So we had now got to the moment where I was about to serve Hal in the way I had thought when we met in the bar; and although he had congratulated me on my prowess with the razor strop, which had gone really well in spite of my own initial misgivings, I now felt very confident and on firm ground as I knew that I could deliver an experience to him which, with no false modesty, would be as good as it gets. I found myself hardening again at the thought of what I was about to do to him in a few seconds; just with the thought, my cock was already as hard as a rock and ready to go. What I was about to do, which was to fuck Hal’s butt, was one of the activities I enjoyed most in life and at which I was very proficient; although it was not something I did professionally as Hal clearly thought; so here I was actually being paid by this guy to do something which I would happily have done for free. Hal looked at me with eager anticipation in his eyes, as he took in visually the sheer magnificence of my cock; and make no mistake, even though I say it myself, I do look terrific when I am ready to fuck with my cock rampant in all its glory.
He said: “Gee Jeremy, you really are something, you know: the sexual equivalent of the Washington Monument; I can’t wait to feel your meat inside of me; I don’t know what you usually do but for starters I would like it lying flat on my back on the bed.” I noticed immediately that he had said: for starters, which implied that this was just the beginning of an evening of sex which is I exactly what I had been looking for when I went into the bar at the Howard that evening: an agreeable one-night stand with someone whom I could fuck with pleasure and who, hopefully, would return the favour. And in view of the beating I had just inflicted on him, I could well understand why he wanted the front entry position; frankly with his arse in the roasted state in which it now was, I marvelled that he could even bare to lie down at all; but he did; and he was the client; so mine not to reason why.
I had taken a real liking to Hal and was determined to give him the best fuck he had ever had in his life. He watched me closely as I rolled on a condom rubber and then applied a liberal dose of lubricant to my rubber clad cock. I then handed him the second rubber from the packet and suggested that he might like to roll it onto himself with a view to containing his emission when it came as I was sure it would — in spades. This was something I had taken to doing systematically ever since being given the idea by Miguel. He was, of course, quite right; anal intercourse is a very satisfying experience but just so very messy. I then asked Hal to put his feet on the bed and bend his knees so that I could lube up his vital parts. As I prepared him for intercourse, he commented on the meticulous way I prepared us both for the act I was about to undertake, saying he had never seen such care in the preparation before. I told him that good lubrication was the key to a really good fuck as I now intended to demonstrate to him.
So the moment had finally arrived and I knelt down in front of him, pushed the tip of my cock against his sphincter. I was pleased to see that Hal had a really tight anus, which is exactly how I liked it; I hate fucking a guy with a sloppy entrance; for me a really satisfactory fuck is when my partner grips my shaft and I can truly feel myself deep inside of him. I had no idea how his previous partners had gone about things, but I was determined to take Hal with me all the way to a full orgasm simultaneous with my own, which I intended to reach with my full length deep inside of him. I don’t know what he was expecting, but as I pumped away at him, I gave him the longest stroke possible each time; he moaned with obvious pleasure and when I saw he was on the verge of his climax, I finally withdrew myself completely, waited a split second before plunging myself for that final time as deeply and as hard as I could back inside of him. This was a technique I had developed to try always to give my partner a great orgasm; and with Hal, things went exactly as planned and we both climaxed together in massively explosive orgasms. I don’t know if it was the extreme state of sexual arousal in which I found myself due to the beating I had just given him, but my own emission was huge; I just pumped what seemed liked, a never ending stream of my own thick creamy sperm into the rubber deep inside of Hal’s rectum; he too, to my great satisfaction of a job well done, simultaneously jerked out his own spunk in spades, with what I can but term explosive force, into the rubber he was wearing. It truly was a moment to savour and could not have been any better. I know I was primarily there as a paid professional to serve Hal’s needs but I felt very satisfied that we had both had such had amazing orgasms; for without orgasm, the sex act becomes meaningless.
