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The boy jack waters Chapter 2: the appraisal

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April 08, 2024 | Full Length Video : 27min 18sec

The Buyers Club had their newest, greenest initiate yet, The Boy Jack Waters, fed, watered, bathed, and groomed. Tonight, he is to be presented to the most revered senior Masters for the Appraisal ceremony. During this event, Masters Banner, Saint, and Stone will thoroughly and rigorously measure, evaluate, and assess every inch and iota of the slave boy.

Holding a clipboard with a multi-page Slaveboy data entry form, Master Banner called out for the fresh merchandise to be brought into the Appraisal Chamber. The Boy Jack was immediately brought forward, blindfolded and escorted, by Master Stone and Master Saint.

The Slaveboy ...More

The Slaveboy was placed in the center of the Chamber. A video recording device was turned on to document the proceedings. The recording would then be given to the Grandmasters to review and study before giving the Slaveboy the greenlight, allowing him to be put up for Auction.

Once the recording started, The Boy Jack Waters was asked, once again, why he was in their illustrious presence. The young, fresh-faced twink immediately replied that he was there only to serve. Master Saint’s cock jumped in his slacks when he observed a droplet of sweat trickle down from the Slaveboy’s brow. The Boy, donned in only black jockey shorts and a black silk bow tie, was fresh indeed.

Immediately the Appraisal began.

Armed with his steel clipboard and a no-nonsense, steely gaze, Master Banner called for the measurements of The Boy’s entire anatomy. Master Stone and Master Saint sized the still-blindfolded boy while Master Banner feverishly notated every ounce and inch.

No one dared say it aloud, but it was obvious that the new Slaveboy was a perfect specimen. This scrumptious peach would have the Masters at the next Auction event howling in their seats to get a taste.

After the exhaustive work of measuring and appraising the Slaveboy was complete, Master Banner announced that it was time for the second Appraisal phase. Master Saint chuckled to himself as he observed The Boy draw a sharp breath when Master Banner grabbed the Slaveboy’s junk. However, Boy Jack remained wordless, knowing any comment or complaint would nullify the contract.

The Slaveboy’s silk jockeys were summarily removed. Master Stone licked his lips as The Boy was already fully erect. The twink cock pulsed as each of the Masters rubbed, squeezed, and fondled the Slaveboy’s lovely length and satisfying girth.

Master Banner spun The Boy around to expose his tender twink bottom. Master Stone and Master Saint each placed a hand on a boy-buttock and squeezed. Absolute perfection. Master Stone couldn’t get enough of the lad’s cute ass-dimples. The Master had the wherewithal to grab a camera and snap some shots. Future potential Buyers would see the preview photos and pay top dollar to see more, most certainly.

Soon, The Boy Jack was bent over so as to gain better access to every Master’s favorite Slaveboy feature–the smooth, pink, virginal twink boy hole. Master Banner pressed his finger up against the subordinate’s pinched pucker and, to everyone’s sheer delight, there was hardly any give. Tens of thousands of dollars would be smittenly handed over by men at the Auction wanting to be the one to break that in.

After some lengthy fingering and finessing of the tight Slaveboy’s entry, Master Stone stood The Boy back up and pulled the blindfold off of him. Master Saint put a finger up to the lad’s luscious lips, indicating that he remain quiet and wait. A moment later The Boy was driven down to his knees and commanded to open his mouth.

The Boy Jack could count on one hand the number of times that he’d ever given head to another male. Master Banner wondered if The Boy could even suck a penis with any kind of competency, let alone take a huge cock into his throat. They would soon find out, as the next phase of the Appraisal was the examination of oral proficiency.

The Boy Jack proved to have a natural knack and eager aptitude. The surprisingly skilled Slaveboy utilized tongue and lips to the Masters’ great satisfaction. The Boy looked up at Master Banner while he swallowed the daddy-shaft all the way down. The Boy couldn’t help but take note: the normally ice-cold, hard gaze had softened. The Master even allowed for a brief smile. Then it was right back to business.

