Cassy's Awakening Ch. 05

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Cassy Returns to the Office.
15.9k words
4.75
30.6k
25

Part 5 of the 12 part series

Updated 01/24/2024
Created 07/19/2022
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Synopsis : Cassy returns to the office, hoping to reassert herself and regain some control of her situation. Her day is immediately derailed by Jane.

Author note : The following story is part of an ongoing, multi-part series.

Once more, I've done my best to incorporate as many people's suggestions into this chapter, and will continue to do so in future chapters!

This is a work of fiction. All characters, places, etc are completely made up, as is the plot.

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Chapter 5 : Return to the Office

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To say I was in a foul mood was an understatement.

I was livid.

I'd left my house in a furious mood, but when I'd pulled up to my reserved parking spot in front of the office only to find Jane's piece-of-shit jeep parked in it, it set me over the edge.

I'd recognized her vehicle immediately. It had been the same one she'd driven me home in last night... after our adventure at that infernal outlet mall.

As I angrily drove past it, relegated to taking one of the far-off parking spots at the end of the lot, memories of the last few days flooded back into me.

Fuck! What had happened over the weekend?!

I'd gone from living my luxurious life... to crawling around in my back yard under the blackmailing influence of my co-worker in the snap of a finger!

She'd even had me pierced as a reminder of her control over me!

My freshly pierced nipples were still sore, brushing up against the overly tight fabric of my shirt with every step I took through the expansive parking lot. By the time I'd actually made it to the door of the tall building, and into the elevator, it was all I could not to tear open my blouse and give my poor chest some needed relief.

Of course, I didn't dare.

I was on a mission.

Jane's reign was at an end. I had to put a stop to all of this.

The elevator dinged, and I got off at my floor.

Breathing in deep, I marched out and down the hallway towards the reception desk.

The receptionist, a blonde, timid girl named Stacy, was already at her post. As always, she stood as I approached.

"Good morning, Ms. Riley," she smiled at me, "You're looking lovely tod-"

"Stacy," I cut the receptionist off with a glare, "I'm not in the mood for ass kissing today."

Stacy's chipper face immediately sunk into a hollow, ghastly expression.

Good.

It was nice to remind someone who I am.

I am Cassandra Riley, I repeated in my head. I am in charge here.

"Stacy, fix your collar," I drove in my condescending tone with a disapproving glance at the woman, "You're the first person people see when they step off the elevator, and we don't want them to think they've walked into a barn."

Stacy's face was white, and she practically trembled as she reached up to fix her shirt collar.

In truth, her outfit was more or less fine. She was wearing a professional looking skirt, topped with a basic white button up blouse. It was cheap, but that could be expected with what I knew the receptionist was paid.

Still -- it never hurt to keep her in her place.

"Ma'am," Stacy piped up as I marched past her, headed towards my office, "I -- um -- Ms. Scott asked for you. She left a note for me to ask you to go see her soon as you arrived."

I stopped walking, feeling my breath catch in my throat.

"Jane needs to speak to me?" I asked Stacy, feigning annoyance in an attempt to keep the worry out of my voice, "What for?"

"I'm... um... I'm not sure, ma'am..." Stacy fumbled her words, clearly still nervous now that she'd had a taste of my terrible mood, "She just asked to see you and I-"

"OK, Stacy, enough," I said, rolling my eyes, "Just get back to work. I'll go find out for myself."

Fuck.

All morning, I'd been anticipating and dreading this moment.

I'd hoped I'd be able to at least make it to my office before speaking with Jane. At the least, it would have been nice to confront her on my own turf, sort of speak.

Whatever.

If Jane thought it was her place to summon me to HER office, so be it. It would be the last time she'd entertain such a notion.

I stormed through the halls of our floor, steeling myself for an inevitable confrontation. A few coworkers made passive attempts to engage me in conversation as I rushed past them, but I was in no mood to entertain their petty ass kissing and attempts to curry favour today.

I made it to Jane's door, and entered without knocking.

"Well, well... if it isn't Sassy Cassy..." Jane greeted me immediately.

My coworker-turned-blackmailer was sitting at her desk, but unlike Stacy, she didn't stand to greet me.

Instead, she looked calm, collected, and completely unperturbed by my obvious attitude.

She was dressed in her regular work attire, looking far more professional than she had over the weekend. Her dark hair was straight and proper, and her blouse -- though more revealing than my own, was decently modest.

"Jane." I said, greeting her by her proper name.

