‘Sup With You, Dude?

The Next Step

© 2021

by

Jonathan Longhorn

If you have not read the original story ‘Sup With You, Dude? now might be a good time to do so. While this new piece could stand on its own merits, it might make more sense if you go back and read the original so you understand what’s going on.

Copyright © 2021 by Jonathan Longhorn (jonathan_longhorn at yahoo dot com). All rights reserved. Except for the use of less than two pages in any review, the reproduction or utilization of this work in whole or in part in any form by any electronic, mechanical, or other means is forbidden without the express written permission of the author. Express permission is granted to The Nifty Erotic Stories Archive for storage, indexing, retrieval, and display of this work.

Disclaimer: The material in this work is for mature audiences only and contains graphic sexual content and language. It is intended only for those aged 18 and older. All of the characters in this work are assumed to be at least 18 years of age.

This is a work of fiction. All names, characters, and settings are fictitious. Any resemblance to actual events, names, locales, organizations, or persons living or dead, is entirely coincidental. In the real world having sex without using a condom can be very dangerous to your health. Don’t ruin your life or your future. Slip it on before you slide it in.

All trademarks used in this work are the sole property of their owners and have been used without permission or endorsement.

Chapter 4

Reggie grinned in spite of his intense concentration; the tips of his fingers on his left hand registered an ill-contained ripple along Cayce’s spine. A soft whimper and moan indicated his friend’s need as he slipped a second finger into Cayce’s hole.

“You like that, bud?”

“Yes,” Cayce choked out. His own fingers dug the life out of the pillow beneath him. “Like. Yes. More. Please….”

Reggie chuckled softly. Cayce was hungry for it. Feverish for it. His friend was moaning and whimpering like a bitch in heat. He expected no less than an insatiable need for it after hearing his friend’s confession. Six months? Cayce had himself plugged nearly 24/7 for the last six months? Oh yeah. He had totally bottomed himself. Add that to the last six months of daily blow jobs? He was ‘so ready’ for the real thing buried in his hole. Pummeling it into submission. Filling it. Breeding it.

Hell, Cayce had probably turned himself into an insatiable cock whore.

Reggie stopped musing for a brief moment to dribble more lube down his fingers. He felt Cayce clench around his two fingers even as he began to push a third against his pucker. He slowly sank it inside that warm, moist, trembling canal to join its brothers.

And, Cayce moaned.

“Okay?”

“Yesss….”

Cayce lifted his butt and pushed back at the same time—trying to take more of his best friend’s fingers inside. He responded obediently to Reggie’s knee nudge; he spread his thighs wider apart.

Reggie’s eyes flicked to the nightstand. The butt plug lay there. And, the cock cage. He had wanted the cage off while he prepped Cayce for what was to come. He was discovering a perverted inkling in his little grey cells. He liked the sight of Cayce in that cage—his dick completely encompassed and locked in tight. He considered the fact that if Cayce had been wearing the cage as long as he had been keeping himself plugged then he might very well have set the cogs in motion to kill off his dick—turning it into a manclit more than a dick at this point.

Cayce’s manclit. He kind of liked the sound of that for some reason. He had kinks? Who knew?

Those thoughts made his rock-hard dick throb even more, if that was possible. Yeah, his dick was up and ready for this. He was going to totally fuck Cayce’s brains out and pulverize that cherry right out of existence.

Reggie couldn’t help but wonder—was he the right one for this? For Cayce’s deflowering? His first time being fucked? He was more than capable, not to mention very well equipped to do the job. But, would taking Cayce’s cherry cause a problem between them? Would it affect their friendship adversely somehow? Would Cayce … fall in love with him? Was that being conceited? The most important thing in this ‘situation’ of course was not ‘fucking Cayce’ but giving him what he needs. Taking care of him. Being there for him. Having his back.

“Cayce?”

“Hmm?”

“Are you sure about this?” Reggie wiggled his fingers slightly as he buried them to the second knuckle—again.

Cayce lifted up on his elbows and glanced over his shoulder even as his butt pushed back against those probing fingers once more.

Those … incredible … probing … fingers….

“Sure about…. Oh. Oh. Fu…. Oh yesss,” he groaned as one of Reggie’s fingers edged his nut button. “Sure … about … what?”

Reggie smirked at Cayce’s reaction to the finger plunge and wiggles. It was cool—hot as fuck kinda cool—that he could make these moans and gasps and whimpers escape from the mouth of his stud muffin total jock cop best friend.

“Are you sure you want me to pop your cherry?”

Cayce stiffened. He looked back over his shoulder. Searching. Trying to read Reggie’s expression.

Fuck. He doesn’t want to fuck me. Shit.

