while applied a dozen strokes. Alexander immediately protested the severity of the punishment and I dutifully increased the number of intended strokes by one to make a baker's dozen. Realising my determination, Alexander became quiet and steeled himself for the ordeal.

I took my time administering the cane to Alexander's posterior and relented in the extent of my vigour somewhat as I saw the damage that the first six strokes caused. Nonetheless, Alexander was properly chastened by the caning and begged my forgiveness. I kissed him long and hard to show that his painful sodomy of me had not altered my love for him.

That evening we received a message from the butler stating that Joshua's father had been delayed overnight in the City. We dined in the splendour of the 19th century dining room and then Joshua dismissed the servants that we might be alone. We spent the rest of the evening engaged in all manner of debauchery and it was during those furious hours that I first encountered the charms of Alexander and Joshua's nether holes. Even at that time Joshua did not let on about his vile treatment by the man to whom Alexander and I were condemned to serve during the following weekend.

26 Alexander

Joshua's tale had only served to heighten my fear and James and I went down to Bentley's house in the country as required on the Friday evening full of fear and apprehension. Quite correctly, we assumed that Bentley was to use the occasion as a means of exacting the maltreatment that he has so much desired to give to us whilst at School.

Bentley's house stood on vast acreage and was totally secluded from any adjacent property. His liveried servants, all undoubtedly of a homo_s_e_x_ual disposition, greeted us cordially and, I suspect, with a degree of relief that we, rather than they, were to be the objects of their master's attentions during the weekend. The house was built in the style of a manor with vast staircases and large rooms. As our bags were taken to our rooms, James and I were led to a fine study in which a fire had been lit. There we found Bentley sitting in a winged armchair.

Bentley greeted us with obvious satisfaction and anticipation and, in accordance with the rules of the Society, required us to sign our acceptance of our punishment on a copy of the ruling that lay upon a fine oak desk. Having seen such documents before, James and I knew exactly what it contained and we duly executed the document thereby surrendering ourselves to Bentley's whims for the weekend until sundown on the Sunday evening. Bentley asked for the document and ensure that we had signed correctly and then directed us to repair to an upstairs bedrooms where, he informed us, suitable apparel would be awaiting us. When James indicated that we had brought sufficient garments for the brief stay, Bentley simply laughed and informed us that he was reasonably certain that we had not brought the sorts of garments that he required us to wear for the duration of our stay. Bentley instructed us that we should bathe and dress and then await his instructions.

More that a little fearful, we left Bentley and ascended the stairway where one of the servants showed us to the room where we were to bathe and then dress. I enquired as to the whereabouts of our bags and was politely informed that those things that we would require had been laid out in the room we were to occupy but that all other garments had been confiscated.

We entered the room that had been assigned to us and found, to our horror, that the only garment awaiting us was set of hose such as was warn nearly a century ago. Resigned to our fate, James and I each bathed in the adjacent bathroom in which a warm tub had been prepared and then dressed in the assigned garments, naked from the waist up and leaving absolutely nothing to the imagination. There we waited in sullen silence.

27 Bentley

James and Alexander had arrived promptly and I had sent them to their room to bathe and await my instructions. My servants were more than a little relieved to think that they might have a weekend during which my concerns might be focussed on my visitors and thus give them some respite from my close attention to their behaviour which normally required that one or more be punished at some stage during the weekend.

I sat in the library drinking and contemplating the angst that James and Alexander should have been experiencing upstairs, given their predicament. I took pleasure in knowing that the two delectable young men were at my disposal and reminisced about the way in which I had joined the Society and the wonders that it had beheld for me.

The Society was created shortly after James, Alexander and Joshua went up to Oxford and had been established as a club in which those so disposed might find a safe and accommodating means of pursuing corporal punishment as a discipline regime. Member from the higher classes of society were invited to join but members were not precluded from bringing with them servants from other classes of society to whom punishment might be delivered.

My membership was assured given my aristocratic lineage and my status as a former prefect and Head of House although, I suspect that some might have harboured a desire to exclude me. I had sought membership of this exclusive club that it might my career as well as provide an outlet for my disposition towards the administration of corporal punishment.

