A Series of Mistakes (Part 6)

Kimberly clicked the door of the Uber behind her shut, and their driver pulled off the curb, taking her and Charles to Charles’ apartment. 

“This is for you,” Charles said, waving a twenty-dollar bill over the driver’s right shoulder, “Keep your eyes on the road.”

Then, he turned to Kimberly and wrapped his arm around her waist, pulling her over to his side of the cab. As he held her up to him, his free hand reached for her shorts, unbuttoning them before he gruffly reached his hand into them, and began groping her crotch firmly. Kimberly still found herself surprised at how brazen Charles could be – fondling her in broad daylight just a foot away from their very conservative-looking driver was jarring and arousing in equal parts. His fingers toyed with her freshly fucked lips, smearing his leaking cum against them as he leaned in and planted a delicious, sensual kiss on her lips. 

Then, he pulled away, and lifted his cum-covered index and middle fingers up to her lips and pushed them into her partially open mouth before she could protest. 

“Suck,” he commanded.

He watched, his eyes fired with lust as she sucked firmly on his fingers like they were a tasty lollipop. With Charles’ fingers knuckle-deep in her mouth, Kimberly’s eyes flitted up to the rear-view mirror of the cab. There she caught the driver’s gaze, his eyes having widened considerably upon seeing the scene playing out in the back of his cab. Unsurprisingly, Charles’ twenty-dollar bill had clearly not been enough of an incentive for him to suppress his curiosity at the curious sounds coming from the backseat of his car. 

Charles pulled his fingers out of Kimberly’s mouth, and pushed them back into her crotch before he reached for her wrist and placed her right hand against the bulge in his trousers. Still sheepish, Kimberly massaged him tentatively, running her fingernails over the outline of his cock and feeling it twitch under her fingertips. Charles’ fingers were massaging Kimberly’s pussy firmly in a circular motion, teasing her swollen lips as her hips began to shift from side-to-side, trying to accommodate more of his hand inside her short, tight pairs of pants. 

Suddenly, just as Charles’ free hand was about to expose her breasts in the back of the cab, the car screeched to a stop, and the driver, whose eyes were now staring straight ahead, unwilling to turn around anymore, waited silently for the two to exit his vehicle. 

Kimberly quickly buttoned her shorts, and shot out of the cab hastily, Charles exiting from the other door. Her cheeks burning with both excitement and embarrassment, she followed Charles as he pressed his keycard up to the slick, hi-tech-looking scanner at the foot of his apartment building. It beeped, and the glass doors slid open, letting them both in. 

“Mr. Parker, you’re early today,” a distinguished-looking older gentleman in a suit and tie greeted Charles from behind the concierge counter in the ‘lobby’ hall of his apartment.

Charles winked, and shot the man a sly grin, hugging Kimberly around her hips.

“Just the usual, Bobby, a bit of business to take care of,” he laughed, eliciting a knowing nod and smile from the man. 

Kimberly’s heels clicked against the marbled floor in the lobby as they walked toward the elevator, when she saw a gaggle of young, handsome men walking in their direction. 

“Charles, what the fuck is up?” came a voice from the group, belonging to a good-looking, chiseled figure much like Charles’. 

Kimberly, not the most familiar with the speak of ‘manlier’ men, having spent very little time with them, was confused as to whether this was some sort of threat, or just a friendly ‘hello’. Charles’ smile and the subsequent handshake-hug the two men shared confirmed, thankfully, that it was the latter. 

“Fuck me, haven’t seen you boys in a while,” Charles said, scratching his stubble, “Been so fuckin’ busy at work.”

“Busy at work, eh?” another voice chimed, wagging his chin in the direction of Kimberly. 

The men all laughed; Charles included. 

“This, is Greg’s girlfriend,” he snickered, gripping her by her hip and pulling her up to his side. 


