Cassy's Awakening Ch. 07

Synopsis : Having already gone far past what she'd ever thought possible, Cassandra is forced to push herself to the limit. Will she continue to tow the line for Jane, or has the week proved to be too much for her to handle?

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

As always, I've done my best to incorporate as many people's suggestions into this chapter!

Have received a lot of PM's, and comments, and am doing my best to craft everything into the story while pacing things out enough along the way (as well as setting up for future fun!) :D

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

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Chapter 7 : Multitasking

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"Mistress -- uuehuh - you seem -- uuehuh -- you seem tense today - uuehuh-" I grunted, bracing my hips as they thudded against the heavy wooden desk.

My white knuckled hands gripped the sides of the desk, but the repeated impacts from behind me still managed to nearly push me up and over the desk top.

"It's been a busy morning, Slut," Jane's strained voice came through gritted teeth. She really was tense this morning, I thought, and she was thoroughly taking it out on my poor ass.

"Yes ma'am-" I gasped, "It's just -- ehuh- it's just-you don't usually need to use me quite -- euhuh- quite so early-"

I grit my teeth.

Jane didn't usually use my ass like this until later in the day. It wasn't even noon yet, and she was really giving me a pounding.

"Well, what can I say-" Jane panted, thrusting into me mercilessly, "Pounding your tight ass is a great way to blow off some steam, and today I thought I could use some early release. That okay with you, Slut?"

She bottomed out the dildo, slapping the base of the sex toy against my parted ass and slamming me against the heavy desk.

My eyes rolled up into my head.

"Yes ma'am-" I answered her as I returned to my senses, "Whatever I can do to help you relax, ma'am!"

We were in my office. Well, my former office. It belonged to Jane now.

Let me rewind a bit, and recap.

Since my initial return to my job at Illuminate Media at the beginning of the week, my work life had been turned upside down.

My tumultuous first day and a half had been filled with defiance, rebellion and reluctance. Too slowly had I learned the new rules, and it had culminated in my unceremonious demotion beneath Jane.

I'd acted out, and without even breaking her stride, Jane had busted my sorry ass down more than a few pegs. It had been a wake up call.

After that, I'd been... somewhat broken in, to say the least. My defiant attitude had taken a back seat to my survival instincts. I'd learned not to challenge Jane's authority. Every time I had, it had ended in disaster, and I was a quick learner.

Obviously, that had been the precise lesson Jane had been attempting to teach me. When I obeyed her, things went well for me. Or at least, they didn't degrade as quickly.

To put it simply : If I touched the stove, I'd get burned.

So I'd stepped into line, out of necessity. I mean, what else was I supposed to do?

I had accepted my submissive role, obeying her every order and instruction as if it were law. In the office, I acted as her personal assistant/secretary/go-fer.

I'd swapped offices with her, giving her my much larger space and taking over her smaller, though still nice, quarters.

Folks around the office had their questions, of course. Why was I -- the former office Bitch -- so graciously accepting my role as Jane's underling? Why was I so eager to give up my prized office, and my jealously guarded client list, to someone I'd formerly hated?

The questions flew, but Jane dealt with most of them.

Presumably, I was the subject of much scorn and behind-my-back jokes...

But I couldn't really deal with that on top of everything else that I was managing, so I had to simply roll with the punches.

Aside from my role in the office, my body was also at Jane's beck and call. My ass was her toy, my tits belonged to her ; everything I had was hers to use as she saw fit, and she made to sure to use every inch of me.

At home or at work, I'd learned to drop to my knees at the snap of a finger. My mouth was her personal masseuse, and I'd grown quite adept at pleasing my secret Mistress.

The remainder of the week had gone much smoother for me.

Well, smooth is a relative description. When you're used to the things I've become accustomed to, even the ludicrous can seem sane.

But I'd avoided any further punishment. The worst I'd gotten was a few spankings and a couple of time-out sessions with my tongue tucked between Jane's legs.

"Did you get that report for Claire done?" Jane grunted, reaching down to grab my tossed blonde ponytail and give it a rough tug.

"UuheHUH-" I groaned as Jane slapped up against my ass and yanked my hair back at the same time, "Yes, ma'am! Finished and submitted to -- uuhehuh - accounting!"

I heard Jane let out a laugh, and it was no wonder why.

I sounded ridiculous, trying to speak professionally while getting my ass hole pounded over my former desk.

Jane was behind me, wearing the infamous double sided strap-on I'd picked out at the sex shop. She looked good today, I had to admit. Her dark bangs were sleek and straight across her forehead, and her outfit -- a blazer from my own personal collection -- gave her the sort of professional vibe I'd once aimed for.

I was quite the opposite.

Jane had me bent in half, my tits pressed onto the expensive surface of the desk.

My skirt, a short, dark pink number, was flipped up over my hips, allowing Jane's strap on to firmly lodge itself into my naked, waiting ass without resistance.

Every time she pounded into me, I'd let out forced squeal.

"You're sounding like a little squeak-toy again," Jane giggled, continuing to fuck me mercilessly as she laughed, "You enjoying this, Pet?"

"Uuhe-huh!" I squeaked, "Yes -- yes ma'am-"

"You feel tense as well, Slut," Jane continued to yank back my hair as she rode me, "You keeping up with your work load?"

