“Hi, am I speaking to Jeremy?” I confirmed that he was. “Well Hi again; you don’t know me, but my name is Craig Kolanek, I’m the Chief Financial Officer of — and he named a company which meant nothing to me — but here’s the thing; I got your name and number from a business associate of mine, who said that you were a real pro at your job.” I interrupted him here to ask what job that would be. He continued: “Well Jeremy, let’s be clear to avoid any misunderstanding; and I do hope that I did not misunderstand my contact who gave me your number, but he said you are what is usually referred to as Male Escort. Is that right? Do I have the right Jeremy and the right number or am I way of course?”
“Mr Kolanek; you are not off course at all; I am the Jeremy your contact was referring to and I am, in fact, as he told you a Male Escort.” As I said that, I realised that for the first time I had tagged myself as a professional escort, just as Hal and Dave had seen me; so I had now acknowledged the fact to Kolanek, and more importantly to myself, that I was a Male Escort. “So Mr. Kolanek, what can I do for you?”
There was a pause as Kolanek gathered his thoughts before putting them into words: “Well Jeremy, the thing is this and I presume that we are now speaking in strictest confidentiality.” I confirmed that we were and wondered how he was going to get round to the delicate subject of what he wanted me to do to him. Even when it’s on a professional basis as it then was, or even when I pick someone up for a one-night-stand of recreational sex, there is always that little stumbling block to overcome before we get down to talking turkey and cut to the chase. “Well Jeremy, it’s like this; I’m a happily married guy with a nice wife whom I love and two lovely kids and we, live in a nice house and so on; but from, time to time I feel I need a little more than my wife can give me in terms of sex; don’t get me wrong, my wife and I have a great sex life together; but there is always a little more that I would like which my wife simply cannot give me; I am sure you understand what I mean; which is why I have contacted you.” I understood all too well as he went on: “So from time to time I quite like a little stimulation from another man; if you see what I mean.”
“Mr. Kolanek, I understand exactly what that you are referring to what is usually called anal stimulation; if I may out things crudely so that we both understand understand one another clearly; calling a spade a spade, you want me to fuck your arse; is that correct? But is there anything else you want from me so that we both understand where we stand? Do you want to have a return bout with me for instance?”
“Jeremy, you really are very direct, but you have said all that needs to be said. As you say I want some young man to fuck me, which is something my wife cannot do but which is something I need from time to time and so I need someone like you to help me relieve my tension. Other than that there is nothing; so I am what I suppose is known in the trade as a bottom and I do not want to play the role of top with you. So Jeremy, now that we both understand where we stand, I know your fees and they are OK and will settle with you in cash. The only thing to agree is where and when we meet; look here, I wonder if you could come to my office at close of business tomorrow, say a little after five; just come into the main entrance, ask for me; I’ll alert the doorman that I have a late appointment and he will show you up to my suite on the top floor where we can conduct our business completely undisturbed.”
He gave me the exact street address which was in the downtown business district. So it was quite clear what Kolanek expected and CCP did not appear to enter into the equation this time. As his was my first assignment where I had acknowledged the fact to both myself my third client that I was a Male Escort, I decided to get some business cards printed. I found a small print shop which could make me the cards within two hours and ordered five hundred. I thought long and hard as to what I would say on my card before settling on the following:
Jeremy
Male Escort
Stimulation and Discipline
By appointment only
Telephone xxxxxxxxx
When I went to pick up the cards around five that afternoon, the young man in the shop looked at me with hungry eyes, which had first been quite clearly focused on my crotch, handed me the cards and said, very directly: “You serious about what it says here?” To which I replied that I was. “Well how about you give me quickie in the back room and I’ll give you the cards for free?”
