But to get back to what was about to be my own initiation into the joys of anal sex, I heard the Head-Boy undressing behind me. Then, obviously experienced in what he proposed to do to me, I felt his fingers massaging what I guess was more of the same cream as he had put onto my welts into my fundamental hole; a few seconds later, I felt the thrusting of his hard cock against my anal sphincter and him forcing himself gently but firmly inside of me. I experienced a moment of pain followed by one of ecstatic elation as I felt, for the first time what was obviously a good-sized cock inside of me. Frankly at that moment, it seemed the most natural thing in the world. Prosser then went ahead and fucked me quite vigorously for the first time in my life and I enjoyed every moment of it. And that is how I was introduced to the world of male-male sex. I say male sex, rather than gay sex; because I am not at all sure that Prosser was gay. Like so many boys at public school he may well have found himself unable to resist having sex with his school mates out of sheer frustration at the total absence of females. Anyway, Prosser’s sexual orientation mattered not one wit in the present circumstances as gay or not, he certainly was an expert with his cock.
Totally inexperienced as I then was, I just allowed him to do what he was doing to me until he finally withdrew himself and pulled me up from the stool over which I had still been bending as he was fucking me; then face to face, totally naked, but with no embarrassment at all considering that it was a first encounter between us, we both jerked ourselves off to a climax and ejaculated great gobbets of our creamy, seminal fluid over each other; it just seemed the natural thing to do to complete the sex act we had just committed together. I thought to myself; if this is punishment, then bring it on! After a short pause during which we caught our wind again, Prosser went into his private bathroom — a perk of the Head-Boy at Frogmore — to emerge with a couple of towels with which we wiped ourselves off. But it was not yet over as he clearly wanted more; he took me by the shoulder, still naked as we now both were, and led me into his bedroom where he lay down on his back on his bed and asked me to fuck him kneeling there in front of him: “Go on Stevens, just do it; you have the equipment and it looks to be ready; so just go ahead and fuck me; you really do want to do it don’t you?”
I was really shaken to the core at this request and even more so by the direct way he had told me what he wanted; somehow did not seem right that a fifth former should be asked to fuck his Head-Boy; but lust is a tremendous motivator, and being offered for the first time in my life an opportunity to sink my own meat into a real, live man was a request I could not resist; so I went ahead and did as he wanted. Prosser said to me that I should apply a little of the cream to my cock to facilitate entry, which I did. I should add that from the start of this my introduction to anal sex, my own cock remained rock-hard and I had no problem in entering Prosser, with what I knew was a really good sized penis of which I was quite proud. And frankly that first fuck was truly one of the most memorable moments of my life; I had really no idea just how hard or how long I should pound his arse but once I had established a rhythmic beat, the whole act of copulation became quite natural and I just went on until I myself climaxed inside him. He moaned with pleasure as I became more and more insistent in my pounding and at the moment of my climax, we clung to each other, face to face like limpets in which position we remained for at least ten minutes. So there in a nutshell you have a blow-by-blow account of my first time when I was aged just eighteen.
I myself knew from that very moment onwards that I was gay: a homosexual; what Prosser had done to and for me had changed my life forever; my sex life could only be with other men; of that I had not the slightest doubt; even aged but eighteen as I then was when this life-changing event took place, I had no interest in wondering what it might be like to have sex with a woman. That one act by Prosser set me on the road which I would subsequently follow and which would ultimately lead me to my career as a Male Escort. I may as well say here and now, that from this my first experience of gay sex, I simply loved both the active and passive parts equally; I enjoyed both fucking and being fucked. And to think that had I not lost my temper in class and told that odious teacher to piss off, I would never have been sent to the Head-Boy that day for punishment, which set of the chain of events which led to what I think of as my sexual epiphany. Was it worth a six-cut beating from Prosser to experience what he taught me that evening? Certainly it was; and I thanked my lucky stars that on my first experience I had been shafted by someone I thought of as really nice guy and a schoolmate whom I admired tremendously.
