Page 144 of Hard Earned Cash


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“As I said, I’m eager to reward you, but I also have to punish you,” Cold said, squeezing Jimmy’s hips. “It’s going to take some time for you to appreciate what I have planned, so it’s a very good thing we have all night.” He smiled. “Just the two of us.”

“Yes, sir.” Jimmy’s cock was growing from the anticipation.

“I want you to get ready for me,” Cold said, nodding at the bedside drawer. “Open up your hole for me, nice and slow.”

Jimmy reached inside to grab a brand new dildo and some lubricant as Cold moved to stand at the foot of the bed to watch. He stretched out with his head on the pillows, parting his legs so Cold could see.

He was already lubing up the toy when Cold chided, “Ah, ah. Use your hands first, Mr. Poe.”

Taking a deep breath, Jimmy nodded. He squirted the lubricant on his fingers, reaching down to rub over his hole. He was so eager to get going, to be fucked and used, but he had to slow down.

He had to be good.

Jimmy circled the edge of his asshole, letting it get wet but still not pressing inside yet. He used his other hand to reach down and massage his taint, his cock flexing from the precise attention.

“Good boy,” Cold murmured, his icy gaze unmoving.

Jimmy moaned softly at the praise, and he finally let the tips of his fingers push in. He moved in and out, feeling around the tight muscle and encouraging it to relax.

He got lost to it, wrapped up in the gentle tug of his own hand as he worked his fingers deeper.

“Go on,” Cold urged. “Give yourself a little more...”

Jimmy slipped his fingers in as far as he could, hooking his arm around his leg and bringing his knee to his chest. “Mmm... sir...”

“Does it feel good, Mr. Poe?”

“Yes,” Jimmy sighed, holding his fingers in and grinding on his hand. “Mmm, but I want more... I need more, sir.”

“You want the toy now?”

“Yes, please!” Jimmy replied urgently. “I can take it so good, please! I’m ready, sir!”

Cold was considering it, waiting several long moments before he said, “Go on, Mr. Poe. Show me.”

Jimmy snatched the dildo up immediately, having to remind himself to take his time before he did something to anger Cold. He had to do this right. He had to be good.

Keeping his leg tucked against his chest, Jimmy positioned the tip of the dildo up against his hole. He pushed in, inhaling sharply when he felt the unyielding pressure of rubber and his body’s initial resistance.

He waited patiently, groaning in relief as the toy slid in a few inches. He pulled it back and pressed in again, the friction reduced by the slick film of lubricant. He could feel his body swallowing it up, the toy moving deeper and deeper.

Jimmy gripped the end of the dildo and started a steady rhythm, closing his eyes as he rocked down on the toy. He was getting loud, gasping, and he knew Cold was watching him intently.

He couldn’t help it, trying to resist the urge to move faster, but it felt fantastic. His hand sped up, and he bit down on his knee as he fucked himself. He bottomed out with the toy over and over, wearing his teeth into his leg as he moaned.

“Stop,” Cold ordered.

“Mmmph!” Jimmy whined, but stilled his hand.

“Greedy little thing,” Cold tutted as he walked around the side of the bed.

“Sir?”

“Couldn’t wait for my cock. Just had to fuck your little hole, hmm?”

“It felt good, sir,” Jimmy pleaded. “Please... I... I was just trying to get myself ready for you!”

“Pull the toy out,” Cold commanded. “Let me see what you’ve done.”