"Hm," Jane smirked, "I see we've forgotten our manners today. Whatever happened to 'ma'am'?"

I glared at her, and shut the door behind me.

"Jane-" I repeated her name, feeling a nervous twinge inside of me as I spoke it, "This is over."

I marched up to her desk with confidence.

"I'm done jumping through your hoops," I said sternly, "Your little game is at an end. I'll have no part in your sordid world any longer."

Jane continued to smile, and leaned back in her chair casually.

"Oh, is that so?" she asked me, "Funny, you didn't seem so eager to put an end to things yesterday when you were begging me to fuck your tight little cunt in a sex shop."

My face went red, both from anger and humiliation.

"I -- you -- you know I had no choice-" I blustered, knowing my words were weightless as I spoke them.

I'd indeed ridden Jane like a whore yesterday. She'd fucked me repeatedly in the outlet mall, and I'd eagerly begged for more along the way.

"That is over," I repeated, trying to keep my confidence, "You've had your fun, and got whatever revenge you think you're owed. But we're back at work now, and I've got a career to manage."

"Oh, Cassy," Jane said, still slumped in her office chair without the slightest look of worry, "I figured you might say something like that. Of course, I've already spoken to Isabella about your poor attitude this morning."

I smiled smugly.

This morning, my former gardener-turned-Jane's-henchwoman, Isabella, had shown up for her morning routine. She'd been set to shave, shower and dress me for work.

I'd sent her off.

"I am not employing that harlot as anything more than a gardener," I said defiantly, "She's lucky to even remain in that position, considering her behaviour over the weekend."

Jane laughed.

"She said you threatened to have her deported?" she giggled incredulously,.

I shrugged. It was true. I wasn't sure if Isabella was here legally or not, but I'd threatened her anyways.

At the least, I was sure the girl wouldn't want me making a fuss with immigration. I was powerful ; she was not. That was all it would take to make her life a living hell... and I needed the leverage to get her back in check.

"Cassy..." Jane shook her head at my defiance, "Are you forgetting all of your little secrets I know about? I have evidence of all of your wrongdoing. Embezzlement, improper use of company property, breach of personal accounts.... not to mention the other things you've been up to."

Jane flashed a wicked smile. Of course, I knew what she was referring to. She had loads of photos, and videos, of me in lewd, sordid situations. She'd recorded me fucking myself in this very office -- on the same desk she was now sitting behind.

"You won't use any of that against me," I replied, my voice wavering for a slight, barely detectable moment as I played my ultimate trump card, "Because it would ruin you too. If you tell anyone about my financial activities, you'll be incriminated for covering it up, and if you show anyone the untoward images or videos of me, they'll know you set up the whole situation."

This was it. This was the play I'd decided to make.

"In other words, if you destroy me, you'll destroy yourself too," I stated flatly, "You've got nothing, and your control over me is at an end."

Jane clucked her tongue, and continued to shake her head. Finally, she shrugged.

"OK, Cassy," she said, "I guess you win."

She reached to her office phone, and pressed a button.

"Stacy, can you come in here for a moment?" Jane asked, and immediately, the receptionist answered.

"Yes ma'am," Stacy's mousy voice sounded off over the intercom, "On my way!"

Jane clicked off the phone, and spun down behind her desk, pulling out a semi-thick manila folder from her drawer.

"Guess we're both going down," she said, setting the manila folder on her desk, "I'll get fired, for sure -- but at least I won't end up in jail like you."

I glared at her.

What the hell was she talking about?

There was no WAY she would burn herself like this.

"You're bluffing," I said, more confidently than I felt, "What's in that folder?"

Jane smiled.

"Everything I've got!" she said, tapping the manila folder with a finger, "Pictures, reports -- every shred of evidence that the Board of Directors would no doubt be very interested to see.

My face whitened.

She was lying. There was no way...

"You're my Bitch, Cassy," Jane said with a smug grin, "I told you before, I own you. So if you need to learn it the hard way... so be it..."

I grit my teeth, steeling myself against the temptation to open the manila folder.

I couldn't let Jane win this.

But if she was telling the truth...

The door to Jane's office swung open, and Stacy entered the room.

"Ah, Stacy," Jane said, finally standing from her chair and picking up the mysterious folder, "I've got a quick task for you. Can you take this envelope upstairs for me? Deliver it to the CEO's office, will you? It's urgent."

I stared, white faced, as Jane handed the folder to the blonde receptionist.

"Right away, Ms. Scott," Stacy said eagerly, spinning around to leave the room.

