“Well Jeremy, I gather from your appearance that we are — how shall I put it? — on for this evening, so if you would just give me ten minutes to prepare myself, and then come to my suite on the fourth floor.”
He gave me the door number and to my surprise it was the self same suite that Hal had occupied a few days previously. I rang the bell and he opened the door and to my immense amazement — I suppose shock might be a better word — I found myself confronted with a stark-naked Dave; clearly a man who was not slow off the mark and equally clearly a man who was not afraid to show what he had to offer; and I can tell you, this guy’s credentials were well worth seeing. Hal had been well equipped but Dave was in a different league; clearly he was a guy who looked after himself physically as his body was finely honed to masculine perfection; it was the sort of physique which only comes from hours of serious training in the gym; and as for his sexual potential, well he had a cock which any guy would be proud to own; but here I admit that I was slightly relieved that it was not quite as big as mine. It was nevertheless a very attractive fuck-stick if ever there was one, and I desperately hoped that as the evening progressed he would want to let me sample his technique. Little did he know that had we met by chance in the bar, I would have been deliriously happy to have a one-night-stand with him for free: Dave was just so mouth-wateringly attractive that could feel my cock hardening in my pants as I stood there! I took all this in at first glance, standing here in the corridor with Dave holding the door open for me to enter.
Once in the room I felt totally overdressed; how could I feel any different with my client, stark naked, hovering over me? “Why don’t you make yourself more comfortable, Jeremy?” Framed as a question, I realised that I had, in fact, just been given an order to strip. So with nothing to be ashamed of, I obliged him. Dave looked at me with clear admiration in his eyes but nevertheless had a hungry look about him. I could tell from his manner that he was straining on that metaphorical leash to get down to the business of the evening, whatever that might be; For my part, I confess I was already praying — not that I have ever found prayer a very productive actrivity — that he would find me sufficiently attractive attractive to want to explore my arse with that magnificent tool of his, which I noticed was already standing to attention; but I just stood here letting him admire the view as it were, without having any idea what the next move would be. Had it been a normal pick-up, then we would have been on a level playing field and I would have had no hesitation in making the next move, which would have been to get him to fuck me with that beautiful penis of his; but this was not a level playing field; Dave thought he was buying the services of a Male Escort, for which he was frankly paying through the nose; and as such it seemed to me that he should be entitled to dictate the rules of the game for the evening. He went on: “Jeremy, you really are something, I’ve been with quite a few Male Escorts in my time but never with one quite as well equipped as you. So for starters can we open that treasure chest of goodies you have brought with you — referring of course to my cane carrier — and see what delights you have in store for me?”
“Dave, I have to come clean with you; when you said you wanted a CCP session with a cane, I was somewhat surprised as the cane is not much used here in the USA; it’s much more a British thing. So quite honestly, I’ve never been asked until now to use a cane. You see, in the past (and here I was actually telling the whole, but nevertheless, slightly misleading truth) I have just used a strap. I refrained from adding the word always as I did not want to lie to this guy, for whom I really did have the hots. But as you said you wanted the cane, I’ve brought a selection of rattan canes which is what our British cousins use all the time in their co-called public-schools; so you can take your pick of what I have brought with me.” I opened up the case of canes and allowed him to look them over.
Whilst he was examining them, I went on and added: “Anyway, Dave, although I have never actually wielded a cane myself, just for the record, I can tell you that I fully appreciate the sting that it can deliver. You see, I am half English myself and my English father sent me to an English public school where the cane never seemed to rest; I can tell you that I have lost count of the number of times when I was at school that I have got up from over the back of a chair, with my own arse thoroughly torched with the cane. In fact the school I attended seemed to specialise in delivering what we all referred to as a well-beaten arse — sorry I mean ass, of course. I can tell you that in my time there, a succession of junior and senior prefects, head-boys, housemasters and the Headmaster himself were all consummate practitioners of wielding the cane, which they did regularly and vigorously with gay abandon. But look here, to be honest, as a receiver rather than a deliverer, I myself have no experience at all of wielding the cane myself, and so if you would rather not risk your own ass to the ministrations of a beginner, then we can call the whole thing off here and now, with no hard feelings on either side.”
