Reminisences of a Headmaster 12


by Jamie <Woodthorne@csi.com>

18 The Headmaster

This process took forever but finally everyone resumed their seats. The nearest of the 'judges' looked mightily displeased with the outcome and somewhat concerned. Bentley and Clemens were sitting smugly, clearly content that they have won whatever the debate. His Lordship, having excused himself from proceedings during the debate, came to me and suggested that we retire from this assembly. I sensed that something untoward was afoot and declined the invitation, having been the cause of James' and Alexander's predicament.

Bentley stood and looked and James and Alexander and, with an evil glint in his eye announced that each young man was to receive one dozen strokes of the strap for having been deceitful in the past and a further dozen strokes of the cane for having brazenly pointed out their indiscretions to me. As a final indignity, both lads were directed to serve in Bancroft's service for a period of two days upon the following weekend.

While some of the company expressed satisfaction, even delight, at the sentence, James and Alexander were clearly shaken at the imposition and looked about for some relief from their predicament. James caught my eye. I could say nothing but tried to convey my sorrow for this appalling situation which I had caused to come about.

19 James' perspective

Hell, now that is something to shake one out of one's daydream! Never had I expected such an outcome. Even a birching would have been preferable. To apply a heavy cane to two backsides, swollen by a strapping is almost inhuman. Surely, I know that lads have had two dozen of the cane before, but this punishment is meant to obtain maximum effect and, to add insult to injury, Alexander and I have to serve Bancroft for an entire weekend. I knew where this is going. I glanced around seeking solace or even an appellant. Father looked grim and remorseful yet it was not his fault really. Alexander and his big mouth!

20 Alexander's viewpoint

James was in a state of shock and I feared that he would seek revenge for my stupid actions. He is less well equipped for this extreme punishment than I. _d_a_m_n_!

Sheepishly, James and I were guided over towards the flogging block and James was prepared for his punishment. Many gathered around. I think His Lordship had persuaded James' father to leave the proceedings. That was least is some consolation.

James looked quite delectable with his pale, naked posterior presented so prominently but his head was slumped and I know he was still shocked about what was to befall him. Joshua moved to his front and gently but firmly placed his hands on James' naked back and seemed to whisper something.

Clemens made his way through the throng carrying the dreaded strap which was purloined some years ago from a barber's shop. I had used this very instrument myself on other penitents and know how heavy it is, how well oiled and thus supple it will be and how, if used properly, how painful it can be. Clemens draped the strap over James' backside to let my love know of its presence. Clemens was clearly enjoying himself.

The first blow 'cracked' across James' backside with such ferocity that I think the heavy block moved a fraction of an inch as James' body reacted. James clenched his buttocks as the pain spread and tried to lift his torso but Joshua held him steady.

Clemens positively glowed in the light of the compliments that some of our company offered for the well-placed blow. He took his time and slowly delivered stroke after stroke as James gradually gave voice to his pain and cried out with increasing vigour. After eight strokes James' backside was clearly swelling from the thrashing and was a deep red in colour. He had reached that level of pain that his buttocks began to involuntarily clench and unclench as the waves of pain throbbed through his discoloured posterior.

Clemens slowly and deliberately placed the remaining strokes evenly over James' throbbing arse and ordered James to rise.

Unsteadily James eased himself off the block and clutched his swelling backside. Clemens pointed to the low pillory that stood nearby and directed two of our company to secure James in it in order that he might receive the allotted strokes of the cane in due course.

As he passed in front of me I can see that James had been reduced to tears. I didn't have time to think about how he would cope with the cane for Clemens invited me to assume the required position on the block. My knees went weak and I was not at all sure that I was ready for the punishment. Yet, given my position of responsibility in the Society and my sentence, I slowly disrobed and climbed over the ghastly place of execution.

Joshua placed his hands upon my shoulders and whispered that he tried to argue on our behalf. I was about to find out the extent of his lack of success on our behalves.

I shuddered as the strap was laid across my backside.

21 Joshua's recollection

I watched in fascinated horror as James was soundly thrashed and then placed in the pillory to await the savage caress of the cane. Then it was Alexander's turn. Despite the situation, I could feel my organ rising and filling as Alexander took his place on the block. His body, which I have come to know with a great deal of intimacy over time, was superb - strong and tough but hairless and glistening with that fine film of sweat that accompanies a dangerous environment. My hands, already a little wet from holding James down I then placed on Alexander's fine, broad back.

