Onwards and Upwards for Alex

Readers are recommended first to read my earlier story entitled “Alex’s Profession” before embarking on the present tale, in which Alex explains, how after having been more or less rail-roaded into becoming a male escort by his friends, led by Dr. Alan Greenberg, suddenly found his feet in the world of gay sex and succeeded beyond his wildest dreams of turning his favourite pastime into a lucrative career for himself. For the sake of completeness,  I have however written an introductive recapitulation of the events leading up to Alex’s, or rather Stan’s, as he was then known, decision to enter into the gay sex-trade as a male escort.

Introduction 

Many readers will already know me as Alex, a male escort, a name which I use for business purposes as being more attractive and certainly easier to say and remember than my real name, which is Stanley Przewalsky.  I have already told you of my earlier life in Chicago and how I was more or less propelled by Dr. Alan Greenberg, a surgeon, into my present profession, where, I have had what can but be described as meteoric career in the Chicago area. Dr. Greenberg did some surgical cosmetic work on my cock and balls and liberated me from a hang-up with my physical appearance which I had had since the age of fourteen when I first became aware of the fact that I was sexually interested only in men.

When I first contacted Alan, as I have come to know him as a friend, it was to ask him if he could correct what I saw as a deformity of my penis, which was a severe inhibiting factor in the development of my sex life. At the time I was already living, more or less as an item, with a guy, Carlo Brenner, with whom I had hitched up at school.  I knew as soon as I first set my eyes on Carlo one evening in the school gym that I had found my life’s soul-mate and luckily as it turned out, he was as smitten by me as I was by him; and so we came together as a pair of equals in what has turned out to be that mythical union, the match made in heaven.

At the time Carlo and I got together, I was already seventeen and had never had consensual sex with anyone as I truly was the shrinking violet: a sort of gay guy in waiting. Note I said consensual sex, as I had previously been raped by the school principal, which had made me somewhat cautious of sex in general.  Also I was embarrassed by what I saw as the deformity of my otherwise exceptionally large penis. So when I left school at the age of eighteen and moved in with Carlo who was a year older than me, he was, and remained, for over a year, the only guy with whom I ever had sex. Carlo was much more experienced than I; but even though we were living and sleeping together, he still indulged himself regularly in casual sex with guys he met in various clubs and bars which he frequented.

Although I knew none of the men with whom he had sex, nor, as far as I could gather, neither did he; his dilettante, casual sex-life consisted of a series of one-night-stands with men whom he never saw again. I was nevertheless insanely jealous of these guys, none of whom I ever met.  My biggest fear was that Carlo, cock-loose and fancy-free as he was, might one day find some guy, whom he preferred to me and leave me high and dry.  In case I have not made myself totally clear, let me just say that even then, at the very young age of eighteen, never having played the field at all, I was deeply in love with Carlo and would have been devastated if he had left me for another guy. And it was this persistent thought of being dumped by the man, whom I saw as the be-all and end-all of my life that propelled me to seek surgery to correct what I saw as the deformity of my penis.

To be fair to Carlo, he had encouraged me to go along with him on his foraging for casual sex, which he assured me, for him had exactly the same significance as any other social activity such as sport, or the cinema or dinner with friends; or any other of a myriad pastimes in which people indulge for pleasure.  It had nothing at all to do with our deeply serious, committed sexual relationship. But given what I saw as the deformity of my penis, that bane of my life, my excessively large and pendulous foreskin, in a land where most male s had been circumcised at birth, I never dared accept his invitation to go with him on any of his forays for casual sex. And so I remained for quite some time, with Carlo, my lover, being the only man with whom I had ever had sex.

I first met Alan in a professional doctor- patient relationship. Not only did he circumcise my cock but he surgically adjusted my scrotum at the same time, so that my balls were held closer to my body, allowing  my eight inch  penis, (I exaggerate not!) to fall in a sexually very attractive curve from my pelvis over my balls.  What this guy did for me was to add visual value my cock, which by its sheer size, even in its uncut state, had made most of my classmates green with envy. Alan, as I was soon to learn, was himself an active gay and our original doctor-patient, ethical relationship rapidly turned into a sexual one.

To my utter astonishment, Alan, seduced by my sexual attractiveness as a result essentially of his of his own prowess as a cosmetic surgeon, asked me to fuck him, for which service he waived his professional fees. So Alan  became only the second man with whom I had had sex in my then life to date  But our relationship went further than just anal sex, as Alan was hooked on corporal punishment and on our very first intimate occasion together, produced a cane with which he persuaded me to beat this arse prior to my fucking him. This surprise encounter proved to be one, which was to change my life forever.

From the very first time I fucked Carlo with my deformed – as I saw it – cock, Carlo had waxed lyrical about my copulative abilities; so much so that he sounded like a broken record.  But at the time, having no sexual experience other than with him, I did not see immediately what distinguished me from his other partners. However, after I had dipped my oar for the first time into unknown waters, this time into Alan Greenberg’s anus, I was again praised to high heaven for my sexual ability, which he qualified as being: “The benchmark against which all others will henceforth be measured; at least, by me.” I was not sure what I had done to deserve such fulsome praise. After all, I had fucked the guy just once.  But he sounded so sure of himself that his observation, coupled with the praise which Carlo continually heaped on me, set me thinking. Did I, as the only two guys with whom I had ever had sex evidently thought, have something special, which other guys did not have? Did my performance justify putting me on a pedestal as a beacon of sexual perfection, which is what both my sex partners to date had done? I have to say that it made me think; even more so when I considered  that Alan had lavished his praise on me after just one experience with my cock and that both he and Carlo were, to say the  very least, experienced and practising members of the gay community.

But what shattered me more than the praise for my efforts, was when Alan suggested that the endowment I had between my legs was more or less worth its weight in gold. Moreover, given that I knew how to use it, a gift given to few men in the way it had clearly been given to me – like a Greek God, was the way he put it – I ought to think about making a career to exploit my natural assets. In short, he suggested that I consider becoming a male escort. At the time he made the suggestion, I was so naïve that I had no idea what a male escort was or did. Writing this as a successful male escort some years after this eye-opening remark made by Alan, I was horrified at the time that he should suggest that I consider prostituting myself; fucking other men for money.

But as Carlo so appositely said later that evening as he was sampling my newly modified cock whilst listening to me relate my experiences with Alan: “Stan, you have already sold our body for money to your surgeon friend. Just think about it; although no money actually changed hands, he has done the work on your cock, which has made a new man out of you, liberating you from your previous hang-up. So in exchange for your having sex with him he has forgone his $750 fee for his surgical services, which is basically what you have charged him for your services.”

“But today was quite different; Carlo. I would frankly have fucked Alan for free as I was just so delighted with what he had done for me.”

“Well, as I see it, Stan there is no difference at all. You have accepted payment for your sexual services. If you feel guilty then just go and give him back to him the $750 and then your conscience will be clear. Think hard on what both Alan and I have told you. You, Stan, have an exceptional talent when it comes to gay sex; I agree with Alan that you should seriously think about using that talent professionally. Stan, your future is staring you in the face; or better put, hanging between your legs; so don’t look a gift horse in the mouth. But enough of all that for now! Don’t you realise that whilst you have been swanning-off getting your beauty treatment that you have have completely neglected me; so much so that I am beginning to exhibit withdrawal  symptoms as you have not fucked me for over two weeks. So if you want to salvage our relationship before I commit suicide, I suggest that you here and now fuck the living daylights out of me. God, Stan, I’ve missed you whilst you have been out of action waiting for your cock to heal; and even though you have let me fuck, you it’s not been the same. I have felt only half a man.”

I knew exactly what he meant and of course went ahead and obliged him.

Chapter 1

Alan’s suggestion that I become a male escort had seemed totally outrageous at first sight. Here was I, with my sexual experience limited to only two men: Carlo, with whom I was having regular, two-way sex:  we topped and bottomed for each other: and Alan, whom I had fucked and in return had been fucked by him just once.   I had never been to a gay club or gathering and indulged in casual sex in the way that most gay men appeared to do; the way my partner, Carlo, much to my annoyance, I hasten to add, still did; And now here was Alan, after one brief, physical contact, telling me that he thought I could make a career as a male escort. Frankly, just thinking about it, it seemed too farfetched to me.

And yet, both Carlo, whilst he and I had been still at school, and Alan, after the very first time that I fucked him, had told me that I had something special about me: something which other men apparently did not have.  According to them I was in a class of my own when it came to anal intercourse: the next best thing to sliced bread, to draw a ridiculous analogy! I recalled word for word what Carlo had said in his bedroom after I had finally surrendered my virginity to him and sampled his anus with my cock.  “You, Stan, are just a great cocks-man from the word go: an undiscovered treasure! And I consider myself privileged to have had the honour to be the guy to whose anus you relinquished your virginity.”  It was this immediacy of reaction of both my – my only two – sex partners after my very first efforts with them as a top that started me thinking.  I had always had a large cock, of which, after Alan’s surgical modifications, I was now inordinately proud; after all, it is not every guy, who can field a ten-inch, rock-hard erection with a well-defined knob at the end of a dead-straight shaft. But there had to be more to their joint enthusiasm than the size of my tool, important though that might well be. So what was it that made me special in their eyes?

For the next few weeks, I became accustomed to the sexual freedom that getting rid of that cumbersome piece of foreskin had mentally given me. And, as he had long begged me to do, I started going with Carlo, on his visits to the gay clubs and bars that he frequented in search of casual sex.  I can tell you that what went on in such places was an eye-opener to someone as naïve and inexperienced as I then was to the uninhibited world of gay sex. But to my surprise, I found that I too enjoyed the easy-come, easy-go atmosphere of such places. I very quickly found that like Carlo, it was a lot of fun to have casual sex with a series of guys, whose names I never knew, and whom I would probably never see again. And I also lost all inhibition about stripping off in front of men I did not know. In fact, I soon came to revel in the admiration which my exceptionally large endowment suscited from other men. There is little doubt that a cock of which one can be proud does wonders for any man’s self esteem.

I suppose you could say that I became a typical gay young man, now totally relaxed in his new found freedom: someone who now felt good in himself, enjoyed his life to the full and revelled in the seemingly endless, sexual pleasures, which a large and sinful city like Chicago had to offer. However, let me also add that like a pair of homing pigeons, both Carlo and I were glad that we had each other. Even after a physically exhausting evening out on the town in search of casual sex, we always finished up in bed together in our little apartment. I think that Carlo needed me just as much as I needed him.  We were just made for each other. I saw that Carlo had been right in his assertions; casual sex was just pastime in which he – and now I too – indulged, which in no way influenced what we felt for each other;  we were, in fact, a rock-solid item enjoying the sexual freedom which a big, sinful city like Chicago offers.

It was during this transition from the shrinking violet to a confident and sexually active, gay young-man that I discovered what was patently obvious: the majority my sex partners were in awe of the size of my endowment, which they viewed with admiration tinged with a touch of jealousy. After all, it is not every day that a guy finds himself confronted with a partner he does not know, who is sporting a ten-inch rock-hard erection. And it was this sheer size of my cock, which led me usually, but by no means always, to be the top in any casual partnership.  As I had received from Carlo and Alan after I had first fucked them, I found that I was regularly showered with fulsome praise from my usually anonymous partner, as having given him – in his words – his greatest sexual experience ever. So not surprisingly now that I had got my feet under the table of life as an active gay, I began to ask myself what it was that I personally had, which made most of the guys who bottomed for me, wax lyrical about my sexual capabilities. What did I have that others clearly did not?

I had long been a devotee of gay porn sites on the internet and it was from this purveyor of all knowledge that I finally realised that my approach was unlike that of the majority of practitioners of the oft not-so-gentle art of anal sex. As I learned from my internet research, art was the absolute antitheses of what most guys practised in playing the role of top in gay sexual partnerships. Now most of the sites I looked at were staged for viewers, but my own experience when I bottomed – rarely the case – in one of my nights out on the town on Chicago’s gay scene, confirmed what appeared generally to be the case.

Most guys begin by sucking their partner’s cock, then rimming his arse with their tongue, before proceeding to the act of copulation proper, which, crudely put, consists of one man sticking his cock into another man’s anus and then proceeding by a series of often violent thrusts and withdrawals, to attempt  to bring himself to orgasm. But then, all sex acts, although physically infinitely satisfying, at least for the man whose cock is playing the active role – the top, as he is called – are really visually very crude. In spite of their ubiquity, and judging by the sheer number of sites, success, explicit videos of two or more guys indulging in anal copulation together, do not make great theatre, for me at least. At crunch, given the choice between watching guys fucking each other or watching pain drying, sure, I would choose the former; but believe me, in terms of visual interest, for me, there’s not much in it; I find both pastimes visually utterly boring. Don’t get me wrong on this; I personally enjoy gay sex, both as a top and a bottom; it’s just that I don’t find watching other men fucking each other the way most of them seem to do, a particularly interesting pastime.

But the difference between what I saw most men do as tops and what I myself did, were as different as chalk and cheese. As far as I could see, usually when two studs had anal sex together, the top, after minimal foreplay – cock sucking and anus rimming – thrust  his dick into his partner’s hole and then fucked him hell for leather as if there was no tomorrow. His cock reciprocated like the piston of a steam engine, which he seemed intent on emulating. The bottom, meanwhile, usually worked his own cock manually, whilst he was still in the process of having his hole reamed out. Then the top usually withdrew his dick from his partner and he too began to jerk himself off manually. So the two of them ended what had begun as a copulative exercise by masturbating together to reach the much wished for orgasm, without which sex is a total and utter waste of time.

Looking at these videos on the internet, reinforced by my own experiences as a bottom with a series of unknown, one-time-only, partners, whom I picked up with Carlo on our frequent trawls of the gay-sex hotspots of Chicago, I gradually came to see why Carlo and Alan both waxed lyrical about my capabilities as a top.

The great difference between me and most of the rest – I say most of the rest, as I would not wish to claim that I am unique – is due to two quite separate things. Firstly I have been endowed by nature with a truly massive penis, which when it is erect, as it frequently seems to be, that broken record, Carlo, never tires of comparing to the Washington Monument. And with no false modesty, I have to say that my cock when rock-hard and ready for action is really something awesomely magnificent to behold. Not only do I have the length – ten inches – but I also have the girth – more than six inches – which translates into a diameter of just over two inches. Add to this a magnificent, newly-exposed cock-head, my helmet, with its well-defined rim, the whole lot buttressed by a pair of high-held balls, thanks to Alan’s surgical skill, and you will appreciate that I am blessed with an exceptionally attractive sex cannon.

But an exceptional tool is no guarantee of a good job if the workman using it does not know how to use it properly. As a newcomer with no prior instruction in the art of anal copulation, other than advice from Carlo, that I should always ensure my partner was adequately lubricated before shafting him and thereafter make haste slowly, that is exactly what I did the first time I had anal sex with anyone, which was with Carlo, my future long-term partner to be. But beyond the lubrication and making haste slowly, what I did on that maiden venture into what I found to be the delights of gay sex came to me naturally as if I had been doing it all my life and was to become my unique signature style.

Let’s face it, at first sight there does not seem be anything particularly complicated about anal intercourse. The top thrusts his erection into the anus of his partner and then proceeds, by reciprocal movements of his pelvis, to massage his cock to orgasm inside of his partner’s rectal passage. But it is in this process of how the top fucks the bottom that separates the wheat from the chaff; and I can tell you that in my view, from my own observations and personal experience when I myself have bottomed for other guys, there is an awful lot of chaff around.  And it is precisely when I have shafted my partner and paused to allow him to appreciate the unique pleasure of feeling the full ten-inches of my erect man-meat inside of him that I differentiate myself from the normal frenetic process of fucking, which in most cases usually seems to follow.

Thanks to the exceptional length of my own endowment, I am able to give my partner very long strokes of my cock, which coupled with my large, well-rimmed cockhead, provide him with a unique sensation as I first very slowly begin process of fucking: the thrusting and withdrawing of my shaft in and out of his rectum. At first, I withdraw at least half my length from my partner at every stroke. But as I progress, I gradually build up both length and speed, until finally fully aroused, as I inevitably become, I find myself automatically withdrawing my cock almost fully from my partner at each stroke and thrusting myself back inside him, bottoming my pelvis against his arse with ever increasing force and speed. However, I never allow the inevitable effects of the sex act on me to take over completely and always keep in mind my ultimate goal, which is to bring both of us simultaneously to an orgasmic climax.

And so I judge the state of readiness of my partner for the ultimate pleasure, which few bottoms as far as I can see ever experience without some manual assistance from themselves, of being taken through to orgasm solely by the efforts of their their top partner. It is relatively easy to judge from the moans of pleasure and verbal exhortations from my bottom partner not to top, the moment when he is ready to climax. And it is precisely then that I withdraw myself fully from him, hold my cock clear of his anus for a couple of seconds to allow him a brief pause in anticipation of the final climactic moment, before plunging, with maximum force, my full length back inside him, thereby bringing both of us to that ultimate goal of the simultaneous orgasm. It is hard to describe to anyone who has never had the experience of being fucked through to orgasm by his partner, of the difference both of the intensity of feeling and the much more copious emissions of both partners to the act, than that achieved by simple masturbation alone, which, as all men know, is itself a pleasurable act not be sniffed at.

I have described in some detail exactly how I go about fucking another man, as it is something which came to me quite naturally from the word go. The first time I had sex as a top was with Carlo. But equally when I had sex with Alan, only my second partner ever, I was almost drowned by their same, independent praise for my unique ability, which made Alan suggest immediately that I should think about becoming a male escort. At the time, I have to say that I did not see initially what was so special about what I had done to my only two partners to date as it had come to me completely naturally. However, after Alan took care of my cock problems and I emerged from my essentially monogamous relationship with Carlo and started accompanying him on his frequent visits to gay hang-outs in search of the casual sex, without which he did not appear to be able to live, my eyes have been opened to what usually seems to happen when two guys have sex together. And so I have now realised that I do probably have a talent share by few others. But is this an ability from which I could earn my living?

Chapter 2

I had by now realised that career-wise, in my job at the supermarket, I was on a road leading nowhere. And so, after considerable thought, a good month after my liberation from the inhibiting embarrassment of what I had thought of as my deformity, I was on the point of recontacting  Alan Greenberg, to explore further with him his suggestion that I consider becoming a professional Male escort, only to be pipped at the post by a call from Alan himself, with an invitation to Carlo, whom he had never met, and me to what he referred to as a soirée he was giving at his apartment at Lake Point Tower. He was somewhat vague about the exact reason for this gathering, but reading between the lines and knowing his penchant for both, I guessed that consensual corporal punishment and sex would be high on the agenda. So on behalf of Carlo and myself, I accepted.

Our reception as we arrived at Alan’s sumptuous apartment in Lake Point Tower, was a complete surprise, but instantly confirmed my suspicions that we had been invited to an evening of sex. I rang the   door-bell and door was opened by Alan himself, stark naked and obviously totally at ease with his lack of attire. Carlo, who is very much a man of the world when it comes to matters sexual, had never before met Alan, did a double take at the naked figure before him before we crossed the threshold and entered. I felt that twinge of excitement run through my body as I gazed at Alan, who was a very attractive, sexually well-equipped guy with a body, which like Carlo’s and mine, testified to regular, serious workouts in the gym.

Alan ushered us through his vast apartment into what I had, on my last visit, learned he called his recreation room; recreation, which I felt very sure consisted of only two activities: sex and corporal punishment. Was I surprised to find Jeremy, Alan’s professional nurse, waiting there, attired, like Alan, only in his birthday suit? In fact, I was not. I suppose it seemed par for the course, as I had previously painted Jeremy gay in my own mind and had suspected that the relationship between Alan and him went much further than the professional relationship between a doctor and a nurse.

“Well guys,” began Alan, somewhat uneasily, “I have a small confession to make to you both.   I have have brought you here under slightly false pretences; the soirée of which I spoke consists only the four of us.  You see, Jeremy and I, who as you have probably guessed, are much more than professional colleagues. We are like the two of you, very much an item and have been so for well over a year since we first met. So you will forgive us both, if we have enticed you here under false pretences that you were coming to a larger, gay shindig. Stan, as you must know by now, from the very first moment you came to me professionally I saw you, as a guy exceptionally well equipped and your capabilities were well and truly confirmed to me when you and I had sex in this very room. And Jeremy, my partner, who is a fully qualified surgical nurse and tended to your pre- and post-operative care, was also mightily impressed by your sexual credentials.”

“And so together Jeremy and I thought it might be a good idea if we met Carlo and got to know you a little better and possibly became closer friends. So there, gentlemen, you have it. You have been invited here tonight in the hope that as a group of four, gay young-men we could find some common ground among us; and who knows, possibly become good friends. Somehow, it seemed to me that if the four of us could establish some kind of regular relationship, sharing each others’ capabilities, it would provide us all with that essential variety in life which we all need, without the recourse to frequenting the sleazy gay bars and clubs in search of the element of casual sex, which as gay men, however up-market we consider ourselves, I think we all probably enjoy from time to time. In a word, guys, Although I am sure that our individual relationships, Carlo’s and yours, and Jeremy’s and mine are rock solid, I think as gay young men, we all, from time to time, like to dip our oar into new waters. Variety, as ever, is the spice of life!”

So there, in a nutshell, we had it, Alan and Jeremy wanted to try to establish what amounted to a private sex-club, where we four mutually shared our sexual attributes; but knowing Alan’s penchant for CP, and with punishment canes hanging there in full view, I also imagined that our physical congress might go much further then anal and oral sex; and as events were later to prove, I was not wrong. I looked at Carlo, who, as ever, ready for any sexual adventure, by the expression on his face, not to mention by the state of his cock, that infallible indicator of sexual readiness, indicated that it was already ready to go. So we gracefully acquiesced to Alan’s suggestion; and why not?  We had been invited to a sexual soirée; the prospect of which was already visually exciting: two well-set-up young studs offering themselves to us on a plate. So what was there not to like about it?

So, Carlo and I both stripped off, as clothes were obviously a hindrance for what we were about to do. I think that both Alan and Jeremy were surprised to find that Carlo, although not quite as big as me where in counts, was nevertheless, by any standards, formidably well equipped and physically very attractive – as might I add were we all. Well as ever, the best laid plans of mice and men often go awry, and tonight was no exception. Alan was attempting to put this plan into operation, suggesting we draw lots for first-fuck partners to kick off the evening, when the doorbell rang.  

Laughingly Alan said: “Oh, I had quite forgotten; that will be the pizzas I have ordered to sustain our bodies through what will probably be a physically demanding evening.  I’ll just go and let the delivery boy in.”  Then totally naked as he was, without the slightest sign of embarrassment, he went to answer the door.  The initial reaction of the pizza deliverer, we did not see, but we were regaled with his incredulity, as he brought the pizzas through to the recreation room. His eyes almost popped out of his head as he saw the three of us standing there, in what I hoped he appreciated was our naked glory. Were we all embarrassed? Well actually we were not.  And quite frankly nor was Dave, according to the name plate on his uniform,  the deliverer of the sustenance to keep body and soul together during what promised to be an exhausting evening of heavy sex. As Alan came back into the room with the cash, Dave looked at us and said: “Gee, you guys look as though you are about to have a ball together; I only wish I could join you.”

