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Sebastian's Schooldays

"Sebastian, an orphan, spends his schooldays in a strict boy's boarding school in upper New York."

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Author's Notes

"SEBASTIAN'S SCHOOLDAYS An Imaginary Homoerotic Story By Jason Land This is the first of a series of short stories each of which can be read as a stand-alone piece. However, as they are tied together by some of the characters, who, in one way and another, figure in several of these tales, I recommend my readers to read them in the order in which they were written which is as follows:- 1. <p> [ADVERT] </p>Sebastian's Schooldays 2. Sebastian Embraces His Sexuality 3. Sebastian – The Male Escort 4. Sebastian Meets Simon 5. Simon and Sebastian 6. Simon and Sebastian Meet Chris 7. Simon and Sebastian in San Francisco"

PART 1

PROLOGUE

My business card is very discrete. It says quite simply

Sebastian – Exclusive Male Escort
By appointment only
Telephone 100-123-4567

For those unfamiliar with the term Male Escort, let me explain. It is a euphemism for a man who copulates professionally for money with other men. He sells what is usually known as anal stimulation to his exclusively male clientele. And let me say, with no false modesty, that I am a consummate professional at my job and have, over a period of time, developed a faithful clientele who call upon me to ease their sexual problems. But I see that I am already getting ahead of myself, so let me stop here and start at the beginning, with the full story of how I came, quite by chance, to be in this business and where it has led me.

CHAPTER 1

My name is Sebastian Watson. Nothing special about that, you might think, other than the fact that the name Sebastian is not much used anymore today. But then none of my antediluvian names is much used any more as you can see when I tell you that my full name is a ponderous Sebastian Aloysius Mortimer Watson. Yes, indeed, I am a scion, to use their word, of what is considered in upper-class American society, again to use their words, an old family.

Old and good families, whatever they are, always seem to lumber their offspring with names that no normal person would ever think of using. Sebastian is bad enough, but I have come to accept it as I am always addressed as Sebastian and never, ever as Seb. But I ask you, Aloysius Mortimer; where on earth did my late parents ever dig up these antediluvian names? What on earth were they thinking about when they lumbered their only child with them? But that is precisely what old families do. But what the hell is an old family anyway – aren't all families old?

Well, I will tell you. An old family is one which has been rich enough or influential enough over the years as to keep track of its family history: who married whom and how many children and so on and so forth. And so, they are able to tell you that their line dates back to before the War of Independence or whenever. In fact, Joe Blow has just as long a lineage, but it had never been recorded and so, like most folks, he can barely go back much beyond his grandparents and rarely can he tell you the maiden name of either grandmother. That, my friends, is the only difference.

American tradition requires everyone to have, if not an actual middle name, at least a middle initial. It always asks for that on those official, printed forms one gets through the post.  So I decided to simplify things and call myself Sebastian David Watson: Sebastian D. Watson being my form-filling-in-name. What on earth would I have done otherwise, lumbered with two middle initials? The standard American form has space for only one letter: so people like me – and there are lots of us – just have to improvise, which is what I did. You can, you know, use any name you wish as long as you are not intent on committing a crime.

In my case, of course, coming from a true-blue old family I know that we have been around in Boston since 1720. My forebears did not come over on the Mayflower, but we count, nevertheless, as part of the Boston would-be-aristocracy. We Watsons may not qualify to socialize with the Cabots or the Lodges, (they are the ones, in case you had forgotten, who converse only with God) but we hold – or rather, held –  our own in Boston society, even though we never had the cash really to live up to it. Well, lumbered as I was with my prehistoric names, I was orphaned at the age of two, when both my parents were killed in a car crash and so I have no recollection of them.

We were a very small family. I was an only child as had been my mother. And my father had but one elder sister, Agatha Amelia Dorothea Watson (Oh yes, they did not stint on names, even for the girls!) who was fifteen years older than her brother and was a dried up, inward-looking old spinster: truly the quintessential Maiden Aunt. I am pretty sure the maiden bit was a correct designation, by the way, as she had no time for men at all and lived a solitary life, wrapped up in religion and good works, whatever they might be.

However, Aunt Agatha, as I subsequently called her, had that true sense of duty which goes with being from a good family and became my legal guardian from my earliest age. She was a totally remote woman who really had no time for children and engaged a series of nurses and governesses to look after me, until, at the tender age of eleven, she shipped me off to a boy's boarding school, the Sheldon Academy for Boys, which was located in a small community of the same name in rural upstate New York.

The Sheldon Academy was a private school catering for about 350 boys and attracted boys from those apocryphal good families for two reasons. Firstly, it promised a rigorous old-fashioned education modelled on that practised in English public schools; secondly, which was possibly more important in the eyes of many of the people sending their charges there, it offered supervised board and lodgings to the pupils out of term time. In other words, Sheldon was a place where, for a fee, you could enrol your offspring and not have to see them at all anymore, unless you wanted to until they reached the age of eighteen and left the school to pursue either a college education or find a job! So, Sheldon was not only a school, but it had a side activity as a sort of up-market orphanage for semi-abandoned children, to which group I numbered.

