By now Pete, the barman, knew me too; one evening he came up to me as I was sizing up the talent and whispered: “See that young guy at the other end down there? Well he has just asked me to ask you how much you charge for your services.” So I somewhat indignantly told Pete I was not in the business of selling myself and that I came there just to have a pick-up for the evening. So Pete said: “I know that; and you know that; but he doesn’t and he thinks you are a pro. So just give me a figure and I’ll go and bounce it off him and see what he says. Look at this way; you want a pick-up for this evening; he looks like an OK guy and takes you for a pro; so why not just go along with it; so come on now, stud, name your price! But if you want to chicken out, just give me figure which will put him off.”
That is exactly what I did; or at least that is what I thought I had done, as I told Pete to say that my rate was $500 cash for two hours of therapy and $250 for each additional hour. That, I thought, would surely put the guy off; but how wrong I was; this character had obviously taken a shine to me, for Pete came back a few minutes later and said: “Right; you’re on; room 414 in ten minutes.” I gazed down the bar and looked at my client, which was what I suppose he had now become; he looked back at me and raised his glass as he stood up from the bar and left; presumably to go to his room. I marvelled that anyone would want to pay me, an unknown quantity, $500 to fuck him. I finished my drink and communicated my thoughts to Pete, that this guy must be off his rocker, to which Pete replied: “Maybe and maybe not; you know Andy, you’re one hell of a good looking young stud and the way you dress does have a sort of come-on look about it; just take a look in a mirror and you will see that anyone with half and eye can see that you have a great package. You know quite honestly if you’re ever desperate I wouldn’t mind a session with you myself. And what the fuck, you came in here tonight as you so often do, looking for a one-night-stand; well this time you’ve hit the jackpot, because not only have you got what you wanted, but you’re getting paid to do what you really like doing. My god, I would change places with you like a shot if I had your looks and your equipment.”
“You know Pete, I’m not sure that I want to go ahead with this; I don’t need $500 and I don’t like the idea of getting paid for a service which I would happily have given this guy for free. So I don’t think I’ll go up to his room after all.”
“Don’t be an idiot Andy. You can’t chicken out of this now that I have set it up to for you, Come on; be sensible; this guy is a regular client of the hotel and he looks really nice; so what more do you want? You came here tonight with a view to finding a casual fuck as you regularly do; so just go up there and give the guy what he wants and if you don’t want his dough, then just do it for free. Come on Andy, that’s what you want anyway; that’s what you came here tonight for; so stop philosophising and searching your soul about the rights and wrongs of being paid for sex; just get your arse and cock up there to his room and do the deed; it’s what he wants and it’s what you want too; so where’s the problem?”
Pete’s arguments convinced me of my obligation to go and serve this guy; so a few minutes later I rang the bell on the door of his room to be ushered in by him to what was a full suite. My client, as I now thought of him, was a young man in his early thirties; he was well-set-up and really very handsome; just the type whom I would have been overjoyed to have picked up in my normal manner; but somehow the question of cash had added a vaguely rotten odour to the whole occasion, which I found hard to shake off. He looked at me and said: “Hi; come on in and let’s get acquainted: I’m Hal and you are?” So on the spur of the moment I pulled a name out of the air and said: “Jeremy; pleased to meet you!”
Ask me not why I did not give him my proper name, Andrew, or Andy as my friends called me; but I didn’t; and Jeremy is the professional name which has stuck with me ever since. I say profession although I not sure that the rather lucrative and enjoyable activity into which I gradually allowed myself to slip merits being called such. I did not realise it at that moment, but this encounter with Hal, was to prove a turning point in my life; I was in a situation where aged just twenty-one as I then was, I was about to fuck a guy for cash; but as it turned out, sex was only a part of what happened in that hotel room, I found myself introduced into a world which, I, naïve as always, had not know existed.
Hal seemed a really nice guy and took the lead as he said: “Look Jeremy, I know that this is a professional arrangement between you and me tonight, so I would like to get the rather sordid question of money question of money over and done with before we start.” And with that he handed me $750 dollars in crisp new $50 bills. I was extremely embarrassed at his largesse for it implied that he intended to engage my service for three hours; and so I said, or rather I started to say, that I really did not want any money at all, only to be cut short by Hal; and so it never got said.