After the Masters had each been given a satisfactory sucking, the final phase of the Appraisal was announced. The Boy Jack knew what was coming. During his private preparations and self-pep talk before arriving for the Appraisal, the bright-eyed youth had felt confident and ready. But when Master Saint called for a spit-roast exhibition that would gauge the Slaveboy’s true readiness, the Boy Jack’s hard-on really pulsed.

Master Stone swiped his tongue against The Boy’s smooth ass crevice. Then the Master tried putting his finger inside. The hole gave way slightly better than it previously had, but not by much. Whoever fucked The Boy first was going to have to go slow, no need to wreck the inexperienced youth–not right away at least.

Truth be told, the number of penises that Boy Jack had taken in his life were likely fewer than there were men in the room with him now. Master Saint groaned and adjusted himself as he watched his comrade fingerbang the boy. Fresh meat, indeed. Master Stone kept this in mind as he tried to reckon with any reasonable certainty how the youth’s pink hole could clench so tight.

And yet, the Masters would not, could not be deterred or put off. The twink’s virginal boy hole was a treasure that would surely earn countless riches over time- if the Slaveboy could handle it. Then, when the Boy Jack, with shining, determined eyes and round gorgeous ass stuck out, wordlessly begged the Masters to bury their seed deep inside of him, they knew in that moment The Boy’s future was red hot!

Credits
Director:Brian Fitzgibbons, Foxtrot
Producer:Legrand Wolf
Show Less
Characters
MASTER BANNER

Before receiving his exclusive invitation to join the Gentleman Buyer’s Club, Master Banner was a successful shrimp boat captain. Amassing a solid gold reputation in the industry as a tireless worker and hard disciplinarian on the open water, Master Banner is no stranger to taming wild, young deckhands.

Originally from the deep South, Banner had delved into the torridly humid temperatures of the carnal Mississippi master/slave underworld. Sexually carnivorous by nature, this Master gets off on control and domination.

He has a commanding voice that tends to send a shiver up young men’s spines. Rebellious twinks will meet their match with the severe gentleman, and are quick to learn never to disobey. Harsh disciplinary action as a result of cheekiness or back-talk include, but are not limited to: intense testicle pressure training, white-knuckle anal canal stretching, and other various forms of primal subjection.

Master Banner’s freezing cold ice-blue eyes are enough to communicate the seriousness of his business. Slaveboys learn quickly to comply with each instruction immediately—no dawdling—or the consequences will leave their young minds and fuckholes feeling the brunt of severe discipline and red-hot, sultry shame.

Played by Ace Banner
MASTER STONE

Muscular army man turned businessman Master Stone has been relatively conservative when it came to his investments in the Buyers club. Though organizing auctions and groomings are his main role, he could no longer stay in the shadows with the new flock of boys coming in. His beefy, built frame looming over any of the boys is a sight to see, and it seems like the subservient boys agree!

Played by Dillon Stone
THE BOY JACK WATERS

Inexperienced, bi-curious youth The Boy Jack stumbled upon The Buyers Club quite unexpectedly. When he discovered what the sizable payout offer is to legitimate virgins, he at least had to consider it. Nervous but also very intrigued, he sat down with one of the Masters one evening and eventually agreed to contract himself out for auction.

A country boy by stock, Boy Jack originally comes from a conservative military family. Even though the young twink comes off as shy, he is quick to smile and has an enchanting gaze that could disarm even the edgiest of men.

Out on his own now, Boy Jack had bounced around from job to job, seeking something that would be both fulfilling and financially bountiful. The young man dreams of perhaps one day owning his own business, but knows that attending college is a smart first step. With financial aid being hard to come by, Boy Jack is considering all options for making some real money fast…

Played by Jack Waters
MASTER SAINT

Master Saint has the dead-serious countenance and demeanor of a holy monk. A soft-spoken gentleman giving little away, the quietly simmering DILF in reality is no tenderfoot angel.

Originally from the barren tundra and frozen wilderness of Nova Scotia, Master Saint was born into poverty and toil. By age fourteen he stowed away on a cargo ship and began a new life in New York City. You might think this huge change might have overwhelmed and traumatized him, but you’d be wrong.