“You don’t … mmm…. You don’t … want to … fuck me?”

Reggie’s eyes rolled. He was afraid Cayce would read the question the wrong way.

“Turn around. Let’s talk,” Reggie said with a slap to Cayce’s left butt cheek. His rock hard. Cut from marble butt cheek.

Cayce’s head dropped onto the pillow for a moment as the air sizzled through his clenched teeth. Another involuntary hungry whimper followed when those three long, probing fingers pulled out of his hole. He turned—slowly. Was he sure about getting fucked? The resounding slap of his plump but not hard cock against his abs was evidence enough of that, wasn’t it? His eyes widened as he took in the sight of Reggie’s intent; his best friend’s cock stood tall and throbbing, drooling precum. That deliciously thick and creamy precum that he had tasted every day for the last six months.

Cayce squirmed into the mattress beneath him. He avoided making eye contact; slim chance that would mask his disappointment. Reggie didn’t want to do this? Yeah, letting Cayce blow him—every day for six months—two hundred and thirty-five times, including several multiple blows-a-day since he expressed his curiosity? Yeah, that was one thing. What straight guy in his right mind would turn down an offer of free, no-expectations or high maintenance blow jobs? But, asking Reggie to fuck him? To ‘officially’ pop his cherry?—no offense to that amazing vibrating butt plug, mind you. That was rather presumptuous on Cayce’s part; he had to admit that as much as he didn’t want to. Reggie was straight, after all.

“Look at me,” Reggie said as his left hand drifted across Cayce’s perfectly mounded pecs and then slid over the ripples of his abs. Cayce looked everywhere but into Reggie’s eyes. “Look … at … me.”

Cayce inhaled deeply as he tried to calm his nerves. At the same time, he tried to swallow the mounting dread that Reggie was having second thoughts.

“Cayce!” Reggie felt his friend jump beneath him at the harsh shout out. “Look … at … me!”

Reggie laughed. He couldn’t hold it back.

“What?”

“You’re adorable when you pout.”

Cayce’s face flushed.

“I don’t pout,” he argued even as his lower lip protruded.

“You are ‘so’ pouting,” Reggie teased with a gentle slap to his friend’s cheek.

“Why did you just have three fingers buried in my butt and tickling my prostate if you don’t want to fuck me?” There. That was ‘not’ pouting. That was ‘challenging’. Yeah—‘challenging’. ‘Not’ pouting. “I mean, if you didn’t want to do this, why did you….”

Reggie’s eyes rolled. Again. His buddy was ‘so’ pouting. ‘So’ adorable. Big, bad, tough guy cop. Pouting so hard his lip might break off.

“Oh, I’m gonna fuck you, Cayce. I’m going to fuck you and breed you,” Reggie said as he reached down to grab his throbbing cock. He gave it a few gentle strokes. “See how hard I am? ‘This’ is hard for you. ‘This’ should be evidence enough I am going to fuck you.”

“But you just said….”

“I said,” Reggie interrupted. “I said, admittedly not very clear of my intent, if you are sure about this. Meaning, are you sure you want me to be your first? Are you sure you want me to take your cherry? Maybe you would rather Mike be the first to fuck you? Or, maybe my brother, Beau to pop you open? You might run the risk of falling in love with me if I take your virginity. Could be awkward later on, you know? Falling in love with the straight guy that popped your cherry.”

Now it was Cayce’s turn for an eye roll. As if popping his cherry would make him fall in love with Reggie. ‘That’ ship had sailed down the train tracks when they were in 7th grade. No. He would ‘not’ fall in love with Reggie. Not ‘now’. But, he understood where his friend was coming from. It wouldn’t be the first time that someone had….

Wait.

What?

Beau?

“Why would your little brother consider fucking me? He’s as straight as you are.”

Reggie let out a soft snort. Yeah. He wouldn’ta thunk Beau would go there. At least, not until Beau had showed up at his house late the other night—shaking like a leaf, tears welling up in his crystal blue eyes and gasping for air—and spilled his guts and kept clutching at his arm in an attempt to stop his heart from sliding off his sleeve.

“My ‘little brother’ is a legal adult now. He’s 6’1”—in case you hadn’t noticed. He’s got that total athlete farm boy rock hard rippling muscle bod-thing going on. He’s also packing serious dick.” Reggie let out a snort of disgust. “It’s bigger than mine, much to my consternation.”

“Well, yeah,” Cayce said. Oh, yeah—he’d noticed. Beau had turned into an incredible man right before their—his—eyes. The kid was a pure, total stud. “All of that is true. I’ve seen him in those cutoffs he wears down to the bend in the river. Beau is hot as fuck, but…. Really? His cock is bigger than,” he nodded toward the raging monster between Reggie’s legs. “That?”

