The Worst Night of His Life - Part 1

“This place is great!” Penny shouted over the music that filled the club. “I love, love, love the music!”

She spun around and moved her hips in time with the beat as Jacob stared at her ass in the skintight wet look leggings she’d slipped into for their night out. She spun around again and smiled, but Jacob barely noticed as he couldn’t tear his eyes away from her breasts and the way they bounced in her camisole.

“Dance with me!” Penny said.

Jacob sipped his drink from the comfort of his bar stool and shook his head. “No, Penny, you know I can’t dance,” he replied.

She frowned playfully and stepped closer. Her lips found his neck as her hand moved between his legs. Jacob’s eyes went wide as his girlfriend groped him in the middle of a crowded night club, but he made no effort to stop her. It felt too good to do that.

“Please,” Penny said into his ear. “I want to dance with you, baby. I want rub up on you out there. I know you love my ass in these leggings and I’ll let you play with it if you dance with me. You can grab and grope me all you want.”

Jacob was half hard by the time Penny backed away and smiled as she waited for his response. He was certainly tempted by the offer, but he wasn’t kidding when he said he couldn’t dance. He literally had no rhythm and there was no question he’d embarrass himself. “I’m sorry, babe, but I wasn’t kidding. I really can’t dance. I’ll look like an idiot.”

Penny’s frown returned, but this time it was a little less playful. Jacob felt bad. He’d disappointed his girlfriend, but he just couldn’t make a fool of himself in public.

“You won’t mind if I go out there and dance, will you?” Penny asked as she gestured towards the crowded dance floor.

“Not at all,” Jacob said. “That’s why I brought you here. I’m sorry that I can’t dance, babe. I really am.”

Penny smiled, kissed him on the cheek, and said, “Don’t worry. I’d rather have you out there with me, but I can have fun all by myself.”

She spun around, sauntered onto the dance floor, and immediately began to move her hips in rhythm with the music. Jacob sipped his drink and watched her mesmerizing ass in the shiny, skintight leggings. He felt something in the back of his head gently trying to nudge him out there with Penny – for no other reason than to feel that perfect ass bouncing against him as she danced – but Jacob resisted.

That sensation returned when a guy sidled up next to Penny and started dancing along with her. Jacob expected she’d move away – after all, what kind of woman dances with another guy in front of her boyfriend – but she didn’t. Instead, Penny smiled and turned to face the stranger.

Jacob felt a little jealous, but Penny seemed to be having a good time and it struck him as mostly harmless. At least, it seemed that way until the guy reached out and put a hand on Penny’s waist. He pulled her closer and she offered no resistance. Suddenly they were dancing with just a few inches of space between them. Jacob sat up straight on the bar stool and squeezed the glass in his hand a little tighter.

Then the guy put his hands on Penny’s hips and spun her around. He pulled back and her ass pressed into his crotch. Jacob figured Penny would walk away at that point, but she didn’t. Instead, she smiled, looked back at the man holding her hips, and ground her ass into his crotch. In the span of just a few moments they’d gone from dancing together to practically dry-humping. Jacob put his drink on the bar, slid off the stool, and approached the dance floor.

“I wanna dance,” Jacob said.

Penny smiled and he figured she’d step away from the stranger, but she didn’t. Instead, she replied, “Too bad. I already found a willing dance partner.”

The guy’s hands moved up Penny’s taut stomach and came to rest just under her breasts. She reached up and slipped a hand around the back of his neck as a new song with a slower beat started. Their bodies moved in tandem as Jacob’s jealousy deepened.

“Penny, I’m sorry I didn’t want to dance,” Jacob said. “I do now.”

“But you said you’re not a good dancer,” Penny replied. “Austin here is an excellent dancer, as I’m sure you noticed. It’s almost like we were made for each other, as dance partners, at least, and I want to keep dancing with him. Now go back to your bar stool.”

Jacob wanted to keep fighting, but there was something about Penny’s tone and the look on her face that made him feel like that would be a mistake. He was fairly certain she was punishing him for his unwillingness to dance with her, and if that was the case then the smartest move was probably to take his punishment, so he went back to the bar stool, sat down, and threw back the rest of his drink.

Penny’s gaze remained on Jacob as she and Austin continued to dance in a remarkably intimate manner. Their bodies moved gracefully along with the beat as Austin’s hands traveled all over Penny’s stomach and hips while her ass remained pressed tight against his crotch. She glanced at Jacob from time to time, smiling when she did and seemingly taunting him with the notion that he could be the one she was eagerly rubbing up against her if he’d had the courage to get on the dance floor and make a fool of himself.

