Page 68 of The Last One to Let You Down

“Good?”

“Mm, good,” Tom breathed, letting the bed take his full weight now. He was sinking down into the soft fabric, and although his cock was hard, it wasn’t an immediate concern. Being touched felt good, and he let out a small sound as Cypress’s finger smoothly pushed inside of him.

Cypress thrust a few times before easing a second finger in beside the first, pushing in slower to give Tom time to adjust to the added girth.

It was all so gentle and slow, and Tom could feel himself opening up. The wet sounds of Cypress’s skilled fingers seemed to sync with Tom’s panting, and he moaned quietly, his toes curling into the rug beneath his feet.

Cypress pushed right against his prostate and rocked his hand in small circles, creating the most delicious pressure as it stretched the full circumference of Tom’s hole.

“Oh!” Tom cried out without meaning to, his hips jerking in surprise.

There was a smile in Cypress’s voice as he crooned, “Do you like that?” He removed the direct pressure for a moment, teasing around Tom’s prostate for a few seconds before pushing back down.

“Ah! Yes!” Tom moaned. “Yes, yes, yes… oh, Cypress… mmm…”

“Have you ever come like this, Tom?” Cypress asked, shifting back to direct pressure.

“No.”

“Oh, lucky me.”

“Mmph.” Tom could feel he was leaving a wet spot on the bed despite his cock only being half hard, but he could feel a distant pressure building.

“Patience is key,” Cypress said. “Relax. Take deep breaths. Let it wash over you. Focus on that good feeling and breathe for me.”

Cypress kept saying soothing little things, but Tom didn’t really hear him now. Time had slowed down to a tantalizing crawl, each breath took an eternity, and Cypress’s fingers never slowed. The pressure was growing stronger, and the alternating strokes and direct palpations of Cypress’s touch weredoingsomething to him.

Even though he couldn’t understand Cypress in this strange haze, Tom used the distant sound of his voice as an anchor. He stayed relaxed, remained calm, and breathed through the cascading sensations that made him want to sob.

He could feel himself twitching around Cypress’s fingers and deep inside of his loins. The tension was growing more rapidly now, and he was warm. He couldn’t tell if his dick was hard or soft, but he couldfeelso much, and the trembling was now radiating down his legs and up his spine.

“Cypress,” he croaked, his voice cracking.

“Come on, Tom,” Cypress urged. “I can feel you… you’re almost there. You’re such a good boy. My very good boy.”

Tom heard him clear as a bell, and the praise created a shiver that snuck down his body to where Cypress was stroking inside of him so relentlessly. The pressure came over him like a tsunami, and then suddenly released, and Tom felt the most intense waves of pleasure shaking him to his very marrow as he came.

He howled, he cried, he laughed deliriously—the feeling didn’t stop. It was too much and perfect, and Tom thought he was going to pass out. He’d never come like this, never for this long, and all he could do was blissfully sob, “Yes, Cypress, yes, fuck, yes!”

Cypress’s fingers finally began to slow and released Tom from his orgasmic prison, pulling out gently. “Mmm, there. How was that?”

Tom was pretty sure if his body slid back even so much as an inch, he would melt right down onto the floor in a puddle. He gave a thumb’s up, and Cypress draped himself over his back to kiss his shoulder.

“Good boy,” he whispered.

“Thank you, sir,” Tom said when he was able, still feeling little twitches and shudders. “Thank you so much.”

“Toys are much more effective,” Cypress said, “but mmm, I wanted your first one to be all mine.” He picked up the plug and slicked it up generously. “Breathe for me.”

Tom took a deep breath, preparing himself for an intense stretch, but the plug slid in easily. He could feel his hole involuntarily clench around it and bit his lip. It was a little strange, and he had the urge to push down, but the plug didn’t move.

“Spread your cheeks for me,” Cypress ordered. “Let me see.”

“Yes, sir.” Tom reached back to spread his cheeks, burying his face in the bed. He could feel Cypress tracing the base of the plug and arched up into his touch.

“Beautiful.” Cypress was smiling. “Come on. Now that we’ve worked on your patience, it’s time to work on your self-love.”

With Cypress’s help, Tom moved to the center of the bed. He stretched out on his stomach and rested his head down in the pillows. His muscles still felt fuzzy and strange, and any change in position made the presence of the plug inescapable. It created constant pressure, but it was tolerable when he was still.