Now anyone with half an eye could see that college student, Dave, beneath his uniform was a real hunk of nineteen-year old muscle; and moreover, handsome with it. In a word, Dave was a sexily attractive young stud, who would be an adornment to any gathering. So Alan said to him: “If you are that way inclined and feel, as just looking at you, I suspect  you could actively contribute to our gathering, be our guest; you are very welcome to stay; the more the merrier in my book.”

“Gee guys, I really do wish I could; but I am on duty until eleven; so it’s not to be.”  And so with obvious reluctance Dave left.

Alan then opened a magnum of champagne: “I always think a glass of bubbly is the way to get any party off to a flying start. So why don’t we eat the pizzas whilst they still hot and fortify ourselves for the arduous task ahead of us?”  He then added laughingly at the absurdity of the remark he was about to make: “I have always thought that the combination of champagne and pizza was a match made in heaven, as I am sure you will all agree.”  And so we postponed our physical onslaught on each other until we had eaten the pizza.  However, we had barely started on our gastronomic repast, when the doorbell rang yet again.  Alan again went to answer the door and peeping through the Judas window, he saw that it was Dave, who had, for some reason, returned. He opened the door to find out what Dave now wanted, to be greeted by: “If your invitation to join you guys this evening still stands, I have have had second thoughts and would like to accept.”

Alan showed Dave for the second time that evening into his recreation room and said, by way of an explanation: “Dave found my invitation for him to join us this evening just too irresistible and has changed his mind and decided to accept. I see that he is bearing three more pizzas, which I suppose were destined for his next customer, whom I guess he has abandoned to die of starvation in favour of satisfying his own carnal instincts.  Would you say, Dave, that that was a fair summary of the situation or have I read it completely wrongly?”

Dave, slightly embarrassed by the fact that he had been called out on the pizzas, which had obviously been destined for the next customer, attempted to pour oil on troubled waters by saying: “Guys, you really don’t have to worry about the pizzas; I will, pay for them myself; and as far as the other customer is concerned, he has probably already called the pizzeria and a replacement delivery will already be on its way to him.”

With obvious mock severity, but nevertheless in a voice tinged with sarcasm, Alan then said: “Well, Dave, I am sure that it’s a great relief to us all to hear that we are not receiving stolen goods or that the prospective customer, whom you have so cavalierly abandoned in pursuit of your own interests, will not go hungry. But that really does not excuse your lack of loyalty to your employer, whom you have seriously let down by cutting out from your delivery schedule, leaving him in the lurch to make alternative arrangements, whilst you enjoy yourself by indulging in the pleasures of the flesh.  Dave, you really are a very naughty boy. However, now that you are here, you may as well stay and participate in the proceedings. So why don’t you make yourself comfortable, have a glass of bubbly and eat one of your next client’s putative pizzas? After all, Dave, we wouldn’t want you dropping under the work-load you are about to experience for lack of sustenance.”

By now, Dave was feeling slightly uncomfortable and he did not react immediately to Alan’s suggestion. So Jeremy added a word of explanation by saying. “Come on Dave; get your clothes off and relax, now that you are here. We are all dying to see what treasures you are hiding under your delivery uniform.” 

However before Dave had time to react to this advice, the doorbell rang yet again. “Who the hell can that be?” said Alan as he again went and opened the door to find another young man standing there. After scraping himself off the ground where he had figuratively been thrown at the sight of a stark naked Alan, whose cock by this time had become fully erect and was pointing menacingly at him, the unknown newcomer managed to pull himself sufficiently together: “Hi, I’m Zach, Dave’s college room-mate. Dave just rang me and said that I should come and join him here at this address as there was a party planned. I hope I’ve got the right address.”

“Well, Zach, there is a party here tonight; so if Dave invited you to come here, there is no point in your standing gawping at me as if I am an alien from outer space. I take it you have seen a naked man before; so if that has not frightened you off, you had better come in.” As Zach entered the recreation room he did a double take at the sight of so much naked flesh embellished by large erect pieces of man-meat. Dave, meanwhile, who was already embarrassed by Alan’s remarks looked as though he wished the floor would swallow him up as he sought to explain how he had come to invite someone, none of us had ever even heard of, to join us. 

But with the exuberance and cheek of youth, he tried to explain what he had done: “Gee, guys, I guess I let my enthusiasm get the better of me.” Then turning to Alan he said: “But as you had said the more the merrier, I thought it would be OK to ask Zach to come along.  Look, guys, Zach and I are not just college room-mates, but we are sort of already what you would call an item. We’ve been together for over a year now and do everything together; including the sort of stuff that I imagine you guys have in mind for this evening. But if I have pushed my luck too far, and you would rather we go and let you guys do your own thing; just say the word and we’ll be off.”

Speaking myself, but I am certain the others were of the same mind; I certainly did not want either Dave or Zach to leave.  Both young studs were attractively handsome and, from what Dave had just said, clearly sexually very experienced. I for one could barely wait for them both to get their clothes off and show us what they had to offer, which I felt quite sure would be first class. Even fully clothed as they still were, I could see that they were both muscular and I imagined, or probably better said, hoped, that they would also be well endowed between their legs, where it counts the most.  Both Carlo and I had a penchant for guys with generous amounts of man-meat, which is, I suppose, not surprising given our own large endowments. So that is how our exclusive soirée of four became six.  And I can tell you, jumping ahead, that when we finally got down to business, Alan’s words, the more the merrier, turned out to be very true, for we all had an absolute ball.

Chapter 3

Finally the moment had arrived for our two unexpected young studs to reveal their all, which they did without the slightest hesitation or sign of embarrassment, indicating that they were not fazed by such occasions and proud of their bodies. But what was unusual in guys so young was that they both obviously were into what I suppose must be called cock culture. All pubic hair had been scrupulously removed from around their cocks and the cleft between their buttocks. As soon as they had stripped off, both their cocks had immediately sprung to attention and were ready for service. Both Dave and Zach were circumcised, as are most young American men, and not a trace of foreskin remained to detract from the  beauty of their cock-heads, both of which were set off from their magnificently proportioned shafts by a well-defined rim. Both mouth-wateringly attractive ensembles were enormously enhanced by the total lack of pubic hair.

But not content with their natural endowment, both Dave and Zach had seen fit to embellish their most precious assets, their cocks and balls, with jewellery. Both guys had had their cocks pieced and were wearing a custom made Prince Albert ring. However, this was not just any Prince Albert piercing, but one which had been done with great expertise and considerable aesthetic taste. In each case, the heavy gold ring chosen had been carefully fitted so that seen as it now was with the penis erect, it emerged from the meatus and closely followed the contour of the underside of the distended cockhead before disappearing into the hole pierced on the lower side of the shaft. But this was not all, for both Dave and Zach were each wearing a three dimensional, cage-like cock-ring, the aim of which is to ensure that even when flaccid, a guy’s penis and balls are well presented and do not just hang woefully there.

These trianguloid – to coin a word – cock-and-ball rings are three dimensional in concept and are made of three, separate, rings, which are brazed together to form a pyramidal, cage-like structure. The largest, base ring fits over the wearer’s penis and balls and sits flat against his pelvis. His balls are then inserted one-by-one through the lower ring and finally his cock through upper ring. The whole device is designed to ensure that the wearer presents his sex tools in a stunning manner at all times. When flaccid, the cock, which is held high, descends gracefully over his balls, which are held by the lower ring away from his body. When hard and primed for action, as both Dave and Zach now were, the cock and balls are held rigidly in a cannon-and-gun-carriage-like like manner. Frankly as Dave and Zach, completely ready for sex as they now were, with their sizeable cannons primed and ready for firing, were the stuff that dreams are made of.  I felt my own cock twitching at the thought of what I wanted and hoped I would soon be able to do to and with both young men.

In a way, I was envious of Dave and Zach, who clearly had the courage of their own convictions to lead the life of gay, young swingers; to lead their sex lives as they wished, which they obviously were doing, In retrospect, I regretted that I had hesitated so long before freeing myself of my sexual hang-ups. Looking at this magnificent pair of sexually highly-experienced young studs, I already knew that they would, this very evening, provide a sharply critical, independent sounding board for me to confirm whether or not I possessed the transcendental, copulative powers, with which both Carlo and Alan claimed I was endowed. Looking at Dave and Zach, I could barely contain my excitement as I waited for a sign from our host for the games to begin. But I reckoned without Alan’s penchant for CCP, which he had decided to visit upon our unexpected and unsuspecting young partners.

“Well, gentlemen, before we give way to our carnal urges, there is something which we need to attend. Our two new young friends here here do not know is that as a group of communicants we maintain the highest possible ethical standards. It is not enough to come here to one of our meetings, however well equipped you are, and expect to be received with open arms unless you meet our high moral standards in terms of our general conduct.”  

I could not believe my ears as I listened to this load of load of utter tripe which Alan was spouting, essentially for the benefit of Dave and Zach.  He was leading them to believe that the four of us met regularly for gay sex, which was not the case, as we had never got together until this evening. However, as he reached for and unhooked a cane from one of several on the wall, his intentions became crystal clear to me. As a devotee of corporal punishment himself, he intended to introduce Dave and Zach to the bite of the cane as an arousing prelude, before allowing them to exercise their visually superb, sexual attributes on the rest of us.  I wondered how he was going to sell this idea to the two college lads, and what would be their reaction when they learned that they had to submit their asses to a thrashing if they wanted to have sex with the rest to us this evening.  I hoped he would succeed in what seemed to me to be a task equivalent that of selling refrigerators tot Eskimos as I personally wanted desperately to fuck both Dave and Zach, both of whom were just so physically very attractive they made my cock ache for relief.

With the cane now in his hand, Alan continued. “So one of the requirements, which we exact from newcomers such as you boys,  

is that they do penance for their sins before being allowed to exercise their libidos with us. Now, Dave, in your case, you have a committed quite a number of faux pas this evening. I think you will agree that abandoning your next customer and bringing his pizzas here was motivated purely by your own carnal desire to participate in what you perceived as an evening of hot, gay sex. Now, even though you intend to pay for the goods which you diverted from your next customer and brought them here instead, you left both the customer and your employer in the lurch: and then, to add insult to injury, (My god he was laying it onto poor Dave in spades) you then invited your buddy, Zach, to join us, without even informing us of the fact, until Zach himself arrived at the door. And you, Zach, should have been more cautiously perspicacious before accepting what was more or a less a second-hand invitation to join a party for sex in  private house with a group of guys whom neither of you knew from Adam.”

“So although you two young men are physically very attractive and I am sure would make a very positive contribution to the success of this evening, you have both departed from the high moral standards to which we, the members of the group hold ourselves. It pains me to say that unless you are willing to suffer retribution for your sins, I am afraid that you must put back on your clothes and leave.  However, if you both agree to suffer the pain of the cane applied to your bare asses, then I think my friends and I would agree that you had shown sufficient  backbone to expunge your sins and I think that we would all agree that you could stay and and make your obvious  physical talents available to us all. So what do you say?  Are you willing to take a beating on your bare asses or do you prefer to leave?  It’s entirely up to you.”

I could barely believe the utterly pretentious, over-the-top, moralising piece of clap-trap I had just heard. But I figuratively took off my hat to Alan for his imaginative effort to sell the unfortunate lads the idea that if they were willing to suffer a beating for their supposed sins, then they would then be allowed to enter the Promised Land, flowing not with milk and honey, but with sex, sex and more sex. I did think that Alan himself was committing a much greater sin than those he was pinning on the two lads, in that much of what he had just said was totally untrue; but that was between him and his conscience. I personally hoped that Alan’s little speech, talking to the lads like a Dutch uncle, would not have frightened them off and that they would feel that the pain of a beating in exchange for an of a evening of what promised to be quite exceptional sex with a group of four guys, all of whom, as they could see for themselves had great credentials, was a good deal.

In the event I need not to have worried that I would be denied the pleasure of exercising my cock on our two student friends, for almost without hesitation, after looking at each other, and shrugging their shoulders resignedly in a sign of capitulation, they agreed to Alan’s terms. What an inescapable magnetic force sex is; one should never underestimate the power that it exerts on man’s actions.

“Good,” said Alan, “I am pleased that we see eye to eye on that; so shall we get started as we are wasting valuable time jawing when we could all be copulating.” 

I did not exactly agree his statement that it was we, who were wasting time jawing, as what jawing had been done had been done solely by Alan himself. But what happened next took me completely by surprise.  Alan handed me the cane, which he had hitherto been brandishing under the noses of Dave and Zach, saying, in a measured and sanctimonious tone of voice, with phraseology more suited to a church confession than to a room full of guys who would shortly engage themselves in a free-for-all sex party: “Stan, I too must plead guilty of certain misdemeanours, (You can say that again, I thought) the details of which I will not burden any of you with. So I feel that I too must purge myself of my sins in exactly the same that Dave and Zach are shortly to experience, before we share our bodies with each other. I wonder, therefore if you would if you would kindly give me twelve cuts with this cane across my naked ass before Dave and Zach face their own purification, to show them that in our group everyone is treated equally.”

I realised that Alan was being somewhat altruistic about the reasons for wanting a beating himself, as both Carlo and I knew of his masochistic love-affair with the cane before sex, as I imagined did his partner, Jeremy. But Dave and Zach both had faces of incredulity at what they had just heard, which served to make their own punishment just. Here was the very man who had sentenced them to a beating, who now was willing to take the same punishment himself for unspecified sins of his own. As a public relations coup it was totally unbeatable.  Alan’s stock as a man of integrity went through the roof for our two young friends.  But what it told me was that not only did Alan himself enjoy being beaten prior to sex, but that he himself also enjoyed beating others and seeing others beaten.

Anyway, by the time we had all pulled ourselves together after this astounding announcement, Alan had already stretched himself across one of the tables and was offering his naked buttocks for caning. “Well, Stan, what are you waiting for? Let’s get on with it and be sure that you lay my twelve strokes on properly. I really want Dave and Zach to see that I have been been well punished before we go on to decorate their asses with the cane.”

Looking at Alan’s ass, I could see no signs of any recent cane marks, so I guessed that he might be suffering from withdrawal symptoms as he had clearly not been caned for quite some time; by now I had cottoned on to the fact that the cane, for those who enjoyed being beaten, is as addictive as heroin.  Knowing of his declared love of the pain of the cane, I did as he had requested and, quite frankly, surprised myself in that I took great personal pleasure in giving his ass absolute hell. I felt he deserved to suffer as much as possible by way of retribution for his treatment of Dave and Zach, who had done nothing to merit the sort of beatings for which they were now waiting. The pleasure I personally experienced as I laid on the cane to Alan’s backside, together with the  extreme sexual arousal which I felt, was the first intimation to me that I had possibly a sadistic element in my make which I had hitherto not recognised.

I wondered how Dave and Zach were feeling, having witnessed the brutality of the beating I had just given Alan; I supposed that both of them might be on the verge of shitting bricks now that they had seen the ramifications of the punishment to which they had agreed to submit their own bare asses. But there was now no going back; the die was cast; Dave and Zach had agreed to be caned because they obviously thought that the evening of sex which was to follow was worth the pain; a sort of riches in heaven mentality. But I asked myself if they actually knew just how much pain a simple cane was capable of delivering. Many American boys, not least myself, have experienced the paddle whilst at school; but the pain delivered by that traditional American implement of punishment can in no way be compared to the vicious bite of the rattan cane as it etches its deep furrows of pain into the naked flesh of a recipient’s buttocks.

The scene in Alan’s recreation room at that moment was just about as erotically phantasmagorical as anyone could imagine. Here were four young studs, (Jeremy, Carlo, Dave and Zach)  all totally naked; all of them sporting enormous erections, their cocks totally aroused and dripping with pre-cum, proof, if any were needed, of the apparently incontrovertible premise that sex and corporal punishment are closely linked together in the male  psyche; all waiting to see what would happen next. In many ways it was like the first act of a play in which the curtain had come down on a scene, which left the audience on the edge of their seats, biting their nails, wondering what was to happen next.

The dramatis personae to the action so far, had been Alan and me, with me playing the active role,  which as Alan soon made clear, was yet far from over. I confess, that I myself, as dispenser of Alan’s beating, was probably the most sexually aroused of the whole company. As I delivered the last of the twelve, truly swingeing strokes of the cane to Alan’s arse, I glanced at my own massively erect cock, which was dripping with pre-cum like a leaky tap. But as Alan now made clear, my role was far from done, as he said: “Well done, Stan, that was a truly satisfactory beating and I feel much better for it. However, Stan, to make things absolutely perfect, I suggest that you now use my ass to demonstrate to the others, particularly to our young friends, Dave and Zach, your unique ability with your own rod, which as we can all see is just raring for action.”

So not only had Alan got me to flog him, but now he wanted me to fuck him in front of the assembled company.  You will remember that Alan was the only man, other than my partner, Carlo, with whom, until a few brief weeks ago, I had ever had sex. Since that occasion, on which, after his first and only experience of my apparently unique sexual capability, Alan had figuratively drowned me in praise and had immediately urged me, then a comparative naïve beginner at gay sex, to consider becoming a Male escort, I had not seen him again until tonight.  But here he was, based on what had been a one-night-stand with him, asking me to perform on him, in front of the others, what was tantamount to a master-class in anal sex to show how on one male  should fuck another.

I confess I was astounded, but also extremely flattered, by what he was asking me to do: to use his arse to give an expert demonstration of anal sex on the basis of one previous sexual experience with me.  It sort of placed me on a pedestal: the acme of gay sexual operators, making me, by implication, the bench mark against which all others should henceforth be judged. In one way, it made me swell with pride that I had inspired such confidence in him after only one encounter.  But as he had, at the time, waxed lyrical about that first and only experience he had ever had with me, I discerned in his present suggestion, on face of it altruistic, a personal desire to be the first man that evening to enjoy, for the second time, a renewal of the intense orgasm I had given him on our first union. I was genuinely convinced that he had meant what he said about my exceptional capabilities  after that first time that I had fucked him and that what I had done to him was, for some reason, in his eyes special. It was almost as if he wanted to be the first that evening to experience my cock up his arse whilst it was still fresh, before it became jaded by the demands of an evening of no-holds-barred uninhibited sex.

I was surprised with myself that I did not feel unduly nervous at the prospect of giving what amounted to a sex-show to the others. In fact, I was rather looking forward to the leading role that had had been allocated to me. Since I had last seen Alan, a lot of water had flowed under the bridge and I had successfully emerged from the confines of the shell in which I had been sheltering; living and having sex only with Carlo; not that Carlo’s effort were to be sneezed at, as he was a brilliant cocksman in his own right and had taught me everything I knew about gay sex.

Thanks firstly to Alan for his surgery on my cock, liberating me from my youthful hang-ups and later to Carlo, I had developed an extensive, if superficially exciting sex-life with an ever-changing selection of men, whom I had never met before, on my regular jaunts with Carlo into the gay hot-spots of Chicago. So it was now a much more sexually confident and experienced Stanley Przewalsky, who was about to take centre stage and show the others how the gay sex act should be performed, than the man, who had just one time previously, fucked Alan Greenberg as only his second sex partner ever.

However, having been unexpectedly been thrust into the limelight by Alan, after digesting the surprise role  I was to play, I decided to grasp the nettle firmly and enact to the hilt, the part of the expert, elder cocksman, with which by implication Alan had, rightly or wrongly,  endowed me. So adopting the attitude of an omniscient teacher explaining a new concept to his class, I decided to say a few words before shafting Alan. I glanced at my audience of four naked studs, all of whom were sexually aroused by what they had seen so far Their cocks were all rigidly erect and dripping anticipatively with pre-cum at the act of gay anal sex that they were about to see enacted before their very eyes.  As I looked down at my own erection, I have to say with some pride that I was proud and impressed by what I saw; ten inches of rock-hard man-meat, surmounted to a well-rimmed head stretched to the limit, which would shortly be the key player in what was to happen next

Until Alan had dropped his first bombshell and asked me to flog him, I don’t think that any of us had anticipated that the evening would develop as it was presently doing. But now, it suddenly struck me what was happening; Scene 1 had been the unexpected flogging in which I had played the key role. But now in Scene 2, in which I was again to play the reading role, fucking Alan before an audience, was a akin to a scenario for a porn video-clip, the likes of which there are thousands, if not millions, extant on the internet, most of which portray anal sex as an act to be completed with maximum vigour and as quickly as possible. But in my own mind, I determined that as the key player, the putative god of anal sex, to which elevated status I had been unexpectedly catapulted by Alan, I would endeavour to play the part to perfection and raise the banal physical act of gay sex to the level of a fine art. I would demonstrate to the four on-lookers and confirm to Alan, as he evidently already thought was the case with me, that anal sex, if treated with respect by the top for his partner, is an act which never, ever fails to please both participants and which can take the sensation of orgasm to unimaginably exquisite heights.

If anyone had told me at the beginning of the evening that I would be demonstrating my sexual expertise by fucking our host in front of his other guests, I would have considered them stark, raving mad. But as is sometimes the case, fact is stranger than fiction and that is exactly what I was about to do. Given the key role in which I had been cast, I decided that a few words from me would be appropriate before I quite literally plunged into the demonstration. And aged only just twenty, I donned the hat of an elder statesman and explained to my audience the ground rules, as if they had been sent down, like the Ten Commandments, by God himself.  Luckily there were only two!

Laying it on in spades, I began: “It is an unexpected honour, not to mention pleasure, to be called upon by our host, who has also graciously offered himself as my guinea-pig, to demonstrate to you this evening, what he refers to as my unique technique in performing the act of anal sex. I am not sure when I fuck any partner that I do anything out of the ordinary, which any of you can do just as competently as I can. But before I begin, my unique technique, if unique it is, I owe solely to the invaluable advise in all matters sexual given to me some time ago by my partner, Carlo, who summed the art of anal copulation up on two sentences: firstly, make sure that you and you and your partner are both well lubricated before you start; secondly, make haste slowly.  If you follow these two simple rules, then all of you will achieve the same results as I now intend to demonstrate to you.” I did not deem it necessary to mention that a good-sized cock helped too.

“We have all, I am sure, looked at some of the multitude of homosexual, pornographic sites on the Internet, aimed at satisfying the innate voyeurism which is in all of us. What I have learned from my own study of these sites, is that when two guys fuck each other, as they inevitably do, the concept of mutualism is practically always absent; and you can almost delete the word practically. Whatever the scenario – and some are very imaginative, involving several guys in mind-bendingly ludicrous, physical positions – it is always every man for himself.”

