A Big-Dicked Day in the Life of Josh the Jerk

furgeson

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7 a.m.

“MMMMmmmm,” Monica moaned as she ran her hand through Carli’s brown hair. She had woken up to Carli’s face in her pussy, licking her awake. Next to her, Tanya was still fast asleep.

“One more time? Please?” Carli begged, looking up at Monica, pleading for Monica to go down on her once more.

“No, baby,” Monica said, patting her head. “I think it’s time for you all to get going.”

Carli pouted as Monica kicked her leg over Carli’s head and walked out of the bedroom. She saw Megan and Crystal, passed out on the sofa in the common area of the suite, only a sheet draped over them. She walked into Josh’s bedroom, where he was still sound asleep. Rachel was asleep next to him, and Abby was passed out, draped across Josh. He wore her bridal garter as a headband.

“Wake up, ladies,” Monica said loudly. “You don’t have to go home but you can’t stay here.”

***

Josh walked into his Dad’s kitchen. Derek was sitting on a stool at the counter in his boxers.

“She’s ready,” Derek said, seriously. “You’d better get going.”

Josh nodded and picked up two suitcases. He headed to the stairs. They were not the stairs at his dad’s house. They were longer and seemed to reach up too far. He gripped the bags and trudged up the stairs. Monica would be waiting, and she’d be mad.

He reached the top of the stairs and set the bags down. He walked through a door he didn’t recognize.

Monica stood with her back to him. She was naked except for the straps of a harness around her waist and legs.

She turned to face him. His attention was not on her face, but on the massive flesh-colored dildo strapped to her body. It hung menacingly.

“Finally,” Monica said, stepping toward him, the huge dildo swaying and bobbing.

“You’re late,” she growled. “You know I hate that.”

He looked down. He was naked, his cock as hard as it had ever been. Monica’s dildo rubbed against the side of his cock. She outsized him, slightly, but obviously.

Monica put her hand in Josh’s hair and looked into his eyes.

“I’m in charge,” she said, flatly. “You’ll do what I say, when I say it, do you understand?”

Josh nodded. He couldn’t think. He was lost in Monica’s eyes. Her words and her will were irresistible to him.

“On your knees,” she said.

Josh lowered himself to his knees. Monica seemed to tower over him now, despite her short stature. She gripped her dildo and rubbed it across Josh’s lips.

He closed his eyes and felt the enormity of the dildo. When he opened them, the dildo was replaced with the hot flesh of an actual cock.

Monica’s massive cock.

“Open,” she commanded him. “You know what to do.”

Josh opened his mouth. Monica’s unbelievable cock slid impossibly past his lips and down his throat in one smooth motion until her heavy-hanging balls rested on his chin. He looked up. Her beautiful face was framed between the undersides of her breasts. She looked down at him, smiling warmly. Her hands were on his head and she began to stroke the humongous cock in and out of his throat freely. He felt his own cock aching with hardness as he felt every inch of Monica run across his tongue.

Monica threw her head back in pleasure as she used Josh’s mouth.

“Good,” she moaned. “But I want more.”

She grabbed Josh’s hair and pulled the length of her cock out of his mouth. She pulled him onto his hands and knees and walked around him, stroking her enormous endowment obscenely.

Josh felt her kneel behind him. She laid her heavy cock onto him. He couldn’t believe how far up his back it seemed to travel. Monica raised it up and slapped it against him several times. She pushed her fingers into his hair again, and she turned his head.

She kissed him deeply, then whispered in his ear: “Time to wake up, Josh.”

She let go of his hair and leaned back, pressing the massive head of her cock against his ass.

“Time to wake up, Josh,” she said, louder now.

Josh gasped as he felt her begin to push into him.

“JOSH,” she said, louder still. “WAKE THE FUCK UP.”

***

9 a.m.

“JOSH,” Monica said, annoyed. “WAKE THE FUCK UP.”

Josh opened his eyes. He was in his bedroom at the hotel. The wedding party girls were gone and Monica was standing, fully dressed, her arms crossed and looking angry.

“I told you to get up and get ready like an hour ago,” she said, annoyed. “You have to get up RIGHT NOW or we’re going to miss our flight.”

Josh blinked at her. She threw her arms up in frustration.

“And what were you even dreaming about?” she asked. “You’re hard as shit but you were whimpering like a little bitch.”

Josh looked down. His cock was hugely hard.

