Page 69 of The Last One to Let You Down

Cypress kneeled between Tom’s spread legs, running his hands over his thighs up to his ass. “I am going to give you some affirmations to recite for me. Do you understand?”

“And if I don’t sound sincere, you’ll spank me?”

“Oh, no.” Cypress chuckled. “I won’t spank you unless you do.”

“But… sir…?” Tom’s mind reeled.

“Pain isn’t always a punishment,” Cypress explained. “It can be a reward because the rush of adrenaline that it creates is quite enjoyable. The pain itself can be cathartic, a physical release for any emotional distress that you’re experiencing.” He rubbed his hands over Tom’s ass. “So, do you know what you have to do?”

“Yes, sir.” Tom’s mind had cleared somewhat, the drag of the alcohol cleansed by his intense orgasm. He had to be convincing if he wanted to be spanked—and God, finally admitting to himself that’s what he really wanted was its own victory.

“Now,” Cypress began, “repeat after me.”

“Yes, sir.”

“I am beautiful.”

“I am… beautiful.” Tom actually smiled. He was sweaty and flushed, his ass stuffed full with a thick silicone plug, and he could not stop smiling because hedidfeel beautiful. He could feel the ravenous way Cypress was looking at him and—

Cypress cracked his hand across Tom’s ass, a stinging flash of pain that made him gasp.

“Good boy. Say it again.”

“I am beautiful. I am so fucking beautiful—ah, fuck!” Tom cried out when the next slap made his back arch, and he clenched around the plug.

“I am worthy.”

“I am… I am worthy.” Tom closed his eyes, knowing that no spanking would be coming. He savored the lingering throb from the earlier hits and tried again. “I amworthy.”

“Why?”

Oh, Tom didn’t have the brainpower to do this right now. He whined, writhing against the bed as he panted, “I don’t know… because, because I’m beautiful?”

“Come on.”

“Because…”

“Come on, my good boy,” Cypress urged.

Another pain invaded Tom’s thoughts, but this wasn’t the pleasant burn of freshly spanked skin. It was an echo of the conversation they’d had before dinner, but now Tom knew exactly what to say.

“Because I’m talented. Because I’m smart. Because no one else can do what I fucking do. No one is as good as me, and they never will be because they’ll never care like I do. I’m worthy because there’s no one else fuckin’ like me.”

“What a very good boy,” Cypress purred, rearing his hand back and bringing it down like a hammer.

Tom moaned excitedly, the sting bringing tears to his ears as the warmth spread through his body. Another sharp spank made him whimper and had him dragging his hands over the pillows and holding on tight. He was getting hard again, his hips restlessly grinding against the bed as Cypress gave him another fierce slap.

Cypress was quick to rub Tom’s burning cheeks, giving him a little squeeze as he said, “You’ve been so very good for me, Tom. Such a very good boy.”

“Thank you, sir.” Tom was positively beaming. He could almost taste the wicked heat coming off his scarlet cheeks.

“Roll over for me. We have one final affirmation to recite.”

Lazily twisting his hips and willing the rest of his body to follow, Tom managed to flip onto his back. He groaned breathlessly from the plug moving as he did so, his cock standing right at attention as he gazed up at Cypress. “I’m ready, sir.”

“This last one is going to be the hardest, so I’m going to alter your motivations.” Cypress took off his underwear and straddled Tom’s hips. “If you are unable to say ‘I am worth loving,’ you will be spanked as a punishment.”

Even in this lusty haze, Tom was able to put two things together: one, it was going to be almost impossible for him to say in any manner that would convince Cypress, and two, Cypress was not going to spank his ass in this position.