“Well now that we have got that settled let’s talk turkey. Jeremy I am not actually what I suspect you think I am; I am not gay as I guess you probably are; but I do from time to time enjoy having sex with another man. You see, I am from out of town and I come to Chicago about once a month for a few days on business and although I am happily married with a lovely wife and two children and have a great regular sex life, I still hanker after something else. Look here Jeremy, I’ll level with you; at school and later at college I really enjoyed having sex with other guys, even though I am basically straight and the fact of the matter is that I still enjoy having my arse reamed out from time to time by another man; an act which my wife clearly cannot accomplish. And so when I am away from home each month, I take the opportunity of finding someone like you who can play ball with me. But I have to tell you that anal sex is not my only weakness, for I also like to have my backside beaten before sex. You see I’m one of those guys who actually enjoys having his ass beaten; it’s actually known as consensual corporal punishment or CCP for short; and believe me there are quite a lot of guys out there who are just like me and who indulge in this — well let’s call it what it is — perversion. So when I slipped you the extra $250 tonight, it was not because I wanted you to fuck the living daylights out of me for three straight hours, but because I hoped you might be willing to give my arse a good beating before you fucked me.”
“And just let me say, Jeremy, that just looking at you, even fully dressed as you still are, I think from that lovely bulging crotch of yours, you are really going to be able to deliver the goods when you get down to it. So look here Jeremy, I know that you were looking for a normal type pick- up in the bar tonight, as most local Male Escorts (he used that expression telling me what he evidently had taken me to be) know it is really the top place in town for high-class, male, sexual encounters. So as soon as I saw you, I found you immediately very attractive and that’s why I slipped the bar-tender fifty to solicit your services on my behalf. So in some ways I feel a bit guilty in having got you here under somewhat false pretences or at least hoping for services over and above those normally provided by Male Escorts. So now that you have the full facts, are you willing to meet my needs? If you don’t want to get involved in CCP, then we can call the whole thing off and you can keep the cash anyway for your trouble. So what’s the deal? Will you or won’t you?”
You will probably think me super-naïve to be unaware that CCP existed; but until that moment, I honestly didn’t. From my many, painful, personal experiences of the cane applied to my own backside at Frogmore, I thought he must be stark, raving mad to want someone to flog his arse for him. But I have to say, never having been made a prefect at Frogmore and having always been on the receiving rather than the giving and of the cane or birch, I was intrigued at the thought of beating someone else’s arse: an act that until that moment I had honestly never even thought of. I confess with some shame, that even just thinking then about the possibility of inflicting pain on someone, was already making my cock harden in my pants; and I remembered vividly how often both I personally and the person beating me at the time, either a prefect or the Head-Boy or my Housemaster at Frogmore, had normally not been able to stop our cocks hardening as he thrashed my bare arse. And I recalled quite vividly how very often after being beaten at school. I had gone straight to bed and jerked myself off to liberate my own sexual tensions.
So although I was acutely aware of the erotic effects of corporal punishment on the beaten, this was the first time that I might actually experience the potential effect it might have on me in the role of the beater rather than in my hitherto subordinate role of the beaten. So in a word I was, by chance, in a unique position; it was an opportunity just too invitingly intriguing to miss. Hal thought that I was a regular Male Escort and as such had paid the absurd sum I had pulled out of thin air for what I had assumed would be my sexual services; but then I was asked to thrash his arse before I went on to shaft him. Frankly, although the whole thing had come out of the blue, I decided that I would go along with it. I had suddenly realised that I might never ever again have the opportunity to shred another guy’s backside; and I felt that as a connoisseur of the pain which an arse beating delivers, I owed it to myself to have at least one go of delivering what I knew was a very painful experience to someone else. And anyway, Hal was a really well set-up guy who would surely be a good fuck whatever the outcome of my efforts at beating his arse. And so having warned him that I was sailing into totally unchartered waters never having beaten anyone before, I said yes.