I exaggerate here somewhat, as even the most callous of parents or guardians felt it morally necessary to see their charges a few times during the year; but make no mistake, those of us who spent vacations at the school usually received but the odd visit from our parents or guardian, and only very rarely went home. In my case, I never ever went back to my Aunt Agatha's house (I cannot bring myself to call it home) until I left Sheldon aged eighteen and had to find a job. So, as you can see, from my entering Sheldon aged eleven and leaving aged eighteen plus, my school days were equivalent to a prison sentence, with no remission!

Aunt Agatha religiously came to see me four times a year (it was a sort of sacred duty) and took me out to lunch, for which as I discovered, much later in my life, she had paid for entirely out of my inheritance. But from the time I entered the school, aged eleven until the day I left aged eighteen, I never ever went back to Agatha's house! Incredible but true: but I was not the only one at Sheldon to be semi-abandoned. So, of home life, I had absolutely none. I lived in an expensive educational institution and had to make the best of it.

But it was not all bad, for I had some congenial schoolmates and overall, I was not unhappy: one just gets used to things and my thing was that Sheldon became, to all intents and purposes, my life. However, when I finally left Sheldon aged eighteen and a half, I had no clear idea what my future life would be.

CHAPTER 2
 
The Sheldon Academy was run by an expatriate Brit, who himself was a product of the old style English public school system. He had run this establishment on the same lines for over thirty years and saw himself as God incarnate, whose main object in life was to put fear into the hearts of his pupils. He came, apparently, from a very upper-upper, English background and rejoiced in the name of Ambrose Archibold Cedric Woodderowffe-Pryce - MA Cantab. (That's a master's degree from the University of Cambridge in England, in case you did not know).

Yes, you've got it. Incredible though it seems, that was his name: that ridiculous collection of double letters, which was pronounced, so he drilled into us, Woodruff-Priss. With typical English upper-class disdain for any pronunciation which bore even a vague resemblance to its spelling, even the simple name of Pryce –normally pronounced Price – was, according to him, pronounced as Priss.

Of course, Price, spelt with an I instead of a Y is a common enough name, but Woody's version was with a Y. The upper-class Brits are truly experts in the art of transmogrification! But I am sure you can imagine what we boys called him. There were two versions of his nickname: one was Woody Piss and the other Woody Prick. Once one had got to know the man better, Woody Prick was the one that stuck, as this character truly was a prick of the first water. Most of us lads referred to him, among ourselves, as the Prick, which led to the undoing of one of my closest friends; but more of that in due time.

Life at Sheldon was not all that bad. Some of the teachers were great and really enjoyed their jobs, which they saw as their true vocation. Others were just there to earn a living and were really indifferent about their work. One or two were downright awful in their treatment of their charges, among whom, a man called Clarence Simmons, who was the PT and games master, was easily the worst.

Slimy Simmons or just Slimy, really was a slimy little bastard, who loved to go around the gym classes, hitting his pupils across the arse with a short, leather strap he always carried. We guessed he had some special arrangement with the Prick as, according to the school rules, only the Headmaster was allowed to administer corporal punishment. But, somehow, Slimy managed to get away with slapping all and sundry with his strap during the gym lessons. And let me tell you that although I refer to it now as a slap, it really hurt! He was, moreover, an utter snitch and reported any misdemeanour, as he saw it, straight to the Prick. Even the slightest deviation from the rules was blown up by Slimy into a beating offence

Now, at this time, corporal punishment in schools had not been abolished in the USA; but it was rarely still used in the state schools. Not so with the Prick, who was running a private, fee-paying school. He was a great believer in the methods of what might be termed traditional or old school and was ready (too ready, many thought) to wield his cane across any miscreant's arse. The Prick was a real martinet with a strong sadistic streak and he seized upon even the most minor misdemeanour to thrash any errant pupil's naked backside.

Looking back on things now, I believe it was thrashing his pupils' naked arses that really made his day. Not a week went by but what some unfortunate lads had to drop their pants and let the Prick whack their naked butts. This happened at what the Prick called Punishment Parade, a concept he had somehow picked up from the British army cadet schools. Masters who felt a boy needed correction for some misdemeanour, filled in a punishment slip which the miscreant then handed to the school secretary, a dried up old trout called Miss Pimlott, who then produced the weekly list of those who were to attend punishment parade.

This was psychologically a horrible system, as instead of getting his arse beaten immediately, a boy who had received a slip, say on a Monday, had the mental agony of having to wait until Friday afternoon before receiving his punishment. All of us, I am sure, would have much preferred to take an immediate beating and get the thing over and done with. But that was not the way things worked at Sheldon. Come Friday afternoon there was usually a line of boys waiting at the door of the Headmaster's study to have their backsides warmed by his cane. Warmed, by the way, was an understatement, as boys usually emerged from the Prick's study, with their backsides on fire.

Another feature of these beating sessions was that Slimy Simmons always seemed to be in attendance to assist the Prick in his ministrations. And what made this whole ghastly system even worse, was the fact that Miss Pimlott made up the Friday punishment list on Thursday evening. Thus any boy receiving a punishment slip on a Friday was not on parade until the following Friday. Thus, the poor sod had the mental anguish of knowing that eight days hence he was going to have his arse thrashed. Talk about letting the lads stew in their own juice, at Sheldon, they literally drowned in it. What a dreadful system!

