https://www.anarchyporn.com/models/jack-waters/ Wed 19 Aug 2026 08:15:47 +0200 https://www.anarchyporn.com/video/37882/the-boy-jack-waters-chapter-1-the-grooming/
Master Banner was ready. But by the looks of the young, innocent-looking twink standing nervously before him in the Grooming Chamber, he was certain The Boy had no idea what was about to happen. It's always the guarantee of a jackpot payday that gets the inexperienced ones in the door. But once there, sometimes they panic and fleeespecially when they see the dildo come out.On this particular evening, The Boy Jack had just signed his first contract with the Buyer's Club. The bi-curious boy had never engaged in anal sex before. Boy Jack really needed the money so he complied with every single command in return.. but not without the nervousness one might expect.Master Banner snapped his fingers and clapped his hands sharply. The newly hired Slaveboy's shyness and meek demeanor had no effect whatsoever on how the strict gentleman was going to proceed.Once the wide-eyed twink finally had his clothes off and crawled up on all fours atop the grooming altar, Master Banner wasted no time pouring smooth oil all over the boy. And the moment the DILF pulled out the long, curved glass dildo and placed the bulbous head against Boy Jack's pink, tight, virgin hole, the fresh-faced twink knew this was about to get real! ]]> Fri 12 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37882/the-boy-jack-waters-chapter-1-the-grooming/ https://www.anarchyporn.com/video/37812/apprentice-waters-chapter-2-the-calling/
I entered Master Scott's office, shaking profusely. He looked great, with graying hair and an impressive mustache. He told me I was there to take his seed. Then he ordered me to undress.He told me to kneel in front of him, thrusting his fingers into my mouth. Sometimes what he was doing made me want to gag. Then he unbuckled his belt, unzipped his pants and pulled down his garments, revealing the most massive penis which, unexpectedly, I hoped was going into my mouth. I had never done that before. I didn't know if I was doing everything right, but I figured my instinct would guide me in the right direction. I wrapped my lips around his penis and went up and down his shaft, occasionally sucking, occasionally licking. It tasted so good, although sometimes I took it too far into my mouth and it made me gag. Then he brought me to my feet and pushed me against the desk. I knew the moment had arrived. I never thought I'd be losing my virginity like this, but it was all my body wanted at that moment. I always assumed I'd be pushing my dick into someone who didn't also have a penis. And yet here I was, wondering how on earth it would feel to take something so large inside me, panicking that it would hurt like hell that my hole almost clamped itself shut. He started to rub the head of his dick against my hole. There was a lot of spit and oil down there, and it felt really good as he slipped and slid between my cheeks. There was a silence as he positioned his dick. I felt him start to push himself inside, making me wince, at first. ]]> Thu 11 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37812/apprentice-waters-chapter-2-the-calling/ https://www.anarchyporn.com/video/37818/the-boy-jack-waters-chapter-3-the-auction/
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. ]]> Wed 10 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37818/the-boy-jack-waters-chapter-3-the-auction/ https://www.anarchyporn.com/video/37774/the-boy-jack-waters-chapter-4-the-prize/
After my alone time is up, I report to his room. I wait in the hall for a few minutes to step in the door just as the clock down the hall chimes. He is very stern and gruff telling me how to undress him. I try to remember as much as I can. I think it will please him if I can do it without being instructed. He likes me to look into his eyes at all times but it's hard not to fumble without looking down.While undressing, he spins me around, spreads my cheeks, and shoves his tongue into my hole. I don't know if I'm allowed to make noise or not, but I can't hold back a moan. I start sucking his cock just hoping that I will do it right. I was expecting more growling instruction but he just laid back on the velvet duvet and sighed.He tells me to get his cock wet and that he expects me to sit on it and ride him. He feels huge in my ass. I've never been fucked by a grown man before. He doesn't seem to care how much I whimper. I think he likes knowing how difficult it is to take him. I guess every man likes to think he's hung and, in his case, he is.Soon, I'm on my stomach with him on top of me driving his dick into me balls deep, over and over until I feel like I can hardly breath. Then he lets out an animalistic grunt and I feel his sticky load spreading deep inside me. ]]> Wed 10 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37774/the-boy-jack-waters-chapter-4-the-prize/ https://www.anarchyporn.com/video/37854/the-boy-jack-waters-chapter-2-the-appraisal/
Armed with his steel clipboard and a no-nonsense, steely gaze, Master Banner called for the measurements of the entire anatomy of The Boy Jack Waters. Master Stone and Master Saint sized the still blindfolded Slaveboy while Master Banner feverishly notated every ounce and inch. 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 Jack draw a sharp breath when Master Banner grabbed the Slaveboy's junk. Boy Jack remained wordless, remembering any comment or complaint would nullify the contract.Soon, the Boy Jack was bent over so as to gain better, easier access to every Master's favorite slave boy 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 feverishly handed over by men at the Auction to be the one to break that in.Master Stone swiped his tongue against the Slaveboy's smooth ass crevice. Then the silver-daddy Master tried putting his finger inside. The hole gave way slightly better than previously, but not by much. Whoever would fuck the lad first was going to have to go slow; they surely wouldn't want to wreck the inexperienced youth. Not right away anyway.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 fellow Master 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! ]]> Tue 09 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37854/the-boy-jack-waters-chapter-2-the-appraisal/ https://www.anarchyporn.com/video/37557/apprentice-waters-chapter-4-the-covenant/