“The top always seem to fuck his partner as if there were to be no tomorrow; the bottom, meanwhile, whilst having his anus battered, usually attempts to jerk himself off manually. The whole fiasco – for that is what it is – ends with the top withdrawing himself from his partner and joining him in an attempt to climax by jerking himself off. So, as I see it, the net result is the same as if the tops and bottoms simply participated in a masturbation fest, jerking themselves off and sharing their respective cum with each other if they were still schoolboys before they discover the delights of having intercourse with another warm body of either sex.  The idea that the top, by his skill, could manage to take both himself and his partner through to a simultaneous orgasm, free of manual assistance, seems never to have crossed their minds.”

“So, if I do have a special technique, as Alan claims I do, then it is that when I have sex, I always aim to take both my partner and myself through to mutual orgasms.  And make no mistake, the simultaneous orgasm, which both parties experience, is incomparably intense compared to the one produced by masturbation with which we are all a familiar. I my view, masturbation should be resorted to as a last resort, when we are alone, and feel the need for sexual relief.  Mutualism should reign as the key consideration whenever we have sex with another human being; and this alas, much-neglected truth, holds good for both homosexual and heterosexual relations. My thoughts on this cannot be better summed up than by the first words of the 1776 Declaration of Independence of the then thirteen United States of America, begins: We hold these truths to be self-evident. For me sex is a union between equals.”

Thinking  back today, years later, on what I said before I proceeded to shaft Alan that evening for only the second time in my life, I am amazed that I was able to spout in such an orotund and imposing manner, such a load of words about sex as if coming from a man with a lifetime of experience. What I did seriously believe was that all sex was a union between equals and that in gay sex the subservient bottom was just as important as the active top. However, I did not deem it necessary to mention that one possible reason for my apparently unique ability to do what most guys evidently found difficult to achieve, was made possible by my impressively large phallus, which was clearly visible to my audience throughout my discourse. The length of my erection allowed me to make long powerful strokes which the average guy could not hope to equal. This, coupled with its unusual large diameter, allowed me to make every single stroke count in bringing my partner to his climax.

Alan had thoughtfully laid out lubricants and condoms on a side table. In addition to a cream specially formulated for cock lubrication prior to anal sex, were several packs of an anal lubricant called Anolube, presented in the form of individual sachets each fitted with a nozzle allowing the contents to be injected via the anus into the rectum of the bottom, thereby ensuring that he was well lubricated before any penetration occurred. As I was readying myself for penetration, Alan said to the others: “Guys, listen up; I am going to ask Stan to take me bare-back as I want to feel his sperm inside me. However, in the interests of good house-keeping, I myself will use a condom to catch my own cum, which if Stan does his usual job, which I am sure he will, will be copious.” 

I was impressed by his confidence in me, which was based on the one and only time when we had had sex together.  But I can tell you, that his confidence in me boosted my own self esteem and as I prepared to penetrate him, I knew I would move heaven and earth if necessary, to ensure that he had not misplaced his trust in me.  I was not prepared to allow him to be disappointed; I had every intention of doing my copulative best to ensure that I took us both to the sublime conclusion of simultaneous, hands-free orgasms. So what had initially seen the light of day as a demonstration of my unique technique on Alan’s arse for the benefit of the others, had now become a matter of honour: to take Alan to paradise.

As the head of my cock touched against Alan’s anus, I felt that automatic tightening of the muscles, an involuntary reaction of the body to prevent the entry of a foreign object into the rectal passage. But as I insisted, the sphincter muscles eased and my massive cock-head slid inside of Alan’s rectum.  However, as the rim of my cockhead, the maximum diameter of my penis, passed the anal sphincter muscles, they immediately contracted either by design or by my automatic reflex and gripped my shaft firmly directly below the rim of my head, This was only the second time that I was fucking Alan, but I remembered a similar reaction on our first occasion together; a reaction which had never discerned in any of the many partners I had had since my liberation from my sexual hang-ups.

And as on our first occasion together, Alan gripped my shaft firmly and made me work hard to achieve full penetration. Then it suddenly hit me; Alan was a master in the art of bottoming. He had clearly trained his anal muscles so that instead of being at the mercy of the whims and pleasures of his partner of the moment, he exercised considerable control over what was happening to him; he was no longer just a totally a submissive bottom whose hole was being fucked. By gripping of his partner’s penis, he extracted the greatest possible pleasure from the enormous amount of energy which is always expended by the top partner in the act of copulation. Alan was showing himself to be as unique a bottom as he claimed that I was as a top.

But my immediate task as I saw it, was to bring us both to that exquisite state of nirvana, which I was totally convinced, whether homo- or heterosexual, could only ever be achieved by the mutuality of a simultaneous orgasm in both parties to the act. That is what I wanted to share with Alan. But as such intense feeling can only ever be shared by partners to the act, I also wanted, for Alan’s sake as I had been presented to the others as the be-all and end-all of cocksmen, to demonstrate to them, the physical gymnastics leading to the desired climax in both parties. His very words: your unique ability with your own rod, were still ringing in my ears as I prepared myself to prove them in front of the others. Should have felt nervous with my star billing, centre stage as I was? Of course I should. Did I feel nervous? No not at all. You see, all the praise I had received about my uniqueness, had gradually brainwashed me into half-believing it might be true, and so it was with considerable confidence that I started my demonstration fuck of Alan’s arse.

Having achieved the first stage and buried my full ten inches  as deeply as I could inside Alan, with my own pelvis pressed tightly against his anal area, I paused for several seconds; partly because I wanted to enjoy the sensation of being deep inside my partner, who was now gripping my meat by the root, indicating that he intended to make me sing for my supper; but also because I wanted to bring home to the others the importance of making haste slowly, as the top, by skilful use of his cock, gradually brings both parties to the act to the final glorious climax. After the initial pause, I withdrew my dick virtually completely from Alan’s anus, until my entire shaft below the rim was exposed. Alan’s sphincters held me firmly as he extracted every ounce of frictional pleasure from my withdrawal, before gripping me, vice-like, directly beneath the rim.

And now I began my normal, unhurried style of fucking my partner, giving him my full length on each forward thrust. As Alan maintained his muscular grip on my shaft both as I thrust and withdrew, we both derived the maximum sensually erotic sensation from every movement I made.  Then as the act progressed, I gradually increased the speed and power of each thrust, always withdrawing myself more or less completely, but not quite, from him. Inevitably as time progressed we both became ever more erotically aroused until I saw that I had taken Alan to the point of no return, by which time he was begging me not to stop. At that point, I knew I had succeeded and withdrew myself completely, held my cum-dripping cock clear of his hole for two seconds before plunging myself with tremendous force and speed in that one final coup-de-grace aimed at bringing both of us to that state of pure and unadulterated bliss, of orgasm, with which no other experience in life can compare.

Chapter 4

As soon as I bottomed my pelvis against Alan’s anus in that final, powerful stroke, I knew I had succeeded; succeeded beyond my wildest dreams, for the intensity and length of the orgasm, which I personally experienced, was beyond anything I had ever encountered during my sex life to date. As I pumped what seemed at the time, an endless load of my own sperm into Alan, I could feel from the uncontrolled jerking of his body, that he too was in the grip of an orgasm of incredible intensity as he filled the condom he had wisely chosen to wear, almost to the bursting point with his own jism.

The assembled company gave us – and I say us, rather than just me, as what I had just achieved was not down to my efforts alone – a resounding round of applause. The onlookers, of course, seeing only my movements as the top to the act they were witnessing as I fucked Alan, could have no idea of the invisible part he was playing or that the intensity of the orgasms which shook both bodies as we simultaneously climaxed, were due in no short measure to Alan’s control of his anal sphincters. But when the climax came, it was evident to everyone that they had just witnessed an exceptional master class in the art of anal copulation as the bodies of the two protagonists to the act shook with that uncontrolled emotion orgasm always engenders,

But whether or not the onlookers fully appreciated the ramifications of what they had just witnessed, one thing was sure: I had successfully demonstrated that the anal sex act should always be considered as a mutual union between the two parties; and that the top, by treating his bottom partner with respect, not only could, but also should, satisfy the sexual need of them both.

The fact that Alan had sort of formalised the proceedings of what I had originally foreseen as a relaxed evening of free-style sex among the four of us, had been turned into what was to become a teach-in for Dave and Zach of the finer points of anal sex. So what happened next was that the two college studs wanted me to do the same to them as I had done to Alan. Whether it was just my size which attracted them – after all, it is not every day that a guy has the chance to take ten inches of man-meat wielded by a highly effective operator up his ass – or whether they hoped that I would take them to that paradise of orgasmic intensity, which they had hitherto not known existed, is a moot point. But what was clear was that after my demonstration with Alan, in plain and simple language, they both wanted me to fuck them.

However, Dave and Zach seemed to have forgotten their part of the bargain. Alan however, reminded them that if they wanted to be admitted to the Garden of Eden, their own arses had to suffer the same fate as he himself just undergone.  The original agreement was that if Dave and Zach were to be allowed to stay and join in what they obviously saw as an evening of uninhibited, sex, they each had to take   a beating to purge their so-called sins, before being allowed to participate in the sexual fun that was to follow.

What had not, however, been specified, which now became patently obvious after the fact, was that having witnessed the result of my ministrations to Alan’s anus, the two young studs were straining at the leash – in fact, almost salivating  –  at the expectation that I might do the same for each of them. So eagerly transparent were they both, their desire to experience the utter ecstasy, which they had seen me bring to Alan, painted on their faces, that on being reminded of their part of the bargain, they immediately went to opposite ends of the table from which Alan had now risen and offered their asses for punishment.

A feeling of relief surged through me that they were still willing to take a beating to be allowed to stay; as I observed earlier, I personally had been relieved when they originally agreed to Alan’s rather draconian; terms, as I found them both physically highly attractive young men and was looking forward with pleasure to having sex with both of them before the night was out. But what had not been made clear was which of us, Alan, Jeremy, Carlo and me, was to do the dastardly dead and shred the two, lily-white arses now in front of us. Alan appeared ot have decided for us, as he picked up the cane and handed it to me.

In view of my newly discovered awareness of a distinct sadistic streak in my make-up of which I had been totally unaware until I had beaten Alan early that same evening, I now found that in spite of my initial a reluctance, I had no objection to striping the arses of the two young studs; in fact, being brutally honest with myself, I knew I was really looking forward ot it. However reading the figurative tea leaves and anticipating what I was as certain as anyone could be of the hopes of both Dave and Zach, which I frankly looked forward to fulfilling, I went across to the wall, where Alan’s canes were hanging, selected one and handed it to a much surprised Carlo.

I then said, as much for the benefit of Carlo as for that of two young men lying prone across the table: “Look guys, there are times when some straight talking is called for; and this is one of them. Carlo, who is my life’s partner and who is the the person who has taught me everything I know about sex, and I are each going to beat you. You will each received six cuts of the cane from both Carlo and me: twelve cuts in all, which believe me, will hurt. And then in the interests of declaring tonight’s sexual fuck-fest open, Carlo and I will each fuck the man whom we have just beaten. But then to deprive neither of you the entire experience, we will then switch partners. So, gentlemen you will have had what I hope will have proved to be the whole enchilada. You will both have been fucked by Carlo, the master and me, his pupil. And I can but say that Carlo and I will each do  our best to take you through to orgasms so intense that you will find it well worth a twelve cut beating, which I suspect and hope, that you may ultimately find you have both enjoyed.”

So what finally happened was that after thrashing the two of them, Carlo and I each shafted successively both Dave and Zach, as it had become clear, from what had become an unspoken request for my own services from both young studs, that I personally would not be allowed to escape without sharing what they clearly saw as my unique expertise with both of them. This left Alan and his alter-ego, Jeremy, twiddling their thumbs or contemplating their navels or both, wondering what to do with the demand for action from their own cocks, both of which were making their desire for attention manifest by standing stiffly to erection and leaking cum.

I suppose that Alan and Jeremy could, have gone ahead and fucked each other as interim measure to tide them over until our quadrumvirate finished its dual round of beating and copulation; but that would have been old hat, as like Carlo and me Alan and Jeremy were very much an item. And so, much to my surprise the two of them decided to associate themselves physically with what Carlo and I were doing with Dave and Zach. I suddenly felt a cock slide into my own anus as I paused for a moment in my thrusting; glancing over my shoulder, I found that it was Jeremy who had stuck himself up my arse; Alan, meanwhile, occupied himself similarly with Carlo.

So that was how the free-style evening of uninhibited gay sex among the six of us really got started. Other than that Carlo and I both successively and successfully first beat and then fucked both Dave and Zach through to their first hands-free orgasms, I have no recollection of what I subsequently did to whom nor of exactly what was done to me. Suffice it say that we had an absolute ball. At four in the morning, after Carlo and I had returned to our apartment and fallen into bed together, Carlo summed the whole evening up in one pithy sentence: “That was one hell of a party and thanks for including me in your moment of glory with Dave and Zach. You know, Stan, you really are the tops; you are just a great guy in every way and I’m lucky to have you.”

Chapter 5

Not surprisingly, next morning, which was Saturday, we both slept late. Carlo was not on duty at the gym until one o’clock and so, over a leisurely, late breakfast, sitting naked at the table, we had time to chew the fat over last night’s party. Carlo began: “You do appreciate, don’t you, Stan, that Alan made last night’s fuck-fest yours for the taking?”  As I obviously looked puzzled, he went on: “Oh come on, Stan, use your brain and accept what you actually saw.  Look, Stan, Alan, arranged last night’s shindig solely for your benefit and he profited from the unforeseen and impromptu arrival of Dave and Zach, to highlight even more your remarkable capabilities when it comes to gay sex. Do you think that his request for you to beat him and then fuck him was made on the spur of the moment?  If you believe that then you must also believe in Santa-Claus.”

“No, Stan, Alan was intent from the word go in getting you to see that you have a gift that we others don’t have. I don’t say that you are unique, but when you fuck a guy through to orgasm, as you always do, you show him a side of gay sex, which most guys do not even know exists.  You, Stan, raise the act of anal sex to the level of a fine art. And that was the main purpose of Alan last night: an attempt to make you finally realise what he and I have both told you previously: that you are sexually a very gifted guy and that you should make the most of your talents. But when Dave and Zach arrived like an unexpected gift from heaven, Alan saw an additional opportunity to hammer home his message. Why do you think he chose you rather than Jeremy or me to beat Dave and Zach, when he could equally have had the pleasure of thrashing the two young studs himself?”

“But speaking of the pleasure of inflicting pain on others, I also observed last night, as you thrashed first Alan and then Dave and Zach, you really enjoyed giving all three of them hell prior to fucking them, So my guess is that, in wielding the cane, you suddenly discovered a side of your character which you had not realised existed until then: that you yourself have a hidden sadistic streak and actually enjoy beating arse.  I watched you very closely as you thrashed Alan and I saw that with each successive stroke your erection hardened, so that by the time you had finished shredding his ass, cum was dripping from your cock as if it were a leaking tap. Frankly you were already so aroused when you finally got around to shafting Alan, that I marvelled at how you were able to stop yourself dumping your load prematurely and leaving Alan, figuratively speaking of course, high and dry and singing, not for his supper but for his missed orgasm. But of course being the expert you are, you were able to control yourself and take both yourself and him though to that magic moment of the simultaneous orgasm, a concept which you have made your own.”

“Look, Stan, I agree with what Alan suggested to you that first time you fucked him in lieu of paying him his fees for the work he did on your cock. You have quite exceptional talent and you owe it to yourself at least to try to use it. And I am sure the basic reason for last night’s party, which was an absolute blast, by the way, as the six of us fucked each other silly through into the early hour of today, was to bring home to you, yet again, what is blindingly obvious to everyone but you, or so it would appear, that you have both an exceptional cock and a talent for using it for its god-given purpose, the likes of which few men have. Mark my words, Stan, you have not heard the last of Alan on the subject for he is, for some reason, hell bent on pushing you into a career in which you can use your talents, which he knows will satisfy you. And you know what? I agree with him. You are wasting your time in that dead-end job you have at the supermarket when you could be doing something so much better: something that you are good at; something which you will find personally much more satisfying  and something at which you can earn a very good living.”

“Now, lover-boy, as we have two hours before I start  at the gym this afternoon, and as we are already stripped for action,  I propose to reward your patience by giving you another chance to confirm your status as the absolute bees-knees of gay cocks-men, by allowing you to fuck me yet again. You will as my partner appreciate that as regular recipient of your efforts, I personally do not need any further confirmation of your abilities. But as I sense a certain reticence on your part for you to recognise and acknowledge your own talent, I have decided on this occasion to act, once more, as your guinea-pig in the hope that you will eventually see the true light and accept that you have an exceptional cock and an exceptional ability in using it.” Carlo concluded his flippant remarks with a laugh,

However, I can give as well as I can take so I said, equally flippantly: “Carlo, I love you dearly; but have I ever told you that there are times when you push condescension to the absolute limit and begin to sound like a pumped-up, pompous, pretentious prick. Well allow me to tell you that right now is one of those times.  However, being, as always, prepared to bend myself to please you, on this occasion, as usual, I will accede to your whim, for to deprive you of the sex you are obviously craving, would be to deny you what you clearly consider as the staff of life.  You my friend need sex on a daily basis, like a blood transfusion, to keep body and soul together.  So let’s forget the tripe you have just spouted about you doing me a favour to allow me finally to recognise my own talent.  I know what I am capable of and I know that without a regular dose of TLC from my cock you, my friend, would just fade away to a shadow of your resent self. So get yourself back onto the bed and I will meet your wishes in the doggy position as best befits the moment. Believe me, Carlo, I intend to nail you to the bed and leave you panting for more. So, my friend, prepare yourself for the worst – or should I say, the best? – as I intend to give you the hardest fuck of your life. People like you, Carlo, who play with fire, are liable to get burned and I am looking forward to using my cock as a branding-iron on your arse!”

After this persiflageous exchange of words, we both retuned to bed, giggling like a pair of school girls, In spite of my rhetoric, as ever, I found it impossible to walk away from my shadow; so first in the doggy position and immediately after, in the face-to-face mission position, I took both my belovèd Carlo and myself in my normal, unhurried manner, twice in half an hour, to the heights of orgasmic pleasure. As we lay there in post-coital bliss in each other’s arms, Carlo once again told me that I was just the greatest performer ever. The old maxim rang through my head: Sexual intercourse is a toy which never fails to please. And certainly when I was the top and doing the fucking, judging from the comments I receive, it seemed always to be true.

But when I thought of Carlo as my belovèd, I suddenly realised that therein lay my hesitation; my reluctance to accept what I knew in my own heart to be the truth of the matter: that I did really possess exceptional copulative powers and that I could probably make a living as Alan was urging me to do, selling my sexual talent to other men as a male escort. But I was hesitant, fearing that if I were to embark on a career of selling myself for sex to other men, it might destroy the most precious thing in my life: my relationship with Carlo. Would he be content to live his life with a partner who was having sex for money on a professional, basis with unknown men more or less daily?  It was almost a remake of the nightmare scenario which I had feared before I had had my cock cut by Alan Greenberg: the fear that on one of his solo forays into the gay sex world of Chicago, Carlo might find someone else he fancied more than me and leave me high and dry. Now, however, it was the thought that any of my activities might drive Carlo away from me that was just too awful to contemplate. I was totally and completely, hook, line and sinker, so deeply in love with Carlo, and even to think of losing him was an untenable anathema. so if to keep him, meant my remaining in my job at the supermarket; then so be it.

As we lay there in each other’s arms, I decided that this was the moment to try to resolve the question which was perpetually on my mind: should I or should I not even consider attempting to make a career out of selling my body for sex? I knew that the answer to this question would entirely depend on Carlo’s reaction to the cold hard fact, that if I were to be successful, his life’s partner would be earning his living by fucking other men. I had been dithering about making a tentative attempt to try to become a professional male escort ever since Alan had told me that I had something quite exceptional to offer, which exactly echoed Carlo’s earlier remarks. What was quite remarkable was that Carlo and Alan had made their remarks to me after I had had sex with each of them only once.

This had been a revelation to me. I, a complete newcomer to gay sex, had received lavish, unsolicited praise for my performance from two highly experienced gay men; and like most people I was gratified to be praised. Couple this with the comments I had received from men I did not know, each of whom I had fucked just once on sorties with Carlo into the free and easy gay sex-life of Chicago. And then at last night’s party I had again collected lavish praise from everyone. So it is not surprising that the cumulative effect had finally convinced me that exceptional or not, I did have something which to offer in the gay sex stakes that guys seemed not to have: and that something, whatever it was, was, crudely put, guys just enjoyed being fucked by me.

But sometime I had to bite the bullet and decide, yea or nay, did I want to pursue the idea of earning my living by selling sex. As I have explained, if Carlo were to raise event the slightest objection, then I would drop the whole idea like a hot brick, as I would do nothing whatsoever, to prejudice our relationship, which had become the most precious  in the world to me. Anyway, basking in the aftermath of a joyful hour of intense sex as we were, I finally plucked up my courage and said: “Carlo, I’ve been thinking seriously about Alan’s suggestion that I quit my job at the supermarket and attempt to become a male escort. I just wondered what you really thought about the idea. After all, if I were successful, you would find yourself cohabiting with a guy who was living off his immoral earnings. So, what do you really think about the idea?”

“Jesus H. Christ, how many time do I have to tell you the truth about what is staring you in the face and is blindingly obvious to everyone but you, or so it appears? You know I thought in our pre-sex, breakfast discussion that I had made my position quite clear; however, seemingly not clear enough to get through to you to stop you dithering around and finally make some decision. So, lover-boy, listen-up one last time as I tell you the facts of life as I see them’ and I shall not tell you again, otherwise  I shall begin sound like a broken record.”

“You, Stanley Przewalsky have finally got to face the fact that you are a totally exceptional man. Not only do you have a superb cock, which drives the rest of us mad with envy, but you also have a superb body, thanks to our work-outs together in the gym over the past few years. When did you last strip naked, not for sex, but to look at yourself in a mirror.? My guess is never; if you had done so, you would realise that you have the physique of Greek God. (Carlo echoed Alan’s when he had made a similar flattering comparison between and the Greek deities) But then on top of your physique, when you have anal sex with a guy, as you enjoy doing, you take the experience to unbelievably erotic heights, which most of your partners did not even know existed until you shafted them. I know I certainly didn’t; and I told you so the very first time you fucked me when we were still at that hellhole of a school together.  And my guess is that Alan had the same revelatory experience the very first time you fucked him, which made him immediately suggest that you think about becoming a male escort.”

“So, for what it is worth, my advice to you is to go ahead and try to become male escort.  If you don’t succeed, then there are always some dead-end jobs around which you can go back to. But I reckon that you will succeed and you will be earning your living by doing something you are good at and which you really enjoy; and you will be independent to do as you wish.  So, Stan, you have my blessing if you decide to try. If I were you, I’d just go for it!”

