Gentlemen's Club Ch. 04byYwashere©
This story is a work of fiction.
All characters in this story are 18 years of age or older.
The two boys huddled together under the blanket; one, the blond, was apprehensive and shy while the other, dark of hair and eye, was boastfully bold and commanding. Both wore identical pajamas with a crest on the breast pocket -- a uniform of some kind.
The room all around them was dark, the only light coming from below them -- a flashlight. In its uncertain light the bold boy was pulling out his 6 inch erection, waving it at his friend.
"Come on, Westerly, I want to see who's is bigger," he said in a conspiratory whisper, tugging slightly on the slender erection in his hand, making it grow a little thicker.
"I don't know about this, Rochester," the shy boy replied, his face flushed, tearing his fascinated gaze away from the naked flesh before him to send a worried look around the room before his eyes, magnet-like, returned to his friend's hard penis.
"Now, now, Westerly, a promise is a promise," the bold boy wheedled, leaning in to the other boy and giving him a seductive look from under his lowered eyelashes.
With a loud sigh, the blond began undoing his fly, pulling out a not-quite-soft boycock and held it up in his fist.
"Well, that's no good -- they both have to be as big as the can before we can do a proper comparison," Rochester exclaimed, letting go of his erection to show how it was standing up by itself.
"Well, I'm sorry, but I'm not tugging off in front of you, I don't care what you say," Westerly said defiantly, apparently not noticing that his hand was, in fact, moving slowly up and down his cock.
"I'll just have to get you up to snuff myself," announced Rochester. Before his friend had time to react he swooped down and began licking at the other boy's cock, his tongue swiping repeatedly at the head before traveling up and down the sides.
"What are you...? No! No! Stop, stop at once, I say!" the blond boy's blue eyes were wide with horror as his knob was being caressed, his hands both on the other boy's head -- but seeming to be holding him in place rather than pushing him away. "Oh, what a disgusting creature you are, Rochester! Oh! Oh! Hmmm," suddenly Westerly seemed to melt, his head falling back as the delicious sensations registered, drowning out his reservations.
Rochester spent some time licking and nibbling at his chum's growing hard-on, enjoying the moans of delight emerging from his friend as well as the taste of boy-flesh. But suddenly he pulled away, sitting up to stoke himself once more, a calculating look on his face as he watched his blond friend regain his senses, eyes taking a minute to re-focus as he began to look bereaved at the loss of all those lovely sensations.
"Oh, why did you stop, Rochester? It was beginning to feel so very nice," he complained, unconsciously rubbing at the head of his cock with one hand while pulling on the shaft with the other.
"And why should you have all the fun?" Rochester said loftily. "Perhaps you should show some appreciation for a friend -- especially since you said such wicked things to me while I was doing it." So saying, the dark haired boy pushed his groin forward, moving his hands towards Westerly's head.
Westerly offered a few words of token resistance as he allowed his head to be pulled down, moving slightly so that his mouth was placed squarely over the throbbing head, already leaking its nectar. Treating the cock before him like an ice-cream cone, he began licking at the head, seeming to savor the flavor of the clear fluid seeping from it before extending his tongue once more to lick at the shaft.
"Oh, that's it, Westerly! Use your tongue, up and down! Oh, oh, yes! Now take it into your mouth and suck it!" Rochester commanded, tightening his hands on the blond head in his lap, thrusting his hips upwards at his friend's mouth, which had fallen open in surprise at his words. Rochester wasted no time in slipping the head of his excited boycock into the wet cavity.
Spluttering and moaning, Westerly struggled to pull his head up while Rochester kept the pressure of his hands and moaned in appreciation at the delightful sensations.
Finally Westerly managed to lever himself up, coughing and panting, his face a deep shade of crimson. "How dare you, Rochester?! What did you think you were doing, making me take your thing into my mouth that way?" Despite his angry words, he made no attempts to move away, and his erection was still hard and throbbing in his fist.
"I am sorry, Westerly! But what you were doing gave me such a nice feeling, and I knew how much nicer being sucked would feel -- I simply could not resist. Besides, I wanted you to have the pleasure of feeling a throbber in your mouth, a feeling I myself have always found enjoyable."
"You're lying, Rochester! There was nothing pleasurable about it! You merely wanted to please yourself!"