As he heard my agreement, I saw a look of relief flash across his face; and I understood that this guy truly did want to have his arse shredded and then fucked. There was a slight pause as he digested what I had said and then he smiled and said: “Well now that that’s all settled shall strip for action? Jeremy I have to tell you that in addition to my love of occasional male sex and CCP, I do also like looking at naked, young studs like you and I would like us both to be completely naked when you beat me.”
But now I saw a fly in the ointment; beat him with what exactly? “Oh I forgot to tell you that I always carry and old razor strop which I bought in an antique shop; it’s by far the easiest thing to pack when I travel and believe me Jeremy, when well applied it is fucking painful. So you will have the pleasure of beating my backside with an implement which in days of yore was part of the spanking armoury of lots of American households.”
I told him that I had been at school in England and had a great deal of personal experience of what a well-beaten arse felt like and that I would do my very best, on this my maiden beating exercise, to see that I left him with an arse of which I was proud; but also one which, in terms of pain, also met his expectations; of course I had no idea what his expectations were. I only knew just how fucking painful the cane or birch could be and I wondered if a razor strap would allow me to develop the same sharp pain with which I was so horribly familiar. So we stripped off and stood admiring each other; he gave me a wolf whistle as he admired my body and especially my cock which was already fully erect at attention, raring to go and was at least nine inches long. Hal too was not a bad looking guy in the buff; I guess he was ten years older than me; but with a really nicely cut cock which frankly, at first sight, I hoped he might want to use on me later. In a word I really liked Hal but I shuddered inwardly at the thought of what I was about to do to him with his razor strop. But he was he client on this occasion and the client was king; so mine to do his bidding.
Hal then produced the strop from his suitcase and I saw that it was a formidable instruments of punishment instrument made of very thick, but nevertheless, supple leather. It had a shaped wooden handle at one end and the edges of the leather had been chamfered away so they were rounded and would not cut into the flesh with which they were shortly destined to mate. I guess that the leather part itself was about two feet or possibly a little longer so that with the handle one had an implement approaching thirty inches in length. I really did wonder whether this was actually an implement for sharpening the now long-abandoned cut-throat razor; or was it just a fantasy rendering specifically destined for beating arse. Anyway, in my hand it felt well-balanced and I saw no problem in meeting Hal’s, in my eyes, peculiarly perverse needs. I thought to myself as I contemplated what I was going to do to him, that when push came to shove, as it now had, I was no different to all those prefects at Frogmore who had, over the years, thrashed my arse; I wondered if all men had a hidden sadistic streak in them which could be awakened if the opportunity arose. In fact, in spite of my initial reaction, I found myself looking forward to making my maiden beating and shredding my client’s naked butt.
“So Jeremy, shall we get on with it? I would like you to begin with twelve really good swats across my backside and then we will take it from there.” I wondered how many cuts Hal had in mind as he said this as he then, with obvious previous experience, pulled forward a chair and bent across it presenting me with his muscular looking buns. But before he did that he went to his suitcase from which he extracted a jock strap which he put on. “I always wear this when I take a beating as I don’t want my balls to get in the way and a jock just keeps them out of harm’s way. It will also allow you to be totally uninhibited when you apply he strop, which is what I want; I want really to feel the pain of the strop with every stroke you give me; so don’t even think of holding back; just apply the strop with the maximum force you can.”
Armed with this exhortation, I positioned myself to his left, raised the strop above my head and brought it down with a tremendous swat on his expectant arse. I was somewhat unnerved by the crack the strop made as it found its target, but he took the blow without a murmur. “That was a good start Jeremy, so please just go on and give me eleven more just like it.” I paused a second, to see that my first blow had already left a broad, angry, red mark right across his two buns, And from I then went on and gave him the twelve he had requested, by which time his arse was bright red. I have to admit, with a certain sense of shame at my feelings that once I got into the swing of things I found myself really enjoying what I was doing. With all twelve strokes delivered I stood back to admire my handiwork. And with those twelve strokes, which I was soon to discover was for starters, I had more or less covered the whole area of Hal’s buns. I suppose I had created in my maiden beating the equivalent of what at Frogmore was known as a well-beaten arse; but unlike the cane, which leaves distinct welts across its target, the strop just leaves a red mark where it lands; but free of well-placed, parallel welts, which were the pride of prefects and the Head-Boy at Frogmore, the whole of Hal’s arse had taken on a bright-red, fiery hue, which I thought might better be described as a well-roasted arse.