“But Carlo, do you mean that you would be easy about living with a guy, your partner, with whom you have two-way sex regularly, who at the same time is using his cock more-or-less on a daily basis to earn his living?  Look, before my operation when you used to leave me on my own when you went off in search of casual sex in gay clubs in Chicago, I was insanely jealous of the guys you were fucking, whom I did not even know. My biggest fear, when you left me twiddling my thumbs whilst you went off enjoying yourself, was that you might one day find someone you preferred to me and leave me high and dry on my own. If I go off on a daily basis and have sex with some guy for money, don’t you think you might feel the same way?”

“Look here, Stan, just consider what our sex life consists of now. You and I live together as an item, but it does not stop us going off together to the gay joints in Chicago and having sex with guys whom we do not know and will probably never see again. Then take last night; we both went to Alan’s party, knowing we were being invited for an evening of sex and we had an absolute ball. Did you feel jealous of me or me of you when we both successively thrashed and then fucked Dave and Zach, Hell, we did not, as it was all part of the fun, And did I feel jealous of you when you were selected to thrash and fuck Alan, thinking it was a ruse to draw you away from me as I knew he was enamoured of your ability?  Hell no! Of course I didn’t!  And afterwards, what did we then do? Well as usual, we came back here and fell naked into bed, as we always do. Then this morning you finished up shafting me twice, confirming, by the way, not that any confirmation was needed, that you do have something special; and now here we are having this same interminable discussion, still in bed together, when I could be return fucking you before I leave for work. Waken up buddy; there is nothing on earth that is going to destroy our partnership. It was pre-ordained that we were to find each other and be together; so just accept that as an immutable fact.”

“It’s time you got real Stan and faced the facts; which are staring you in the face. Look, Stan, neither you nor I are monogamous; we both like to fuck around. We have a great and varied sex life together; based firmly on our rock-solid relationship with each other and we both enjoy the excitement of clubbing for sex in Chicago. Additionally I think we have found in Alan and Jeremy, and in Dave and Zach two other pairs like ourselves, with whom I suspect that we can develop friendships which go beyond just meeting them for recreational sex. Why should we want to change any of that?”

“So for one last time, let me repeat; if you want to chance your luck and try to make a go of being a male escort, as far as I am concerned, just go ahead and try.  Look, all it means is that you earn your living by giving other men the stimulation they need, whilst I earn mine by helping them to develop the bodies they want. And let’s be quite clear about that, as you already know, I do myself have sex with some of the clients who are just so sexually attractive and make their wishes too obvious to ignore.  So why turn our noses up at something which is offered to us on a plate. But all this you already know and it has never interfered with our partnership. Look, Stan, both you and I are guys for whom male male  sex is already an important factor in our lives; it is something that neither of us can live without;  so just accept the fact and enjoy life.”

“Yes, yes, Carlo, I know all that; but being a male escort is quite different to the sort of sex we indulge in at present. Fucking guys for money would be my permanent job, a job I would be involved in every day, which might change everything and might ruin everything which we have together at present.”

“Horses arseholes to that, Stan. As far as I am concerned it would change nothing, other than the fact that you would probably earn a lot more than the pittance they currently pay you at the supermarket and you would be doing something you are both good at and like doing. So, just stop wringing your hands in woe, lamenting what might happen, but never will and stop pouring self-guilt and doubt on yourself. You have to stop pussy-footing around and make a decision one way or another. You have a remarkable gift given to few men; so for crying out loud, use it! And that, my friend, is my final word on the subject. It’s your decision to make. If it makes you feel any better, I love you dearly, Stan, and would never, ever let anything come between us. Now kindly turn over so that I can get my cock into your ass in an attempt to fuck some sense into you before I have to dress and go to the gym.”

At that moment the telephone rang; and as Carlo had predicted, it was Alan, who suggested that that same afternoon, he and I have another talk about matters of common interest, was the way he put it. “You see,” said Carlo triumphantly, “I told you so; Alan is not going to allow you to walk away from the opportunity of a lifetime.”

Chapter 6

Late that afternoon I went access to Lake Point Tower to see Alan again. “Well, Stan, I’m glad to see that you are still standing after the exertions of last night. That really was quite some party, wasn’t it? Unless you hadn’t noticed it, you were the star turn. The unforeseen arrival of our two new friends, Dave and Zach, allowed you personally to shine and demonstrate your unique ability with your cock. By the time you and Carlo had finished with the two of them, they were in seventh heaven, I don’t think that they even appreciated that sex at the level you delivered it even existed, before you gave them pleasure of sampling your cock. Carlo isn’t bad either; and I can see that you are a well-matched pair; but he is not up to your standards by a long chalk; but then who is?”

“But, but last night, when you fucked me for only the second time, you confirmed what I already knew to be true:  you have a cock in a million, which you use in a unique way, that transcends anything I, and I dare say all others, have ever experienced.  No one, in my experience, which, not to sound boastful, is pretty extensive, holds a candle to you when it comes to anal sex; and I am not speaking only for myself, for I observe you last night, as you always managed to take your partners to the heights of ecstasy of the simultaneous orgasm, the intensity of which beggars belief. I kid you not, Stan, but anyone who has the indescribable pleasure of experiencing your cock up his ass, should thank god for the privilege. You had not only me, but the entire company last might eating out of your hand. I tell you, in spite of thrashing their arses raw with the cane, Dave and Zach absolutely worship you after what you later did for them.”

“This brings me to the subject of corporal punishment, which I personally find is the perfect prelude to anal sex.  The first time I asked you to cane me, I saw at the idea was repugnant to you. But last night, when you caned me and then, at my urging, together with Carlo, went on to thrash Dave and Zach, I discerned a change in your attitude. I myself felt, as you applied the cane to my naked ass and then observed as you caned Dave and Zach, that your attitude had changed, as it seemed to me that, this time, your heart was in what you were doing.”

“Well, Stan, all this preamble brings me to the purpose of why I asked you to come around this afternoon, as I am sure you might already have guessed,  I am burning to know whether you have given any serious thought about using your  unique capabilities professionally and becoming a male escort. My own view is that you are wasting your talent; you are hiding your light under a bushel, working in a supermarket when you are not only capable worthy of so much more. So, after six weeks of liberation from your foreskin hang-up, I assume that you have not allowed the grass to go under your our feet and have tasted the delights of being cock-loose and fancy-free in the Chicago gay world. I hope that your experience, which, by the way, was apparent last night in the way you acted, has confirmed my initial diagnosis that you do have something special, which will allow me to make a great prognosis for your future in the sex business. I have to say, Stan, that after your stellar performance last night, I have great hopes for you.”

The enthusiastic way in which Alan went on and on about my uniqueness , would have led a casual listener to believe that my conversion to a successful, leading male escort, was a fait accompli and that it was all over bar the shouting, when, in fact, nothing could have been further from the truth. It is true that the original enthusiastic comments I had received, first from Carlo and then from Alan about my uniqueness, reinforced by the comments from different guys, with whom I had had casual sex on my many forays into the Chicago world of gay sex, had finally convinced me that I was different from other men. Alan’s party yesterday had served to hammer home the same message in eulogistic terms from the entire company, all of whom I had somehow managed to fuck. However although having by now learned by heart the message that was universally being fired at me and being myself by now convinced of my unique capabilities, I pointed out to Alan uniqueness was no guarantee of earning a living.  This I explained to Alan at some length. Yes, I was a regular and enthusiastic practitioner of gay sex. Yes, I would not mind having sex for money to earn my living. But I had not the faintest idea of how I could set about selling my wares or who my customers might be.

My caution served only to add fuel to Alan’s enthusiasm for my future. Why exactly he was hell bent on launching me into the world of sex-for-money escaped me. But his enthusiasm for his idea – for it was entirely his idea: his project as I came to think of it – was infectious, It turned out that he had already mapped out my initial steps, which he now explained to me: “Stan, I am sure you have made the right decision – I  had, in fact, made no decision – for  to deprive the gay world of access to someone with your unique capabilities would be tantamount to sinful; throwing your talent down the drain. Look, let me explain to you how you can start, without jeopardising your present position and income, for I appreciate that you need money to live on, before you can take the risk of becoming independent.”

“Are you familiar with the Howard Hotel, which is a relatively new, small, but luxurious, privately-owned hotel located in one of those residential streets just below the Drake Hotel off North Michigan Avenue towards the lake?  The Howard, built and owned by the Howard family, attracts a certain type of well-heeled businessmen who are visiting Chicago and prefer the personal service of a small, discrete hotel to those soulless chains. The Howard is a place where such men can give way to those flights of sexual fantasy which are best indulged in well away from home. Outwardly, ostensibly upright businessmen, pillars of their local community, in whose mouths butter would not even melt, they are nevertheless, like all of us, open to and sometimes give way, to sexual temptation. If not exactly a male-male knocking shop, the Howard has gained a reputation of being discrete when it comes to the private activities of its essentially all-male clientele. The entrance floor bar has become known as the best contact point for high, social level, male-male encounters in the Chicago area. So here’s my suggestion to get you started on what I hope will be an illustrious and profitable career for you, doing something which you both like, and at which you excel. It’s a sort of suck-it-and-see approach, which, in the unlikely event of failure, will leave you still in your present job, no worse off than you are now. Stan, as I see it, it’s a win-win, risk-free situation for you.”

“All you need to do to start is to invest in a decent suit, shirt and tie and a pair of proper shoes, so that you look presentable to the sort of deep-pocketed businessman, who should be your target client. Forget the seedy sort of gay joints you and Carlo trawl together in search of recreational sex.  Your aim has to be to attract the crème de la crème of businessmen, who have the money and are willing to shell out big bucks to satisfy their sexual needs when away from home. You may be surprised to learn that inside many of those sober-looking business suits lurks a sexually unsatisfied man who is in search fulfilment; or one who likes to indulge in sexual fantasies with an anonymous third party: someone who is not part of his regular life.  It’s a case of the cat playing away whilst the love-sick mice, are left at home twiddling their thumbs. Do not underestimate the power of sex; it is a strong motivating force, which can often not be ignored by even the most sanctimonious and sober looking types. It often wins out over common sense, which is how many public figures come a cropper by having their sex-lives exposed in the media, which as you must know are utterly relentless if they even scent a juicy story.”

“So, here’s the plan; it’s basically very simple. Suitably accoutred sartorially, you go and install yourself at one end of the bar in the Howard Hotel one evening, buy yourself a drink and simply wait.  Don’t’ go on either Friday or Saturday nights, as businessmen go home for the weekend. But Sundays through Thursday are OK. I’ll bet you a dollar to a doughnut that you hook your first client within an hour or I’ll eat my hat.  Of course you have to be prepared and have the necessary paraphernalia of the profession such as condoms and lubricants on you – I suggest a small shoulder satchel to contain these key items – and a business card giving your name and credentials and contact details. as your client will almost certainly ask you for a telephone number. I recommend that you get yourself a second cell-phone just for your business use in order to keep your private life private.”

“You should view every client as a potential advertiser for your services; word-of-mouth recommendations from satisfied clients will help you develop your business.  Now one of the advantages of this approach is that you have a minimum outlay to get started and by picking up your clients in the hotel in which they are, in all probability, staying, the question of where go to consecrate the act of communion, if I may put it like that, will be solved at no expense to you.  I should tell you, by the way, that the Howard does have several top-floor rooms which it lets out on an hourly basis should the need arise. So if by chance your client is not staying at the hotel, you have an immediate solution.”

“Stan, my guess is that you will hook your first client within an hour and that he will be staying in the hotel and so you will probably go with him to his room to work your magic on him. Now, you have to be ruthlessly hard-nosed when it comes to payment; you have to insist on cash on the nail before you make any move. But my guess is that your first client will be a well-heeled dude, who, although he is unaware of the fact, is much more experienced at buying sex than you presently are in selling it. So if he agrees to your offer, he will have the cash available in green backs, which you must get him to hand over before you start. We now come, quite naturally, to the most important point: how much can you peddle your wares for?”

“Well, my friend, having had the pleasure of experiencing you twice, and having thought you were well worth the $750 outlay the first time, last night your magical second performance on my ass, both with the cane and your cock, followed by your subsequent efforts on that lusciously fuckable pair of college jocks, Dave and Zach, served to reinforce what I knew already; that you are a totally unique and outstanding cocksman. I therefore think that you should start as you mean to go on and charge a stiff fee for your services. I think that at $500 for the first hour and $250 for subsequent hours, you would be a snip. Mark my words, Stan, once you get over the initial start-up hump and word of your capabilities gets around – which it will – you will wipe the floor with the competition. Stan, at the risk of repeating myself again, you are completely and utterly unique in the way you always take your partner to the heights of sexual ecstasy, which he never dreamed was possible. Put your heart, or perhaps I should more appropriately say, push your cock, into it and you will succeed; of that I have not the slightest shadow of doubt. So go to it, young man.”

“Alan, why are you doing all this for me?  We first met in a doctor-patient relationship; but then you suddenly, by your extreme generosity, turned a professional relationship into a friendship, moreover, a friendship as intimate as any two men can have with each other. And then, as a result of what I did for you, you have sort of become my guardian angel, my mentor, my career advisor. So I ask myself: why are you doing all this for me?”

Alan laughed and said: “Because from the moment I first saw you and was subsequently able to help you professionally overcome your sexual hang-up, I liked you.  You know how it is, I am sure; you like or dislike a person on first sight; well that was the way it was for me with you.  Then when I saw what I had surgically done for you, I simply could not resist sampling the superb-looking piece meat my handiwork, I will not say had created, but had helped along; I could not resist the thought of seeing it in action, or rather experiencing it  for myself, which led me to make the offer I did. But what I had not anticipated, was that not only were you the embodiment of  Greek god,: a physically  gorgeous, sexually attractive, young stud with as superb a penis as any I had ever seen; but when you used it on me for the first time, it was a totally new experience, a revelation, for me.”

“I have had sex with many different partners over the years as I confess I have been a dedicated, practising homosexual since I was sixteen. But never in all my experience had I ever before been transported to the heights of orgasmic delight as you manage to do for me.  Your mastery of the art of anal copulation – and as you practise it, it is an art – is totally amazing; it is unlike that of any other man I have experienced; and believe me, I have had plenty of experience.  And so I was desperate that we should not lose touch when it suddenly hit me you would make a peerless male escort, which is why I have pushed you in that direction. But come what may, I sincerely hope that we continue our friendship and physical relationship.”

“Alan, I am very flattered that you think so highly of me and there is no reason at all why we cannot continue to steer the same course together indefinitely, until such time as neither of us can raise the flag anymore. But there is one thing I must make quite clear:  Carlo and I are more or less joined at the hip; we are mates for life, deeply in love with each other, and no one will ever come between us. This having been said, although Carlo and I enjoy a fantastically tight and physically satisfying relationship with each other based on the deep love we feel for each other, both of us enjoy having casual sex with other guys. So, we frequent the gay spots of Chicago together where, as a form of recreation, both of us have casual, one-time sex with other guys we do not even know. If you like, it’s more or less like going out to the cinema or a restaurant together.”  

“Now, that you have met Carlo and we have together met your own other half, Jeremy and we have all, by chance, met that stunningly attractive pair of gay, college guys, Dave and Zach, speaking for both Carlo and myself, we had sort of hoped that this might be the beginning of a close friendship among three, well-matched groups, whose six members all seem to enjoy having sex with guys other than their immediate partners. So fear not, Alan, that I shall abandon you;  for if all else fails and we do not get together for group sex as Carlo and I hope,  then I shall be happy – indeed eager – to service you independently in perpetuity, free, gratis and for nothing. The only thing to remember about our future relationship is that my devotion to Carlo is absolute. Together, we are a rock-solid item. You have almost drowned me in praising my capabilities; but let me just tell you this. You, Alan, are a hell of a good fuck. You made me sweat yesterday evening, by your superb anal sphincter control.”

I then said loftily, “Now, Alan, as you have have compared me to a Greek deity, which Carlo has also done, by the way, it behoves me to ask you, gazing down on a mere mortal like you from my lofty position on the summit of Mount Olympus where you have figuratively placed me, if you would care to have communion with me in my deified form, before I leave.  If so might I suggest that we move ourselves to your recreation room to benefit from the technical accoutrements therein, which are designed to mitigate the physical awkwardness of the positioning of the key parts of the male anatomy which are called upon to unite in such physical acts of communion as the one I am now proposing to you.”

“Jeezus H. Christ.” said Alan, roaring with laughter, “Where the hell did you get that pompous piece of claptrap from?  Translating your high-flown drivel into plain English, I take it you are asking me if I want you to fuck me again before you leave. If so, then in three short words my answer is yes, yes, and again, yes.  After all, who am I, a mere mortal, as you perceptively and acutely observe, to refuse to take communion with a Greek god. I presume that you propose to take me on a virtual trip to the summit of Mount Olympus; with your cock up my ass to ensure that you catch me in case I slip on what I suspect might be arduous climb.”

After this exchange of flippant repartee, as we both were stripping off for action in the recreation room, as Carlo had suggested I do, I took a long look at myself naked in one of several full length mirrors placed there for just such narcissistic reasons of self-admiration to which we are all prone. There is a saying: “It is difficult to see ourselves as others see us.” which is mainly said about a person’s character; but it is as applicable to a person’s physical characteristics as it is to his behaviour. I ought not to be saying this about myself as it sounds as if I am blowing my own trumpet, which I suppose I am; but in taking a good look at myself in the mirror for the first time ever, I saw myself as others see me: naked and preparing for sex. I can but say that I was mightily impressed with what I saw.

All that gym work had paid off in the form of my muscular, well-ripped physique, the likes of which few men ever achieve without the physical dedication I had lavished on my body since I was seventeen and still at school. It understandably, drives prospective sex partners green with envy, as they themselves prepare to taste that ripest of ripe fruit: my massive cock. As I stood there amazed, but also impressed at my own appearance, I watched my cock, as if aware of its key role in what was immediately to follow, exert its independence. Before my very eyes, as I divested myself of the extremely brief thong, which served as packaging for my crown jewels, it transformed itself from an attractive rubbery eight inches, descending flaccidly over my high-held balls, into a dead straight shaft of ten-plus inches of rock-hard man-meat surmounted by a large, well-rimmed head from which the first drops of cum were already anticipatively oozing. As if knowing its mission in life, it persisted in its upward journey until it held itself proudly erect at an angle of about forty-five degrees to my belly; it was, believe, me, a more formidable fuck-stick than any that I had ever seen on any other man.

I suddenly sensed that Alan was watching me admiring myself in the mirror and turned to face him. “Well you look highly self-satisfied by the image of the hunk you have just been ogling in the mirror; and so you should be; there are not many young studs who are your physical equal, especially where it counts most. But you have an edge on most young gays, many of whom if not quite so big as you, are nevertheless well equipped for sex; in contradistinction to most, you know how to use your prime asset to perfection, a gift given to very few. And although your massive cock makes you hyper-attractive to the eye of the beholder, it is knowing how to use it, which you do to perfection, which sets you in a class by yourself, way above the competition. It is that, my dear Stan, as I keep telling you, which is going to make you a fortune as a male escort. Now perhaps if you could drag your eye away from admiration of your admittedly stunning self in the mirror, you could again affirm to me by your customary, positive action, what I already know to be fact: that Stanley Przewalsky is the unparalleled king of gay sex.”

With that, Alan went and laid himself flat on his back on one of the padded tables, with his ass on the edge, indicating that he wanted me to take him in the standing mission position, addressing his anus with my cock and holding his legs over my shoulders. I have to say that I always find this to be one of the most comfortable and satisfactory positions in which to fuck ass, which, as I mentioned earlier, is never the most elegant of acts. But unless they are performing on stage, the protagonists to the act are seldom interested in how it appears, however bizarrely grotesque, but purely in satisfying their own lustful carnal desires.

For this final act of sex before we parted for the day Alan really showed his paces as the expertly qualified bottom he truly was.  After thoroughly lubricating the working parts of our joint sex engine – my cock, the piston; his anus, the cylinder – as I slid myself inside of him he snapped his anal sphincter around the shaft of my cock, gripping it firmly immediately below rim and thereafter made me made me work hard for the entire time as I fucked him in the only way I knew: my long stroke, signature manner. By his skill, he extracted for himself and gave me via my cock, the maximum, erotic sensation from every stroke I made, which due to the continued pressure exerted by his sphincters, intensified our mutual pleasure. And when that magic moment finally arrived: that exquisite climax to the act: the simultaneous orgasm, it seemed to me that on this occasion it was exceptionally intense, as our joint emissions of exceptional quantities of sperm testified.

I allowed Alan’s legs to fall, and withdrawing my still hard cock from his anus, allowed myself to sprawl face down on his still recumbent body. I then eased him further back on the table so that we both were more comfortable; and so we remained with our cocks sandwiched between us in complete silence together for some minutes. As I relaxed, more or less glued to Alan by his generous emission of sperm which, as he had neglected to use a condom, he had involuntarily discharged in great ejaculative jerks all over his own stomach and chest, I felt completely satisfied with my performance.  In fact, not to mince my words, I knew that I had just performed the greatest and, for me the most satisfying act of anal copulation of my life.  I only hoped that Alan had felt the same.

Whenever I had sex, which was pretty often, I was accustomed to that exquisite – yes, that is the exact word to describe it – sensation, which, at the moment of orgasm, courses through the body. But this time, whether it was due to Alan’s own muscular involvement rendering the act truly mutual, the climax, when it came, was, for me, and I hoped also for Alan, quite transcendental in its intensity.  I had never experienced anything remotely like it.  I knew at that moment, come what may, I would hate to lose Alan as a sex partner. Note I said sex partner and not lover, as it was not a question of switching my affections from Carlo to Alan. Carlo and I were deeply in love with each other and nothing could ever break the bond between us, But equally, as two active gays, Carlo and I both liked to have casual, recreational sex outside of our own permanent relationship.  As I lay there with Alan, I knew after what had just happened between him and me, that there was a special something between us when we fucked and that he would remain a permanent fixture in my sex-life.

Lying there together as we were, I suddenly felt Alan’s cock, which was sandwiched between us hardening.  Then before I knew what was happening, with a sudden show of strength, he flipped us both over so that I was now on my back. He then pulled himself up onto his knees, spread my legs, and knelt between them, before folding them across my body, forcing me into the egg position. Reaching for a cushion, he pushed this, with my help, under the bottom of my back, thereby giving himself unimpeded access to my anus, Realising by now that Alan was in the thrall of sexual arousal and could not longer control himself, I saw no reason to resist and I simply sat back to enjoy the ride as he fucked me.

