Payback's A Cassandra

“And I was like, just throw me down and fuck me, you know?”

Josh almost sputtered and coughed into the water filling his conical water cup, still not used to some aspects of his new reality as he threw a side-eye over to the trio of ladies hanging out over by the water cooler next to his. It was downright incredible just how a few small changes had such incredible impact—from the way women felt free to air out their sexual laundry, to how many high-fives he’d gotten from the office’s other guys over what he’d pulled with Kelly. Apparently, being a pervert big enough to get in trouble with the boss was kind of a badge of honor around here.

But, as his slight but persistent chub wasn’t ready to let him forget, he hadn’t done anything to actually seal the deal, which brought him and his new favorite app here, to scope out some of the office’s choicest ladies and hopefully fix that situation. There was Kelly, of course, who was making eyes at him and had been since he arrived, undoing about three buttons just in the time he’d been standing there. Then there was Gabriella, Kelly’s red-headed friend who was more cute than hot, and significantly more modest by way of crossing her arms across her frumpy blouse—but from what he’d managed to wedge out of the office gossip machine, it was more out of a lack of confidence than anything else, sporting a less impressive body than her chesty friend and anxious about not getting any compliments because of it. In a world where complimenting big breasts is the norm, is ignoring little breasts considered an insult? Maybe I should fix that. But that was a thought for later, as he looked to the last of the three, by far the most appealing for a variety of reasons, not least of which being her raven locks, statuesque figure, and, where he was concerned, a very active resting bitch face.

He and Cassandra had started in the company at pretty much the same time, and worked in the exact same department. But for some reason, that almost certainly had nothing to do with her just being a better all-around employee than he was, she had been promoted over him, and she had never ever once let him forget that. Despite the fact that they had actual interns for that kind of thing (such as, y’know, Kelly) if there was ever any kind of menial task that Cassandra needed done, she saw to it almost personally that it ended up in his hands somehow. Payback for perving on her in the months before her promotion? Maybe. But it those same looks and curves combined to mean he could never bring himself to say no, distracted as he was by all of the blood rushing directly from his brain.

And now, in this universe where women were practically tailor-made to love his brand of leering perversion, her opinion of him still wasn’t all that much better than it was before, despite how he couldn’t see himself having held back from complimenting her amazing figure at every opportunity and groping her whenever she got uppity. Some people are just never satisfied. He groused, somewhat hypocritically, before making his way over to the three, his decision made. “Ladies!” He said, stopping between Kelly and Gabriella to look across at Cassandra, his grin going from wide to cheeky as he looked at her. “And Cassandra. Might I say, all of your hot tits are looking excellent today!”

Kelly’s face filled up with a blush, followed by rolling her eyes. “You’re just never off, are you? I know most guys love breasts, but I’m beginning to think you might be in love with them.”

“Th-thank you, Josh.” Gabriella said, fidgeting anxiously as her face flushed pink instead, her eyes darting from him to the ground and back while she began anxiously playing with the dangling locks of her red hair. “I-I know you can’t see them very well, because… Well… Because…”

“Mmm.” Cassandra said, that slight smirk she apparently saved just for him resting coolly on her aristocratic features. “If only you were as talented at flattery as you were at getting those reports to me on time. How are those going, by the way?”

The other two laughed nervously while Josh’s expression soured, realizing at last that even in this new reality, Cassandra valued things like ‘efficiency’ and ‘timeliness’ over someone complimenting her tits like she was a trashy street whore. Well, that was enough of that!

“Hey Cassandra, I know we haven’t been on the best of terms lately,” He started sweetly, and he could see suspicion gathering in her narrowed eyes, “but I would really like it if you turned around, bent over, and showed off your ass to me.”

It was gradual, and slight, and didn’t show up all at once, but there was no denying it—his ball-buster of a boss was actually smiling. “Sometimes, I really do wish I could overlook your poor work ethic and constant tardiness,” she said, as she reached down to hook her thumbs around the hem of the plain but dressy business skirt hugging her waist, “because you know exactly how to talk to a lady.” Mouth drying as his eyes widened, Josh looked on in excited awe as his frigid ice queen of a boss began shimmying her way out of her skirt, one hip-clinging inch at a time, revealing her creamy, toned thighs bit by bit to his devouring gaze. Finally losing enough tension to pool around her kitten-heeled feet, she stepped out of the skirt with steps higher than strictly necessary, giving him tantalizing glimpses of the way her calves flexed and rippled with supple muscle, before finally coming to a stop away from him, facing towards a table covered with a simple blue plastic tablecloth and that supported all of the watercooler’s cups. Then, with a knowing smile lobbed over her shoulder, she began to lean forward, thrusting out her succulent, taut booty out towards him, clad in black panties that clung to the length and breadth of her ass’s curve while giving out just the barest hint of further exposed skin by the lace clinging to the garment’s edges.