I now have to turn to my own development. By the time I was eighteen, I realised that my sexual orientation was towards other boys and that I really had little interest in girls – not that any of us had much opportunity to fraternise with members of the opposite sex; there just were not any girls around. But the fact of the matter is that, in spite of being a keen athlete and a regular use of the school gym, I was, at the end of the day, a very timid character. I told no one of my sexual orientation, although some of my classmates must have guessed, as I never entered into their interminable discussions about girls and what they might do with them given half a chance: an event which never materialised, of course, as there were no girls around.

As I mentioned earlier, I was a keen athlete and made regular use of the gym and its facilities beyond the usual physical training classes supervised by Slimy. There is no privacy at all for the boys in a private school such as Sheldon, run on the British lines. We all showered together every morning and evening as well as after every gym or sports session so that we were all totally accustomed to seeing each other naked. Cleanliness was certainly next to godliness at Sheldon – or was it the other way round? As time passed and we all moved towards manhood, it became increasingly evident that I was developing a more muscular body than any of my classmates; but even more noteworthy was that my cock was growing at an enormous rate.

By the time I was sixteen, I already had a seven-inch long cock of considerable girth. I knew that I was the secret envy of all my classmates and received, as well you might imagine, a lot of good-natured chivvying about the size of my tool; but I didn't mind as I was proud of my endowment. In fact, after I read somewhere the statement: On account of the respect which goes with sexual athleticism, most men are desirous of having a large penis, I realised that my classmates were green with envy Well at the time I read that remark, I was not actually a sexual athlete. In fact, to be quite clear, I had no experience of sex at all. However, it was a reassuring thought that I would not have to join the group in the desiring mode, as at the age of eighteen, I already had the physical attributes which might one day raise me to the level of a sexual athlete.

CHAPTER 3

On New Year's day 2010, my eighteenth birthday and in the middle of my final year at Sheldon, I made one single New Year's resolution: that I would find myself a sex-partner before the year was out, as I had the most urgent and pressing desire to have sex with another guy. Sex was, of course, a permanent topic among all of us, but in my particular case, with my extra large piece of meat between my legs, by the time my eighteenth birthday dawned, I had acknowledged to myself that fact that I was not like most of my classmates who were only interested in the opposite sex, and that I was probably homosexual.

More and more I was beset by the growing, urgent need to give physical expression to my feelings. When I looked at some of the better-built guys in my class, naked in the showers, I have to say that I could hardly restrain myself from keeping my hands of them. As boys of our age will do, we all jerked off regularly, but on the whole, there was no sexual contact between us. Wanking, as we called it, was just one of those things we all did from time, just to relieve what I now realise was the sense of sexual frustration that all guys of our age experience.

There was, of course, at Sheldon, no form of formal sex-education of any sort. It was an old style school, where I suppose that the staff somehow expected the facts of life would diffuse through to us by a process of osmosis. And so, as I am sure you can imagine, none of us was really sure of anything and there were endless discussions as to what men did with women, based upon bits of information picked up here and there.

This all changed when one of the more enterprising members of staff, the mathematics master, somehow persuaded the Prick that the school had to keep pace with the march of time and managed, somehow, to screw enough money out of the school endowment fund to set up a computer laboratory, where we all started to learn how to use this, to us, hitherto unknown piece of electronic knick-knackery.

This was truly a remarkable development for a school like Sheldon, which, in many ways, was still running much along the same lines as had English public schools at the beginning of the twentieth century, and here we now were at the end of the first decade of the twenty-first! Well, the upshot of this was that we all became very familiar with the Internet, for the laboratory was set up with Internet access. So, you can imagine what we all did. Very surreptitiously, of course,  we took every opportunity which presented itself to devour any pornographic site we could find. So the computer laboratory provided most of us with what, I guess, must pass for our sex-education.

We all rapidly became familiar with the true facts of life and, in my case, with that key homosexual act: anal intercourse, which knowledge I concealed from my schoolmates. I soon found out what gay men did together, whilst my classmates concentrated their research on finding out how a guy went about fucking a girl. Within a few weeks, we all thought that we knew everything about sex. And, with the brashness typical of youth, we gave no thought to the fact that experience might also have a role to play in our future sex lives.

Armed as I now was via the internet with the rudiments of homosexual-sex, my New Year's resolution to find a sex-partner became ever more urgent. Aged eighteen as I then was, I knew more than ever, that I wanted to have sex with another guy. I found looking at a pair of naked, young-male buns just so appealing that I just wanted to stick my cock up some guy's arse and fuck him as hard as I could. It may sound very crude and immediate, but that is exactly how I felt. But how was I to find this partner? I had no idea whether any of my classmates had the same gay sexual orientation as me and I really had no idea how to go about finding out if such a kindred spirit existed, without exposing myself to the potential ridicule of the other boys. But fate has a way of intervening in so many different aspects of our lives and came up with a solution.

After games, we all showered together and one afternoon, in late January, I found myself as the last person in the showers together with one of my classmates, a guy called Charles Tennant. Charlie was not one of my close friends but on this occasion, as we were drying ourselves off, we found ourselves quite alone, when he suddenly said to me, with his eyes glued on my cock, "You know Sebastian, you really are super well-equipped where it matters. Have you ever thought of giving your tool a little exercise, with another guy?"

That brutally direct question, as you might well imagine, stopped me dead in my tracks. Fully aware that I was being propositioned by Charlie, I decided to tread water for the moment.

"You know, Charlie, I am not sure what you are getting at," I replied.