Monica was shaking her head, her eyes wild. “If you don’t up right now, I’m gonna make your little bitch ass sorry. I HATE BEING LATE!!”

She stormed out of the room.

Josh followed her. His cock was still swollen and raging.

He walked out of his bedroom and into the common area. Monica was standing next to the door looking at her phone. She had her bags with her, and he sunglasses on the top of her head.

“Why aren’t you dressed?” she said, annoyed. “Come onnnnnnn, Josh.”

He walked toward her, his massive cock swaying and bobbing.

Her face changed as he approached, anger dissipating to apprehension.

“I don’t give a shit if we’re late,” he growled. “If we miss our flight, we miss our flight.”

He stopped inches away from her. Monica was silent and still.

Josh put his hand in her hair and looked into her eyes.

"Ok," she whispered.

“Now, you’ll do what I say, when I say. Do you understand?”

Monica swallowed hard and nodded.

“Never forget it.”

“I won’t,” she whispered.

“On your knees,” he commanded.

Monica lowered herself to her knees and looked up at Josh, obediently. He rubbed the head of his enormously hard cock across her lips.

“Open,” he said. “You know what to do.”

Monica grinned, then opened her mouth wide as Josh pushed into her.
 

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8:15 p.m.

Monica, it turned out, was a downright brat.

She had come into Josh room full of accusations and hate. Chelsea, kind, obedient Chelsea, had done so well in presenting Josh’s magnificent cock to Monica, helping Monica understand its size and the promise of utter sexual fulfillment that it represented. She helped awaken the desire in Monica that Josh knew would come to life once she beheld his awesome endowment. But once her yearning had awakened, Monica wanted it. And she was a brat about it.

“Stop,” Josh said as he pushed Monica’s head away. She was on her knees now, next to Chelsea, leaning in to take his cock into her greedy mouth.

“Chelsea was a good girl, despite your attempts to turn her against me,” Josh explained. He ran his hand along Chelsea’s face as she continued suckling the tip of his cock, savoring it. “She deserves to enjoy herself, and you deserve to be patient and wait your turn.”

Monica frowned and crossed her arms.

“You wanted me here, you wanted to show off your dick and fuck me,” she pouted. “So fuck me with it, 'Donkey Dick.' At least let me suck it…”

“Tell you what, you’re so eager? I have something for you to do for me," Josh said, rolling his eyes. "Are you willing to do something for me? Then you can have your turn.”

Monica looked up at him angrily.

“I guess so,” she said, flatly.

“Great, just hang on a second,” he said, moving toward the door. “Go ahead and stand up. Meet me at the sofa.”

Josh opened the door and shouted out into the hall.

“Hey Eric! Eric! You home? ERIC!”

A door down the hall opened and Aaron leaned his head out.

“Uh, hey Josh,” he said, unsure of himself. “Are you looking for me?”

“Yeah, come on down here,” Josh said, waiving.

A moment later, Aaron came into the room.

“Holy fuck,” Aaron said as he came through the door and was confronted by Josh massive, swinging cock.

“I know, right?” Josh said. He took hold of Aaron’s shoulders and moved him into the room, presenting him to the girls. “Ladies, this is my good friend Eric.”

“Uh, it's...Aaron,” Aaron said.

“Aaro…seriously?” Josh asked, looking at Aaron in surprise. Aaron nodded, trying to avoid staring at Josh’s massive cock, which stretched out in front of him.

“So anyway, Aaron asked me to send some girls his way and I figure, why not bring him here. Monica, you’re gonna give Aaron some attention while I tend to Chelsea.”

“What??” Monica asked, shocked. “What do you mean, attention?”

“Oh, nothing serious,” Josh said, dismissively. “Just a hand job.”

“I am not…” she started, but Josh cut her off.

“Or,” he said, shrugging, “you can go. It’s totally up to you.” Josh let go of Aaron and walked to the sofa where the girls stood. He picked his huge cock up and stroked it in front of Monica. “But if you take care of my friend over there….then you can have this. And I think you and I are going to have a lot of fun together if you just shut up and behave yourself.” He sat on the sofa and motioned for Chelsea to come to him. She dropped to her knees and resumed her sucking.

“Fine,” Monica said. She looked at Aaron. “Get over here.”

Aaron looked around nervously, then moved to the sofa. Josh patted the cushion next to him. “Take your pants off, stay a while,” he said. Aaron lowered his pants to his ankles. His cock was a decent size, longer than average, and surprisingly thick.

