A Male Escort by Accident

by Jason Land

10 Apr 2018 10594 readers Score 8.6 (24 votes) PDF Mobi ePub Txt


A Male Escort by Accident

An Erotic Short Story

by 

Jason Land  

CHAPTER 1

Hi guys; my name is Jeremy; I’m a Chicagoan and I’m what is euphemistically called a Male Escort.  Any guy who does not go around with his head in the sand knows more or less what I do when they hear that I am a Male Escort, but frankly I don’t know where that expression comes from, for escorting, which implies accompanying someone somewhere, usually with some notion of purpose or protection, is, of course, the very last thing that a Male Escort does; well, speaking for myself, it’s something I never do; but I suppose that there are Male Escorts and Male Escorts.  So to be quite clear where my particular Male Escorting abilities lie and to call spade a spade, my job consists of providing my male clientele with what are usually politely referred to – mealy-mouthed again – as stimulation and discipline.  So yes; as you can see reading between the lines, I have two strings to my bow; I am willing to stimulate a guy, not by engaging him in a scintillating conversation, but sexually by what is usually referred to politely as anal stimulation; this is another euphemism to avoid the crude harsh fact which is that I fuck his arse if that is what he wants.  

But when it comes to discipline, I have some masochistic clients who use my services uniquely to provide them with what is usually referred to as CCPConsensual Corporal Punishment: in a word I thrash their arses; usually naked or on the bare as it was called at my English public school; but the client is king and so I do what he requests of me with a variety of implements according to his individual preference without indulging in any sexual activity at all with them. And finally I have my favourite type of client, who wants me first to shred his arse with a cane or whip or whatever and then go on to fuck him.  This is what I think of as the full enchilada and I just love it. In fact, I love all aspects of my work as the mere thought of both anal sex and corporal punishment turn me on sexually. At the end of the day, sex is the one human activity which never fails to please; at least that is the way it seems to me as I never tire of it; either professionally or socially or any other way.

I suppose my intense desire for gay sex is tantamount to an addiction; like those drug addicts, who once hooked cannot do without their daily fix; well so it so it is with sex and me; I cannot do without it; I am an addict! But what a marvellous addiction it is, for it always gives me great pleasure and equally does no harm to anyone.  To be quite clear, I never force myself on anyone, so I have to believe that my passive partners, whether regular or casual, enjoy what we do together just as much as I do. In fact, I did not become a Male Escort by design; I just sort of slipped into the profession – if profession is – by accident, in spite of my own initial misgivings as to what I had, on a couple of occasions been inveigled into doing. Anyway, as you will learn, I did subsequently  become what I am today – a Male Escort – and I really do enjoy my present life.

But I am sure that the astute reader of this story will have noticed that I, a Chicagoan, and an American by birth, refer to a client’s arse and not his ass.  Well the former is the vulgar word that the Brits use crudely to describe a guy’s posterior whilst the latter word is the American equivalent for that same part of his anatomy, but which for the Brits implies a donkey-like animal, the ass and as such does not capture their sexual imagination. So how come then, that I, essentially in all that matters the quintessential, all American Mid-Westerner, use the English word to describe the object which takes up so much of my attention? Well, the fact of the matter is that I am actually half English, born in the USA to an English father and a Bostonian American mother, who traced her lineage back into the mists of time when everyone in the then Un-United States was of British extraction. And so having been born on American soil, I am by nationality an American citizen. But my immigrant father, who himself became a naturalised American citizen, also went and registered my birth at the British Embassy; so I enjoy dual nationality: American and British.

How my parents came to settle in Chicago, a city of which my Bostonian mother totally disapproved, is a long and uninteresting story with which I will not burden you. Suffice it to say that my father became the CEO – for British readers of this narrative, the Managing Director – of a large conglomerate and, over a period of years, thanks to the exaggerated salaries which such firms pay their top people, became a very rich man.  And so, money counting for something, even though it was not the old money my mother clearly would have liked it to have been, she made a sniffy if a nevertheless somewhat-disapproving best of the luxurious lifestyle which my father’s income allowed us to lead in Chicago. We lived in a spacious upper floor apartment the lakeside road called Lakeshore Drive just north of Chicago downtown centre, known locally as the Loop. In realtor – that’s an estate agent in British English-speak – our apartment enjoyed uninterrupted views over Lake Michigan.  Speaking for myself, I find looking over a large expanse of water utterly boring; but that is just my personal view.

And so, as I grew up, in common with other boys of similar wealthy backgrounds to me, I was sent first to a private local day-school and then from the age of about nine, at my mother’s insistence, was shipped off back east to an upmarket boy’s preparatory school in the Boston area, where I was, of course, a boarder.  I never really worked out whether my mother wanted me to have a true, blue-blooded, snobby, Bostonian-type education or whether she just wanted me from under her feet. Not to put too fine a point on it, my mother and I were not terribly close; if I tell you that from an early age I always called her mother and never mom that will give you an idea of the level of intimacy that I enjoyed with her. Anyway I actually quite liked being at a boarding school even though things were much stricter than they had been at my day school back in Chicago.

It was at this school that I first encountered the doubtful joys of corporal punishment in the form of a well-paddled bottom – I had not become conversant with the word ass at that stage in my life – which was dispensed by the school principal to correct – don’t you just love that word? – any and every misdemeanour, both real and imaginary.  As this was a traditional old-style school, the paddle was suitably drilled with holes to make sure that it mated correctly with its target, which was always the offender’s bottom.  Visits to the principal’s office were for me, frequent and painful; for Mr. Carter, as he was called, was an absolute expert in the paddling of his charges; an act which he carried out with monotonous regularity and always with considerable vigour.  And so by the age of about twelve or thirteen when my time at prep school came to an end, I was already all too familiar with the pleasure associated with a sore ass – which vulgarity we had all, by that age, adopted. It’s quite amazing how quickly even well-brought-up lads such as I, pick up and use the vulgarities so common at even the best of schools  and then bring them out purposely to shock their parents. Oh and I see that I forget to mention that the paddlings were always applied to the seat of the miscreant’s pants.

Well I suppose I might as well come clean and tell you that Jeremy is not actually my real name, but just the name I use professionally as a Male Escort.  My true name is Andrew David Stevens and it was as such that at the age of thirteen that my father decided that I needed a rigorous English Public-School education.  The Brits have a remarkable aptitude for confusing things, so that a public school, contrary to what its name implies, is a private establishment where rich, usually upper-class Brits, pay exorbitantly high fees to ensure that their offspring get what is, in their view, a proper education and learn good manners.  The schools that the vast majority of English kids are forced by law to attend are known as State Schools, which may or may not have some religious affiliation attached to them.

My father himself was from the north of England where he had been born and spent his early life in a small town in the East Riding of Yorkshire, the largest of all English counties, which, like ancient Gaul, was divided into into three parts called Ridings.  His father, my grandfather, was a well-to-do gentleman farmer and had sent his son to a prestigious public school, Frogmore Academy for Boys, located in a village the same name near the county town of York.  This had been the place where all male Stevens’ offspring, going back into the mid-nineteenth century, had been educated and was where, shortly after my thirteenth birthday, I arrived in September for the start of the new school year. I was not completely abandoned in being sent there as my paternal grandparents were still alive and lived not far away. I might as well just add here that of my maternal grandparents, only my grandmother survived and as she lived in what I supposed was isolated splendour in the old family house in Boston. In fact, I barely remember seeing her; certainly she never ventured into the uncouth mid-west where her only child, my mother, was now living.

But equally I hardly knew my English grandparents as for some, to me at least, undefined reason, my father’s relationship with his parents was, to say the least; distant. They however, they were delighted to have their only grandson – my father was their only child and I too had no siblings – in relatively close proximity when they learned that I would be schooled at Frogmore. It had been agreed between my father and his parents that I would spend all the shorter school vacations with them and go back to Chicago only for the long summer vacation each year. So as you can see, having been packed off at an early age to a boarding school in the east and then shipped off to public school in England aged thirteen, my relationship with my parents became ever more distant. Apart from forking out the cash to pay for my education, they did little else for me in my formative years; in a word, the much vaunted parental guidance and influence were non-existent.  So my parents and I were never very close, even when I was just a boy.

Frogmore or Flog-More as it was known cynically to the inmates – sorry I mean pupils, of course – was an old style school, where the cane and birch reigned supreme.  In fact for a school in the twentieth century it really was a very old style school, where to all intents and purposes nothing much had changed since the Victorian age. It suddenly hit me years later that the school was still ploughing the traditional furrow designed to turn out well-educated, upper-class young gentlemen many of whom would then go on to run the British Empire. Unfortunately the powers that be behind this system, admiral and fit for purpose though it might have been in the past, seemed oblivious of the fact that the Empire no longer existed. The school comprised a group of magnificent period buildings of which, being a naïve, and by British standards, gauche and brash American, I had no aesthetic appreciation whatsoever at the time of my internment – sorry I mean enrolment – as a pupil there. Like most public schools where boys are boarders, Frogmore was divided into a number of houses, to one of which each boy was affiliated and became a permanent member for his entire career at the school. At Frogmore there were six houses in all, each of some eighty or so boys, ranging for new boys like me through to upper-sixth-formers in their final year at the school. But total loyalty to your house was expected and any act by a boy which in anyway disparaged his house was a cause for immediate punishment by the House Captain or one of his acolyte co-prefects.

I won’t burden you with the fine details, but the houses at Frogmore were named after six of the royal dynasties which had at some time ruled the country.  My own house was called Hanover, of which my father and grandfather had, in their day, also been members.  And I was not alone to have this family affiliation, for many boys at the school were like me and had forebears who had been educated there and automatically became members of their traditional family house. But Frogmore, alone among English public schools, had a unique prefect tradition in that there were two junior and two senior prefects per house each reporting directly to the Housemaster, who was usually a bachelor: a younger member of the teaching staff, who himself lived in the house.  The junior prefects were named each year from boys in the lower sixth and then in their final year graduated to become seniors, one of who was nominated by his Housemaster to be House-Captain.

The Head-Boy of the school who had powers virtually equivalent to a master – and I might add, tended to use them to the full – was nominated by the Headmaster himself and was traditionally one of the senior prefects. At that stage in the final year of his school career, the Head-Boy became the only pupil of the school not affiliated to a specific house and moved into what was, for a pupil, by any standards, a spacious suite of rooms in the main school building, located just along the corridor from the Headmaster’s study.  So the house from which he left to become Head-Boy, found itself with two junior and only one senior prefect for that year. The reason I am telling you all this is that all the prefects, juniors and seniors alike, plus the Head-Boy were allowed to correct – always with the cane and always on the bare arse – any and all of the pupils at the school; a task which they for the most part readily adopted; usually with considerable enthusiasm. Add to this that each of the six Housemasters were also devoted users of the cane and the fact that the Headmaster too did not deprive himself of the pleasure of beating boys’ arses when he saw the need, those of you readers who are mathematically minded will see that no less than thirty-one individuals at Frogmore were regular practitioners of the not-so-gentle art of corporal punishment; and in the main, they were jolly good at it!

CHAPTER 2

But as befitted a structured establishment such as Frogmore, all cane wielding arms were not equal and there were strict rules as to who could do what when it came to applying the cane.  It was all based on the fact that the school Governors had decreed that the maximum number of strokes of either the cane or the birch, which latter was used exclusively by the Headmaster, was twenty-four cuts on any one occasion.  So the Headmaster alone cherished – and I choose the word carefully – the privilege of being able to deliver twenty four strokes, which according to rumour he regularly did; in fact, he rarely did, but when he did, as I only once found out to my cost, it really was something else.  The six Housemasters and the Head-Boy were limited to eighteen strokes of the cane, whilst the senior prefects had to satisfy their often, all-too-obvious,  sadistic streaks with only twelve strokes, with the junior prefects being limited to a parsimonious allocation six strokes only; and then only with a junior cane and on the boys of the first and second forms.

However, where there’s a will there’s a way, as the old adage goes; so that even limited to only six cuts with a junior cane, most of the junior prefects managed to inflict considerable pain on the lads of the first and second years whom they enthusiastically thrashed whenever the opportunity presented itself.  And when opportunities were in short supply, the junior prefects showed considerable resourcefulness in inventing some.  But of course exceptions were made to these rules as both the Housemasters and especially the Head-Boy occasionally petitioned the Headmaster for a derogation of their limit if they felt a boy deserved a stiffer dose of punishments to help him repent of his sins. And it has to be said that the Headmaster, who was a staunch believer in the beneficial effects of beating a boy’s arse, very often gave his permission. I often thought that the so-called beneficial effects were really felt by the prefects who in wielding he cane, were allowed to exercise their hidden sadistic tendencies to the full. I never knew a prefect who did not enjoy thrashing his schoolmates’ arses nor a boy, being thus thrashed, who felt that he had benefitted from his beating.

So Frogmore was a place where any boy’s backside was in more or less permanent danger from an assault with the cane, which I suppose is how the place came to get its very apposite nick-name: Flog-More. You will have noticed that no mention has been made of the teaching staff and their involvement in what might be described as the corporal punishment stakes at Frogmore.  In fact, many of these masters were somewhat disgruntled by the way they were excluded from the beating brigade: those who were authorised to use the cane. To their disgust, they were totally forbidden to wield the dreaded rod of correction on the arses of their pupils for offenses committed in class and had to content themselves with handing out punishment slips, in much the same way as traffic-cops hand out citations for traffic violations, which give rise to what a cynic might describe as riches in heaven, in the form of a later punishment: a beating for Frogmorians or a fine for traffic violators. In both cases, the recipient of the citation had the mental anguish of having to wait for his punishment. 

At Frogmore, the Headmaster and the Head-Boy dealt jointly with the in-class miscreants immediately after supper on Monday, Wednesday and Friday evenings at which times groups of lads could been observed standing outside one of the two study doors waiting to be called in to face the music. This was essentially a vocally-punctuated, percussion piece centred on the boy’s arse; the music, if it can be called such, was played by either the Headmaster or the Head-Boy with a vigorously applied rattan cane and sometimes the birch; whilst the unfortunate recipient of these ministrations was free to emit howls of painful appreciation as the cane descended with its rhythmic regularity, creating a set of welts reminiscent of the bar lines of a musical score on the poor sod’s naked arse.  Connoisseurs who were regulars at the thrice weekly performances, claimed that they could tell which cane was being used by the pitcjof the swish as it descended through the  air and distinctive crack it made as it mated with the naked arse of the victim; but that was probably apocryphal. 

But what might best be called a feature of the flagellation stakes at Frogmore, were the clothes in which boys summoned for punishment by either the Headmaster or the Head-Boy were obliged to present themselves for punishment.  They were known as the appropriate attire, an appellation which some past Head-Master had given to the skimpy clothing in which he expected boys to present themselves to him. It consisted of a pair of gym shorts, a gym vest and a pair of bedroom slippers and nothing else! You could easily see the sense of it, as the poor lad who was to be whacked entered the study, dropped his shorts and bent across the back of a chair and presented his bare arse to either the Headmaster or the Head-Boy for their percussive ministrations. Henry Ford or any time-and-motion expert would have been proud to have thought up the idea as it greatly increased the throughput of arses which could be beaten in a given period. And it avoided totally the inevitable fumbling associated with making a boy take of his shoes, blazer, trousers and underpants to gain access to his backside, which at Frogmore, as in many other public schools, was always beaten naked; in  public-school speak he was always beaten on the bare.

On the same corridor as the two fatidic studies, there was a spare room which had been designated as a changing room. So boys slated for the cane, first went there ahead of the witching hour at which arses and canes were destined to conduct their painful tryst, changed out of their day clothes into the appropriate attire; they then went and stood in the corridor at the appropriate door and waited to be called in to face their inevitable fate at the capable hands of either the Headmaster or the Head-Boy. And believe when I say capable hands, for whatever else they may have been both the Headmaster and, in my own experience, a succession of Head-Boys were eminently capable when it came to laying the cane onto a lad’s naked arse. Then, their beating finished, nursing their welted and painfully roasted arses, the unfortunate recipients returned to the changing room to put back on their day clothes before returning to their respective houses. I suppose that one could give some marks for empathy to the Headmaster and the Head-Boy in that beatings were always in the evening so that the lads could go straight to bed afterwards and nurse their wounds rather than having to go and sit on a hard wooden seat in class again.

In the individual houses, beatings also tended to be in the evenings, and there what usually happened was that the unfortunate victim was called from his dormitory wearing just his pyjamas, the trousers of which could easily be dropped  to give access to that all-important part of his anatomy to be addressed by the cane. So by now you have, I am sure, all got the message; the cane and birch reigned supreme at Frogmore and were always applied to the bare arse of the miscreant.

CHAPTER 3

But I have got ahead of myself, as when I first arrived at Frogmore, I knew nothing of what I have just recounted above. In fact, I was like a fish out of water as the other first-year boys, both in class and in my dorm in Hanover House, were all products of an English preparatory  school, for the most part, but not exclusively, Frogmore Court. The English preparatory school, a more or less obligatory precursor to the public school, was also, in the main, totally devoted to the beneficial effects of the cane applied to the naked bottoms of its charges; so most if not all of my classmates that first year were fully conversant with the joys of the cane. Add to this naivety of a young boy from the Mid-West of America, totally unfamiliar with English ways and with an accent which sounded harsh and crude in the context of a group of upper-class young lads all of whom spoke the sort of English which the average American and indeed, also the average young Brit, qualified as toffee-nosed, you can easily see that I felt like an outsider: someone from outer space; and let’s face it, for that is exactly what I was; an outsider.

Outsider or not, possibly out of curiosity value, I found myself appointed on my first day as the Head-Boy’s fag.  I was, as an American, not familiar with the word fag, before I became one, although having received the honour I did look it up in an American dictionary to find what the word actually meant. The expression, it’s a bit of a fag means the same thing in America as it does in England: that the thing you are doing is a bit of a drudge and you would rather not do it. But as used in the British public school context, the fag is not the task but the boy whose job it is to perform the task.  In a word, a fag at Frogmore was a first year boy, who functioned as an unpaid servant at the beck and call of an older boy. In fact, by the time I arrived at the school, fagging, as the act of being a fag was known, had more or less been eliminated – but not quite – as the Head-Boy and the six House-Captains, each had a dedicated fag to carry out menial tasks on their behalves. In the case of the House-Captains, first year boys took it in turn on a rotational basis during the year to fag for the Captain of their house, so that a modicum of democracy existed. However, in the case of the Head-Boy, it was was what one might call a job for life; well not exactly for life, but for the full school year; with no relief at all in the form of someone else taking over part way; and so I found myself at the mercy of that year’s Head-Boy, a handsome looking, blond-haired aristocratic type  called Robert Digby-Scott, who, as I quickly found out, was a totally unforgiving bully in spite of his attractive outward appearance,

The Brits are very keen on double-barrelled surnames, which usually mean that the holder comes from the top reaches of the upper social classes; and Digby-Scott, as I quickly learned I had to address him as such, knew his place in society and kept me in mine.  I never understood how I, a gauche mid-westerner from Chicago, with my grating, American accent which stood out like a sore thumb at Frogmore as soon as I opened my mouth, came to be selected to act as skivvy, for that was what I became, to this arrogant young man. But I did and I was stuck with the job.  Digby-Scott occupied that suite of Head-Boy’s rooms along the corridor from the Headmaster as I have already described above and in his position of Head-Boy, given his job of sharing the regular Monday, Wednesday and Friday evening punishment sessions with the Headmaster, was more or less the flagellator in chief of the school. As I quickly realised, no one in the whole school whacked more arses than he did, given the habit of the Headmaster of leaving all but the most serious of cases to his Head-Boy for correction. And in this respect, no one could have done the job better than Digby-Scott did; for as I quickly found out to my own cost, he was a consummate expert with the cane, which he was always ready to use at any time in addition to the scheduled punishment schedules.

One of my first tasks with him was to lay out his clothes for the following day in his bedroom each evening. Digby-Scott was a vain, young man and had two complete school uniforms; lord knows how many shirts and sets of underwear and two pairs of black Oxford shoes, which he which he insisted on being shined to a high polish. And that is how I fell afoul of him on my second day as his fag, when I had not cleaned his shoes to his liking which he made very clear saying: “Stevens, you have made an absolute pig’s ear of cleaning my shoes.  Get back to the service kitchen and do the job properly before I feel obliged to teach you a lesson.” I can tell you that I needed little imagination to see how he taught boys a lesson as there in a stick stand at the side of his desk was a large selection of wicked looking rattan canes. So I kow-towed to him, metaphorically touching my forelock with my knuckle in the way sailors of old did, and scuttled off to rectify the situation.  But every little error I made was drawn to my attention with threats of correction as he liked to call it.

Thinks came to a head or better put, came to my arse, in the form of my first beating the first Friday afternoon of the new term. Digby-Scott had invited the six House-Captains to his study  where he proposed to carry out what I later learned was an annual ritual of distributing new rattan canes to the prefects.  This ceremony was part of an old, Frogmore tradition going way back.  At the start of the new school year in September, the Headmaster ordered several boxes of new rattan canes which the Head-Boy then handed out to the House-Captains who in turn then passed on the appropriate rods of justice to their co-prefects. Digby-Scott told me to be ready to make tea for him and his co-prefects but before that to go along to the school stores and collect the new consignment from Mr. Jennings, the janitor. Well when I got there, Jennings had the canes ready for me to pick-up and take back to the Head-Boy’s study but to my amazement they were in no less than seven, three-foot-long, shallow cardboard boxes. “Come on lad, hold out your arms and I’ll load you up,” said Mr. Jennings jovially as he added, “They’re not heavy and you’ll be able to manage them in one go. Just take your time lad, and you’ll be alright; but try not to drop them as you’ll have a hard time picking that lot up again by yourself.”  And so with these comforting words, I left with seven boxes in my outstretched arms. And it was true; they were not too heavy; but they were very cumbersome.  All went well until I arrived at the door of Head-Boy’s study which I foolishly tried to open myself rather than knocking, thereby allowing the whole lot to come crashing down. 

Digby-Scott heard the crash and flung open the door to find me attempting to pick up the boxes, several of which had split open and deposited their contents onto the floor. “What on earth are you doing you clumsy oaf? Why did you not knock and have me open the door for for you.  Pick that lot up and bring them inside and try to put them and back in their boxes in some sort of order.”  Dying with embarrassment I picked up the fallen items and put the lot as indicated on a table under the the window. Digby-Scott stood over me wearing a gloweringly exasperated expression;t I, totally flustered and nervous, attempted to restore some order into the mess I had inadvertently created.  I read for the first time the labels on the boxes. Six were the same and read:- 

Acme School Supplies 

This box contains two junior and two senior, straight-handled, school- punishment, canes. These canes are made of the finest, seasoned Malacca rattan which is universally acknowledged as the material of choice for the finest punishment canes.  Oil them with our patent cane oil once a year and they will give years of faithful service. 