Alexander had had the strap before, of course, but this beating was slow and deliberately painful. Clemens used the strap with venom and attacked Alexander's proud buttocks with every intention of making Alexander suffer. Some of the strokes covered both of Alexander's cheeks while others placed the end of the strap well into the crevice between the two. These particular strokes brought forth a screech of pain from the otherwise stoical Alexander and his nether cheeks opened briefly to reveal his inner sanctuary for which Clemens was clearly aiming.

By the time Alexander had received his twelve strokes from the strap and I can move about to see the damage, his buttocks were deep red and clearly swelling from the treatment they had received.

To my relief, James had regained his composure whilst he had been confined in the pillory for there is nothing worse than to see such a beautiful creature so distressed as he has been when he had been thrashed. Knowing James as I do, I surmise that the brutal chastisement of Alexander had reminded James that he was not alone in his suffering.

The skin on James' posterior was swollen and seemed ready to break apart. Bentley was given the "duty" of applying the cane and strode forward towards his first victim.

I go to where Alexander had been left on the block and patted him on the back in a meek effort to offer consolation. He looked at me and there were tears in his eyes which he used the back of his hand to wipe away. His weak smile was encouraging but disappeared quickly as the first 'swish' of the cane and the first 'crack' as it met James' backside brought us back us to the reality of the moment.

Looking over Alexander's prone body I could only see the back of the throng that milled about watching James' torment.

Apart from the occasional expletive, James did not give anyone the satisfaction of knowing how fearfully painful was his caning. I arose and pushed my way through the crowd and arrived as Bentley delivered the final stroke. James' swollen backside was very neatly striped from top to bottom and a little blood trickled from a couple of wounds but, manfully, he had not allowed his legs to betray him and was extraordinarily self composed.

I asked two of the more junior members of our set to proceed to release James and escort him upstairs to one of the vacant bedrooms and to stand guard to make sure that no-one took advantage of his circumstances. I advised that I would bring Alexander along in due course.

As James made his exit, Bentley licked his lips and summonsed Alexander who, courageously, raised himself from the block and walked calmly to the pillory and placed his neck and wrists into position so that he might be fastened. I watched as Alexander approached. I was astonished that his gait does not show any sign of the pain that must have been throbbing in his backside and his organ was somewhat aroused, but not obscenely so. There was no bravado in Alexander's behaviour but, rather, a steely determination to take his punishment like the man that he is.

Bentley laid on the strokes with a will and spared no effort in trying to elicit some expression of pain from his victim. Alexander held out until Bentley slashed the cane across the tender flesh where buttocks join thighs and Alexander yelped. Bentley smirked with satisfaction and proceeded to lash that small area of Alexander with the desired effect.

22 James

I could not believe the carnage wrought upon my backside. Even at School the thrashing and beatings were no where near as painful and those that I have received since School, whilst memorable, do not compare with the agony that throbbed through my backside that evening.

While I knew that Alexander was going through the same procedure, I was frightfully angry with my lover and his big mouth and was determined to exact revenge once I was in a condition to roger him well and truly.

Joshua brought Alexander into the room where I was lying on my stomach, my backside slowly subsiding into a constant deep throbbing. Alexander has clearly not suffered as much as I for, although his backside was severely damaged, he walked with a minimum appearance of discomfort. Joshua set Alexander upon the bed beside me and then rubbed some lotion onto my aching rear.

Next door we could hear the sounds of the previously punished lads being sodomised, apparently with a great deal of vigour given the noise of the bed heads banging against the walls and the cries from the victims.

I listened to the sounds as Joshua gently tried to rub some of the pain away and, when he had finished, I reached out to him and gave him a kiss of gratitude. Next I smacked my hand down with full force upon Alexander's burning backside, to which he responded with an apology for his stupidity. I then dressed and was assisted by Joshua to descend the stairs where I bade goodnight to those still assembled and departed as gracefully as possible.

I knew not at what hour Alexander returned for I took a small dram of laudanum and quickly fell into a deep sleep.

Alexander was beside me when I woke in the small hours of the morning. He was sleeping on his stomach and I pulled back the blanket and sheet and examined the damage to his posterior. The weals were wicked and, although I knew that my own rear would display equal damage, I took pity on my partner and gently kissed him. Sleep overtook me and when I next awoke, Alexander was lying in much the same position looking at me.

I must acknowledge mixed emotions at that instant that we made eye contact. My heart told me that he was the most precious person in my life but my rear told me that I should properly be angry at him. I stroked his welted backside and discussed with him my love and my anger.