Josh took an enormous swig of his cup of water to steady himself, before accidentally crumpling it in his fist once he’d finished. “Wow, that’s… Jesus Christ Cassandra, your tight ass is fucking hot.”

He could see the pleased shiver work its way down her spine and turn into a slight wiggle of her backside, prompting him to move in instinctively behind her, hands hovering in the space inches over her smooth, covered ass flesh. Licking his lips, he leaned in, pressing his mouth as close against her earlobe as he dared. “Cassandra, I want you to know, I’ve wanted to palm your fuckable ass so goddamn bad, for the entire time that I’ve worked here.”

His icy boss bit her lip, suppressing a moan, glancing back at him momentarily. “Well? What’s keeping you?” She said, somehow managing to sound impatient and demanding while at the same time bent over a table, practically grinding her ass into his crotch.

Josh didn’t need another ounce of invitation, leaning back and smacking both hands down on either panty-clad cheek with a resounding slap that momentarily cut through the idle chatter Kelly and Gabriella had fallen back into.

“Woo, go Josh!” Kelly cheered, raising an enthusiastic hand to the sky. “Giving it to the boss, the old fashioned way!”

“And n-nice job to you too, Cassandra.” Gabriella said with a nod. “It’s b-big of you to let him indulge like this.”

“Well, you know what would really be the ticket—” Josh said, squeezing and kneading her amazing ass, getting his fill of its texture and slight jiggle while its owner squirmed underneath him, “—is if you let me spank you.” Taking a step back, he looked to the other women, bright-eyed and practically cheering him on, then back to Cassandra, glancing back over her shoulder with a few strands of hair lingering over one eye. Blowing said hair out of her face, her tongue proceeded to make a slow circuit around her lips, followed by her bottom lip disappearing behind her front teeth. “If you think you’re man enough.”

That was all the encouragement Josh needed before his hand was already up in the air, before he brought it down with a hearty smack that caused the middle manager to moan out in a combination of pleasure and pain. That’s for always denying my vacation time! He brought his hand down again, the noise causing Kelly and Gabriella to start slightly before they let out a series of whoops. That’s for not taking any of my sick days seriously! One more slap, underhanded this time, impacted hard enough to make Cassandra jerk into a stack of conical water cups. And that’s for being such an unattainable piece of hot ass all this time!

Josh finally stopped, panting, feeling the fire in his gut slink away to somewhere lower. Reaching forward, he tenderly rubbed one of her no-doubt-sore ass cheeks, the redness extending slightly from behind the covering of her underwear, gradually turning the motion into a light, soothing fondle before he leaned in to whisper into her ear once more. “You stay right here, I’m going to be right back.”

“You better.” She said simply, leaving a satisfied smile on his lips while he took a few steps back and pulled out his phone. Time for the main event, he thought with no small amount of a rush, and began typing.

• Female bosses in an office environment feel that it is their duty to sexually relieve their horny male employees, and take great pleasure in doing so.

Josh had just finished as a shrieking girlish “Ooooooooo~!” rose in tandem behind him, and he turned to see a sight straight out of his fondest wet dreams.

“Relax, ladies.” Cassandra was saying, slipping her fingers underneath the waistband of her lacy panties. “I think we all knew where this was going.”

Josh’s heart almost beat out of his chest as his no-nonsense boss’s bare ass was slowly revealed to him in all of its glory, perfectly straddling the line between muscle and fat to make it buoyant enough without losing any of its definition. As the panties finally fell around her ankles, she made to kick them back, aiming for the rumpled mass of her skirt—but missing entirely, and pitching them fairly close to Josh’s feet instead.

Staring down at the fluid that had already collected inside of the lacy garment, he tried to gulp down his arousal long enough to add one, final cherry on top of his sexy **** sundae.

• Despite having the same status and power as their male colleagues, female employees in an office environment have derogatory and sexual names for titles, which they nevertheless wear with great pride.