"No, no! I'll prove it to you!" Holding on to Westerly's hips, Rochester plunged his face back down to his friend's groin, this time taking the hard boycock into his mouth and sucking strongly. Westerly's cry of surprise dissolved into a groan of bliss, his hands burying themselves in his friend's hair as his eyes closed tightly. His sounds of joy became louder as Rochester's head descended further and he began to take Westerly deeply into his throat.
Westerly's eyes were so tightly shut, in fact, and Rochester's head so deeply buried in his lap, that neither noticed as the door swung open and an imposing figure stood in the doorway.
The newcomer stood and watched the two boys sucking and being sucked for several seconds before flicking a switch. The boys sprang apart as the lights suddenly came on, showing them that they were no longer alone.
"Headmaster!" the boys cried out as they saw the newcomer's thunderous face. Neither had thought to grab hold of their uniform trousers, and so they were pooled around the boys' ankles leaving the two jutting young erections clearly visible.
"What is this!? I come here on my rounds through the boys' dormitory, checking to see that all is well with my young charges, and what do I find? Unseemly behavior of the most disgusting stripe! What do you have to say for yourselves?" the headmaster demanded, striding back and forth in front of the two boys trying to stand at attention, their hands twitching as the urge to cover themselves up warred with the demands of the stance that the arms stay at their sides.
"Sir, we must have wiggled out of our trouser in our sleep! We had both been sound asleep until the light came on!" Rochester quickly spoke up while Westerly blushed and looked down in embarrassment.
"Nonsense! I stood and observed you for a while before turning on the light. I saw you indulging in... in whatever perverted deed you were so diligently applying yourself to, young Rochester! And you were encouraging him, Westerly, in the strongest, most graphic language it has ever been my misfortune to overhear!" the headmaster continued to pace as he spoke, his face flushed with anger. "It would serve you both right if I were to contact your parents and tell them of your actions! It is only for the sake of this school's reputation that I hesitate -- that, and the fact that your behavior thus far leads me to believe that this is the first time you have done such a disgusting thing, Westerly."
Still keeping his eyes lowered, Westerly made no reply, while Rochester followed the headmaster's back and forth progress with his eyes, also keeping silent.
Suddenly coming to a halt to one side of the two boys, so he could look at both at once, the headmaster visibly came to a decision. "I won't call your parents." Westerly's eyes rose in hope to look at the headmaster's face. "But you boys must be disciplined! I would be remiss in my duties as an educator if I did not offer correction for such actions as I witnessed here tonight," the headmaster began to undo his belt from his own trousers. "Both you boys must bend over this bed and present to me your backsides."
Hesitantly, both boys turned around and bent over, presenting their firm, round buttocks to the appraising eyes of their headmaster.
Having removed his belt, the headmaster proceeded to put it to use, whacking it across first Rochester's backside, then Westerly's. He continued alternating between the two boys, spanking first one and then the other, his pace growing faster and the sounds of the belt meeting flesh growing louder. Louder too were the sounds of pain and protest coming from the bent-over boys -- "Please, sir" "I'm so very sorry, sir" "It will never happen again, sir" "Not so hard, I beg you, sir" -- although their pleas only seemed to inflame the man, inspiring him to greater efforts.
One unexpected side effect of the hard whipping and the fact that it was the headmaster's own belt being used, was that slowly the headmaster's trousers began to slip down his thighs -- exposing a monstrous erection poking through a gap in his undergarments. Not seeming to notice his own exposed state, the zealous educator continued whipping the boys, uttering further admonitions such as, "Oh, you bad, bad, boys, to do such dirty things! I'll beat the evil right out of you, I shall! Make your round, rosy little backsides sorry you induleged in such naughty things! Make your asses glow, make them burn! What bad little boys you are!"
As the beating continued Rochester reached out to his friend, his hand diving between the other boy's legs to begin fondling him, bringing his cock to life once more. After a moment of this, Westerly hesitantly placed his own hand between Rochester's legs, stroking him back. But this transgression only went unnoticed for a few minutes before the headmaster took note, and although he did not stop them from pleasuring each other, he did add this newest observation to his tirade, "Oh, you little perverts -- you like this, don't you? You know what slatterns you are -- you're reveling in it! I shall have to beat you harder, I see! Beat the naughty perversion right out of your firm little asses, make you sorry you ever played such games!"