The seventh box contained six assorted senior canes and was obviously intended for the Head-Boy, although I did wonder why he needed them when he already had at his disposal a stick stand bristling with a large selection of such weapons – which is how I thought of them. Just looking at all these weapons of punishment made my blood run cold.

“You had better cut along to the kitchen and make the tea as my guests will be arriving in a few minutes. And do try, Stevens, not to make a mess. You need the large teapot as we shall be seven so do remember to bring enough crockery and the milk and sugar and please try not to drop the lot this time Stevens.” 

Armed with this cautionary order, I duly went to make the tea and things went from bad to worse.  Can you imagine a more absurd request than asking a young American lad to make tea for a group of senior English publics school boys?  I have to admit that I forgot completely that the beverage I had drunk at breakfast since the start of term was probably tea. But for me, a Chicagoan, tea meant a branded cold drink, known as Lipton’s Ice Tea, which was sort of a bit like second-rate Coca Cola except that it was not fizzy; but how it was made, I had not the faintest idea; it was always there in the fridge in summer and I just helped myself. So as far as making tea was concerned I had about as much idea how to proceed as I had about speaking Chinese. In the kitchen, where boys were allowed to make hot drinks for themselves, I questioned one of the older boys about what to do, to receive a rather witheringly condescending reply that it was simple. All I had to do was to put  three heaped tea-spoons of tea into the large pot and pour on the water, which I duly did; but of course, my informant had not stressed the fact that the water needed to be boiling, so when it seemed to me to be hot enough, into the pot it went.

Feeling rather proud of my modest achievement, I carefully carried the tray loaded with crockery, teaspoons, milk and sugar back to the Head-Boy’s study, where the House-Captains, including Mark Simmons, the then captain of my own house, had already arrived and were eagerly examining their new sets of canes.  I should have remembered that pride often goes before a fall and my fall, which unbeknown to me at that moment, but which was already pre-ordained by my incompetence in making the tea, was really painful when it finally happened.  As I entered the room bearing my load, I could feel the sense of erotic euphoria in the air as these guys salivated over this collection of sticks and the purpose to which they would be put. I noticed that for one or two of them, just the act of fondling the canes turned them on as clearly shown by that faithful but uncontrollable, tell-tale indicator: the tenting of the crotches of their pants.

Digby-Scott lost no time in putting me in my place; “Well Stevens, I see you finally made it; and about time too; what took you so long? We all thought that you had gone to China to fetch he tea. Well better late than never, (I was not actually aware of the fact that I was, evidently, late). So anyway now that you are finally here, get on with it boy; put that lot on my desk and pour us all a cup of tea as we are all practically dying of thirst.” I did as I had been bidden and to my horror as the first cup of tea poured from the spout of the tea-pot, I saw to my utter horror that what should have been a clear liquid emerged with huge, floating, log-like tea-leaves.  Digby-Scott’s reaction was immediate and to say the least, angry:  “Stevens, you are an utterly incompetent idiot.  The water was clearly not boiling when you poured it onto the tea and as a result the tea has not drawn properly and it is totally undrinkable.  Take the pot back to the kitchen and make a new lot immediately and see that the water is properly boiling this time before you pour it into the pot.” Can you imagine how I felt? I was utterly petrified by what had happened. “Well boy, don’t stand there dithering; get out of here and get on with it; you will have a lot to answer for if you find us dead with thirst by the time you get back.”  Talk about making a mountain out of a molehill; my fag-master had managed to blow the thing up into the full range of the Rockies and had made me feel so very small as I scuttled out of his study bearing the fated pot of tea to try to redeem myself.  But somehow, I sensed that my goose was cooked whatever I did; and I was right.

The second pot of tea, successfully made and poured, I stood there under  the collective and maliciously baleful gaze of the assembled House Captains, wondering what would happen next as I had been given no further instructions by Digby-Scott and had been left to stand there in a high state of fearful, nervous anticipation of what was to come.  My own House Captain gave word to what I imagine were the collective thoughts of the assembly and issued what amounted to a call for my immediate execution as he said:  “You know, Digby-Scott, if Stevens were my fag I’d not hesitate to give him six right now to teach him a lesson, which after his performance today he richly merits.”

“My dear fellow, you don’t know the half of it. Stevens has demonstrated his incompetence and lack of application since the moment he started fagging for me earlier his week.  He not only left my shoes unpolished but he also then threw the new boxes of canes onto the floor, which is why some of the boxes are split open; and then the final straw, his performance with the tea.” He then went to the stick stand at the side of his desk and looked over the canes, finally choosing one and pointed it at me: “Stevens, as your own House-Captain has just said, you really do need correcting  and I think that is probably the view of us all.” He looked around the room and there was a collective murmur of agreement from the House-Captains, who scenting blood, were only too willing to give their approval.  “Stevens, kindly move the beating stool from over there by the wall into the centre of the room and bend across it in the usual manner when I shall give myself the pleasure of correcting you in the time honoured manner we use here at Frogmore.”

The beating stool? The usual manner? I felt my heart rate rise to panic pitch as I realised that I was about to get my first Frogmore beating.  I confess that until the word, beating stool, had been mentioned, I had not noticed this professionally-made piece of purpose-built furniture designed to accommodate all heights of boys.  As I shifted this heavy chair, for this is what it was, to the centre of the room, I saw that it had a very heavy, leather-covered top rail which was adjustable to any height by a simple screw mechanism, so that the unfortunate victims who was to be corrected – in this case me – could present his bottom in the perfect position to receive his punishment: an ingenious and useful piece of late late Victorian imagination, which showed the devotion of our forebears to the benefits of corporal punishment applied to errant schoolboys’ backsides. Familiar as I was with the paddling’s I had received at my prep school back in the USA, I naively then bent across the back of the chair which seemed to be set at about the right height for me, placed my hands on  the seat, stuck my bum into the air and waited for the onslaught. There was a long silence during which nothing happened.

“Stevens, what on earth do you think you are doing?  When I tell you to bend across the stool in the usual manner, I expect you to do as you are told and not to try to make a fool of me.”  I had no idea, none at all, what he was talking about but he quickly made it clear: “Stevens, you really are a naïve nit-wit with no idea at all of how we deal with boys like you here in England; so let me help you to understand what is required of a boy who is to be corrected here at Frogmore.  First of all, Stevens, all beating is done on the bare arse (that was the first time I had heard that word used; but I soon learned that is was the expression universally used among the pupils at the school).  So Stevens, take off your blazer, your shoes, your trousers and underpants, and bend across the chair again and let me see your bare arse. Come on boy; jump to it, I haven’t got all day.”

My heart, already racing, now went into overdrive.  I had had no idea until that very moment that the cane was applied to the naked backside of the offender, although thereafter it quickly became commonplace as I seemed to have no problem in collecting beatings. But at that moment, the prospect of exposing what I had hitherto thought of as my private parts in front of the assembled company was highly embarrassing, not to mention very frightening.  I was my first real experience of that state of nudity, either total or semi, which was a very common state of dress – or better put: undress – at Frogmore. Boys in British public schools live, shower and sleep together so that there is no way that one’s private credentials remain unscrutinized by one’s classmates. So trembling with fear of the unknown, I did as I was told. What else could I do?

Digby-Scott looked on impatiently and then came across to the chair over which I was now bent, and adjusted the height of the back to his liking so that I found myself with my naked arse stuck in the air with only the tips of my toes touching the floor.  And it was with me in that unhappy, uncomfortable position that the Head-Boy then went ahead and gave my poor naked arse six resoundingly painful strokes of the cane.  I had braced myself for the first stroke, thinking that it would be much the same as with the American paddle; but I was just so very wrong; it was ten times more painful!  I suppose that all boys have the same reaction the first time a well-applied rattan cane lands with that resounding crack on their naked skin; they wonder what has happened and whether they will be able to stand the coming strokes.  I don’t know how to describe the pain as it was unlike anything I had felt hitherto.  I suppose it was how it might feel if a red-hot poker were laid across your naked skin; not that that was a comparison I wanted to experience.  But I saw that Digby-Scott was an expert with the rod; he had clearly served a  successful apprenticeship previous year as junior prefect to the gentle art of flagellation; he now had what one could but define as a highly refined technique; he left long pauses between each cut to allow me allow me fully to appreciate his skill.  It was an absolutely awful experience, but it did introduce me to the real world of Frogmore, which as I rapidly saw, truly did merit its nickname of Flog-more: a place where the cane rarely slept for long. 

Finally told to get up from over the chair, I put my clothes back on and cleared away the tea things as if nothing had happened.  I can tell you that I made my way back to the kitchen with the tray loaded with the dirty crockery and my arse feeling totally on fire. I am not ashamed to tell you that I wept bitterly as the pain was just so great. That evening at supper I could barely sit down at table and was really relieved when I could get back to the dorm, take a shower and go to bed to nurse my wounds. My peace was short-lived as my trials and tribulations were still not over for the day. It was about eight in the evening when one of the two junior prefects suddenly appeared in the room:  “Stevens, get your arse out of bed; Simmons (the House-Captain you will remember) wants to see you in his study right now.”

CHAPTER 4

Commands, even from a junior prefect, were given to be obeyed without question and so I pulled myself stiffly out of bed and started to take off my pyjamas to put back on my day clothes only to be told curtly: “Forget dressing Stevens; you can go and see the House Captain just as you are; your pyjamas will do just fine; in fact I think that you will find they are perfect for the occasion.  Now get a move on as Simmons wants to see you pronto and it does not do to keep him waiting.”  I wondered why on earth the House-Captain, the very man who had precipitated matters that afternoon and got me my first thrashing, wanted to see me.  But I can tell you, as I am sure you can imagine, that it was with some considerable trepidation that I went along to his study, asking myself  what I had done to warrant such a summons and what was to happen to me now;  I did not have to wait long to find out.

Simmons received me with scowling face which boded ill: “Stevens, were you aware that the Head-Boy, for whom you have the honour to be the fag (some honour I thought!) was, until he was named Head-Boy for this year, a prefect of this very House?  Let me tell you Stevens, that I was mortified that a boy from this house, my House, the House of which the Head-Boy is still an honorary member, could make such a mess of things: simple things, which any normal boy would be able to accomplish with no problem; but you apparently could not.  Now as far as I can see your attitude is all wrong. You are from America where things are probably done differently, but you are now here enjoying an education in England and we expect you to show the right attitude (that word again; what did he mean by it?) which as far as I can see, you so far have not.  And so it falls to me as your House-Captain, to try to inculcate into you the values which we at Frogmore cherish. (My god! what a load of pompous tripe!) Now I think we would both agree that the Head-Boy was very lenient with you when beat you this afternoon. (I certainly did not feel he had been lenient, as the pain in my arse was continually reminding me as Simmons was speaking.)  And so Stevens, I feel I have no option but to take additional measures to set you on the right road to acceptable behaviour in this school; to help you to improve your attitude in general.”

At this stage, having finished his rather pompous peroration, Simmons evidently decided that actions spoke louder than words; so he got up from his desk, in front of which I was standing with my back to the door dressed only in my pyjamas, walked around me and reached up to the door on which several rattan canes were hanging from a hook. He selected one and came back to face me, waving the cane under my nose and said:  “So Stevens, in view of the leniency of the Head-Boy, I propose to give you an additional six as your punishment this afternoon was, in my view, much too light.”

So there it was; Simmons, whom I correctly saw as a sadist, simply wanted to thrash my arse himself for no good reason and that was that. I knew that I would be wasting my breath to protest and so I waited silently until he spoke again.  I confess I was shivering with fear at the thought of what was now be visited upon me as my arse was still very sore from the onslaught it had suffered earlier that day. Simmons placed a simple hard backed chair in the centre of the room and said: “Stevens, go and stand behind the chair, drop our pyjama trousers, bend across the chair in the usual manner, place your hands on the seat and keep perfectly still whilst I administer your punishment; keep your hands away from your arse until I am finished and tell you to get up or I shall be obliged to start again from the beginning.”

So there I was, for the second time that day, my naked arse in the air, waiting for that first horrible stroke to land.  I steeled myself and swore silently that I would deny my sadistic House-Captain the satisfaction of seeing me reduced to tears. And so, as stroke followed painful stroke – and let me be clear that Simmons was just as proficient with the cane as was the Head-Boy – I  managed to remain silent; I neither cried-out with the excruciating pain he delivered nor did I shed a tear; it was hard; very hard indeed; but I managed to keep silent. When Simmons saw that he was not managing to break me and as stroke followed stroke, he increased his intensity.  Finally it was all over and I was told to get up, pull back on my pyjama trousers and leave.  I limped back to my bed, where my dorm-mates were agog to see what had happened to me. I had the satisfaction of being the hero of the moment, for Simmons was universally unloved by one and all.

And I had the distinction of being the first boy in my year – the first of many times for me, I might add – to  undergo what I came to think of as the traditional post mortem viewing of a freshly beaten arse. After expressions of sympathy tinged with a mixture of both fear for themselves and admiration for me from my mates at the sight of a twelve-cut welted arse, I climbed back into bed; my arse was on fire; the pain was excruciating; but I finally went to sleep sobbing quietly to myself. But I had the satisfaction of knowing that I had survived the first of many beatings which unbeknown to me at the time, would dog my future life at Frogmore. It was only a few weeks later that I learned that the concept of the well-beaten arse, was something of a hallmark of the school.  My first experience surely qualified for that accolade as did my many subsequent beatings, but it was only years later, in fact, in the final days of my final year at Frogmore, that I really experienced what a truly gold standard, well-beaten arse felt like.

I won’t burden you with a chronological account of my numerous confrontations with the cane during my life at Frogmore other than to recount the details of two painful occasions, one of which changed my life forever and I suppose set me the road to my future career – if you can call it that – as a Male Escort.  But before I tell you about that occasion, which occurred when I was just sixteen and in the fifth form  let me jump some two years forwards in time to the last week of term in my final year at Frogmore.  This was the one and only time in my entire career at Frogmore, that I was beaten by Headmaster himself. Over the years I had been beaten at least once a term by my Housemaster, by every Head-Boy and by every House-Captain of Hanover, not to mention by sundry other prefects.  For some reasons I was one of those people whose arse just seemed to be a magnet for the cane, and one way and another I was seldom without a sore bottom for long, But it was not until that final, fatal week when I was in the upper sixth that, together with my then closest friend with whom I had enjoyed a long term sexual relationship as a sixth-former, that I was beaten by the Headmaster himself.

CHAPTER 5

During my years at Frogmore the Headmaster was a certain Dr. W. C. Bellamy, DD, of whom my immediate impression was of a tall, bony, humourless man who should have been put out to grass a long time ago.  But of course to a thirteen-year-old as I then was, even a man of forty seemed old. At first sight he appeared to me to be a superannuated hangover from the days when public schools were often headed by clergymen. But that was just my impression, for Dr. Bellamy ruled the school with a rod of iron and had over the years acquired a legendary reputation with the cane and the birch, both of which, according to reports of those who had had the misfortune of being obliged to allow him to whack their arses, he applied with an unbelievable and unequalled vigour. What happened was that Clive Garrard my closest friend and sex partner – I say sex partner rather than lover, as it was really just raw lust which kept us together – and I very foolishly decided one Friday night at the end of our final term, to go down to the local pub and have a few drinks and smoke a fag.

Now we were both eighteen at the time and of legal age to indulge in such activities. Of legal age we may have been; but the school rules, which as far as smoking and drinking were concerned, were tantamount to being engraved in tablets of stone, forbad both activities on what was the Frogmore equivalent of pain of death if the perpetrators of the offense were caught in flagrante. But it was just the fact that smoking and drinking were so very strictly forbidden which made them so enticingly attractive to the likes of us.  And so, fully aware of the potentially painful consequences if we were caught, on the last Friday evening of term, we sneaked out of the school grounds and went down to the pub.  Now as I mentioned earlier, the Headmaster had more or less abandoned the application of the cane and birch himself, leaving regular beatings, of which, believe me, there were plenty, to the Head-Boy of the day.  But he was absolutely adamant when it came to the two cardinal sins of smoking and drinking; he insisted that any prefect or master who caught any boy in the act report the culprit to him.

So of course it goes without saying that Clive and I were caught in the act. In fact we were caught by our own Housemaster, who had been alerted to the fact by one of our own House junior prefects who had, by chance, seen us entering the pub; the Housemaster had then seen fit to come down to the pub himself, find us in the bar, turn us out and send us back to the school with dire verbal warnings about the severe consequences we would reap for our misdeeds. Next day was Saturday and nothing happened; and so with a sense of false security, we sort of thought that the whole affair had blown over; but we were just so very wrong!  After chapel on Sunday morning, the Headmaster made his usual announcements and then the axe fell as he concluded, almost as an after-thought:  “Now before I forget, Stevens and Garrard, I want to see the two of you this afternoon at three o’clock precisely in my study. Oh and I am sure that I need not remind you that you should both present yourselves wearing the – and then came those fateful words – appropriate attire. I always feel that one should be correctly dressed for every occasion and for this occasion the appropriate attire will be very suitable.” He did not have to specify why he wanted to see us or what he had in store for us; those two words, appropriate attire, said it all.

This announcement was made in front of the entire school and a buzz went round the congregation – an appropriate word as the announcement had been made at the end of service in the chapel – as the sensational significance of what he had just said sank in: Two upper sixth formers were to receive a beating from the Headmaster that very afternoon.  This was an amazing piece of news the Headmaster rarely beat anyone and never on a Sunday; but here he was, proposing to shred the arses of two boys – young men really – who would be leaving the school forever in a few days time when the term ended. What had they done to deserve this?  The prurient curiosity of the entire school was aroused. Then word went round that someone had seen the school handyman making up a set of new birches in his store-room on Saturday afternoon; so connecting the dots, it had to follow that Stevens and Garrard were to be birched.  This truly was the juiciest piece of news the school had heard all term and some of the older boys already had a hard on just thinking about what was to happen; two, luciously muscular arses were to be beaten to pulp – well not quite – that very afternoon. But why? It had to be something serious for the Headmaster to make such an announcement in public and in the chapel to boot; clearly it was a warning to others that no one was above the sacrosanct Laws of Frogmore and that penalties associated with their breaking would be upheld right through to the final minute of a boy’s career at the school.  So although the announcement had raised great interest it had also made the boys think that what was about to happen to the hapless pair, might one day happen to any of them; and that was a really sobering thought.

Three o’clock arrived and Clive Garrard and I presented ourselves at the door of the Headmaster’s study wearing just our gym strip and slippers.  I knocked on the door and there was no reply and we were left standing  there in the corridor by the Headmaster, who had evidently decided to let us stew in our own juice for a while; presumably to heighten the already palpable state of nervous tension we were both feeling. He was clearly not alone in his study, for as we stood there we could hear, through the closed door, the murmur of voices from within; the door was eventually flung open, rather melodramatically, by Gerard Oliver, the then Head-Boy, whom Dr. Bellamy had obviously invited to assist him in a task which had become increasingly rare: a Headmaster’s beating; or was it sort of an end of term treat for the Head-Boy to thank him for his assistance during the term? After all, even if the Head-Boy was just there as an observer, it was a place that Sunday afternoon for which most lads would gladly have given their eye teeth to be present; just think of it: an opportunity to see two sixth formers having their naked arses birched; it was the stuff legends were made of; a spectacle to arouse that streak of sadistic eroticism which is hidden deeply dormant inside most boys and which is awakened when they see someone being beaten; it was just a too utterly delicious, sexually-arousing prospect to contemplate, which was, however, as far as it would get other than for the Head-Boy.

However you looked on it, one could see from the expression on the Head-Boy’s face that he was really looking forward to his part – whatever that was to be – in the performance which was about to begin and in which Clive and I had the main roles. Frankly speaking as someone whose backside was accustomed to being caned, on this occasion I have to admit that I did feel a shiver of fear run though my body as we entered, for the very first time in both our careers at Frogmore, that holy of holy’s, Dr. Bellamy’s study.  As I mentioned above, I had, over my years at the school, been beaten times without number by all and sundry, prefects and Housemasters, who, over the years, had been authorised to swing the cane; but never until now by the Headmaster. So you could chalk it up as a first for me and also a first for Clive as he too had never before been in the Headmaster’s study. But as I took in the surroundings in which we found ourselves, my heart sank as I saw lying on a table several freshly made birches and to the side, one of those professional beating-stools which I had only ever before seen in the Head-Boy’s study and over which I had bent several times in the past to have my arse roasted by a succession of Head-Boys.  The present Head-Boy, Gerard Oliver, was in the same upper-sixth form as Clive and I; but although he had the authority to beat any boy in the school, he had, to the best of my knowledge, never beaten any of his sixth-form classmates. But sanguine though I generally was about being caned, as I felt I had become immured to the act; on this occasion I admit to having a really uneasy feeling about what was about to happen to us; and when it finally did, my worst fears proved, unfortunately, to be right; it truly was one of those ghastly occasions from which, to use an Americanism, I would have preferred to have been included out!

Dr. Bellamy sat behind his huge desk, with the Head-Boy standing looking on to one side. Clive and I, appropriately attired, looking like two overgrown schoolboys which is, of course, exactly what we were, stood stiffly to attention in front of the old man, attempting as best we could to look penitent in the vain hope that things might not be quite as bad as we envisaged; as events turned out, we were, of course, totally wrong; they were just about as bad as they could possibly have been.  The Headmaster addressed us at length in no uncertain terms, and leaving us in no doubt whatsoever about the seriousness of our crime and what he thought of us. The Head-Boy played the role of a silent Greek chorus and as an approving onlooker nodded his agreement at each point the old boy made.  Finally things came to the inevitable head and Dr. Bellamy said:  “And so gentlemen, I find I have no alternative but to inflict upon you the most severe punishment that is but rarely used in this school.”  

He did not get around to telling us what our punishment was to be, but at least he was clear enough to call it a punishment and not a correction; so I suppose we thought that we knew where we stood, but frankly as things unfolded, we had not the faintest idea of just how awful things at Frogmore could be. “Kindly remove your shorts the pair of you and go and stand against the wall there with your hands on your heads.”  The Head-Boy looked on with visual approval at the obvious, humiliating embarrassment we were being made to suffer, standing there half naked in front of him and the Headmaster.  Can you imagine what it felt like to have to stand there with our genitalia – and we were both pretty well endowed in that department – totally exposed.  It was not as if any of us were unfamiliar with the sexual attributes of the young, naked, male figure, which frankly I personally found very, very appealing; but it was one thing to see one another naked in the daily context of the gym changing-rooms or in the showers each evening or morning but quite another to be made to stand there as if posing for a sculpture, with nothing to preserve what is commonly called one’s modesty. And of course, the inevitable happened; both our cocks, with that mind of their own that the male sex organ always has, started to rise to the occasion.  I noticed that the head-Boy too was not immune from a similar problem as the tenting of the crotch of his pants showed.

