Cathy Sleeps Her Way to the Top

"... You promise?"

Mister Richards, Cathy's manager, whipped out a Pay Adjustment Approval Form with a big red sticker at the bottom.

"I just need to sign the dotted line and you'll get your raise tomorrow morning." He said with a smirk. He was getting off just on the fact she was considering it.

Cathy had just lost her weekend job. It was a crappy, soul-sucking place but she couldn't deny the pay was right. And as a fresh graduate, she couldn't exactly turn away the extra money.

... could she?

Cathy had one last look around the empty office. She'd always hated girls like that. Who got promoted not because they were good at the job, or put the most effort in, but because they flirted with the boss.

Although Cathy guessed this was a little more than flirting. One quick indiscretion, and she would get her weekends back.

Looking up at Richards, Cathy nodded, and unbuttoned her shirt.

Cathy had no idea what she was doing, but Richards didn't seem to mind. He was already hard when she unzipped his fly, and after a minute or two of pawing her breasts Cathy could taste a bead of salty precum on the tip of his member.

Running his fingers through her hair, Richards unloaded into her throat. "Swallow," he groaned, as if that hadn't been the deal all along.

Once they were done, Richards signed the paper with a flourish, and dropped it into the IN box of Dave from finance.

Cathy did her best to put her bedroom hair in order, and they spoke no more about it.

For a while...

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A month later, Cathy stared at her bedroom ceiling for the third night in a row. It was Saturday, the third Saturday she'd had free, and she'd managed to bring another guy home from the bar.

Nathan was... fine. He clearly worked out, he'd mentioned it enough, but after they'd finished he'd gone right to sleep and left her to rub her clit until she was satisfied. Ironically, night she found herself thinking of was...

In the dark, Cathy rolled over. Nathan had a tattoo across his back she hadn't noticed before. Wrapped around the silhouette of a woman on a pole, it read, "If you're gonna be a slut, you might as well get paid for it!"

"Douchebag," Cathy said to Nathan's sleeping form.

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Bra off, shirt unbuttoned, panties pushed aside, bouncing up and down on Mr. Horn's dick to the rhythm of Careless Whisper on the car radio, Cathy marveled at how easy it had been to seduce the Head of Sales.

Despite the image of a conservative family man, all it took was a few days of innuendo and a push-up bra for him to come to her with an offer.

"God, you're so big!" Cathy moaned experimentally, and she felt Horn twitch inside her. A few more compliments like that, Cathy thought, and she could finish him off!

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"Good morning, Simon!"

"Morning, Cathy." Richards said glumly. He still wasn't sure why his department needed two leads, but it set his teeth on edge to share the spotlight with a girl fresh out of college.

"Mr. Horn wanted me to give you these forms," she went on, "be sure to get them done by tomorrow morning. Oh, and Horn and I are going to be out of the office the rest of the day, we're meeting with Johnson from Regional."

"... Oh, good."

"Call if you need anything!" Cathy called over her shoulder as she sashayed out of the office.

Her lips weren't the great anyway.

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"Oh, I've never done this in an office before!" Cathy said honestly. Technically she'd only done it on the sales floor.

"Don't worry Cathy, It's just like in a bed," Johnsaid cooed into her ear, "I'll teach you."

Pulling her pink panties down around her ankles, Cathy leaned forward onto Johnson's desk and spread her legs, flattening her breasts against the mahogany.

"Are you sure no one's going to walk in on us?" She wondered aloud, but with an edge of excitement.

"The door is locked from the inside, we can take as long as we need!" Cathy giggled at that.

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"Gentlemen, this is Cathy!" Said Johnson, and gestured to the young blonde behind him, "I discovered her in one of our warehouses last month and I'm bringing her up here to help out.

"I hope to see a lot of you!" Cathy cooed, and let her eyes settle on the Vice President of Sales.

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Cathy pulled her bra off over her head, spilling her pale white breasts into VP Peterson's face. Enjoying the sight for only a moment, Peterson turned her around, pulled out his cock, and bent her over.

"Oh fuck," she moaned as she felt his cock enter her. "Don't hold back, Mister Peterson. Give it to me hard."