“My god Jeremy, you really do know how to give a guy what he needs. I’ve never before experienced anything quite like what you have just done to me; that, young man, was a truly stellar, mind-blowing performance; where the hell did you learn to fuck like that; you really are a true pro you know. Believe me Jeremy, I have had sex with lots of other guys but never have I had an experience like that which you have just given me; it truly was amazing; it makes you realise what sex is all about and what a sublime business sex can be. Talk about anal stimulation which is what I really wanted; well your efforts just took that to unimaginable heights. You must have a really faithful and devoted clientele if you always perform like that; you really are at the top of your profession. Now, if you are up to it after that performance, I would just love you to take me again but this time from the rear; do you think that you could managed that or are you worn out with all that effort?”
In fact I was anything but worn out, as I had enjoyed fucking him just as much as he had evidently enjoyed being fucked by me. And let’s face it, at the end of the day I am human with all the human failings; and after that shower of praise I was completely flattered by him. But don’t get me wrong; as I went ahead and did as he requested, it was not only because of the flattery, as I really did want to fuck the guy again. I suppose I could have come clean to Hal there and then and told him that I was not the experienced pro he took me for; but I said nothing and allowed him to continue believing that he had hired a professional Male Escort for the evening. From his point of view, did it matter? As far as
I could see, not at all, as he was obviously more than satisfied with my performance; and to out it crudely; he felt he was getting his money’s worth.
As I prepared to shaft him for the second time, I shuddered inwardly as I surveyed the damage which I had done to his arse, which was now showing bruising as a result of my efforts with the strop. It beat me how the guy could bear even to allow me touch him from the rear, let alone fuck him; but stand it he did; and without a murmur of pain; and once again we both enjoyed intense orgasms as we climaxed simultaneously. Hal told me that he had never been fucked by anyone before who had brought him to such unimaginable heights of sexual pleasure as I had succeeded in doing: “Jeremy, you really have the golden touch; you have brought the art of anal stimulation to its peak.” I have to say that I did feel very pleased with myself at such fulsome praise of my sexual prowess. I had always thought that I was a very competent cocks-man, possibly because every time I fucked a guy I put my heart and soul into what I was doing and did not allow it to become the banal, self-gratifying act which is so often is. This fact had obviously come through to Hal; but never before had I had such praise heaped upon me.
But how did this extraordinary evening end? Well I had hoped that after my efforts Hal would want to give me a return round. As I told you earlier, I had always viewed gay sex as a partnership: a two-way, give and take business; I enjoyed being fucked by my partner just as much as I enjoyed fucking him. But this evening it was not to be; Hal had said that he wanted anal stimulation preceded by a thrashing and that is exactly what happened; there it ended as he showed no desire to give me that return round which I so much hoped he would. But as I say, he was my supposed client for that evening and his wishes were sovereign; so matters ended there; at least they ended there between him and me; but that evening’s events were to have far-reaching repercussions which never entered my head at the time; as I left Hal’s suite that evening, I was totally unaware of the chain of events to which my one-night stand with Hal would eventually lead.
“Jeremy what you did for me this evening was really great; can you give me one of your cards so that I can contact you again the next time I am in town?” He clearly thought that I would have some sort of professional card which I handed out, which, of course, I did not. In fact I did not even have a personal card. But instead of taking this opening to come clean to him, I told him that I did not have a card on me that evening and finished up giving him my cell-phone number.
CHAPTER 11
It was less than a week later that I received a call on my cell-phone from an unknown caller: “Hi, am I speaking to Jeremy?” I almost said there was no one by that name at this number when it suddenly hit me that I was the Jeremy he wanted to talk to. So having confirmed to him that I was, in fact, the fictitious Jeremy, he went on: “Well Jeremy, I got your name from a mutual friend, a recent client of yours I believe who extolled the services which you offered as being second to none. Look here, I’m in town for a few days and at a bit of a loose end in the evenings and in view of the glowing accounts I have heard about you, I would really like to meet you and get to know you myself and get to learn more about the services you offer; might that be possible?”
So here I had another footloose and fancy-free guy, evidently looking for sex and possibly more, for what else could he want from what Hal — it had to be Hal as there was no one else who knew the name Jeremy — had evidently told him. Anyway, I decided to play hard to get for a moment so I played hard-ball with this guy and said:” What services of mine, if I have any, might you be interested in? And if I might ask who gave you my phone number and told you about me? And if we were to get together, what exactly would you be looking for?”