But action time finally arrived as the Headmaster picked up one of the birches, motioned to Clive move towards the beating stool, across which he was then told to bend. And then both the Head-Boy and I had the unpleasant experience of watching Dr. Bellamy wield the birch across my closest friend’s naked arse.  And let me just add, that in spite of his   rather decrepit appearance, he was a clear master at the task.  He separated each stroke from the next by that all-important, appreciation interval; with six strokes administered standing on Clive’s left he had already completed covered his arse with the fine welts which the birch creates. He then moved to Clive’s right side and proceeded to give him another six cuts so that by the time he had finished, Clive’s arse was was a bright red colour all over. I have to admit, to my shame – but then I am human with all the human failings – that  even under these unhappy conditions when I knew full well that I was about to suffer the same treatment, I did experience a feeling of erotic pleasure as the birch descended time and time again on my friend’s naked flesh; by the time Clive was told to get up and regain his position against the wall with his hands again on his head, my own cock was rock-hard with the sheer eroticism of what I had just witnessed. To me there seemed no doubt at all but that corporal punishment, in the context I had just witnessed it, was sexually stimulating. However as Dr. Bellamy motioned me to take my place across the beating stool I could not help but notice that poor Clive had evidently had all the spunk beaten out of him, as his normally perky cock was now hanging like a limp rag between his legs.

As I assumed the position – the words the Headmaster used – and braced myself for what I now knew was to be a twelve stroke onslaught on my arse, I could not help but wonder why Clive had been told to resume his position against the wall and had not been allowed to put back on his shorts. This was my first encounter with the dreaded birch and I had no clear idea of what to expect; but I can tell you that the accounts I had heard of the pain which an expert hand could deliver with those fine twigs were totally correct; and one had to admit that Dr. Bellamy had an expert hand. The first stroke gives you the impression that it is not going to be too bad, as the twigs spread out across your arse and give you little more than an unpleasant sort of tingle. But then as stroke follows stroke, the pain rapidly builds up until by the time the sixth is delivered your whole arse is on fire with the pain which by then has already become practically unbearable. But in this case, with six more still to come, what could I do but grit my teeth and bite my lip in the hope that I would maintain a certain dignity? By the time the old boy had finished shredding my behind, I felt as if my two buns and flanks were on fire; it was a truly horrible experience.  But in contradistinction to how Clive had reacted to his ordeal, the birch did not beat the stuffing out of me and my cock was still as firm and solid at the end as it had been when I first bent over the stool.

The Headmaster told me to join Clive, and stand against the wall with my hands on my head; I still could see no reason why we were both not allowed at least to hide our nakedness by putting back on our shorts; but that respite was clearly not to be, as Dr. Bellamy seated himself behind his desk again with the Head-Boy, a malevolent smiling look on his face, at his side. He looked at the pair of us as he said: “Well gentlemen that is the first part of your punishment completed, so I think that we will take a pause of five minute or so before we pass to the second phase.” 

Neither Clive nor I could believe our ears; we had just received the thrashing of our lives; but that apparently was not enough; Dr. Bellamy was clearly out for our blood. He then decided to enlighten us as to what was next in store:  “Gentlemen, the misdemeanour you committed is quite the gravest, short of stealing, which the school recognises.  Now in case you are unaware of the fact, the school rules limit the number of strokes of either the cane or the birch or a combination of both, to a maximum of twenty-four cuts for any one offence. Only very rarely do I ever felt the need to resort to such a severe measure, but today in view your seniority and the fact that you were caught both smoking and drinking in a public house, itself a strictly forbidden venue for boys from this school – whatever their age –  I feel that such a severe punishment is totally justified as it will bring home to the two of you not only the gravity of the offences you committed, but will also serve as a warning example to the rest of the boys of what will happen to them if they break the rules. So gentlemen, in a few minutes, I intend to charge the Head-Boy with the task of completing your punishment by giving each of you twelve complementary cuts with a senior cane across your bare bottoms.”

This was an unbelievably horrific piece of news; we were to receive another severe beating and the Head-Boy was to be given carte blanche to thrash what remained of the living daylights out of our arses, which had just suffered an unbelievably severe roasting with the birch.  No wonder he was looking so pleased with himself; I could see from the look on his face that he was going to enjoy every minute of thrashing two of his class-mates. As Dr. Bellamy had said, this was the severest punishment the school allowed him to dish out. No one in his right mind would ever wish to take such beating and I guess if we had known what we were risking by way of such reprisals when we went off on our pub jaunt that Friday evening, we might have thought again before setting out on it. But we had not given the slightest thought to the potential consequences of our actions and there was little point in being wise after the event; we now had to face the music, which if my suspicions were correct, the Head-Boy would play fortissimo on our naked arses. But the ironical thing about the whole business was that neither of us really liked smoking or drinking that much; we has just gone to the pub in a vainglorious, macho attempt to assert our independence; but alas we had become unstuck; very unstuck indeed.

Clive was again the first to mount the metaphorical scaffold for his execution.  The Head-Boy advanced on him with the senior cane in his hand and applied the first stroke, with great force I might add, so that as I stood there, hands on my head with my cock fully erect, viewing the slaughter which was taking place before my eyes, I saw from the expression on his face that the Head-Boy was really enjoying what he was doing and that he too, to judge from the tenting of the crotch of his pants was also fully sexually aroused by the  act he was carrying out; with no unseemly hurry he laid on stroke after cutting stroke in neat parallel lines running down Clive’s arse from the bottom of his back to the top of his legs.

As stroke followed stroke producing deep angry welts almost immediately, Clive let out moans of pain. His tormentor laid on ten strokes one after the other; he then paused before completing his onslaught with two final, particularly vicious cuts which he placed in the form of a diagonal cross, thereby leaving Clive with what I am sure the Head-Boy thought of as an artistically well-beaten arse. And one has to admit that Head-Boy Oliver was an absolute expert with the cane. But one thing was sure and certain; the Headmaster and his current Head-Boy had elevated the Frogmore speciality, that much-vaunted, well-beaten arse, to a level of excruciating pain which one would have hardly believed possible; this surely was the solid-gold version of the ultimate punishment, bearing the twenty-four Karat hallmark.  As Clive stiffly managed to stand up and regain his position against the wall, still half naked, hands on his head against to witness my caning, it was with some trepidation that I stepped forward to face my own fate.

That was the final time that I was beaten at Frogmore. Summer term finished two days later and I left the the school for ever.  I went first to stay with my grandparents for a week before flying back to Chicago to resume my life in America.  My grandfather ever very observant, but never the most sympathetic of men, looked at me and said: “Well young man, I see you have evidently been beaten again. But I suppose you deserved it.” And then, by way of what I guess he saw as words of encouragement and sympathy, he added: “Cheer up lad, you’ll survive!” 

Thus ended my involvement with an English public school education. For the record I will just add that I have never since that date been back to England.

CHAPTER 6

But I now must backtrack to that other memorable occasion when I was beaten aged sixteen when in the fifth form at Frogmore.  I have reported these two beatings in reverse chronology as it is this earlier beating which radically influenced my future life long after I had left Frogmore.  But first let me tell you something about myself, as I have up to this point, concentrated mainly on the school and its devotion to the cane, with which as you have seen, I was regularly intimate – I really like that word – throughout my entire school career.

When I arrived at Frogmore aged thirteen, I knew nothing at all about sex, but by the time I was approaching fifteen, I knew that I was naturally attracted towards other boys, particularly those well muscled young studs who were members of the various sports teams. I had always been a keen sportsman myself and spent a lot of time keeping fit, working out whenever possible in the gym. I became a keen rugby player, at which game I became a very adept player, so much so that I finally made the school’s top rugby team: the one which competed against similar teams from other schools. I was big for my age and thanks to my efforts in the gym, I had developed a fine muscular body of which I was quite justifiably proud. But most importantly, I was extremely well endowed by nature where it matters most; in a word I have a really big penis, or cock as we universally referred to it at Frogmore.

Anybody who is even vaguely familiar with the life of a public school boy knows that nothing ever remains secret for long. And living, sleeping, showering, playing games and so on with one’s peer group means that even ones most private parts are regularly exposed to everyone.  Any shyness which a boy might have had about his sex organs on entering the school is soon blown away by the fact that boys are naked together on a daily basis in the showers, where everything is revealed. And of course, the size of one’s male organ is of great interest to all and sundry.  I thanked my lucky stars that I was well endowed in that department’ so much so that I was chivvied good-naturedly from my first year on, always with a certain degree of envy, about the size of my cock. But my cock was not only of interest because of its size but also because of the fact that as an American, I had been circumcised, an act which is very common in the USA, but rare in England; so all in all my genitalia were of great general interest to my school-mates.

But lack of any detailed sexual knowledge did not stop most of us, by the time we reached fifteen, of discovering the joys of masturbation: wanking in Frogmore speak!  And as we grew older, working one’s cock for sexual relief, for which you needed no instructions whatsoever, became a fact and feature of life, however much the powers-that-be exhorted us to refrain from what they coyly called self abuse.  And it goes without saying that some boys, with a complete absence of female company, started having sexual relations with their friends. So although it is unfair to say that buggery was universal, it was nevertheless present and I have to admit to being one of those guilty of indulging in it. I very quickly realised that I was a gay, a homosexual, as I had eyes and interest only in other boys at school and had no need for members of the other sex to satisfy my needs; so much so that by the time I left Frogmore aged eighteen after that monumental birching and caning together with my friend Clive Garratt inflicted on us by the Headmaster and Head-Boy,  I was more or less a practising gay; my sexual liaison with Clive had gone on for some two years when we finally parted when, aged eighteen, we finally left Frogmore forever.

This brings me to the significance of the beating with which I opened this section of my memoirs for this was to prove one of the determining acts ever visited upon me at Frogmore: much less painful than that horrible, let us call it my, Farewell to Frogmore Flogging, but much more influential in that it pointed me in the direction which my natural latent sexual desires would inevitably have driven me; finally one simply cannot deny one’s sexuality. One Friday towards the end of the summer term when I was sixteen I had been picked on incessantly in class by Mr. Manners, the maths teacher, a master who disliked me intensely. It is safe to say that the dislike was mutual, for I hated him just as much as he clearly hated me. I don’t know if it was the fact that I was an American and my accent grated on him; but nothing I did in class was ever right and this character rode me hard all the time. If anyone had the aptitude to make one of his pupils feel small, this guy had it in spades. 

Well this day he drove me to my breaking point and I finally cracked as he had just added that proverbial last straw; and so I inadvisably – very inadvisably – told him to piss-off, using those very words.  Both he and the class were stunned.  I am sure that had he had the authority to do so, he would have skinned my arse there and then in front of the class; but as I told you, the teaching staff themselves were not allowed to cane boys and had to content themselves with the much lesser pleasure of issuing them with a punishment chit, which the offender had to place in a box outside the school secretary’s office and from which she prepared the punishment lists for the Monday, Wednesday and Friday evening beating sessions.

My heart sank as I saw that he had recommended an eighteen stroke beating for my offence; twelve cuts were par for the course but eighteen were rare and I saw that he really wanted his pint of blood from me. The list of attendees expected for that evening’s punishment session was posted as usual on the notice board outside the refectory and that particular Friday, my name stood there in solitary splendour on the Head-Boy’s list and I saw that there was no list for the Head-Master; so  mine was the sole arse to be beaten that evening.  And so at eight, in my shorts and gym vest, the appropriate attire, I knocked nervously on the door of the Head-Boy’s study and waited to be told to enter. 

The then Head-Boy, a guy called Simon Prosser, was also the captain of the school’s rugger team and a great all-round sportsman; all in all he was a very popular figure; and I have to say with my own devotion to the sport he was one of my own idols whom I admired tremendously. But this notwithstanding, here was the man who in his official role of Head-Boy was about to thrash my arse to ribbons by giving me eighteen cuts of his cane as stipulated on the punishment chit.

Simon Prosser also known as the Tosser, in view of his rumoured reputation for sexual adventures, opened the door and beckoned me to enter: “Well Stevens, this is our first meeting and I see that this evening you are my only – how shall I put it – client; so I shall have lots of time to devote to the question of the tender loving care which your arse, according to this punishment slip I have here in front of me, urgently needs.” I should just say here that boys and prefects alike, but obviously not the masters, always use the word arse when referring to a boy’s bottom. He smiled at me as uttered these words and then went on: “I see I am supposed to deliver no less than eighteen cuts of the cane to your naked posterior, which really is excessive. What on earth did you do to deserve such a severe beating?”

I pricked up my ears at the word supposed and as he did not seem in any hurry to get started skinning my arse, I poured out my heart to him and I have to say that he did listen sympathetically, before he finally told me to step out of my shorts and present my bare arse to him by bending across that same beating stool with which I was all too familiar from my visit to his predecessors over the years. I saw his eyes focus on my crotch, where my cock was already rising to the occasion, stimulated by the thought of what was about to happen to me. But I also noted that he too was clearly aroused sexually I could see from his trousers that tell-tale, uncontrollable bulge as his own cock began to harden; there was no doubt at all in my mind, that the process of beating and being beaten was an erotic act to which both parties’ bodies reacted automatically; well that was certainly true in the present case anyway.

Prosser came over to me and gently ran a soft, fondling hand over my waiting buns, a totally unexpected act, which I found very agreeable in spite of the position in which I found myself and which aroused me sexually even more, if that was possible, as I steeled myself for what I assumed would be an eighteen stroke caning.  Prosser very gently tapped his cane across the equator of my arse before applying a first resounding stroke.  It stung like hell as it always did, but I was not unduly worried as I had been beaten so many times in the past that I took it as one of the facts of life at Frogmore. But I was not at all looking forward to eighteen strokes in all, a number which I had never previously experienced.  Prosser continued and gave me five more strokes and then to my surprise stopped and said:  “Stevens, you know I have been thinking that your arse is just too attractive to be reduced to shreds by another twelve cuts of the cane and so unless you insist I continue with the cane, I think that I will stop there if you agree to an alternative which I am prepared to offer you; an alternative that will move you from being a junior into the senor echelons of this school.” 

And that is when that life changing act took place; not in words, but in actions. Taking my silence as a tacit agreement, Prosser revealed that his reputation for sexual prowess was indeed more than a rumour. He first rubbed some soothing cream into the welts he had created.  He then went across and locked the door of his study and said: “You know Stevens, I think that aged sixteen as you now are, and in the fifth, you need some introduction into the facts of sixth-form life at Frogmore. So unless you object, I propose to give you a little stimulation in lieu of the additional strokes I am supposed to give you.”

He did not specify what a little simulation, as he put it, involved; nor what he proposed to stimulate; nor how I was to be stimulated; all was left to my imagination; so I just kept silent, which he took to mean that I agreed to what he intended to do to me.  But as I was still bent over the stool with my arse naked in the air and having listened to the chit-chat about sexual matters which are the perennial topic of conversation of boys from age fourteen onwards, his suggestions left little to my imagination; in a word I knew that I was about to be fucked: an act I had heard described so many times in the interminable school-boy conversations about sex and with which I was familiar with in theory but not in practice.

And so I suppose I prepared myself, somewhat nervously, for a different kind of assault on my arse; one in which I would surrender my anal virginity to the Head-Boy. Frankly it seemed to me that it offered an excellent and instructive alternative to another dozen cuts of the cane; so why on earth should I object?  Moreover, it seemed to me that it was one of those things which just had to happen to me anyway; especially as I knew that my own awakening sexuality, until now dormant, was directed exclusively towards the male sex. I already knew that there were several older boys at Frogmore who consorted together as an outlet for their sexual tension and with my own proclivities I saw myself joining the ranks of lads who committed buggery with each other: in theory forbidden by the school rules but to which a blind eye was turned in view of the futility of trying to stamp out an act which was, in the main, conditioned by the exclusively all-male environment of the English public school.

Writing this memoir, years after the events recounted, I can safely say, that legislators of all hues can huff and puff and legislate till the cows come home, but sex, as the prime motivator in life, will never be controlled. One just has to accept that though sex is the primary source of life in both the the animal and plant kingdoms, among living creatures, we humans are that the only species who find sex, in addition to its fundamental function of procreation, as a pleasurable act. Sex is a key prime mover in life; it always has been and always will be and we may as well face the facts that that is the way it is. And let’s face it it is one of the most enjoyable, if not the most enjoyable, pastimes of life. So to deny ourselves this, the greatest of all pleasures, seems to me to be stupid, totally counterproductive and swimming against the current.

But to get back to what was about to be my own initiation into the joys of anal sex, I heard the Head-Boy undressing behind me. Then, obviously experienced in what he proposed to do to me, I felt his fingers massaging what I guess was more of the same cream as he had put onto my welts into my fundamental hole; a few seconds later, I felt the thrusting of his hard cock against my anal sphincter and him forcing himself gently but firmly inside of me.  I experienced a moment of pain followed by one of ecstatic elation as I felt, for the first time what was obviously a good-sized cock inside of me.  Frankly at that moment, it seemed the most natural thing in the world.  Prosser then went ahead and fucked me quite vigorously for the first time in my life and I enjoyed every moment of it.  And that is how I was introduced to the world of male-male sex.  I say male sex, rather than gay sex, because I am not at all sure that Prosser was gay. Like so many boys at public school he may well have found himself unable to resist having sex with his school mates out of sheer frustration at the total absence of females.  Anyway, Prosser’s sexual orientation mattered not one wit in the present circumstances as he certainly was an expert with his cock.     

Totally inexperienced as I then was, I just allowed him to do what he was doing to me until he finally withdrew himself and pulled me up from the stool over which I had still been bending as he was fucking me; then face to face, totally naked, but with no embarrassment at all considering that it was a first encounter between us, we both jerked ourselves off to a climax and ejaculated great goblets of our creamy fluid over each other; it just seemed the natural thing to do to complete the sex act we had just committed together.  I thought to myself, if this is punishment, then bring it on! After a short pause during which we caught our wind again, Prosser went into his private bathroom – a perk of the Head-Boy at Frogmore – to emerge with a couple of towels with which we wiped ourselves off.   But it was not yet over as he clearly wanted more; he took me by the shoulder, still naked as we now both were, and led me into his bedroom where he lay down on his back on his bed and asked me to fuck him kneeling there in front of him: “Go on Stevens, just do it; you have the equipment and it looks to be ready; so just go ahead and fuck me; you really do want to do it don’t you?”

 I was really shaken to the core at this request and even more so by the direct way he had told me what he wanted; somehow did not seem right that a fifth former should be asked to fuck his Head-Boy; but lust is a tremendous motivator, and being offered for the first time in my life an opportunity to sink my own meat into a real, live man was a request I could not resist; so I went ahead and did as he wanted. Prosser said to me that I should apply a little of the cream to my cock to facilitate entry, which I did. I should add that from the start of this, my introduction to anal sex, my own cock remained rock-hard and I had no problem in entering Prosser, with what I knew was a really good sized penis of which I was quite proud. And frankly that first fuck was truly one of the most memorable moments of my life; I had really no idea just how hard or how long I should pound his arse but once I had established a rhythmic beat, the whole act of copulation became quite natural and I just went on until I myself climaxed inside him. He moaned with pleasure as I became more and more insistent in my pounding and at the moment of my climax, we clung to each other, face to face like limpets in which position we remained for at least ten minutes. So there in a nutshell you have a blow-by-blow account of my first time

I myself knew at that very moment that I was gay: a homosexual; what Prosser had done to and for me had changed my life forever; my sex life could only be with other men; of that I had not the slightest doubt; even aged but sixteen as I then was when this life-changing event took place, I had no interest in wondering what it might be like to have sex with a woman.  That one act by Prosser set me on the road which I would subsequently follow and which would ultimately lead me to my career as a Male Escort. I may as well say here and now, that from this my first experience of gay sex, I simply loved both the active and passive parts equally; I enjoyed both fucking and being fucked. And to think that had I not lost my temper in class and told the teacher to piss off, I would never have been sent to the Head-Boy that day for punishment, which set of the chain of events which led to what I think of as my sexual epiphany. Was it worth a six-cut beating from Prosser to experience what he taught me that evening? Certainly it was; and I thanked my lucky stars that on my first experience I had been shafted by someone I thought of as really nice guy and a schoolmate whom I admired tremendously.

But to come back to the end of that incredible Friday evening with Prosser, after lying there side by side for an hour or so, I finally got up pulled back on my gym strip and went back to the changing room down the corridor where I put back on my school uniform before going back to Hanover House to my bed.  It was after lights-out by the time I got back and so I did not have to undergo the ritual of showing off of the stripes on my arse to my dorm mates; but I also considered myself lucky not have been caught by one of the House prefects who would certainly have insisted on giving my arse another dose of the cane.  As I left Prosser, lying there on his bed, he said: “You know, Stevens, for a beginner you’re a hell of a good fuck; we should try it again some time.” But it never happened as term ended just a few days later; I left for my annual trip back to Chicago for the summer and Prosser left Frogmore for the last time as he would be going onto university, to read law at Oxford in the autumn; and so we never did get together again. In fact, I never ever saw Prosser again after the school broke up for that long summer vacation but what happened that fateful Friday evening has remained with me forever.

CHAPTER 7

But to come back to my final two years at Frogmore when I was in the sixth-form, Clive Garrard, my closest friend and I had started having sex together immediately at the start of the new school year that September when we both moved into the lower sixth. Clive and I had become close friends we were both key members of the rugger team which drew us closer together and we just hit it off. You know how it is; two guys are attracted towards each other and things just go on from there. We had been class-mates and indeed house-mates as we both belonged to Hanover House, throughout our entire school careers, but it was not until we got into the fifth form and were both selected as junior members for the school rugger fifteen that we became really close. We were both attracted to one another sexually; but sleeping as we did in two different dormitories even though in the same House, seriously limited any mutual, experimental, sexual activity in which we might have wanted to indulge. So our joint sex acts, if you can call them that, were limited to the occasional wank together in the showers when we thought no one was around.

I suppose the key thing that had attracted us together as we entered the fifth form, was the fact that we were both keen rugger players who had been selected as juniors in the school fifteen and that we both had very muscular bodies which we exercised together regularly in the gym. Add to that the fact that Clive was one of the few English lads who, like me, had been circumcised, so that in the showers we were the only two guys with cut cocks in what was a sea of floppy foreskins.

Of course I told Clive about what had happened to me on the Saturday morning after my Friday night experience; but we were unable to take things any further as term ended on the following Tuesday and I went off first to York to my grandparents and then back to Chicago for the summer: a summer of utter sexual frustration for me as I really knew no one of my age on Chicago.  But at the start of the new term, things really got serious between Clive and me. As sixth formers we each had our own room for the first time, so that in an environment where everything is more or less public, things could now be done more discreetly and we managed to keep our liaison to ourselves.  It was helped by the fact that we were both in Hanover House.  Clive was anxious for me to teach him – almost the blind leading the blind as I really had very little direct practice – everything I had experienced with the now departed Prosser.