I admit I was surprised when, without any preliminary lubrication, he thrust his hard fuck-stick deep into my hole. Luckily his generous previous emission had left his shaft slick with his own sperm, drops of which were still oozing from his cock-head; and so I was given a smooth ride.  But when I say a smooth ride, Alan had clearly surrendered all control over his rational self to his lust for a fuck and was in the throes of that imperious sex urge, which simply had to be obeyed.  So as he battered my hole relentlessly until he finally reached his own climax. I helpfully, and for my own good, I might add, held my own kit out of the way of his of a cock, which he was using like a sledge hammer on my hole. When he finally climaxed and withdrew himself from me, he threw himself onto his back at my side with his sperm flying everywhere. Although the absolute antitheses of what had occurred in our previous act of copulation, I actually enjoyed being hard fucked by Alan, even though he had not succeeded in spite of his vigour, to bring me to my own climax. Our union served only to allow Alan to satisfy his own uncontrollable sex urge; he could have been fucking anyone at that moment; but nonetheless, I found his battering of my hole with his cock, without any thought for me, quite exhilarating.

When it was all over, we lay again side by side in complete silence for about five minutes, Then Alan turned towards me and said: “Stan, I’m deeply sorry for what I did to you just now.  I don’t know what took hold of me; but I just had to fuck you; and fuck you really hard. I simply could not control my actions and I now feel horrible about the way I hammered you. What is done is done and cannot be undone; however I sincerely hope that my violent actions have not ruined our friendship forever. I can but repeat what I have told you before; you are absolutely the greatest when it comes to gay sex. No one holds a candle to you when it comes to giving a guy a truly great experience. What you gave to me just now, was just the greatest sex of my life. I have never, ever before experienced the intensity of the the orgasm which you managed to induce in me. I think it was the euphoria of the moment, which made me lose my self-control and do what I just did. If I could take it all back, I would; but I cannot and can but say how ashamed of myself I feel. I treated you like an animal just now, for which I humbly apologise.”

“Alan, there is really no need to apologise; we all lose control of our senses at some time in our lives. Just for the record, let me add that I enjoyed immensely having my hole battered by your cock. Perhaps rough sex where the top just fucks his partner for his own satisfaction is needed from time to time to make us realise that we are all human and that the need for rough sex to satisfy oneself can assail all of us and cannot always be repressed. What you did to me just now was to open a safety valve and let out some of the pressure which had been building up inside of you. If you had not vented your feelings on me, then I am sure you would have found someone else. Just for the record, I found what you did to me totally exhilarating; not at all sex as I practise it, but a refreshingly different experience. That is why Carlo and I, who are as close to each other as any two guys can ever be, go out on the town from time to time for recreational sex, which is so different from the sexual relationship we enjoy living together as an item.”

“But let me just come back to the praise you heap on me. Let me tell you that good though I may be as a top, you yourself as a bottom are absolutely sensational and deserve equal praise for the intensity of the orgasms we have enjoyed together. Obviously it is the guy who is top, who does most of the work in any sex act. But what I have learned from fucking you is that the bottom can also play a decisive role in the intensity of the joint climax which is what I always strive to achieve.  You have a unique ability to flex your anal sphincter muscles during intercourse; you grip my cock in a way that no one else, not even Carlo, ever does and make me sing harder for my supper. The result is that we both achieve an orgasm of the mind-blowing intensity, such as we have enjoyed just now.”

“You have just said that the sex we had together this evening was the greatest ever for you. Well it was the greatest ever for me too. I attribute this to the fact that as top and bottom, we both pulled our weight equally. Mutuality, my friend, I personally see as the key to great sex. So, have no fear that our friendship is at an end; indeed, quite the contrary, for I consider myself lucky to have met someone like you. You are a perfect complement to the life I lead with Carlo, and I know that he too appreciates your  qualities and hopes that he and I can have regular contact with you and Jeremy and possibly also with Dave and Zach, whose qualities and obvious dedication to the cause we also admire. So might I suggest that you and I now retire to the showers to wash away the emissions of our labour, otherwise we shall both stink to high heaven. Whilst gay sex had become something I could not live without, I ask myself why it has to have such undesirable, sticky consequences. But then without the jism, sex would probably be like alcohol-free beer: a pallid, degutted imitation of the real thing.”

Chapter 7

That evening I recounted to Carlo exactly what had happened at Alan’s and outlined his plan for my launch into the world of the male escort, as yet to me still unknown. In spite of all the praise and exhortation I had received, I confess that in my own mind I was still undecided. Having listened to me, Carlo, who from the start had been more enthusiastic about my potential new career then I myself had, said. “Alan certainly has thought the thing through. I think the idea of the Howard Hotel is great. After all what do you have to lose?” Then without asking me what I thought, treating the whole thing as a fait-accompli, he more or less steam-rollered me into doing as Alan had said, as he continued: “So on Monday, I’ll go with you to choose a suit and the necessary other items of clothing you need to complete your transformation from a scruffy-looking supermarket shelf-filler into exclusive Male escort. It’s almost like the story of Cinderella going to the ball. Now you’ve got to look really good from the word go; you have to give the impression that you are already at the top of your profession if you are to get away with the exorbitant sums with which Alan has suggested you sting your clients. So we will go to the men’s wear department of Marshall Field’s on State Street (Chicago’s biggest and most prestigious and naturally, most expensive department store, still independent in the year 2000) and get you kitted out properly,”

Carlo never even thought to ask me where I would like to buy my new clothes or even if I wanted to go ahead and chance my luck with the idea. Thinking about it later, it was probably exactly the steam-roller treatment I needed to get the thing underway. Left to myself, I would probably have dithered on endlessly and not made a decision either way.  So it was good to have a benevolent bully pushing me along.  It gave me a tremendous boost to think that Carlo – and Alan too – had more faith in me than I did in myself. Next morning I went to the bank, where I had stashed my little hoard of $4000 and withdrew $1000 dollars in cash as I had no a credit card or check-book and together, Carlo and I went to Marshall Field’s.

Coming from the social background that I did and in my present, out- of-public-view job, I had never needed a suit in my life. I doubt whether Carlo himself had ever himself possessed a suit either, but with that typical Germanic efficiency in his genes, he organised both the sales clerk and me, and in no time at all I was in the fitting room trying on various garments. Like a mother equipping her boy for school, Carlo fussed over me before finally pronouncing himself satisfied when he saw me in a lightweight, navy-blue suit. My participation in the the affair, consisted of shelling out an exorbitant – to me anyway – $400 for the suit. But Carlo was not yet finished as he gently bulldozed me into buying four pure cotton shirts and two silk ties, together with a number of sexy thongs of some, over-priced, prestigious brand of underwear that I had never heard of, which as he put it, would add shape to my kit and control my bulge! “You need to make the most of our bulge even when you are wearing your suit; it’s what I think of as come hither feature,” he added sagely.

But I began to regret that I had told Carlo more or less word for word what Alan had said to me, as when we left Marshall Field’s store, he was clearly not done as he went on: “Well, now we need to get you a shoulder-bag to keep your supplies in, a new mobile phone and some visiting cards. Oh, I don’t think you can offer your services under your own name, Stanley or even Stan; neither of them sound up-market or sexy enough. So thinking about things as I have been, I wonder what you think about calling yourself Alex, professionally. And before I forget, one thing which Alan evidently did not mention to you, we need to get you kitted out with some large size condoms and lubes; and as you are to style yourself as a full service type of escort, so you must be prepared, I think you should also get yourself a flexible punishment belt which you can stow in your satchel in case your first client wants you to flog him before having sex.”

As I listened to this torrent of all-encompassing, verbal onslaught, I thought to myself that there are times, Carlo, when you can be an absolute prick and this, my friend, is one of them; and I mentally told him to fuck off. But then I realised he was just doing what he thought was best for me, his life’s partner, as he desperately wanted me to succeed. So why deny him his moment of pleasure helping me to set myself up for my attempt to forge a new career for myself? And then I asked myself how I would feel if things were reversed; if Carlo, not me, were preparing himself to become a male escort, with all that that implied for our close partnership. I wondered how I would feel if Carlo went off every day to earn his living by having sex with other men and then came home to share a bed with me, his life’s partner. It made me think and frankly, I am not sure I could have worn it.

I thought back to the time when Carlo went off in search of casual sex leaving me behind as I was too embarrassed to go with him.  I had been insanely jealous. So I stopped begrudging him his moment of pleasure and allowed myself to become putty in his hands, as we went from shop to shop, buying the items necessary for my launch. I even stopped resenting the fact that that he had chosen my new name, Alex, for me, as I found it very attractive and it would become the name by which I was known to everyone: business contacts and friends alike.

But there was still one thing which Carlo insisted upon before he pronounced me ready to make my first public appearance.  He suddenly insisted on my visiting a barber; but a very special barber, who not only cut my somewhat unruly hair and made me look positively civilised, but who also shaved away my pubic hair and all the hair on my upper inner thighs towards my anus. By the time he had finished with me, I guess you could say that the approach to my fuck-hole was as soft as a baby’s bottom; at least that is what Carlo told me it felt like as he fucked me that evening. 

I have to admit that losing my pubic hair, certainly made my kit lusciously presentable. And looking at myself in the bathroom mirror I felt proud of what I saw. As you might already have guessed Carlo, with typical German efficiency, insisted on me dressing myself completely in my new outfit: cock thong, suit, shirt and tie, shoes and socks, before giving me his final seal of approval on my appearance. “I wouldn’t want you to go off half-cock,” he said, fussing around me like a mother seeing off her favourite son on his first day at a new school. I thanked God that he had sent me a guardian angel in the form of Carlo to watch over me: someone would sympathetically share my misery if I failed.

Anyway, the time for hesitation was now past; the die was cast and a date chosen for my – I almost said debut, which implies performance and I was certainly not yet there – tentative attempt to become a male escort.  I finally bit the bullet and, dressed in my new finery, went one fated Monday evening for the very first time to Howard Hotel that fatidic venue of gay sex at its highest and most expensive level. Carlo had wanted to come with me to lend me his moral support, but I firmly kiboshed that idea as I could see that as the beginning of the end; I felt that I should now sink or swim on my own. Carlo would just have to wait to share either my euphoria or despair until after the maiden deed had been cone successfully or had failed miserably. Whether I had either sold my services for the first time for hard cash or come away with a limp piece of man-meat between my legs, I knew Carlo would still be there for me.

I can tell you that I was on the edge of my nerves, verging on a nervous wreck, ready to turn tail and call it a day before it had even begun, as I walked, for the first time into the luxurious surroundings of the Howard Hotel.  If you have ever wondered what a fish feels like when it is pulled out of the water, well I can tell you, as that is exactly how I felt at that moment. The whole place simply stank of wealth, the likes of which I had never before encountered. The entrance floor bar, which Alan had designated as the place for my tentative launch, was buzzing with the activity of the pre-dinner crowd; but a quick scan of the faces told me the whole story; there was not a single female present.  Alan had been right about the Howard being a hotbed of homosexuality; so at least I had come to the right place to sell myself.  The bar itself was extremely long; and following Alan’s instructions, I slid my butt onto a stool at one end.  Apart from one guy at the other end, I was alone at the bar as the crowd had coalesced into discrete groups, who had chosen to chew the fat at the numerous small tables available.

An extremely handsome barman of clear Latin American origin, Antonio from the name plate on his immaculate white jacket, came up and asked me what I would like to drink. I ordered a beer, which he put before me.  Antonio was about my age and just looking at him, I could feel my cock stirring, as he was certainly a very attractive and desirably sexy looking young man. It is a fact that we gay men – well, speaking for myself at least – have a sort of inbuilt reflex in that we automatically assess every young guy we meet as a potential sex partner; and Antonio, who was an utterly gorgeous hunk of prime, male flesh, certainly pushed all my buttons. Had we met one evening in one of Chicago’s gay joints, I would have moved heaven and earth to ensure that I stretched his sphincters for him.  But this was neither the time nor the place for such thoughts of casual sex; and Antonio was certainly not the type of guy who would have $500 handy to shell out to give himself the pleasure of experiencing my ten inches up his ass.

He was obviously immediately curious about me as he began “This your first visit to the Howard, sir? I don’t recollect seeing you here previously. You here on business or pleasure sir?” Direct questions requiring direct answers.  So I replied: “You are quite right; this is the first time I have been in the Howard; and I am very much a business man,” I quite purposely said that I was a business man rather  that I was in Chicago on business to see if he would pick on the difference I had intended to make. Knowing the reputation of the Howard as a hot-spot for what I thought of as up-market, genteel sex, I had already sensed from his curiosity that he was possibly a go-between: a facilitator of contacts. I watched him for his reaction as he digested what I had just said.

Antonio as was a sharp as a tack as, with a knowing smile which said it all, he gave me an answer of discretionary ambivalence: “I see, sir. Let me just say, sir, that like all staff at the Howard, if I can be of any assistance to you, it will be my pleasure.” And with that I watched him saunter off down to the other end of the bar, where he engaged in conversation with the only other man propping up the bar at that moment, leaving  me to enjoy my beer together with a tab for an astonishing – for me, at least – $25!  I watched them as they glanced down the bar are at me. Then Antonio made his way back to me and said: “Sir, the gentleman at the other end of the bar is one of our regular customers when he is in town. He wonders if you and he have met somewhere before sir, and I think he would quite like to renew your acquaintance.”

“Antonio, it is very kind of you to act as unpaid messenger, but I don’t think that I have ever met your other customer before. However, as in my line of business I meet many men – I purposely said men as opposed to people – why don’t you give him one of my business cards, which will confirm that he has mistaken me for someone else; an understandable mistake in the soft lighting of this bar.”

I mentally thanked my lucky stars that  I had had someone as assiduous as Carlo behind me to prepare me for this moment;  left to my on devices I would have put off the printing of my business  cards to some indeterminate future date. But Carlo had insisted that every minute detail of the very last item of my accoutrements be in place before he ever would have allowed me to set foot in the Howard Hotel. Carlo had, of course added his flourish to my card, which he had insisted on having expensively engraved – you know, the sort of up-market printing method which allows you actually to feel  the letters as if you were reading Braille, as you run your finger over the print – which  now read:

Alex
Full Service Male escort
Stimulation and Discipline 
Telephone  xxxxxxxx

Antonio looked at the card and gave me that knowing look which said it all; he had known from the minute he first saw me exactly my line of business and precisely why I was there. But ever the diplomat, he said; “Thank you, sir, I will pass this to the other gentleman and I am sure that when he sees it, it will clear up any confusion in his mind about knowing you,”

I was on tenterhooks as I watched Antonio return to the other end of the bar and hand my card to the man, who was potentially to be my first catch of what I had myself come to view as a fishing expedition.  But, doubting Thomas that I always am, it suddenly occurred to me that the man at the other end of the bar might quite genuinely have mistaken me for someone he thought he knew and the whole house of cards would come tumbling down.  Then I had the reassuring afterthought that had he thought he had recognised me, he would probably have approached me directly to renew our acquaintance: the most normal thing in the world to allow two guys alone at a bar to strike up a conversation. And so I sat there on a knife edge whilst I watched Antonio talking to the man, I wondered if I was ever going to hook my first fish and then, having hooked it, whether I would be able to gaff it.

The conversation between Antonio and the man I had already come to think of as my first client, ended and Antonio resumed his shuttle diplomacy and came back along the bar to me: “That gentleman has now realised that he was mistaken about having met you.”  As I heard these words, it was as if Antonio had thrust a knife into my heart; I had lost my first potential client. But before the disappointment I felt could manifest itself on my face, Antonio continued: “However, having read your card and understood the sort of business you are in, he is interested in retaining your services this very evening and as asked me to ascertain your terms, sir and transmit them to him.”

I could hardly believe my ears that Antonio, in his role of diplomatic arch-go-between, was basically asking me how much I charged for my services. I know I should have been elated, but my first feeling was one of panic. Alan had told me that he thought that I was worth the $750 he had paid me for my services and that I could ask $500 for the first hour then $250 per hour for each subsequent hour.  But there was a world of difference between the way that Alan had voluntarily suggested that he wave his professional fees, against which, as a quid pro quo, I would fuck him, and the situation I now faced. Now it was for me, the putative purveyor of the sexual services, to name my price. I had only Alan’s bald statement that I was worth the $750 he had paid me; and as a new entrant into the Chicago world of gay sex for money, I had no idea what the going rate was or even if there was such a thing as a going rate!

The sums of $500 for the first hour and $250 per hour thereafter seemed to me deliriously high, But now that push had finally come to shove, I was completely on my own and had to make some decision or I could potentially lose my first client. But if I pitched my demands too high I could possibly price myself out of the market before even ever having entered it. At that moment I felt I was between a rock and hard place. Having not the slightest idea of my own, I finally decided to follow Alan’s advice; after all he was the one who had pushed me into the situation in which I now found myself and he had been right about the Howard Hotel bar being a really hot, upper-class, pick-up venue for men in search of gay sex. So I thought to myself, “What the hell; I might as well be hanged for a sheep as a lamb.”  So, throwing caution to the winds, I burned my bridges as I penned what to my mind were my outrageous demands on the back of another of my cards.

I watched with bated breath as Antonio ferried my message to my potential client, whom I saw write something on yet another card, hand it to Antonio, who dutifully brought it to me. As he handed it to me, he said: “You’re in luck sir; that gentleman has accepted your offer sir, and may I personally wish you every success.”  I read the message which said said. “Fees OK; room 812 in half-an-hour.” Antonio, having read the message himself, added helpfully: “That’s room 12 on the eighth floor sir. Turn to your right as you exit the elevator and room 12 is on the left, sir.” Feeling somewhat on Antonio’s debt, I said: “Antonio thanks for everything; I owe you one.” He replied: “That’s quite alright sir; it’s all part of the service.  Now sir, as you have a half hour to wait, before your appointment, may I serve you another beer?”  I accepted his offer; but although I had just hooked my first fish for a fee of $500, an enormous sum of money to me, the thought of shelling out another $25 for another bottle of beer cut me to the quick.

Chapter 8

Sitting at the bar, toying with my second beer, was the worst thing which could have happened to me, as the half hour wait before I went  hopefully to gaff the fish I had just caught, allowed my innermost fear to surge to the surface. What if I couldn’t get it up when I was alone with my very first client? Having presented him with a card saying I was full service male escort, I would look a meretricious fool if my dick, which had already stirred at the first sight of Antonio, refused to play ball; I would be mortified and die of embarrassment. Moreover, as the guy, whoever he was, had my business card, if it got around that Alex had failed to raise the flag, then it could be the end of my career before it had even started.  And for the full half hour, the prospect of my cock refusing to play ball and other nightmarish scenarios assailed my head.

As you might well imagine, it was with a somewhat hesitant tread that I finally arrived before the door of room 812. With my heart racing and my nerves completely on edge, I finally plucked up sufficient courage to ring the bell. At that precise moment, I felt like naughty school boy standing outside the principal’s office, waiting to be invited in to have my arse paddled. The door opened and I got my first close view of the man who, unbeknown to him, was about to become my very first paying client.  I had only seen him at the other end of the bar and as yet we had not exchanged a single word, thanks to Antonio’s efficient shuttle-diplomacy. My first reaction as we sized each other up was one of relief as my client was an attractive young man not much above the age of thirty and looked extremely fit. “Hi Alex,” he said, as he opened the door, “Come right in. My name is Mike.” I entered the room without saying anything; but I needn’t have worried as Mike – if that was, in fact, his name – was clearly more accustomed to such meetings than I was.

He asked me to sit down and offered me a drink and then himself sat down in an armchair opposite me and said: “Well, Alex, before we get down to the business, which has brought just us together, let me just tell you a few things about myself to that we don’t get off on the wrong foot with each other. Look, Alex, I don’t mean to insult you, but I prefer straight talking; I guess from the trade you are in, selling sex to other men, that you yourself are gay. The reason I bring this up is because your client tonight is not and I though it only fair to you that you were being paid to have sex with a straight guy.”  Mike then began a longwinded explanation of why he, a professed happily married man with children wanted to have sex with another man whilst he was away from home on a business trip. It was a highly imaginative story, many versions of which, I was to hear in future under similar circumstances when my client of the moment wanted to impress upon me, a homosexual, that the guy with whom I was about to have sex, was straight.

“You see, Alex, it’s like this; when I was at college, I kind of got into the habit with my fraternity mates, of going to no-holds barred, male  parties at which we all had sex with whomever and however we wanted,  If you like, it was just a festival of buggery as most of us were not gay; but then you are young yourself; so I  guess I don’t have to tell you how young men can get when they have had a beer or two.  Well, in my case, I sort of acquired the taste for having my ass buggered by other guys: a taste which I have, for my sins never shaken off. So I still, from time to time, hanker after having my ass reamed out, a service, which, with the best will in the world, a wife cannot give to her husband. So as I travel quite a lot on business, I profit from being away from home to indulge myself in what superficially looks like gay sex with another man.”

“Anyway, Alex, when I saw you, an attractive young stud (a very revealing phrase, I thought, as I listened to him attempting to convince me that the was not himself gay, as if I cared one way or the other) alone in the bar, which as you must know does have a certain reputation, obviously looking for a pick-p, I did not know whether you were just trawling for pleasure or hoping to pull a trick. However when I consulted the omniscient Antonio, he told me that you were a businessman; and now, a half hour later, here we are, about to do business together. So why don’t we get the somewhat sordid part of this encounter out of the way for a start so that we can relax together and enjoy ourselves. Look, Alex, your fee is totally reasonable, (really, I thought to myself; you must be rolling in it, to shell out $500 for a fuck!) so why don’t you pick up the five $100 greenbacks over on the bedside table and then you can get down to addressing my needs and I can put you through your paces and see if you are really worth the money.”

So I did has requested and stashed the $500 into my shoulder bag, whilst Mike went off into the bathroom to return a few moments later stark naked.  The sight of him stopped me dead in my tracks for a few seconds; I saw that my first ever client, was a superbly muscular young man, beautifully ripped and with a good-sized piece of man-meat of his own, already on an upward trajectory from between his legs. Mike had a physique which was obviously the product of regular visits to some gym somewhere and was visually so totally attractive that under other circumstances I would have been delighted to have sex with him, free, gratis and for nothing.  But by good luck, for my maiden client, the wheel of fortune had presented me with a superb young man, who seemed happy to pay me $500 to have sex with him. Any fears that I had had that my own cock might refuse to rise to the occasion had vanished into thin air at the sight of this magnificent specimen of male manhood, waiting eagerly, as his own arousal showed, to be fucked.

Not wishing to disappoint him, I quickly stripped down to the buff to show Mike that he was not alone in having a well-ripped body and that when it came to what really mattered, he had not bought a pick in a poke. His eyes almost popped out of his head at the sight of my massive ten inch long erection, culminating in my superb cockhead from which the first drops of precum were already oozing. “My  god,” he said, “You, Alex, are really something else; you are utterly gorgeous, in a different  class to the normal sort of guy, who earns his bread at male escorting, Where the hell did you get that stupendous fuck stick from?” Then echoing Carlo exactly, he said: “You know, Alex, your dick rivals the Washington Monument.” Then, if you can believe it, this guy, who claimed to be straight and had just told me that he wanted a dose of anal stimulation as a reminder of his college fraternity days, dropped onto his knees in front of me, took my massive cockhead into his mouth and started to suck me off.