Fuck.

This was it -- the moment of truth.

"Wait!" I blurted out unexpectedly, quickly rushing to Stacy as she made to leave the room.

"Wait-" I repeated, snatching the folder from her, "I -- uh -- I've actually got to review this first... for um, I've got to clear up a few details before we send it up."

Stacy looked confused.

"Sorry for wasting your time," I said to her, "We'll uh -- I'll call for you if we need you further."

My tone implied dismissal, and Stacy understood the urgency.

"Yes ma'am," she said. She was obviously still confused, but nodded obediently, and slunk out of the room without further comment.

As soon as she was out, I flipped open the folder, and swore out loud.

"Pretty good stuff, huh?" Jane said, sitting back down in her plush office chair as I looked at the folder's contents in horror.

Everything Jane had claimed to be inside the folder was there. There were reports and written statements that I assumed had to do with my business activities, but more to the point, there were SO many pictures!

Pictures of me in every lewd position imaginable. On Jane's desk, on my lawn, on my living room floor. My legs were spread, my fingers shoved up each and every one of my gaping holes.

My face was visible in nearly every photo -- and in most of them, Jane was present as well!

"Like I said," Jane said, reading my shocked expression correctly, "I'll get into my fair share of trouble for all this, I'm sure. But I'll just go get a job elsewhere. YOU'LL be ruined for a life time... probably jailed for all of that embezzlement, and humiliated-"

"OK!" I practically shouted, snapping the folder shut and turning to Jane angrily, "I get it!"

My cheeks were burning red again.

I was enraged.

She'd won our stand off, and I knew it.

I couldn't believe the depths she was willing to go through just to get me under her thumb, but the truth was self evident.

Jane's willpower was stronger than mine. She was willing to destroy herself ; I was not!

I'd tried to out play her, and had failed.

And so... she owned me.

"You can keep that folder," Jane smiled, twirling a strand of hair in her finger as she watched me implode before her, "I've got plenty of back ups and copies."

I was speechless.

"Tell me, Cassy," she continued, "Were you Sassy enough today to put on underwear?"

I felt myself shrink on the spot.

"I..." I murmured, not sure how to respond now, "I..."

"I'll take that as a yes," Jane said, looking me over.

I was wearing my standard work attire. An expensive, designer-fitted navy blue blazer over a crisp white blouse and matching work skirt.

Of course, my outfit did include underwear.

"Take them off," Jane said, but when hesitated, she furrowed her brow and lowered her voice.

"You're already on thin ice. Take off your bra and panties right now," Jane added, "Or I'll page Stacy back in here, and you can take them off in front of her."

I couldn't believe this.

I'd given my little rebellion everything I had, and I had failed.

Jane was in control again. All I'd done is made things worse.

"OK..." I accepted my fate with a reluctant sigh. In a daze, I began to unbutton my top, "Just -- please! Don't do anything rash-"

Jane watched as I obediently opened my shirt up, one button at a time.

I felt as if I was outside my own body, as if my fingers were moving of their own accord as I undid button after button.

My chest began to spill out long before I reached the bottom of my blouse. I slid off my blazer, and my shirt, and unclasped my bra.

"Toss it into the trash," Jane ordered as I pulled the garment off of my naked, pierced tits, "Where it belongs."

I sighed, and did as Jane ordered. I flung my expensive bra into the waste basket next to her desk, and moved to put my shirt back on.

"Leave that off for now," Jane said, "I'm enjoying the view, and I think you owe me a little bit of an apology, don't you think?"

I frowned.

"I... I guess..." it was obvious Jane was waiting for me to answer her.

Knowing what she wanted, I arched my back, pushing out my heavy, exposed tits for her to ogle.

"I'm sorry..." I said with a meek whimper as Jane grinned, "I was stupid..."

My skin was tingling from nervous excitement. Despite my efforts to contain myself, it was obvious I was aroused. Even my horror at being so exposed in the office, my nipples were hard and perky between their tiny metal piercings.

I could hear murmuring voices and activity just outside Jane's office. I had to remind myself the door was still unlocked. Someone could come in at any moment and see my topless chest, and there was nothing I could do to stop it.

"Jump," Jane ordered, "I want to see those big jugs dance around!"

I was confused at first.

"You want me to... to jump?" I gave a small jump, and my tits bounced accordingly. Jane grinned, and I understood.