Having inherited my father's estate, with its large number of servants and indentured farmers, I had no end of choices as to whom I might take with me as companions to meetings of the Society. Although I was free to run the estate with an iron fist (and did so), there was far more pleasure in taking a young farmhand or footman to a Society meeting and there to have him chastised in public.

At first, the club had been largely without rules but quickly evolved into a quasi-judicial format in order that perceived excesses of brutality might be curbed. Some would say that my delivering some three dozen strokes to one young lad's backside for having caused me to have an accident in my newly acquired motor had provided a catalyst for the changes to the Society's rules. Despite the incident occurring late at night and my having been somewhat less than sober, any objective fellow would have seen my chastisement of the lad as being quite appropriate to the damaged caused.

Having flayed the youngster - a handsome lad of some sixteen years or so - James raised the question of the difference between cause and effect and out of the ensuing discussion came the appointment of a panel that would decide appropriate punishments. I was indeed called before this tribunal rather early on in the piece when a chum at Oxford mentioned at a meeting that I had severely dealt with one of my servants for having spilt some wine during a dinner party.

The party was a very private affair at which the younger servants were scantily clad that they might display their charms to the small number of guests who attended. The offending servant was a young man only slightly younger than I upon whom I had had my eye for some time. I will readily admit that my frustrated _s_e_x_ual proclivities with respect to young Giles had something to do with the manner with which I treated him when he spilt the wine but would claim in my defence that a bottle of 1885 Latour is no mere trifle and its being wasted justified the beating that the lad endured.

Notwithstanding, Joshua and James had assembled the tribunal to assess whether my treatment of Giles had been proportionate to his offence and I was judged to have been excessive in my use of force. As a consequence, I was demeaned by having to strip in front of the assembly, was locked into the pillory and there received some twenty strokes of the heavy cane. My posterior took many weeks to completely recover from that thrashing and it is with a certain amount of satisfaction that I now have James and his partner awaiting my attentions.

28 James

Alexander and I had been made to wait for quite some time before Bentley made his appearance. Condemned to servitude for two whole days, we agreed that we would not flinch in our determination to accept Bentley's undoubtedly vile actions without so much as a word of protest. When he entered the room in which we were placed and then came forward and ran his hands over our scantily clothed buttocks and our naked chests and backs, I realised, as I am sure did Alexander, the amount of determination our pact was going to require. I shivered as Bentley took his time feeling the strength of my arms and chest, my broad back and, inevitably, those areas covered by the skin tight hose.

As Bentley pawed at me and then at Alexander, he quietly chuckled at our plight and made clear his intentions of making the most of this opportunity. His lasciviousness became more pronounced as he examined us but finally the inspection ceased and we were invited to join him at dinner.

Somewhat to our consternation, Alexander and I were required to dine in the indiscreet clothing we had on and proceeded to the dining room in which a number of servants presided over the menial matter of serving us. From time to time I saw one or other of the servants ogling Alexander and myself and occasional a smirk passed across the face of the servants who were enjoying our obvious discomfort.

After dinner, Alexander and I were allowed to attend to our ablutions and then were required to report to what Bentley called "the chamber" at the rear of the large manor house. Alexander and I muttered quietly to each other as we steeled ourselves for whatever ordeal was before us and we were quite lost as we wandered the seemingly endless passages throughout the house trying to find the room in which we were to find Bentley. Finally, one of the servants spotted us and, with a knowing smirk on his face, led us directly to the room.

Bentley had changed his garments during the interregnum and was now dressed in a fine silk gown. His exposed chest suggested that he had little or nothing on underneath although his ankles showed that his lower half was dressed in some flimsy material. Bentley bade us enter and the first thing I noticed was the enormous size of the room and the large array of instruments and other paraphernalia that were spread throughout the room.