The city, famed for its endless bright lights and shadowy figures looking to commit crimes, never fazed the young Saint. He dove right into the deprivation of the modern world and crawled his way through the underbelly of criminal organizations for decades, hustling and earning- and learning all that he could from the unelected overlords that truly ran the city. Master Saint became a student of power and domination.

By age 50 he was running the vast majority of the male sex dungeon clubs and bathhouses. His territory and properties boosted his financial valuation in the hundreds of millions. In the deviant underground communities, Master Saint became a kind of household name.

Then the Buyers Club came calling. Master Saint solemnly agreed to join the illustrious secret organization and rose rapidly to the forefront of the Club’s shadowy-sultry twink recruiting operations.

Played by Tyler Saint
Photos
Series
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The Boy Jack Waters series cover

The Boy Jack Waters

The Boy Jack Waters: Chapters
1. The Grooming 31mn
While flipping through community college brochures at a career fair one afternoon, Jack Waters let out a discouraged sigh. School was extremely expensive these days, and it was becoming clear that his series of odd jobs during the week was not going to cover the cost of tuition. Disheartened, young Jack was about to give up when he saw the glint of a golden ticket half covered up by a stack of sex education pamphlets. Jack was both puzzled and intrigued by the fact that the golden ticket only had an email address followed by a four digit number and a strange request to submit a picture in .jpg format. With nothing left to lose, Jack submitted the random four digit number with a random photo showing his face, then sent it to the email address. Almost immediately, an email message came back with an invitation to meet at an address uptown. Perplexed but also desperate, Jack decided to go with it. The nervous twink was met at the end of a dark alley at the edge of town by a tall, bald, handsome man in a perfectly tailored suit. It looked incredibly expensive. Jack recited the four digit secret code to the severe-looking gentleman, who nodded and then unlocked a gold-plated doorway that led into a dimly lit chamber. Jack was informed this was the ‘Vetting Chamber’. The young man gulped, but excitedly entered the room. The door was closed behind him. The older gentleman introduced himself as Master Banner. In a no-nonsense tone of voice, this man with ice-blue eyes instructed Jack to take a seat and remain silent until spoken to. A shiver pulsed up the young twink’s spine. It was both terrifying and exhilarating to be addressed in such a way. He kind of liked it, but kept a straight face as he had a feeling even a stray smile might fuck up his chances at the money. A pearl-white document was placed in front of Jack. Master Banner implored the youth to read every line. If Jack agreed to the contents of the contract, and he subsequently obeyed every command given to him going forward, the dollar amount stated at the bottom of the contract would be his afterwards. A few moments later, his veins pumping with adrenaline, the newly-renamed Boy Jack was guided into another room. Master Banner said this was the “Grooming Chamber.” In the center of the room was a large square platform. The newly signed Slaveboy was commanded to remove his clothing, hop up onto the platform, and place himself in the doggy position. The Boy Jack swallowed hard and hesitated for a moment. Master Banner snapped his fingers sharply and with a frigid, buzzer-like tone of voice, reminded the young Slaveboy that compliance was expected to be followed with haste and a sense of urgency. Anything less was unacceptable. The Boy took a shaky breath and nodded. He made a mental note and decided it would probably be wise to pick up the pace a little. Soon, Boy Jack was completely nude and on top of the grooming altar. The twink slave was quite the specimen—long, tall, with flawless skin, and clearly into physical fitness as his body was well toned for one so young. Master Banner salaciously groped every inch of the Slaveboy’s beautiful body. Boy Jack moaned and sighed in response to the intimate touch. Master Banner’s duty this evening was to prepare the slave for future buyers. The Boy, as stated in the contract, must be ready for anything—any desire that a gentleman buyer might have must be granted. And seeing that The Boy Jack was a virgin, Master Banner was required to begin the momentous ritual of preparing a Slaveboy for his first anal penetration. The Boy Jack closed his eyes for a moment, enjoying the pleasant sensations of Master Banner’s touch all over his body. Those eyes immediately snapped back open when The Boy heard the sound of a cap popping