Page 128 of The Last One to Let You Down

Moaning softly, Tom tried lifting his hips to chase Cypress’s taunting fingers. He got another hard smack in reply on his other cheek, causing him to cry out from the new flash of pain. Now, both of his cheeks were throbbing and hot, and he continued to grind his aching cock down to find some sort of relief.

“You want me to fuck you, don’t you?” Cypress asked, ever so smug because he obviously knew the answer.

“Yes, sir,” Tom pleaded. “Please. I’ll take all my spankings, I will, but please, fuck me first. I need something, anything.”

“Not yet,” Cypress warned, giving him another sharp smack. “Reach back here and help me spread your plump little cheeks. I wanna look at you.”

Tom was too far gone to be embarrassed, his hand joining Cypress’s on the opposite cheek to spread himself wide open. He had to reposition himself to keep from falling, wiggling his upper body up onto the bed and leaving his legs in Cypress’s lap, straddling his thighs.

“Good boy, now come on,” Cypress said, urging Tom’s legs apart. “There we go… mmm. You look good enough to eat.”

Tom could feel his heartbeat down in his cheeks, and his cock currently chafing on Cypress’s hip. He couldn’t imagine how lewd it looked to be spread out like this, weakly rocking his hips as he whispered, “Thank you, sir.”

Cypress squeezed Tom’s ass, his other hand coming down and smacking right on top of his hole.

Tom jerked in surprise, the pain reverberating down in his balls and up his spine. He couldn’t help how he clenched up, gasping when Cypress spanked him there again. “Oh, f-fuck!”

Cypress stroked his long fingers up and down between Tom’s thighs, pausing to massage his tender hole and sighing happily. “Mm, I love watching you squirm like this… ready for more?”

“Yes, sir, please. I need, I need something,” Tom begged. He was so hot and starting to sweat, whimpering when the tip of Cypress’s finger pushed inside of him.

“Mmm, almost.” Cypress gently pushed Tom up the rest of the way onto the bed. “Go ahead and make yourself comfortable and get on the pillows. I’m going to tie you down now.”

Clumsily, Tom rolled over and scooted up so he could rest his head on the pillows. His ass was still stinging, and even the smooth comforter beneath him felt too rough against his sensitive skin.

Cypress brought out the cuffs, attaching them to the bed and securing Tom’s wrists. He kissed his forehead, checking the fit and asking, “Good?”

“Yes, sir,” Tom replied.

“Now, let’s see how flexible you are,” Cypress said with a sly wink, lifting Tom’s legs and pushing them back toward his chest.

Tom had to spread his legs to accommodate the stretch, and he usually hated any position like this. It made his round belly fold up in a way he thought was very unflattering, but there was something about how Cypress was looking at him right now that made him not mind as much.

There was so much adoration in those big brown eyes, and it stole Tom’s breath away. No one had ever looked at him with such heat or desire, and he felt so beautiful.

“Stay like that for me,” Cypress commanded, reaching under the bed for something.

Lust made Tom’s stomach flip when he saw what Cypress was now holding a slick black riding crop.

“We’re going to start slow,” Cypress said, teasing the crop over his red ass. “Just a little taste to see if you like it.”

“I’m ready, sir,” Tom said, tugging impatiently on the cuffs. “Please, give it to me.”

Cypress cupped Tom’s balls, squeezing them tight as he cracked the crop over Tom’s ass.

Tom flinched, groaning out loud without meaning to. Despite only striking a small area, the sting of the riding crop was much more intense, and the welt left in its wake burned white-hot. He could feel fresh tears in his eyes, and his brain focused right in on the path the crop had taken across his tender cheeks.

The throb was incredibly deep, and Tom would have thought he’d actually been cut had he not known the source of this pain. “Oh, fuck, oh, oh, fuck me!”

Cypress pressed his fingers back inside Tom’s hole, giving him teasing thrusts as he asked, “Do you like that? Do you want some more?”

“Yes fuckin’ sir!”

Cypress snapped the crop over Tom’s thighs, his fingers pushing deeper.

The burn of his hole getting stretched and the crack of the crop made Tom moan from deep down in his chest. He could feel his legs starting to shake from holding himself in this position and the sweet adrenaline pumping through his body.

The crop whipped across his thighs again, and Tom was ready to sob. He could feel each individual lick pulsing, and he pulled at the cuffs as hard as he could to create some sort of counter pressure.