I guess this guy was about my age and he was really a very good looking type, well set up with blond hair. He wore stylish clothes, as I did; and I guessed that he was gay. And that is how I had a pleasant and completely unexpected adventure in the back room of his print shop. Kenneth Best (his business was called Best Print) as he told me his name was, turned out to be a very muscular young stud and was as gay as a coot; I enjoyed fucking his arse, which was our initial deal, but then as we had become more relaxed with each other, he asked me if I would like him to do the same for me. As you know, I like reciprocity and Ken, as he told me everyone called him, had a magnificent penis: a very impressive piece of meat indeed; and he certainly knew how to use it. And so what had set off as a simple one way deal — and arse fuck in exchange for 500 free business cards — turned into a two man fuck fest which went on until eight that evening. We finally finished up going out to a pizza joint to finish off the evening together; or so I had thought; Ken however, had other ideas.
“Listen Jeremy, tonight is my club night and I wondered if you would like to come with me and check out the local talent.” Having no fixed plans for the rest of the evening I saw no reason not go along with his idea and so off we went to his club. It was, of course, a gay club and a quite exclusive one at that; Ken had to show his membership card and sign me in as his guest; but once inside, I have to say that I really did have a great time. Miguel and had I pulled a number of one-night stands with bored businessmen at the Howard Hotel and had a three man evening of recreational sex; but this place was in a different league and it was the first time that I had experienced gay group-sex in the raw; and when I say in the raw, I really mean in the rawest of the raw, as everything seemed possible.
I had regularly dressed fashionably, not hiding my assets in anyway, but here many of the guys were wearing the most outrageous of clothing: figure fitting shirts, open to the waist displaying muscular pecs, often with pierced nipples and several guys were wearing something I had hitherto never seen: backless, leather pants with their two buns exposed. Ken told me that these guys all wore jock straps to keep their kit in order but leaving open that all important access to their anuses. And as I took in this extraordinary, highly erotic scene, I saw that several guys had already paired off and were having anal sex together just standing there. But the thing that struck me was just how muscular and fit looking everyone was. I remarked on this to Ken who told me that to become a member you had first to undergo and pass a totally nude interview with the committee who basically only accepted muscular guys with big packages. “You see,” said Ken, “The idea is to maintain a very exclusive gay-muscle club where everything goes; and so no one who does not meet the criteria of the committee is accepted as a member. In a word, weedy guys with little cocks are excluded; so what you are looking at here is the crème de la crème of muscular gay Chicago. Most of these guys are really the hardest of the hard-core gays around these parts and just live for sex; and then there are the likes of me; guys with the right physique who like sex a lot, but are much less extreme. But don’t worry Andy; if you want to join, you’d be accepted right away.” Frankly I was not sure that I did want to become a member but being there I saw no reason for once not to take advantage of what was on offer.
Ken, who was obviously well-known at the club, got four other guys together and the six of us then moved off to a private room where we all stripped off and had what I can but call a no-holds-barred fuckathon; you name it; we did it. I had never been fucked so many times in such a short period as I was by these guys; not that it was one sided, for I had never fucked so many holes in quick succession as I did that evening. It all began with what Ken called a warming-up round, where we each gave each other a five stroke thrust of our cocks; so I semi-fucked — if there is such a concept; by which I mean that one never came anywhere near to orgasm — five other guys and was in turn accorded the same treatment by each of them; so in a very few minutes, I made the acquaintance of five different cocks and five anuses, including Ken’s with which I was already fairly familiar; and to be fair, Ken was in a class by himself, when it came to handling his fuck-stick; like me he was, as I told you earlier, very well endowed; and let’s face it, say what you will, size is important when it comes to sex. Anyway, after that introduction I fucked and was fucked by three of the guys to climax each time, before we attempted to carry out a six man effort.
And so it went on and on. It was three in the morning before we left the place and I then staggered home and dropped into my bed. Looking back on the whole business, it seemed totally unreal that the simple act of ordering five hundred visiting cards could have set of such a chain of events leading to such an unbelievably phantasmagorical evening as I had just experienced. I marvel how I — or for that matter Ken too — had stood the course; remember that before we ever went to the club, he and I been vigorously engaged in gay sex for several hours. But sex is a great motivator and once you get started and are psyched up, aroused and on the roll, it can be difficult to stop. You might think that after a few rounds that your man-juice would have run dry, but that does not seem to be the case, for even a short pause is enough to give you fuel for another round.