open. The suited gentleman had a large bottle of what appeared to be oil and he began applying a very generous amount all over the boy’s chest and back. The proceeding was very sensual and arousing. Boy Jack immediately sported an erection and secretly hoped that the experienced Master might permit him to stroke his own cock using the oil. Even better, Master Banner proceeded to massage the warm, gentle lubrication not just along the slave’s swollen twink member, but his hairless scrotum as well. That’s when the gentle ministrations suddenly turned more aggressive. The suited dominator held The Boy’s ballsack by the base and squeezed—hard. The Slaveboy involuntarily emitted a hiss of surprise and fear. Master Banner pressed hard up against the Boy and shushed him. Boy Jack took a long, slow breath and held it while the merciless Master continued to test the submissive’s will. Other Masters would surely expect the Slaveboy to be eager and docile-- even in the face of somewhat harsh sensation. The Boy Jack thought about the money and soon, the intensity died down somewhat. Finally, Master Banner released the Slaveboy’s testes from his tight grip and commanded The Boy to lie on his back and pull his shapely legs towards his chest, exposing his precious pink virgin hole. As he did so, the twink noticed how Master’s eyes seemed to feast on his boy pucker. The Slaveboy wondered with a slight shiver what was going to happen next. Master Banner pulled out a long, curved glass dildo and The Boy Jack took another sharp breath. The sex toy was shiny like diamonds and had two cockhead-shaped bulbs on each end. Master Banner caught the Slaveboy’s glance. Here and now was the moment of truth. Master Banner would be gentle—at first. The Slaveboy gulped loudly and took another deep breath. Master Banner poured a generous amount of oil all over the twink’s pink pucker. Then, when the Master pressed one bulbous end of the glass dildo against the Slaveboy’s anus, the older gentleman found himself aroused by hearing The Boy’s initial whine, followed quickly by a deep, primal groan as the dildo very slowly buried half-inch by half-inch deeper and deeper inside of the insanely tight anus…
2. The Appraisal 28mn
The Buyers Club had their newest, greenest initiate yet, The Boy Jack Waters, fed, watered, bathed, and groomed. Tonight, he is to be presented to the most revered senior Masters for the Appraisal ceremony. During this event, Masters Banner, Saint, and Stone will thoroughly and rigorously measure, evaluate, and assess every inch and iota of the slave boy. Holding a clipboard with a multi-page Slaveboy data entry form, Master Banner called out for the fresh merchandise to be brought into the Appraisal Chamber. The Boy Jack was immediately brought forward, blindfolded and escorted, by Master Stone and Master Saint. The Slaveboy was placed in the center of the Chamber. A video recording device was turned on to document the proceedings. The recording would then be given to the Grandmasters to review and study before giving the Slaveboy the greenlight, allowing him to be put up for Auction. Once the recording started, The Boy Jack Waters was asked, once again, why he was in their illustrious presence. The young, fresh-faced twink immediately replied that he was there only to serve. Master Saint’s cock jumped in his slacks when he observed a droplet of sweat trickle down from the Slaveboy’s brow. The Boy, donned in only black jockey shorts and a black silk bow tie, was fresh indeed. Immediately the Appraisal began. Armed with his steel clipboard and a no-nonsense, steely gaze, Master Banner called for the measurements of The Boy’s entire anatomy. Master Stone and Master Saint sized the still-blindfolded boy while Master Banner feverishly notated every ounce and inch. No one dared say it aloud, but it was obvious that the new Slaveboy was a perfect specimen. This scrumptious peach would have the Masters at the next Auction event howling in their seats to get a taste. After the exhaustive work of measuring and appraising the Slaveboy was complete, Master Banner announced that it was time for the second Appraisal phase. Master Saint chuckled to himself as he observed The Boy draw a sharp breath when Master Banner grabbed the Slaveboy’s junk. However, Boy Jack remained wordless, knowing any comment or complaint would nullify the contract. The Slaveboy’s silk jockeys were summarily removed. Master Stone licked his lips as The Boy was already fully erect. The twink cock pulsed as each of the Masters rubbed, squeezed, and fondled the Slaveboy’s lovely length and satisfying girth. Master Banner spun The Boy around to expose his tender twink bottom. Master Stone and Master Saint each placed a hand on a boy-buttock and squeezed. Absolute perfection. Master Stone couldn’t get enough of the lad’s cute