But to come back to the end of that incredible Friday evening with Prosser, after lying there side by side for an hour or so, I finally got up pulled back on my gym strip and went back to the changing room down the corridor where I put back on my school uniform before going back to Hanover House to my bed. It was after lights-out by the time I got back and so I did not have to undergo the ritual of showing off of the stripes on my arse to school mates; but I also considered myself lucky not have been caught by one of the House prefects who would certainly have insisted on giving my arse another dose of the cane for being afoot after lights-out. As I left Prosser, lying there on his bed, he said: “You know, Stevens, for a beginner you’re a hell of a good fuck; we should try it again some time.” But one way and another it never happened. I left to return to Chicago that summer and Prosser left Frogmore for the last time as he would be going onto university in the autumn, to read law at Oxford. In fact, I never ever saw Prosser again after the school broke up for that summer; but what happened that fateful Friday evening has remained with me forever.
CHAPTER 7
But it was in my final year at Frogmore when we were boths in the sixth-form, that Clive Garrard, my closest friend and I had started having sex together immediately at the start of the new school year that September. I suppose I was motivated by my experience with Prosser. Clive and I had become close friends as were both key members of the rugger team which drew us closer together and we just hit it off. You know how it is; two guys are attracted towards each other and things just go on from there. We had been class-mates and indeed house-mates as we both belonged to Hanover House, throughout our entire school careers, but it was not until we got into the fifth form and were both selected as junior members for the school rugger fifteen that we became really close. We were both attracted to one another sexually; but sleeping as we did in two different dormitories even though in the same House, seriously limited any mutual, experimental, sexual activity in which we might have wanted to indulge. So our joint sex acts, if you can call them that, were limited to the occasional wank together in the showers when we thought no one was around.
I suppose the key thing that had attracted us together as we entered our final year, was the fact that we were both keen rugger players who had been selected for the school’s major team. We both had very muscular bodies which we exercised together regularly in the gym. Add to that the fact that Clive was one of the few English lads who, like me, had been circumcised, so that in the showers we were the only two guys with cut cocks in what was a sea of floppy foreskins.
But it was not until we were both eighteen and I told Clive about what had happened to me on the Saturday morning after my Friday night experience with Prosser that Clive and I made our first attempt at sex with each other. After that things really got serious between Clive and me. As sixth formers we each had our own room; so that in an environment where everything is more or less public, things could now be done more discreetly and we managed to keep our liaison to ourselves. It was helped by the fact that we were both in Hanover House. Clive was anxious for me to teach him — almost the blind leading the blind as I really had very little direct practice — everything I had experienced was from what I suppose one might call “my one night stand” with Prosser.
But Clive was an enthusiastic pupil and I an equally enthusiastic, albeit rooky teacher; but even so, with the little I had to show him, we very quickly became efficient practitioners of the ancient art of anal copulation. We both fucked each other on a regular basis and I think it is safe to say that we two were as near to being an item as any two public school boys can be; although looking back on it now, I realise that our attraction was merely physical: pure sexual lust; but at the time it happened it was terrific for both of us. It is quite true that once you get over that initial hump of admitting to each other that you are going to have sex together and have then decided who is going to do what to whom, sex is like falling off a log; it is very easy and a darn sight less painful. And so for that final year at Frogmore, we each satisfied the other’s needs by going at it hammer and tongs as often as we could. In a word it was an exhilarating period in my life and I would not have missed it for the world.
Clive and I, as two muscular and well-equipped young studs, somehow managed to keep our regular, carnal communion secret for that final year year of our education at Frogmore. How we avoided anyone even guessing what we were up to beats me now thinking back over it; but somehow we did and when we both finally left Frogmore at the end of the year, it was two totally confident, sexually experienced young gay men who launched themselves wider world. Neither Clive nor I had known that we were gay when we first became friends. But he like me had long suspected that his sexual interests lay with other men and once we became sexually active together as we did in that final year, both of us accepted the fact that, like it or not, we were a pair of died-in-the-wool homosexuals. It was rugger that had brought us together, but Clive was also a really brainy type, which I was not; he was top of the class in many subjects; I, in contrast, just scraped through most subjects and when we left my public exam results were just at the pass level; his were first class.