"Come on, Sebastian, don't be coy. You know full well what some guys do to each other and I was just wondering if you might fancy a little adventure with me."

"Charlie, I'm not sure what you are suggesting."

"Oh, come on, Sebastian, for crying out loud, don't act so damned dumb. You must realise that I am asking you if you would like to fuck my butt, for as sure as hell I would really like to feel that cock of yours up my arse."

So, there it was. I had been unequivocally, and I might add, totally unexpectedly and brutally, been propositioned by Charlie Tennant, of whom I was not a close friend and who, until that moment, inasmuch as I had ever given the matter any thought, was to me, like my other classmates, a regular guy. I had no inkling of the fact that he might be of the same orientation as me. I realized then that this was possibly the very opportunity I had been hoping for: to find a guy with whom I could have sex.

However, before jumping in at the deep end, I said to Charlie: "What makes you think that I would ever want to do what you suggest? Why do you think that I might be that way inclined?"

"Listen," replied Charlie, "I have been watching you for some time now when we are all together chewing the fat about that inevitable topic: girls. I've noticed that whenever we get to the subject of the opposite sex and what we might do to them, well, you kind of fall off to the edge of the conversation. So I was wondering if you were gay, or possibly just wondering about your own sexuality. Look here, Sebastian, I will come straight out and tell you that I'm totally gay myself. I have had absolutely no personal experience of gay sex to date, but I have known for quite some time now that I am gay: a fact which I told no one until now."

"So you are the only guy to know about it. However, for crying out loud, please do not broadcast the fact. You truly are the only person to know my secret. So please, if I have got it all wrong about you, then please, please, please, don't let what I have told you go any further. So, now that you know, are you interested in…?"

Charlie tailed off here, leaving his question unasked; but as you all realize, he did not need to spell it out; he merely needed an answer and went on. "Come on, Sebastian, level with me, are you like me, gay? I was really hoping that you might be, as quite frankly, I have had the hots for you for quite some time now and would just love to take that cock of yours up my arse. It's just that until now, have never had a chance to talk turkey with you. So, there you have it: I cannot put it any plainer than that, can I?"

I paused for thought for a few moments before answering and then said, "You know, Charlie, it is really amazing that fate has thrown is together in this changing room today. You are dead right when you tag me as gay, and I have to say, I take my hat off to you. I had never ever thought of you as such. In fact, to be quite honest, and please don't feel insulted, but I had never ever given you much thought at all! Don't get me wrong. I did not and do not dislike you, but as we are both aware, we are not close friends: we are just classmates and that is that. How could I know about you, as you show no signs at all of your sexual preferences? But, my God, you have based your thoughts about me on the most superficial of observations and proved yourself right, but I had no idea at all about you until now."

Charlie went on: "So, now that we both know where we stand, that we are both in fact, gay – two gay young virgins together – how do you feel about my proposition? It would be a first time for both of us, as I have never taken another guy's cock up my arse and you have never fucked another guy either. So, here we are a pair of eighteen-year-old virgins. So, how about it? Shall we give it a tryout and see if sex is, in the event, all that it is regularly made out to be and, more importantly, to test the water about our own sexuality? As the old saying goes, the proof of the pudding is in the eating. So, what do you say? Shall we sample it?"

Well, what would your response to this invitation have been? Here I had been until a few minutes ago, wondering, for what had seemed like an age, how I could find a guy to fuck and now Charlie was handing me his arse on a plate and inviting me to shaft him; so, of course, I said yes. And to lay to rest any doubt about my own sexuality, I told Charlie, yet again that I was gay and that there was no doubt at all about that: it was a fact.

So, I said to Charlie that I was game to give it a whirl and then asked him when he thought that our first attempt at coupling should be. So there we were; exactly as Charlie had described us: a pair of eighteen-year-old, gay virgins, planning to take that first fatal step together. I say fatal step, for in the event it was to turn out for both of us to be our first liberating act in recognition of our true sexual orientation.

"As no one else is here right now, there is no time like the present," he replied, and before I could move, he had grabbed hold of me and started to kiss my nipples.

I have to say that I did not find this at all unpleasant even though it was the first time that I had ever been touched by another man, other than on the rugger field. And let's face it, being manhandled by other players in the middle of a rugger match, perhaps the roughest of all gentlemanly sports does not in my eyes qualify as a sexual experience. But, thanks to Charlie's mouth on my nipples, I could already feel my man-meat stirring between my legs.

Without saying another word, Charlie then dropped to his knees in front of me and took my rapidly hardening cock in his mouth and started sucking hard. Like many inexperienced guys, I could hardly control myself and started to exude pre-cum almost immediately. This was my first sexual contact with another guy.

Charlie, feeling that I had become fully hard, suddenly withdrew his mouth from my cock and said, "Quick, try and shaft me now, as I reckon you are ready."

Well, you can imagine how I felt. All this had happened at such an alarming speed, that I had really no idea what I should do or had I known what to do, how I should go about it. I had wanted to fuck some guy's butt for so long now, but all this was so very sudden that I was not in the least prepared for it. My Internet sex-education had taught me the rudiments, but now faced with the reality, I was almost in a panic.

