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.