I’ve taken a keen interest in Apprentice Land ever since his arrival. I could tell from the moment I saw him that he was special. Pale-skinned, red-cheeked, well-mannered, compliant and always impeccably turned out, he’s been a joy to mentor. His atonement ceremony promised to be memorable. The other Masters were lining up to oversee it, but in the end Master Weston and Master Figata’s seniority won out. Having single-handedly brought the boy this far, I was slightly irritated that Master Weston was given the honor of leading the proceedings. I find it difficult to play second-fiddle to anyone, even those who outrank me. As the boy walked nervously into the darkened chamber, I felt an overwhelming sense of frustration. He looked so cute all dressed up in his sexy little shirt and tie that the idea of not being able to sink my big dick into him again felt almost cruel. He stood in front of us shaking, head lowered. He instinctively knew that this ritual would end with his punishment. Master Weston ordered Master Figata and me to remove the cloth which was covering the bench in the middle of the room. It’s always a great privilege to watch the look on a boy’s face when he realizes what’s underneath. Dildos (or pegs, as we call them) of increasing sizes are attached to the bench along its length. The penny often takes a while to drop, but usually within a few seconds the boys would realize they are going to be required to ride the dildos, one by one, starting with the smallest and slowly working their way up to the last. The entire ritual is set up to push a boy to his absolute limits. It’s a vital part of his training. Some boys try to take it nonchalantly. Others simply go pale, instinctively concluding that the exercise is almost certain to end in failure! Master Figata was given the task of preparing the boy. He’s a tall man and he towered over Apprentice Land, slowly and sensually removing the boy’s clothes starting with the tie. I’ll confess: it was a deeply erotic sight. I’d always had a soft spot for Master Figata. He epitomized authority and masculinity. Watching him at work was a privilege and it was unsurprising that the boy responded so well to the touch. Master Figata then oiled the boy up, making his pale, naked flesh almost shimmer in the candlelight. I longed to slide my hands across the Apprentice’s torso and glide my dick over to those hot ass cheeks, but my duty that day was merely to observe. Figata finished his work and sat down, leaving the boy’s dick as hard as a rock. Master Weston instructed Apprentice Land to then stand at the head of the table before ordering him to lower himself down onto the smallest of the pegs, which had been pre-lubed. The boy did as told. It was immediately clear that he was deriving a great deal of pleasure from the peg. He stared into Master Weston’s face as he rode it. The young Apprentice made his way along the line of pegs, moaning with just a little more intensity every time he lowered himself onto one of a larger size. Master Figata occasionally felt obliged to assist the boy by pushing down on his shoulders. The boy continued to stare into Master Weston’s eyes, losing himself in the commands, plainly imagining he was riding the Master’s dick. The second-to-last peg is noticeably larger. Taking it requires courage, tenacity and very deep breathing. Apprentice Land lowered himself down and the peg slowly disappeared into his ass. He made a low, long, hollow sound as it tore into him, but he was determined to take it and his rock-hard dick told us that he was finding the experience enthralling. His eyes rolled back in his head and his face flushed bright red as waves of lustful energy surged through his body. I prepared the final peg, which was fat and round. It’s very differently shaped to the others and it’s one which no boy has yet managed to take. I was impressed that Apprentice Land even tried. And boy did he make a really good shot of it, splaying open his hole in an almost desperate attempt to get the peg inside him. For a split second I thought he was going to succeed… but it defeated him, just as it defeated every Apprentice who’s attempted to take it. Master Weston suddenly stood up—quite threateningly I felt—and removed his jacket, intimidating the nervous boy with his impressive height and bulk. Master Weston began to remove his clothes, never taking his eyes off the Apprentice. Master Weston then ordered the boy to turn around and squat over the table. Moments later, the Master pulled his big, thick dick out and casually thrust it, raw, into the Apprentice’s ass. Within seconds he was fucking Apprentice Land with deep, fast strokes and the boy was moaning and gasping in a trance. I wanted to be the one penetrating that beautiful butt. That said, I admit that Master Weston looked pretty awesome as he banged the boy, his big mature nipples bursting invitingly out of the thick wiry hair on his stocky chest. Master Figata stood, unzipped his trousers and fed his dick into the boy’s mouth. The boy sucked him as well as anyone could who’s being rutted frantically from behind by a horny, powerful ape of a man. Master Figata slowly undressed as the boy continued to suck him. It was clear that Master Figata was taking great delight in watching Master Weston wreck the Apprentice’s hole. Master Figata periodically leaned over to squeeze the hung Master’s huge nipples. Master Weston suddenly nutted very deep inside the boy, filling him with several huge rounds of the slippery stuff. As he pulled out, it squirted out with force. Apprentice Land then started to jerk himself and exploded all over one of the pegs, which, it struck me, would make an excellent form of lubrication for the next boy! It was a very beautiful moment, which capped off a textbook ceremony. This tenacious, handsome, brave boy is destined for greatness and I am only sorry that I’m unlikely to be able to play an active part in his ongoing development. I begrudgingly acknowledge, however, that he’s in a safe and sexy pair of hands.
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Date: November 13, 2023
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