I really had enjoyed the experience with Ken at his club but I had no wish ever to repeat it. I am a gay man and a very active one at that and I was just embarking on a profession where I would fuck men I didn’t even know for a living. There is a world of difference between what I did with Hal and Dave or what I would do with my third client next evening and the raw, powerful, hardcore, gay sex which I had just experienced. For me it was one of those things you needed to experience just once — but never again. I felt a little sad about Ken as he and I had had a great time together and I really liked the guy; but if he was into the extremes of sex he had just shown me on a regular basis, then I felt our potential friendship had to be left to wither. It had been a terrific one nightstand stand with Ken which I had greatly enjoyed and one hell of an experience for me at the club; but I had my first true client to worry about at the moment and that had already begun to exercise my mind; and so Ken and I parted company without any plans for another meeting.
CHAPTER 13
Next evening having completely recovered from the sexual excesses the night before, I duly presented myself at the reception of Craig Kolanek’s company, which like so many American businesses was located in a magnificent modern building in the Chicago business district. The name of the company was emblazoned on the door but told me nothing about what it did as I was a complete ignoramus when it came to commerce; but somehow that name was vaguely familiar; and then it suddenly hit me; this was the very company which my late father had so successfully run as CEO for many years and which had furnished him, and now me as his heir, with a large part of my inheritance; now here I was about to offer my services to a man whom I suppose might have been one of his senior colleagues. The doorman showed me to the lift and as he pressed the button for the top floor, he told me that Mr. Kolanek himself would meet me at the lift. He looked with interested curiosity at my tubular leather cane holder which I had over my shoulder together with a small satchel of supplies. I had decided to bring my canes with me just in case my new client had not totally divulged what he wanted. It had occurred to me that as he had received my name from either Hal or Dave, both of whom were devotees of CCP, he might just possibly be of the same persuasion. I must admit that I did have slight butterflies in my stomach as the lift stopped and I waited for the door to open to give me my first sight of my client.
Sumptuous is an understatement for the furnishings of the top floor lobby where Craig Kolanek had his office suite. As the lift door opened, I found myself looking at a really rather handsome man, well set up, who could not have been more than thirty years old. In a word he had exactly the visual profile that had I seen him by himself in the Howard Bar, I would have had no hesitation in trying to pick him up. I guess he owed his present position by belonging to that group of financial young whiz-kids whom one reads about in the press and who are multi-millionaires by the time they are thirty With a smile, he held out his hand to me and said: “Hi Jeremy; I’m Gary Kolanek; come on let’s go straight to my office.”
Kolanek’s office was little short of spectacular, dominated by a huge modern rosewood (I guess) desk and a matching conference table and chairs, all sitting on what was obviously a top-quality, luxury, fitted-carpet; the whole environment simply oozed money. On the desk were were that cliché of obligatory accessories: two silver photo frames containing pictures of his wife and his two small children: both boys. He offered me a drink which I declined and he got down to business right away. Our initial discussion was very easy; it can be a bit difficult even when both of you know what is required, for desires have to be put into action, but in this case there was no hanging around as Kolanek came straight to the point.
“Jeremy, I think we both know what it is I am looking for from you this evening; as I told you over the phone and as you can see from the photos, I am really a happy family man, but from time to time I do, nevertheless enjoy a little male-to-male sex. You see, when I was at college, I was really a bit of a stud myself, and I admit that I actually enjoyed sex with both men and women. I finally settled down to the classic heterosexual relationship with my wife; but I still have a hankering from time to time for what I suppose is gay sex; and right now is one those times; which is why I called you. Let me tell you that you come with the highest of recommendations; and just looking at you Jeremy, I have to say that at first sight, you do look a very attractive, sexy, young man; but as the old saying has it, the proof of the pudding is the eating, so shall we sample it together?”