They danced for two more songs before Austin took Penny’s hand and they walked over to the bar. Austin ordered two drinks before putting his arm around Penny like they were the couple on a date. She made no move to slip out of his grasp, making Jacob stir uncomfortably in his seat.

“How did you learn to dance like you do?” Penny asked.

Austin looked down at her – he was at least six inches taller than Penny – flashed a confident smile, and said, “Women love a man that can dance and I love women, so I learned by doing. I’m sure I looked like an idiot at first, but now I look good so none of that matters.”

Penny turned to Jacob, smiled, and said, “Women do love a man that can dance.” She looked back at Austin and asked, “Why do you think that is?”

Austin’s hand moved down Penny’s back and came to rest just above her ass before he said, “Because a man that knows how to dance is also a man that knows how to fuck.”

His hand – which was quite large – moved to Penny’s ass and he grabbed a handful of her soft flesh. She leaned into him while her head turned towards Jacob. She didn’t say a word, but Jacob could see something in her eyes, almost as if she was delighted at how forward Austin was being.

“Hey,” Jacob said. “Take your hand off her ass.”

Penny smiled before she turned and looked up at Austin.

“Fuck off, man,” Austin replied. “If she wants me to take my hand off her ass, she can tell me. I’m a gentleman, after all. But I’m pretty sure that’s not what she wants. I’m pretty sure she likes having my hand on her ass, just like she liked having my hands all over her perfect body while we were dancing.”

“You think my body is perfect?” Penny asked before Jacob could respond.

Austin stepped away from Penny for a moment and his eyes wandered over her body. He nodded, stepped closer, and put his arm around her waist to pull her close. “You’ve got the best body in here. There’s no contest.”

“You’re hot too,” Penny said.

Austin’s hand moved to her ass once more and this time he squeezed it hard. Penny smiled and Jacob was almost certain he heard a little bit of a moan, though the music was loud enough that he couldn’t be sure. He was absolutely certain he’d had enough of his girlfriend flirting with another guy, though.

“Penny, that’s enough,” Jacob said. “Stop this. You’ve made your point. I should have just danced with you. I get it, okay?”

“You don’t seem to understand what’s going on here,” Austin replied.

“I wasn’t talking to you,” Jacob shot back.

Austin smiled at Jacob for a moment before turning his attention to Penny. His hand moved to her waist and he spun her gently until their bodies were pressed together. Penny looked up at Austin and he kissed her. He grabbed her ass with both hands and she turned her head as the kiss deepened. Jacob couldn’t see, but he was certain Penny had welcomed Austin’s tongue into her mouth. She was certainly moaning like the kiss was hot, and he could absolutely hear it over the music.

The kiss ended and Austin spun Penny around until she was facing Jacob. His hands moved to her waist and he pulled back until her ass pressed into his crotch just like it had on the dance floor. He brushed her hair to one side and kissed her neck, putting a lusty smile on Penny’s face while she stared into Jacob’s eyes.

“What are you doing?” Jacob asked.

“What does it look like?” Penny replied.

“It looks like you’re cheating on me,” he said.

Austin’s hands moved to Penny’s breasts and she closed her eyes and moaned as another man groped her in the middle of the club.

“I guess I am,” Penny replied. “Does that upset you?”

“Yes!” Jacob answered. “Of course it does. What the fuck, Penny?”

The bartender delivered the drinks Austin had ordered, but if Jacob’s raised voice caused any alarm he didn’t show it.

“If it upsets you, why don’t you do something about it?” Penny asked.

Jacob considered what he could do to remedy the situation, but outside of physically separating Penny and Austin, nothing came to mind and he didn’t really feel like getting in a fight in the middle of a bar and getting tossed out on his ass.

“He’s too weak,” Austin said before Jacob could answer his girlfriend’s question. “He knows I’d kick his ass if he tried anything. So instead he’s going to sit there and let me take you from him.”

Austin reached up and turned Penny’s head so he could kiss her. Jacob watched his girlfriend’s mouth open and welcome Austin’s tongue as he resumed playing with her tits right there in the middle of the bar.

“Is he right?” Penny asked when her gaze returned to Jacob. “Are you too weak to stop him from taking me?”

“Penny, please,” Jacob replied. “Don’t do this. I don’t…I don’t want to fight another guy. That’s stupid.”

Austin laughed. “More like he doesn’t want to get his ass kicked, like he knows he would. Just tell her, man. Just admit it. You know you can’t stop me from taking her and you know she wants me to take her.”

“Fuck you,” Jacob said.

