Gentlemen’s Club Ch. 08

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(All characters are 18 years old or older.)

Well, I promised that I’d post a new story as soon as I got 10 responses — so here it is. Hope you all feel it was worth the wait 🙂

Note for this story: I have a thing about using fancy language in sex scenes (as you may have noticed in Ch. 4) — I blame this on the first erotica I ever read, which were “classic” erotica books from the Victorian Era, or maybe Elizabethan or Edwardian (these weren’t the kind of books that mentioned real-world events, you know, so, even if I did know which of those name mean which time, I couldn’t tell you when the books were written) — and these books had a lot of the same stuff I write about, though they usually had a woman at the center of the action (note that I say USUSALLY — you’d be amazed what those ye olde fuckers got up to!)

If that sort of language bothers you, I suggest you skip ahead to the part that says “Jason”.

So, now that you’ve been warned — on with the show!


The boy standing in front of the desk had bright blond hair and was dressed in a school uniform. He stood rigidly before the other occupant of the room, his angelic face serious, his blue eyes wide with earnest attention.

“Do you know why I called you in today, Westerly?” the middle-aged man seated behind the desk asked, looking up from the papers in front of him at the boy.

“No, Headmaster,” Westerly replied, although the way he could not quite look the older man in the eye proving that he probably did have some idea.

“Well, I am afraid I have called your parents to come and meet me today, to discuss your behavior,” the Headmaster said, his face stern.

“My behavior, sir?” the boy asked, worry obvious in the way his suddenly began to fidget.

“Yes, Westerly. I’ve been getting constant reports about your unseemly behavior with the other students — I have had no less than five reports this week alone of teachers having sighted you exchanging a variety of sexual favors with several different young men from your age-group.”

At the Headmaster’s words, Westerly’s face began to flush, his head hanging in shame.

“Why, Master Thomson says he actually caught you,” the Headmaster looked down, obviously reading from the page on his desk, “on your hands and knees, taking young Rochester’s manhood up your backside while sucking young Jameson so deeply into your mouth that Thomson could not see so much as the root of the other boy’s penis. What have you to say for yourself, young man?”

“Oh, sir, I am so very sorry. But it is not my fault, honestly — the other boys all heard what a pleasurable fuck I am, and it seems everywhere I go someone is waving his prick at me. Forgive me, sir, but I am too weak to resist all the temptation,” the boy seemed to be honestly distressed, tears shining in his sapphire eyes, even as he gently rubbed at the tent which began to form in his uniform trousers.

“Well, I suppose a pretty young thing like yourself would attract more than your share of attention,” the Headmaster conceded. “But it does not explain the manner in which you propositioned Master Thomson the moment Jameson finished ejaculating in your suckling mouth, my lad!” the stern educator added.

“Oh, sir, honestly, I wasn’t thinking — it was the way Rochester was pumping into me, the taste of Jameson’s fresh seed in my mouth — I simply couldn’t stop myself from saying those horrible, lewd things to Master Thomson,” Westerly said, dejection showing all over his face and stance, even as his hand moved more firmly over his groin and the fly of his trousers moved farther and farther away from his body.

“Well, I think you need to show me just how contrite you really are,” the Headmaster said, slowly pushing his chair away from the desk to reveal that his own trousers were already open, his 10 inch long, 3 inch wide hard-on leaking clear fluid onto his stroking fist as he continued, “Now, bring that slatternly mouth over here and show me just how sorry you are, boy!”

As Westerly climbed onto his Headmaster’s desk, pulling his own trousers down around his thighs to give his smaller stiffy room to grow, the lighting on the stage changed so that the space behind the Headmaster’s office door, which had been dark until now, was lit to reveal a man coming onto the stage from the far side.

“Well, this must be the place,” he said, looking around at the small part of the stage which was made to look like a waiting room. The man looked to be in his late thirties or early forties, and, like Westerly, he had blond hair and blue eyes. “It is a shame that my wife could not make it to this meeting, since this is her son and not mine that is going to be discussed, but that cannot be helped,” he added to himself.

Turning towards the door, he said, “I know that I’m almost half an hour early, but surely the Headmaster will be willing to see me now.” So saying, he took another step, which brought him up to the door. Raising his hand to knock casino şirketleri on the door, the Headmaster chose that moment to cry out in his passion, “Yes, yes! Cumming!”