Dave finished examining the canes, looked at me and said: “Jeremy, you really are a very honest guy, and experienced or not with the cane, I simply cannot let you back out of our agreement; frankly Jeremy, you are easily the most attractive escort I have ever seen and I would mad not to let you show me just what you are capable of. So let’s get on with it and go into the room next door, where I will kneel on my bed with my head on a pillow and you will take this cane (he handed me the one he had chosen) and give my arse — as you seem to refer to it — a twelve cut beating for starters.”
I have to confess that it was with a slightly nervous feeling that I followed him into the bedroom where he adopted the position he had chosen for his session of CCP. I found myself presented with a perfect bubble butt: two superb, and as yet, undefiled globes. Speaking as somewhat of a connoisseur of that key part of the male anatomy, I was blown away by the sheer attractiveness of Dave’s arse; it was just crying out to be fucked and given half a chance, that is what I would have done; but that was not the way things were programmed for that evening where I was the servant and not the master. So first things first, as I prepared to give Dave’s backside the first stroke of the cane, the first of the twelve he wanted but which would also be my maiden stroke. Quite suddenly, as I looked at my target, all the reservations I had had about using the cane disappeared. My mind went back to my school days, when it my arse which was being presented to be beaten and I recalled how countless prefects had tapped gently with their cane, on my naked buttocks deciding where to place the first cut before I heard the cane swish down through the air and land with that sickening crack on my naked skin, to be followed a split second later by that inimitable, searing pain which only the cane is capable of delivering; and then the ten or so seconds pause, allowing me — or any other poor sod in the same position — time fully to appreciate the effect of that first stroke; and then the leisurely succession of what always seemed to be ever more swingeing cuts as the beating continued; to be followed finally by the relief which flooded through my body as I was told to get up and put back on my shorts.
I suppose, contemplating what I was about to visit on Dave’s arse, I saw the occasion as a sort of pay-back-moment for all the times I myself had been in the same position when at Frogmore. But here was an important difference; Dave was a willing supplicant whereas at Frogmore I had had always been a hapless victim; someone being punished for some misdemeanour or other, real or imagined; I had never voluntarily offered my arse to anyone to be beaten as Dave was now doing. Anyway the fatidic moment had arrived and I raised the cane and brought it down with a resounding crack more or less at the mid-point — the equator if you wish — of Dave’s globes; he let out a loud cry; but of what — pleasure or pain? I then went on and with the suitable appreciation pause between each stroke, gave Dave the twelve he requested. By the time I had finished I was very pleased indeed with my first efforts with the cane for I had managed to give him twelve perfectly placed stripes from the bottom of his back to the top of his legs. Having given Dave the number of cuts he had requested, I stood back admiring my handiwork and waited for the next order. Other than the odd groan or moan as I had applied the cane, Dave had remained silent as I proceeded with the caning.
He then said: “Well Jeremy to say that you claim you had never caned anyone before that was a great job you have just done on my ass. Frankly, I have been caned by quite a number of different escorts over the past couple of years; but I can tell you that not one of them knew how to lay on the cane he way you just did; you exceeded even my wildest expectations; especially after the way you deprecated your own prowess and pleaded ignorance. Well if that truly was your maiden effort, then I wonder what you will be like after you have had a bit more practice. Anyway let’s press on.” Dave had got up from his bed and was addressing me standing there directly in front of me as he said this; I could see that he was totally aroused by what I had done to him as his cock was still rock-hard and dripping a little pre-cum; as I hasten to add was mine! In fact, at one stage I had been so aroused by what I was doing, that I feared for a moment that I was going to reach orgasm and shoot my load all over his arse.