They stared at each other for a few seconds, though Austin’s hands continued to roam over Penny’s body and she seemed to find great delight in it.

“He’s hard for me,” she said.

“What?” Jacob asked.

“Austin’s hard for me,” she said. “I can feel his cock pressing into my ass. He was hard for me when we were dancing, too. He wants me, Jacob. He wants to fuck me.”

Jacob was astounded. What had seemingly begun as a simple way to punish him for being unwilling to dance had spun out into something completely out of his control.

“She’s right,” Austin said. “I want to fuck your girlfriend. I’ve wanted to fuck her since you two walked in here.”

Penny turned her head and kissed Austin again. She reached back to run her fingers through the hair on the back of his neck and she moaned as their tongues danced and he grabbed her ass with one hand while the other remained on her hip.

“The question is, what are you going to do about it?” Penny asked as she turned back to Jacob.

Jacob stared in silence. He couldn’t muster up an answer because he couldn’t wrap his head around what was unfolding in front of him.

“I told you, he’s too weak to do a damn thing,” Austin said. “Either that or he’s a fucking cuck that would love to see his girlfriend get fucked by another guy.”

“I’m not a cuck,” Jacob replied.

“Then you’re just weak,” Austin shot back.

Penny and Austin stared as Jacob searched for something to say or do that would restore his evening to the state it had been in before Penny had stepped onto the dance floor. He waited too long, though.

“You’re right,” Penny said. “He is weak. He didn’t have to let you dance with me. He could have tried to stop it. He didn’t have to let you kiss me. He didn’t have to let you grab my ass or play with my tits. He didn’t even try to stop you, though.”

Austin flashed a victorious smile and kissed Penny’s neck before saying, “He didn’t stop me because he’s weak. He knows he’d get his ass kicked and he’s so afraid of the embarrassment that he’d rather just let it happen. He’s the most pathetic kind of man.”

Penny stepped out of Austin’s grasp and moved towards Jacob. She put a hand on his knee and her fingers traveled up his leg and grasped his cock before she leaned in and kissed his neck. “He’s right,” she said softly. “You’re weak. You’re pathetic. You’ve proven that tonight. That’s why I’m going to let Austin take me home. That’s why I’m going to let him fuck me as many times as he wants. That’s why I’m going to enjoy the big cock he’s got in his pants.”

To his horror, Jacob got hard as Penny humiliated him.

“You can take me home,” Penny said to Austin as as she released Jacob’s cock.

“Did you drive here?” Austin asked.

Penny nodded towards Jacob and said, “He did.”

Austin smiled. “Good. I don’t feel like paying for an Uber, so you’re going to drive us back to my place.”

“What? No,” Jacob said. “Fuck you.”

Austin stepped forward, grabbed a handful of Jacob’s hair, and pulled him off the bar stool. He dragged him through the crowded club and towards the door, all while Jacob struggled in vain to gain his release from the stronger man’s grasp.

“Where did you park?” Austin asked once they were outside.

“Fuck you,” Jacob said.

Austin tightened his grip and pushed down hard enough that Jacob fell to his knees. He looked up to see Penny standing right by Austin’s side with a smile on her face. “Spit on him,” Austin said.

Penny’s smile grew bigger and brighter for a moment before she reared back, gathered her spit, and leaned forward. Jacob closed his eyes a split second before the warm liquid hit his face. Confusion and humiliation engulfed his body as it became clear that he’d completely lost Penny and a great deal of self-respect along with her.

“Where did you park?” Austin asked.

Jacob turned as far as he could with Austin’s fingers still entwined in his hair, pointed, and said, “Over there. Next to that black pickup.”

“Stand up,” Austin demanded as he pulled up on Jacob’s hair.

Jacob stood and Austin stepped off the curb and towards the car. He kept his grip on Jacob’s hair, though, guiding him through the parking lot like he was little more than a puppet to be used for his amusement.

“On your knees,” Austin said as they reached the driver’s side door.

He hesitated and once again Austin pushed down hard enough that Jacob couldn’t stay on his feet. He dropped to his knees on the unforgiving asphalt and looked up at Penny to see her happily standing by Austin’s side once more.

“Pull her leggings down to her knees,” Austin ordered.

Jacob looked to Penny for relief from the command, but she only said, “What the fuck are you waiting for? Isn’t it clear who’s in control here, Jacob? I could spit in your face again if you’d like? Is that what you really want here, weakling?”

Jacob shook his head and reached up to pull Penny’s wet look leggings down to her knees, just as Austin had ordered.

“Now put your fingers inside her,” Austin demanded.