But Clive was an enthusiastic pupil and I an equally enthusiastic teacher; and so with the little I had to show him we very quickly became efficient practitioners of the ancient art of anal copulation. We both fucked each other on a regular basis and I think it is safe to say that we two were as near to being an item as any two public school boys can be;, although looking back on it now, I realise that our attraction was merely physical: pure lust; at the time it happened it was terrific for both of us. It is quite true that once you get over that initial hump of admitting to each other that you are going to have sex together and have then decided who is going to do what to whom, sex is like falling off a log; it is very easy and a darn sight less painful. And so for two years, we each satisfied the other’s needs by going at it hammer and tongs as often as we could.  In a word it was an exhilarating period in my life and I would not have missed it for the world.

Clive and I, as two muscular and well-equipped young studs, somehow managed to keep our regular, carnal communion secret for those two final years of our education at Frogmore.  How we avoided anyone even guessing what we were up to beats me now thinking back over it; but somehow we did and when we both finally left Frogmore two years later, it was two totally confident, sexually experienced young gay men who launched themselves wider world.  Neither Clive nor I had known that we were gay when we first became friends.  But he like me had long suspected that his sexual interests lay with other men and once we became sexually active together as we did in those final two years, both of us accepted the fact that, like it or not, we were a pair of died-in-the-wool homosexuals. It was rugger that had brought us together, but Clive was also a really brainy type, which I was not; he was top of the class in many subjects; I, in contrast, just scraped through most subjects and when we left my public exam results were just at the pass level; his  were first class. 

He then went on to read law at Cambridge, whilst I went back to Chicago. As our close friendship came to an end, I had no clear idea of what the future held for me. Our friendship came to an end as we left Frogmore, with each of us nursing an arse which was still burning from those truly awful beatings we had been given by the Headmaster and the Head-Boy just two days before we finally left Frogmore.  I think that we both saw that two year sexual interlude in our lives as part of the learning process: almost an extra-curricular subject to add to those which we were formally taught in class.  But school and all it had given us, was now over; neither Clive nor I ever looked back; our relationship was ended and we both accepted that we now had to move on to the next phase of our lives.

CHAPTER 8

Finally back in Chicago, I found myself under attack first from my father: “Why had I not tried harder at school and managed to get to Oxford or Cambridge?” When I pointed out to him that he himself had not gone to any university either in England or America and had nevertheless done really rather well for himself financially, he was, to say the least, displeased.  Then came the onslaught from my mother; male members of her family had for generations gone to that holy-of-holies, Harvard, one of the oldest universities in the USA; full of her own self-importance and coming from what she thought of as one of Boston’s leading families – whatever that might mean – she totally overestimated her string-pulling influence in her attempts to get me accepted by Harvard. It was not at all clear to me, how she herself settled on the course she decided I should study: economics, a subject in which I had not the slightest interest whatsoever.  But the only thing that mattered to her was that I should emerge three or so years later with a degree from that august seat of learning. However, when the admissions committee, or whoever oversaw the entry processes, saw my English exam results, I was left high and dry without even being called in for an interview. My mother was mortified that her efforts should have been spurned when she, coming from what she thought of as a leading old Boston family, had tried very hard, but unsuccessfully, to get me into Harvard. Frankly, I was indifferent and when the strings broke and I was left stranded, I could not have cared less.  What my parent did not understand was that I truly was not college material.  There is a saying that you cannot make a silk purse out of a sow’s ear and frankly my academic achievements fell into that category of animal anatomy.

But for my parents – or for my mother at least – it was absolutely out of the questions that I not pursue my education in one of the higher places of learning – he words –  and so with total personal indifference, but again thanks to my mother’s persistence, I found myself enrolled to study – my mother’s choice of subject – for the coming academic year at Notre Dame (rhymes with aim and not dam, by the way) University in South Bend, Indiana, a neighbouring state to Illinois and not all that far from Chicago. The only good thing I can say about that interlude in my life – and I choose the word interlude advisedly, as my sojourn there was really rather brief – is that the college was great on sports at which I excelled; and I quickly developed a great sex life, at which I also excelled, in the fraternity to which I became affiliated. However my time there was relatively short lived due to not one but two life-changing events which occurred within a short period of each other at the beginning of my second year at college.

Both my English paternal grandparents died of natural causes within a month of each other, leaving their entire estate to me.  As I mentioned earlier, my father and only child like me and his parents were not very close for reasons unknown to me, but whatever the problem it was sufficient for them to disinherit their only child and leave everything to me, their only grandson.  Now I had always known that my grandparents were well-heeled, but when the dust had settled and inheritance taxes had been paid, I was staggered to find that I had inherited a sum not far off $20 million in American money. They were a pair of wily old birds for their wills had stipulated that the entire estate passed to the surviving spouse and then, on his or her death to me, with the stipulation that their entire real-estate holdings in Yorkshire be sold and converted into cash by their executor, their solicitor in York. And so I inherited a great deal of cash without the problems associated with owning hundreds of acres of valuable farmland and buildings in another country, thousands of miles from where I lived.

I had no sooner digested the sad news of my grandparents passing, which was, of course tempered by the good news of the inheritance it had brought me, when my own father, aged only forty-eight and seemingly in good health, suddenly died of a heart attack.  My mother rang me to say that he had died in a hotel room in San Francisco where he went as regular as clockwork once a month on business. At my mother’s behest, I flew to California to take care of things, to learn to my surprise that he had died in the act of copulating with a lady in his hotel room.  Well the hotel room turned out to be an apartment which he rented on a regular basis in which he had installed a mistress, a charming lady whom I met.  What happened was that he was actually in the act of coitus with her when he suddenly died.  She, poor thing, was trapped under him and had had to stretch to reach the phone to call for help.

By the time I got there, he was already in the city morgue awaiting an autopsy, the results of which were that he had died of a myocardial infarction; he had survived his father (his mother had died first) by only two months. The coroner released his body very quickly and I arranged for it to be sent back to Chicago for burial.  I thanked my lucky stars that the San Francisco apartment was only rented, but I felt sorry for his lady-friend who had to find somewhere else to live; I am not sure how she earned her living, but that was really none of my business.  I flew back to Chicago having cleared matters up in San Francisco and saw no reason to burden my mother with the details of my father’s faithlessness. It was not that I felt much for my mother as frankly as we had never been close; but it seemed to me that to add the facts surrounding my father demise to her grief would be pointless; so as far as my mother and his colleagues at the company of which he had been CEO knew, he had died of a heart attack in his bed in a San Francisco hotel.

And now came the next surprise; my father turned out to have been fabulously wealthy; and I do mean fabulously! I knew we were not short of cash, but when the facts became known I could hardly believe my ears. But even more amazing than the value of his estate, was my father’s will; he left half of his entire fortune, including that Lakeshore Drive apartment, to me outright and the income from the other half to my mother but with no access to the considerable capital involved. There were two conditions attached to my mother’s legacy; on her death, the capital reverted to me in its entirety and similarly if she remarried, the capital immediately reverted to me and all income from it hitherto paid to her ceased.  So quite incredibly, I was ultimately the sole beneficiary of my father’s wealth which after inheritance taxes amounted to a staggering sum just over $100 million.

I was dumbstruck to learn how rich I had suddenly become and I did wonder how, starting from nothing, he had managed to accrue such an amazing sum legally by working in a company, albeit in the top position.  However mine not to question how, but thankfully to take my inheritance.  But I did ponder on the sort of relationship my parents had had with each other in view of the surprising but not super-generous way he had treated his wife; and that business in San Francisco also kept me wondering.  The capital providing the income for my mother, was managed by a firm of financial experts, of whom I had never heard, but in whom my father clearly had had great confidence; in his will he suggested that I allow them to continue to manage my own wealth, which I decided to do as I myself had not a clue about finance and investments. I offered to let my mother continue living in the Chicago apartment for as long as she wished; but she declined. With my father’s death and free from any ties with the city of Chicago, which she hated, she decided (did I detect a sigh of relief in her voice when she told me    of her intentions?) to go back and live with her mother in the old family house in Boston. And so with no other family in Chicago and my mother and grandmother nearly nine hundred miles to the east, I found myself foot-loose and fancy free in the city of my birth: a city which I loved.

Free from any financial worries and having no need to earn a living, I took the bull by the horns and dropped out of college in Indiana.  I had only gone there at my mother’s nagging insistence and the subject I was studying, economics, I found as dull as ditchwater. Looking at myself in that metaphorical mirror, I accepted the fact that I was not at all college material and should try to find something else in life to keep me occupied: but what?  And just believe me that I was not at that moment, thinking only about sex; although sex was a sine qua non – an essential condition – of my life, I was relieved that I did not have to explain my sexual orientation to my parents; I did wonder what my mother would think or say if I told her that her only offspring was a practising homosexual; but under the present radically changed circumstances I saw no reason to bother her with such details.

The first thing I did was to sell our – now my – huge condominium apartment with the lake view; it was just too big for any needs I could ever see myself having; and anyway I hated its rather sterile edge-of-town location; and as for the view of Lake Michigan; well you already know my views on that!  And so, wanting to be more at the heart of things, I rented a spacious top floor apartment with two beds and two baths and a roof terrace in that triangle formed by Lakeshore Drive and North Michigan Avenue just above The Loop.  Having done that, I desperately needed to get my sex-life organised again and up and running so to speak. The few contacts I had made I had left in South Bend when I dropped out of college there and so I found myself more or less back to square one in the fucking stakes, a situation which I could not allow to continue for long. I knew hardly anyone at all in Chicago anymore, due to my prolonged, forced absence at school in England; so I asked around in various bars and located a private up-market gym, with what was generally considered a swinging reputation. And it is true for after a couple of weeks when the regulars had seen in the showers what I had to offer, I was invited into that holy-of-holies, the naked work-out room, where well developed young studs like me flaunted their wares.

CHAPTER 9

It was there at the gym that I met Miguel Gonzalez, a totally assimilated Mexican immigrant, who worked in the art department of an advertising agency. Miguel was one of the handsomest guys I had ever seen in my life.  Like many all mixed race people from Latin America, his skin was an exquisite, light-tan colour and stretched flawlessly without a blemish  over a superb set of muscles; it completely blew me away.  We first saw each other one evening late in the showers; we were alone together shortly before the gym closed for the night.  We were both about the same height, just over six feet tall, and had very similar, muscular physiques; but most importantly, we were both very well endowed where it really counts in that we both had what by any standard had to be considered as exceptional cocks: exceptional in two ways; they were big: some seven inches in length when soft and beautifully cut to show off our respective heads and rims; but additionally we both had the luck to be endowed with rubbery meat, which looked good even when soft and hanging here over our balls. I tried to imagine what Miguel would look like when he was hard and raring to go. I felt sure that he was as gay as I was, for he had one earring, one nipple ring and had had all his pubic hair removed to display his man-meat to its maximum advantage; this he had adorned with a single gold cock-ring of the type which fits over the root of both cock and scrotum; I was utterly entranced by what I saw; here was a man who was proud of his body and endowments and obviously was not ashamed to make the best of them.

I think that it was looking at Miguel that evening when I first realised that I was only attracted to exceptional looking young studs who displayed the same characteristics as I had myself: good muscles and a big attractive-looking penis. So we sort of introduced ourselves, naked as we were under the running water.  I saw that my shower companion’s eyes were focused on the same part of my anatomy as mine were on his; in a word we were both clearly fascinated by the other’s credentials. Couple this key attraction with the fact that I was completely smitten by the beauty of Miguel’s physique and you can well see why I did not want things to end there; I just knew for the moment I met him that I wanted things to go on from there and quickly; not to mince words, I knew that I wanted to have sex with this guy, for he was a very attractive, fuckable hunk; I just prayed that the feeling was mutual. So encouraged by the keen visual interest Miguel was obviously taking in my cock, I took the initiative as we were dressing and said: “I don’t know about you, but I’m really ravenous after my work-out tonight; Fancy going somewhere and getting a bite to eat?”  To my utter joy, he took up my suggestion without any hesitation and few minutes later found us in a pizza parlour, just a few doors away from the gym.  And so we talked as strangers do and conducted that choreography of words aimed at learning as much about one’s companion as one could.  And it was only then that we exchanged names: Miguel Gonzalez and Andrew Stevens; I told him to call me Andy.

Our meal finished, I said to Miguel: “Look, I live not far from here; want to some back for a drink to my place?” And then that worn-out cliché of a phrase which nevertheless says it all: “We can get to know one another a bit better.”  We walked back to the block where I lived; it was a portered block and the doorman who I am sure was also gay said good evening and gave me a long knowing look which said it all.

“You really do have a great place here,” said Miguel as I motioned to him to sit down and told him to make himself comfortable while I went to the kitchen to fetch some beer.  When I returned bearing the beer a couple of minutes later, to my great surprise and equally great delight, I found my guest standing there totally naked and sporting the most attractive of erections I had ever seen in my life. It was almost as if he was posing for an erotic portrait; or even better; a sculpture in marble. As I re-entered the room, his cock, which by its sheer majesty totally dominated his figure and was clearly in charge of the situation, had risen and adopted that perfect, self-supporting position at 45 degrees to his stomach and was ready for action. I don’t know whether he thought I should have been embarrassed by his behaviour but I was most certainly not.  In fact, I could barely wait until I felt his rock-hard monument inside me.

“I took you at your word.” he said, as he advanced towards me in all his gorgeous nudity.  Then to my utter surprise he came right up to me, put his arms around my shoulders and kissed me full on the mouth.  “Look here, I don’t believe in wasting valuable fucking time. So let’s just cut to the chase; put the drinks down and get your clothes off and let’s just get on with it; we both know what we want to fuck each other senseless; so why are we wasting time?”  I had never ever in my many encounters with other guys met anyone who was quite so direct and who, in one brief sentence had summed up what he saw as the end-game of our meeting: to fuck each other; and of course he was dead right. And so I did as he suggested and, for the second time that evening, revealed to him yet again my all; and I am happy to say to say that my cock, with that mind of its own which the male sex-organ has, had decided to play ball and had sprung to rigid attention; it was every bit as ready to perform its duty as was his. So there we stood looking at each other; two – and I include myself here, with no false modesty as I count myself a pretty good specimen of young masculinity – muscular, young males with rigid, flagpole-straight meat, just raring to go.

There was a brief pause during which Miguel sized up what was now on offer, whilst I did nothing other than stand there. It was my apartment but he had led the way and so I thought it only right that he should be the master of ceremonies. He was as decisive in his next move as he had been so far as he pushed me onto my back on the living room table, pulled me forward so that my arse was more or less on the edge with my legs now hanging down towards before saying: “OK now I always practise safe sex, even with guys I know; so I always use a condom and lots of lube so that we both get a good and comfortable fuck.” He then left me there whilst he fished around in the back pocket of his discarded trousers and produced two flat packs of Fukit brand condoms each contain two rubbers and two sachets of lubricant. He tossed one of the packs onto the table, opened the other and handed me one of the rubbers and said: “Why don’t you put this on now, as my guess is that when we cum, you will produce a hell of a lot of juice which can make an awful mess of your place; so roll on the rubber and let’s catch it when it comes.” 

This sounded like very good sense to me and I did as he had suggested and watched him as he rolled the other rubber onto his own cock which he then anointed liberally with the lube from the sachet; he then came across to me and asked me to put my feet on the edge of the table to gain access to my anus so that he could give my hole a dose of the same lubricant.  I was very impressed by the methodical way he did things, in spite of the fact that we were obviously both raring to go; but I much appreciated the care he was taking with the preparation for our ultimate union and he clearly knew exactly what he was doing. Once he was satisfied with his efforts so far, he now came and lifted my legs over his shoulders, thereby spreading my buns and giving him clear access to my hole, before pushing the tip of his rubber clad cock against my anal sphincter.   I did not even attempt to resist him as I wanted as much as he did to feel his magnificent piece of fuck-meat inside of me. Once he had got his cock-head inside me and my anal muscles were gripping his hard shaft directly beneath his magnificently defined cock-head, he then very firmly and in one long, slow and very satisfying movement gave me the full length of his cock, finally bottoming his pelvis against my arse. “You OK?” he asked, as he paused for a few seconds before going on to give me one of the greatest fucks I had ever had,   

Some guys say that size does not matter, but believe me, when you feel a really big, hard penis deep inside you, filling out your passage, it is a sublime sensation. In spite of his huge size and obvious desire to fuck me, Miguel was as considerate in this as he had been in his meticulous preparation prior to penetration.  He did not indulge at all in that frenetic pumping one so often sees in porn-videos of guys indulging in gay sex. Miguel’s technique was to make use of the entire length of his tool the whole time; and believe me when it came to it, length was not in short supply, as he must have approached ten inches now that he was completely hard. With each stroke he almost, but not quite, withdrew himself completely before thrusting himself to his full depth inside me yet again. This is not to say that Miguel was in any way inhibited in what the was doing for he quickly proved himself a master in the oft not-so-gentle art of copulation; he gradually increased his power and the speed of his delivery as he himself became ever more erotically aroused, moving on towards his climax. Frankly, although I had been fucked dozens of times both by my first lover, Clive Garrard at Frogmore and subsequently by various guys with whom I had had sex, I had never before experienced anything quite like Miguel’s delivery; and I just sensed that due to his efforts we were going to reach that moment of perfection where we both achieved orgasm together. And when that exquisite moment arrived – why does it always have to be so very brief? – I had, thanks to him, the greatest orgasm I had ever had in my life.  There was no doubt about it, Miguel was a real pro when it came to handling his cock; he was, for me, absolutely the nec plus ultra of anal-sex operators: totally unequalled and I guessed unbeatable. And he had been right about my wearing a condom even though I was playing the role of bottom in our first coupling; I produced the largest emission of sperm I had ever done, thanks entirely to his extraordinary technique.

We lay together in post-coital bliss. I was still rock-hard and Miguel lay there on top of me with his man-meat still deep inside me and like that we lay there together recovering from the exertions of our first coupling. With Miguel on top of me, I absolutely rejoiced in feeling his muscular body pressed firmly against mine. And so we lay together, luxuriating in the mutual feel of our bodies in contact until suddenly, after about ten minutes rest, Miguel suddenly withdrew himself from me, got up and pulled me up from where I had been lying on my back. He said nothing as he swung me up from my back and left me sitting on h edge of the table. He reached across the table and retrieved the second packet of Fukits, tore it open and handed me a fresh rubber indicating that I should roll it onto my cock. I pulled off the first rubber which was now bulging with my copious emission, tied a knot in it and rolled on my second condom of the evening.  He did the same  and then swung me around and force me face down onto the table telling me to spread my legs;  I then felt him applying  a second dose of  lubricant to my hole, before a few seconds later he again thrust himself into me from the rear.

I won’t dwell on the details of Miguel’s second performance of the evening, save to say that it was just as great as what he had just delivered to me. Miguel was without any doubt at all, one of the greatest cocks-men ever.  He just knew how to use his magnificent endowment both to his own advantage and to his partner’s pleasure. He again brought both of us to intense, simultaneous orgasms, accompanied with equally huge emissions of sperm the like of which I had never before experienced. It truly was my most memorable sexual encounter to date: an occasion to remember. I would happily have allowed him to fuck me yet again if he had so wished, but he had other plans.

“Up get Andy; come on stir yourself; you cannot expect to loll around all night when you have work to do. You have had the pleasure – at least I hope it was a pleasure – of enjoying my efforts so far and it’s now up to you to do your part. Sex for me is a give-and-take business and I have so far given and you have taken; so I now want you to give and let me take.” So there it was; he could have not have been clearer. But I was, of course, only too happy to oblige, for the thought of fucking such a gorgeous hunk was something most guys only every dreamed of.  Remember that it was he who had taken the initiative and I had gone along with it. But I was no shrinking violet myself and now that the boot was on the other foot, I intended to show Miguel that I had a delivery service at least equal to his.  It was not only that I wanted to show him that knew how to handle my own meat, but I desperately wanted to develop an ongoing relationship with him and not allow our first coupling to become just another one-night-stand.

“Miguel, you really are a terrific cocks-man, the likes of whom I have, quite frankly, hitherto never experienced. Now let me try to show you that I can live up to your high standards as I play the role of top. Now I think after your energetic performance, something a little gentler might be in order to end this first evening together; so if you would like to move with me next door, we can continue our communing in the comfort of my bed.”  I took him by the shoulder and led him into my bedroom where I pushed him gently onto his back on my bed.  Then taking a leaf out of his book, I prepared him for penetration in the same way as he had done for me.  I opened the drawer of my bedside table where I kept a good supply of condoms and lubricants, handed him a rubber and rolled one onto my own cock. Then, taking a leaf out of his book, I meticulously lubricated his hole before anointing my own erection with the same lubricant. Then ready and eager as I was by then to fuck him, I spread his legs and asked him to bend his knees before penetrating him, as he had done me, in one long smooth movement. I then gave him what I think was a really good return fuck in the mission position.  

I can say with some pride that my performance was at least the equal of his and that thanks to my own considerable endowment I was able to give him a truly monumental fuck. Miguel moaned with pleasure as I progressively increased both the strength and speed of my strokes and he urged me not to stop; when we finally reached a climax, again together as I had held back until I could seen that he that he was about to explode and shoot his load, we each had an unbelievably intense orgasm; for me the longest I had ever experienced. This time it was I who lay on top of him and in that position we must have both fallen asleep for the next thing I knew was that it was six next morning and I was in bed with this this gorgeously beautiful, tan-coloured stud asleep at my side.   He suddenly awoke and turned, saw me and said: “That Andrew was one hell of a time we had together last night.”

That is how my friendship and sexual relationship with Miguel Gonzalez began. We saw each other regularly in the gym and our sex life became unbelievably active as we both lusted after the other.  In many ways it looked like the perfect partnership; but I think that we both saw that it was just sheer, carnal lust which brought us together.  We both had exceptional bodies and sexual equipment and few other guys were capable of delivering such intense and punchy sex as we two were; but that beyond that, spiritually, something was lacking.  But anyway we both enjoyed what we did together and we made hay whilst he sun was shining; and why not as we both enjoyed having sex together, which I confess we had to distraction.

CHAPTER 10

But it was this liaison with Miguel which ultimately led me to being what I am today: a Male Escort. He and I had always agreed that we did not own each other and that we were free to have sex with other guys which we both, in fact, did. But Miguel, as my principal partner, who was was always one for an adventure, suggested that we go out together cruising one evening and see if we could pick up a third guy for a one night, three man stand.  “It would be a bit of fun and something different,” was the way he put it. When I say cruising I use the word metaphorically as neither of us had a car at that time – I couldn’t even drive ; but Miguel, ever the animator, suggested that we go to what was considered the top, gay-pick-up bar in town, which was located in the Howard House Hotel, a small, private owned hotel which was not far from where I actually lived. How I was unaware of this place I do not know; well anyway, one evening along we went and installed ourselves in the bar, which was a very upmarket place.

Miguel told me that this hotel attracted out-of-town businessmen who preferred the intimacy of this smaller place to the modern chain hotels downtown. According to him there were lots of young businessmen, foot-loose and fancy free away from their homes and wives during the week, who welcomed a little sexual adventure when away from home. It was a sort of a reverse of the old adage: when the cat’s away the mice will play. Anyway according to Miguel, there were lots of regular men who liked what was usually called anal stimulation: getting their arse fucked by another man, as this was a service as that their wives could not provide. Just how Miguel knew all this I have no idea.

