Page 67 of The Last One to Let You Down

Their previous dates hadn’t left much room for chatting, and Tom was delighted they had so much in common beyond their intense physical attraction. They loved the same comics and superheroes, watched most of the same TV shows growing up, and even had similar celeb crushes.

There was an intense debate about who the hottest Chris was, and no clear victor emerged.

Cypress retrieved Mister Doodles’ food from Tom’s bag in the bedroom, which suspiciously looked like it had some sort of gravy on it when he fed it to her. Tom based this on the smell and the fact she actually ate it.

After helping clear the table, Tom took the wine and their glasses into the living room at Cypress’s request, sinking onto the sofa with a deep moan of satisfaction. He was grateful for the food in his belly to counter some of the alcohol, smiling as Cypress finally came to join him.

“And you’re sure you don’t want dessert?” Cypress asked, sitting down beside him with Mister Doodles clamoring around his feet.

“No, please, I’m so full,” Tom replied, patting his stomach. “I don’t think I’ll ever be able to move.”

“Mmm, that wouldn’t be so bad,” Cypress said, tilting his head in for a soft kiss. “I’ll just keep feeding you, and then you won’t be able to leave.”

“Ha! Mm, that might work.” Tom smiled, leaning against Cypress’s shoulder and reaching up to stroke his beard as they kissed. It didn’t take much for his heart to start racing again.

Cypress was gorgeous and kind, and Tom was still more than a little frustrated from their meetup in the bathroom. There was also a deeper layer to the attraction after talking together for so long. He felt closer to Cypress than he had to anyone else in years.

It was easy to give himself over and let Cypress control the pace, to control everything, and Tom grunted encouragingly when Cypress grabbed his hip to pull him up into his lap. The kiss was getting hotter and hotter, and Tom was not ashamed he was the first to say, “Bedroom?”

“Yes.”

The master bedroom was large but simply furnished with the exception of the lavish four-poster bed dominating the room. Everything was decorated in black and dark grays except the bed linens, which were a mix of various tones of reds and oranges.

Cypress led Tom in with an encouraging smile, asking, “Now, what’s your safe word, Tom?”

Tom was already buzzing before he even said it, replying breathlessly, “Calvarium clamp.”

“Undress for me,” Cypress said as he smoothly pulled his sweater over his head.

“Yes, sir.” Tom wasn’t as graceful as Cypress, but stumbles aside, he managed to strip down.

Cypress left only his boxer briefs on, the outline of his hard cock bulging through the thin fabric, and he brought Tom into his arms for a kiss. “You want to be a good boy, don’t you, Tom?”

“Yes, sir,” Tom replied immediately. “That’s all I want.”

“Tonight is going to be about patience and self-love. I’m going to show you a lot of things you’ve probably never done before. At any time if you’re not comfortable, do not hesitate to use your safe word.” Cypress held his chin firmly. “Do you understand?”

“Yes, sir.” Tom loved Cypress’s strong grip, the fog of his submission easing his already intoxicated mind. It happened so naturally that he should have been concerned, but he was only excited.

“Come on.” Cypress took him over to the bed, patting the comforter. “Bend over here for me.”

Tom obeyed, draping himself over the bed and arching his hips up. He wanted to be spanked, taken hard, and he eagerly awaited Cypress’s next move.

Cypress spread Tom’s cheeks, pushing his thumbs inward to massage around Tom’s hole. “I’m going to get your little ass ready for my cock. I’m gonna get you good and wet, stretch you out, might even let you come to help take the edge off.”

“Yeah?” Tom asked urgently. “And then you’ll fuck me, sir?”

“Patience,” Cypress reminded him. He continued to tease and rub Tom’s hole, slipping a hand away to reach into the bedside table drawer.

Tom looked back to see a tube of lubricant and the biggest butt plug he’d ever seen. “Is that… is that for me?”

“Mmhm. Bought it just for you,” Cypress said. “Once I’ve got you good and open. We don’t wanna lose all that hard work, do we?”

“No… no, sir.” Tom was nervous, but Cypress’s firm hands were soothing as they massaged his hips, and he began to relax. “Will it hurt?”

“No,” Cypress promised. “You should only feel pressure. If you feel pain, you tell me. Yes?”

“Yes, sir.” Tom sighed softly when he felt Cypress’s slick fingers sliding around his hole. Only the tip of one breached him, stretching, teasing, and he felt Cypress’s other hand push his cheek aside.