Page 30 of The Last One to Let You Down

“Yes.” Tom moaned quietly, rocking up into Cypress’s hand. Yes, a good boy. That’s all he wanted to be. He didn’t want to lie or steal anymore, he just wanted to be good.

“Yes, what?” Cypress prompted.

“Yes, sir.”

“Good boy,” Cypress said, pressing a light kiss to Tom’s lips. “Now, turn around and drop your pants. Let me see that cute little ass.”

Tom’s hands were weirdly numb as he reached down to untie the drawstring of his scrubs. No one had ever called his ass ‘cute’ before. He waited until he’d turned around to drop them, the light fabric pooling down around his ankles. He started to pull his underwear down, but Cypress gently nudged his hand.

“Not yet,” Cypress said, palming Tom’s round ass through his boxers. “We’re gonna start nice and slow with these still on. Okay?”

“Okay.” Tom braced himself against the counter, hands clamped down, and every muscle was wound up tight enough to snap.

“Mmm, relax.” Cypress draped himself over Tom’s back, his beard tickling Tom’s neck as he whispered in his ear, “Come on. Take a deep breath for me. If you’re tense, it’ll hurt.”

“Isn’t it supposed to?” Tom asked, inhaling shakily.

“Not like that. Not yet.”

Tom took a deep breath, his skin buzzing faintly. He took another as he tried to will the tension in his body to ease. He focused on Cypress’s hand on his ass, warm and firm, rubbing in lazy circles.

There, one more breath, and he was starting to finally—

Cypress’s hand jerked back and slapped Tom’s ass.

The force was enough to make Tom jump in surprise, and the quick tingle of pain tore a gasp from his lips. Cypress’s hand quickly returned to start rubbing where it had just struck, and Tom melted into his soothing touch.

The exchange of pain and pleasure happened so quickly that it made Tom’s head spin. His cock was painfully hard, and the lick of shame crawling up his back wasn’t enough to dissuade it. This was okay, he could enjoy it, it was gonna help him be good.

“Good?” Cypress asked quietly.

“Yes, sir. I want… please do it again.”

Cypress’s hand came down with more force, and God, Tommoaned. This one was hard enough to leave his skin stinging even as Cypress tried to rub it away, and he was overcome with a sweet rush of endorphins.

Again, Cypress spanked him.

Tom let out another loud moan, his hips unconsciously grinding into the counter to work off some of the building tension. “Oh, my God… fuck… Cypress.”

Cypress slid his hand inside Tom’s underwear, squeezing his bare cheek. “You’re doing so well, Tom. Such a very good boy. I think you’re ready for some more, hmm?”

“Yes, sir,” Tom replied eagerly, smiling as Cypress pulled his boxers down. He’d always been shy about his body, secretly wishing he could lose the youthful pudge from around his hips and his stomach.

He didn’t even like undressing with the lights on at home, and here he was, ass right out in the middle of Cypress’s flower shop. Maybe it was the way Cypress was groping him so greedily or the hungry gaze currently fixed on Tom’s backside, but Tom actually felt sexy.

He had never experienced a rush like this, an intense cloud of euphoria that was better than any lay he’d ever had. It was like coming, except he hadn’t popped off yet, and what he could feel building had the potential to be mind-shattering.

Cypress grabbed Tom’s hip and swung back, his hand snapping across his ass with a loud and satisfying smack.

The sound of bare skin colliding was fantastic, and the first real taste of pain made Tom’s knees buckle. He bowed his head down on the counter, breathing through the following throb. He could feel his pulse thudding away in his sore cheek and his dick, begging, “Yes, that, please, spank me again.”

Cypress growled, digging his fingers into Tom’s cheek before slapping his ass again. “There you go. Just like that. Good boy, such a very good boy.”

Tom’s hips hit the edge of the counter, his hands scrambling over the smooth surface for something to hold onto. He managed to grab the far edge, arching himself up. “I’m good,” he whispered, chanting it over and over again. “I’m good, I’m so good.”

Alternating between brutal spankings and gentle rubs, Cypress’s hands never quit moving for more than a few seconds. When Tom didn’t think he could handle another spanking, Cypress switched cheeks and began anew.

“You take it so well, Tom,” Cypress praised after a particularly hard smack made Tom cry out. “I bet you’d like it if I spanked your cock, too.”