“Gee Jeremy you really are making me jump through the hoop here; look I’d rather not say who gave me your number except that it was one of your recent clients, who, as I to you, was very, very satisfied with what you did for him; so can we let it go at that? Anyway I gather from him that you are a very experienced Male Escort and as such I suppose you know the sort of services that your potential clients are looking for. So if I have to spell it out to you Jeremy, I’m in the market for a little anal stimulation if you see what I mean; and to be quite clear, I’m not thinking in terms of an enema, which would be anal irrigation without the stimulation I am looking for. (He laughed at his own little joke, which showed in a way how nervous he was) But my contact tells me that you are also very proficient at CCP (he used that abbreviation; so Hal had evidently had told him the entire story) and I could be interested in that are too. Look here Jeremy, let’s cut to the chase; I know your fees and they are OK so there is no problem there. So why don’t we do this? Let’s meet in the bar of my hotel and I’ll be right at the left hand end of the bar so that you can size me up before you decide on whether we should meet face-to-face; so how about that as an idea?”
So there it was; Hal had been so convinced that I was a professional escort, that he had passed on my name — or rather my pseudonym — and praised me to high heaven to this guy (very gratifying I can tell you); so here I was talking on the phone with a guy I did not know from Adam about fucking his arse and possibly thrashing it too. I really was in a slight quandary as to what I should do. This was a new experience for me: a sight unseen prospect; it was not that I objected to having sex with someone I did not know; quite the contrary as that was the purpose of my frequent fishing trips to the Howard bar, where encountering the unknown added spice to life; but here I had a man on the other end of the line who was clearly raring to go and I had no idea who he was or what he looked like: none at all. Usually at the Howard it was a case of looking first and then moving towards the kill; in other words I had already decided I liked the look of my quarry before approaching him; and let’s face it, first appearances are very important; but here it was the reverse; I was being contacted by someone I did not know.
I needed to sell myself for sex as much as I needed a hole in my head as I was already a man of independent means as it was often loftily put. Yet somehow the thought that my services were worth something intrigued me. I did not need the money, but by charging for my services, I somehow became a legitimate operator: a professional Male Escort. But I also realised that I had left Hal the other evening $750 dollars richer, which somehow, put a high value on my services, which was a gratifying fact. In fact in suggesting base fee of $500 for two hours plus $250 for each additional hour I had aimed at putting Hal off; but my — to my mind anyway — absurdly high prices had not had the desired effect.
If Bartender Pete had not stuck his oar in, I might well have finished up with Hal anyway that evening, as I had gone specifically to my regular stamping ground at the Howard Hotel with the sole objective of picking up some attractive looking guy for evening of casual sex. But Pete’s interference had changed all that and had taken me into unknown territory, to do something I had never before even contemplated: selling myself for sex. And then, when I had had a chance to come clean with Hal and tell him that I was not at all what he thought, I had not done so and had finally left him — after a marvellous evening of sex — thinking that I was a professional Male Escort. So in a way, the dilemma I was now facing was partly of my own making. Hal must have thought that in recommending me to his friend, he was doing us both a favour; what more natural than to tell your friend that you had found the most wonderful professional cocks-man in Chicago and recommend him to check it out the next time he was in town.
Anyway, in for a dime, in for a dollar, so I finally said yes to the guy. We arranged to meet the following evening in his hotel, which was — yes you guessed it — the Howard. I sensed a feeling of relief in his voice as he gave me the (unneeded) instructions as to how to find the hotel. He then went on to say that he really would like a little CCP and would I be sure to bring the necessary implement with me; he obviously assumed that it was part of the standard equipment of my profession. Well it turned out that what he preferred was the cane and so I said that I would bring one along with me. It then suddenly hit me that I had no idea at all of where I could buy a punishment cane in Chicago and if I managed to find one, how I would get it into the hotel without raising eyebrows? It is one thing walking into a hotel using a walking stick, but quite another brandishing a school cane; and did we even have the proper rattan punishment canes in the USA? — the type that all English public schools use to discipline their pupils and the only cane with which I myself was all too familiar.
