Sebastian – The Male Escort – Part 1 of 6


Prologue My business card is very discrete. It says quite simply Sebastian – Male Escort Absolute Discretion Assured Telephone xxxxxxx For those unfamiliar with the term ‘Male Escort’, let me explain. It is a euphemism for a man who is a professional copulator, selling what is usually known as anal stimulation to his exclusively male clientele. Crudely put, a Male Escort is a man who fucks other men’s arses for money. 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 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. Well, it may become clearer if 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, to use again their words, ‘an old family’. Old and good families, whatever they are, always lumber their offspring with names that no normal person would ever think of using. Sebastian is bad enough, and 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 prehistoric names? What on earth were they thinking about when they lumbered their only child with them? But that is precisely what ‘old families’ do. 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 printed forms one gets through the post, I decided to simplify things and call myself Sebastian David Watson, or Sebastian D. Watson. 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 forbears did not come over on the Mayflower, but we count nevertheless as part of the Boston ‘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 to really 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 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 up-state New York. The Sheldon Academy was a private school catering for about 350 boys and attracted boys from ‘good families’ for two reasons. Firstly, it promised a rigorous old-fashioned education modelled on that practiced in English public schools, and 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, here was a place where, for a fee, you could enroll your offspring and not have to see them at all any more, 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! 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 the odd visit from our parents or guardian, but 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! I was one of these ‘lucky’ lads! 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, Aunt Agatha had paid for 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: and I was not the only one. So, of home life I had absolutely none: I lived in an expensive 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 was 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 istanbul escort establishment on the same lines for over thirty years and saw himself as a sort of God, 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, England, in case you did not know). Yes you’ve got it, that was his name, with 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, 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 were truly experts in the art of transmogrification! But I am sure you can image what we boys called him. There were two versions of his nick name; 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 really was a prick of the first water and most of us lads referred to him as ‘the Prick’, which led to the undoing of one of my close 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, Slimy we called him, who was the PT and games master and was easily the worst. This character was a slimy little bastard, who loved to go around the gym classes, hitting his pupils across the arse with a short 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 sneak and reported any misdemeanour as he saw it straight to the Prick. Now, at this time, corporal punishment in schools had not been abolished in the USA, but it was rarely 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 old school methods and was ready (too ready, many thought) to wield his cane across any miscreant’s arse. By the time I was sixteen I had had my arse whacked by him three times, but this was par for the course, for there was a regular stream of pupils entering his office for punishment on Friday afternoons. The Prick was a real martinet with a strong sadistic streak and he seized upon even the most minor misdemeanour to thrash the errant pupil’s arse. 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 poor 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 training schools. Masters who felt a boy needed correction for some misdemeanour, filled in a slip which the miscreant then handed to the school secretary, a dried up old trout called Miss Pimlott, who 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 with. But that was not the way things worked at Sheldon and come Friday afternoon there was usually a line of boys waiting at the door of the Headmaster’s study to have their backsides beaten. Another feature of these beating sessions was that Slimy always seemed to be in attendance to assist the Prick in his ministrations. I now have to turn to my own development. By the time I was seventeen I realized 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 around. I was, in fact, in spite of being a keen athlete and a regular use of the school gym, 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 materialized, 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 not great privacy for the pupils in a private school run on the British lines, and all of us showered together every morning and after every gym session so that we were all totally accustomed to seeing each other naked. 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 class mates. 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 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. Chapter 3 By a stroke of fate, I first saw the light of day on New Year’s day, so that January 1 st 2010 was my seventeenth birthday. I made but one birthday wish combined with 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 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 seventeenth birthday dawned, I had acknowledged to myself that fact that I was not like most of my class mates, interested in the opposite sex, and that I was a homosexual. More and more I was beset by the growing, urgent need to give outlet to my feelings. When I looked at some of the better built guys in my class, I could hardly restrain myself from keeping my hands of them, As boys of our age will do, we all jerked off istanbul escort bayan 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 realize 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 image, none of us was really sure of anything and there was 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 image what we all did, very surreptitiously, of course: we took every occasion to look at pornographic sites. 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, which I concealed from my school mates, with homosexual sex: 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. So, at least we thought that we now knew everything. With the brashness of youth, we gave no though to the fact that experience might also have role to play in our future sex lives. Armed as I now was with the rudiments of homosexual sex, my New Year’s resolution to find a sex partner became ever more urgent, for I now knew more than ever, that I wanted to have sex with another guy: I 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 class- mates had the same gay sexual orientation as myself and I really had no idea how to go about finding out, 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 in the changing rooms and one afternoon, in late January, I found myself as the last person in the showers together with one of my class mates, 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?” This 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. “Oh, come on, don’t be coy. You know full well what 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, don’t act so damned thick: you must realize that I am asking you if you would like to fuck my butt, for as sure as hell I would really like to feel your cock my arse.” So, there it was. I had 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 for me, like my other classmates, a regular guy. I had no inkling of the fact that he might be of the same orientation as myself. 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 our inevitable topic – sex, I’ve noticed that whenever we get to the subject of girls and what we might do to them, (not that there are any around to do anything with, I might add), well, you kind of fall off to the edges of the conversation. So I was wondering if you felt that you were gay, or possibly just wondering about your own sexuality. Look here, Sebastian, I will come straight out and tell you that I myself, totally gay. I have known this for quite some time now, but have told no one – but now you know. 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 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 your cock 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 gay. In fact, to be quite honest, 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 Escort istanbul 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, 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 I imagine you have never fucked another guy either: so here we are a pair of seventeen year-old virgins. How about it? Shall we give it a try out 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 eaten 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 out first attempt at coupling should be. “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 football field. I could already feel my man-meat stirring between my legs as Charlie dropped to his knees in front of me and took my rapidly hardening cock in his mouth and started sucking hard. Like many inexperience guys, I could hardly control myself and started to exude pre-cum almost immediately. Charlie, feeling this, suddenly withdrew my cock from his mouth and said, “Quick, try and shaft me now, as I reckon you are ready.” Well, you can imagine how I felt, as 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. 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. “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 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 piece. Apparently it hurts a bit for me, the first few times a guy gets his arse fucked, 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. Just bloody well do it. Don’t fuck around. It is exactly what I want, what I have been dreaming about for months. So just do it. Go on, stick it to me!” I am sure that you will find me very naive, when I say that I had not until that moment heard of the anal sphincter, so Charlie was really much more conversant as to what was involved in an anal fuck than I 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 myself 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 touched Charlie’s anus, I felt the strong resistance that this sphincter muscle clearly presented to intrusion of a foreign body, but I pressed harder and felt the muscle begin to yield and the hole begin to open, so I continued forcing my cock into Charlie until 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 the way I had seen it in 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, 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. Fucking Charlie, I saw, was infinitely better than jerking off myself: the intensity of the orgasm and the amount of cum I pumped were in another league to what I achieved via my 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 a one off occasion. Chapter 4 So, now you know how I started my sex life, aged just seventeen years old, with my partner of the same age. Charlie and I had sex two or three times a week for the next eighteen months until we finally left Sheldon in the summer of 2011. I do not know looking back on things, just now we managed to keep our relationship a secret, but no one ever suspected that he and I were fuck-buddies. 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.

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