I got the clear impression that this was not the first time that Miguel had been in this place as he seemed to know the principal bar tender, a guy whom he called Pete.  Pete motioned with his head to a youngish guy at the other end of the bar and sure enough a few minutes later this fellow approached us. Now dressed as we were, it was fairly clear that he was talking to a pair of gays. Anyway, he offered to buy us a drink before coming quickly to the point. So a few minutes later we found ourselves stripped naked in his room enjoying and evening à trois together. As Miguel had predicted what his man really wanted was to have his arse reamed by a good sized cock and the two of us of course, obliged him.

Well that first visit led to others and we always found ourselves a partner for a one night stand and always with someone who was staying at the hotel. As I lived not far away and as I really enjoyed playing the field, I took to going to the Howard House Bar by myself where I usually found an agreeable partner for the evening. And all too often as Miguel had said, the guy in question really wanted nothing more than a little anal sex from me. But I did not mind as I really loved fucking butt. But what these visits brought home to me was the number of men, both straight and gay, who were looking for an occasional partner; and most of the guys I fucked in my visits there were, in fact, straight and just wanted a little anal sex: something their wives could not give them.

By now Pete, the barman, knew me too; one evening he came up to me as I was sizing up the talent and whispered: “See that young guy at the other end down there? Well he has just asked me to ask you how much you charge for your services.”  So I somewhat indignantly told Pete I was not in the business of selling myself and that I came there just to have a pick-up for the evening. So Pete said:  “I know that; and you know that; but he doesn’t and he thinks you are a pro.  So just give me a figure and I’ll go and bounce it off him and see what he says. Look at this way; you want a pick-up for this evening; he looks like an OK guy and takes you for a pro; so why not just go along with it; so come on now, stud, name your price! But if you want to chicken out, just give me figure which will put him off.”

That is exactly what I did; or at least that is what I thought I had done, as I told Pete to say that my rate was $500 cash for two hours of therapy and $250 for each additional hour. That, I thought, would surely put the guy off; but how wrong I was; this character had obviously taken a shine to me, for Pete came back a few minutes later and said: “Right; you’re on; room 414 in ten minutes.”  I gazed down the bar and looked at my client, which was what I suppose he had now become; he looked back at me and raised his glass as he stood up from the bar and left; presumably to go to his room.  I marvelled that anyone would want to pay me, an unknown quantity, $500 to fuck him.  I finished my drink and communicated my thoughts to Pete, that this guy must be off his rocker, to which Pete replied: “Maybe and maybe not; you know Andy, you’re one hell of a good looking young stud and the way you dress does have a sort of come-on look about it; just take a look in a mirror and you will see that anyone with half and eye can see that you have a great package. You know quite honestly if you’re ever desperate I wouldn’t mind a session with you myself. And what the fuck, you came in here tonight as you so often do, looking for a one-night-stand; well this time you’ve hit the jackpot, because not only have you got what you wanted, but you’re getting paid to do what you really like doing. My god, I would change places with you like a shot if I had your looks and your equipment.”

“You know Pete, I’m not sure that I want to go ahead with this; I don’t need $500 and I don’t like the idea of getting paid for a service which I would happily have given this guy for free.  So I don’t think I’ll go up to his room after all.”

“Don’t be an idiot Andy. You can’t chicken out of this now that I have set it up to for you, Come on; be sensible; this guy is a regular client of the hotel and he looks really nice; so what more do you want? You came here tonight with a view to finding a casual fuck as you regularly do; so just go up there and give the guy what he wants and if you don’t want his dough, then just do it for free. Come on Andy, that’s what you want anyway; that’s what you came here tonight for; so stop philosophising and searching your soul about the rights and wrongs of being paid for sex; just get your arse and cock up there to his room and do the deed; it’s what he wants and it’s what you want too; so where’s the problem?”

Pete’s arguments convinced me of my obligation to go and serve this guy; so a few minutes later I rang the bell on the door of his room to be ushered in by him to what was a full suite.  My client, as I now thought of him, was a young man in his early thirties; he was well-set-up and really very handsome; just the type whom I would have been overjoyed to have picked up in my normal manner; but somehow the question of cash had added a vaguely rotten odour to the whole occasion, which I found hard to shake off. He looked at me and said: “Hi; come on in and let’s get acquainted: I’m Hal and you are?” So on the spur of the moment I pulled a name out of the air and said: “Jeremy; pleased to meet you!”

Ask me not why I did not give him my  proper name, Andrew, or Andy as my friends called me; but I didn’t;  and Jeremy is the professional name which has stuck with me ever since. I say profession although I not sure that the rather lucrative and enjoyable activity into which I gradually allowed myself to slip merits being called such. I did not realise it at that moment, but this encounter with Hal, was to prove a turning point in my life; I was in a situation where aged just twenty-one as I then was, I was about to fuck a guy for cash; but as it turned out, sex was only a part of what happened in that hotel room, I found myself introduced into a world which, I, naïve as always, had not know existed.

Hal seemed a really nice guy and took the lead as he said: “Look Jeremy, I know that this is a professional arrangement between you and me tonight, so I would like to get the rather sordid question of money question of money over and done with before we start.” And with that he handed me $750 dollars in crisp new $50 bills.  I was extremely embarrassed at his largesse for it implied that he intended to engage my service for three hours; and so I said, or rather I started to say, that I really did not want any money at all, only to be cut short by Hal; and so it never got said.

“Well now that we have got that settled let’s talk turkey. Jeremy I am not actually what I suspect you think I am; I am not gay as I guess you probably are; but I do from time to time enjoy having sex with another man.  You see, I am from out of town and I come to Chicago about once a month for a few days on business and although I am happily married with a lovely wife and two children and have a great regular sex life, I still hanker after something else.  Look here Jeremy, I’ll level with you; at school and later at college I really enjoyed having  sex with other guys, even though I am basically straight and the fact of the matter is that I still enjoy having my arse reamed out from time to time by another man; an act which my wife clearly cannot accomplish. And so when I am away from home each month, I take the opportunity of finding someone like you who can play ball with me.  But I have to tell you that anal sex is not my only weakness, for I also like to have my backside beaten before sex.  You see I’m one of those guys who actually  enjoys having his ass beaten; it’s actually known as consensual corporal punishment or CCP for short; and believe  me there are quite a lot of guys out there who are just like me and who indulge in this – well let’s call it what it is –  perversion. So when I slipped you the extra $250 tonight, it was not because I wanted you to fuck the living daylights out of me for three straight hours, but because I hoped you might be willing to give my arse a good beating before you fucked me.”

“And just let me say, Jeremy, that just looking at you, even fully dressed as you still are, I think from that lovely bulging crotch of yours, you are really going to be able to deliver the goods when you get down to it.  So look here Jeremy, I know that you were looking for a normal type pick- up in the bar tonight, as most local Male Escorts (he used that expression telling me what he evidently had taken me to be) know it is really the top place in town for high-class, male, sexual encounters. So as soon as I saw you, I found you immediately very attractive and that’s why I slipped the bar-tender fifty to solicit your services on my behalf. So in some ways I feel a bit guilty in having got you here under somewhat false pretences or at least hoping for services over and above those normally provided by Male Escorts. So now that you have the full facts, are you willing to meet my needs? If you don’t want to get involved in CCP, then we can call the whole thing off and you can keep the cash anyway for your trouble. So what’s the deal? Will you or won’t you?”

You will probably think me super-naïve to be unaware that CCP existed; but until that moment, I honestly didn’t.  From my many, painful, personal experiences of the cane applied to my own backside at Frogmore, I thought he must be stark, raving mad to want someone to flog his arse for him. But I have to say, never having been made a prefect at Frogmore and having always been on the receiving rather than the giving and of the cane or birch, I was intrigued at the thought of beating someone else’s arse: an act that until that moment I had honestly never even thought of.  I confess with some shame, that even just thinking then about the possibility of inflicting pain on someone, was already making my cock harden in my pants; and I remembered vividly how often both I personally and the person beating me at the time, either a prefect or the Head-Boy or my Housemaster at Frogmore, had normally not been able to stop our cocks hardening as he thrashed my bare arse. And I recalled quite vividly how very often after being beaten at school. I had gone straight to bed and jerked myself off to liberate my own sexual tensions.

So although I was acutely aware of the erotic effects of corporal punishment on the beaten, this was the first time that I might actually experience the potential effect it might have on me in the role of the beater rather than in my hitherto role. So in word I was, by chance, in a unique position; it was an opportunity just too invitingly intriguing to miss. Hal thought that I was a regular Male Escort and as such had paid the absurd sum I had pulled out of thin air for what I had assumed would be my sexual services; but then I was asked to thrash his arse before I went on to shaft him. Frankly, although the whole thing had come out of the blue, I decided that I would go along with it.  I had suddenly realised that I might never ever again have the opportunity to shred another guy’s backside; and I felt that as a connoisseur of the pain which an arse beating delivers, I owed it to myself to have at least one go of delivering what I knew was a very painful experience to someone else. And anyway, Hal was a really well set-up guy who would surely be a good fuck whatever the outcome of my efforts at beating his arse. And so having warned him that I was sailing into totally unchartered waters never having beaten anyone before, I said yes.

As he heard my agreement, I saw a look of relief flash across his face; and I understood that this guy truly did want to have his arse shredded and then fucked. There was a slight pause as he digested what I had said and then he smiled and said: “Well now that that’s all settled shall strip for action? Jeremy I have to tell you that in addition to my love of occasional male sex and CCP, I do also like looking at naked, young studs like you and I would like us both to be completely naked when you beat me.”

But now I saw a fly in the ointment; beat him with what exactly? “Oh I forgot to tell you that I always carry and old razor strop which I bought in an antique shop; it’s by far the easiest thing to pack when I travel and believe me Jeremy, when well applied it is fucking painful. So you will have the pleasure of beating my backside with an implement which in days of yore was part of the spanking armoury of lots of American households.”

I told him that I had been at school in England and had a great deal of personal experience of what a well-beaten arse felt like and that I would do my very best, on this my maiden beating, to see that I left him with an arse of which I was proud; but also one which, in terms of pain, also met his expectations; of course I had no idea what his expectations were.  I only knew just how fucking painful the cane or birch could be and I wondered if a razor strap would allow me to develop the same sharp pain with which I was so horribly familiar. So we stripped off and stood admiring each other; he gave me a wolf whistle as he admired my body and especially my cock which was already fully erect at attention and was at least nine inches long. Hal too was not a bad looking guy in the buff; I guess he was ten years older than me; but with a really nicely cut cock which frankly, at first sight, I hoped he might want to use on me later. In a word I really liked Hal but I shuddered inwardly at the thought of what I was about to do to him with his razor strop.  But he was he client on this occasion and the client was king; so mine to do his bidding.

Hal then produced the strop from his suitcase and I saw that it was a formidable instruments of punishment instrument made of very thick, but nevertheless, supple leather.  It had a shaped wooden handle at one end and the edges of the leather had been chamfered away so they were rounded and would not cut into the flesh with which they were shortly destined to mate.  I guess that the leather part itself was about two feet or possibly a little longer so that with the handle one had an implement approaching thirty inches in length. I really did wonder whether this was actually an implement for sharpening the now long-abandoned cut-throat razor; or was it just a fantasy rendering specifically destined for beating arse. Anyway, in my hand it felt well-balanced and I saw no problem in meeting Hal’s, in my eyes, peculiarly perverse needs. I thought to myself as I contemplated what I was going to do to him, that when push came to shove, as it now had, I was no different to all those prefects at Frogmore who had, over the years, thrashed my arse; I wondered if all men had a hidden sadistic streak in them which could be awakened if the opportunity arose. In fact, in spite of my initial reaction, I found myself looking forward to making my maiden beating and shredding my client’s naked butt.

“So Jeremy, shall we get on with it?  I would like you to begin with twelve really good swats across my backside and then we will take it from there.”  I wondered how many cuts Hal had in mind as he said this as he then, with obvious previous experience, pulled forward a chair and bent across it presenting me with his muscular looking buns.  But before he did that he went to his suitcase from which he extracted a jock strap which he put on. “I always wear this when I take a beating as I don’t want my balls to get in the way and a jock just keeps them out of harm’s way. It will also allow you to be totally uninhibited when you apply he strop, which is what I want; I want really to feel the pain of the strop with every stroke you give me; so don’t even think of holding back; just apply the strop with the maximum force you can.”

Armed with this exhortation, I positioned myself to his left, raised he strop above my head and brought it down with a tremendous slap on his expectant arse.  I was somewhat unnerved by the crack the strop made as it found its target, but he took the blow without a murmur. “That was a good start Jeremy, so please just go on and give me eleven more just like it.”  I paused a second, to see that my first blow had already left a broad, angry, red mark right across his two buns, And from I then went on and gave him the twelve he had requested, by which time his arse was bright  red. I have to admit, with a certain sense of shame at my feelings, that once I got into the swing of things I found myself really enjoying what I was doing.  With all twelve strokes delivered I stood back to admire my handiwork.  And with those twelve strokes, which I was soon to discover was for starters, I had more or less covered the whole area of Hal’s buns.  I suppose I had created in my maiden beating the equivalent of what at Frogmore was known as a well-beaten arse; but unlike the cane, which leaves distinct welts across its target, the strop just leaves a red mark where it lands; but free of well-placed, parallel welts, which were the pride of prefects and the Head-Boy at Frogmore, the whole of Hal’s arse had taken on a bright-red, fiery hue, which I thought might better be described as a well-roasted arse. 

But well-beaten or well roasted, one thing seemed clear to me; I had managed to deliver a really painful beating which is what Hal had wanted.  However, I had apparently not fully satisfied his craving for pain; after a few moments’ pause he said: “Well Jeremy, that was absolutely great for starters but I think I would like another twelve.”  I confess that I was astonished at his request for I would have thought that with his backside in the inflamed state I had created he would surely have had enough; but no; he wanted more.  As I steeled myself to continue, my mind flashed back to that ghastly occasion in my last days at Frogmore, when my friend Clive and I had each been given a twenty-four stroke thrashing for smoking and drinking in a public house.  I remembered vividly the excruciating pain which the Headmaster had visited on my backside with his birch and sighing inwardly when it was over – or so I had thought – only to be told that we were both to receive another twelve cuts of the senior cane on top of the birching.  Now here I was with an almost analogous situation; Hal had taken twelve and was now, unbelievably asking for another twelve; the beaten was asking the beater to continue! What was this man thinking about? How could he stand what he was asking me to do to him?

But there was no doubt about Hal’s desire to continue as he said: “Come on Jeremy, don’t be shy; just give me another twelve as that is exactly what I want.” So I did exactly as he asked and I can tell you that by the time I had finished with him, I myself was in such a state of sexual arousal that my cock seemed longer and harder than I had ever hitherto known it and I was already dripping pre-cum. By the time I had finished, Hal’s backside was deep-red all over and bruises were already developing, but here was no blood; the strop did not break the skin. I guess that the strop is a bit like the classic American paddle: very painful but causing not much surface damage and therefore you can go on and on giving stroke after stroke, building up pain to untenable levels. Whether with my twenty-four strokes I had arrived at that level, I have no idea; but evidently Hal was now satisfied. As he now stood up I could see that the beating had had an erotic effect on him too, for his cock was thrusting against his jock-strap which was wet through with his emissions. “I guess I need to get rid of this,” he said looking down at the soggy pouch between his legs, “I don’t think we need it anymore.” so he just stepped out of this skimpy item of clothing and allowed his rampant cock to assume its full erect position. Like me, he too was dripping with cum.

So we stood there looking at each other without any embarrassment in view of what we had just done together. After a moment he said: “Well Jeremy, for a first time effort that was an absolutely superb performance by you;  you know, I cannot remember a thrashing that I enjoyed quite so much; and believe me, I’ve had lots of experience. You really are a true pro and if you are as good at what we are to do next it will be a brilliant evening together. But my God, I’m now as hungry as a horse so why don’t I call room service and order something to eat for us before we continue. Look while I place the order, why don’t you look in the fridge in the kitchenette there (remember we were in a suite) and see what there is available to drink.”

I did as he suggested and emerged with a bottle of champagne, which he told me to open:  “We can toast a successful beginning to this evening’s activities.” He said.  We sat around, both of us in the all-together, drinking the champagne, which I had only rarely ever tasted previously, when the doorbell rang announcing the arrival of the room service.  Hal was totally unembarrassed, as stark naked as he still was, although his member had by now calmed itself somewhat, he opened the door and let the waiter enter.  The waiter, a very handsome young guy, to his credit, did not blink an eyelid when he saw the pair of us totally naked; it was as if it was a daily occurrence – and for all I knew, perhaps it was! He arranged the table and served the food he had brought but as he was doing this I noticed that he did flash me an admiring look or two and I wondered if he was gay; not that it mattered as attractive though he was, he was not in my sights on that occasion and we were certainly not prepared for a threesome.  Anyway, we ate and drank and to avoid disturbance Hal pushed the device trolley out into the hall and hung the do not disturb sign on the door knob.

So we had now got to the moment where I was about to serve Hal in the way I had thought when we met in the bar; and although he had congratulated me on my prowess with the razor strop, which had gone really well in spite of my own initial misgivings, I now felt very confident and on firm ground as I knew that I could deliver an experience to him which, with no false modesty, would be as good as it gets.  I found myself hardening again at the thought of what I was about to do to him in a few seconds; just with the thought, my cock was already as hard as a rock and raring to go.  What I was about to do, which was to fuck Hal’s butt, was one of the activities I enjoyed most in life and at which I was very proficient;  although it was not something I did professionally as Hal clearly thought; so here I was actually being paid by this guy to do something which I would happily have done for free. Hal looked at me with eager anticipation in his eyes, as he took in visually the sheer magnificence of my cock; and make no mistake, even though I say it myself, I do look terrific when I am ready to fuck with my cock rampant in all its glory. He said: “Gee Jeremy, you really are something, you know: the sexual equivalent of the Washington Monument; I can’t wait to feel your meat inside of me; I don’t know what you usually do but for starters I would like it lying flat on my back on the bed.” I noticed immediately that he had said: for starters, which implied that this was just the beginning of an evening of sex which is I exactly what I had been looking for when I went into the bar at the Howard that evening: an agreeable one-night stand with someone who I could fuck with pleasure and who, hopefully, would return the favour.  And in view of the beating I had just inflicted on him, I could well understand why he wanted the front entry position; frankly with his arse in the roasted state in which it now was, I marvelled that he could even bare to lie down at all; but he did; and he was the client; so mine not to reason why.

I had taken a real liking to Hal and was determined to give him the best fuck he had ever had in his life. He watched me closely as I rolled on a condom rubber and then applied a liberal dose of lubricant to my rubber clad cock. I then handed him the second rubber from the packet and suggested that he might like to roll it onto himself with a view to containing his emission when it came as I was sure it would – in spades.  This was something I had taken to doing systematically ever since being given the idea by Miguel. He was, of course, quite right: anal intercourse is a very satisfying experience but just so very messy.  I then asked Hal to put his feet on the bed and bend his knees so that I could lube up his vital parts. As I prepared him for intercourse, he commented on the meticulous way I prepared us both for the act I was about to undertake, saying he had never seen such care in the preparation before.  I told him that good lubrication was the key to a really good fuck as I now intended to demonstrate to him.

So the moment had finally arrived and I knelt down in front of him, pushed the tip of my cock against his sphincter. I was pleased to see that Hal had a really tight anus, which is exactly how I liked it; I hate fucking a guy with a sloppy entrance; for me a really satisfactory fuck is when my partner grips my shaft and I can truly feel myself deep inside of him. I had no idea how his previous partners had gone about things, but I was determined to take Hal with me all the way to a full orgasm simultaneous with my own, which I intended to have with my full length deep inside of him.  I don’t know what he was expecting, but as I pumped away at him, I gave him the longest stroke possible each time; he moaned with obvious pleasure and when I saw he was on the verge of his climax, I finally withdrew myself completely, waited a split second before plunging myself for that final time as deeply and as hard as I could back inside of him. This was a technique I had developed to try always to give my partner a great orgasm; and with Hal, things went exactly as planned and we both climaxed together in massively explosive orgasms. I don’t know if it was the extreme state of sexual arousal in which I found myself due to the beating I had just given him, but my own emission was huge; I just pumped what seemed liked, a never ending stream of my own thick creamy sperm into the rubber deep inside of Hal’s rectum; he too, to my great satisfaction of a job well done, simultaneously jerked out his own spunk in spades, with what I can but term explosive force, into the rubber he was wearing. It truly was a moment to savour and could not have been any better. I know I was primarily there as a paid professional to serve Hal’s needs but I felt very satisfied that we had both had such had amazing orgasms; for without orgasm, the sex act becomes meaningless.

“My god Jeremy, you really do know how to give a guy what he needs. I’ve never before experienced anything quite like what you have just   done to me; that, young man, was a truly stellar, mind-blowing performance; where the hell did you learn to fuck like that; you really are a true pro you know.  Believe me Jeremy, I have had sex with lots of other guys but never have I had an experience like that which you have just given me; it truly was amazing; it makes you realise what sex is all about and what a sublime business sex can be. Talk about anal stimulation which is what I really wanted; well your efforts just took that to unimaginable heights. You must have a really faithful and devoted clientele if you always perform like that; you really are at the top of your profession. Now, if you are up to it after that performance, I would just love you to take me again but this time from the rear; do you think that you could managed that or are you worn out with all that effort?”

In fact I was anything but worn out, as I had enjoyed fucking him just as much as he had evidently enjoyed being fucked by me. And let’s face it, at the end of the day I am human with all the human failings; and after that shower of praise I was completely flattered by him. But don’t get me wrong; as I went ahead and did as he requested, it was not only because of the flattery, as I really did want to fuck the guy again.  I suppose I could have come clean to Hal there and then and told him that I was not the experienced pro he took me for; but I said nothing and allowed him to continue believing that he had hired a professional Male Escort for the evening.  From his point of view, did it matter? As far as

I could see, not at all, as he was obviously more than satisfied with my performance; and to out it crudely; he felt he was getting his money’s worth. 

As I prepared to shaft him for the second time, I shuddered inwardly as I surveyed the damage which I had done to his arse, which was now showing bruising as a result of my efforts with the strop. It beat me how the guy could bear even to allow me touch him from the rear, let alone fuck him; but stand it he did; and without a murmur of pain; and once again we both enjoyed intense orgasms as we climaxed simultaneously. Hal told me that he had never been fucked by anyone before who had brought him to such unimaginable heights of sexual pleasure as I had succeeded in doing: “Jeremy, you really have the golden touch; you have brought the art of anal stimulation to its peak.” I have to say that I did feel very pleased with myself at such fulsome praise of my sexual prowess.  I had always thought that I was a very competent cocks-man, possibly because every time I fucked a guy I put my heart and soul into what I was doing and did not allow it to become the banal, self-gratifying act which is so often is. This fact had obviously come through to Hal; but never before had I had such praise heaped upon me.

