Disciplinary Action | APPRENTICE RYAN | Chapter 3

A boy’s sexuality is irrelevant to the Masons. While many acts of homosexuality occur, it is often the case that the leaders and initiates live very different lives outside of the order. For some, the idea of being with another is part of what keeps them dedicated and committed to the secret society. For others, it’s a fair exchange for what the brotherhood provides.

Occasionally, a young man will come through with an apparent same-sex attraction, but struggling to determine if this is right or wrong. For the Masons, this provides a fertile opportunity to test the boy’s determination and drive. Getting inside the head of a young, impressionable apprentice is what every master dreams of. And today, Grandmaster Oaks continues to dive into Apprentice Ryan’s mind.

When the order came for Apprentice Ryan to receive disciplinary action, he did not question it. He’d been trying to hide his attraction to men in general, but being around the silver-haired daddy proved too much for his carefully constructed denials. Grandmaster Oaks was stunningly handsome with a powerful charisma that cut deep into his core. Ryan didn’t feel like he could hide anything from him.

Grandmaster Oaks enjoyed seeing the young man squirm. His struggle was something he liked to tease out and play with. Not only did it make Ryan’s arousal all the more decadent, but Grandmaster Oaks knew he could use it to keep the apprentice submissive and receptive to any instruction he was given.

The temple lodge was empty at night, giving Grandmaster Oaks the perfect opportunity to give Apprentice Ryan the kind of discipline he needed. Assisted by Grandmaster Angus, the two were powerful, commanding figures that could turn Apprentice Ryan into a scared little boy with just their presence. The young man entered the dark, private room as he was told, steeling himself for what was to come.

Grandmaster Oaks sat on a large, red chair with a high back and arms. It looked like a throne, which made Oaks resemble a king as he sat tall in his suit and tie. Angus stood behind him and to the side, arms crossed in front of him, eyeing Ryan as he made his way to the seated master.

Oak ordered the young man to drop his pants. Ryan did as he was told, nerves shaking his hands as he fumbled with his zipper. With his pants down at his ankles, Oaks pulled him forward and placed him face down on his lap.

His crotch rested against Oaks’ leg and his ass hung over, exposed and vulnerable. Ryan knew this position. He’d experienced it many times growing up. But it had been years since he was bent over someone’s knee to be punished.

Oaks wasted no time. His hand slapped down on Apprentice Ryan’s ass, giving him a sharp, sudden jolt of pain that worked up through his spine to the base of his skull. It was quick, but it was effective in getting Ryan’s full attention. All the boy could think about was his ass being spanked, waiting for the next hand to strike and the resulting rush of pain.

The spanking continued with the raps coming faster and in higher frequency. Soon, he felt like his ass being pelted with needles, stinging his flesh again and again. It was amazing how the body seemed to make it worse over time rather than try to soften the blows. Ryan could hardly think about anything but the pain he endured. Not even that his cock was growing hard and rigid up against the older man’s thigh.

Grandmaster Oaks could feel the boy’s excitement growing. In fact, he counted on it. He knew the best way to make a boy feel like he deserved punishment was to make him feel like he was the cause of his own transgression. And for a boy who thought being attracted to men was the ultimate sin, getting him hard was simple and delightful.

Playing with his head, Oaks told him that he wasn’t meant to enjoy this, that he was being punished for his behavior and thoughts. He stood the boy up, unable to hide the devilish grin on his face at the sight of his erection. He pulled it out, teasing it in his hand, as if pointing at it as the cause of his punishment.

Grandmaster Oaks ordered Ryan to remove the remainder of his clothing, leaving the boy completely exposed and open for more abuse.

Oaks bent Ryan back over his knee, impressed by the already present red glow that emanated off his smooth, pale butt cheeks. The older man had given him a good color, but he was far from done.

Taking a paddle from his fellow master, Oaks ran the cold, smooth surface of the wood against the warm welt on the apprentice’s behind. It felt comforting and cooling at first, but Ryan knew this was not meant to make things better.

Ryan gripped Oaks’ far leg, holding onto it for support as he braced himself for more punishment. He felt deep down down that he deserved it, but he also found himself incredibly aroused by it. In a weird, confusing way, his denial of his sexuality only made his desire even stronger. He wanted Oaks’ to tease him, touch him, even fuck him.

Oaks gave Ryan a session with the paddle, watching his body flinch and twitch every time he readied himself for a smack and after it was received. Seeing the apprentice’s ass shake in response made the older man feel powerful and strong. It also made him hungry to see what more the boy’s ass could take.

Grandmaster Oaks turned Ryan upside down, resting him on his head with his legs and hole up toward him. It was an awkward, uncomfortable position for Ryan to be in, but it gave the older man unfettered, easy access to his hole. And ultimately, that’s all that mattered.

Taking out some of his favorite toys, Grandmaster Oaks took pleasure in opening up the boy’s hole, getting it wet with oil and sliding his phallic objects inside. As he did, Ryan’s throbbing hard cock hung down towards his face like the sword of Damocles, threatening to rain down his own juices as he got more and more aroused.

Oaks told him to touch himself, something Ryan was desperate to do, but nervous about what more Oaks would put inside him. As the boy worked himself closer and closer to climax, Grandmaster Oaks proceed with great delight in filling the boy’s hole, pushing a large, graduated plug deeper and deeper into his anal cavity. The knobby black object pushed hard against Apprentice Ryan’s prostate, making him leak pre-cum onto his chest and face.

Ryan felt exposed and humiliated and completely out of control… and he loved every second of it. He tried to hold out as long as he could, not wanting the moment to end. He knew that once it was over, he was going to retreat back to his confusion and frustration, battling his inner urges and trying to live up to the rest of society. But here, in that room, on the edge of climax, Apprentice Ryan could be as sexual and horny and hungry as he wanted to be… and Grandmaster Oaks would tell him to go further.

He locked eyes with the older man, hearing his encouraging words and seeing his mischievous smile. It was too much for him to take, and a jet of watery white liquid sprayed out of the end of his cock and all over his face. It was wild and intense, and Grandmaster Oaks couldn’t be happier to see the boy in such ecstasy...