Jacob reached up, ran a finger along Penny’s labia, and slipped inside her with ease.

“Is she wet?” he asked.

Jacob nodded. She was more than wet, though. She was soaked. She was wetter than she’d ever been for him.

“Why do you think she’s wet?” Austin asked.

“I…I don’t know,” Jacob replied.

Austin released his hair and slapped him so hard that Jacob toppled over onto the asphalt. He reached up to try and soothe the remarkable pain, but to no avail.

“Answer my fucking question,” Austin said.

“Because she’s turned on,” Jacob answered from the ground.

“Why is she turned on, weakling?” Austin asked.

“Because…because of you,” Jacob said.

Austin reached over and slipped two fingers into Penny’s pussy. She moaned loudly and they kissed as he roughly played with her breasts with his other hand. Jacob could hear the sounds of her wetness as Austin’s long fingers moved in and out of her.

“Why are you turned on?” Austin asked Penny as he continued to finger fuck her.

“Because it’s been a long, long time since I’ve been fucked by a real man,” she said. Her gaze turned to Jacob and she added, “And because I like watching you abuse him.”

It was unquestionably the most fucked up thing Jacob had ever heard, and yet it made perfect sense in the context of their evening. Penny had never seemed like a cruel person, and yet she was being cruel to him. She’d done nothing to stop Austin’s cruelty, either.

“Look at that,” Austin said. “It turns out you can turn your girlfriend on. All you have to do is be the pathetic little bitch that you clearly are.”

Penny spit on Jacob again, this time without prompting. She moaned as her saliva dripped down his face and onto his neck and he made no effort to get up off the ground as another man fingered her.

“I need to get fucked,” Penny said. “Unlock the fucking car and drive us back to Austin’s place. Right fucking now.”

Jacob took a deep breath, stood, and unlocked the car. Austin and Penny got in the backseat and he got behind the wheel, started the car, and backed out of his space while his girlfriend kissed another man with a kind of passion she’d never displayed for Jacob.

“Can I suck your dick?” she asked.

“Go for it,” Austin replied.

“Where am I going?” Jacob asked as the sound of Austin’s pants being unzipped emanated from the backseat.

A few moments passed before Austin tossed his phone into the front seat. He’d opened his maps app and his address was typed in and ready to go. The sounds of a blowjob reached Jacob’s ears as he hit the start button and got the first directions from the robotic voice.

“Fucking hell, you’re damn good at that,” Austin said.

“It’s nice to have a real man’s cock to play with,” Penny replied as the sound of a slick handjob filled the car. “But I don’t think I can wait until we get back to your place. I need to get fucked right now, Austin.”

“Then get on top,” Austin said.

Jacob squeezed the steering wheel as his frustration boiled over. He couldn’t keep driving as Penny fucked someone else in the backseat of his car. He couldn’t take that kind of humiliation.

“I will beat you until you’re bloody if you stop driving,” Austin said from the backseat, as if he’d noticed Jacob’s growing frustration and his desire to do something to relieve it. “I don’t give a fuck if you’re freaking out up there. You will not stop this car. You will take me and your girlfriend back to my place and you will do so without hesitation. We both know I can kick your ass and we both know it would only make Penny more desperate for my dick if I did, so let’s not pretend that I wouldn’t be happy to give you the beating of a lifetime, Jacob.”

A potent kind of fear gripped Jacob, prompting him to take a deep breath and try his best to block out the sounds of sex now emanating from the backseat. It seemed that Penny was turned on by Austin’s threat, which shouldn’t have surprised Jacob. Of course she was.

“You know what, apologize to me for getting frustrated,” Austin said. “Apologize for even considering not driving me and your girlfriend back to my place so I can wear out her pussy by fucking her all night.”

Penny moaned and added, “Do it, Jacob. Fucking do it. Do as you’re told.”

Jacob knew Austin could kick his ass if he wanted, and he strongly suspected Austin would have no problem doing such a thing, which left him with no option. He had to apologize.

“I’m sorry,” he said. “I shouldn’t have gotten frustrated. I should have just driven you like you told me to.”

“Damn right you should have, you little bitch,” Austin replied with a laugh.

“Oh my fucking god, I’m cumming!” Penny cried out. “Fuck, fuck, I’m fucking cumming!”

Jacob felt an urge to drive into a telephone pole as his girlfriend came on another man’s cock in the backseat. He couldn’t imagine a more thorough form of humiliation.

“Was that good?” Austin asked.

“That was the best orgasm I’ve ever had,” Penny replied.