I jumped again, and my heavy, naked breasts smacked down accordingly. Jane kept smiling, so I jumped again, and again, hopping on the spot like an idiot while she ogled my sloppily bouncing tits.

"Tell me you're sorry," Jane said as I jumped up and down.

"I'm -- sorry-" I responded breathlessly, feeling the exertion begin to catch up with me. As I hopped, my tits bounced and jiggled every which way.

"Like you mean it," Jane repeated, annoyed, "You can keep jumping until I hear a true apology for being such a Sassy Cassy."

I groaned inwardly as I continued to bounce about. It was difficult maintaining my balance in heels -- but I managed. All I could think about was the precarious situation I was in.

At any moment, Jane's door could swing open... and I would cease to be Cassandra Riley forever.

"I'm sorry!!" I said earnestly, feeling pitiful but forcing myself to get the words out, "I shouldn't have been... been so sassy..."

I blushed, continuing to smack my tits against my body with every jump I took.

"I'm sorry for being Sassy Cassy," I said, knowing the only way out of this was to push through, "I promise I'll behave in the future!"

Jane grinned.

"I was stupid!" I said between the humiliating sound of my tits smacking about, "I was dumb to try to fight you. I should know better-"

"Alright," she said, "Stop jumping around like an idiot and bring those bimbo tits over here. Lean 'em on my desk like a good Slut."

I stopped immediately, and quickly darted across the room to Jane's desk.

Jane waved me down, and I obliged, leaning forward over her desk to let my tits dangle in front of her.

"See Cassy?" Jane cooed, reaching out to graze my tender nipples with her fingertips, "Isn't this better than being such a stuck up cunt?"

I was panting, more from exertion than from Jane's stimulation -- though the latter was definitely having an effect on me.

"Yes!" I breathed, brushing my hardened nipples against Jane's fingers, "I'm sorry I was a cunt-AAH!!"

Jane had gave my pierced tits a sharp twist as I'd finished speaking, causing me to cry out in a startled surprise. Immediately, I glanced over my shoulder at the door, nervous I'd been too loud.

"Better watch that mouth of yours," Jane smiled, and gave my nipples another delicate squeeze, "You don't want to draw TOO much attention to yourself!"

I whimpered, hating the situation I was in, but admittedly enjoying the feel of Jane's hands on my breasts.

Between my thighs, I could feel a growing heat. Bent double over the desk, my ass was stuck up into the air, and the lewd, submissive position was having just as much of an affect on me as Jane's tender caress.

"Stay!" Jane commanded me like a dog, withdrawing her hands and standing up. She put her hand on my back, pushing my chest down onto her desk, accentuating my ass-up pose. Then, she opened a drawer in her desk, and pulled out a heavy duty looking metal ruler.

Shit.

My eyes went wide.

"I guess you know what's coming next," Jane said, circling around her desk while keeping her eyes firmly on mine, "You've got to be punished for your little skit earlier."

I whimpered again, knowing there was nothing I could do to protest.

Jane moved into position behind me, and I felt the metal ruler slide in between my thighs.

"Part 'em," Jane commanded firmly, and I complied reluctantly. I could feel my work skirt sliding up my thighs as I spread my legs apart. The skirt was long enough that it didn't ride all the way up on its own, however, so Jane used the ruler to pull it up the rest of the way.

She pushed it up, over my hips, so that my bare ass was exposed to the room.

"Panties down!" Jane ordered.

I groaned.

With my chest still pressed down into the desk, I was forced to awkwardly reach back up up to my ass.

I grasped the thin strap of my white, silky panties, and struggled to pull them down over my rear end.

It wasn't easy -- especially with my legs parted so far apart. I was only able to yank the panties down several inches... but it was enough to expose my cunt and ass hole to Jane -- which I knew was all she really wanted.

"Good Girl," Jane praised my efforts, and immediately, I felt the cold metal of the ruler sliding up between the crack of my ass, "Doesn't this feel like a more natural position for you, Cassy?"

I glared down at the desk.

No, it did not! This was humiliating! Horrifying! Anyone could come in at any moment and see my naked ass!

"Yes!" I grit my teeth and answered Jane as submissively as I could sound, "Yes, ma'am!"

SMACK!

Jane had whipped the ruler against my ass, spanking me with a sharp crack before I could ready myself.

Immediately, I let out a surprised shriek.

"Quiet, Cassy!" Jane chided me, "Or someone might poke their head in!"

I practically saw stars. My ass throbbed from the surprise smack, and it was all I could do to cry out again when she smacked me a second time-