Jacob sat at his desk still, his chin resting on clasped hands. His face remained unreadable as Troye entered the room, closing the door behind him, "Come show me what you chose." Troye's legs wanted to shake as he approached Jacob, holding the lube and plug out to his Dom. Jacob smiled at Troye's choices, nodding slowly. Troye swallowed hard, "I almost went with the glass but-" "Strip." And Troye was hard, just like that. Jacob's dominant tone did something to the submissive nature of Troye. The boy all but dumped the lube and plug onto Jacob's desk so he could begin stripping from his clothes.

He'd put on a simple pair of silky black panties, pink lace lining Troye's hips and thighs, and the panties were quickly the only thing between Troye and nudity as he stood shyly in front of Jacob. They weren't much, however, and Troye's erect cock poked pink and lovely out of the top. "T-These too?" Troye croaked. "Are you alright with that?" Jacob momentarily made sure. "If you're okay with this-" "I'm okay with anything," Troye said immediately. "Strip, all the way," Jacob commanded. "And then I want you to put lube on your fingers and open yourself up. I'm not going to help because you interrupted me. Good boys don't interrupt." Troye whined, stripping from his panties and kicking them towards his clothes pile before grabbing for the lube.

He looked to Jacob pleadingly for directions, rubbing at his hips a bit self-consciously, "Where do you want me to...?" "Put one leg up here," Jacob requested, patting his own thigh. "But I want to be able to see." Troye was shaking a bit as he propped one leg up on Jacob's leg, having to grab onto the arm of the chair with one hand for balance. The lube had a pump rather than a cap, and Troye pumped a few squirts into his hand and spread the substance across his fingers. Mentally he was attempting to prepare himself, thinking, I've fingered myself before, the only thing difference this time is an audience. And yet Troye's audience made everything seem so much more sensitive. The simple brush of his slick fingers had his hole fluttering and legs trembling a bit.

"Sir," Troye breathed helplessly. "Open yourself up." Troye slipped a finger in all the way down to the bottom knuckle, whimpering and curling his finger a bit. He was trying to avoid his prostate, because he was already so unbelievably hard that he feared he'd cum embarrassingly before Jacob wanted him to. Troye prodded his finger in and out, leaning a bit and clutching onto the armrest of Jacob's chair, "M-More?" "Add a finger," Jacob approved. Troye pulled out his single finger before gladly stuffing his middle and index back, pumping them in and out of himself dizzyingly. The pleasure came in sharp bursts, and it was almost too much.

It'd been such a long time and his dick was so hard in front of him. He couldn't stroke it, if he removed his hand from the armrest his shaky legs would collapse, so he continued to pump his finger in and out as he trembled and whined. He could feel Jacob's gaze on him the entire time, and Jacob's voice was low when he spoke again. "Add another finger." Three fingers in and Troye couldn't even consider keeping quiet. He was gasping out in high whines, wanting nothing more than for Jacob to help him. His wrist cramped and he couldn't seem to get the right angle. It was good, but it wasn't enough, "Sir, please, touch me, I can't-" "That's enough," Jacob said firmly, but his voice was rough with arousal. "You're going to put the plug in and put your clothes back on now."

"What?" Troye gasped. He was already so needy, he wanted to cum. "Troye," Jacob said warningly, but Troye gave a choked whimper and reached for the plug. He squirted a few pumps onto the toy before craning his arm back again and lining the toy up to his entrance. The stretch was a bit more than the burn of three fingers, and he gasped sharply as he continued to press in past the widest girth of the plug. The flat silicone bottom nestled firmly against Troye' bum, and he shakily tried to straighten up. His movements nudged the plug around inside him, making it brush his prostate. He nearly collapsed, having to cling to Jacob's legs so that he wouldn't topple to the ground.

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