He continued: “So what I would like you to do for me now Jeremy, is to give my ass a dose of that magnificent cock of yours and fuck me as hard as you can; what I want is a really powerful, no-holds-barred fuck. That my friend is exactly what my ass is just crying out for after the beating it has just had; so don’t even think of holding back; just go for it like a wild man; that’s what I want.” And then with no more ado, he knelt on the bed again and resumed more or less the position in which I had just thrashed him; he did however spread his legs a little more to give me easy access to his fundamental orifice. It suddenly hit me that my caning of Dave’s arse, to be followed by an immediate fuck of what I had just roasted, was exactly analogous to my own introduction, not to the cane, but to gay sex. I remembered vividly that evening when the then Head-Boy, Simon Prosser had been supposed to give me eighteen cuts of the cane but then, after six strokes he had stopped and offered me a much more agreeable alternative to which I had agreed. And so my introduction to gay, anal sex had been that day, as Prosser had lubed up my arse, which he had just thrashed, and had then gone on to rob me of my anal virginity by giving me my first fuck: an act which had changed my life forever. So although today was slightly different, it was a double first for me as I had not only thrashed another man’s arse, but I was also going to fuck the very arse I had just roasted with the cane. I wondered if life as a Male Escort could ever get any better; and I was not even a true escort, remember.
Dave was waiting impatiently for me to act on his instructions. So telling him that I only practised safe sex, I rolled a condom from a Fukit twin pack onto my still hard cock, suggesting to him that he roll the second rubber onto his own member to catch his own emissions. I sort of anticipated that we both might make copious emissions by the time I had finished fucking him as we were both in a state of high arousal and I had every intention of taking him all the way to his own climax with my cock deep inside him at that magic moment of orgasm. Then with no undue haste I first lubed up my own cock before turning my attention to Dave’s arse and anus with the Fukit lubricant. I then knelt down on the bed behind him and prepared myself for the moment of truth: the moment of penetration. I have to say that I felt on much firmer ground than I had done earlier when handling the caning; Fucking butt was more or less my stock-in-trade; my cock was still rock-hard and at maximum length as I slid it smoothly and gently deep into Dave’s rectum.
I made my usual pause before beginning to fuck him properly; but as he had specifically asked for a vigorous approach, I gave him maximum power and maximum stroke-length from the word go. As I fucked him ever more vigorously, Dave urged me on to use more and more force as he really wanted his arse battered as hard as possible. Finally we both exploded together into simultaneous orgasms of great intensity and length, during which, as I had anticipated, we both produced seemingly endless streams of creamy cum. I finally collapsed across Dave’s back with the effort I had expended and he was to tell me a few minutes later, when we had both recomposed ourselves that I had given him the greatest fuck he had ever had.
But the question uppermost in my mind at that moment was what was to happen next. Left to my own devices — the evening was far from over as far as I was concerned — I would have flipped Dave over and gone on to fuck him a second time in the mission position and then hoped that he would feel sufficiently aroused to wish to give me a return round, which is the thing I secretly most wanted him to do as I always saw gay sex as a two-way deal. But it was not be; evidently Dave had had enough of my ministrations with the beating and the one-time sex act and he called it a day; so with his profuse thanks for what for him had evidently been a great evening, I left the hotel clutching $750 in crisp new notes in my greasy paws; I speak metaphorically of course. Little did Dave know that I would have gladly handed him back his money in exchange for that return fuck I had so hoped he would give me.
It was still not late; only around eight, as I had been with Dave only or little over an hour. I somehow felt let down; cheated and really still very randy by the way things had turned out. Of course, I tried to rationalise to myself that I had done my job and had been paid as a professional Male Escort, which is what Dave thought I was; but that did nothing at all to ease the fact that I personally felt totally unfulfilled and dissatisfied after the encounter I had just had with Dave. In sheer desperation, I went over to see Miguel with whom I had regular sex. When he let me into his apartment I was relieved to see that he was alone and so I was able to weep on his shoulder and he was more than willing to give my arse the fuck which I had so desired from Dave; of course it did not stop at that as we went on as we always did and I finished up drowning my sorrows in an orgy of gay sex with Miguel in his bed, where I awoke next morning to find myself alone as he had already gone off to work without waking me.