Fortunately, Charlie had a clear practical bent, and leaned across a table which happened to be in the changing room, and spread his legs, to give me access to his anus. I had seen lots of lads naked many times before, but never had I had the opportunity to examine a guy's posterior anatomy in such detail and at such close quarters as was now offered to me.

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Looking at Charlie's hole it struck me how very small it seemed to be: no more than a slight pucker in the flesh and this, I guessed, was where I was supposed to stick my meat: it just did not look possible, for, by now, I was fully hard and sporting a cock with a considerable girth. I asked myself whether it would ever fit in what seemed a minute hole. In fact, it was not even a hole, but rather a dent; his anus was very, very tight indeed.

"What are you waiting for? Go ahead and shove your cock into my hole: that is exactly what I want you to do," came the exhortation from my partner.

"Charlie, it really does not look big enough for me to enter. It's just a small hole and my dick is now so thick that I doubt I will ever get it into you."

"Sebastian, you really are a dumb fuckhead! Surely you know that a guy's hole is closed by a powerful muscle called the anal sphincter, which is why it looks so small. Just push your knob against it and eventually, it will yield and you will be able to shaft me. Go on, just do it! We've agreed that we are going to try to fuck, so don't give up before we have even begun. Just force the tip of your dick hard against my hole and according to all I have read, it will yield and you will be able to shaft me with the full length of your meat."

"Apparently, it will hurt a bit for me; it always does the first few times a guy gets his arse reamed, but that is all supposed to be part of the experience. So, just press on and don't mind me I if moan a bit; don't fuck around; just bloody well do it. It's exactly what I want; what I have been dreaming about for months; so just do it; go on, stick it to me! Fuck me hard!"

I am sure that you will find me very naive when I say that I had not until that very moment ever even heard of the anal sphincter. Charlie was really much more conversant as to what was involved in anal sex than I then was. I guess I must have thought that I would just push my cock into a hole and that would be that. That would have to force my cock into my partner was something which I had not at all anticipated. Anyway, no one could doubt that with all the exhortations Charlie had just given me that he wanted me to fuck him, so I went ahead and did what he had asked.

As the knob of my cock – like most Americans of my generation I had been circumcised shortly after birth and so there was no foreskin hanging around to interfere with what, in the end, proved to be a smooth entry – touched  Charlie's anus, I felt the strong resistance that his sphincter muscle clearly presented to intrusion of a foreign body. Anyway, I pressed harder and felt the muscle begin to yield and the hole began to open, so I continued forcing my cock into Charlie until I had given him my full length.

I realized almost immediately that if we were going to do this regularly, we needed some form of lubrication to ease the contact between my cock and his rectum as it was all very dry and not very comfortable. This was confirmed as I started pumping for my cock, for it certainly did not slide smoothly in and out of Charlie's hole in the way I had seen it, times without number, on the Internet porn channels. Anyway, at Charlie's insistence I pressed on and it did not take me, as a beginner very long to reach a climax and I shot a huge wad of cum into Charlie.

On this, our first time together, I had no idea at all of trying to please Charlie and bring him to a climax simultaneously with my own. I simply bashed on and experienced the greatest orgasm I had ever had. That orgasm I had fucking Charlie's virgin arse, was, I saw, infinitely better than jerking off myself. The intensity of the sensation and the amount of cum I pumped into him were in another league to what I achieved wanking with the aid of my habitual, five-fingered lover. I really have no idea what Charlie experienced as I gave him his first taste of a cock up his arse. I don't think either of us expressed our feelings to each other, but somehow we both knew that we had to go on: this was not to be a one-off occasion.

 CHAPTER 4                                                
      
As Charlie said right at the start of our relationship, it was in our own interest to keep quiet and just get on with copulating: no boasting, no braggadocio, no talk about our activity at all. And, as he rightly pointed out, if Woody Prick, the Headmaster, ever found out about us, we would be in for the high jump; the old Prick would surely give our arses a monumental roasting with his cane.

And you can believe me when I tell you that this was an event to be avoided at all costs; my few earlier encounters with the Prick at his Punishment Parade as well as the occasional private beating of my naked arse, had taught me that however old and superannuated the Prick might appear, he still knew how to lay on the cane. Meetings with him were occasions better avoided. But did we, Charlie and I, manage to avoid that awful eventuality? No, of course, we did not, and it was all because of our own stupidity, which is how we each came to get the beating of a lifetime from the old Prick.

Charlie and I were again alone in the shower room. It was late one Saturday afternoon and we had both been working-out alone together in the gym. For some reason, Charlie who never ever looked less than attractive appeared to be even more so that afternoon, standing there, as he was, under the shower with his callipygian buttocks just so very, very inviting. My cock had already become rock hard just standing there looking at him and when I made the first move and forced my tool through his tight little sphincter; Charlie gave a sigh of pleasure as he took the full length of my meat inside him.  

"Give it to me really hard today, Sebastian; I really need it; I want you to fuck me with as much force as you can."  

So, I obliged him by serving his hole with the longest and most powerful strokes of my cock I could muster. Finally, arriving near my own climax, I withdrew my tool completely and prepared to give my partner the hardest thrust I could with the aim of reaching orgasm as I re-sank, for the last time, the full length of my tool into his arse.

However, at the precise moment, as I was preparing for my final thrust, a loud voice behind me said, "What on earth are you two boys doing?  Stop it immediately and get out of the shower.  In all my days as a schoolmaster, I have never ever seen anything like it."