He then went on to read law at Cambridge, whilst I went back to Chicago. As our close friendship came to an end, I had no clear idea of what the future held for me. We both left Frogmore, with each of us nursing an arse which was still burning from that truly awful birching and beating we had been given by the Headmaster and the Head-Boy just two days before we finally left Frogmore. I think that we both saw that final year sexual interlude in our lives as part of the learning process: almost an extra-curricular subject to add to those which we were formally taught in class. But school and all it had given us, was now over; neither Clive nor I ever looked back; our relationship was ended and we both accepted that we now had to move on to the next phase of our lives.
CHAPTER 8
Finally back in Chicago, I found myself under attack. First from my father: “Why had I not tried harder at school and managed to get to Oxford or Cambridge?” When I pointed out to him that he himself had not gone to any university either in England or America and had nevertheless done really rather well for himself financially, he was, to say the least, displeased. Then came the onslaught from my mother; male members of her family had for generations gone to that holy-of-holies, Harvard, one of the oldest universities in the USA; full of her own self-importance and coming from what she thought of as one of Boston’s leading families — whatever that might mean — she totally overestimated her string-pulling influence in her attempts to get me accepted by Harvard. It was not at all clear to me, how she herself settled on the course she decided I should study: economics, a subject in which I had not the slightest interest whatsoever. But the only thing that mattered to her was that I should emerge three or so years later with a degree from that august seat of learning. However, when the admissions committee, or whoever oversaw the entry processes, saw my English exam results, I was left high and dry without even being called in for an interview. My mother was mortified that her efforts should have been spurned when she, coming from what she thought of as a leading old Boston family, had tried very hard, but unsuccessfully, to get me into Harvard. Frankly, I was indifferent and when the strings broke and I was left stranded, I could not have cared less. What my parent did not understand was that I truly was not college material. There is a saying that you cannot make a silk purse out of a sow’s ear and frankly my academic achievements fell into that category of animal anatomy.
But for my parents — or for my mother at least — it was absolutely out of the questions that I not pursue my education in one of the higher places of learning — her words — and so with total personal indifference, but again thanks to my mother’s persistence, I found myself enrolled to study — my mother’s choice of subject — for the coming academic year at Notre Dame (rhymes with aim and not dam, by the way) University in South Bend, Indiana, a neighbouring state to Illinois and not all that far from Chicago. The only good thing I can say about that interlude in my life — and I choose the word interlude advisedly, as my sojourn there was really rather brief — is that the college was great on sports at which I excelled; and I quickly developed a great sex life, at which I also excelled, in the fraternity to which I became affiliated. However my time there was relatively short lived due to not one but two life-changing events which occurred within a short period of each other at the beginning of my second year at college.
Both my English paternal grandparents died of natural causes within a month of each other, leaving their entire estate to me. As I mentioned earlier, my father and only child like me and his parents had never been very close for reasons unknown to me; but whatever the problem it was sufficient for them to disinherit their only child and leave everything to me, their only grandson. Now I had always known that my grandparents were well-heeled, but when the dust had settled and inheritance taxes had been paid, I was staggered to find that I had inherited a sum not far off $20 million in American money. They were a pair of wily old birds for their wills had stipulated that the entire estate passed to the surviving spouse and then, on his or her death to me, with the stipulation that their entire real-estate holdings in Yorkshire be sold and converted into cash by their executor, their solicitor in York. And so I inherited a great deal of cash without the problems associated with owning hundreds of acres of valuable farmland and buildings in another country, thousands of miles from where I lived.