In that moment, Kimberly felt, paradoxically, both completely transparent and the subject of all the men’s attentions. They were looking at her, their eyes roaming her body – likely mentally tearing her clothes off and picturing her naked – but they did it with a complete disregard for her. It felt like they’d completely overlooked her, having not even greeted or otherwise acknowledged her presence till now, and were only drinking her in for the sight her skin and her assets presented. It should have been demeaning, or at least mildly offensive – college Kimberly would have given the men a dressing down for the disrespect they were showing her – but instead of feeling indignant or irate, she only felt exhilarated. The way the pack of men eyed her from top to bottom with wanton disregard for her response… it made her feel like an attractive, sexy, prized woman. Perhaps it was some primal urge that remained deep in her psyche that had finally found its way to the surface, or maybe she had always been a slut but was only now finding out about it. Either way, all Kimberly knew was that in that moment, she was so turned on by the attention she was receiving. 

“Greg like that dude from work?” one of them asked Charles, to which he received an affirmatory nod. “Bitch couldn’t even handle a couple of drinks,” the man said, shaking his head, referring to an incident during a house party Charles threw, where Gregory passed out soon after his third shot, an incident even he found quite embarrassing. “It’s no wonder he can’t hold down this piece of ass.”

“Why don’t you give us a twirl,” one of them said, his eyes glued to her hips. 

Charles, without looking to Kimberly for approval, gripped her hand and lifted it above her head. Not knowing if she acquiesced because she felt like she had little choice, or because she genuinely wanted to, Kimberly began a 360-degree spin, eliciting a series of whistles and catcalls, especially when her back was fully turned to them. 

“Premium girlfriend ass right here,” Charles said, gripping her butt, before parting the sea of men with Kimberly in tow. “See y’guys later,” he winked, the men all still too pre-occupied with Kimberly’s figure to afford their friend more than a series of cursory, goodbye mumbles. 

“I’d bend that bitch over,” snickered one of the men, as Kimberly slipped through the crowd.

“He might let you, if you’re nice,” another one chuckled back, whistling.

She felt their heated breaths against her neck, them barely moving out of the way for her. They let her squeeze up against them as she followed Charles to the elevator with her hand tightly gripped on his. Her heart pounding in her chest, Kimberly turned to take one last look at the hungry-eyed men behind her, before she stepped into the elevator and the doors closed behind her.


The next four hours in Charles’ apartment were different for Kimberly. They represented a turning point. It was in those four hours that Kimberly finally accepted who she now was – she dropped the pretenses and the shyness she forced herself to exude in an attempt at modesty. She accepted that she was turned on not just by the fact that Charles was amazing at sex, or the fact that he had a much bigger cock than Gregory, or even the fact that his cocky, asshole-ish demeanor was so basely masculine that she found it attractive. All of those things contributed to it, sure, but what chiefly turned Kimberly on – what brought her to the edge of every climax she now had, and what fueled every moan that escaped her lips – was a kink that had far more shades of nuance to it than the simple instinct behind craving a bigger cock, or wanting a man who knew how to hit all the right spots better than her boyfriend could. 

No, what Kimberly really liked, was to cheat. 

Kimberly loved to cheat. 

Kimberly loved to cheat on her boyfriend with Charles. That was what turned her on. Perhaps it was something she gained a taste for gradually over the past three weeks, or perhaps it was always a dormant desire in Kimberly that she had simply never realized. Deep down, she knew that this debauched desire must have existed somewhere deep inside her all along – if not, why would she have followed Charles up the stairs in Cheryl’s home when he asked her to? She must have known where it would lead, and what would happen. She must have. 

Kimberly had finally accepted this dark, depraved desire that she had been trying to keep squirrelled away since the first time she realized it existed. She had been trying to erase the guilt that had been gnawing away in the pit of her stomach since her affair with Charles had begun, not realizing that what she was experiencing wasn’t in fact guilt, but a much subtler cocktail of trepidation and titillation that she actually thoroughly enjoyed. 