Master Napoli sits on a bed in a small attic room, handsome in his white suit. Master Kamp stands behind him, overseeing this most intimate of ceremonies. The two men are linked, either by blood or by some ancient rite. Apprentice Waters crawls subserviently into the space wearing a flimsy Grecian gown. He is instructed to wash Napoli's feet and does so with tenderness and erotic precision. Napoli pulls the boy to his feet and unties the single bow which keeps the scanty fabric together. It tumbles to the floor and the apprentice is left naked and vulnerable, but highly aroused with a rock hard penis. Master Napoli then begins to undress. He takes his time. He teases the boy, knowing how much the apprentice wants him. Apprentice Waters drops to his knees and adeptly services the master with his mouth, deep-throating him, expertly and without gagging. The apprentice is guided onto the bed where he is penetrated by the master's huge dick. Master Kamp suddenly enters the picture, gently stroking Waters' face as Master Napoli thrusts harder and deeper. A change of position finds Waters riding Napoli while Kamp jerks the boy's dick. Master Napoli holds Apprentice Waters, tightly wrapping his arms around him as both men inch closer to orgasm. Master Kamp kisses the boy passionately before seductively running his hand across Napoli's chest. It's a moment of profound intimacy. And then, just like that, Master Napoli explodes inside the boy, sealing the deal and creating the most perfect three-generational family. ]]> Tue 09 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37557/apprentice-waters-chapter-4-the-covenant/ https://www.anarchyporn.com/video/37727/the-boy-jack-waters-chapter-5-slave-boy/
I didn't tell Dillon what he could or couldn't do. He's my friend and I trust him. Jack is my slave and it's his duty to serve. I could tell Jack was surprised to see Dillon step out of the shadows, though. He's met him before and knows who he is. Still, Dillon showed him the key and told him that I had given him permission to use Jack and Jack obeyed.Dillon led him out of the cage and placed him on the platform in the middle of the dungeon. He opened his pants and pulled out his cock for Jack to suck. He was clearly pleased with Jack's performance. Jack is a damn good cocksucker and enjoys his work. Soon, both of them were moaning.Dillon seemed to be almost as taken with Jack as I am; stroking his soft skin, smelling his fresh young scent, fucking Jack's mouth with his cock. Dillon is hardly long enough to really choke a boy but what he lacks in length, he makes up for in circumference. When he drives it in the root, he sure can stretch a boy's hole and make him squeal. I was looking forward to seeing how Jack would take it ]]> Mon 08 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37727/the-boy-jack-waters-chapter-5-slave-boy/ https://www.anarchyporn.com/video/37839/apprentice-waters-chapter-1-the-interview/
He picked up a small black fabric bag and carefully eased its contents out. There was clear glass or plastic object inside which, rather suspiciously, was shaped like a penis. I instinctively knew that he wanted to push it into me and the thought was terrifying. It was three times the diameter of his finger and really not far off the size of my own penis. He sprayed the glass and my dick with a huge amount of oil before starting to push his finger into me again. My entire body erupted into the shakes. As predicted, he was soon pressing the penis-like object against my butt, slowly and patiently applying pressure until I felt my hole relaxing and beginning to open up. And then I felt it creeping into me. It hurt. It really hurt, but I felt my muscles gripping around it like a clamp and pulling it inside me. It was by far the most intense thing that has ever happened to me. And I was rock hard throughout. Harder than I've been in my life before. He started to rub my dick really hard. Up and down he went, sending me into a state of absolute ecstasy. I felt a prickling sensation in my balls which started to grow out of control. It was like there was a knot inside me which needed to be released somehow. My entire body went hot and began to tingle. And then it happened. A white liquid came shooting out of the tip of my penis, all over the Master's hand and onto my belly. I knew instinctively that I had orgasmed. And it felt real good. ]]> Sat 06 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37839/apprentice-waters-chapter-1-the-interview/ https://www.anarchyporn.com/video/37700/apprentice-waters-chapter-3-the-initiation/
The room was entirely white. So white, in fact, and so brightly lit, that it made my eyes sting. Master Napoli was sitting on a chair in the middle of the room, wearing the most beautifully-fitted white suit. He asked if I was ready to be initiated into the order and I told him I was. Then he dipped his finger into some kind of warm scented oil and started to gently touch various parts of my body. It was so calming, so sensuous. His fingers were like the softest feathers. The more he touched me, the more aroused I felt. My penis instantly sprang to attention, twitching and throbbing in anticipation. Master Napoli knelt in front of me and started to rub oils into my groin. The sensation was erotic beyond words. Then he began to suck me. It felt incredible. It all went so slowly. So wonderfully slowly. So stimulatingly, tantalizingly slowly. He pushed me down, encouraging me to lean over a footstool before pushing his tongue into my hole and allowing it to dance and flicker. I could feel my body opening up. I was ready for him and he could tell. He lined his giant penis up with my hole and then pushed it in. My God it was intense. We were one being. One sexual creature. One pulsing, gasping, unit of pure pleasure and I loved it. He went harder and faster and I could sense that he was about to cum. He pulled out, and, within seconds, I felt his beautiful, thick juices showering onto my butt cheeks. He pushed himself back into me, then, ceremonially, pressed semen into my forehead. I was finally and officially a member of the order. ]]> Thu 04 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/37700/apprentice-waters-chapter-3-the-initiation/