In the Interview of Apprentice Oliver James for MasonicBoys, Legrand Wold test the new stud. He finger fucks his ass and sucks him off. 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…
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