ass-dimples. The Master had the wherewithal to grab a camera and snap some shots. Future potential Buyers would see the preview photos and pay top dollar to see more, most certainly. Soon, The Boy Jack was bent over so as to gain better access to every Master’s favorite Slaveboy feature–the smooth, pink, virginal twink boy hole. Master Banner pressed his finger up against the subordinate’s pinched pucker and, to everyone’s sheer delight, there was hardly any give. Tens of thousands of dollars would be smittenly handed over by men at the Auction wanting to be the one to break that in. After some lengthy fingering and finessing of the tight Slaveboy’s entry, Master Stone stood The Boy back up and pulled the blindfold off of him. Master Saint put a finger up to the lad’s luscious lips, indicating that he remain quiet and wait. A moment later The Boy was driven down to his knees and commanded to open his mouth. The Boy Jack could count on one hand the number of times that he’d ever given head to another male. Master Banner wondered if The Boy could even suck a penis with any kind of competency, let alone take a huge cock into his throat. They would soon find out, as the next phase of the Appraisal was the examination of oral proficiency. The Boy Jack proved to have a natural knack and eager aptitude. The surprisingly skilled Slaveboy utilized tongue and lips to the Masters’ great satisfaction. The Boy looked up at Master Banner while he swallowed the daddy-shaft all the way down. The Boy couldn’t help but take note: the normally ice-cold, hard gaze had softened. The Master even allowed for a brief smile. Then it was right back to business. After the Masters had each been given a satisfactory sucking, the final phase of the Appraisal was announced. The Boy Jack knew what was coming. During his private preparations and self-pep talk before arriving for the Appraisal, the bright-eyed youth had felt confident and ready. But when Master Saint called for a spit-roast exhibition that would gauge the Slaveboy’s true readiness, the Boy Jack’s hard-on really pulsed. Master Stone swiped his tongue against The Boy’s smooth ass crevice. Then the Master tried putting his finger inside. The hole gave way slightly better than it previously had, but not by much. Whoever fucked The Boy first was going to have to go slow, no need to wreck the inexperienced youth–not right away at least. Truth be told, the number of penises that Boy Jack had taken in his life were likely fewer than there were men in the room with him now. Master Saint groaned and adjusted himself as he watched his comrade fingerbang the boy. Fresh meat, indeed. Master Stone kept this in mind as he tried to reckon with any reasonable certainty how the youth’s pink hole could clench so tight. And yet, the Masters would not, could not be deterred or put off. The twink’s virginal boy hole was a treasure that would surely earn countless riches over time- if the Slaveboy could handle it. Then, when the Boy Jack, with shining, determined eyes and round gorgeous ass stuck out, wordlessly begged the Masters to bury their seed deep inside of him, they knew in that moment The Boy’s future was red hot!
3. The Auction 34mn
Master Saint sat in the auction hall watching the proceedings. It had been some time since The Collective had gathered for an auction, as those could only happen when there were enough Boys available to put on the block. The Masters of The Collective were quite satisfied with The Boys that they currently owned and were not ready to release them. There were several new Boys—Jack Waters, among them—waiting to be sold. New Boys were desirable and always brought a high price. If they were easily available to all of the bidders, though, the market for the other boys, however handsome or well-trained they might be, would be in danger of crashing and that would not be to anyone's benefit. Master Saint was in the market for a Boy. If there were rankings in the often seedy world of BDSM and kink out on the streets, Master Saint would be at the top. He has his money, if not his hands, in anything of any sexual consequence in the city. There was certainly no shortage of Boys in all shapes, sizes, and degrees of training that would fall to their knees at the snap of his fingers. However, he had learned, like so many other men who had gained admission to The Collective, that no ordinary dominant/submissive mind game out in the bars and playrooms could equal the thrill, intensity, or quality-of-service found among the ones bought and sold from the Collective’s auction block. A serious Master needs the service of a real Slaveboy, and for a Master of Master Saint’s standing and financial resources, only the best would do. In the world of ownership and service, though, “The Best” is a highly subjective and personal description. That was the question