But how did this extraordinary evening end?  Well I had hoped that after my efforts Hal would want to give me a return round.  As I told you earlier, I had always viewed gay sex as a partnership: a two-way, give and take business; I enjoyed being fucked by my partner just as much as I enjoyed fucking him.  But this evening it was not to be; Hal had said that he wanted anal stimulation preceded by a thrashing and that is exactly what happened; there it ended as he showed no desire to give me that return round which I so much hoped he would. But as I say, he was my supposed client for that evening and his wishes were sovereign; so matters ended there; at least they ended there between him and me; but that evening’s events were to have far-reaching repercussions which never entered my head at the time; as I left Hal’s suite that evening, I was totally unaware of the chain of events to which my one-night stand with Hal would eventually lead.

“Jeremy what you did for me this evening was really great; can you give me one of your cards so that I can contact you again the next time I am in town?”  He clearly thought that I would have some sort of professional card which I handed out, which, of course, I did not.  In fact I did not even have a personal card.  But instead of taking this opening to come clean to him, I told him that I did not have a card on me that evening and finished up giving him my cell-phone number.

CHAPTER 11

It was less than a week later that I received a call on my cell-phone from an unknown caller: “Hi, am I speaking to Jeremy?”  I almost said there was no one by that name at this number when it suddenly hit me that I was the Jeremy he wanted to talk to.  So having confirmed to him that I was, in fact, the fictitious Jeremy, he went on: “Well Jeremy, I got your name from a mutual friend, a recent client of yours I believe who extolled the services which you offered as being second to none. Look here, I’m in town for a few days and at a bit of a loose end in the evenings  and in view of the glowing accounts I have heard about you, I would really like to meet you and get to know you myself  and get to learn more about the services you offer; might that be possible?”

So here I had another footloose and fancy-free guy, evidently looking for sex and possibly more, for what else could he want from what Hal – it had to be Hal as there was no one else who knew the name Jeremy – had evidently told him. Anyway, I decided to play hard to get for a moment so I decide to play hard-ball with this guy and said:” What services of mine, if I have any, might you be interested in? And if I might ask who gave you my phone number and told you about me? And if we were to get together, what exactly would you be looking for?”

“Gee Jeremy you really are making me jump through the hoop here; look  I’d rather not say who gave me your number except that it was one of your recent clients, who, as I to you, was very, very satisfied with what you did for him; so can we let it go at that?  Anyway I gather from him that you are a very experienced Male Escort and as such I suppose you know the sort of services that your potential clients are looking for.  So if I have to spell it out to you Jeremy, I’m in the market for a little anal stimulation if you see what I mean; and to be quite clear, I’m not thinking in terms of an enema, which would be anal irrigation without the stimulation I am looking for. (He laughed at his own little joke, which showed in a way how nervous he was) But my contact tells me that you are also very proficient at CCP (he used that abbreviation; so Hal had evidently had told him the entire story) and I could be interested in that are too. Look here Jeremy, I know your fees and they are OK so there is no problem there.  So why don’t we do this? Let’s meet in the bar of my hotel and I’ll be right at the left hand end of the bar so that you can size me up before you decide on whether we should meet face- to –face; so how about that as an idea?”

So there it was; Hal had been so convinced that I was a professional escort, that he had passed on my name – or rather my pseudonym – and praised me to high heaven to this guy (very gratifying I can tell you); so here I was talking on the phone with a guy I did not know from Adam about fucking his arse and possibly thrashing it too. I really was in a slight quandary as to what I should do.  This was a new experience for me: a sight unseen prospect; it was not that I objected to having sex with someone I did not know; quite the contrary as that was the purpose of my frequent fishing trips to the Howard bar, where the unknown added spice to life; but here I had a man on the other end of the line who was clearly raring to go and I had no idea who he was or what he looked like: none at all.  Usually at the Howard it was a case of looking first and then moving towards the kill; in other words I had already decided I liked the look of my quarry before approaching him; and let’s face it, first appearances are very important; but here it was the reverse; I was being contacted by someone I did not know.

I needed to sell myself for sex as much as I needed a hole in my head as I was already a man of independent means as it was often loftily put. Yet somehow the thought that my services were worth something intrigued me.  I did not need the money, but by charging for my services, I somehow became a legitimate operator: a professional Male Escort. But I also realised that I had left Hal the other evening $750 dollars richer, which somehow, put a high value on my services, which was a gratifying fact. In fact in suggesting base fee of $500 for two hours plus $250 for each additional hour I had aimed at putting Hal off; but my – to my mind anyway – absurdly high prices had not had the desired effect.

If Bartender Pete had not stuck his oar in, I might well have finished up with Hal anyway that evening, as I had gone specifically to my regular stamping ground at the Howard Hotel with the sole objective of picking up some attractive looking guy for evening of casual sex. But Pete’s interference had changed all that and had taken me into unknown territory, to do something I had never before even contemplated: selling myself for sex. And then, when I had had a chance to come clean with Hal and tell him that I was not at all what he thought, I had not done so and had finally left him – after a marvellous evening of sex – thinking that I was a professional Male Escort. So in a way, the dilemma I was now facing was partly of my own making. Hal must have thought that in recommending me to his friend, he was doing us both a favour; what more natural than to tell your friend that you had found the most wonderful professional cocks-man in Chicago and recommend him to check it out the next time he was in town.

Anyway, in for a dime in for a dollar, so I finally said yes to the guy. We arranged to meet the following evening in his hotel, which was – yes you guessed it – the Howard.  I sensed a feeling of relief in his voice as he gave me the (unneeded) instructions as to how to find the hotel. He then went on to say that he really would like a little CCP and would I be sure to bring the necessary implement with me; he obviously assumed that it was part of the standard equipment of my profession. Well it turned out that what he preferred was the cane and so I said that I would bring one along with me. It then suddenly hit me that I had no idea at all of where I could buy a punishment cane in Chicago and if I managed to find one, how I would get it into the hotel without raising eyebrows? It is one thing walking into a hotel using a walking stick, but quite another brandishing a school cane. 

Finding a cane proved no problem as an internet search turned up one of those kinky stores, located in a seedy part of the Loop,  which cater for any and every perversion know to man.  They had a large selection of rattan canes, exactly of the kind with which my own arse was all too familiar, and so I bought six of different calibres, all with straight handles bound in leather for a good grip; but this surprisingly resourceful store had no simple case in which I could house the canes enabling me decently to enter a hotel with my purchases.  Anyway the guy who sold me the canes suggested that I go a few doors down where there was a junk shop and rummage around here in the hope that something would come to light.  This turned out to be an inspired suggestion, for barely had I started my search when I came across a long tubular container made of expensive-looking, polished leather complete with a leather cap at one end and a shoulder strap. This handsome looking object, the shopkeeper told me, was an old-fashioned carrying case formerly used by architects for carting around their large, rolled-up drawings. I really felt that the gods were with me on this mission for I had found both canes and a means of transporting them.

And so so I carried my newly acquired treasures back to my apartment, where I almost gave myself an orgasm trying out the canes, one after the other, on a cushion over a chair.  Although my own arse was all too  familiar with the doubtful – to me anyway – joy which a sound whacking could bring to the recipient, I had never before actually held a cane in my hand, let alone been in a position where I was shortly about to use it for its reputed therapeutic properties. I had not been appointed a prefect at Frogmore and had therefore only ever been on the receiving end of that much used implement; not surprisingly I was now truly aroused by the thought of being able to exercise my skill on a willing arse. So to ensure that I did not disgrace myself that evening, I spent quite some time practising on the cushion, as I wanted my client to think that I was an experienced purveyor of corporal punishment.  I had already realised that with a rattan cane I could potentially do much more damage to the guy’s arse than had been the case with Hal’s razor strop. So as an utter novice in the art of caning – and believe me it truly is an art – it seemed to me that I had to judge just how much force I could bring to bear on the guy’s naked backside to satisfy his perverse desire for pain, but at the same time not make a bloody mess of his arse.

I arrived early at the Howard that evening. It was Pete’s night off and another barman, whom I did not know, was on duty. As I arrived, the far left-hand end of the bar was empty and I installed myself at the other end, leaning my leather case against the bar, the bartender came across and asked me what wanted to drink; looking at the case propped against the bar, asked me if I had caught any fish; presumably he thought the case contained fishing tackle.  Anyway I gave him a cryptic reply, saying that I had not yet caught anything, but that I would shortly do so.  He served me my drink and went away perplexed.  It was around seven when my second client ever, arrived in the bar and parked himself as he had said at the far end and ordered a drink. I was relieved to see that he was a youngish man, about Hal’s age and frankly was just the sort of guy whom, at first sight, I would have targeted as a potential one-night-stander  had I been on my normal fishing trip – let’s call it that – at the Howard.  It then suddenly hit me that I did not know this guy’s name; he had addressed me as Jeremy on the phone but for some reason had not got around to mentioning his own name.

I do not know if he realised that I was his partner for the evening as he gazed along he bar, which was still very quiet as it was rather early. Anyway, someone had to make the first move and perforce it had to be me, so I picked up my case and moved over towards him.  I guess he realised that I was the contact he was waiting for and as I came closer to him he said; “I’m guessing that you might be Jeremy; am I right?”  I nodded my head in agreement at which he held out his hand and said: “My name’s Dave; I’m really pleased that you could make it Jeremy.”  I could see whilst he was talking that his eyes were taking in the man who was in front of him who had been highly recommended by his friend;   from the agreeable expression which his face immediately adopted, I could see that he liked what he saw. Like most guys who are looking for a sex partner, his eyes took in my crotch, which as ever showed a very attractive bulge of the substantial package it contained. He offered me a drink and we exchanged a few pleasantries before he come round to the business at hand very quickly.

“Well Jeremy, I gather from your appearance that we are – how shall I put it? – on for this evening, so if you would just give me ten minutes to prepare myself, and then come to my suite on the fourth floor.”

 He gave me the door number and to my surprise it was the self same suite that Hal had occupied a few days previously.  I rang the bell and he opened the door and to my immense surprise – I suppose shock might be a better word – I found myself confronted with a stark-naked Dave; clearly a man who was not slow of the mark and equally clearly a man who was not afraid to show what he had to offer; and I can tell you, this guy’s credentials were well worth seeing. Hal had been well equipped but Dave was in a different league; clearly he was a guy who looked after himself physically as his body was finely honed to masculine perfection; it was the sort of physique which only comes from hours of serious training in the gym; and as for his sexual potential, well he had a cock which any guy would be proud to own; but here I admit that I was slightly relieved that it was not quite as big as mine. It was nevertheless a very attractive fuck-stick if ever there was one, and I desperately hoped that as the evening progressed he would want to let me sample his technique.  Little did he know that had we met by chance in the bar, I would have been deliriously happy to have a one-night-stand with him for free:  Dave was just so mouth-wateringly attractive that could feel my cock hardening in my pants as I stood there! I took all this in at first glance, standing here in the corridor with Dave holding the door open for me to enter.

Once in the room I felt totally overdressed; how could I feel any different with my client, stark naked, hovering over me? “Why don’t you make yourself more comfortable, Jeremy?”  Framed as a question, I realised that I had, in fact, just been given an order to strip. So with nothing to be ashamed of, I obliged him.  Dave looked at me with clear admiration in his eyes but nevertheless had a hungry look about him. I could tell from his manner that he was straining on that metaphorical leash to get down to the business of the evening, whatever that might be; I was sort of praying that he would find me sufficiently attractive attractive to want to explore my arse with that magnificent tool of his, which I noticed was already standing to attention; but I just stood here letting him admire the view as it were, without having any idea what the next move would be. Had it been a normal pick-up, then we would have been on a level playing field and I would have had no hesitation in making the next move, which would have been to get him to fuck me with that beautiful penis of his; but this was not a level playing field; Dave thought he was buying the services of a Male Escort, for which he was frankly paying through the nose; and as such it seemed to me that he should be entitled to dictate the rules of the game for the evening. He went on: “Jeremy, you really are something, I’ve been with quite a few Male Escorts in my time but never with one quite as well equipped as you.  So for starters can we open that treasure chest of goodies you have brought with you – referring of course to my cane carrier – and see what delights you have in store for me?”

“Dave, I have to come clean with you; when you said you wanted a CCP session with a cane, I was somewhat surprised as the cane is not much used here in the USA; it’s much more a British thing. So quite honestly, I’ve never been asked until now to use a cane. You see, in the past (and here I was actually telling the whole, but nevertheless, slightly misleading truth) I have just used a strap. I refrained from adding the word always as I did not want to lie to this guy, for whom I really did have the hots.  But as you said you wanted the cane, I’ve brought a selection of rattan canes which is what our British cousins use all the time in their co-called public-schools; so you can take your pick of what I have brought with me.”  I opened up the case of canes and allowed him to look them over.

Whilst he was examining them, I went on and added: “Anyway, Dave, although I have never actually wielded a cane myself, just for the record, I can tell you that I fully appreciate the sting that it can deliver. You see, I am half English myself and my English father sent me to an English public school where the cane never seemed to rest; I can tell you that I have lost count of the number of times when I was at school that I have got up from over the back of a chair, with my own arse thoroughly torched with the cane.  In fact the school I attended seemed to specialise in delivering what we all referred to as a well-beaten arse – sorry I mean ass, of course. I can tell you that in my time there, a succession of junior and senior prefects, head-boys, housemasters and the Headmaster himself were all consummate practitioners of wielding the cane, which they did regularly and vigorously with gay abandon. But look here, to be honest, as a receiver rather than a deliverer, I myself have no experience at all of wielding the cane myself, and so if you would rather not risk your own ass to the ministrations of a beginner, then we can call the whole thing off here and now, with no hard feelings on either side.”

Dave finished examining the canes, looked at me and said:  “Jeremy, you really are a very honest guy, and experienced or not with the cane, I simply cannot let you back out of our agreement; frankly Jeremy, you are easily the most attractive escort I have ever seen and I would mad not to let you show me just what you are capable of.  So let’s cut to the chase and go into the room next door, where I will kneel on my bed with my head on a pillow and you will take this cane (he handed me the one he had chosen) and give my arse – as  you seem to refer to it – a twelve cut beating for starters.”

I have to confess that it was with a slightly nervous feeling that I followed him into the bedroom where he adopted the position he had chosen for his session of CCP.  I found myself presented with a perfect bubble butt: two perfect, and as yet, undefiled globes. Speaking as somewhat of a connoisseur of that key part of the male anatomy, I was blown away by the sheer attractiveness of Dave’s arse; it was just crying out to be fucked and given half a chance, that is what I would have done; but that was not the way things were programmed for that evening where I was the servant and not the master. So first things first, as I prepared to give Dave’s backside the first stroke of the cane, the first of the twelve he wanted but which would also be my maiden stroke. Quite suddenly, as I looked at my target, all the reservations I had had about using the cane disappeared.  My mind went back to my school days, when it my arse which was being presented to be beaten and I recalled how countless prefects had tapped gently with their cane, on my naked buttocks deciding where to place the first cut before I heard he cane swish down through the air and with that sickening crack as it landed on my naked skin, to be followed a split second later by that inimitable, searing pain which only the cane is capable of delivering; and then the ten or so seconds pause, allowing me – or any other poor sod in the same position –fully to appreciate the effect of that first stroke; and then the leisurely succession of what always seemed to be ever more swingeing cuts as the beating continued; to be followed finally by the relief as I was told to get up and put back on my shorts.

I suppose contemplating what I was about to visit on Dave’s arse I saw the occasion as a sort of pay-back-moment for all the times I myself had been in the same position when at Frogmore.  But here was an important difference; Dave was a willing supplicant whereas at Frogmore I had had always been a hapless victim; someone being punished for some misdemeanour or other, real or imagined; I had never voluntarily offered my arse to anyone to be beaten as Dave was now doing. Anyway the fatidic moment had arrived and I raised the cane and brought it down with a resounding crack more or less at the mid-point – the equator if you wish – of Dave’s globes; he let out a loud cry; but of what – pleasure or pain?  I then went on and with a suitable appreciation pause between each stroke, gave Dave the twelve he requested. By the time I had finished I was very pleased indeed with my first efforts with the cane for I had managed to give him twelve perfectly placed stripes from the bottom of his back to the top of his legs.  Having given Dave the number of cuts he had requested, I stood back admiring my handiwork and waited for the next order.  Other than the odd groan or moan as I had applied the cane, Dave had remained silent as I proceeded with the caning.

He then said: “Well Jeremy to say that you claim you had never caned anyone before that was a great job you have just done on my ass. Frankly, I have been caned by quite a number of different escorts over the past couple of years; but I can tell you that not one of them knew how to lay on the cane he way you just did; you exceeded even my wildest expectations especially after the way you deprecated your own prowess and pleaded ignorance. Well if that truly was your maiden effort, then I wonder what you will be like after you have had a bit more practice. Anyway let’s press on.”  Dave had got up from his bed and was addressing me standing there directly in front of me as he said this; I could see that he was totally aroused by what I had done to him as his cock was still rock-hard and dripping  a little pre-cum; as I hasten to add was mine! In fact, at one stage I had been so aroused by what I was doing, that I feared for a moment that I was going to reach orgasm and shoot my load all over his arse.

He continued: “So what I would like you to do for me now Jeremy, is to give my ass a dose of that magnificent cock of yours and fuck me as hard as you can; what I want is a really powerful, no-holds-barred fuck. That my friend is exactly what my ass is just crying out for after the beating it has just had; so don’t even think of holding back; just go for it like a wild man; that’s what I want.” And then with no more ado, he knelt on the bed again and resumed more or less the position in which I had just thrashed him; he did however spread his legs a little more to give me easy access to his fundamental orifice. It suddenly hit me that my caning of Dave’s arse, to be followed by an immediate fuck of what I had just roasted, was exactly analogous to my own introduction, not to the cane, but to gay sex.  I remembered vividly that evening when the then Head-Boy, Simon Prosser had been supposed to give me eighteen cuts of the cane but then, after six strokes he had stopped and offered me a much more agreeable alternative to which I had agreed. And so my introduction to gay, anal sex had been that day, as Prosser had lubed up my arse, which he had just thrashed, and had then gone on to rob me of my anal virginity by giving me my first fuck: an act which had changed my life forever. So although today was slightly different, it was a double first for me as I had not only thrashed another man’s arse, but I was also going to fuck the very arse I had just roasted with the cane. I wondered if life as a Male Escort could ever get any better; and I was not even a true escort, remember.

Dave was waiting impatiently for me to act on his instructions. So telling him that I only practised safe sex, I rolled a condom from a Fukit twin pack onto my still hard cock, suggesting to him that he roll the second rubber onto his own member to catch his own emissions. I sort of thought that we both might make copious emissions by the time I had finished fucking him as we were both in a state of high arousal and I had every intention of taking him all the way to his own climax with my cock deep inside him at that magic moment of orgasm.  Then with no undue haste I first lubed up my own cock before turning my attention to Dave’s arse and anus with the Fukit lubricant. I then knelt down on the bed behind him and prepared myself for the moment of truth: the moment of penetration.  I have to say that I felt on much firmer ground than I had done earlier when handling the caning; Fucking butt was more or less my stock-in-trade; my cock was still rock-hard and at maximum length as I slid it smoothly and gently deep into Dave’s rectum.  I made my usual pause before beginning to fuck him properly; but as he had specifically asked for a vigorous approach, I gave him maximum power and maximum stroke-length from the word go. As I fucked him ever more vigorously, Dave urged me on to use more and more force as he really wanted his arse battered as hard as possible. Finally we both exploded together into simultaneous orgasms of great intensity and length, during which, as I had anticipated, we both produced seemingly endless streams of creamy cum.  I finally collapsed across Dave’s back with the effort I had expended and he was to tell me a few minutes later, when we had both recomposed ourselves that I had given him the greatest fuck he had ever had.

But the question uppermost in my mind at that moment was what was to happen next. Left to my own devices – the evening was far from over as far as I was concerned – I would have flipped Dave over and gone on to fuck him a second time in the mission position and then hoped that he would feel sufficiently aroused to wish to give me a return round, which is the thing I secretly most wanted him to do as I always saw gay sex as a two-way deal. But it was not be; evidently Dave had had enough of my ministrations with the beating and the one-time sex act and he called it a day; so with his profuse thanks for what for him had evidently been a great evening, I left the hotel clutching $750 in crisp new notes in my greasy paws; I speak metaphorically of course. Little did Dave know that I would have gladly handed him back his money in exchange for that return fuck I had so hoped he would give me.

It was still not late, only around eight, as I had been with Dave for little over an hour. I somehow felt let down; cheated and really still very randy by the way things had turned out.  Of course, I tried to rationalise to myself that I had done my job and had been paid as a professional Male Escort, which is what Dave thought I was; but that did nothing at all to ease the fact that I personally felt totally unfulfilled and dissatisfied after the encounter I had just had with Dave.  In sheer desperation, I went over to see Miguel with whom I had regular sex. When he let me into his apartment I was relieved to see that he was alone and so I was able to weep on his shoulder and he was more than willing to give my arse the fuck which I had so desired from Dave; of course it did not stop at that as we went on as we always did and I finished up drowning my sorrows in an orgy of gay sex with Miguel in his bed, where I awoke next morning to find myself alone as he had already gone off to work without waking me.

I had not told any of my acquaintances of my sexual adventures with Hal; but Miguel had been bursting with curiosity to hear how I had not only found myself inveigled by Pete into passing myself off as a professional Male Escort, but had also been cajoled into adding another string to my bow by acceding to the requests of my two clients for a dose of CCP. Miguel who was the guy among my regular partners with whom I had sex most often, was of the view – and he was right of course – that if I was being paid for my services, then the payer could call the shots.  But, a fount of all knowledge as he always was, he told me that usually Male Escorts are requested to do exactly what I had done, either with or without the CP bit; basically it was always the escort who provided the action for the client; he fucked them but they did not fuck him in return.  These guys paid Male Escorts basically became they wanted some anal stimulation; crudely out they wanted some guy to fuck their arses for them.  So Miguel thought that my two clients were absolutely typical; they were obviously regular users of the services of professional escorts and as they had thought that is what I was, they had treated me as such.

“Look Andy,” said Miguel, “You were being paid – and royally so – for   your services; so I think you just have to accept that that is how things function in that profession; you have to jump through their hoop but they do not have to reciprocate and jump through yours.  Andy, what you have just experienced is not at all the same as what you and I do together; we try to please each other, whereas such guys as you have just been with, have retained your professional services to please them; to satisfy their desires and perversities.  For them it is just a business deal; they tell you what they want; you deliver; they pay you; end of story. There is no emotion at all in it; and as for reciprocity; well just forget it.  But just let me ask you this; did you enjoy what you did for these two guys? Did you enjoy beating their asses? Did you enjoy fucking them?  If you did then I think you have got to be satisfied. You cannot compare what you have just done, with what happens when you – or indeed the two of us together as we have done several times – pick up some guy in the Howard for an evening of recreational sex. There we are all on a level playing field and can express our desires and influence what happens; but that is something you cannot do when you are just what amounts to nothing more than a hired help for the evening; you have to do the client’s bidding.  Remember the old saying Andy: He who pays the piper calls the tune. Frankly my friend, I think that you did OK for your maiden openings; the question is: what happens next?”