“Well,” I thought, “He who pays the piper calls the tune; so if this is what you want, then who am I to object?” So  I went ahead and helped him in his task and face fucked him, Mike’s voracious and professional devouring of my dick left no doubt in my mind that he was a consummate and regular practitioner of gay oral sex, as with my help he eagerly tried to take my entire boner down his throat. It is hard to say which of us enjoyed this initial contact the more. I had my first climax of the evening with my cock still in his mouth and I jerked my orgasmic delivery partly down his throat, before withdrawing my cock from his mouth and deposing the rest of my generous emission over his face. I could not help feeling, that it was I, in my paid role of male escort, who had reaped the greatest benefit from this initial scene – surely the whole point of sex – and not my client. But as he seemed satisfied with what had happened so far, who was I to rock the boat?

“Alex, that was absolutely fantastic; mind-bendingly awesome, the best oral sex I have ever had in my life. And I speak as a man of considerable experience. Alex, yours is the biggest and best cock I have ever sucked-off in my life.” Gone now was any pretence of being a straight guy in search of a little anal stimulation  when away from home to remind him of his college days. He might well have a wife and two kids but he was now revealing himself as dedicated practitioner of gay sex: someone who was intent on having an evening of intense sex whilst away from home, an indulgence for which he had the means and for which he was prepared to pay.  Having now whetted his appetite, there was obviously no stopping him as he said: “So come on, Alex, I can barely wait to feel your magnificent phallus up my arse. So jump to it young man, I want you to give my anus absolute hell as you rough fuck me.”

Of course, rough fucking was the absolute antithesis of my own, completely natural, approach to anal sex; but how did I explain this to a client, who was paying me to please him and wanted a rough fuck? The whole idea of my attempting break into the world of male escorting was predicated on my belief in the importance of mutuality in the sex act, coupled with my apparently rare, copulative ability to take both my partner and myself through to intense orgasms simultaneously with no manual assistance. Initially sceptical my own apparent unique ability, first commented on by Carlo and then by Alan, and subsequently  confirmed by many others with whom I had had casual sex, my entire plan to establish myself as a male escort was based on this  difference, which would set me apart from the crowd.

“Mike, I would like a chance to show you what I consider to be the unique side of my capabilities which sets me apart from the general run of male escorts.”  Of course, here I was ad-libbing as I had no real idea of what male escorts actually did, other than have some sort of sex with their clients or whether they too were capable of exactly what I considered to be my unique qualities; qualities which I had have been brain-washed by my supporters into believing gave me a unique magic touch. For all I knew, there could be many others out there who were just as good as I was. But in a tone of voice which implied a confidence which I did not feel, I soldiered on: “However, if I am proven to be wrong then, I will happily give you a repeat performance and rough fuck you as you wish. So may I begin?”

Mike looked quizzically at me and said. “Well it is said that a change is as good as a rest; so go ahead and work your magic on me and show me something I have never before experienced; but just remember you are dealing with a very experienced man, who will hold you to your promise if you fail to impress him.  I only hope that you will have the stamina to give me a repeat performance if you fail, I am sure I do not need to remind you that as an experienced top that the act of  fucking is fucking, hard work and takes a lot out of a guy,”

So far so good; so I asked Mike what his favourite position for anal sex was.  To my utter joy, he said he preferred to be taken flat on his back in the mission position.  He went over to the bed, lay down on his back, bent his knees and placed his feet on the mattress and spread his legs to expose his fundamental orifice and then waited for my move. I inserted a cushion under the base of his back to give me a better angle of attack to his anus, which I then copiously lubricated.  I handed him a condom and suggested he roll it on to his penis, which was still hard, to catch his emission, I rolled a rubber onto my own ten inch erection and carefully lubricated myself.  “For crying out loud,” he said, “What the hell are you fiddling around with; for fuck’s sake get on with it?”

“Mike,” I replied, “I have my own technique when I fuck ass; two things I learned early on in my career, were firstly the importance of thorough lubrication and secondly, to make haste slowly. So, if you will be patient and allow me to proceed, I will endeavour to give you an experience which I doubt that you ever even imagined possible in your wildest dreams.” “Well, after all this messing around, it had better be good.” To which, I replied quite simply, hoping that I would pull it off: “Rest assured, Mike; it will be.” 

But as I said that, I prayed that I would not  mess things up  and would be able to make good on my promise and take him – well, in fact, both of us – to the heights of erotic pleasure which is simultaneous orgasm induced purely by copulation totally free of any manual assistance by either partner. I was certain he had no idea of what I was aiming to do. As I slid my rock-hard ten inches into  Mike’s rectum and felt him grip my cock as it bottomed, a feeling of immense satisfaction  coursed through my body  as I realised that I had just taken my maiden step toward becoming a fully-fledged escort; I was at that very moment being paid – and royally so – to fuck my first client. That thought reinforced my resolve to make a success of my first – well let’s call a spade a spade – fuck for money.

As I progressed in my normal manner, making haste slowly, giving Mike the benefit of the very long strokes made possible only by the exceptional length of my penis, slowly increasing them in both force and speed, I knew from his moans of pleasure that I was succeeding. But finally, as the moans turned into the magic words: don’t stop, please don’t stop now, and I knew that I was succeeding, I myself became also totally consumed by the peremptory demands of the sex act, which, reaching its climax, defies any control whatsoever, I knew that in the next few moments I would take both of us over the edge, to the unbelievable delights of that most erotic and desirable of sexual experiences, the male orgasm. And as that unbelievably intense moment approached, I withdrew, as I always did, my full length from my partner, held it in the air for a couple of minutes before plunging it back in one smooth movement, with well-nigh cataclysmic force  into the anus it had left just moments ago.

In this, the most critically important sex act in my life, I prayed that I had not misjudged the moment no return, to my mind absolutely essential to complete the mutuality of the act, but in most casual gay sexual encounters usually absent, As I deposited my load into the condom I was wearing on my cock, which was still embedded deep inside of Mike, I felt the wave of the most intense orgasm I had ever experienced flood through my body, And as he too was wracked by the juddering paroxysms which accompany the climax, I knew that I had succeeded in my efforts to bring both of us to that sine qua non of mutuality: that indispensable but indescribable feeling that two men can ever experience together: the simultaneous, male, sexual orgasm. I pulled Mike’s legs flat on the bed and fell on his is body; and in that position, face to face, I held him in my arms as he ejaculated his generous load into the condom he was wearing in a series of energetic jerks. Then, after our joint climax, we remained embraced together like two lovers, each enjoying the aftermath of contentment at what we had both just experienced.

In this, my first sex act in my new role as male escort, I somehow felt I should feel guilty at deriving so much pleasure myself from an act which for which I was being paid. But there was no escaping the fact that what I had achieved was probably the longest and most intense orgasm I myself had ever experienced. I knew from the almost violent, spasmodic reaction of his body as he discharged his generous emission that he too had experienced a long and intense orgasm and I earnestly hoped that he, as a bottom, had enjoyed our joint act of copulation as much as I myself had.   I was aware as prime mover in the act, that I alone was responsible for the climax, but the aim was to please the client and that although I had thoroughly enjoyed fucking him, my own enjoyment had to take second place to his, as to be a successful male escort, I knew that I had to subsume my own desires into those of the client; it was he and he alone, who had to emerge from the encounter totally satisfied.

Any fears I had as to my failure to achieve this goal, were brushed aside by my first ever client, as he said: “Alex that was just the greatest sex experience of my life.  I have never, ever before been taken right through to my climax –and what a climax it was – entirely by the skill of my partner, without some manual assistance from me. But what you just did for me, was to treat me as if you were having sex with a woman. Women, who, as you may or may not know, but speaking as a married man with a sexually demanding wife, believe me, I do, rely entirely on their lovers to fulfil their own sexual desires. And you managed to fulfil my own need for occasional anal intercourse, to perfection.  You are an absolute crack at your chosen profession. Now according to your tariff, a second hour would cost me another $250; right? Well I would like to retain you for another hour for a repeat performance.  So, how about it? Are you up for it?”

I could hardly believe my ears at the lavish praise he was heaping on me and I have to say that his proposition for a second round was very tempting and I felt, as he provocatively had put it, I was certainly physically up for it.  But caution prevailed; this was my first professional assignment and so I decided that discretion being the better part of valour, I would quit whilst I was ahead. So I made an excuse, inventing another appointment: “Mike, flattered as I am by your desire to continue, which would give me the greatest pleasure, I regret to say that in a half an hour I have another appointment. So on this occasion I am unable to accept your generous offer, much as I would like to; perhaps we can take a rain check for another occasion?”

And that is how we parted. I left feeling rather elated at the success of my first step towards becoming a male escort. Any misgivings I had had about becoming a member of a profession, which basically sold sex, had by now totally vanished. I had thoroughly enjoyed what I had done with Mike and any fears I had had about my becoming a male escort might ruin my relationship with Carlo had retreated. I had seen that with Mike, my attitude to what I was doing was completely different to how I felt when I had sex with Carlo. Carlo and I made love to each other; but with Mike, my very first client, it was, for me, purely business from the word go. Not that I had short changed him physically, but mentally, for me anyway, it was totally different. After only one experience of selling my sexual ability for money, I already was confident knew that I could separate my personal sex life with Carlo from my new activity as a male escort. However attractive my client, I knew now with certainty that with whomever I had sex as a male escort to earn my living, could and would never replace Carlo in my life.

Chapter 9

So it was with a much lighter step than I had just a few hours ago entered the place, now with a sense of mission accomplished, that I prepared to to leave the Howard Hotel. As I crossed the lobby and made for the door, I saw that the barman, Antonio, now dressed in his street clothes, was also about to leave the hotel. Seeing me, he said; “Well sir, I hope that your business with Mr. Saunders went well.”  So there I now had the name of my first client: a guy named Mike Saunders.  I guessed that Antonio had finished his shift for the day and was now off duty as he had shed his barman’s uniform and, like me, was about to leave the hotel. We stood there an instant looking at each other before I replied; “Yes, Antonio; thanks for asking; mainly to your  organisational skill,  things went very well indeed; in fact they could not have gone better.”

Now Antonio, who was clearly a street-wise young man, had seen my card and was well aware of the type of business I had been transacting in room 812. As I was answering him, we both found ourselves looking into the eyes of the other, and I suppose we each transmitted the same message to the other.  It must have been obvious to both of us from the way we were eyeing each other that neither of us wanted this chance meeting to end there. As we hit the street, Antonio took the initiative and said: “Look, sir, I’m just going to get myself a bite to eat at the pizza joint in the next block;  I don’t suppose, sir, that you would care to join me, would you?”

So there you had it: Antonio was as keen as I myself to prolong our chance meeting and from the way he made his suggestion, with his eyes focused on my crotch, his ultimate objective was loud and clear. Well, sexually attracted to the guy as I had been from the moment I had first seen him a few hours earlier behind the hotel bar, this seemed like an opportunity sent from heaven: a chance to have some relaxing recreational sex with a gorgeous young stud and pay him back in kind for the effort he had expended on my behalf.  I had said that I owed him one; so why not use this unexpected invitation he had given me into an entrée into his private life, to discharge this rather ephemeral debt right away?  At least that is what I told myself as I said I would be delighted to break bread with him.  But I knew in my innermost self that I was using his invitation as an excuse, as I had wanted to have sex with him from the moment I first set eyes on him, before he had embarked on his shuttle diplomacy between Saunders, my first client, and me.

Over pizza and more modestly priced beer, any inhibitions Antonio might have had towards me in the hotel, where he was an employee and I a valued guest, were rapidly brushed aside as we both knew where we were heading. Antonio, like me, was the product of a mixed marriage: a Latino father, whom he did not know, as he had abandoned his American wife soon after his son’s birth and had never been seen again. So Antonio, in spite of his stunningly handsome Latino looks, which he had clearly inherited from his father, turned out to be an all American boy, who spoke no Spanish: and was as much a product of mid-western culture as I myself was. As the meal progressed and we became completely relaxed with each other, I quickly divined that Antonio was as dedicated a gay as I myself was. So when he suggested that we back to his place which was nearby and said: “So that we can relax and get to know one another better.” I had difficulty in stopping myself from laughing out loud at this cliché of a phrase.

Anyhow, back to his place we went. Antonio lived alone in a rented a furnished efficiency, one-room apartment with cooking facilities and a separate bathroom. The process of getting to know each other was accomplished in record time as we fell into a clinch as soon as the door was closed.  I pulled Antonio’s shirt over his head and divested myself of my own upper garments; then without saying a word, we both stripped ourselves naked and stood, admiring each other. Just allow me to say that there was a lot for both of us to admire;  Antonio naked was even more sexually desirable than he had been when I first saw him in his natty barman’s outfit, which had been enough at first sight to make my cock, always a reliable indicator, perk up in expectation. He had an exquisitely proportioned, muscular body of which he was both obviously acutely aware and of which he obviously took great care. Although his meat was not as large as mine, – but then, whom did I know who sported my length and girth? – he had a visually very attractive cock which had been neatly cut, unlike many men of Latin extraction.

But Antonio, having feasted his eyes on my body, glued his eyes firmly on my cock, which had obligingly risen to the occasion and was indicating its intention by pointing its ten rigid inches directly at him, the clear object of its immediate desires. He said: “Alex, I knew from your bulge when I first saw you across the bar that you were well equipped where it counts, but I have never seen such a attractively massive piece of man-meat as you are now pointing at me, So as you seem ready, why don’t we allow your cock and my hole to get acquainted as I see the potential for a match made in heaven. Alex, since the moment we first in the bar, I have been hoping against hope that we would meet again and find some way of having sex together. Call me superstitious if you wish, but I do sort of believe in fate and I think that is fate which brought us together in the hotel lobby just now. So as we have the hots on for each other at the moment, let’s waste no more time staring at each other and get down to the action.”

Antonio went and knelt on the bed; and then with his head on a pillow and his buttocks held high in the air, he spread his legs in an inviting manner opening his cleft and giving me the first site of my target: his tightly puckered anus. It was clear from the enthusiastic way in which he had readied himself for our communion as bottom, with no prior discussion as to who was to do what to whom, that his immediate objective was to take my full ten-inch piece of meat, which felt to me to be almost bursting at the seams with the intense pressure of my extreme arousal, brought on by the sight of Antonio’s superb nakedness. As I looked at Antonio’s beautiful and gorgeously inviting ass, I knew that would fuck him with the same care and attention as I had done my first client. However, there was an important difference, in that with Antonio, copulation would be a pure pleasure, not performed under the pressure to impress him with my potential as a male escort; but I had every intention of taking him and myself to the indescribable erotic heights of the simultaneous orgasm.

I could barely restrain myself from the strident demands of my cock, which with its usual impatience was urging me to thrust myself forthwith into the awaiting hole and give its owner a hell of a hard battering. But as ever, as I recalled and, more importantly, obeyed   Carlo’s dictum on proper lubrication before any action and making haste slowly, On this occasion, with the delights of one of the most attractive asses I had ever seen, willingly and impatiently waiting to be fucked, I can tell you that it required all my self control to restrain myself from my worst instincts, going ahead, as I knew I would enjoy doing, and rough fucking Antonio. 

Thinking such thoughts brought home to me that I was, at the end of the day, a human being:  a man, who, like all others, was subject to the same imperious carnal desires for sex. There was one part of me which would happily have gone ahead and fucked the hell out of Antonio, without any thought for him; and, quite frankly, I am sure that he would have seen that as quite normal. What set me apart from the crowd were the importance I attached to the mutuality of the sex act – of every sex act – and the fact that I had the physical endowment to allow me to achieve my aim. It was at that moment I realised that Carlo, Alan and the others were right: I was different and did have something special which I brought to the act of gay sex.

As I was applying the lubricant to Antonio’s anus, I asked him whether he would like me to take him bare-back or whether he would prefer me to use us a condom. As I had hoped, he opted for bare-back, as there is nothing for either the top or the bottom to the act that compares with sensation of that first intimate contact achieved by the naked, stiffly erect penis of the top sliding smoothly into the rectum of the bottom.  I am sure Antonio wanted to experience live – skin to skin – what for him was very probably the biggest cock he had ever taken up his ass. However, he was surprised when I suggested that he himself roll on a condom and that he refrain from the usual practice of working his own cock manually leaving everything to me: “Trust me, Antonio,” I said as I prepared to shaft him, “And I will take you to places which you never even knew existed.” 

As I slid my rock-hard, ten inches deep inside of the vital part of the gorgeous Antonio, he let out a moan of contentment as I bottomed my cock in his hole, whilst I myself had the tremendous satisfaction of penetrating a welcoming hole, whose owner was still probably expecting nothing more than a good hard fuck from a large cock. There was no need for me to prove myself to Antonio, whom I could have gone on and rough fucked for my own pleasure; but as a matter of course I knew that whomever I was fucking, whether as now for pleasure, or as a male escort for business, I would do no other than treat everyone equally, with that sense of mutuality which was to become my password.

But especially now with Antonio, I wanted to give him the greatest sexual experience of his life and transport him to heights of orgasmic intensity which he had never even dreamed existed, let alone experienced, Antonio had pushed himself out on a limb for me, way beyond the call of duty, as they say in the military as they pin a medal on your tit. Thanks to his efforts he had helped me hook my first ever client, which without his help, I doubt I would have achieved on my own. So when I had said I owed him one, I really did mean it.  And now that I was in process of of making good on my promise, I intended to pull out all the stops and make it an experience that he would long remember. Of course, altruistic though this sounds, it was altruism tempered with more than a touch of self interest. I would have been the first to admit that I had wanted to fuck Antonio on first sight, as he handed me that ludicrously overpriced beer. So although I intended to give him of my very best, I knew that I was about to enjoy myself as much as he was.

There is a saying that the sex act, between two people, whether male-male or male-female, is a toy which never fails to please; and for the guy who is the top, no truer word was ever spoken. But often, as I had experienced first-hand – or perhaps better put: first-arse – myself when I had bottomed for some unknown guy on one of my forays with Carlo into the Chicago gay scene, I was frequently left high-and-dry, so to speak. So it had readily become my philosophy that whenever I was the top, I would always ensure that my bottom partner was fully satisfied by the act which I was controlling. This is exactly what I now intended to do for Antonio: to take him with me to a place he had never before known existed, let alone visited.

As I pumped his anus with my signature, habitual, long powerful strokes of my cock, I soon heard those magically encouraging words repeated over and over again: “Don’t stop now; please, don’t stop.” So intent on giving Antonio the greatest orgasm he had ever had in his life, I increased the power and length of my strokes until we both exploded together. As I pumped my own sperm into Antonio’s rectum, he simultaneously, with convulsive paroxysms of delight, experienced what was obviously an orgasm of a magnitude of which he had never before even dreamed. I knew that I had succeeded in my objective of giving him the fuck of his life, as his body shook with uncontrollable jerks as he pumped out his own spunk, filling the condom he was wearing almost to bursting point.

I rolled Antonio over and in the post-copulative face-to-face clinch, in which we clung to each other for a full five minutes following our joint climax, Antonio and I each planted endless kisses on our mouths and all over our faces, in the joint euphoria of what we had just done together. Then as he slid his cock, slippery with his own cum, gently into my anus, I knew that I had gained another disciple in Antonio, to whom I had shown what I was coming to think of as the true light. As Antonio gently fucked me, I realised that I wanted him and me to become regular communicants.

 By the time we finally parted, I had told Antonio the whole story: how he, reading my business card and assuming that I was a fully operational male escort as the card proclaimed me to be, had, quite unknowingly, helped me land my first paying client. “So Antonio,” I said, “You have unwittingly played a very important part in launching my new career, which is why, when we parted company and I went off to peddle  my wares to Mike Saunders, I told you I owed you one. Without your help, Antonio, I would never have clinched that contact, which I have every hope was the very first step towards a new career that will free me from the shackles of the dead-end job in a supermarket where I presently worked to earn my daily bread.  So I hope, my friend, that what I was able do for you just now, you found an adequate reward for the services you rendered me. But let me just add, Antonio, that making good on what I had originally seen as something I owed you, in the event turned out to be an utter pleasure for me and I only hope that it was the same for you; so much so that I hope we might remain friends and make a regular habit of it. Antonio, my friend, you are one hell of a good fuck as a bottom and you’re not at all bad at being a top yourself!”

Antonio listened unbelievingly to what I was telling him, and finally said: “So you are not a fully-paid-up male escort as it says on your card? Listen Alex, I’m very much a loner at the moment, and so needing regular sex as I do, I play the field several times a week in my spare time, including having sex with some of the hotel’s clients. You don’t need me to state the obvious that the Howard, if not precisely an up-market, gay knocking-shop, is a top level contact point for visiting businessmen in search of gay sex. But that is probably why you were there in the first place; hoping to turn a trick: your first, if I have heard you right.”

“Well, just tell you something, which I am sure you probably know, as I am not the first guy you have ever fucked. You, Alex, are unique. I have lost count of the number of different guys with whom I have had sex over the past couple of years, but never have I had an experience even vaguely to compare with the one you just gave me. My god, Alex, don’t you realise what you do for your partner is unique? Well at least what you did for me just now was. You took me to places which I did not even know existed until you fucked me. Alex, you raise sex to such unimagined heights; at least unimagined hitherto by me. What you gave me was almost a religious experience, at the end of which you showed me the true light and induced in me and orgasm of such intensity as I never before knew existed. You, Alex, are an utter phenomenon. If you did to that guy Saunders what you did for me just now, then you will be a great success. Look,  Saunders is a regular visitor; but he is not only one who uses the bar to sniff out a partner for the evening; nor are you the first guy for whom I have acted as a go-between in organising an assignation. So if you leave me a few of your cards, I will see if I can spread the gospel further. And I can do it with a easy heart, for in me, Alex, you have a true believer.”

Chapter 10

That night, in bed with Carlo, I told him everything that had happened, including my post-business interlude with Antonio. Thankfully, he did not seem very concerned that I had had casual sex with Antonio.  As Carlo slid himself into me, I figuratively sighed with relief that I had such a faithful, trusting and competent lover. Carlo gently proceeded to take me through to orgasm and I can tell you that having sex with him was just so reassuringly comforting that it transcended anything I had just lived through with Mike Saunders and Antonio. I thanked a god, in whom I really did not believe, that Carlo and I had found each other and that come what may, we would always be there for each other.

But next morning, in the cold light of day, I suddenly realised that with $500 in my pocket and successful though my first attempt to sell myself as a male escort had been, one swallow did  not make a summer and that I needed to plough on with the task of selling myself: but how? That was the question I posed myself, to which I had no immediate answer. Male escorts, unlike female prostitutes, do not stand around on street corners in doubtful but well-known neighbourhoods, peddling their services. So how did I get myself known? Should I use the bar at the Howard Hotel as a base and hope that I could hook another visiting businessman looking to satisfy his sexual needs? Thinking about things I saw that  if I was to be successful, even having something which no other male escort had, which I had by now even managed to convince myself  was true, I needed to get my name known and potential clients had to be contacting me rather than me going fishing for them.