A few minutes later, the headmaster suddenly stopped, the hand with the belt falling to his side as, for the first time, he seemed to notice his own excited state. As the beating ended, both boys turned around, still stroking each other's hard-ons as they took in the sight of their lewdly exposed headmaster.
"Oh, look what you naughty boys have done to me!" the headmaster cried out, gesturing at his prominent erection. "Rochester, get your little whore's mouth down there and suck it, while I concentrate more fully on this boy you were corrupting."
Rochester immediately stepped away from Westerly and, trousers still pooled at his ankles, knelt down in front of the headmaster, wasting no time in getting the fat cockhead into his hungry mouth. Meanwhile the headmaster reached over to bend Westerly back down on the bed, using both hands to fondle the blond boy's raised, reddened backside.
"Is he a virgin, young Rochester? Were you going to have your dirty fun in here for the first time tonight, if I hadn't come in?" Pulling the cheeks apart with one hand, the headmaster sucked on one of his fingers and then began easing the wet digit in and out of the boy's exposed, rosy hole. "Oh, yes, very tight -- you hadn't gotten in there yet, had you? Well, be a good little cocksucker and I shall allow you in there after I am done with it," the headmaster's voice grew louder with his excitement as he forced a second finger into the moaning boy before him, while below them Rochester was showing just how much he really did enjoy sucking cock, making loud, wet slurping noises as he moved his face up and down the huge, throbbing shaft.
Westerly's face was flushed , his eyes tightly shut -- whether due to embarrassment or in order to better concentrate on the sensations being induced in his backside was unclear. "Oh, sir! The feeling of your fingers is so very strange. When you touch me in there, why, it is almost like you are touching my prick, it excites me so!"
"You say such lewd things, Westerly! But don't worry, you'll get something better than fingers in a minute, my boy! Rochester, that's enough of your slobbering mouth -- go and fetch the grease I know you keep around here!" Rochester reluctantly pulled away from the manhood he'd been deep-throating and crawled under the bed, the globes of his own exposed, welt-reddened ass provocatively raised as he rooted around under the bed.
Meanwhile the headmaster bent down and pressed his face into Westerly's ass, flattening his tongue to lick up the boy's crack before pressing his face between the cheeks, his now-pointed tongue diving into the virgin aperture he had rhapsodized about.
"Oh, sir! Not your tongue! Not in there! Oh, oh, what strange things you do to me! What a feeling! Oh! OOOOH!" The boy, unable to contain himself any longer, shot a load of boycum onto the bed, pushing his ass back at the headmaster all the while as spurt after spurt arced out his twitching dick.
Just then Rochester resurfaced, balancing on one hand while holding a squeeze bottle in the other. "Here you are, sir. Shall I apply it to you, sir?"
A muffled sound emerged from the vicinity of headmaster's buried face which may have been consent, although the man did not care to pull away from the boyass he was enthusiastically eating in order to make his reply more clear. And so Rochester squirted some of the slippery contents of the bottle onto his hand and began massaging it onto the 10 inch erection which was still poking out of the headmaster's underwear. Reaching into the slit, Rochester pulled the accompanying scrotum out of the confining clothing, revealing a pair of hairy orange-sized eggs which he began to lick and nibble as his hands went back to rubbing lubricant onto the hard shaft above him as it leaked pre-cum onto his dark hair.
Finally, as Westerly's cock regained its rigidity, the headmaster pulled his face away from the sweet morsel he had been sloppily enjoying and leaned back a little. "Rochester, grease the boy's hole -- I would not have him suffer unduly at his initiation to manly love."
Still applying his mouth to the headmaster's balls, Rochester squirted more lube on his fingers and blindly reached up to press them against Westerly's dilated anus, stopping his lingual worship just long enough to make sure his hand had reached the right spot before turning back to his self-appointed task.
Once the headmaster deemed Westerly sufficiently greased, he moved Rochester's hand away and aimed his swollen member at the prepared opening. With a slow but firm motion he pushed into the no-longer-virgin ass before him, groaning in ecstasy while Westerly cried out in pain.
"Oh, sir! It hurts! It burns! Oh, please take it out, please!" Tears began flowing out of Westerly's eyes, his angelic face contorted with the agony of his first penetration.
