Page 129 of The Last One to Let You Down

It was too much, too overwhelming, and he mumbled a prayer to whatever god was listening when Cypress eased his legs back down on the bed.

“My good boy,” Cypress whispered, kissing Tom’s flushed face and stroking his cock lovingly. “You did so well. You were such a good boy for me.”

“Thank you, sir,” Tom whispered back, worried his voice was going to crack. “Thank you so much.”

“We’re almost done with your punishment,” Cypress said, petting Tom’s damp hair. “Just one more little thing, mmm?”

“I’m ready, sir.” Tom watched as Cypress gently pinned his cock flat against his belly, and the hand holding the riding crop rose to strike.

He didn’t know how much strength Cypress had actually used, but when the crop hit his cock, he thought he was going to pass out from the rush. There was a stinging sensation like none he’d ever felt before, but it was followed by a flood of pleasure that nearly made his vision white out.

It almost felt like coming, but his whole body was trembling. He held onto the feeling for as long as he could, his hands going limp in the restraints, and he moaned loudly. “Ahh… oh, Cypress.”

Cypress bowed his head down, planting a loving kiss on the shaft of Tom’s pounding cock. “Mmm, good boy.” He smiled up at him. “Feeling good?”

“Yeah,” Tom wheezed out in reply, drawing in a shuddering breath. “Yes, sir, I mean. I’m good.”

“Now that you’ve taken your punishment, are you ready for your reward?”

“Fuck, yes, sir.”

“Wait here for me,” Cypress said, sliding off the bed and heading to the bathroom.

If Tom’s brain was fully functioning, he would have laughed. As it was, he was grateful he didn’t have to worry about breathing on his own as he continued to float on a blissful cloud. He felt sort of sleepy, and he couldn’t stop smiling.

He heard the sink running for a few minutes, and then Cypress came back out with a small, black, zippered case.

“These are for you,” Cypress said, sitting back down on the bed. He set the case down and grabbed a tube of lubricant from the bedside table. “If you don’t want to try it tonight, we don’t have to… but I can’t think of a better way to reward you.”

“What is it?” Tom tried to lift his head to study the case, but he had no idea what it could be.

“These are,” Cypress explained, pausing as he unzipped the case to show Tom the contents, “urethral sounds.”

There were eight in total, four fitted on each side in their own special elastic loops to keep them in place. The sizes ranged from a diameter that reminded Tom of the ink cartridge inside a ballpoint pen to one nearly as thick as his fingers.

“Oh, shit.”

“Uh huh.” Cypress picked out the smallest sound and offered it out to Tom for his inspection. “These have all been sterilized since the last time I used them, my hands are washed, and I’ve got plenty of lube. I need to know if you really want me to do this?”

“To… fuck my cock?” Tom blinked, unable to look away from the sound. It had seemed so small in the case, but it looked much bigger knowing it was potentially goinginsidehim.

“Yes.”

“Will it hurt?”

“It may be a little uncomfortable at first,” Cypress replied honestly. “There may be some burning as it’s going in. You have to be careful not to move or jerk around while it’s inside you because you could get seriously hurt.”

Somehow, the risk made this more appealing, and Tom was already saying, “Yes. Please. I want… I want it.”

“There’s my good boy.” Cypress seemed very pleased with Tom’s decision. He put the tiny sound away, picking up the one that was the next largest. “Now, we’re going to go nice and slow. You need to stay very still and don’t move.”

“Yes, sir,” Tom agreed eagerly. “I’ll be so very good for you.”

“I know you will be.” Cypress slicked up the head of Tom’s cock and the sound until they were both dripping. He got settled between Tom’s legs, stroking his cock until he was almost fully hard. “Take a few deep breaths for me.”

Tom closed his eyes, excited and terrified and turned on all at the same time. Feeling himself shiver so hard that his nipples stiffened, he looked down at Cypress patiently waiting for him. “I’m ready.”

“Good boy,” Cypress said, carefully inserting the tip of the sound.