Sure, the occasional successful, spur of the moment, paying pick-up at places like the Howard was OK; but, short term if I was ever to be able to quit my supermarket job and devote my efforts to working fulltime as a male escort, I had to get my name known. Potential clients had to be contacting me, soliciting my services, and not the other way around. I had to have a realistic chance of having a regular supply of clients if I was ever to be able to quit my present job and make a go of being a male escort.

It was the following day, whilst at work in the supermarket, contemplating this apparently intractable problem that my new portable phone rang, thankfully during my morning break. “Am I speaking to Alex,” an unknown voice began. Confirming that he had the right number and that he was indeed speaking to Alex, the voice  continued: “Well, hi Alex;, we don’t know each other, but a mutual friend (a mutual friend???) or  perhaps I should better say, a mutual business acquaintance, gave me your card and spoke very highly of the services you recently rendered him. I imagine you know the person and services I am referring to?” How could I not? I had only had one client, Mike Saunders; so it had to be he who had passed my card to owner of the unknown voice.

I confirmed that I knew to whom he was referring and to the nature of the services I had rendered. I detected a sense of a relief in the voice that we had got over that delicate, introductory, verbal ballad and could now talk turkey and get down to the nitty-gritty of what he actually wanted from me. “Our mutual acquaintance told me that what you did for him was totally exceptional in its intensity: something he had never experienced before. So to get down to business, which is why I am calling you, I would like to retain your services for a session of anal stimulation.”  I heaved a figurative, silent sigh of relief that the guy, whoever he was, had finally had the courage to acknowledged verbally that he was seeking sex. “But,” he continued, “I see from your card that you also offer discipline.  So I would also like to retain your services to cane my ass before we have sex together. I take it that would not pose any difficulties for you. So if you would care to come to my offices down- town, at about 5:30 pm today we could see how we get on for first time together.  Your fees of $750 for both services are completely acceptable.  So can I take it that you will be there?”

So here I had my second client; hook, line and sinker; but his demands pin-pointed the inadequacy of my preparation.  I had no cane; not that that was an insuperable problem.  But I could hardly walk into an office block in down-town Chicago, wielding a cane in my hand. Additionally I needed time to change into my posh suit; as a top male escort, which I purported to be, I could not turn up in my supermarket, shelf-filling attire of T-shirt and jeans and sneakers. I had to think quickly to avoid losing my second client ever and to get myself out of an awkward situation. So I said: “I am afraid I have another prior engagement at 5:30 pm today and will not be free until about seven o’clock this evening. Also as you wish me to cane you prior to anal stimulation, I only administer CP to a client on his premises with a strap, which I can carry discreetly in my shoulder bag. I am sure you will appreciate that I cannot walk down that street and into your offices brandishing a punishment cane in my hand. So if you insist on the cane, I suggest we make another appointment and that you come to my place, where I have all the necessary implements of CP to hand and I can meet your every erotic wish.”

My plan was to put him off for a day or so, to give me time to make alternative arrangements. It had suddenly become blindingly obvious to me that I needed my own place where I could receive clients in private.  “Well seven o’clock would also be OK by me. And as for the problem with the cane; well you don’t need to worry about that as I keep one in my office.”  I could hardly believe my ears at what he had just said.  The gods must have been with me that day as what was meant to be was obviously meant to be. So I left work in a jubilant mood, went back the apartment to find that Carlo had not yet returned from his job at the gym. So I took a shower, lubricated my hole, just in case the guy wanted to fuck me and put on my finery ready to present myself to my second client ever. I left a note for Carlo saying: “I am working late; see you later.”  I signed it Alex rather than Stan, as an indication of what I was doing.

He had given me his name and the name and address of the company where he worked. “Ring the bell at the front door, and the night-doorman will let you in as I will tell him that I am expecting you, so you will have no difficulty in gaining entry to the building out of business hours. Then take the elevator to the top floor and I will meet you there and show you to my office where we can conduct our business totally undisturbed.” So at precisely seven o’clock that evening, with that inevitable feeling of trepidation, I rang the bell at my client’s office bock and was admitted by a liveried doorman. I confess that I was very nervous as the elevator whisked me up to the top floor, where as the doors opened, I had first sight of my client for the evening.

To my great relief, Steven J. Still turned out to be a fit looking, youngish man; at first sight too young to be the Finance Director of a major corporation, which is what the name-plate on his door proclaimed him to be. Steve, as he told me to call him, had a palatial office suite, which was my first intimation of how the very rich lived or at least of how they were treated by their employer.  Like my first client, Steve was a married man, evidently with two young sons, as three, framed photos prominently displayed on a credenza behind his desk led one to believe. 

As he saw me looking at them, he obviously felt the need to justify himself: “Yes, you might be surprised to see that I am a married man with a lovely wife, with whom I have a great sex-life and who has given me two great boys.  But my wife knows about my weaknesses, which were acquired at college, before I met her and she tolerates my occasional dalliances with other men, as she has accepted the fact that the man she fell in love with is the way he is:  a man, who from time to time, likes to have his backside thrashed and take another man’s cock up his ass. It’s a habit I acquired as a member of my fraternity at Harvard and, quite frankly, one I have found impossible to break. So as I do not wish to resort to visiting Chicago’s gay spots, I resort to professional guys like you to satisfy my occasional urge for anal sex.  I have to tell you, Alex, that you come to me tonight, highly recommended by someone, who has raved about your exceptional capabilities. So unless you have any questions to have doubts about having sex with a married man, I suggest we get straight down to business.”

Steve was clearly a man who believed in plain speaking and telling things exactly as they were. Taking my silence as positive, he then said: “Let’s get the sordid question of cash out of the way and then we can settle down to an evening of pleasure, which I hope both of us will find enjoyable.”  He opened a drawer of his desk and handed me a wad of $100 notes. There’s $800 there, as I didn’t have any fifties to hand; but it’s OK as |I can afford and am quite prepare to pay for my rather perverse sexual pleasures.

We then moved into a side room, equipped with what looked like an adjustable massage table with a padded leather top. Off this room, I could see a bathroom through an open door. Steve immediately began to strip off and indicated to me to do likewise. Finally, completely naked we stood looking each other over, making our preliminary assessment. Steve in the buff, turned to be an attractive well-muscled figure with a good-sized piece of man-meat between his legs, which I was nevertheless relieved to see in no way equalled my own. I noticed immediately that this penis had been been pierced and that he was wearing a Prince Albert cock-ring. This, together with the adjustable massage table seemed to indicate that there was possibly more to his extra-marital, gay, sexual liaisons than he had said; to me Steve was already coming over to me as being a secretive swinger.

His look was focused on my cock, which, true to form, had already started on its upward journey, dismissing my earlier fear that when the critical moment for action arrived, I might not be able to get it up. “Christ, Alex, you are really big where it matters most. I have never seen such an attractive looking cock in all my life; and believe, me I’ve seen plenty.” Given that he was coming over to me as now what I suspected to be a dedicated, active, bi-sexual man, I found his assertion quite believable, especially as I knew, false modesty aside, that few men were physically even my equal.

To my surprise, he quite suddenly dropped to his knees in front of me and said: “With your permission,” before immediately taking my tumescent meat in his mouth and beginning to suck me off. As he greedily sucked my penis to its fully erect state, I saw that he was thoroughly enjoying himself, but I had no idea what usually transpired in such engagements between a male escort and his client. So I played it by ear and as he was paying me royally for my services and oral sex was sex, I decided that the least I could do was to help him: and so I very gently started to fuck his face. I found his efforts on my cock highly stimulating and I admit I was enjoying myself at least as much as he was. He turned out to be very proficient at oral sex: a real pro, in fact;  so much so that had he continued much longer, he, the client, would have taken me, the putative supplier of sexual services, to orgasm and I would have shot my load either down his throat or all over his face.

But as suddenly as it had begun, it equally suddenly ended. He suddenly pulled his mouth away from my cock, which he had just seconds earlier been in the process of devouring, looked up at me with what I can but describe as hungry eyes and said: “Quick, over there, in the cupboard; go and fetch the cane as I need you to beat my ass right now.” Ask me not why he had the sudden urgency to be chastised. Suffice it to say that by the time I had retrieved the cane, he was already bent across the table offering me his ass for punishment. Since that first time I ever handled the cane and applied it reluctantly at his request to Alan Greenberg’s ass, my attitude towards wielding the cane had undergone a damascene conversion. Whereas that first time I had hated doing what Alan had requested me to do, in the interim, having beaten him a second time and then gone on to beat both Dave and Zach, I had discovered that I had myself a hitherto hidden sadistic side to my character and that I really derived great pleasure from thrashing another man’s naked ass.

So as I looked at Steve’s expectant buttocks, I felt a surge of pleasure run through my body at the thought of what I was about to do. Steve evidently took corporal punishment seriously; the cane he now was holding was a professionally made punishment implement as it had a shaped handle at one end to allow the wielder a firm grip. It was just over three feet long. Made of rattan, it combined solidity with flexibility and I sensed that it would deliver stinging cuts to the buttocks I was about to beat.

“What I want you to do,” said Steve, “Is to begin by giving me six parallel cuts, evenly spaced, from the bottom of my back to the top of my legs and then to give me six more cuts diagonally: three from the right crossed by three from the left. I want you to space all twelve cuts so that my entire butt has been covered; And do not hold back as I want you to apply the cane with maximum force; don’t worry if you break the skin and produce some drops of blood as I really do want to feel the extreme pain which only a caning can deliver, which is why I have dropped the traditional paddle in its favour.”

“Rather you than me” I thought to myself as I viewed his ass, “But it’s your call as you’re paying; so if that’s what you want, then who am I to argue?” As I viewed his eagerly expectant buttocks, I saw that they still bore traces of another previous beating, which I suppose he had enjoyed. “There is no accounting for taste.” I thought, as he spread his legs opening his cleft and giving me first sight of his tight anal pucker, to which I would later also be giving my earnest attention. I was feeling quite elated what I was about to do, as the close relationship between anal sex and corporal punishment hit me starkly, square between the eyes for the first time at that precise moment. Almost intoxicated by the fleeting moment of power I was about to exercise, I felt like a despot about to wreak vengeance on some disobedient underling. To my eternal shame, I admitted to myself that it was a feeling which I much enjoyed as I prepared to beat my client’s ass. I knew I was going to enjoy inflicting pain on another man and was being paid to do so! 

It was a dark side of my character which I had not hitherto recognised was lurking there, just waiting to be revealed. But there was no getting away from the fact that now that I had recognised it was there, I could not simply wish away; it was just something I would have to live with. Somewhat jumping the gun in this story, as I had not yet taken the leap into my tentative new profession, my embracing of corporal punishment as a service, which in spite of my misgivings I truly enjoyed, was to stand me in good stead, as I quickly became known not only for my unique copulative ability, but also for the way in which I dispensed severe discipline to those of my clients who requested it. However, it was in those final words: to those who requested it, that I eased my ever present conscience and found my mental salvation from my worst instincts. I only ever beat on request and never indulged my basest instincts in seeking to promote my abilities with the cane, which I know I would have have thoroughly enjoyed as a regular preface to sex.

But now faced with Steve stretched naked in front of me, eager for me to beat his ass, I found myself so sexually aroused by the eroticism of the moment, that I thought for a moment that before I had delivered my first cut with the cane, I would climax and shoot my load all over his expectant ass.   Standing there naked as I was, my own cock fully erect, dripping precum like a leaking tap, was literally urging me to sink myself into the waiting anus, which was irresistibly attractive to me at that moment. Carlo’s wise words about anal sex: Make haste slowly, echoed in my ears. And as I prepared myself to to apply the first cut of the cane; they seemed totally apposite to the aroused situation, in which I found myself, (“Carlo, what would I do without thee and thy wisdom?”). Fortunately, I managed to control myself completely; and getting a grip on my sexual urges which would have led me to make a fool of myself had I impulsively shafted Steve, I delivered my maiden stroke, calmly, precisely and with the great force as requested by my recumbent client. I was learning fast that to be a success at my future profession I had to subsume my natural urges to the wishes of my client.

As I delivered stroke after swingeing stroke, I accustomed myself to the crack of the cane landing with gunshot clarity on muscular flesh, I shuddered inwardly as I saw each time a deep, red weal develop almost instantaneously; some immediately oozing drops of blood where I had broken the skin. I asked myself how Steve could stand what I was doing to him; but in the role of hired help, mine was not reason why but to do his bidding. After that first, centrally placed cut, stroke, I landed the next two higher towards the bottom of his back and then went to town with four parallel cuts to his lower buttocks towards the crease. After I had completed the beating with the six, crossed, diagonal strokes, I stood back and looked with appalled admiration, a contradiction in words if ever there was one, which nevertheless conveys my equivocal feelings about what I had just done. His entire backside was criss-crossed with the deep red welts of the cane, already turning blue with the bruising of the flesh beneath the broken skin.

As the full horror of what I had done to his backside hit me, had he decided to call it a  day after that, I would gladly have given him part of his money back. But Steve was made of sterner stuff as he hauled himself up from the table and said:  “Well, Alex, I think we can say that you passed that test (Test? Had I been tested?) with flying colours. I can think of no recent beating which I have enjoyed so much.” “It takes all sorts to make a world,” I thought: “Rather you than me.” He went on: “So I suggest we get down to your core ability and you show me what you can do with that magnificent piece of meat between your legs, which I see from the way it is pointing at me, is raring to go. Our mutual friend tells me that you are an absolutely sensational cocksman”

Steve certainly knew what he wanted as he went back to the table he had just left; but this time he lay down on his back with his knees bent and bare feet on the edge of the table. “I hope you will find this position suitable,” he said: “For me it is the one which I prefer when I am having my ass fucked.”  He then went on and showed he was used to giving orders and having his own way, which I suppose explained to some extent the key position he held in the company for one so young: “So what I want you to do is to adjust the table to a height which suits you so that my ass is easily accessible to your cock. Then you can pull me forward so that my anus is more or less on the edge of the table, and can hold my legs over your shoulders and fuck me in comfort. I find that with me in this position, with my partner of the moment holding me firmly in place, allows him to give me a really hard fuck, which is exactly what I like.”

Steve certainly knew what he wanted, and was not afraid to call a spade a spade. Listening to him give me instructions in such graphically specific detail, I was momentarily dumbstruck. I saw from his remarks that he was accustomed to paying someone to indulge his sexual needs and was probably more conversant with the practices of male escorts than I was. However, as he had contacted me on the sole recommendation of my first client, who had waxed lyrical about the sensual aspects of my approach to anal sex, I felt it would be stupid to deprive him of an experience, after which many different guys had by now waxed lyrical to me. So I decided to ignore Steve’s wishes for a rough fuck, which had been issued in an imperious sort of voice implying that they were an order rather than a request and plough my own furrow.

I rolled on a condom and dosed my cannon liberally with lubricant, before giving Steve my full length in one smooth, powerful, uninterrupted thrust. He had wanted a rough fuck, so I had no hesitation at all in dispensing with any foreplay and simply thrust my rock-hard fuck-stick quite brutally up to the hilt in his anus.  Now I do not claim to have the biggest cock in the world, as I am sure that there are many guys who can outdo me. But I  knew from what was now my accumulated sexual experience, which had grown to be really quite extensive  in view of the sorties Carlo and I had made in search of casual, recreational sex, that both he and I, and I in particular, were better endowed than any of the guys with whom we had had sex. So I doubted that Steve, experienced though he evidently was, had ever before taken such a massively hard piece of meat of such exceptional length and girth so suddenly up his arse. But that was my only concession to his request for a rough fuck: a rapier-like, forceful penetration of his anus, almost as if I was taking him against his will.

His first verbal reaction to my attack on his fundamental orifice was an almost blasphemous oath of the pleasure he had obviously felt: “Jesus H. Christ. Alex, what you just did to me was mind-bending. I have not been taken anyone up my arse like that since my first sexual experience ever, when I was raped aged seventeen by the school PE instructor. That guy was really something. He was the one who got me hooked on CP before sex; in fact it was when he had paddled on my naked butt for some infraction I had committed in the showers that he he went on and gave me my first experience of anal sex, after which he and I sort of came together for the rest of my time at school. So when I went onto college, with a year and half’s regular sex under my belt, I was already fully experienced sexually and I had an absolute ball in my frat house – a sort of sexual paradise – for my three years.”

All this and more he told me as I was standing there in the ludicrous position, with his legs over my shoulders and my erect penis deeply embedded in his rectum. Anyone listening to him about his sex life in his student years could have been forgiven for thinking he was a dedicated, died-in-the-wool homosexual.  I wondered, as I now prepared to fuck him in earnest, how, where and when a woman, his wife, had come onto the scene, as he claimed to be happily married with two kids.

I had decided that I had to be true to my principles as I started to fuck him: so I began in my usual manner, in the words of Carlo, by making haste slowly, as I delivered my long, powerful, unhurried strokes, each of almost the full length of my cock, building up both in force and speed as I endeavoured to take both of us to the ultimate goal of the simultaneous orgasm. As I began my thrusting, Steve, for whom such long strokes were a new experience, made possible only by the length of my endowment, immediately began working his cock with his hand, as he clearly had no concept of allowing the whole act to be controlled only by the guy who was top.  And he was quite right in acting the way he was proposing to do; for as I had seen numerous times, both top and bottom partners to the anal sex act, always finished up violently masturbating themselves to their climaxes.

So his surprise was completely normal when I said to him: “Steve, if you please, I would prefer you not to attempt to jerk yourself off and leave everything to me. If you could just ensure that you hold your junk well clear of my thrusting, which is going to become quite violent, as I would hate to think that I had crushed your balls by accident. So just relax and leave it all to me and I will attempt to take you to places where you have never been before: places you never even knew existed.”

By the time I had taken Steve to the brink of orgasm, I had him metaphorically, by the balls, as he panted repeated those oft heard exhortations:  “Don’t stop: don’t stop now: please don’t stop.”  When I finally pushed both us over the edge and we both climaxed simultaneously, as he was not using a condom, he jerked his unbelievably copious wad all over his own torso and my chest and belly. We clung to one another in that paroxysm of utter pleasure, which only a sexual orgasm ever engenders in a man. For my part, even though I had physically worked hard to bring Steve to a climax, the like of which I am practically sure he had never before experience, I somehow had a guilty feeling that I should not be paid to perform a job, which had given me as much pleasure as it had to my partner. It was a feeling which I have never, ever been able to shake off in my career as a male escort every time I perform what even I, the ultimate doubting Thomas, have been forced to recognise as my magic.

When we had finally both recovered from the physical exertion followed by that immediate sense of fatigue which the rigours of the act of copulation always seem to impose on both parties, Steve bestowed the most profuse praise on me for what he saw as my unique ability. “Alex, I have to tell you I have had sex with many men, but you truly are something else: an utter phenomenon. I have never, ever before, been fucked the way you did just now; nor have I ever been taken to the heights of such an intense orgasm as you managed to give me; and without any manual help from me,”  But what he said next, took me completely by surprise. “Look, Alex, I told you earlier that I needed CP and anal sex from time to time. So, in view of your outstanding capabilities on both fronts, I would like to retain your services on a regular two week basis, under the same financial arrangements as today.  So, if you are agreeable could we pencil in pour diaries that you will come here each alternative Friday night at six to attend to my needs?”

“If I was agreeable?” He had to be kidding!  Of course I was. What he was offering me was equivalent an open ended contract which would bring me $1500 a month. He had no idea that he was giving me, an absolute beginner in the profession of which he thought I was a long established member, the assurance to allow me to take the risk and quit my job at the supermarket to devote my entire time to developing my career as a male escort. Looking at myself, figuratively in the mirror, I finally bluntly recognised the fact that I was embarking on a life of professional male prostitution. I marvelled that there were men who were prepared to lay out what to me were huge sums of money for sexual services. But at that moment I was still somewhat naïve, as I had not yet grasped the fact that the sort of man I was aiming for, the likes of Steve and Mike, were earning – or if not actually earning, were receiving – enormous salaries and bonuses.

Chapter 11

After leaving Steve I went home to Carlo to tell him of my luck. He welcomed me with open arms and gave me a celebratory shafting, which confirmed what I already knew: the best sex I ever had was with him, whether as top or bottom.  When we fucked, as we often did, we were always on the same wave length; if ever two guys were meant to be together, it was Carlo and I.

The next day at work, I rang Alan Greenberg, and arranged to see him after work in his Lake Point Tower apartment.  I felt I owed it to him, as the prime motivator and originator of the situation, in which I now found myself, to give him a progress report on my activities to date. But I also wanted his input into what he thought should be my next steps. However, before Alan and I met that evening, I had two unexpected calls from guys staying at the Howard Hotel, both of whom wanted to engage my services for the following evening.  Being a glutton for sexual excess and not wishing to turn either man down, I arranged to service both of them the following evening: one from six to eight and the other from nine to eleven.  Fate seemed to favour me as both guys wanted me to see them at the Howard and neither wanted CP. I finished work at the supermarket at five and so I had an hour before my first appointment at six to make myself presentable.

My contact with Antonio, who was handing out my cards to likely potential customers at the bar, was evidently paying off and I wondered how much gilding of the lily Antonio had indulged in to get such rapid results.  Of course, he could speak with authority on the subject, having had firsthand experience with the guy he was recommending.  So again I found myself in his debt, for which I hoped shortly to be able to reimburse him in kind; I did not want him to think that I thought of him as a sort of pimp. But I also wanted to see Antonio as a friend; not only was he a really likeable guy, but he was also one hell of a good fuck. I also wanted Carlo to meet him as I saw him as an adjunct to the group of friends with whom both Carlo and I were sexually compatible and with whom I hoped we could establish an ongoing sexual relationship.

We had both enjoyed the evening we had at Alan’s place and I hoped we could look forward to more free and easy sex evenings together with Alan and Jeremy, and Dave and Zach. I saw Antonio as becoming a member of that group, whose members would meet on a regular basis for an evening of relaxation and recreational sex. It seemed to me that it beat hands-down trawling the gay clubs of Chicago for casual sex. But such sexual frivolities were cream on the cake for future, as my first priority had to be to get my nascent male escort business, if you could call it that, up and running on and on an even keel.

Anyway to get back to the point, I related to Alan my progress to date. He seemed not at all surprised by my immediate apparent success as he said: “I told you that you were a dead cert. as as a male escort and I am absolutely delighted that your first experiences have been so positive. Frankly, Stan, (or should I now start calling you Alex?) I never doubted for a moment that you would have any difficulty in getting started given your unique qualifications. Not to put too fine a point on it, your clients should feel it is a privilege to be fucked by you; I can tell you for a fact that both Jeremy and I do. So now that you have got started, what are your immediate plans?”