I turned and found myself face to face with Slimy Simmons, who had entered the shower room unheard by us, due to the sound of the running water.  As I turned, I inadvertently added fuel to the anger which was clearly already raging in Slimy's head.  I could not stop myself climaxing and I had the misfortune to douse one of Slimy's shoes with a good dollop of my really thick sperm, which shot forth from my still hard tool in great gobbets as I repeatedly, and totally uncontrollably, ejaculated my pent-up load.  The stuff lodged on the toe of Slimy's shoe, glistening in all its pristine glory; my cum, that is, not his shoe!  Alas, this was a very unfortunate mishap, which did not improve matters.

After a slight pause, during which Slimy observed the state of his footwear and Charlie and I tried to compose ourselves, still standing under the running shower, Slimy repeated his question and asked us what on earth we thought we were doing.  Frankly, I thought it was a fucking, stupid question to ask, as a one-eyed, blind man could have seen what we were up to; but on the principle, the least said the soonest mended, we both kept quiet.

"Turn off that shower, dry yourself off and put back on your singlets and gym shorts, and, Watson, while you are at it, kindly wipe your emission off my shoe."

Slimy went outside and waited in the corridor while Charlie and I complied with his order. Slimy then marched us to the Headmaster's study.  The Prick was still at his desk, although it was by now past five o'clock on a Saturday afternoon.  Slimy bade us wait outside whilst he went in and informed the Prick of what he had just seen.  We were then called in to face the wrath of the Prick himself. Believe me when I tell you that what now followed was like a well-directed piece of theatre.

The Prick drew himself to his full height and adopted what I suppose was his wrath of god expression. He began, "Mr Simmons tells me that he has just found the two of you in the showers engaged in what I can best describe as an unnatural act." He intoned the words in italics, if that is possible, exactly as I have written them. "Let me tell you, boys, here and now, that such behaviour will not be tolerated for a moment in this establishment.  You two boys are guilty of gross moral turpitude, for which you will be severely punished.  There is no way in which I will allow such behaviour to continue, now that Mr Simmons has had the good fortune to see what you were doing and to bring it to my attention.  Neither of you will continue with your disgusting behaviour. I will nip the whole foul business in the bud right now and you will both cease such revolting practices forthwith."

As he paused for breath, I thought to myself what a silly old twit the Prick was. Nipping it in the bud was what he saw himself doing. Had he no idea that the whole relationship between Charlie and me was already in full swing so to speak; any buds which might have been nipped had long since opened and were now in full flower.  What it was quite clear that the Prick did not understand, was the fact that Charlie and I were both homosexuals, both now aged eighteen and indulging in homosexual anal sex, an act which all his prating would not stop us performing and which, at our age, was not illegal in the eyes of the law.  

Sex is such a great driving force; in fact, it is the greatest driving force in human or, for that matter, in animal or vegetable nature, and to think that you can stop it is like calling black white or acting like King Canute, who famously failed to stop the incoming tide.  This guy had no understanding of human nature at all, if he thought that whacking our arses, which was obviously what he was preparing to do, would in any way alter our behaviour, he was seriously mistaken.  

All we would both learn from what was clearly to be our forthcoming painful experience was to be more discreet in our activities; we certainly would not stop them.  I cursed myself inwardly for having shafted Charlie in the shower, allowing my cock rather than my head to dictate my actions. However, philosophically, it was a lesson learned, even if, as was to prove the case, it turned out to be a very painful one.

The Prick now resumed his oration and thundered on, sounding more and more like an Old Testament prophet as he warmed to his subject. Our behaviour was totally inexcusable and words like gross, moral turpitude and lewd, unnatural behaviour crept in more and more often into his diatribe.  And he then he came to the crux of the matter, the bit both he and Slimy had been clearly looking forward to. We would be punished, for our unseemly behaviour: indeed severely punished: indeed very severely punished. Having emphasised just how severe our punishment would now be if it ever happened again, then we would both be expelled: and on and on he went.  What a load of bullshit; he would no more expel us than jump off a cliff, for he would never give up the juicy fees paid by our respective parents.

So what was now going to happen? Well, it soon became obvious that the old Prick was enjoying the occasion and was determined to build the whole incident into a piece of drama, acted out with Slimy as a willing assistant. Looking back on it now, one could almost have believed that they had rehearsed their dialogue, which was couched in excessively polite and overdone phraseology.

"I think, Mr Simmons," boomed the Prick, "That the behaviour of these two boys calls for the severest punishment which the school rules allow."  

The Prick was Headmaster, but a Board of Governors had, long ago, drawn up a School Rules Book to which the Prick was evidently now going to make reference as if he already did not know what he intended to do us, which was to skin our arses. Slimy voiced his immediate agreement; yes indeed, such flagrant disobedience did most certainly call for the severest form of corporal punishment. As he said this, you could almost see him licking his lips in anticipation of the spectacle that he knew he would soon be witnessing.

And so now began a surrealistic, theatrical piece of dialogue between the Prick and Slimy, as if to demonstrate to the two of us how gentlemen conducted their affairs. It was almost as if the two of them had learned two parts in a play as it was difficult to believe that what followed was purely spontaneous.

"Mr Simmons," began the Prick, "I wonder if you would be so kind as to search in my bookcase for the red-bound book of School Rules and bring it to me here."