Reggie nodded.

“Considerably. And I rank above monolithic standards.”

Cayce’s eyes widened. He’d love to see that. But, still. Beau wouldn’t consider fucking him. Or even letting him give him blow jobs. Would he?

“But….”

“And,” Reggie stopped Cayce. “He’s gay.”

“What!”

Reggie nodded.

“He came out to me the other night. I’ve been trying to tell you but life kept getting in the way. I had that big wildfire and then that huge pile-up on the interstate when that 18-wheeler jackknifed and crushed those two vehicles and then… Well, you know what I’m talking about. You were there doing traffic reroutes.” Cayce nodded. “And then you had the shooting incident…. Anyway, yeah. Beau came out to me. I have been wanting to ask if you would consider blowing him? Or have him fuck you?”

Cayce was stunned. Beau? Gay? Beautiful, stunning, handsome as fuck Beau? Gay? Holy shit!

“And,” Reggie continued after a moment to let that news flash sink in. “And, you know he worships you. You’re one of his all-time superheroes. Imagine how fired up he would be to get to fuck one of his heroes. Hell, he would be over the moon getting to pop your cherry. The moon? He’d be in another universe.”

Cayce took pause. He was somewhat embarrassed. Now he wanted to see Beau in his full-blown glory. Could he handle getting plugged by something that big? Well, the vibrating plug he had been using was a monster. So, yeah—he could handle it.

“Yeah, I would blow Beau anytime he wanted. And, yeah—if he wanted to fuck me I’d be up for it. But….”

Reggie’s head tilted.

“But?”

“But I want you to pop it. I want you to be the first. ‘I’ would know that you were the first.” He shrugged. “Beau or Mike? Unless I get fucked by an elephant, I think they would have no idea if they were my first and were popping my cherry or not. Unless you or I told them, of course.”

Reggie nodded absently.

“What?”

“Oh. Nothing. I was just picturing you getting fucked by an elephant. You’d probably blow up like one of those parade balloons.”

Cayce shook his head. “Don’t even go there.” He paused briefly as that image flashed through his mind. “And, I’ll do my best to not fall in love with you.”

Reggie grinned and slapped his friend’s cheek again.

“I dunno, dude. Everyone falls for me.”

Cayce shook his head. Yeah. It seemed like everyone did fall for Reggie. But, he would do his best to keep that in check.

“So? You going to fuck me now or do I go patrol Four Horse Crossing in search of a horny circus elephant? Or, if you don’t think you’re man enough we ‘could’ call Beau over and the two of you could spit-roast me.”

Reggie’s head tilted. ‘Spit-roast’? Why would they skewer Cayce and dangle him over an open flame? He shrugged that comment off and reached for the bottle of lube.

“Get ready, dude. You’re about to get your brains scrambled.”

Reggie climbed between Cayce’s legs and knee’d his way between those powerfully muscled thighs. In a swift movement, he lifted Cayce’s legs rested them over his shoulders. Next, he began pouring lube over the head of his cock and down the thick shaft. Satisfied that he was well slicked for what was coming, he next applied a generous glob of the lube to Cayce’s hole and worked it in to join what was left in there from the intense finger fucking.

“Ready for more?”

“Ready for all you’ve got,” Cayce said as he watched Reggie press the huge head of his cock against his hole. Finally. Finally, they were gonna do this. Finally, he was gonna get Reggie’s cock inside him. “Give it to me.”

Air sizzled through his teeth as the monstrous cock began its dive into him. Yeah. This is what he wanted. This cock. This stud firefighter. This is the exact way he wanted his cherry to be taken. Demolished. Destroyed. Pulverized. Any number of other descriptives to follow. His eyes rose slowly from taking in that thick shaft as it began to disappear inside his hole. His gaze drifted upward along the golden blonde trail between Reggie’s crotch and navel. Upward as it skated over his rippling firefighter’s abs and then to his powerful chest—the faint puff of golden blonde at the center of the valley between his dinnerplate pecs and farther still—taking in the intense concentration exhibited on Reggie’s handsome face. His brow creased at the center of his forehead. A vein showed against his right temple.

Reggie shifted his position on the bed. He raised Cayce’s butt higher and his throbbing cock sank deeper. He glanced upward and stared into his best friend’s caramel swirled brown eyes.

“You good?” Cayce nodded a grunt. Words were failing him right now. “Tell me if you need….”

Another nodded grunt. Another thrust. Another inch sank inside the moist smoothness of Cayce’s hole.

END of Chapter 4

To be continued . . .

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