“Oh, he must have heard me arrive — he has just invited me to come in,” the man said, showing that he had misunderstood the shouted word.

Opening the door, the man was immediately confronted with the sight of a pair of bare, high, pale ass-cheeks wiggling enticingly from atop the Headmaster’s wide desk, the boy’s face hidden as he continued to deep-throat the monster meat the Headmaster was feeding him — causing him to stop and stare in shocked amazement just past the doorpost.

As the door opened, so did the Headmaster’s eyes, and for a moment both men looked silently at each other while the older man’s hips continued to thrust into the oblivious boy’s slurping, sucking mouth.

Quickly regaining his wits, the Headmaster reached down to grip the boy’s head, keeping him from turning to face the newcomer, the Headmaster announced in a loud voice, “Mr. Gray, you are here early!” at the sound of the other man’s name, Westerly let out a muffled squawk; his voice, as well as whatever words he had intended to say, blocked by the Headmaster’s shaft, which was still half-way down his throat.

“Well, Headmaster,” Mr. Gray said, unconsciously raising a hand to rub at his groin as his gaze wavered between looking the educator in the eye and staring down at Westerly’s bare, quivering buttocks. “I arrived sooner than anticipated, I admit — but I would never have guessed how, um, absorbing your prior appointment would be.” Gray liked his lips, his eyes now entirely riveted to the young man’s slowly undulating buttocks, the cheeks alternately tightening and loosening in unmistakable welcome.

“Oh, it’s quite all right, Mr. Gray,” the Headmaster said, letting out a deep groan as he felt Westerly move to swallow his cock all the way down his wide-open throat. “I think we may be able to conduct our business just as well now as we would later.” A sly grin suddenly appeared on his lust-flushed face, “Perhaps you would like to make yourself more comfortable? I’m sure my young friend, here, would be more than willing to accommodate you.”

“Well, he does look terribly inviting,” Gray said before turning towards the door, his expression suddenly apprehensive, “But isn’t my stepson due to arrive for our meeting?”

“Oh, no, Mr. Gray! I guarantee that young Westerly was not invited to our meeting, and will not be arriving any time soon. But, tell me — is your charming wife likely to join us?” the thought didn’t seem to bother the Headmaster as he continued to pump Westerly’s face in a steadily increasing rhythm.

“No, no, Mrs. Westerly-Gray is not going to be joining us. My wife is visiting relatives out of the country — has been for over a month now — and isn’t due back for another two or three weeks.” Gray was pulling out his erection even as he spoke, its wide, 10 inch length an angry red as he pointed it towards its intended target with one hand, the other reaching out to fondle the pale pink cheeks before running his hand underneath the enthusiastically sucking boy to squeeze and stroke the boy’s pre-cum dripping hard-on.

“Here,” the Headmaster said, pulling a small tub of lotion out of one of his desk drawer, “You’ll need this, I think. Although, I must admit, it is entirely possible that this particular boy may be well-slicked already — he has something of a reputation here at school, and I would not be at all surprised if he had come to my office directly after being serviced by a large, hard cock.”

Gray was now trembling with excitement, slapping down gobs of lubricant on the waiting ass — Westerly helping by reaching back with one hand to pull his buttocks apart, still unspeaking and his face unseen by his Stepfather — and pressing the slippery stuff in with two, then three fingers. Finally, with a quick slather onto his throbbing manhood, Gray pushed into the boy’s lubed ass, a mighty “Ohhhh!!!” of pleasure escaping his lips as he slid down the hot tunnel. “Oh, good lord! I had quite forgotten what a boy’s backside felt like! It has been so very long since I was at school, buggering and being buggered!” Taking a firm grip on the boy beneath him, Gray began pumping, his head thrown back as his pleasure quickly mounted.

As Gray’s hips gradually began to pick up speed, the Headmaster finally gave in to the pleasurable sensations emanating from his deep-throated cock and, with a long, loud moan, began to unload into Westerly’s gobbling mouth.

The lighting now changed, Gray’s upper body was suddenly in shadow — although his steadily thrusting hips and gripping hands were still clearly visible. In this new lighting Westerly pulled his face away from the Headmaster’s still-shooting cock, aiming the purple, mushroom shaped, ejaculating cockhead at his face as he said in a loud stage-whisper, “Headmaster, however am I going to get out of here without my Stepfather casino firmaları realizing who I am?” Even as he spoke, Westerly made sure to keep pushing his backside back toward the welcome invader in his rear, soft pants and moans of delight escaping his lips in between the worried words.