And here Miguel, perceptive as ever, had put his finger on the key point; frankly I had no idea what should happen next.  I had allow myself to become involved in something which I had not completely understood; I had been disappointed in one way that after giving each of my clients a really good dose of anal sex, my efforts had not aroused them enough to make them want to do the same for me. Sex apart, I had to admit to myself that in spite of my initial misgivings, it would be quite wrong to say that I had not enjoyed the experience.  Frankly I had found it quite exhilarating and erotically simulating to beat my first clients; it somehow seemed to compensate for all those beatings I had taken myself at Frogmore; and the anal sex I had had with them, was, as ever, a very satisfying experience; one which however many times it is repeated, just never fails to please. And then there was the additional bonus that I had fucked two guys whom I did not know from Adam, an experience I always enjoyed immensely, which was one of the main reasons I went on my fishing trips to the Howard bar; the unknown added a little spice and sense of adventure to life. I had listened to the wisdom of Miguel and taken on board what he had said; and I suppose I now realised that he was right. I had gone into my two affairs, let’s call them, thinking that they were the same any other gay sex liaison I had with any partner, known or unknown; but I now realised that I had completely misread the situation and that I had no real right to feel put out because things had not gone according to my preconceived plan. I was playing a totally different ball-game and the question I had to ask myself was whether I had enjoyed it, in spite of  what to me had been an  unsatisfactory outcome; in a word, did I want to play the game according to the rules?

CHAPTER 12 

After a great deal of soul searching, I decided that I would really like to go on with what I seemed to have allowed myself to slip by accident. I did not need the money as I was wealthy enough in my own right not to have to work; but as I had nothing to do most of the time it seemed an attractive sort of an idea; and let’s face it, I was totally devoted to gay sex, which was something I could not do without in my daily life.  With no need to earn my living, but having been paid twice for my services, I have to admit that here was a certain feeling of satisfaction that I could sell my sexual  services for such a high price; frankly it was moral boosting and my self esteem soared; and I did admit to myself that I had really enjoyed wielding the rod on the naked arses of my two clients to date.  I wondered ifI have a hidden sadistic streak inside myself. But if I were to go on, how would I do it? I had not the faintest idea of how to set about developing a Male Escort business; my only two clients to date had found me rather than by me soliciting their custom.  However, once again fate intervened in the form of yet another phone call; again it was from someone unknown, but with the important difference that this guy was local; I assumed him to be a business contact of either Hal or Dave, as only they knew my name, Jeremy, and had my phone number.  

“Hi, am I speaking to Jeremy?”  I confirmed that he was. “Well Hi again; you don’t  know me, but my name is Craig Kolanek, I’m the Chief Financial Officer of – and he named a company which meant nothing to me – but here’s the thing; I got your name and number from a business associate of mine, who said that you were a real pro at your job.”  I interrupted him here to ask what job that would be. He continued: “Well Jeremy, let’s be clear to avoid any misunderstanding; and I do hope that I did not misunderstand my contact who gave me your number, but he said you are what is usually referred to as Male Escort.  Is that right? Do I have the right Jeremy and the right number or am I way of course?”

“Mr Kolanek; you are not off course at all; I am the Jeremy your contact was referring to and I am, in fact, as he told you a Male Escort.”  As I said that, I realised that for the first time I had tagged myself as a professional escort, just as Hal and Dave had seen me; so I had now acknowledged the fact to Kolanek, and more importantly to myself, that I was a Male Escort. “So Mr. Kolanek, what can I do for you?” 

There was a pause as Kolanek gathered his thoughts before putting them into words: “Well Jeremy, the thing is this and I presume that we are now speaking in strictest confidentiality.”  I confirmed that we were and wondered how he was going to get round to the delicate subject of what he wanted me to do to him. Even when it’s on  a professional basis as it then was, or even when I pick someone up for a one-night-stand of recreational sex, there is always that little stumbling block to overcome before we get down to talking turkey and cut to the chase. “Well Jeremy, it’s like this; I’m a happily married guy with a nice wife whom I love and two lovely kids and we, live in a nice house and so on; but from, time to time I feel I need a little more than my wife can give me in terms of sex; don’t get me wrong, my wife and I have a great sex life together, but there is always a little more that I would like which my wife simply cannot give me;  I am sure you understand what I mean; which is why I have contacted you.”  I understood all too well as he went on: “So from time to time I quite like a little stimulation from another man; if you see what I mean.”

“Mr. Kolanek, I understand exactly what that you are referring to what is usually called anal stimulation; if I may out things crudely so that we both understand understand one another clearly; calling a spade a spade, you want me to fuck your arse; is that correct?  But is there anything else you want from me so that we both understand where we stand? Do you want to have a return bout with me for instance?”

“Jeremy, you really are very direct, but you have said all that needs to be said. As you say I want some young man to fuck me, which is something my wife cannot do but which is something I need from time to time and so I need someone like you to help me relieve my tension. Other than that there is nothing; so I am what I suppose is known in the trade as a bottom and I do not want to play the role of top with you.  So Jeremy, now that we both understand where we stand, I know your fees and they are OK and will settle with you in cash. The only thing to settle is where and when we meet; look here, I wonder if you could come to my office at close of business tomorrow, say a little after five; just come into the main entrance, ask for me; I’ll alert the doorman that I have a late appointment and he will show you up to my suite on the top floor where we can conduct our business completely undisturbed.”

He gave me the exact street address which was in the downtown business district.  So it was quite clear what Kolanek expected and CCP did not appear to enter into the equation this time. As his was my first assignment where I had acknowledged the fact to both myself my third client that I was a Male Escort, I decided to get some business cards printed.  I found a small print shop which could make me the cards within two hours and ordered five hundred.  I thought long and hard as to what I would say on my card before settling on the following:

Jeremy

Male Escort

Stimulation and Discipline

By appointment only 

Telephone xxxxxxxxx 

When I went to pick up the cards around five that afternoon, the young man in the shop looked at me with hungry eyes, which had first been quite clearly focused on my crotch, handed me the cards and said, very directly: “You serious about what it says here?”  To which I replied that I was. “Well how about you give me quickie in the back room and I’ll give you the cards for free?”

 I guess this guy was about my age and he was really a very good looking type, well set up with blond hair. He wore stylish clothes as I did and I guessed that he was gay. And that is how I had a pleasant and completely unexpected adventure in the back room of his print shop. Kenneth Best (his business was called Best Print) as he told me his name was, turned out to be a very muscular young stud and was as gay as a coot; I enjoyed fucking his arse, which was our initial deal, but then as we had become more relaxed with each other, he asked me if I would like him to do the same for me. As you know, I like reciprocity and Ken, as he told me everyone called him, had a magnificent penis: a very impressive piece of meat indeed; and he certainly knew how to use it. And so what had set off as a simple one way deal – an arse fuck in exchange for 500 free business cards – turned into a two man fuck fest which went on until eight that evening.  We finally finished up going out to a pizza joint to finish off the evening together; or so I had thought; Ken however, had other ideas.

“Listen Jeremy, tonight is my club night and I wondered if you would like to come with me and check out the local talent.”  Having no fixed plans for the rest of the evening I saw no reason not go along with his idea and so off we went to his club.  It was, of course, a gay club and a quite exclusive one at that; Ken had to show his membership card and sign me in as his guest; but once inside, I have to say that I really did have a great time. Miguel and had I pulled a number of one-night stands with bored businessmen at the Howard Hotel and had a three man evening of recreational sex; but this place was in a different league and it was the first time that I had experienced gay group-sex in the raw; and when I say in the raw, I really mean in the rawest of the raw, as everything seemed possible.

I had always dressed fashionably, not hiding my assets in anyway, but here many of the guys were wearing the most outrageous of clothing: figure fitting shirts, open to the waist displaying muscular pecs, often with pierced nipples and several guys were wearing something I had hitherto never seen: backless, leather pants with their two buns exposed. Ken told me that these guys all wore jock straps to keep their kit in order but leaving open that all important access to their anuses. And as I took in this extraordinary, highly erotic scene, I saw that several guys had already paired off and were having anal sex together just standing there.  But the thing that struck me was just how muscular and fit looking everyone was. I remarked on this to Ken who told me that to become a member you had first to undergo and pass a totally nude interview with the committee who basically only accepted muscular guys with big packages. “You see,” said Ken, “The idea is to maintain a very exclusive gay-muscle club where everything goes; and so no one who does not meet the criteria of the committee is accepted as a member. In a word, weedy guys with little cocks are excluded; so what you are looking at here is the crème de la crème of muscular gay Chicago.  Most of these guys are really the hardest of the hard-core gays around these parts and just live for sex; and then there are the likes of me; guys with the right physique who like sex a lot but are much less extreme. But don’t worry Andy; if you want to join, you’d be accepted right away.”  Frankly I was not sure that I did want to become a member but being there I saw no reason for once not to take advantage of what was on offer.

Ken, who was obviously well-known at the club, got four other guys together and the six of us then moved off to a private room where we all stripped off and had what I can but call a no-holds-barred fuckathon; you name it; we did it. I had never been fucked so many times in such a short period as I was by these guys; not that it was one sided, for I had never fucked so many holes in quick succession as I did that evening.  It all began with what Ken called a warming-up round, where we each gave each other a five stroke thrust of our cocks; so I  semi-fucked – if there is such a concept; by which I mean that one never came anywhere near to orgasm – five other guys and was in turn accorded the same treatment by each of them; so in quick succession I sampled five different cocks and five anuses, including Ken’s with which I was already fairly familiar; and to be fair, Ken was in a class by himself, when it came to handling his fuck-stick; like me he was, as I told you earlier, very well endowed; and let’s face it, say what you will, size is important when it comes to sex.  Anyway, after that introduction I fucked and was fucked by three of the guys to climax each time, before we attempted to carry out a six man effort.

And so it went on and on. It was three in the morning before we left the place and I then staggered home and dropped into my bed. Looking back on the whole business, it seemed totally unreal that the simple act of ordering five hundred visiting cards could have set of such a chain of events leading to such an unbelievably phantasmagorical evening as I had just experienced. I marvel how I – or for that matter Ken too – had stood the course; remember that before we ever went to the club, he and I been vigorously engaged in gay sex for several hours. But sex is a great motivator and once you get started and are psyched up, aroused and on the roll, it can be difficult to stop.  You might think that after a few rounds that your man-juice would have run dry, but that does not seem to be the case, for even a short pause is enough to give you fuel for another round. 

I really had enjoyed the experience with Ken at his club but I had no wish ever to repeat it. I am a gay man and a very active one at that and I was just embarking on a profession where I would fuck men I didn’t even know for a living. There is a world of difference between what I did with Hal and Dave or what I would do with my third client next evening and the raw, powerful, hardcore, gay sex which I had just experienced.  For me it was one of those things you needed to experience just once – but never again. I felt a little sad about Ken as he and I had had a great time together and I really liked the guy; but if he was into the extremes of sex he had just shown me on a regular basis, then I felt our potential friendship had to be left to wither. It had been a terrific one nightstand stand with Ken which I had greatly enjoyed and one hell of an experience for me at the club; but I had my first true client to worry about at the moment and that had already begun to exercise my mind; and so Ken and I parted company without any plans for another meeting.

CHAPTER 13

Next evening having completely recovered from the sexual excesses the night before, I duly presented myself at the reception of Craig Kolanek’s company, which like so many American businesses was located in a magnificent modern building in the Chicago business district. The name of the company was emblazoned on the door but told me nothing about what it did as I was a complete ignoramus when it came to commerce; but somehow that name was vaguely familiar; and then it suddenly hit me; this was the very company which my late father had so successfully run as CEO for many years and which had furnished him, and now me as his heir, with a large part of my inheritance; now here I was about to offer my services to a man whom I suppose might have been one of his senior colleagues.  The doorman showed me to the lift and as he pressed the button for the top floor, he told me that Mr. Kolanek himself would meet me at the lift. He looked with interested curiosity at my tubular leather cane holder which I had over my shoulder together with a small satchel of supplies. I had decided to bring my canes with me just in case my new client had not totally divulged what he wanted. It had occurred to me that as he had received my name from either Hal or Dave, both of whom were devotees of CCP, he might just possibly be of the same persuasion.  I must admit that I did have slight butterflies in my stomach as the lift stopped and I waited for the door to open to give me my first sight of my client.

Sumptuous is an understatement for the furnishings of the top floor lobby where Craig Kolanek had his office suite.  As the lift door opened, I found myself looking at a really rather handsome man, well set up, who could not have been more than thirty years old. In a word he had exactly the visual profile that had I seen him by himself in the Howard Bar, I would have had no hesitation in trying to pick him up.  I guess he owed his present position by belonging to that group of financial young whiz-kids whom one reads about in the press and who are multi-millionaires by the time they are thirty With a smile, he held out his hand to me and said: “Hi Jeremy; I’m Gary Kolanek; come on let’s go straight to my office.”

Kolanek’s office was little short of  spectacular, dominated by a huge modern  rosewood (I guess) desk and a matching conference table and chairs, all sitting on what was obviously a top-quality, luxury, fitted-carpet; the whole environment simply oozed money. On the desk were were that cliché of obligatory accessories: two silver photo frames containing pictures of his wife and his two small children: both boys. He offered me a drink which I declined and he got down to business right away. Our initial discussion was very easy; it can be a bit difficult even when both of you know what is required, for desires have to be put into action, but in this case there was no hanging around as Kolanek came straight to the point.

 “Jeremy, I think we both know what it is I am looking for from you this evening; as I told you over the phone and as you can see from the photos, I am really a happy family man, but from time to time I do, nevertheless enjoy a little male-to-male sex.  You see, when I was at college, I was really a bit of a stud myself, and I actually enjoyed sex with both men and women.  I finally settled down to the classic heterosexual relationship with my wife; but I still have a hankering from time to time for what I suppose is gay sex; and right now is one those times; which is why I called you.  Let me tell you that you come with the highest of recommendations; and just looking at you Jeremy, I have to say that at first sight, you do look a very attractive, sexy, young man; but as the old saying has it, the proof of the pudding is the eating, so shall we sample it together?”

He went and locked door to his office and then ushered me into a second room in which there was what I suppose was called a day-bed, two easy chairs and a table; leading off from this room a bathroom was visible through a partially open door. I suppose that this unexpected appendage to a normal office was justified if he had to work late at night concluding some deal or other and had to sleep in the office. But common sense told me its main use was for the purpose for which we had now entered it: to allow him to indulge in his desire for gay sex in complete privacy and away from home.  We had no sooner entered this inner sanctum than he started stripping of his clothes and motioned to me to do the same.  I was amazed how matter-of-fact he seemed to be about the intimate sexual act in which we were to indulge together, for he showed not the slightest sign of embarrassment as he shed his last item of clothing and stood before me totally naked.  Well all I can say is that if he was pleased with what he saw when I stood naked in front of him, I was literally blown away by the sheer masculine beauty of this man who was about to pay me, what to my mind was an exorbitant fee, to fuck his arse.

It was clear that Craig was very definitely a body conscious type who looked after his physique, of which he could be justifiably proud; he had spent a lot of time and effort getting himself into his present the shape. The body I was looking at – with admiration and with more than a tinge of lust, I might add – did not just happen by accident, but was the result of a lot of dedication and hard work; there was not an ounce of fat anywhere on his body and he had splendid, beautifully defined  muscles; as he turned around and I got my first view of his arse, well my heart just jumped for joy; he had the sort of bubble butt which was a dream just crying out to be fucked.  All in all I had clearly tumbled by accident on a sexually very desirable young man; one with whom I would quite happily have had sex with free, gratis and for nothing had we met under different circumstances; he was just so alluringly attractive.  I wondered how I should feel in view of the fact that I was here to please him and not to enjoy myself, but what the fuck, things were what they were and I really could hardly wait to get down to business with this superb hunk.

I suddenly realised that Craig was sporting a rock-hard cock, which had sprung to attention as soon as he had discarded the skimpy underpants he had been wearing and moreover, rather surprisingly, he had had all his pubic hair removed so that his man-meat was all perfectly displayed: a nice pair of balls surmounted by a very acceptable cock. But what was evident was the fact that the uncontrollable piece of meat he was pointing at me was telling him, whether he liked it or not, that it wanted some action; in a word although Craig was expecting me to fuck him, he himself appeared just as ready ready to fuck me; at least that is the message that his cock was delivering as we stood there looking at each other. I started to ask myself whether this guy was really the happily married type he purported to be enjoying the odd bout of anal stimulation, or was he, in fact, a closet gay himself, for all indications were that I was probably right.

It was an intriguing thought; was Craig a bisexual guy who liked having sex with both men and women? But I had been engaged to work my magic on his butt and we had never discussed whether he would like a return bout; and I recalled exactly what he had said when we spoke on the phone:  “So I am what I suppose is known as a bottom and I do not want to play the role of top with you.”  But frankly, just looking at him and his present the aroused state, I began to wonder about Craig; I found him such an attractive sexual prospect that I really hoped that things would go way beyond what we had agreed on the phone. But first things first; I was here as a professional escort and I intended to do what I had agreed to do: to fuck his arse, which was going to be a real pleasure for me.

But we could not simply go on standing there looking at each other; the moment for action had arrived. So I said to Craig addressing him now by his first name as we were then in such an intimate situation to do otherwise would be ludicrous: “Craig I practise safe sex and I always us a condom and in the interest of tidiness I would suggest you too use one as it will avoid the mess which sexual intercourse between men inevitably brings in its wake.”  I opened a packet of Fukits rolled one onto my own cock, handed him the other rubber, which, with what I perceived was an expert hand, he rolled onto his own erect member, squeezing the teat to avoid trapping any air.  “Craig what is your pleasure; how would you like me to take you? It’s your party, Craig and your call; just say what and I’ll be happy to oblige.”  Craig looked at me and said not a word but just went over to the table and bent across it spreading his legs to give me access to his anus in what is usually known as the doggy position.  I tore open one of the sachets of Fukit lubricant and applied a generous dose to Craig’s hole and surrounding area. I forced a little lubricant inside him with my finger as I wanted this first fuck to be really comfortable for him. Then I liberally anointed my own rubber clad cock with the contents the second sachet. And so the moment had arrived when I would use my cock for the first time as a declared, professional male-escort. Craig Kolanek was to be my first true client.

“Jeremy, I’ve had a lot of experience with what you are about to do for me, but I have to tell you that never have I know any a guy take so much care in preparing me for fucking.  Listen, what I want is a really hard session; so please don’t hold back; just give me your very best shot and hit me as hard as you can with all that you have got as that is what I want right now.”

“Craig, I just want to tell you before I start, that I intend to try to bring you to a simultaneous climax with that of my own. I know that usually when one guy fucks another, the whole session usually ends by both guys jerking themselves off to reach orgasm. But that is not what I do as I believe that both partners to the act should climax together; and so I aim to climax and reach orgasm inside of you, exactly as a man does with a woman; but at the same time I aim to bring you to your own climax. You see, even though I am performing the sex act with you as a professional operator, a Male Escort, and not as a regular lover, I still feel that such an intimate act should give both participants the same satisfaction; and so I shall just go on fucking you and holding myself back until I see that you are ready to climax yourself; then with one final thrust I will project both of us into that state of nirvana where we both reach orgasm together.”

What Craig thought of my little speech I have no idea, but I immediately thrust my cock-head against his anus and prepared to enter him, which I did with no difficulty.  As I smoothly gave him the full length of my penis, Craig whispered: “God Jeremy you are just so hard and so long, I have never felt anyone remotely like you before.”  Then after a brief pause I began the serious work of bringing Craig to his climax; I am blessed with a very long, well proportioned cock which fills out any partner I am fucking; and I  made each and every stoke powerful and of maximum length, withdrawing almost but not quite completely at each stroke before thrusting myself yet again into him.  I have a relatively slow technique when I fuck someone and I applied measured but powerful strokes, to Craig’s arse, making every pass count; but then, as my own passion builds up, as it inevitably does when I fuck a guy, my strokes become ever quicker and more powerful; but I never allow myself to make that frantic dash towards the finishing post as many guys do and frequently fail in the attempt, leaving both parties to jerk themselves off to achieve that much wished for orgasm without which no act can be considered complete.

By this time Craig was panting loudly and I could see that he was on the verge of his own climax; so I withdrew myself totally, waited a full two seconds, before giving him my full, rock-hard length with maximum force one final time.  As I had planned, we both climaxed into intense orgasms together, as my balls bottomed themselves against Craig’s arse. We were both rocked with the uncontrollable spasms which accompany the ejaculation of a man’s sperm and I can tell you that on this occasion we both produced huge emissions. With my cock still hard and deep inside of him I fell on Craig’s back and there we  remained stuck together for several minutes by our collective sweat whilst we regained our breath and cooled off somewhat.

I finally withdrew myself from Craig and we both stood up and looked at one another. “Jeremy, you really are something else; I have never enjoyed having my ass fucked so much as I did just now;  you really do have a technique and style all of your own, not to mention being superbly equipped to carry it out.”  Praise indeed from my client, I thought; but what happens now?  “Jeremy I hate to ask you this, but do you think that you might be able to give me a repeat performance, but this time face to face as I really would enjoy being worked over by you a second time; you really are something else, you know.”  Of course I had no option but to say yes; after all this guy was paying me a small fortune to have sex with him and deserved something for his money; not, you understand, that I was reluctant to do as he had requested, for quite honestly, to call a spade a spade, Craig was a really great fuck and I had enjoyed fucking him just as much as he had evidently enjoyed being fucked.  And so this time he lay flat on his back on the day bed; and after due preparation and fresh condoms for both of us, I fucked him for a second time and I again brought him to a simultaneous climax with my own.  I think it is safe to say that both of us enjoyed the experience, which for me was a pleasure even though I was supposedly doing it as a professional service for a client. I still had that nagging feeling at the back of my mind that I ought not to take so much pleasure out of doing my job; but there it was; that is how I felt and there was little I could do about it. 

But then came back that desire I had had from the moment I met Craig, or at least from the moment I saw him stripped for action and saw what a splendid looking young stud my client was, which was to have him fuck me. I suppose it was part of my make-up that no matter with whom I had sex, I always wanted reciprocity; it was not enough for me simply to fuck my partner; I always wanted him to do the same to me; and if it was my partner who initiated the act, then I wanted to go on and fuck him back; it seemed to me that the sex act between males should always consist of fucking and being fucked. But this was not part of the deal I had made with Craig, nor had it happened with Hal and Dave, both of whom had simply wanted me to beat them and then go on and fuck their arses. And then there was Miguel, whose view was that a Male Escort’s basic function was to provide anal stimulation to his client but not to expect anything sexual in return.  After all, argued Miguel, the escort was being paid to fuck his client and not to be fucked by him.