Until now, Slimy had simply stood to one side, listening – and clearly enjoying – the Headmaster berating us.

"Certainly, Headmaster, with pleasure." came the reply.

From the way Slimy emphasized the word pleasure, you could see that he really meant it. Anyway, Slimy then went over to the bookcase, found the book and made as if to hand it to the Headmaster, who, however, stopped him in his tracks and said, "Mr Simmons, perhaps I could prevail still further on your good nature and ask you to locate the page which deals with punishment of erring pupils and to read it out to our two delinquents here."  

So now we were delinquents! I am not at all sure that the word delinquent really applied to our behaviour.  We had been fucking each other and, I might add, that we were both aged eighteen at the time. Our behaviour might well not have been to everyone's taste, but in no way was it a crime.  But what was inadmissible to the Prick, was that we had been doing it whilst still at school and there were rules to be obeyed. The law of the land was one thing but here at Sheldon, the rules of the school applied. And I suppose in one way he was quite right to exert his authority, for, after all, he was acting in loco parentis. But one could see that he was salivating at the thought of thrashing two muscular backsides

Slimy began thumbing through the book, only to be interrupted by the Headmaster.
 
"Page forty-five, I seem to remember, the third paragraph."  

The old fart knew exactly, chapter and verse, what he wanted Slimy to read out to us.  

Slimy began to read. "Outrageous conduct by any pupil shall be corrected by administration of a severe dose of corporal chastisement.  The most outrageous offences such as, for example of a boy caught stealing or in flagrant breach of the school rules or caught in unnatural acts of moral turpitude  (there it was gain: moral turpitude, whatever that meant)  may be corrected by sound application of the cane to the boy's naked buttocks. The number of strokes shall not to exceed twenty-four on any one occasion and shall be left to the discretion of the Headmaster, who shall be the sole person to administer such punishment."  

So there in a nut-shell, you had it; the Prick was going to thrash the two of us. The only question was just how many strokes of the cane did we merit as a punishment for our disobedience.

"Well," continued the Prick, "You boys now see that the prescribed punishment to correct the the type of offence of which you are clearly guilty: flagrant breaking of the rules and gross moral turpitude, is a dose of corporal chastisement, which I shall have the greatest pleasure (and here he truly meant it) to visit upon your naked buttocks with my very best rod.  I have to say that in the old days, I would have happily given the two of you a good birching, but as that admiral implement has long been abandoned, I shall have to do my best with the rod; but a rod from the pickle bath it shall be and believe me you will rue the day when you ventured into the forbidden pastures of moral decay."

Where on earth did the old fart dig up such pompous English? Rod indeed, when what he really meant was the cane.  The way he was lecturing us went out at the end of the nineteenth century and here we were in the first decade of the twenty-first!

"Mr Simmons", he went on, "I hate to prevail yet again on your extreme good nature, but if it would not be too much trouble for you, I would be most grateful if you could go and seek out Mr Hickman (the school janitor and the Prick's general factotum, one of whose jobs was to maintain a supply of canes soaking in a bath of brine, as in Victorian times) and ask him to select for you three of the best seasoned rods from the brine bath, preferably specimens which have been maturing in the liquid for at least one month and bring them to me here."

"I would hate to think that these two boys do not receive their punishment with what I think one might best describe as the Rolls Royce of corrective implements: a rod in pickle: that splendid invention of our Victorian predecessors, which is, in my view, without any doubt, the best of all rods for administering corporal chastisement. "

"Oh yes indeed," replied Mr Simmons, "I fully agree with you, Headmaster, these boys really do deserve the very best and as you so rightly observe, and what could be better than a well pickled, flexible, rattan-rod?"  

And with that Slimy left on his mission seeking-out Mr Hickman and his selection of rattan-rods (!) soaking in brine.

You might as well have ordered Slimy to go and find a cat of nine tails if you really wanted the nec-plus-ultra of corporal punishment instruments, is what I thought.  What was abundantly evident was that Charlie and I were going to have our naked arses soundly thrashed and that there was nothing at all we could do to avoid it.  I vowed there and then to myself that never again would I allow would my cock be allowed to rule over my head. One lives and learns and the forthcoming lesson was shaping up to be a real humdinger, which there was nothing at all we could do to avoid!

The Prick now looked balefully at us and said: "Well boys, we should not be idle whilst Mr Simmons fetches the rods."

He made us move two chairs from against the wall and set them out down the middle of the floor so that there was enough space between each of them to allow him to address our arses correctly with his rod.  I should perhaps interject here that usually, the Prick thrashed those on his Friday Punishment Parade in a side room off his main study.  There, he had installed a beating horse, built by the faithful Mr Hickman, across which the errant pupil had to bend, offering his naked arse for punishment.  

Those on parade waited in his main study and were called in one by one to receive their punishment.  It was quite a gruesome experience as those waiting, for they could hear the sound of the cane – sorry I should say rod – as it mated with the present supplicant's arse.  But today, it was clear from what the Prick had told us to do, that he had something else in mind, which he now made clear.

"I think," he said, "That the time has come for each of you to assume the appropriate position for you to receive the corporal chastisement which you both so richly deserve and which I shall have no compunction in administering to your naked buttocks."    