He went and locked door to his office and then ushered me into a second room in which there was what I suppose was called a day-bed, two easy chairs and a table; leading off from this room a bathroom was visible through a partially open door. I suppose that this unexpected appendage to a normal office was justified if he had to work late at night concluding some deal or other and had to sleep in the office. But common sense told me its main use was for the purpose for which we had now entered it: to allow him to indulge in his desire for gay sex in complete privacy and away from home. We had no sooner entered this inner sanctum than he started stripping of his clothes and motioned to me to do the same. I was amazed how matter-of-fact he seemed to be about the intimate sexual act in which we were to indulge together, for he showed not the slightest sign of embarrassment as he shed his last item of clothing and stood before me totally naked. Well all I can say is that if he was pleased with what he saw when I stood naked in front of him, I was literally blown away by the sheer masculine beauty of this man who was about to pay me, what to my mind was an exorbitant fee, to fuck his arse.
It was clear that Craig was very definitely a body conscious type who looked after his physique, of which he could be justifiably proud; he had spent a lot of time and effort getting himself into his present the shape. The body I was looking at — with admiration and with more than a tinge of lust, I might add — did not just happen by accident, but was the result of a lot of dedication and hard work; there was not an ounce of fat anywhere on his body and he had splendid, beautifully defined muscles; as he turned around and I got my first view of his arse, well my heart just jumped for joy; he had that sort of bubble butt which was a dream just crying out to be fucked. All in all I had clearly tumbled by accident on a sexually very desirable young man; one with whom I would quite happily have had sex with free, gratis and for nothing had we met under different circumstances; he was just so alluringly attractive. I wondered how I should feel in view of the fact that I was here to please him and not to enjoy myself, but what the fuck, things were what they were and I really could hardly wait to get down to business with this superb hunk.
I suddenly realised that Craig was sporting a rock-hard cock, which had sprung to attention as soon as he had discarded the skimpy underpants he had been wearing and moreover, rather surprisingly, he had had all his pubic hair removed so that his man-meat was all perfectly displayed: a nice pair of balls surmounted by a very acceptable cock. But what was evident was the fact that the uncontrollable piece of meat he was pointing at me was telling him, whether he liked it or not, that it wanted some action; in a word although Craig was expecting me to fuck him, he himself appeared just as ready ready to fuck me; at least that is the message that his cock was delivering as we stood there looking at each other. I started to ask myself whether this guy was really the happily married type he purported to be enjoying the odd bout of anal stimulation, or was he, in fact, a closet gay himself, for all indications were that I was probably right.
It was an intriguing thought; was Craig a bisexual guy who liked having sex with both men and women? But I had been engaged to work my magic on his butt and we had never discussed whether he would like a return bout; and I recalled exactly what he had said when we spoke on the phone: “So I am what I suppose is known as a bottom and I do not want to play the role of top with you.” But frankly, just looking at him and his present the aroused state, I began to wonder about Craig; I found him such an attractive sexual prospect that I really hoped that things would go way beyond what we had agreed on the phone. But first things first; I was here as a professional escort and I intended to do what I had agreed to do: to fuck his arse, which was going to be a real pleasure for me.
But we could not simply go on standing there looking at each other; the moment for action had arrived. So I said to Craig addressing him now by his first name as we were then in such an intimate situation to do otherwise would be ludicrous: “Craig I practise safe sex and I always us a condom and in the interest of tidiness I would suggest you too use one as it will avoid the mess which sexual intercourse between men inevitably brings in its wake.” I opened a packet of Fukits rolled one onto my own cock, handed him the other rubber, which, with what I perceived was an expert hand, he rolled onto his own erect member, squeezing the teat to avoid trapping any air. “Craig what is your pleasure; how would you like me to take you? It’s your party, Craig and your call; just say what and I’ll be happy to oblige.” Craig looked at me and said not a word but just went over to the table and bent across it spreading his legs to give me access to his anus in what is usually known as the doggy position. I tore open one of the sachets of Fukit lubricant and applied a generous dose to Craig’s hole and surrounding area. I forced a little lubricant inside him with my finger as I wanted this first fuck to be really comfortable for him. Then I liberally anointed my own rubber clad cock with the contents the second sachet. And so the moment had arrived when I would use my cock for the first time as a declared, professional male-escort. Craig Kolanek was to be my first true client.