Page 50 of The Last One to Let You Down

“Yes, sir.” Tom wiggled impatiently. “I’m ready. Please.”

“Roll back over on your stomach and spread your legs,” Cypress said, lifting to allow Tom to get into position.

Tom hugged his pillows, groaning when Cypress used his knees to spread his legs further apart. He could hear him opening the lube, exhaling shakily when he felt the hot head of Cypress’s cock pushing up against his ass.

Cypress grabbed his tender cheeks, spreading them wide, using his hips to rub his cock against his hole. “Mmm, you’re so pretty, Tom… look at you, so fuckin’ hungry for it…”

“Yes, sir,” Tom said, not even trying to hide how excited he was. He couldn’t stop clenching, hoping he could somehow catch Cypress’s dick and make him press inside. The teasing was driving him insane.

After what felt like hours, Cypress began to push forward.

They shared a soft gasp, and Tom moaned as Cypress’s thick cock stretched him open. The first few inches slid in without much trouble, but it never seemed to stop. There was more and more until Tom’s hole was burning from the pressure, and he willed himself to stay pliant.

“Good boy,” Cypress murmured, rubbing Tom’s lower back. He pulled back at a leisurely pace before thrusting deep again—patient thrusts to work through the resistance of Tom’s tight hole.

Tom could feel himself loosening up, the discomfort receding as Cypress kept on. He moaned quietly when Cypress’s fingers played around his hole, feeling where his cock was stretching him open.

“Look at you,” Cypress praised. “You’re giving it up for me so nicely… your little asshole loves getting fucked, hmm? You like this? Being full of cock?”

“Yes, sir,” Tom said, not even recognizing the sound of his own voice. He was hoarse, breathless, and he gasped every time Cypress pressed in. “I love it… I love it so much…”

“Mmm, good. Because I’m gonna fuck you every chance I get,” Cypress promised, suddenly slamming his hips forward with a lusty grunt. “Mm, every fuckin’ day if I can.”

“Fuck!” Tom cried out without even meaning to.

Cypress’s only reply was to slam into him again, pressing a firm hand into the small of Tom’s back to hold him down as he started to pound him without mercy.

Tom was totally helpless, trapped beneath Cypress’s strong hold. He couldn’t move at all, groaning with every ferocious thrust. The sweet pleasure skirted right along the edge of pain, and he clawed at the bed to find relief from the intense sensation. He couldn’t do anything except lie there and take it, certain no one had ever fucked him like this.

Cypress was like a machine, relentlessly driving their bodies together over and over until all Tom could hear was the crack of colliding skin and his own desperate moans. He was so full, hot, and his body was aching from being used so roughly.He was loving each and every brutal second, and he couldn’t get enough.

His head was completely empty, his world reduced to Cypress’s cock spearing his body and nothing else. He gasped when Cypress plastered himself against his back and began to whisper the most deliciously lewd things in his ear.

“Your sweet little ass is gonna make me come soon,” Cypress said, hushed and excited. “You feel too fuckin’ good. Mmm, Tom… fuck, I’m gonna fill you the fuck up until you’re fuckin’ dripping… you want that? Mm, you want my load?”

“Yes!” Tom moaned, every word forever seared into his consciousness like a hot brand. He’d never wanted anything more, pushing his hips up to take Cypress as deeply as he could. He felt soloosenow, positively ruined, and he deliriously wondered how long he’d stay open once Cypress was done with him.

“Mmm, come on,” Cypress grunted, his thrusts starting to decrease in frequency as they increased in strength. “Come on, baby… here it comes… fuckin’ take it!”

There, fuck. Tom could feel Cypress’s cock swelling inside of him as he came, the immediate rush of heat making him shudder. He moaned as Cypress kept on thrusting, his cock effortlessly sliding in and out, slick with his own come.

Cypress gave one final slam, grunting low as he kissed Tom’s shoulder. “Oh, what a very, very good boy you are. You took it all.”

“Mmm, thank you, sir,” Tom murmured, his hole throbbing around the fat cock still stuffed inside of him.

Cypress pulled out, grabbing Tom’s hips as he said, “Come on. Up on your knees for me.”

“What?”

“Don’t you wanna come?”

“Yes, sir.”

“Then come on. Get on your knees. I want to see you. What I did to you.”

“Oh, God,” Tom whispered, shuffling up to his knees and keeping his head buried in his pillows. He could feel Cypress’s come dripping out of him, and he whimpered when Cypress’s fingers began to push back into him.

Tom’s hole was soft and wet, easily accepting two fingers. He couldn’t begin to imagine what a mess he was, and his face felt like it was catching fire. Cypress was scissoring his hole, spreading it open, and Tom moaned when he felt another trickle of come leak out.