“Come now, my boy,” the Headmaster said in a lighthearted voice, “It is your own fault for your predicament — if you had not been so naughty, partaking in such lewd behavior, up to and including seducing you own Headmaster in his very office, you would not have found yourself in the position of being rogered by your very own Stepfather.”

“My fault! I had come into this office innocently enough, thinking you wished to speak to me about my school-work — only to have you wave your great, hard thing in my face. Whatever was I to do, other than do my best to give it pleasure? It was the same as when Master Thomson found me with Rochester and Jameson — if I had not seen Master Thomson’s thick, red cock, I would never have begged him to let me suckle it, nor let him take over filling my nether hole when Rochester finished in it a few seconds later!” Westerly’s conflicting emotions were plain to see on his flushed, cum-painted face, as he kept closing his eyes in rapture, even as he tried to plead his case. “And now my Stepfather is sure to tell Mother all about my wicked ways, and I shall be forced to leave school in shame and disgrace!”

At this last exclamation the Headmaster chuckled and said, “Did you not hear him state only moments ago how much he is enjoying himself? How dearly he had missed those very pleasures which you were so crudely enjoying with your young friends and Master Thomson on a daily basis? Make him spend inside of you, and you need not fear that he will inform on you — rather, he will do everything in his power to see to it that your indiscretions are kept secret. Also, if you give him pleasure enough, it will make him all the fonder of you — just imagine the joys the two of you can enjoy when you return home for the holidays!”

“Oh, oh! He does have a big one, does he not?” exclaimed Westerly, for a moment forgetting his worry over his predicament as a strong wave of pleasure washed over him from a particularly hard set of thrusts. Regaining his senses a second later, he said to the Headmaster, “It certainly would be fun to have this to look forward to when I return home, I admit. Very well — although I would be quite happy to have this bout last for hours, I shall do my best to shoot off his spunk inside me. But you must promise that either he or you will give me a proper seeing-to afterwards, Headmaster!”

“Oh, I promise you, my lad — your hole will not go hungry for pleasure. Here, I shall go lock the door while you milk him, so he cannot escape the moment he discovers who you are.” As he said this, the lighting on the stage returned to normal, Gray’s body once again fully visible, the ecstasy on his face all too easy to read as he tightened his grip on Westerly’s hips, his motions fast and shallow as he neared orgasm.

But it was not Gray who reached climax first — it was Westerly, the boy’s untouched prick letting out five or six spurts of thick, creamy cum all over the Headmaster’s desk. Collapsing his upper body after his unexpected orgasm, only the boy’s backside remained raised, held in place by his Stepfather’s hands and pounding cock. Muttering obscenities under his breath, Gray moved faster and faster until he cried out, “Oh, yes, lad! You are nothing more than a receptacle for my seed! No doubt you live only for the pleasure of having men spend inside you! Well, take it then! Draw out my manly juices deep inside your spunk hungry body! Ahhhh!”

Between the copious amount of cum shooting out of Gray’s cock and the force he was still putting into his thrusts, Westerly’s ass and thighs were soon dripping his Stepfather’s semen.

“I say, well done, young man!” the Headmaster exclaimed. “That is, without a doubt, one of the most thoroughly serviced backsides I’ve ever seen — and I daresay I’ve seen a well-spunked hole or two in my day.” Moving closer, the Headmaster ran a finger up a glistening thigh, carrying the thick cream he’d collected to his mouth before sucking it clean with a loud slurp. “Ah, that’s the stuff! And so much of it! But come now, sir; I admit this,” he gave a light slap to Westerly’s still-raised posterior, “is a wonderfully willing receptacle when it comes to the pleasures of flesh in flesh. But if you do not do something quickly, the poor lad’s trousers are going to be a frightful mess.” The Headmaster was, of course, referring to the fact that the heavy stream of cum running down the boy’s thighs was already beginning to soak into the uniform trousers he still had bunched around his knees.

Rather than suggest that the boy remove the garment, Gray immediately bent down and began licking and sucking at the cum-covered boyflesh, his enthusiasm and pleasure clear in the speed with which he set about his task güvenilir casino and the thorough way he chased down every last drop, even going so far as to drill his tongue as deeply as he could into the asshole he’d just finished fucking.