I had not told any of my acquaintances of my sexual adventures with Hal; but Miguel had been bursting with curiosity to hear how I had not only found myself inveigled by Pete into passing myself off as a professional Male Escort, but had also been cajoled into adding another string to my bow by acceding to the requests of my two clients for a dose of CCP. Miguel who was the guy among my regular partners with whom I had sex most often, was of the view — and he was right of course — that if I was being paid for my services, then the payer could call the shots. But, a fount of all knowledge as he always was, he told me that usually Male Escorts are requested to do exactly what I had done, either with or without the CP bit; basically it was always the escort who provided the action for the client; he fucked them but they did not fuck him in return. These guys paid Male Escorts basically became they wanted some anal stimulation; crudely out they wanted some guy to fuck their arses for them. So Miguel thought that my two clients were absolutely typical; they were obviously regular users of the services of professional escorts and as they had thought that is what I was, they had treated me as such.
“Look Andy,” said Miguel, “You were being paid — and royally so — for your services; so I think you just have to accept that that is how things function in that profession; you have to jump through their hoop but they do not have to reciprocate and jump through yours. Andy, what you have just experienced is not at all the same as what you and I do together; we try to please each other; whereas such guys as you have just been with, have retained your professional services to please them; to satisfy their desires and perversities. For them it is just a business deal; they tell you what they want; you deliver; they pay you; end of story. There is no emotion at all in it; and as for reciprocity; well just forget it. But just let me ask you this; did you enjoy what you did for these two guys? Did you enjoy beating their asses? Did you enjoy fucking them? If you did then I think you have got to be satisfied.
You cannot compare what you have just done, with what happens when you — or indeed the two of us together as we have done several times — pick up some guy in the Howard for an evening of recreational sex. There we are all on a level playing field and can express our desires and influence what happens; but that is something you cannot do when you are what amounts to nothing more than a hired help for the evening; you have to do the client’s bidding. Remember the old saying Andy: He who pays the piper calls the tune. Frankly my friend, I think that you did OK for your maiden openings; the question is: what happens next?”
And here Miguel, perceptive as ever, had put his finger on the key point; frankly I had no idea what should happen next. I had allow myself to become involved in something which I had not completely understood; I had been disappointed in one way that after giving each of my clients a really good dose of anal sex, my efforts had not aroused them enough to make them want to do the same for me. Sex apart, I had to admit to myself that in spite of my initial misgivings, it would be quite wrong to say that I had not enjoyed the experience. Frankly I had found it quite exhilarating and erotically simulating to beat my first clients; it somehow seemed to compensate for all those beatings I had taken myself at Frogmore; and the anal sex I had had with them, was, as ever, a very satisfying experience; one which however many times it is repeated, just never fails to please. And then there was the additional bonus that I had fucked two guys whom I did not know from Adam, an experience I always enjoyed immensely, which was one of the main reasons I went on my fishing trips to the Howard bar; the unknown added a little spice and sense of adventure to life. I had listened to the wisdom of Miguel and taken on board what he had said; and I suppose I now realised that he was right. I had gone into my two affairs, let’s call them, thinking that they were the same any other gay sex liaison I had with any partner, known or unknown; but I now realised that I had completely misread the situation and that I had no real right to feel put out because things had not gone according to my preconceived plan. I was playing a totally different ball-game and the question I had to ask myself was whether I had enjoyed it, in spite of what to me had been an unsatisfactory outcome; in a word, did I want to play the game according to the rules?
CHAPTER 12
After a great deal of soul searching, I decided that I would really like to go on with what I seemed to have allowed myself to slip by accident. I did not need the money as I was wealthy enough in my own right not to have to work; but as I had nothing to do most of the time, it seemed an attractive sort of an idea; and let’s face it, I was totally devoted to gay sex, which was something I could not do without in my daily life. With no need to earn my living, but having been paid twice for my services, I have to admit that here was a certain feeling of satisfaction that I could sell my sexual services for such a high price; frankly it was moral boosting and my self esteem soared; and I did admit to myself that I had really enjoyed wielding the rod on the naked arses of my two clients to date. I wondered if I had a hidden sadistic streak inside myself. But if I were to go on, how would I do it? I had not the faintest idea of how to set about developing a Male Escort business; my only two clients to date had found me rather than by me soliciting their custom. However, once again fate intervened in the form of yet another phone call; again it was from someone unknown, but with the important difference that this guy was local; I assumed him to be a business contact of either Hal or Dave, as only they knew my name, Jeremy, and had my phone number.