Finding a cane proved no problem as an internet search turned up one of those kinky stores, located in a seedy part of the Loop, which cater for any and every perversion know to man. They had a large selection of rattan canes available, exactly of the kind with which my own arse had been intimate on a regular basis at school; and so I bought six of different calibres, all with straight handles bound in leather for a good grip; but this surprisingly resourceful store had no simple case in which I could house the canes enabling me decently to enter a hotel with my purchases. Anyway the guy who sold me the canes suggested that I go a few doors down where there was a junk shop and rummage around here in the hope that something would come to light. This turned out to be an inspired suggestion, for barely had I started my search when I came across a long tubular container made of expensive-looking, polished leather complete with a leather cap at one end and a shoulder strap. This handsome looking object, the shopkeeper told me, was an old-fashioned carrying case formerly used by architects for carting around their large, rolled-up drawings. I really felt that the Gods were with me on this mission for I had found both canes and a means of transporting them with little problem.
And so so I carried my newly acquired treasures back to my apartment, where I almost gave myself an orgasm trying out the canes, one after the other, on a cushion over a chair. Although my own arse was all too familiar with the doubtful — to me anyway — joy which a sound whacking could bring to the recipient, I had never before actually held a cane in my hand, let alone been in a position where I was shortly about to use it for its much vaunted beneficial, therapeutic properties. I had not been appointed a prefect at Frogmore and had therefore only ever been on the receiving end of that much used implement; not surprisingly I was now truly aroused by the thought of being able to exercise my skill on a willing arse. So to ensure that I did not disgrace myself that evening, I spent quite some time practising on the cushion, as I wanted my client to think that I was an experienced purveyor of corporal punishment. I had already realised that with a rattan cane I could potentially do much more damage to the guy’s arse than had been the case with Hal’s razor strop. So as an utter novice in the art of caning — and believe me it truly is an art — it seemed to me that I had to judge just how much force I could bring to bear on the guy’s naked backside to satisfy his perverse desire for pain, but at the same time not make a bloody mess of his arse; for let’s be quite clear about it; the cane can cause a lot of damage to the recipient’s arse if applied with an excess of zeal.
I arrived early at the Howard that evening. It was Pete’s night off and another barman, whom I did not know, was on duty. As I arrived, the far left-hand end of the bar was empty and I installed myself at the other end, leaning my leather case against the bar, the bartender came across and asked me what wanted to drink; looking at the case propped against the bar, asked me if I had caught any fish; presumably he thought the case contained fishing tackle. Anyway I gave him a cryptic reply, saying that I had not yet caught anything, but that I would shortly do so. He served me my drink and went away perplexed. It was around seven when my second client ever, arrived in the bar and parked himself as he had said at the far end and ordered a drink. I was relieved to see that he was a youngish man, about Hal’s age and frankly was just the sort of guy whom, at first sight, I would have targeted as a potential one-night-stander had I been on my normal fishing trip — let’s call it that — at the Howard. It then suddenly hit me that I did not know this guy’s name; he had addressed me as Jeremy on the phone but for some reason had not got around to mentioning his own name.
I do not know if he realised that I was his partner for the evening as he gazed along he bar, which was still very quiet as it was rather early. Anyway, someone had to make the first move and perforce it had to be me, so I picked up my case and moved over towards him. I suppose he then realised that I was the contact he was waiting for and as I came closer to him he said; “I’m guessing that you might be Jeremy; am I right?” I nodded my head in agreement at which he held out his hand and said: “My name’s Dave; I’m really pleased that you could make it Jeremy.” I could see whilst he was talking that his eyes were taking in the man who was in front of him who had been highly recommended by his friend; from the agreeable expression which his face immediately adopted, I could see that he liked what he saw. Like most guys who are looking for a sex partner, his eyes took in the crotch of my pants, which as ever showed a very attractive bulge of the substantial package it contained. He offered me a drink and we exchanged a few pleasantries before he come round to the business at hand very quickly.