I had no sooner digested the sad news of my grandparents passing, which was, of course tempered by the good news of the inheritance it had brought me, when my own father, aged only forty-eight and seemingly in good health, suddenly died of a heart attack. My mother rang me to say that he had died in a hotel room in San Francisco where he went as regular as clockwork once a month “on business.” At my mother’s behest, I flew to California to take care of things, to learn to my surprise that he had died in the act of copulating with a lady in his hotel room. Well the hotel room then turned out to be an apartment which he rented on a regular basis in which he had installed a mistress, a charming lady whom I met. What happened was that he was actually in the act of coitus with her when he suddenly died. She, poor thing, was trapped under him and had had to stretch to reach the phone to call for help.
By the time I got there, he was already in the city morgue awaiting an autopsy, the results of which were that he had died of a myocardial infarction; he had survived his father (his mother had died first) by only two months. The coroner released his body very quickly and I arranged for it to be sent back to Chicago for burial. I thanked my lucky stars that the San Francisco apartment was only rented, but I felt sorry for his lady-friend who had to find somewhere else to live; I am not sure how she earned her living, but that was really none of my business. I flew back to Chicago having cleared matters up in San Francisco and saw no reason to burden my mother with the details of my father’s faithlessness. It was not that I felt much for my mother as frankly as we had never been close; but it seemed to me that to add the facts surrounding my father demise to her grief would be pointless; so as far as my mother and his colleagues at the company of which he had been CEO knew, he had died of a heart attack in his bed in a San Francisco hotel.
And now came the next surprise; my father turned out to have been fabulously wealthy; and I do mean fabulously! I knew we were not short of cash, but when the facts became known I could hardly believe my ears. But even more amazing than the value of his estate, was my father’s will; he left half of his entire fortune, including that Lakeshore Drive apartment, to me outright and the income from the other half to my mother but with no access to the considerable capital involved. There were two conditions attached to my mother’s legacy; on her death, the capital reverted to me in its entirety and similarly if she remarried, the capital immediately reverted to me and all income from it hitherto paid to her ceased. So quite incredibly, I was ultimately the sole beneficiary of my father’s wealth which after inheritance taxes amounted to a staggering sum just over $100 million.
I was dumbstruck to learn how rich I had suddenly become and I did wonder how, starting from nothing, he had managed to accrue such an amazing sum legally by working in a company, albeit in the top position. However mine not to question how, but thankfully to take my inheritance. But I did ponder on the sort of relationship my parents had had with each other in view of the surprising but not super-generous way he had treated his wife; and that business in San Francisco also kept me wondering. The capital providing the income for my mother, was managed by a firm of financial experts, of whom I had never heard, but in whom my father clearly had had great confidence; in his will he suggested that I allow them to continue to manage my legacy, which I decided to do as I myself had not a clue about finance and investments. I offered to let my mother continue living in the Chicago apartment for as long as she wished; but she declined. With my father’s death and free from any ties with the city of Chicago, which she hated, she decided (did I detect a sigh of relief in her voice when she told me of her intentions?) to go back and live with her mother in the old family house in Boston. And so with no other family in Chicago and my mother and grandmother nearly nine hundred miles to the east, I found myself foot-loose and fancy free in the city of my birth: a city which I loved.
Free from any financial worries and having no need to earn a living, I took the bull by the horns and dropped out of college in Indiana. I had only gone there at my mother’s nagging insistence and the subject I was studying, economics, I found as dull as ditchwater. Looking at myself in that metaphorical mirror, I accepted the fact that I was not at all college material and should try to find something else in life to keep me occupied: but what? And just believe me that I was not at that moment, thinking only about sex; although sex was a sine qua non — an essential condition — of my life, I was relieved that I did not have to explain my sexual orientation to my parents; I did wonder what my mother would think or say if I told her that her only offspring was a practising homosexual; but under the present radically changed circumstances I saw no reason to burden her with such details.