It didn’t matter now because finally, for the first time since her trysts with Charles had begun, Kimberly had fully surrendered herself to her darker desires. She admitted it to herself, and was admitting it to Charles over, and over again as he pounded her, his cock driving in and out of every one of her orifices, all over his apartment. 

“I l-love, mmmh… I love c-cheating on my boyfriend,” Kimberly whimpered, turning her thoughts into words while her body shook to the rhythm of Charles’ pumps, her clothes all off except for the heels on her feet, up in the air. 

“Say his fucking name,” Charles grunted, thumping into her, his hands pushing down on her thighs and opening her up even wider for his long, hard strokes.

“I love c-cheating on B-Greg,” Kimberly moaned, her tits bouncing, “I l-mmmh… I love cheating on Gregory.”

She came over his cock countless times that night, and each and every time she did, she thought about how in love she was with the idea of cheating. The taboo of infidelity, the exhilaration that came with its secrecy, and the debauched, twisted high that came with knowing how much she was always at risk of sacrificing for meaningless, carnal pleasure… all of it came together to shake her body with shattering orgasm after orgasm. 

By the end of their night together, Charles’ initiation of the dirty, smutty dialogue between them wasn’t enough to satisfy Kimberly anymore. She needed more, and she overcame whatever final vestiges of decorum or decency she was holding onto, and spilled from her own lips the perverted, debased thoughts that she could ride to greater heights of excitement.  

As Charles eased in and out of her, thrusting into her in the motion of a slow, deliberate grind, trying to hold himself off from cumming too soon, Kimberly bit her bottom lip, pressed her hand up to his chest, and looked into his eyes. 

“How much do you enjoy it?” Kimberly asked, her mascara-heavy lashes fluttering seductively, “How much do you enjoy fucking your friend’s girlfriend?”

Charles looked up, his face betraying slight surprise. Kimberly had been warming up to the idea of dirty, flirtatious talk during sex, but was now pleasantly amused by how comfortable Kimberly had become with talk of her infidelity.  

Charles’ response was a devilish grin. Then, he pulled out of her, turned her over on his plush, queen-sized bed, and pumped his cock back into her. Gripping her by her hair, he pulled her head back up to his lips, and whispered in her ear. 

“I fucking love it,” he grunted, sending a strong, lone chill down Kimberly’s spine. 

“You like fucking me while my boyfriend does your work at the office?” she whispered, as Charles ground his cock into her deliberately, his fist still firmly gripping into her hair. 

“I’ll fucking do it again if you tell me to,” Charles said to a whimpering, moaning Kimberly, “Tell me to.”

“Keep him there,” Kimberly moaned, “Keep him there all fucking weekend so we can fuck, and so I won’t have to see his fucking face.”

The two alternated between rough, hard fucking and making gentle, sweet love for hours, the dialogue between them only getting more intense. By the end of the night, Kimberly had cum five times, each time squealing Charles’ name at the top of her lungs, completely free of the worry of being heard or found out. 

“I wanna’ cum all over that pretty little face of yours,” Charles grunted, pulling out after Kimberly’s latest orgasm. 

Nodding, she knelt to the floor, assuming the position as Charles stood over her and began jerking his cock over her face. Dipping her head down, she took his hung balls in her mouth, slobbering over them as her eyes looked into his, egging him on. 

“Cum on my slutty little lips, Charles,” she begged, licking her lips slowly, “Make them yours and you can have them whenever you want them.” 


“Whenever, Daddy,” Kimberly nodded, smiling cheekily. “You can fuck me right in our apartment, even when he’s there… if you can pull it off,” she said, her tongue toying with the underside of his throbbing rod. 

Kimberly’s seductive, tantalizing tone drove Charles over the edge. Pulling her face up by her chin, he sprayed shots of cum all across her face, dousing her in his thick, warm seed. Grunting, his cleaned his cock off on her lips as the last of his cum oozed out of the tip of his rod and dripped on her face. 

“I can pull anything off,” Charles said, winking.