Bentley took hold of my arm and quickly led me to a set of shackles that were attached to an iron hook in the wall well above my head and quickly secured my wrists. I stood and watched as Bentley led Alexander to a block, fashioned after that at Eton, although this one was wider and had a number of leather straps anchored to its sides. Bentley ordered Alexander to set himself across the block and then proceeded to fastened the straps about Alexander's wrists. Next he pulled Alexander's left ankle to the extremity of the block and fastened it securely and then did the same to his right ankle. The hose that Alexander was wearing was stretched tightly between his nether cheeks and across is proud buttocks. Finally, with clear intent, Bentley secured the final strap about Alexander's midriff and pulled it as tightly as possible thus causing Alexander to expose his buttocks in the most obscene manner.

Bentley looked at me as if to gauge the displeasure or fear that I felt at seeing my partner so secured and chuckled as my anger showed as he caressed and patted Alexander's backside.

Alexander's head hung in a resigned manner as Bentley went to a table and carefully selected a three-tailed tawse with which he proposed to "warm you (Alexander) up a bit". As Bentley returned to administer the obvious thrashing to Alexander, he stopped in front of me and pulled down the front of my hose so that my genitals hung obscenely on display.

Bentley then proceeded to administer a severe beating to Alexander, covering his back, buttocks and thighs completely with bright red weals, occasionally looking in my direction and noting the growing prominence of my member that, despite my wishes to the contrary, seemed to have a mind of its own.

After such a severe beating just days before, Alexander's pain began to take voice and when Bentley took up a position straddling Alexander's torso and began laying the tawse in such a manner as to cause the middle tail to hit upon Alexander's readily available hole, Alexander started begging for mercy.

Despite the obvious pain that Alexander was experiencing, my organ would not subside and, finally, when Bentley ceased the beating, tore open the exposed part of Alexander's flimsy pants, unshackled me and led me to a position which placed my organ at the entrance to Alexander's rear, my appetite was all too obvious. Holding me back from entering, Bentley required that I keep the tip of my organ at the portal and then went to the other side of the room.

Suddenly, and seemingly out of nowhere I hear the unmistakable 'swish' of a cane and when it landed on my backside the sheer force propelled my organ deep within my lover's posterior. Simultaneously Alexander cried out at the rough intrusion and my weight against his severely beaten backside and I cried out as the pain of a clearly heavy cane exploded across my rear.

Bentley was clearly delighted with the effect and directed me to sodomise Alexander until I reached my climax. Knowing that I had no choice in the matter, I tried to accomplish my assigned (and not unpleasant) task as gently as possible but Bentley kept on swishing my backside each time I retreated with such force that the penetration was as brutal and forceful as anything Alexander might have anticipated. He cried loudly and I yelped as the cane struck and the effect unfortunately to prolong the process. By the time I had accomplished my task and released me seed deep within Alexander's bowels, my own posterior was throbbing as if a thousand bees were stinging it and tears were streaming down my face.

When Bentley released Alexander, my partner could barely move such was his pain and took quite some time to regain his feet and his composure.

29 Alexander

Bentley had beaten me into submission and beyond. It seemed to me that years of pent-up frustration on Bentley's part were being unleashed all at one and he showed no mercy. I knew that James would be excited by the spectacle as he had on previous occasions when I had been chastised but the brutality with which he rogered me was startling and incredibly painful. It was only after some minutes that I actually realised that James' actions were being driven by a severe caning and were not of his own volition. Nonetheless, the pain was excruciating.

As I collected my wits after the brutal treatment I had little strength and watched helplessly as Bentley took James and secured him over the end of a stout table and fiercely rammed his raging organ into the defenceless portal of my partner. Although James could not be considered inexperienced in such matters, the brutality of the assault cause him to cry out most horribly.

After seemingly hours of ill treatment, James and I were permitted to retreat to our room and were given some lotion to apply to our respective rears to alleviate the swelling and marked that the tawse and cane had left. James and I held hands and walked shakily upstairs. We lay side by side and took turns in applying the soothing ointment to each other's buttocks. We were in this position when a servant entered unannounced and presented us with a herbal beverage that, we were so informed, would assist us in sleeping.

James and I both took down the rather unpleasant draught and soon were falling into a calm sleep and were only vaguely conscious that the servant who had brought us our drink was taking considerable delight in fondling us most intimately as he continued to rub the ointment into our fiery backsides.


More stories by Jamie