by K. L. Hiers
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.
“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 were doing something 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 could feel so 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, an
d 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.
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 he did feel 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 am worthy.”
“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.
Cypress used the heel of one hand to pin Tom’s cock against his stomach and confirmed his suspicion. “Are you ready?”
“Yes, sir.”
“Repeat after me. I am worth loving.”
Tom inhaled slowly, licked his lips, and said firmly, “I am worth loving.”
Cypress immediately brought his other hand down, popping the underside of his fingers across the shaft of Tom’s hard cock.
Tom yelped, stunned by how unforgiving the sting was, and he moaned as the tender skin there throbbed.
“Well?” Cypress raised his hand.
“I am worth loving,” Tom weakly replied, cringing as he prepared himself to be struck.
Cypress spanked Tom’s cock twice in rapid succession, keeping his heel firmly at the base.
“Oh, fuck! Fuck!” Tom groaned, his back curling off the bed and bucking up against Cypress’s hand, desperate for any friction to counter the pounding in his cock. He clenched around the plug and moaned again. “Fuck.”
“I am worth loving,” Cypress repeated.
Tom closed his eyes, hot with tears, and tried to focus. Beyond his physical appearance and skills, he had so much to give. He was tired of one-sided affairs where he invested everything he had and barely got pocket change in return.
He deserved a relationship with someone where they would take care of each other and lift one another, challenge and encourage each other and build something to last a lifetime.
He deserved someone to love him back as much as he would love them, and all his previous partners’ inability to provide that was merely a reflection of their insufficient value.
Not Tom’s.
“Tom?” Cypress pushed again.
“Yes!” Tom cried passionately. “I am worth it! I’ve always been worth it! Always!”
“Yes,” Cypress hissed triumphantly, surging forward to kiss him. “My good boy, yes. That was perfect. So fucking perfect.”
Tom kissed back fiercely, groaning loudly as Cypress removed the plug. He was empty and wet, but Cypress’s cock was right there, gliding inside silky smooth, and Tom sobbed in relief to be filled once more.
He needed movement, something, anything, and he begged, “Please fuck me! Cypress! Fuck me, God, please!”
Cypress took him fast, hard, a brutal pace that ended with Tom’s legs up on his shoulders and him screaming Cypress’s name until he came inside him and finished Tom off with a few quick pumps of his hand.
As they both drifted back down from the heights of bliss, they held each other close and traded breathless kisses.
“So,” Tom panted. “Cock spanking. That’s a thing.”
“Did you like it?” Cypres
s smiled happily.
“Very much.”
“Just wait ‘til I bust out my riding crop.”
“Oh, ha ha, very funny.” Tom rolled his eyes, but then he realized Cypress didn’t appear to be joking. “Wait, are you serious?”
“Mmhmm.”
“Oh, fuck.”
Cypress assured Tom they were a way off from riding crops and briefly left the room to get what he needed to clean up.
Tom remained sprawled across the bed, his heart still thudding pleasantly from the force of their coupling. He felt fantastic. His ass was sore, his cock stung, and his legs were two limp noodles. He could feel a lingering blush in his face and his chest, and he couldn’t stop smiling.
He couldn’t resist reaching down to feel his hole, wondering if he’d still be open after wearing the plug for so long. He was almost disappointed he’d already started to tighten back up but still couldn’t resist slipping his fingers inside to test the tender tissue, like toying with a fresh bruise.
Damn, that had been intense.
Cypress returned with a hand towel, warm and damp, reverently rubbing Tom down. “How are you feeling?”
“Great,” Tom said. “And mm, not that I’m really complaining, but are you always going to clean me up?”
“It’s my job,” Cypress replied, sliding the towel gently between Tom’s thighs. “It’s part of our aftercare.”
“Aftercare?”
“After a scene like that, it’s important to make sure you’re okay,” Cypress explained. “Scenes aren’t like sex. We talk about what we’re going to do, we plan for it, and afterwards, we talk some more to make sure we’re both okay. Physically and emotionally, the things we do together can take a lot out of you.”
“No shit.” Tom laughed.
Cypress smirked.
“I’m good. Really. Just a little sore.”
“That’s your body. What about your mind?”
Tom honestly didn’t know how to answer. He was deeply satisfied from some amazing sex, and he was trying to find a way to explain what was going on in his head.
“Nothing,” he said at last. “I’m… I’m calm. I’m happy. I’m…” He took a moment to gather himself, saying finally, “I’ve been spending too much of my time settling for what’s convenient instead of what I deserve, well, because I’m lonely.”