But well-beaten or well roasted, one thing seemed clear to me; I had managed to deliver a really painful beating which is what Hal had wanted. However, I had apparently not fully satisfied his craving for pain; after a few moments’ pause he said: “Well Jeremy, that was absolutely great for starters but I think I would like another twelve.” I confess that I was astonished at his request for I would have thought that with his backside in the inflamed state I had created he would surely have been enough for anyone; but no; he wanted more. As I steeled myself to continue, my mind flashed back to that ghastly occasion in my last days at Frogmore, when my friend Clive and I had each been given a twenty-four stroke thrashing for smoking and drinking in a public house. I remembered vividly the excruciating pain which the Headmaster had visited on my backside with his birch and sighing inwardly when it was over — or so I had thought — only to be told that we were both to receive another twelve cuts of the senior cane on top of the birching. Now here I was with an almost analogous situation; Hal had taken twelve and was now, unbelievably asking for another twelve; the beaten was asking the beater to continue! What was this man thinking about? How could he stand what he was asking me to do to him?
But there was no doubt about Hal’s desire to continue as he said: “Come on Jeremy, don’t be shy; just give me another twelve as that is exactly what I want.” So I did exactly as he asked and I can tell you that by the time I had finished with him, I myself was in such a state of sexual arousal that my cock seemed longer and harder than I had ever hitherto known it and I was already dripping pre-cum. By the time I had finished, Hal’s backside was deep-red all over and bruises were already developing, but here was no blood; the strop did not break the skin. I guess that the strop is a bit like the classic American paddle: very painful but causing not much surface damage and therefore you can go on and on giving stroke after stroke, building up pain to untenable levels. Whether with my twenty-four strokes I had arrived at that level, I have no idea; but evidently Hal was now satisfied. As he now stood up I could see that the beating had had an erotic effect on him too, for his cock was thrusting against his jock-strap which was wet through with his emissions. “I guess I need to get rid of this,” he said looking down at the soggy pouch between his legs, “I don’t think we need it anymore.” so he just stepped out of this skimpy item of clothing and allowed his rampant cock to assume its full erect position. Like me, he too was dripping with cum.
So we stood there looking at each other without any embarrassment in view of what we had just done together. After a moment he said: “Well Jeremy, for a first time effort that was an absolutely superb performance by you; you know, I cannot remember a thrashing that I enjoyed quite so much; and believe me, I’ve had lots of experience. You really are a true pro and if you are as good at what we are to do next it will be a brilliant evening together. But my God, I’m now as hungry as a horse so why don’t I call room service and order something to eat for us before we continue. Look while I place the order, why don’t you look in the fridge in the kitchenette there (remember we were in a suite) and see what there is available to drink.”
I did as he suggested and emerged with a bottle of champagne, which he told me to open: “We can toast a successful beginning to this evening’s activities.” He said. We sat around, both of us in the all-together, drinking the champagne, which I had only rarely ever tasted previously, when the doorbell rang announcing the arrival of the room service. Hal was totally unembarrassed, as stark naked as he still was, although his member had by now calmed itself somewhat, he opened the door and let the waiter enter. The waiter, a very handsome young guy, to his credit, did not blink an eyelid when he saw the pair of us totally naked; it was as if it was a daily occurrence — and for all I knew, perhaps it was! He arranged the table and served the food he had brought but as he was doing this I noticed that he did flash me an admiring look or two and I wondered if he was gay; not that it mattered as attractive though he was, he was not in my sights on that occasion and we were certainly not prepared for a threesome. Anyway, we ate and drank and to avoid disturbance Hal pushed the dinner trolley out into the hall and hung the do not disturb sign on the door knob.