“There’s plenty more where that came from,” Austin said. “Don’t you worry about that.”

Jacob glanced at the map on Austin’s phone and saw that they were nearly at his place. He breathed a sigh of relief. The worst night of his life was about to come to an end.

The sounds of kissing and slow sex filled the car as Jacob pulled up in front of a nice-looking house and said, “We’re here.”

“Get out and get on your knees in front of the car,” Austin ordered.

“What?” Jacob asked.

“Stop asking such stupid fucking questions and do as you’re told,” Penny demanded.

Austin laughed and Jacob turned the car off, got out, and dropped to his knees in front of the hood. He waited there for a few minutes before Austin and Penny got out. They were both fully dressed and he had quite the bulge in his pants.

“Take my cock out,” Austin said as he and Penny stood in front of Jacob. She dutifully reached down, unzipped his pants, and pulled out his mostly-stiff cock.

“Good girl,” Austin said. “Now, open your mouth, Jacob.”

Jacob looked up at Penny and Austin and then at the cock that rested just a few inches from his mouth. He could only imagine that demand leading to one outcome, so he kept his mouth closed and shook his head to indicate his refusal.

Austin reached out, grabbed a handful of Jacob’s hair, and pulled him to his feet. He slammed his face and chest into the hood of the car and yanked down Jacob’s pants and underwear to expose his bare ass.

Jacob cried out in pain as Austin delivered a series of swift blows to his ass. The sound of flesh meeting flesh filled the night air as Jacob covered his mouth to muffle the cries of pain. As much as the appearance of a neighbor might have rescued him, it would also have meant someone else witnessing his humiliation.

“You want a go?” Austin asked after he relented.

“Absolutely,” Penny replied.

A moment later she delivered a spanking with surprising force. The pain was astonishing and Jacob felt it emanate down his legs and up his spine, leaving him in a weakened state as everything he thought about himself seemingly melted away in the face of their relentless abuse.

Austin tightened his grip on Jacob’s hair, pulled him from the hood of the car, and pushed him to his knees once more. “Open your mouth,” he demanded.

This time Jacob did as instructed. He looked up at Austin and opened his mouth. The stiff cock moved between his lips and Austin held it there.

“You don’t need to do anything other than keep your fucking mouth open while I fuck your face,” Austin said. “Do you understand that?”

Jacob nodded as best he could with a big dick in his mouth. The face fucking began a moment later. The long, thick cock that had fucked Penny moved in and out of his mouth. Jacob’s jaw ached almost immediately and he couldn’t help but gag and drool as Austin approached the back of his throat repeatedly.

“You can play with your pussy if you want,” Austin said. “Don’t be afraid to embrace what turns you on. I know you like that I’m using your boyfriend’s mouth like it’s a pussy. I know you like seeing this little bitch on his knees with my dick in his throat. I know you like seeing his complete and utter humiliation, so go ahead and play with your cunt.”

Penny slipped a hand into her leggings and did just as Austin suggested. Jacob watched his girlfriend’s face contort with pleasure as she rubbed her clit. He watched her get off on his humiliation. He hoped it would all end soon, that he’d be free to get in his car, drive away, and never see Penny or Austin again.

Austin pulled his cock from Jacob’s mouth and slapped his face with it. He rubbed the spit-soaked head all over, coating Jacob with his own juices. He shoved it back in his mouth, pushed it into his throat and held it there as Jacob gagged relentlessly. He pulled it out once more and rubbed the thick mucous over Jacob’s face.

“Let’s go inside,” Austin said.

Jacob breathed a sigh of relief. It was over. He was free. The worst night of his life had come to an end.

“What are you so happy about?” Austin asked. “You’re coming with us. We’re not nearly done with you yet.”

“No, please, no,” Jacob said.

Austin laughed. “You don’t get it, do you? Your girlfriend gets off on you being abused like the pathetic weakling you are. She came so hard on my dick because she likes it when I treat you like a piece of shit. So that’s what I’m going to do. You’re coming in my house and you’re going to be our little plaything as we enjoy a night of the best sex we’ve ever had. Do you understand?”

Jacob had never felt so powerless in his life. He knew any resistance would be met with more of what he’d already suffered through. He’d be slapped, spit on, and spanked, or worse. He resolved to survive, to make it through the next few hours. Then he could have his freedom.

“Yes, I understand,” he said.

Austin smiled. “Good boy. Now let’s go inside and have some real fun.”

“I can’t wait,” Penny said.

Fear gripped Jacob once again, but he took a deep breath and told himself that it couldn’t possibly get any worse than it already had. All he had to do was survive.