that tumbled around in Master Saint’s head. He wanted and needed a Boy, but what exactly would the best Boy be? He was a busy man, and not always a patient one. A well-trained Boy with the stamina for heavy play was usually the wisest choice. Tonight, though, he was not thinking clearly. He was feeling haunted or, to be more honest, infatuated by a new almost-virgin boy that he had helped appraise a few weeks previously. Of course, Master Saint would never easily admit that he was infatuated by anything, least of all a random pretty face that The Collective had picked up who-knows-where. Not only that, having had the privilege of participating in The Boy’s appraisal, it was not generally appropriate to bid on him at his first auction. It might well have the appearance of insider trading, as it were. Of course, Master Saint is not in the habit of respecting the concept of “appropriate.” When Boy Jack stepped out of the shadows and knelt on the block, Master Saint’s hand almost raised itself to bid. Of course he wanted to bid! No one spends that much money without wanting to. There was just something about that Boy, though. Something that Master Saint had to have. The Boy joined The Collective for the money. Not that he didn’t genuinely enjoy sex with men, of course. He had a genuine curiosity about the kinkier side of sex. He took obedience more or less in stride. It didn’t turn him on; he was simply used to it. He couldn’t really imagine any Master being more domineering and exacting than his own father, the three-star General, had been. He had watched all of the men in his family climb up the military ranks. He knew well that if you want to get to where you want to be, you start at the bottom and work your way up. If anything, given Boy Jack’s potential earnings, he considered a few years in slavery was a shortcut. The evening of the auction, several Boys went on the block before he did. The Boys had spent the afternoon being prepared for this moment with haircuts, manicures, pedicures, body grooming, sexual cleanliness, and an hour in the weightroom to fill out their physique to maximum advantage. Afterwards, they were left sitting on a bench for ages in near darkness backstage, waiting to be beckoned. After the bustle of the afternoon, the forced silence and stillness was disconcerting. The time before it was Boy Jack’s turn seemed to take forever and to rush by in the blink of an eye at the same time to him. Then the moment came. Master Banner pointed, snapped his fingers, and Boy Jack stood up and stepped around the edge of the curtain, where the spotlight blinded his eyes. He knew exactly what was happening and what was expected. They had even rehearsed the whole event earlier that morning. The confidence Boy Jack had felt those hours ago when he declined when Master Banner gave The Boy a final chance to back out faded like the cigar smoke the wealthy Buyers blow from their lips. He tried to focus on following Master Banner’s orders, but one of those was to keep his shoulders back, chin up, and eyes open at all times. That meant staring straight out into the hall. His vision was compromised by the bright spotlight, but it was clear enough to see the shadows of the men gathered to bid on the right to own Boy Jack’s body. Master Banner turned him and posed him, sensuously smearing oil over The Boy’s skin–making the youthful curves of his fit body glisten. The quiet chime pinged with the climbing bids, ringing as loud as a church bell in Boy Jack’s brain. He barely had the awareness to feel any possible shame when his ass cheeks were pulled apart to display his hole to the bidders. The disembodied voice of the announcer said, “The bidding is closed!” and it was over. Once again, Boy Jack felt like the time he had stepped out on to the stage had been both hours ago and seconds ago. Between the lights in his eyes and his disoriented emotions, Boy Jack didn’t even see the face of the man who had bought him. He was not surprised when a pair of strong arms wrapped around his chest, nor when rough hands began to explore his body. He had been told that it was a tradition for buyers to fuck their new slaves for the first time on the auction block in front of the crowd. The Master finally turned Boy Jack’s head to the side where he caught a glimpse of a familiar face. His new owner was Master Saint, the most intimidating of the three men who had appraised him. Boy Jack did not have time to think through that, much less analyze the envious lustful gazes of the men watching Master Saint use his new toy. Boy Jack’s entire focus was on the fat cock stretching his hole painfully wide and drilling hard and deep into his guts, over and over, with the power and privilege of ownership. The new life of The Boy Jack Waters had begun.
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