23 Alexander

Joshua arranged for me to get home and there I found James soundly asleep. I took some port to help me sleep and then went to bed. During the night I had a strange dream about James soothing my throbbing backside and even kissing me. When morning dawned I was awake and just lay in bed watching James who I had betrayed with my foolish mouth. Suddenly, James opened his eyes and I saw a mixture of emotion in his eyes. While he reassured me of his love, he also told me of his anger about my foolishness and I explained to him that I understood and accepted his judgement on the matter.

Sometime later we bathed and rubbed each other with lotions to ease the pain and to assist the healing of the wounds on our respective backsides. As always, we shaves each other's cleft since neither of us liked any hair there. It was then that James started to exact his revenge for my stupidity. Turning towards him, James lathered up my pubic regions and proceeded to shave away all the hair in that part of my body. I was both excited as he grasped me but also ashamed at being subjected to the indignity.

When James had completed his activities he trotted off saying that the shaving was only a part of the punishment he was determined to exact for my indiscretion.

By the time I was dressed, James and his father were breakfasting. I joined them and sat in silence as they discussed everything other than the events of the previous evening. James was quite stiff in his movements as the pain in his rear clearly was still omnipresent (as it was in mine).

After breakfast, James and I talked about the other part of our punishment: the requirement that we serve Bancroft at his estate the following weekend. James and I knew that Bancroft was going to exact full measure from us for our 'crimes'.

At mid morning, Joshua arrived to see how we were faring and we shared our concerns with him.

24 Joshua

James and Alexander were at least on speaking terms and were in deep conversation when my presence was announced. Jointly they expressed their concerns about the following weekend when they would have to put themselves at Bancroft's disposal. While I understood their apprehension, I reminded them of our past and the fact that I had been a novice at the time when Bancroft had taken my innocence away. I reminded them that I was much younger than they were now, what had transpired, and how well equipped they were to deal with Bancroft's notorious ways.

I reminded them that, when Phillips' spying had finally caught us out in the glade beyond the Headmaster's house, that their positions of privilege had protected them from the full ferocity of Bentley's wrath and that it was I who took the full brunt of his professed anger.

25 Alexander

Joshua's tale reminded me how fortunate James and I had been when we were caught by Bentley. Phillips, as we soon found out, had been the spy and had reported to Bentley that we three were engaging in _s_e_x_ual depravity. While a bit of sucking, kissing and the occasional finger up an arse might be considered indiscrete or even "improper' but there was nothing depraved about our activities.

When we were confronted with the allegations by Bentley, we all knew that we had to act honourably and admit to some impropriety. Imperiously, Bentley received our explanation for what had been seen and decided (apparently) reluctantly to acknowledge that his information might be somewhat tainted and thus he reserved his _s_e_x_ual aggression for Joshua rather than James or myself.

James and I received a fearful beating across our naked backsides but, as we came to find our that evening, Joshua fared far less well than we.

In recanting his tale, Joshua made me feel somewhat ashamed for my fear as to what servitude to Bentley might entail, for Joshua had been considerably younger when he incurred Bentley's wrath.

Bentley, as Joshua reminded us, had ordered the lad to remove all his clothes before the beating began. Naked, Joshua had trembled at his vulnerability and had then to accept eight, rather than the six strokes of the cane that James and I had endured. Rubbing his buttocks furiously to ease the pain, Bentley had then advised Joshua that he was to receive a further thrashing because he was judged to have led James and myself "astray". If ever there was an injustice, that was the moment for James and I had both encouraged Joshua to join with us in our exploration of our _s_e_x_uality. "Oscar Wilde and all that" we had told Joshua "is no concern of ours since we are school chums and have not sought out strangers for our satisfaction".

Joshua had caved into Bentley's threat of a further beating and, knowing of Bentley's reputation as a bugger, pleaded with him to find another way of punishing Joshua rather than further strokes of the cane.

Joshua had told us that night, as we cleaned his nether regions of the blood and muck that seeped out of his ravaged hole, how Bentley had simply pushed the lad over the side of his desk and brutally, without preparation, had ravaged Joshua's arse with his rampant member. James and I winced at the simple thought of such an encounter given that we both had seen Bentley from time to time at the baths beside the football pitch and had a reasonable knowledge as to what length and girth swung between his legs. That Joshua should loose his virginity in such a manner was deplorable.


More stories by Jamie