Cathy braced herself against the cool glass of the office window, free for all to see except for the twenty storeys separating her from ground level. Anyone with the right set of binoculars could have looked up and seen her tits gently bouncing against the glass, except for when Peterson reached around to grab them and tweak her nipples.

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"Everyone, I think you've met Cathy!" Peterson coughed as he walked into the Executive Lounge. "If I'm ever out of the office, feel free to find her instead. She's got all my files."

"Thank you Mr Peterson!"

"Oh and Cathy, don't worry about getting to know everyone right away. With how much time you'll be spending answering emails, you'll learn everyone's names in no time,"

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"Oh Roger..." Cathy called, and let her bikini bottoms float away, leaving her totally nude in the orange sunset.

Roger eagerly stripped off his trunks and dove into his pool, already rock hard.

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"Oh John," Cathy gasped, then giving his member a long, sensuous lick she added, "are you close?"

"I'm close!" John panted, "Don't forget to swallow, I just had this carpet redone!"

"Of course, sir!" She teased and made an O with her mouth.

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"So Ryan," said Cathy, "did I ever tell you I paid my way through college this way?" Flinging her bra over Ryan's head, she strutted around the pole, projecting confidence.

Inwardly, she hoped that two weeks of pole dancing lessons at the Y were enough to fool the executive.

Hedging her bets, she added, "I'm a little out of practice. Maybe if I gave a private show, it'd come back to me?"

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"Thomas! Thomas! Right there! Don't stop!"

Thomas cupped her chin and said, "Be as loud as you like, baby! I sent my whole department to Applebee's for meeting their quotas."

Cathy felt herself cum at that, and screamed so loud she worried IT might hear in the basement.

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"Morgan- Oh!" Cathy started mid-thrust, covered her breasts and tried to disappear into the white leather interior of the restored convertible.

Morgan laughed, "Oh that's my gardener. He waters our plants while we're out."

"... You're not worried about him hearing us?"

"He's here on a Visa." Morgan shrugged.

"Oh, okay!" Cathy climbed back into Morgan's lap, guiding him inside her with a gasp.

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"Happy Birthday, Charles..." said Cathy coquettishly, and stepped out of the hotel bathroom, "It's time to open your present!"

Lounging on the bed, Charles pulled on the ribbons holding up her red dress until it pooled at her feet.

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"Honda-sama!" Cathy cooed, "Tōkyō made 24-jikan no furaitodesu."

Sliding between the executive's legs and slowly undoing his belt, Cathy thanked her lucky stars, and not for the first time, that these private jets had so much leg room.

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"Dear Cathy,"

How could she let this happen?

She'd been so careful. She'd done everything right.

Cathy had survived three investigations from HR, two mergers, six rounds of layoffs and the entire Recession.

She'd always kept her bosses apart, always kept them happy, never burned a bridge if she could help it, kept herself in shape, fucked like a rabbit in catholic school, and never once let a VIP leave with an unsucked dick.

She'd even made a point of being on good terms with the wives! Hell, she'd been invited to a naughty little threesome for Mr and Mrs Jameson's anniversary and never once let on that she'd been cleaning his cum off her tits that morning!

How had she been so careless?

"Happy Birthday to you!"

How had she let herself turn 30?

Smiling politely to all her co-workers, Cathy couldn't tear her attention away from the slice of sheet cake she'd been handed, fondant rose sliced neatly in half where Bernard from International Shipping (red panties, no bra, tell him his dick's big and swear like a sailor when you're under him) had cut it.

She could see it happening already. She was getting to be old news.

It had been weeks since Mr Gordon had pulled her into his office to "go over the returns", she'd had to practically beg to be the stripper for Ryerson's birthday last week, and the guy from IT had barely glanced down her top when she called him up to fix her computer.

"Cathy!" She almost jumped when she heard Gordon's voice (he knows you're fucking Michael, be sure to mention how much better he is), then almost jumped again when she saw who was standing beside him, "I don't think you've met Penny yet, have you?"

On Gordon's arm hung a pair of tits that let you skip the line at clubs, but Cathy forced herself to focus on the girl they were attached to.

"Hi, Cathy!" Big, innocent blue eyes stared up at her, framed by platinum-blond curls and bright red lips that didn't quite match her color. "Happy Birthday!"