There, he thought as he slid the phone back into his pocket, we’re permanently even now, and I can just relax and enjoy this.

“Josh,” she said, in a voice that almost made him seize up from reflexive anxiety, “hurry up and get over here, we all have other things to do.” Despite her words, her familiar dismissive tone was softened by an edge that was almost… flirty? “Consider that an order, straight from your Queen Skank.”

He couldn’t get his pants off fast enough.

He seized her hips, his length momentarily sliding up into the smooth expanse of her butt cleavage, before he reared back, lined up, and held on. He only dimly registered that Kelly and Gabriella were watching with rapt attention in the seconds before he plunged in, taking her down to the hilt before their hips collided together with a meaty clap and a mutual groan.

“Ffffffffffuck…” Cassandra groaned out, her hands bunching up the blue plastic tablecloth into either fist as her hands clenched shut.

“Fuck is right,” Josh moaned, before pulling back, dragging nearly his entire length out of her wet, dripping passage, before plunging it straight back in. His rhythm was sloppy, being out of practice for longer than he cared to admit, until Cassandra managed to grip the far side of the table and use the leverage to hump back against his thrusts in a triumph of slapping flesh.

Josh glanced over at Kelly and Gabriella practically rubbing themselves at the sight, Kelly anxiously squeezing her legs together even while Gabriella’s hand stuck seemingly glued to the front of her mouth, the limb almost completely unable to hide her growing blush or her wide eyes that couldn’t seem to look away.

“I really shouldn’t have stayed to watch.” Kelly groused, rocking from side to side in idle sexual anxiety. “Now I have to hope that Kevin will fuck me half as good as that tonight!”

“T-tell me about it.” Gabriella murmured, lowering her hand enough to be heard. “Between all the perks, the responsibilities, and the sex, I kind of wish… that I was a Queen Skank already…”

Josh blinked, suddenly understanding that his last commands probably had more side effects than he’d thought. “Hey,” he grunted, moving his hands from clutching Cassandra’s hips to pressing into her magnificent ass to better control their rhythm, “this is going to seem like a really weird, urgh, question, but what are your, mmmmmm! Your, your job titles again? Officially speaking?”

Kelly and Gabriella blinked in unison, letting him know that this was, indeed, a strange question, before cocking their heads to the side in idle thought.

“Well, you should probably know already,” Kelly said, “since it means you get to boss me around all the time, but I was hired on as the company’s Virgin Pussy. You know, because I’m new?”

“Yeah,” Gabriella nodded, “and I actually got a little bit more responsibility not too long ago, including some stuff with firing people, so my official title is Head Bitch.”

“Oh, congratulations!”

“Hey, thanks.”

Their words were almost too much for Josh, and compared with the sheer erotic excitement of the past few minutes, he could feel that he was going to blow, and very soon. “Don’t worry, ladies,” He said, purposefully slowing his rhythm to slap Cassandra’s ass on every downward thrust, causing his uptight boss to moan like a common hooker while he prolonged the inevitable, “I’m sure that with a lot of hard work, and dedication, someday you’ll both be Top Whores!”

Kelly and Gabriella’s eyes widened with shock, stunned by the sudden compliment, before Kelly took an excited step forward. “You really think so?”

“Oh, I hope you’re right.” Gabriella said, clasping her hands in front of her with a glimmer in her eye. “I’ve always wanted to be a Whore!”

That did it, and Josh did his very best to pull out of Cassandra as quickly as possible—managing the task at the last possible second, the final clenching squeeze of her own spasming pussy giving his cock’s head the stimulation to spurt out onto the back of his boss’s (probably fairly expensive) business blouse. He came once more, twice, then let out a soft dribble onto the ground, sagging in place as the loss of adrenaline left him panting while he took a few steps backward from his dripping boss.

For her part, Cassandra slid to the ground, panting wildly with a head full of tousled hair, but a look of satisfied sexual contentment spreading out across her features nonetheless. Reaching up, she idly grasped at one of the scattered water cups, before raising her other hand to work the handle and fill it up. “So,” she said, just before bringing the rim to her lips, “how was it?” She asked, the rim of the cup just barely managing to hide her slim smile.

“I can honestly say,” Josh said through his panting gasps, a truly satisfied smile of his own spreading across his features, “that you’re the best Skank I’ve ever fucked.”