Such attention quickly had both his and Westerly’s cocks hard and ready once more, both man and boy reaching down between their respective legs to stroke their re-awakening members as they gave themselves over to the pleasures of Gray’s rim-job.

The Headmaster, too, had regained full erection. Reaching past Gray’s bent form he grabbed the small tub of lubricant and quickly applied a layer of it to his engorged penis. Reaching around Gray’s waist, the Headmaster undid the man’s belt and yanked his trousers down and completely off, leaving Gray wearing his tailored jacket and shirt above the waist and only his socks and shoes bellow. Rising up from where he had been crouched at Gray’s feet, the Headmaster began to apply the slippery substance to Gray’s ass-ring; the way Gray was bent over as he continued to eat out Westerly, presented the high, round cheeks perfectly to the older man’s ministrations. Once the Headmaster was satisfied that Gay’s ass could take first one, then two and three of his fingers with ease, the Headmaster positioned his cockhead at the loosened anus and slowly pushed himself into Gray’s backside.

Gray straightened up, letting out a deep groan of pained pleasure as he felt the Headmaster’s thick cock sink into his body, Gray’s hands digging into the still raised buttocks he’d buried his own sex into only a few moments ago.

“Oh, yes! It has been a while since you’ve enjoyed a man inside you, hasn’t it?” the Headmaster exclaimed. “Is it as pleasant as you remembered?”

“Oh, oh! I feel like I’m being stretched to the ripping point — but at the same time it feels so very, very good!” Gray threw his head back, licking his cum-smeared lips as he concentrated on the feeling of the Headmaster’s throbbing flesh as it slowly moved deeper and deeper into his back-passage. “Oh, I had quite forgotten the joys of manly love! Oh, yes! That’s it, push hard now! Meanwhile, I’ll put myself back inside this wonderfully accommodating boy!” Gray said, getting ready to re-enter Westerly’s waiting ass, which began to once again wiggle in a most inviting manner.

“Oh, I think it would be more pleasant for the boy if he were to lie on his back,” the Headmaster said, a wicked glint in his eyes as he slowly began to thrust in and out of Gray’s willing behind. “He has been holding himself up on by his arms all this time — I do think he’ll enjoy the sensations you’re causing him so much better once he has a chance to lie down and relax. And just think, if he’s facing you, you will be able to see his pretty little manhood as it swells and spends from the pleasure of your hard work in his rear!” Unsaid, but clearly understood by both the Headmaster and Westerly, was the fact that Gray would also have an uninhibited view of his stepson’s face in that position. It was a mark of Westerly’s level of arousal that the thought no longer caused him distress, but instead made him moan and spread his thighs wider.

“Well, the boy certainly seems keen on the idea,” Gray’s voice was a little breathless from the hard pounding his own ass was receiving, “Let’s have him turned around so we can resume our sport — my throbber,” he said, giving his erection a firm pull from the swollen base to the purple, leaking tip, “is quite eager to resume his place inside the lad’s hole!”

Giving in to Gray’s encouraging hands, Westerly allowed himself to be turned over on the wide, padded desktop, kicking his uniform pants off as he twisted around, his legs falling wide open as he came to rest on his back. But, obviously still not ready to reveal his identity to his new lover, he had his arms crossed in front of his face.

“Oh, look, Headmaster! The sweet young thing is feeling shy!” Gray exclaimed in delight as he moved to nudge at Westerly’s opening with his throbbing cock. “Well, boy — you are bold enough to take my manhood into your body, but are embarrassed to face me as I shaft your clasping tunnel? I shall have to work your passage more thoroughly, until you lose what inhibitions still remain to you, so that you will face me squarely as we take our pleasures!” So saying, Gray began a strong pumping rhythm inside Westerly’s willing body, forcing moans of lusty joy from the young man as he drove his fat 10 inches in and out.

“Go on, Gray — make the little wanton squeal with delight with your fat shaft!” the Headmaster added, avidly looking over Gray’s shoulder at the spectacle of the young man being pumped full of cock.

Keeping his arms in place, Westerly made sure to sometimes turn his head so that the audience could have a clear view of the ecstasy stamped on his clean-cut features as he took the steadily increasing pounding up his slipper back-passage.

A couple of minutes passed as Gray enjoyed his double fuck, the Headmaster’s hard thrusts inside his long-neglected chute obviously as much a source of enjoyment to him as the hot piece of boy-ass he was fucking, before he realized that the young man beneath him was still hiding behind his crossed arms.

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