Cathy took the extended hand and shook it limply. "You must be the new intern?"

"Co-op, actually! Mr. Isaac says I can start as soon as I graduate in six months!"

Did Cathy imagine it, or did Gordon's hand creep just an inch down Penny's waist? As the polite conversation faded into the background, Cathy came to the terrible realization no one noticed she'd stopped talking.

She laughed along politely with everyone else, refusing to let them see the pit that was forming in her stomach. Cathy had the feeling like her world was being ripped out from under her. There must be a way she could stop this, get rid of Penny. Maybe frame her for losing some important files, or "accidentally" send a wife home at just the right time to...

No, that was a losing battle, Cathy knew. She could easily get rid of the younger Penny, but there would always be someone like her to take her place. Cathy knew from experience just how many pretty young graduates were lining up to get onto the top floor. She had only kept ahead of them because she wasn't so naïve as to think they hired her for her degree.

Penny wasn't the problem, just a symptom of it. If Cathy didn't do something drastic, she'd be facing early retirement. Or worse, they'd shuffle her off to the 17th floor, under the Ethics Officers, spending all days writing reports for all the important people to promptly file away and forget about.

Cathy traded a quick smile with the Chief Ethics Officer. A large, elderly man who she knew for a fact hadn't been able to get an erection without Viagra since Bush was in office. She shuddered at the thought.

There had to be something else to keep Cathy in vogue. Something she could fall back on, or some way to make the Board see...

No, there was no way she'd dothat. She had never meant to dothat.That had never even been a viable option, just something she'd turned over in her head when she got fed up with lying to all the execs about how many time she'd cum.

... Although...

It wasn't like she was getting any younger. A working retirement would at least keep her busy. And I mean, if it didn't work, at least she could tell herself she did everything she could.

Still. To actually go through withthat... did she have it in her?

"Oh, and Cathy!" A word from Gordon brought her back down to Earth, "I was hoping you could go out to get us some more wine. I'd ask Penny to do it, but she's too young to drink."

A moment flashed in front of Cathy's eyes. One where she reminded him this was supposed to be her party. Where she screamed her head off about how his dick wasn't even the biggest in his age bracket. Where she exposed every exec in the office for their philandering, cheating ways to all their wives.

Instead, Cathy's anger hardened into a terrible resolve.

"Sure thing, Mr. Gordon!" Cathy rose to her feet. "White okay?"

Gordon shrugged, waved her off while returning to talking with Penny. "I trust you!"

"Thanks, boss!" Cathy sashayed out of the office, and quietly plotted *that*.

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"You want to do what?" the HR rep balked. A young, scrawny man barely three years out of college, the Board had stuck him on the top floor. It was very important that their HR rep had no experience or confidence, or else he might start to stand up to people.

"I want to head up this year's Teamwork Retreat!" Cathy shrugged, like it was the most normal thing in the world. "I think it would be fun!"

"It's... usually not." The rep said honestly. Even with his limited experience, he knew that the head of the retreat usually got the job because they'd pissed off someone important. He'd been doing it himself for the last two years.

"Well, I'd like to try it anyway." Said Cathy, "I have a place in mind."

The rep, shuffling in his desk, fell back on the only instructions he was ever expected to follow: "I'm going to check with the Board on this. They usually like to approve my choice ahead of time."

"Steve," Cathy said, and placed a hand over his as he reached for the phone. "No need to bother the Directors."

The rep had no answer to this. He wasn't used to people at work knowing his name. Cathy herself only knew it because she'd found his LinkedIn.

With a kick of her leg, Cathy shut the door to the closet HR had given Steve as an office.

"Why don't you and I just... hash this out here and now?"

With mounting surprise, the rep realized that for once, it wasn't his imagination that had Cathy taking off her shirt.

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"Alright everyone, thanks for coming!" Cathy called from the under a tasteless faux-wood totem pole, clipboard under her arm and a pink roller bag at her heels. "Thank you all for coming to this year's Teamwork Retreat at the Runnning Warrior ski lodge! I'm going to need everyone to check in with your credit cards! Don't worry, all drinks and food are taken care of, all you'll pay is a deposit for the room, which we'll reimburse you for!" With minor grumbling, the jet-lagged executives all filed in front of the desk.