Imagine then my joy, when Craig said: “Jeremy, I know that it was not part of our agreement, but I wonder if you would allow me to fuck you.  You know I normally only want a little anal stim; but frankly Jeremy, I have enjoyed being with you so much that I really would like a return match if you agreed.”  If I agreed!  I was over the moon at his suggestion to which of course I said yes, adding that it would be as much of a pleasure for me as I hoped it would be for him. But as we prepared ourselves to reverse our roles, I did wonder yet again if Craig was bisexual and enjoyed gay sex as much as he did his sex life with his wife; anyway, mine not to reason why, but gratefully to accept an act which I had been hoping against hope might take place: truly the icing on the cake for me.

Well an hour later, Craig had served me twice, exactly as I had previously served him and I have to say that he exceeded my wildest expectations as he was himself a very, very proficient cocks-man. I don’t know if my performance had inspired him, but he reamed out my hole with a degree of precision and power worthy of any regular practitioner of the not-so-gentle art of anal intercourse; and as I had done for him, he brought both of us to two immense climaxes at the same time: really an outstanding performance by any standards. But I did again wonder about Craig’s true sexuality, as he performed the anal sex act so well as if it was one of his regular activities. But at the end of the day what did it matter?  He accepted me as a professional male-escort and treated me as such; he paid my fees without a murmur and if he had had a sort of add-on, who was I to complain when it was exactly what I had been hoping might happen.

So of my three clients to date, Craig had been easily the most satisfactory in that he had satisfied my unspoken desire, which had not been the case with either Hal or Dave. But I was just beginning my first professional activity ever, as until now I had never had a job; I had never had to work for a living and I still had no need to do so; but my appetite had been whetted and I had discovered that I enjoyed doing what I was now doing; in fact, I had become, by accident, a professional sex-worker, so I would have to see how things developed. Was Craig the exception that would prove the rule that Hal and Dave had shown me and Miguel had said was the norm; or were there others out there, potential clients for my services, who would also wish to do as Craig had done for me?

Craig was full of enthusiasm, for our evening together and praised my performance to the heavens. “Listen Jeremy, you really are a unique guy and what I would like to do is to schedule (business speak if ever there was) a fortnightly meeting with you – same terms of course – so that we can have a regular repeat of what we have just done; frankly Jeremy, you are just too good to let go. Now, satisfy my curiosity and tell me what you have in that long, leather, tubular case you have brought with you. Oh and before I forget, do you have a card you can leave with me as I have a number of friends who might be in need of your services.”

Before replying to his question about my cane case, I handed him several of my freshly minted business cards.  “Craig, you will see from my card that I offer two services: simulation and discipline.  The stimulation part is what you are now familiar with, but I also have clients (well I had had two, Hal and Dave; so I was only stretching the truth a tiny bit; but I do have a problem in that I cannot lie to anyone.) who enjoys what is commonly called consensual corporal punishment: CCP for short. These are guys, who for some reason or another actually enjoy having their arse thrashed, after which they may or may not ask me to complement their beating by a dose of anal stimulation along the same lines as you have enjoyed this evening. So to answer your question about the tubular carrying case, it contains a selection of rattan canes which I use on my clients’ naked arses.  In my satchel I also have thick leather strap, as some clients prefer that.” And then in a flight of imaginative fantasy, I added: “But I am also planning to open what I think of as a therapy centre, a place where I can receive clients in utter privacy and where I intend to have a full complement of instruments of corporal punishment available, including the time-honoured, traditional American paddle.  You see, Craig, clients’ tastes vary so much and I feel I should be able to offer a full-line service.”

“You mean that some that some guys actually pay you to thrash their asses.” said Craig with incredulity in his voice, “My god, I’ve seen quite a few different Male Escorts  in my time, but never one who did anything like that until now.  And you mean that you actually beat these guys’ naked backsides with either a cane or a strap; and they just let you do that. Have you any idea yourself of just how painful a cane landing on your naked butt must be?   I find it hard to imagine that anyone voluntarily offers his backside up to beaten; and for pleasure yet!”

I smiled as I listened to Craig and said: “Craig, let me just tell you that I was sent by my late father, who was Englishman by the way, to a public school in England, where the cane was in regular daily use.  I can tell you that I am fully aware of just now painful a naked arse beating with a cane is, as I myself experience such more times than I can now remember.  So yes, I am fully aware of the pain I inflict on my clients; but it’s all in a day’s work; it’s purely a question of demand; they want it so I provide it; it’s as simple as as that.  But I can tell you that given my own past experience of being on the receiving and of the cane and on one horribly unforgettable occasion, that old-English favourite, the birch, it is not a pastime in which I personally would ever voluntarily indulge.”

“Nor me neither; so Amen to that.”

CHAPTER 14

That is how my first meeting with Craig, whom I consider as my first true client, ended; and as he had suggested, we did fix a regular two-week appointment for a dose of anal stimulation.  But more importantly, Craig passed on my card and telephone to a number of his friends, all of whom seemed to enjoy having their asses fucked. I was really quite surprised just how many top executives, all supposedly happily married, from well-known, leading companies seemed to feel the need to indulge in homosexual practices; but perhaps as a newcomer the business of selling sex I was being very naïve. Either way by word of mouth my business increased rapidly and basically due to the high level executive types who passed my name around, I found that I was fast developing what I suppose could be considered a quality clientele.  

What quickly became quite clear was what I had considered to be the off-putting high level of my fees, deterred no one from using my services; along with my name and telephone number, my charges appeared to have made the rounds and no one ever questioned them. But as I knew of no one other than myself who offered the same sort of sexual services, I had no means of knowing what I suppose I have to call my competitors were charging.  Although my first true client, Craig, had not wanted my disciplinary services, I was surprised that more than half of my new clients had contacted me precisely because of that; most of them wanted to be punished in some sort of way and then go on to anal sex.  But as Miguel had predicted, relatively few of them wanted to exercise their cocks on me, and so I just accepted the fact that that was the way the Male Escort business functioned.  I think one of the secrets of my success in attracting top quality clients was the fact that I was well-spoken and my clients felt at ease in dealing with someone who had obviously had a good education.

I quickly saw that the demand for CCP was not only considerable but very demanding in terms of what form of punishment the client wanted; some wanted the strap, others the cane, others the paddle;  you name the “weapon” and someone wanted it. And so as my business blossomed, I decided that I had to put into action my plan to create the therapy centre which I had, in a flight of fantasy, originally mentioned to Craig as it was impossible for me to carry around the assortment of implements of corporal punishment to satisfy all needs; so I thought it better that I have my own place, fully equipped with the entire battery of instruments of punishment known to man (and oh boy, are there a lot ) as well as suitable furniture on which I could perform the desired beatings and then go on and satisfy the client’s sexual demands. So, cash being being no problem, I looked around and found a top floor apartment, in the up-market neighbourhoods not far from the Howard Hotel; the place had two en-suite bedrooms, one of which I furnished as the CCP room so that those clients who just want my sexual services were not forced to look at a selection of – for them at least – unpleasant gear. There was a large non-overlooked roof terrace were I installed some outdoor furniture and a shower so that during the warm weather we could conduct tour business unobserved al fresco.

And so my business prospered, so well, in fact, that by the end of my first year aged only twenty-two, I had established a faithful repeat clientele and had to refuse new-comers. None of my clients knew my real name or where I lived.  I separated my business activities totally from my private life and never discussed my affairs with any of my friends with whom I had gay sex on a very regular basis. I learned very quickly not to allow myself to become emotionally involved with any of my clients; business was business and remained just that.  But I have to say that although I did not need the cash I charged for my services, it did give me a great deal of personal satisfaction to see that men were willing to pay for the services I rendered them.  And I did not allow myself to slip into a state of complacency; I saw that one of my attractions, apart from my very generous sexual endowment, was that I had a great body on which clients – and friends too, for that matter – feasted their eyes. So I worked out on a regular basis very vigorously, together with my friend Miguel at the gym where we had first met. 

Life quickly settled down into a routine and although I had no problems in satisfying my own need for regular sex, I began to feel dissatisfied with my lot as that one special person was lacking from my life. I suppose Miguel was my closest friend and we had a lot of great sex together; but as I mentioned earlier I saw that both of us were motivated by sheer lust; in a word, we were sex partners but not lovers. This fact was never put into so words by either of us, but neither of us ever suggested to the other that we move in together; and so I led a full but rather lonely, soulless sex life, as I guess did Miguel. 

It must have been about a year after I had started my business that I by chance bumped into Kenneth Best, the printer who had produced my visiting cards and whom I had not seen since that night when he took me to that hardest of hard-core gay clubs. And of all place to meet him, it was in the bar at the Howard Hotel, which I still occasionally frequented from time as I still enjoyed pulling some unknown guy for a one night stand. The fact of the matter was that in spite of my regular sex life, both professional and recreational, I stilled enjoyed the challenge of the unknown. When I say I bumped into Ken, it was he who saw me standing there at the bar, jawing to my old friend Pete, the bartender, about a potential pull for that evening and he came up to me: “Well Hi stranger; long time – no see; how are things with you these days?  I still remember that first meeting you and I had the day I printed your visiting cards and that steamy club we went onto  later on; so how’s your business doing and what brings you here tonight?”

“Well Hi Ken; what a surprise; I just dropped in here as I often do for a quick drink and a jaw with my old friend Pete, the barman.”  I did not bother to tell him the real reason for my visit. “So how about you; what brings you to this neck of the woods?”

“In fact, I have just been delivering the proofs of the hotel restaurant’s latest wine list the head wine-steward for his approval before I run it off.  You see, for quite a few years now, I’ve been printing their wine list, which they update every month, and as I was here I just dropped into the bar for a drink.  But listen Jeremy, I live not far from here so why don’t you come round to my place for a quiet drink and we can catch up on what has happened in the meantime?”

You will recall that I had much enjoyed my one encounter with Ken the day he had printed my visiting cards, which I had paid for in kind, but that after that really hard-core gay club we had gone onto after supper, I had decided that even though I had found Ken extremely attractive and we had had great sex together, that he was probably a bit too way-out for my taste; and so I had not pursued what was a potentially interesting friendship. But now, a year or so later, I saw that I still found Ken just as attractive as that first day when I had fucked him as a payment for my visiting cards.  But as he and I had got on very well together and as he had my business phone number, I wondered why he had not attempted to continue our nascent potential friendship by ringing me.  However, standing there at the Howard bar, looking at Ken, I realised what a good-looking stud he was; and to be honest, just at the sight of him again, after a year, I could feel my cock stirring in my pants.  And so, with his invitation offered, I accepted it and off we went to his place.  He lived in an apartment house not far from the Howard Hotel where he rented a small apartment with one bedroom. Of course, I don’t have to spell out what happened that evening other than to say that we both fucked each other silly as that first-sight, mutual attraction was still there.  Ken asked me why I had never contact him again and I asked him he same question, but in reverse, before I came clean to him.

“Ken, I’m going to level with you so please don’t be offended by what I say. We had a great time together that first evening and you really do know which end is up when it comes to sex, as tonight has again shown; but quite honestly, much though I liked you at first sight and I enjoyed more than I can tell you what we did together that first time, I felt that you and I would not get along in the longer term as you were much deeper into really hard-core raw sex than I could ever be. Quite honestly, Ken, I enjoyed that club experience just once; but it could never be part of my regular scene; and so I felt it was better to let things rest at that; so I allowed what was a potential friendship to pass by. But you could have phoned me if you wanted as you had my number on the cards you printed for me.  But Ken, don’t get me wrong as I do really enjoy having sex with you; you really are the tops.” I had no idea how Ken would react to what I had just told him.

“Well Jeremy, thanks for coming clean to me. Look I fully take your point; in fact, I decided after that night at the club that it was just too way-out even for me; so believe me or believe me not, that was the last time I ever went there.  You are quite right; it is a place for guys who are really very deeply into the hardest-core gay sex. You knew immediately that it was not for you and I too also realised shortly afterwards that it was not for me either.”

In a way, I sort of heaved an internal sigh of relief about Ken’s epiphany as I found the guy just so physically attractive I could barely keep my hand off him. So after that evening for quite a few months, we met in a restaurant after he had shut up shop for the day and then we went back to his place for an evening of sex. For my sins, and I really felt awful about it; Ken displaced Miguel as my closest sex partner, although I still had sex regularly with Miguel; but neither Ken nor I could get enough of each other.  Ken knew nothing at all about me other than what was on my visiting card: my fictitious name Jeremy and my phone number but nothing more; he had no idea – none at all – that I was stinking rich with no need to work for a living and that I did my Male Escort job because I enjoyed it and not for the money in brought in; though that, by the way, had become quite considerable.  But as time went on, I knew that I had fallen in love with Kenneth Best; but in the event it was he who declared his feeling for me first.  We always met in cheap restaurant somewhere before going to his place to indulge our passion for each other in an orgy of sexual gratification. And as time went by, I more and more frequently stayed on and slept with him in his bed, exhausted by our sexual athletics. On one of those occasions, lying next to him in bed after an evening of very satisfying copulation, Ken turned to me in bed, kissed me and said: “You do know that I love you Jeremy, don’t you? Jeremy I have never ever before fallen in love with any guy but I have fallen in love with you, I just adore you; you do know that; don’t you?  Actually I think you do. But the question is how you feel about me. I know I’m not the only one you see; but how do you feel about me?”

Well of course, I was over the moon to find that this superbly handsome, young stud was head over heels in love with me and I could but admit to him that the feeling was mutual. And that is how I found the love of my life: the man whom I had discarded and whom I had, quite by chance found again.  As we lay there in bed, exhausted as we were by our earlier efforts, we nevertheless each found enough strength to consummate our mutual declaration of love in what proved to be a wonderfully soft and gentle hour of truly loving sex. Yes, of course we fucked each other, but in doing so we were actually making true love for the first time. It was an incredible moment for me – and I suppose also for Ken – as that feeling of utter contentment diffused through me: I was no longer alone in life. Before we finally fell asleep, Ken said to me: “Jeremy now that we know where we stand, I want you to move in here permanently so that we can live together as an item.”

Just reflect on the situation for a moment; Ken knew nothing about me beyond my name, Jeremy, my phone number and what I did for a living.  He had no idea even of what my surname was or where I lived or that his partner in life was a multi-millionaire; and yet this young man, with practically nothing other than his small printing business was inviting me to come and share his life in a small apartment he rented.  Next morning as Ken prepared to leave for work and open up his shop for the day, I said to him: “Ken, in the light of our changed circumstances since last night, there are certain things you need to know about me.  So this morning, please take time off, as I have to talk turkey with you and straighten you out about me.  Heavens above man, you don’t even know my surname; and you are inviting a Male Escort, a man who fucks other men for money, to come and live with you.”

“Well what does it matter that you earn your living by fucking other men? It’s just a job like any other; and anyway, I knew that from the start. Remember Jeremy that it was I who printed your business cards and indeed it was the fact that you were a Male Escort that got us started together in the first place. And as for your name; well it’s just a name; who cares; I certainly don’t; I’m not in love with a name and I am not in love with a Male Escort neither of which have I asked to come and share my life with me. It’s you Jeremy, my lover and dearest friend, with whom I want to spend my life.”

Having listened to this outpouring I think that Ken feared I was going to pull out of what we had agreed in bed last night.  “Ken, listen to me, there are things you just have to know about me now that we are going to live together; things are not quite what they seem and you really have to know the truth about me; so please just calm down and let’s talk. I am not going to move in with you here, as I have a much better idea, which I will show you if you will let me.  So come on Ken, let’s go and for a start, I’ll show you where I actually live.”  In fact my apartment was not all that far from where Ken lived and when we arrived there, the porter on the desk said: “Good morning Mr. Stevens; how are you today?”

I turned to Ken and said: “Well there you are Ken, at least now you know my name: it’s Stevens; in fact it is Andrew David Stevens; Jeremy is just my professional name: the one by which you and my clients know me.” We took the elevator to the top floor where my apartment was located and I opened the door and ushered Ken inside. He was gob-smacked by the size and luxurious furnishings of the place.

“Jeremy, or should I now call you Andrew; you mean this is the place where you really live. Gee man this is something else; it’s quite magnificent.  And you mean that you can afford this on your earnings as a Male Escort; if so, I’m clearly in the wrong business completely.”

“No Ken, I cannot afford this on my earnings as a sex worker, for let’s face it, that is what I really am; and that’s why I wanted you to see this place and let me explain my position as you know nothing much about me.  You see, Ken, by chance you have fallen for a very rich man, who has also fallen for you. Look I inherited two large fortunes: one from my grandparents in England when they died a few years ago and then another form my father when he died unexpectedly aged only forty-eight. So you see, I don’t actually need to work to keep the wolf from the door; not now or ever; I just do the Male Escort thing as I enjoy it; nothing more nothing less.  So you see Ken, it is I who want you to come and shack up with me here; and Ken, if you don’t like the idea of my continuing with the escorting business, selling sex to other men for an exorbitant fee, then I can stop as of right now; I don’t need the money  to live on.  But come on and I’ll show you around and you’ll see what a great place this is. And in addition the place comes with a huge, totally private, roof terrace where I have installed a shower so that in warm weather we can fuck under the stars. Ken I think you’ll love it here.”

“But you can’t expect me to move in with you into a place like this; I could never afford to pay my share of the rent and I don’t want to think that I am being kept.”

“Ken, stop talking a load of hogwash. Last night when you knew nothing of my circumstances other than that I was a Male Escort, you wanted me to move in with you and you never even gave the first thought as to what my contribution to your place would be; your sole motivation was that you and I should live and sleep together, and fuck each other; you never even gave a thought to what I could contribute other than my presence as a permanent fixture in your life; so where’s the difference? We are both totally in love with each other and want to live together and the fact that I have got more cash than you is incidental. It does mean that we can live a more comfortable life together; but then what is cash for but to spend? And I can tell you I have enough loot for both of us. But there is no reason to change our life styles; you can go on with your printing business and pay part of the rent if it makes you feel better and we can split the other running costs too if that is what you want; and if you do not object, I can go on with my escorting, which I frankly enjoy and which, believe me, is very lucrative. So apart from a change of address for you, nothing need change.”

I finally talked Ken around and convinced him that by moving in with me he would not be sponging on me as he had known nothing of my wealth when we first met. Finally I took Ken by the hand and led him into one of the bedrooms, where I said to him: “So as we are now agreed that you will give up your present apartment and move in here, let’s seal our agreement in a way which will please us both.  Get stripped Ken, lie on your back on the bed I’ll give you the best fuck of your life to close the deal and to welcome you into my life.” And of course, once we got started, there was no stopping us and we spent the whole morning in my bed, fucking each other like rabbits.  We were both completely and utterly in love with each other and I had never been happier my life.

Neither Ken nor I had been monogamous before our mutual declaration of love for each other as we both had had other partners before we actually met and such relationships had continued. But now that we had decided to live together, we promised each other that we would henceforth remain strictly faithful to the other; it was almost as if we had taken the marriage vow:  forsaking all others keep you only unto him.  But what we also agreed was that my Male Escort business, which inevitably involved sex with third party men, would not be included in this declaration of fidelity which was basically intended to protect our status as an item. As you might well imagine, in love with each other as we were, it would be intolerable for either of us to find that his life’s partner was having it off on the side with other guys. In fact, there was no difference in our mutual attitudes to having sex with others.

Believe me, gay relationships are just as subject to jealousy provoked by one partner philandering as are normal heterosexual marriages. So we also agreed that we would not cut off sexual relationships with other men, provided that we entered into them together as an item; neither of us wanted to live totally isolated from other friends.  Inevitably practically all our friends were gay and if we got together then sex was more or less inevitable; but we both agreed that if we found ourselves at a gay gathering where sex took place, then we could participate in the general exchange of partners which usually occur on such occasions. At the end of the day we both accepted that we were a pair of swingers and that although we were an item and devoted to each other, we did not wish totally to cut ourselves off from the gay sex scene of which we were both part.

For me, the hardest thing I had to do was to tell Miguel, who was my oldest and dearest friend, and sex partner and a sort of father confessor figure to me, that our hitherto intimacy would have to cease. He and I had enjoyed a long and mutually satisfying sexual relationship and I trembled inwardly at the thought of what I had to tell him. I think we had both known for a long time the unspoken fact that our relationship was founded basically on lust; the desire of the one for the other, but not based on any true love.  We both knew that good friends though we were, enjoying each other’s body and sexual abilities, we were never going to be lifetime partners; we were never going to be an item in the way Ken and I had become. Miguel, who, in spite of his youth, was a wise old owl, had realised that our relationship would never be more than it had been so far: two guys who liked each other and liked to have sex together; and it was this mutual understanding of our relationship that softened the blow when I told Miguel that Ken and I were an item.

And let me just say that Miguel was a true gentleman and accepted the fact gracefully and congratulated me that I had been lucky enough to find the love of my life.  “I always knew that you and I would have to part one day.  I only hope that I will have the same luck you have had and find the right guy for myself.  But how will I know?”

“Oh Miguel, when the right guy for you turns up you’ll know all right; it will hit you like a ton of bricks.  Now come on let’s just get together for one last time before I withdraw from the scene.” And as you might have expected, we spent the next two hours or so in multiple acts of intense anal copulation.  It was with greatest regret that I left Miguel’s place for that last time.

Later that week, Ken left his apartment and moved in with me; it was an easy move as he had rented the place where he lived fully furnished and so he only had his clothes and personal effects to move, which we did in a taxi as neither of us had a car.  Thus began our life together and I think I can say that we were extremely happy.  Of course for the first few weeks, we fucked ourselves silly as I suspect most newly-weds do; but as we became more comfortable living and sleeping together, our sexual desires calmed themselves somewhat and the deep appreciation of the joy of sharing one’s existence with someone one loved came more and more to the fore.

And to conclude his account of my early life, Ken suggested that we hold a reception for a few close friends which seemed like a good idea.  So I hired a caterer to put on a buffet, bought loads of champagne and we invited our closest friends from both sides, all of whom had been sex partners. Given that the party was being thrown by a pair of swingers who had just got together and that the entire company was gay, it was inevitable that he whole occasion would turn into one great fuck-fest. And that is exactly the the right word to describe what happened as we all quickly stripped off and split into groups to enjoyed the cock-related gymnastics which characterise such occasions, when uninhibited gays get together. We had an absolute ball and Miguel, who was, of course there had sex with both Ken and me; so I felt he knew that I had not completely abandoned him. So our life as a devoted pair got off to a flying start. Everyone got the message that we were still very much in the gay circuit, but as a couple. As far as Ken and I were concerned, our lives as individual gay swingers were over.

THE END

by Jason Land

Email: [email protected]

Copyright 2024