“Well, I do seem to have made a good start. I have an open ended verbal contact with Mike, which is good for $1500 per month and I have two new clients tomorrow at the Howard Hotel, who are each good for $750, a sum I consider exorbitant, but the clients seem willing to pay, so why should I object? So I have kind of thought that I have to formalise things …” But at that moment, before I could go on to explain if not my plan – I really did not have one – then my thinking, my business phone rang and so I answered it in front of Alan, who, smilingly, waved me on. To my utter amazement it was a yet another guy, this time recommended by Steve, who wanted to engage my services; again, to my great relief, he wanted an evening appointment and at his downtown office. As far as I could tell it was just for sex with no mention of CP. But whatever the services I would be required to provide, it was my fifth client within my first week and I was not yet truly in business.  

I told Alan that I had just hooked another client, my fifth within a week: “Alan, I am where I am now thanks to your advice; I cast my line in the bar at the Howard Hotel, where I have got to know the barman, a terrific guy called Antonio, whom I want you to meet sometime. Anyway, it was Antonio, who helped me hook my first client; since then he has gone on to recommend me to two other hotel guests, both of whom I am scheduled to service tomorrow evening at the Howard. And Steve, my first client, outside the Howard, came to me by word-of-mouth via Mike, the guy whom I had just serviced at the Howard. Now the call I have just received is from a guy who has got my name via Steve and wants me to service him on Friday evening in his office down town, making five clients in my first week.”

“So far luck has been with me. Three of my clients have been out-of-town businessmen visiting Chicago and staying at the Howard and so I will have serviced all of them in their rooms, while I will have serviced both Chicago residents in their offices downtown. Also I have been able, so far, to arrange all five appointments in the evenings, so that my private activities do not interfere with my job at the supermarket. How long this lucky streak will last is anybody’s guess, but it will come to an end. So I have come to the conclusion that if I am to go on, even dabbling in the business as I am, with one foot in one camp and the other in another, I need a place of my own. The guy, Steve, whom I serviced in his office downtown, provided me with his own cane as he wanted CP before I actually fucked him.  So as you can see, Alan, I am in a bit of a dilemma to know what to do for the best. One thing only is clear to me. For some reason fate has smiled on me and has given me a period of grace which will certainly not last forever.”

Alan listened to all this intently before he spoke: “Stan, let me first ask you this: are you enjoying being Alex rather than Stan? If the answer to that question is yes, which I expect it might be, then think of  what you have achieved in your first week of selling your body for sex; and make no mistake, Stan, that is exactly what you are doing  in your evenings at the moment. You have managed to get yourself five clients, which gives you an income for your first week’s work of $3750; and to top it all, you have got one client called Steve, who is so enamoured of your services that he has retained you to do the same for him – note I said for him and not to him – twice a month. So you have advance orders for your services which guarantee you a minimum income of $1500 a month.”

“So Stan, I fail to see why you are, as you put it, in a bit of a dilemma when your future is staring you in the face. Doubting Thomas of your unique capabilities though you have been, I would have thought given your additional experience in the meantime and the accolades which have been poured on you by your various partners,  that even you should by now be convinced  of what was evident to me after the very first time that we had sex together. You have a copulative ability which is just so unique that it sends those of us, who have been privileged to experience it, into paroxysms of pleasure of such intensity, which we have never before even dreamed was possible, let alone tactually experience. Speaking as a confirmed atheist, I can therefore say with some authority that you, Stan, are God’s gift to gay sex.”

“You Stan, moonlighting your role as Alex, the experienced male escort, have pulled of the coup of the century, which not even I, the eternal optimist would have thought possible. Look at what you have achieved in a single week: five clients, one of whom is really hooked on you. So make no mistake, it is not as Stan, the filler of supermarket shelves but as Alex, the male escort extraordinaire, where your future lies. I agree with you that you need to get place of your own where you can receive clients and have available all the panoply of implements of corporal punishment known to man – and believe me, there are plenty of them – so that you can satisfy the most bizarre sexual desires of your clients’ however perverted of whom, I am glad to say, there are plenty of them around.  But instead of  attempting to hang on to your job at the supermarket and sell sex on the side, which is what you are actually doing,  my view is that  you should bite the bullet, quit your job and devote our whole time to developing a new career doing something you really enjoy.”

“If you do not seize the opportunity now, when the iron could not be any hotter and have the courage to take the risk, which in my view is minimal, the chance may pass you by.  So my advice is to burn your boats, quit the supermarket job and attempt to make a go of your new career as Alex the Male Escort.  There is a risk, I agree, but if you fail, which I think is very unlikely, as top quality sex both sells and pays well and you really do hold a winning hand, you can always go back to some sort of humdrum job to keep the wolves from the door.”

“Now on the question of a place to call your own, where you can set up shop and receive your clients, I may be able to help you. You see, in my youth, to escape from the claws of my parents, both of whom disapproved and for the matter, still disapprove of my sexual orientation, aged then just eighteen, I used a legacy which my grandmother had left me when she died, and bought an apartment with a roof terrace on the top floor of a new condominium development in a street not far from the Howard Hotel, which is how I came to hear about its reputation as a hotbed for gay sexual contacts.  Well for several years, I used this place as a sex bolthole;  but now I have my very successful practice here in this huge apartment in Lake Point Tower  and am comfortably shacked up with Jeremy, who, incidentally, is as dear to me as Carlo evidently is to you, the place has not been used for several years now.  So Alex, to call you by the name I expect to see on the doorbell when I visit you there,  I am happy for you to use the place at a minimal rent to help you get started on your new career. You can pay me the rent whenever you feel able to. So I hope you will feel able to accept this offer as I really want you to be successful having been the first person to suggest the idea to you.”

I was overwhelmed by Alan’s generosity and even more so when he took me to see the place he was offering me. The apartment consisted of a large living room which was furnished in more or less the same style as Alan’s recreation room at Lake Point Tower to facilitate the comfortable enjoyment of gay sex; and on one wall was hanging a selection of canes and other implements of corporal punishment, testifying silently to Alan’s early devotion to this particularly painful perversion. Off this room were a spacious kitchen and a large bedroom, equipped with the largest king-sized bed I had ever seen and off the bedroom was a bathroom with – yes you’ve guessed it – a   a huge three-man walk-in shower, echoing in its own silent way the purposes for which the large bed was used. But this was not all, for the roof terrace which was completely private and not overlooked had also been furnished with an eye to comfortable al-fresco gay sex; and to add to the sheer comfort of the place there was also an outdoor shower.  I could barely believe my eyes that this was the so called bolthole, which Alan was offering me at a very low rent to get me started on my career as a male escort; it exceeded, by far, even my wildest expectations.

“So do you think that this little pad will do to get you up and running? You can pay me the rent whenever you feel able, or you could, if you wish pay me in kind.”

“Alan, if you think for a moment that I would dream of having sex with you in lieu of paying you the rent for this place, after all that you have done for me, you must be wrong in your head. There is no way that I would ever take a cent off you for sex. You have become my friend to whom I owe practically everything. You paid me $750 in wavering your fees for you surgical skill, which has made me what I am today. So there is absolutely no way that I could ever again have sex with you other than as a friend. So when I can, you will get the rent of this place and any sex we have together will be as friends and not a landlord and tenant.”

Alan came across to me with a troubled look on his face: “Alex, please forgive me if I have offended you. I don’t know what in heaven possessed me to make such a stupid and crass suggestion; I must have been out of my mind to even think of such a thing.  But now that we are here, and there is a double bed invitingly waiting in the  next room, could we not agree to seal the deal in a way which  would be highly agreeable to both of us, so that we can dispense with the formalities of a written agreement and take each other on trust?”

How could I refuse my chief promoter?  Frankly there was not much incentive to do so, other than my pride that I would stoop so low; and anyway he had made an abject apology. So I swallowed what was my fast disappearing pride, for Alan was a hell of a good fuck and what better way to cement our agreement. Of all the guys I have ever had sex with, Alan comes over hands down as the best bottom I have ever experienced and that includes my partner and lover Carlo. Just as I have come to accept that I am endowed with a technique given to few, so also does Alan, when it comes to furnishing a harbour for a seriously searching, large, rock-hard cock such as mine. Alan has control of his anal sphincters like no one else I have ever fucked. Alan grips his partner’s cock with his anal muscles which makes his partner work hard. He is intent on extracting the last ounce of pleasure from each and every thrust of his partner and makes him work hard on every stroke. Not for Alan the quick, sloppy fuck of the porno videos. So he and I, as sex partners, are ideally suited, as his controlled style of bottoming suits exactly my own unhurried style of thrusting as a top, as I endeavour to take every partner through to orgasm, preferably simultaneous with my own.

But sex tonight had to be made very special as it was to seal a bargain between us of which I was the main beneficiary. Why Alan should have adopted the role of my guardian angel which he had done on the strength of our first fuck together, I shall never know. But it was not a onetime gesture, as he now was offering me the use of this magnificent apartment at a derisory rent to help me establish myself as a serious male escort. But now that we were going to seal the deal in an act of sexual intercourse, which I suppose was appropriate in view of my future activities, I was determined that this time must be very special for him. 

As we stripped of for action I suddenly realised that we were surrounded by mirrors, in which we could each see ourselves in all our naked glory. And frankly not to be boastful, naked glory aptly describes what we both saw; the mirrors revealed to each of us, ourselves as others, had they been present, would have seen us. With no false modesty or boastfulness, what was revealed were two magnificently muscular young studs,  in the peak physical condition of young manhood, each sporting a rock-hard cock,  of which Alan’s was already dripping with precum in anticipation of the union which was about to follow.  Any slight I had felt from Alan’s suggestion that I might pay for the rent of the apartment in kind had already vanished as I was a keen as he was to get down to the act of anal copulation itself.

Alan was not short of sexual attributes himself, but when he looked at my ten inch rod with unconcealed eagerness, he said: “Alex, for that, for me, is your name from now on,  I know of no-one who looks so attractive naked as you do or who has such marvellous equipment. You really are the absolute tops, you know; no one holds a candle to you when it comes to knowing how to please your partner and I am quite sure you will be a great success in your new career. So now that we are we are ready to seal our contract, might I suggest that we forget the preliminaries and get down to the task of consummating our agreement?”

With that final remark, any hope I might have been entertaining that Alan would exercise his truly remarkable oral powers on my dick prior to intercourse proper, vanished. I can but describe his eagerness by the somewhat bizarre analogy, that he was like a dog, scenting a bitch on heat, straining at the leash to fulfil its natural function. Of course, the analogy is false, in that Alan was the bitch wanting me, in the role of the dog, to shaft him. But it was obvious looking at his cock, which was dripping precum at an ever increasing rate, that he was besotted by the desire for me to fuck him as soon as possible. I don’t want to give you the idea that this was a one-sided affair and that I was being railroaded into having sex with Alan, for that was certainly not the case. Indeed I was greatly looking forward to our union as Alan was a great fuck: a superb bottom partner It was just that I was in better control of my sexual urges at that moment

 So I said: “Alan, it is a very warm evening, so might we move our proposed activity onto the terrace as I have never, ever had sex al fresco and this is such a special occasion –especially for me?”  Alan immediately opened the door leading to the roof terrace and went and lay down on his  back on the outdoor bed, which was there for exactly the purpose  it was now about to be used.  Fortunately, I had brought my shoulder bag of supplies with me and I was able to lubricate his anus and my own cock before penetrated him.  By common accord we both dispensed with the use of condoms on this unique occasion. Alan summed it all up as he said: “I want the ink of your sexual signature to linger in my body as long as possible before it disappears; and as for containing my own emission, if I manage to make any, well,  we are outside, so what the hell, we can clean up the mess later.”

As I knelt beneath his legs and prepared to shaft him, I felt vaguely uneasy by his comment: “And as for containing my own emission, if I manage to make any.”  It implied that I might not succeed in taking him through to orgasm, with its attendant emissions. Was he suggesting that I would not succeed in my copulative endeavours, the very crux of which was my unique ability to fuck my partner right through to his own orgasm simultaneous with my own? Or was he suggesting that for some reason had a personal problem in reaching orgasm?  Either way I would show him that he would have to think again, if he was implying that I might fail, on this of all days, in the very act on which my success or failure as a male escort was based: the very same act, which had moved him after only one sexual experience with me, to declare me unique and had propelled me to my present position. If for some reason he was unable to make an emission, I was determined that one way or another, I would bring him to orgasm.

Overcoming stiff, anal resistance, as I slid my well-lubricated tool, deep into Alan’s rectum, I thought to myself; “Alan, you ain’t seen nothing yet.”  I had always had the intention of making this a unique occasion: a fuck for him to remember, in gratitude for all he had done for me. But spurred on by his chance remark, I was determined to make this the definitive fuck of his life to date. As you already know my technique was for long slow thrusts and withdrawals, building up over time to greater length and force, culminating in a complete withdrawal and a final, penetrative thrust to bring us both to a simultaneous climax.

 But this time, intent making this a very special occasion for Alan – for us both, in fact, as I enjoy fucking him as much as he enjoys being fucked by me – on each counterstroke, I withdrew my cock entirely from his anus, so that each thrust was the subject of a fresh penetration. Then with each successive thrust, time and time again, I sank my full length into Alan as I felt him grip my cock with his anal muscles, wringing every last ounce of pleasure out of each stroke. If ever a bottom knew how to render the act of anal copulation a mutual effort and make his top work for his pleasure, it was Alan! As I made each successive thrust and became increasingly aroused myself with what I was doing, I could sense the sexual tension mounting in Alan.  I increased the rhythm and force of my thrusting until he was ready to be taken to climax and was begging me to make that final thrust, that massive coup de grace, which would  unleash the  orgasm he was  by now craving, I denied him the immediate gratification he was begging me to give him. And so, for some thirty seconds, to repeated exhortations from Alan of: “Now, now, now.  Please, please do it now,” I managed to hold him in the trembling state of the excruciating paroxysms of desire to which my efforts had brought him. For a full half a minute more I delivered stroke after stroke with ever increasing force, before I finally withdrew for the very last time, held my penis, dripping with my own cum, clear of his anus for several seconds, before re-plunging it back inside him with the greatest force I could muster.

The simultaneous orgasm, always my ultimate objective, which my very special efforts triggered, was, for me, and I guessed from his reaction, also for Alan, nothing short of mind blowing in its intensity and length.  My long strokes, which had been made more effective for both of us by Alan’s continuous control of his anal sphincters, augmented by my delaying tactics,  had kept both of us on the edge of orgasm for so long that our climaxes, when they finally came, were accompanied by veritable Niagaras of sperm. As Alan had wished from the outset, I deposited my load inside of him in a series of violent jerks, totally beyond my control, whilst he shot his contribution to this simultaneous orgasm equally violently all over my naked chest and stomach. I doubt if ever before or since, two men have experienced the feelings which Alan and I had achieved in perfect harmony together. It was, for both of us a moment of utter triumph, which sealed an unwritten agreement between us.

For a full hour we remained entwined in each other’s arms before we finally moved back into the shower off the bedroom to wash the considerable traces of our joint travails off ourselves. Alan was beside himself with the praise he bestowed on me for my efforts. He found it hard to understand how he himself had contributed to the intensity of what we had just done together.

“You, Alex, are just the greatest. I have had sex with many different guys since I was sixteen; but none of them has ever held a candle to you when it comes to delivering the goods. That was, without a shadow of doubt, the greatest fuck of my life. You have a god-given gift which which will take you the heights of success in your new profession.  You will be a great success; and have men clamouring at your door for your services. And make no mistake, Alex; there are plenty of well heeled guys who will be lining up to shell out hard cash to experience your unique delivery. Look what you have achieved in you spare time in just one week,  Now that you have this place to which you can bring your clients, I think you should bite the bullet, quit your present job  and devote yourself fully to the development of your future career. And let’s face it, you will be doing something at which you are an absolute crack and which also gives you great satisfaction coupled with a great deal of pleasure.”

Chapter 12

I shared wholeheartedly Alan’s statement that what we had just done together was, as he put it, the great fuck of his life.  It had been for me too, a unique experience; never previously had I had an orgasm of such searing intensity, coupled with such an enormous emission of sperm. And I think that what Alan and I had just done together was the final factor which prompted me to stop dithering around and decide to take my future into my own hands. So I handed in my notice at the supermarket and one week later, now master of my own destiny, I received my first client in Alan’s apartment. What Alan had said about my success in my first week was quite true. By the end of that week, after I had serviced the two guys at the Howard Hotel, I will not say that my telephone never stopped ringing as that would be an exaggeration; but I was receiving regular calls for my services, and I could already see that my future was already secure.

From then on, I went from strength to strength, mainly by word-of-mouth recommendations. Writing this retrospectively after five years into of my career as a male escort, I have Dr. Alan Greenberg to thank for, let us say, detecting my talents and nurturing them. Gay, male sex at the high-end of the market, in which I practise it, certainly pays well and thanks to him, I have become comfortably wealthy beyond my wildest dreams.

Epilogue

It would be remiss of me to leave you in the dark as to my personal life, now five years down the line from when this story first began.

My sex life had obviously become more intense as I am now using my sexual assets to earn my living. However, my life is based on the rock-solid foundation that Carlo and I are an unsplittable item and always will remain so until the end of our days. That is not to say the both of us always keep to the straight and narrow path of monogamy; and it is is precisely that both of us enjoy the casual sex offered by the gay spots of Chicago that my career came about. Carlo accepted – indeed encouraged me – to turn my unique talents for gay sex and pursue the suggestion of Alan Greenberg to attempt to become a male escort, even though it meant that he would be sharing my sexual talents with other men, more or less on a daily basis.

 Before I myself had started to accompany Carlo on his forays into Chicago’s gay night spots, I had been insanely jealous of the guys, unknown to both of us, with whom he had casual sex.  But after I started accompanying him, I realised that both he and I enjoyed recreational sex outside of our own personal relationship and that come what may, it was the deep and lasting love we had for each other that was the cornerstone of our lives and would withstand our individual sexual dalliances. It was the realisation and acceptance of this fact that allowed me attempt to launch my career – successfully as it turned out – as a male escort.

Of course, my daily commercial activities cannot be considered as sexual dalliances, as they are devoid of any meaning for me beyond the commercial. But both Carlo and I still enjoy having casual, recreational sex with other men, as we both have realised and accepted the fact that casual sex outside our special relationship will not affect it.  I have more or less divided my sex life into a number of categories, ranked in order of the pleasure I get from them. Never a truer word was ever said about sexual intercourse than “Sex is a toy which never fails to please.” And in spite of having sex more or less on a daily basis and professionally often several times a day, I am happy to say that  I always enjoy the act; it never becomes old hat and bores me!

However, I have discerned that I derive varying degrees of pleasure from the act depending on who my partner is and also whether I am acting as top or bottom.  But with whomever I have sex, it is always when I act as top that I get the greatest pleasure from what I personally consider the most pleasurable pastime in life.

No sex is better than that which I have with my partner Carlo. I can come home to him after a day servicing up to three – and occasionally even four clients – and still derive greater pleasure having sex with him, whether as top or bottom, than with anyone else in the world.

Next comes the sex I have on a one-to-one basis with a few, very favoured friends such as Alan and Antonio. I suppose, but do not ask, that Carlo, in his job at the gym, has occasional, sex with some of the customers, many of whom, as I know only too well myself as I still work-out there myself, are  just  irresistible.

Then comes the group sex at parties, which Carlo and I regularly enjoy with our closest friends: Alan and Jeremy, Dave and Zach, and Antonio, who, I am happy to say, has found and moved in with a  partner called Jonathan, both of whom have become our close friends. So we four couples regularly meet on a communal basis and share our varied talents with each other.

Then comes my professional life, which fortunately never fails to give me pleasure; and the greatest pleasure I get from being a male escort is when I have a client – and there are quite a few: more than I had ever thought possible at the outset  – who ask me to cane their naked asses before I fuck them. For some reason corporal punishment and sex seem to be bosom companions. Certainly being invited to wield the  cane on an ass before I fuck it  arouses me to boiling point  and ensures a sterling performance from me; not, you understand, that I ever do other than my best for any client, for it is on my exceptional prowess that my reputation rests and my business has flourished.

And at the bottom of the list, but nevertheless still very enjoyable, comes the casual sex with unknown partners at gay clubs. You might think that the physical demands of my fulltime occupation and having sex with my partner, Carlo, regularly, not to mention those ever willing partners, our tried and trusty friends, sitting there on the figurative reserve bench, waiting eagerly to be called into play at a moment’s notice, would be enough for any man. But as Oscar Wilde remarked: “Enough is as good as meal; it’s a surfeit that makes a feast.” So as old habits die hard and neither Carlo nor I can resist the excitement of the unknown, we still make the occasional visit to one or other of Chicago’s gay night spots.

After I had, with Antonio’s help, landed my first ever paying client at the Howard Hotel and had gone on to catch four others by the end of the week, my nascent business never looked back. By word of mouth, coupled with Antonio’s assiduous effort distributing my business cards to his customers at the bar of the Howard Hotel, I was blessed with a regular flow of clients, both able and willing to pay the stiff fees, which thanks to Alan Greenberg’s advice, I had charged for my services from the start. 

So writing this some five years later, I am happy to report that I am fully established as one of the leading male escorts in the Chicago area and have a very well-heeled, regular clientele of both local and visiting business men, via the Howard Hotel, which has proved a goldmine for my business. I never cease to be both amazed and simultaneously thankful for seemingly inexhaustible number of sober-looking business executives, most of whom are filthy rich – they have to be,  given the prices I charge for my services – who claim to be happily  married with families of their own, but who nevertheless seem to crave sex with another man, And by the same token, I marvel about the sums they are prepared to lay out for the sort of high quality sex which I provide, which has made me comfortably rich. I am currently pulling down around $500,000 a year, which probably makes me the highest earner among the local talent.

At the end of my second year in business, I bought from Alan, the apartment he had rented to me for peanuts. It is there that I receive those of my clients whom I do not service either in their hotel rooms or their offices in the Chicago area and it is there that any client seeking discipline finds a mind-boggling range of implements of corporal punishment, many of which defy description. Carlo and I also use the place to hold our parties, for which I get a local caterer, who has a couple of gay staff members, who are prepared to strip-off themselves and serve a group of naked men engaged in gay sex.

Carlo and I are just as solidly committed to each other as we ever were. We moved to a better apartment, located not far from my business apartment and my traditional hunting ground, the Howard Hotel. Carlo and I keep our life together strictly to ourselves; no-one, not even Alan Greenberg, knows exactly where we live. I made a rule when I first started my business, that I would work Monday through Friday and keep the weekends free for Carlo and me, which has proved a winning formula for both of us.  We are sublimely happy with our lot in life; I with my escorting business and Carlo with his job at the gym, of which he has become the General Manager. All this began in a chance meeting, just six years ago, of two teenage schoolboys, who were not even friends at the time. We both count ourselves very lucky to have found each other.

THE END