“Very nice!” Josh said, although his towering cock obviously dwarfed Aaron’s in every dimension. “I knew you had a big one, buddy.”

Aaron sat down and Monica took her place between his knees, taking Aaron’s cock into her hands.

“Monica,” Josh said. “Is that cock a lot smaller than your boyfriend’s?”

Monica didn’t respond.

“Monica?” Josh repeated. “Is Aaron’s cock smaller than your boyfriend’s?”

“No,” Monica said quietly. “It’s actually about the same. Maybe…thicker.”

Josh beamed. “Did you hear that, Aaron? Monica says her boyfriend has a horsecock, and now she says you’re the same size!”

Monica frowned.

“Go ahead and tell him,” Josh said to Monica. “Tell him he has a horsecock. Tell him how biiiiig his horsecock is.”

Monica was silent for a second, and then quietly said “it’s not a horsecock.”

“What?” Josh said, feigning surprise. “I thought you said…”

“I was wrong!” Monica said angrily. “It’s not a fucking horsecock. OK??”

Josh kept looking at Monica, smiling, but pulled Chelsea’s mouth further onto his cock. His cock ached with hardness at Monica’s words and he used Chelsea’s willing mouth to sooth it.

“What…uh…what would you say a horsecock would be, Mon?” He asked, delighted with himself.

“Yours,” she said, gritting her teeth. “You have a huge fucking horsecock. Are you happy? Just look at this!” She held Aaron’s cock in her hand and reached over a grabbed Josh’s. Her hands barely wrapped around Aaron’s thick cock, but were nowhere near reaching around Josh’s. Now, she felt the difference. She felt the size of Josh compared to what she previously thought was a well-hung specimen.

Josh removed her hand and placed it back on Aaron’s cock.

“Now, now,” Josh scolded her playfully. “Aaron first. Meanwhile, Chelsea, I think you deserve your reward. Why don’t you both take your clothes off.”

Both girls stood and removed their clothes. Both of them were remarkable, and the difference in their bodies was stark. Chelsea was tall, with long arms and legs with well-defined muscle. She had modest breasts, and her skin was fair. In contrast, Monica was short and full of curves, her darker skin covered in tattoos all over her chest and running down her torso to her legs.

Aaron was floored by the sight, but what was to come would be more than he could have imagined.

Josh motioned for Chelsea as Monica returned to her spot in from of Aaron. At first, Aaron’s eyes were fixed on her breasts. But Josh laid Chelsea onto the sofa next to Aaron and began rubbing his fat cockhead against her pussy. All eyes were on Josh’s massive pole. From their vantage points, Aaron and Monica now could see the unbelievable size of Josh compared to Chelsea’s tight pussy. Monica absent-mindedly stroked Aaron with one hand as her eyes remained fixed on the gargantuan cock entering her friend. It seemed unreal. Impossible that it could all fit. And it was the hottest thing she had ever seen.

“Fuuuuuuuuck,” Chelsea moaned, throwing her head back as Josh’s huge cockhead rubbed up and down, parting her pussy and teasing her clit.

“Fuck, that’s so hot,” Monica said, staring.

“Oh fuck.” Aaron said, as he came in Monica’s hand.

Josh and Monica looked at Aaron as Chelsea continued to wiggle her hips, her eyes closed as she enjoyed grinding herself onto Josh’s immensity, oblivious to Aaron.

"Are you shitting me? Monica asked as she looked down at her hand, covered in cum.

“Well, bud,” Josh shrugged. “That’s it for now. Time to head out.”

“Uh, oh,” Aaron stammered, collecting himself. “Could I stay and just…watch?”

Josh shook his head. “No, you’re done.”

“Oh, sure, thanks Josh,” Aaron said as he pulled his pants up. He looked at Monica who was wiping his cum off her hand onto a towel she found on the floor. “And thank you. Can I…get your number or something?”

Monica looked at him with disbelief. “No,” she said as though it was obvious.

“Oh ok…” Aaron said as he walked awkwardly to the door trying to control his still-hard dick in his pants. He left and Monica looked at Josh.

“Now what?” She asked, annoyed.

“Now you can join in,” Josh said. He guided Monica’s head to the long shaft of his cock. She purred as she licked and kissed it while he pushed into Chelsea.
 

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