"And once you're done that, I've got drinks and food in the bar!" And like that, the party all suddenly remembered Cathy existed.

There was no skiing on the Teamwork Retreat. It wasn't that kind of vacation. But no one had thought to mention it, because the open bar was always the main attraction, and Cathy had been sure to mention it prominently in all the emails.

What she had forgot to mention is that she'd told the bar that the group would need non-alcoholic drinks after 9:00. The company always started early, so they'd still be getting drunk, just not so drunk they wouldn't be able to wake up later. Or worse, forget the whole night.

Quietly ticking off a name after every executive signed in with their card and made a beeline for the bar, Cathy steeled herself. This was going to be the hardest night's work of her life.

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knock knock knock

"Go away!"

knock knock knock knock knock

"It's 3 AM! I've got the Do Not Disturb sign up for a reason!"

knockknockknockknockknockknock

"Oh, somebody's getting fired in the morning, I'll tell you that for- Cathy?"

Cathy stood in the hallway, wearing nothing but a towel, clutching an ice bucket, looking bashful.

"I'm sorry, Mister Michaels," she pouted, "I just went for some ice, but I can't remember which room is mine. I had so much to drink," she said it in an offhanded way, "please let me in? Before someone sees?"

Cathy pulled at the towel enough to uncover the tops of her pink areolas.

"Uh, yeah!" Michaels said, after a moment, glancing down the hallway to make sure no one saw. "Yes, of course! Come right in!"

Cathy dashed into her boss' room, and immediately got to work.

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"Oh fuck, oh fuck!" Cathy panted, gripping the lodge's red-and-black bed sheets, "Oh, you're so big Mister Michaels!"

"Oh, you're so tight!" Michaels grunted, thrusting into her from behind, grabbing her breast with his right hand, tweaking her nipple between his thumb and finger. "You've been waiting for this, haven't you?"

"Oh yes!" Cathy moaned, "I've wanted to do this the whole trip. Oh, you're so... yes, right there, right there!"

Quietly, slowly, almost imperceptibly, Cathy wrapped her long, tan legs around Michaels' waist. When she was sure he was nearly done, she grabbed his neck, and whispered into his ear:

"Come in me."

In her experience, that was enough to finish off most guys on its own. Cathy had been sure to get him almost there, but it never hurt to hedge her bets.

Sure enough, she felt Michael's hot semen spill out into her, and dutifully collapse onto the bed next to her.

"Oh, fuck! You're so-" he gasped, and post-nut clarity sunk in, "oh, shit!"

"Oh, relax!" Cathy said conversationally, "I'm on the pill. And besides, tonight is my safe day."

Michaels sighed, "Oh, phew."

"Can we cuddle a bit? I know we promised no staying the night, but since we're on vacay-"

Cathy was cut off by Michaels' quiet snoring. That was good, but it still annoyed her how these older guys would always check out as soon as they were done.

With probably more stealth than necessary, Cathy slid out of the bed, tied her towel loosely around her, and slipped out of the room, replacing the "Do Not Disturb" sign.

Cathy stopped off at her room just long enough to rinse the sweat off her and wet her hair. Harrison was one of the younger executives, only joining the company two months ago, and she hadn't actually had a reason to sleep with him yet, so this would take a more casual approach.

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"Cathy? Is everything alright?"

"Hi, Harrison," Cathy blushed, and pulled the towel tighter around her, which had the fringe benefit of giving her tits a nice, plumped-up look. "I'm really sorry, my shower isn't working. Do you think I could use yours? Just to get the shampoo out of my hair?"

"Yeah, yeah of course! Come on in!"

As he was living in the space betweenpolitely tipsy andhung over, Harrison did not think to ask why Cathy hadn't called the front desk.

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"Oh baby, oh baby right there, right there!" Cathy gasped as Harrison plunged into her, snaking a hand between her and the shower tile to get a handful of her boob.

The soapy water ran down Cathy's arched back and over Harrison's stomach and legs. She had her leg over the grab bar to give Harrison free access, and had managed to position the shower head in such a way that didn't make her feel like it was drowning.