What a wordy old fart he was. But, he had not yet finished, as he continued: "Many a Headmaster has observed to the errant pupil, that the punishment he was about to inflict on the miscreant youth would hurt him, the wielder of the rod, more than it would hurt the recipient himself. Well, let me tell you boys that I do not subscribe to this sentiment (neither did I!) as you are shortly to find out; for the pain, and believe me, the experience, which will be very painful, will be entirely felt by you! I, on the other hand, will know that I am carrying out my duty in correcting you, which in itself is reward enough."

"Now, both of you drop your gym shorts and present your naked buttocks to me for punishment.  Bend firmly across the back of the chair, as I want your buttocks presented high and tight so that I can correctly apply the rod to the greatest effect.  I am giving each of you a cork to bite on to help you bear the pain which you are shortly about to experience."  

So there we were, the two of us, each bent across a chair back, with our naked arses sticking up into the air and our cocks and balls dangling down below.  We must have been like that for at least ten minutes, waiting for Slimy to get back from his errand with the implements of torture.

When he finally appeared, the Prick said, "Well, Mr Simmons, as it is Saturday afternoon, you obviously have had some difficulty in finding Mr Hickman, but I see that with the perspicacity which is so characteristic of you, you have found the requisite rods, which I will now take from you."  Where did he get this Dickensian language from?

And with that, he took the three canes from Slimy and started to examine them to decide which one he was going to use to roast our arses.  He flexed and swished each in turn through the air and finally said that he thought one would do admirably.  

"I think, Mr Simmons," he said, "that we should explain to these to miscreants why the rod from the pickle bath is the most superior of all rods with which to administer corporal chastisement. I think it right and proper that they should know that they are to receive the very best that we can do for them.  Now, boys, as you may or may not be aware, the well known Newtonian equation, P=MF, admirably describes the dynamics of the act of corporal punishment.  P is the force or pain which will result from the mass M of the rod, decelerating at a rate F, when the rod lands on the target, in this case, your buttocks."

"Now, by soaking the rod in brine, one can effectively double its mass. So, as you can doubtless see, by this simple expedient one can double the pain. Additionally, the rod is rendered more flexible by the soaking and ensures the longest possible contact length with your buttocks. I think it always instructive for boys to learn something, even in such an unfortunate situation as the present, which is the reason why I am imparting this useful information to you now."

My god, what a wordy old fart the Prick was!  "Just get on with it," I thought. "Whack our arses and let's be done with it." But procedure reigned supreme.

"Mr Simmons, if you would again be kind enough to help me in this unpleasant task (the lying sod; he was relishing whacking our arses) and call out the number of strokes.  As this is the most a serious offence, I propose to administer the fifteen cuts of the rod to each boy."

"Certainly, Headmaster," came the reply, "It will give me great a pleasure to assist you in this matter and to see that these boys get their just deserts. I fully agree with you that their offence merits fifteen strokes, but let me add (the rotten, slimy, little sod!) that I consider fifteen strokes quite lenient in view of the maximum number of strokes allowed and the severity of the offence."  

And when he said with great pleasure, you could see that he really meant it: Slimy was an absolute sadist! What a slimy bastard Mr Simmons was; fawning as he was on the Headmaster; he was, metaphorically, practically pissing up the old boy's arse

Charlie and I had now been bent over our respective chairs for over fifteen minutes and I thought: "For crying out loud, get on with it and let's get it over with."  The Prick now flexed the cane, (or should I say rod?) and addressed my arse first.  He gave me a few gentle taps to decide where he proposed to place the first cut and then suddenly, with a force that belied his years, brought the cane down across my naked bum with such a crack that it knocked the breath out of me. For a split second, I felt nothing and then suddenly the enormous pain of the blow shot through my body and I wondered how I would ever stand fifteen such cuts.

"One," said Slimy.   

The Prick now turned his attention to Charlie and repeated the same procedure making poor Charlie cry out with the pain.  "Take your punishment like a man," boomed the Prick, whatever that was meant to mean, "And stop howling like a baby."

So that was the Prick's idea: he was going to give each of us one stroke at a time moving from one to the other, thereby dragging out the process.

And so it went on, blow after stinging blow, one for me and the next one for Charlie, with Slimy counting out the strokes.  The Prick paused for some seconds between each stroke so that we could each have time to appreciate the full excruciating pain each time the cane landed on our arses.  And all the time between strokes, as he moved from one to the other of us, he preached to us about our sinful ways and how we would surely emerge as better young men from the ordeal we were enduring.

So he went on until we had each received fifteen cuts, which he had expertly laid across our entire arses, which by this time our buttocks were covered with black and blue welts where the cane had landed.  Whatever we might think of him, it was a sure fact that the Prick was an expert with the cane. And I have to hand it to him in that he really knew how to apply the maximum of pain without breaking the skin.  Black and blue we both finished up; but, as we saw later, it was only bruising with no blood. But then, he had had some thirty-five years experience of beating butt!

Slimy had looked on lasciviously whilst we took our beating and it confirmed what I had always thought of him, that he was a sadist who found pleasure in watching someone else being punished. I could see that he had a hard-on and was in a pre-cum stage, as there was a damp patch on the crotch of his trousers. We finally got dressed, thanked the Headmaster for correcting us which was part of the protocol we had been taught to follow and, after a few more homilies from him, left.

Continued and concluded in Part 2

Published 
Written by jasonland
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