https://www.anarchyporn.com/models/apprentice-james/ Wed 19 Aug 2026 07:34:47 +0200 https://www.anarchyporn.com/video/38463/apprentice-james-chapter-1-the-interview/
Master Legrand began to tie Oliver's hands behind the chair in which he was sitting. Oliver didn't know if this was a kind of ritual, but he patiently waited for the older man to tie the white rope around his wrists. When Master Legrand sat back down, he pulled his chair closer, bringing his long legs in on his own. The Master couldn't help but practically rest his knee on Oliver's loins, needing to get close enough to touch him.Master Legrand placed a hand on his apprentice's chest, feeling his heart beating through his new undergarments. The fabric was sheer, barely acting as a true cover. The Master ran his hand down inside it, feeling the boy's chest again. Oliver felt more uncomfortable this time. Being bound and restricted, he knew he wasn't going to be able to do anything. He watched as Master Legrand moved with long, slow caresses over his body, feeling his legs and stomach, teasing him and circling around his crotch until he couldn't take any more.Suddenly, Oliver felt the tip of his penis begin to lift up the fabric of his shorts, causing them to tent up in the most humiliating fashion. Oliver looked down, terrified. He looked back up at Master Legrand, but was surprised to see he was not at all put off. In fact, he seemed to focus his attention on his bulging member.Moving a hand inside the shorts, Master Legrand started to stroke the boy's shaft, working it gently between the tips of his fingers, exciting it but denying it the feeling of a full grip. Oliver couldn't deny that it felt good. He didn't want it to, but he couldn't fight his body's urges. He didn't know if it was simply the act of the touch that was doing it or if it was because the hand belonged to the handsome and powerful Master Legrand! Either way, he knew he was caught.The Master didn't stop, though. He seemed keen on seeing just how aroused Oliver could get. He began to tease the boy's nipples, play with his balls, even take a finger to Oliver's hole. Oliver had never been touched there before. It was tight and strong, but smooth and fleshy. Master Legrand ran his finger on the boy's sphincter in a circular motion, like he was playing with a button.Oliver felt it tickle a little then begin to slip inside him ever so delicately. He wanted to feel more. He wanted to take more. He breathlessly waited for Master Legrand to fully pierce his body and move inside him. He locked eyes with his Master, as if to beg him to push further. He couldn't bring the words to his tongue, but Master Legrand looked back, recognizing that desperation.With a slow, gentle push, the Master watched as his digit slipped inside Oliver, breaking him apart like he'd never felt before. The boy let out a gasp, in disbelief of what he was experiencing. Master Legrand took his free hand and began to stroke his apprentice's shaft, getting him worked up as he fingered his hole.Oliver began to pant, feeling himself getting close to climax as his prostate was poked. Master Legrand could see Oliver's reaction, not to mention the pulsing feeling of his heart in the tight ring around his finger. He wanted to see Oliver cum. And he knew this boy wasn't going to leave that chair until he did... ]]> Fri 12 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/38463/apprentice-james-chapter-1-the-interview/ https://www.anarchyporn.com/video/38424/apprentice-james-chapter-2-disciplinary-action/
Apprentice James felt the first peg enter his hole with a fiery sting. Sacrifice and hard work was part of every rite and ritual on the way to becoming a Master Mason. James knew this and accepted it.As Apprentice James eased himself down, Master Cox' face expressed something less than satisfaction. While James felt like he was pushing himself, Master Cox seemed to interpret this as merely the warm up.Nevertheless, when the older man ordered him to proceed to the next peg, the apprentice did so without hesitation. While he felt an intense heat around his ears and cheeks and a rapid pulse beating within his heart, he did what he thought was demanded of him.As he moved down the line, James felt himself becoming more and more acclimated to the stretching of his hole. But whenever it seemed like he was cheating the Order by not pressing firmly down against the bench, Master Fantana, a younger but equally handsome superior, stood beside him, ready to press down on his shoulders and ensure he was fully engulfing the object.Despite his resolve and determination to meet Master Cox' expectations, his virgin hole could only take so much. For not meeting the expectations of the Order, Apprentice James would have to face the consequences.The young man was placed on a large red altar with his legs held up by the younger master. He was clearly in a position to be fucked. He'd never experienced anything like that before, and now, in the dark with these strange men, he was going to have a once in a lifetime change.As Master Cox removed his pants, he saw the mustachioed daddy's hard, veiny cock sticking out from beneath his undershirt. Thinking of this man--the coach, the banker, the father, the husband, whoever he was in his real life--fucking him and filling him with his cock sent a thrill in his body.To his surprise and delight, the older man simply brought his bare cock between his cheeks and slid it deep into his body. And then that was that. Apprentice James was no longer a virgin.He looked up Master Cox, staring into the eyes of the first man to fuck him... and the powerful, commanding, masculine way his face stared back at him as he began to thrust back and forth... ]]> Sun 07 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/38424/apprentice-james-chapter-2-disciplinary-action/ https://www.anarchyporn.com/video/38399/apprentice-james-chapter-3-the-covenant/
Oliver did as he was told. Obediently, he stripped down completely and put on the ceremonial robe. It was big and loose hanging on his body, clearly not made for him. As he tried to balance it on his shoulders, he wondered how many others had worn this exact garment, and how many others had done what he was about to do.He'd barely spoken a handful of words to Master Cox, but already the older man had touched his body, handled his genitals, and even been inside him. Sex with him was part of the requirements of the Order, but Oliver did not mind.Crawling into the ceremony room on all fours, he lowered himself below the older man. Master Cox sat on the edge of a large bed, draped in a red altar cloth. Max Cox was dressed in all white, even down to his tie. Everything felt so formal and so ritualized.Master Cox stood him up, manipulating the material that hung over Oliver's body until it fell down around him. The boy stood naked, exposed and vulnerable, pressed against the fully suited older man. Oliver's cock began to stiffen, rising as he felt the moment of consummation approach.Master Cox took off his jacket, ordering Oliver to his knees. Within seconds, he pulled out his cock for Oliver to begin to suck. It was a big, thick, veiny member with a low hanging set of large testicles.Something about Master Cox just made him want to serve him. He felt it deep in his loins that he needed to be filled and fucked. He passionately and thoughtfully worshipped and sucked Master Cox's member, all the while anticipating the moment when it would be back inside his hole... ]]> Fri 05 Jun 2026 00:00:00 +0200 https://www.anarchyporn.com/video/38399/apprentice-james-chapter-3-the-covenant/