"Be still, boy! All will be well if you just relax and hold still for a moment. I promise you, you will experience joys the likes of which you never imagined, once your body has adjusted itself to me," the headmaster said, running a soothing hand up and down the boy's uniform-covered back, his other hand holding tightly to his waist to keep Westerly from pulling away from where his sweet young backside was pressed against the headmaster's pubic hair.
Rochester, sitting on the floor and watching as the huge meat-pole disappeared into his friend, took himself in hand and stroked off in a fast rhythm. He suddenly got up and climbed onto the bed, placing Westerly's flushed face in his lap. "I know what will distract him, sir! Come along, Westerly, you owe me a suckling! And mind that it's a proper one, like the one I was giving your knob when the headmaster came in!"
Seemingly dazed, not entirely aware of what was going on around him and what he himself was doing, Westerly lifted his head slightly and proceeded to take Rochester's engorged 6 and a half inches between his sweet, pink lips, slowly suckling his way down the shaft to the half way point, where his lips were met by Rochester's hand which was gripping the shaft.
Taking Westerly's actions with Rochester as a signal, the headmaster began a slow withdrawal from the boy's tight passageway, pulling back until only the head of his cock was still embedded before slowly pushing back in. A loud moan forced its way out of Westerly's chest -- a sound not entirely of pain.
Soon Rochester was pumping his hips forward, fucking his friend's face while the headmaster fucked his ass, the fellated boy clearly approaching orgasm as wild, inarticulate sounds spewed from his mouth and he pumped faster and faster. The first spurt was deep inside Westerly's mouth, but Rochester pulled out for his next four spurts, which landed on Westerly's face and in his wide-open mouth.
Westerly's moans and groans of pleasure could now be heard quite easily as he began to plead once more with the headmaster -- only now he was begging the man to thrust harder, move faster, fill him deeper and deeper with his huge, hard cock.
The headmaster's orgasm built quickly after Rochester blew his load, his hips pounding hard against Westerly's young ass, his large, hairy balls swinging in a wide arc to slap against the boy's tight little nuts every time he slammed into the boy.
Both man and boy came together, the one shooting deep into the tight passage he'd just deflowered while the other shot onto the bed, both orgasms lasting for several minutes as the headmaster kept up his humping, pumping barrage against Westerly's backside, which in turn continued to stimulate Westerly's prostate and caused him to keep shooting his boycum.
Pulling away from the boy with a loud groan, the headmaster cast an appreciative eye on the dilated, cum-oozing asshole.
"Sir, did you not say I could have a turn inside him, once you were done?" Rochester said, breaking in to the headmaster's reverie. The boy's erection had not subsided after his ejaculation and he was once again fisting himself off.
"Why, so I did! What do you say, young Westerly -- shall we allow this rogue into you, see if he can offer you the same delight I did?" the headmaster said, deliberately stroking a finger in and out of the wet hole to keep Westerly in a receptive frame of mind.
"Well, sir, you were right about it feeling nice. So if you think I should let him in, I shall be guided by you," Westerly said, his face once again a picture of innocence -- aside from the drying cum smeared all over it.
And so the headmaster moved a few steps back, giving Rochester room to position himself behind his friend and enter him. Quickly pushing in to the hilt, Rochester immediately began a fast, hard fuck, his much smaller size easily moving within the wet and widened backside in a way which would not have been possible if it had not been breeched first by a much-larger weapon.
Westerly's second fuck lasted only a short while, and his groan at the feeling of Rochester's discharge was partly pleasure at the hot wetness injecting into him and partly disappointment at it being over so soon. "Oh, don't stop, Rochester -- it was just getting good! Do keep pushing just a little while longer, please!" But it was no good -- once he finished shooting the last dribbles of his load, Rochester stopped thrusting and pulled his limp, dripping cock out of his friend.
Slapping the spent Rochester on the back, the headmaster exclaimed, "A reasonable showing, young man. But since you did not please your mount as thoroughly as he would have liked, don't you think it only fair to allow him some sport in you own body?" Rochester began to give a coy denial, but the headmaster overruled him, saying, "Oh, come now, young sir! I know for a fact that you enjoy such things! Now bend your luscious young body over on the bed while I get you boys ready."