"Yes ma-uuuhe- yes ma'am-" I felt a spittle roll down my lips as I tried to answer my Mistress. I took a risk and let go of one side of the desk to wipe the spit from my chin.

"Hands out," Jane reminded me immediately, and my hand shot back into place.

"Sorry ma'am," I answered hastily, "I was drooling..."

"That's okay, Slut," Jane said, "You can clean up the desk afterwards."

I closed my eyes, resigning myself to drooling onto the desk.

I'd be a mess after this, I knew. I was already sweating, and drooling, and leaking from my cunt down to my high heels...

As if I didn't already have enough to take care of -- now I'd have to spend a bunch of time fixing myself up!

"Well I'm glad ONE of us is keeping up," Jane said, thrusting against me, "I'm in over my head dealing with all of your shit. Honestly, Cassy -- how you ever manage to stay afloat with all of your little side hustling is beyond me. It's a job all on its own!"

I groaned, thrusting back against Jane, giving her as good a fucking as she was giving me. I realized I was clenching not just my ass, but my cunt as well, straining in my attempts to keep myself from cumming.

It was automatic behaviour at this point. I wasn't permitted to cum without permission. This was Jane's time to blow of steam, after all. Not mine.

"I'm sorry ma'am," I said, "Thank you for taking care of my affairs- eehuh!"

It was pathetic that I had to thank Jane at all.

Despite the fact that she'd taken on all of my clients, projects and administrative jobs, Jane had hardly taken on any additional work for herself. She let me do it all -- from the reports to the nitty gritty detail work.

In between coffee runs and fuck-sessions, I was still performing my usual role at the company. In honesty, I was performing much more work than I ever had before. Christ -- I was barely keeping up, hopping from one job to the next, keeping my Mistress happy while back flipping around in an attempt to keep performing at a top-level.

It was an interesting arrangement Though Jane was technically above me now, she'd mercifully allowed me to keep most of my duties. She hadn't even touched my salary, or my commissions -- which had been a worry of mine initially.

It seemed all Jane had actually wanted was for both of us to know who was in charge. Symbolic ownership, sort of speak. Sort of "If you step out of line, things will go badly for you".

"I almost fucked up this morning," Jane said, "A big deposit came in to your personal account from Westler&Sons, I almost called accounting about it. Thought it was a mistake. Wouldn't my face of been red?!"

I blushed, suddenly nervous.

"But I figured it out. Who would have thought embezzlement was so damn complicated," Jane laughed, "Thank God I have your sexy ass to pound at my beck and call, or I'd go insane trying to figure out your spider web of nonsense!"

I sunk into myself.

Of course, Jane wasn't actually talking about embezzlement. Technically, the deposit from Westler&Sons would have fallen under the 'bribe' category.

This was the OTHER side of my job that Jane now controlled. The kickbacks. The 'donations' to my personal account. The quid-pro-quo arrangements.

I had never considered any of what I'd done to be 'wrong'. I worked damn hard for this company, and for my clients. I got results -- more than anyone else on my floor, OR the floors above me! So what if I profited a little on the side? If anyone deserved it, it was me!

Especially now that I was performing so many extra duties!

I grit my teeth. Jane had plunged in extra deep this time, pummelling my sore ass with a vengeance.

Unfortunately the company, and the law, would see my little 'rewards' very differently. Jane was well aware of the leverage she had over me, and to no surprise, she'd kept things running exactly as I had.

My nefarious dealings were still well under way, only now, Jane pulled the strings. Illegal deposits and unethical deals poured into my private accounts, exactly as I'd set them up to do. But now Jane was in control. She was the only one who was shielding my private world from the light of day.

It was yet another string she used to maintain her dominance over me. This, in addition to the photos and videos of me fucking myself senseless all over the place, made her control nearly total.

In short, I'd dug myself into this hole, and now I was living in it. That Jane had only gone as far as she had with me was due only to her own mercy. She could have destroyed me utterly if she chose.

I was lucky, if anything... and I found myself perversely grateful to her for keeping things as reserved as she had.

"Ugh, I'm beat," Jane said, sliding the strap on my from my ass and slumping backwards into her plush office chair, "Your ass is great for relieving some stress, but it's a ton of work to pound that tight little hole. Come finish things off, Cassy, it's not fair that I do everything."

My mouth was hanging open, and the sounds of my heavy panting filled the room.

I thanked the Gods that Jane had locked the door. She always did for these sorts of sessions -- yet another thing I was grateful for.

I was loud as hell when I was getting fucked in the ass, as it turned out... but Jane took care of me, ensuring I wasn't unnecessarily exposed.

"Yes, ma'am," I said, slumping off of the desk, and twisting around in front of her.

Jane was leaning back in her chair, her legs parted and her work skirt hiked up over the rigid strap on that pointed up at me.

"I'm glad you're enjoying my ass, ma'am," I forced a smile, clenching my trembling cunt. God, I was right at the edge, almost unable to move myself without exploding.

She put her arms up, behind her head, clearly expecting me to perform my task and please her. I moved quickly so that she didn't have to wait long.

Raising my leg up, I straddled over her on the chair. I slid my foot over the arm rest, and pulled the rest of my body up onto the chair with her, until I was practically sitting in her lap. My muscles strained as my parted legs hovered over the thick purple dildo.

The chair groaned with the weight of both of us on it, but I knew it would hold. We'd tested it like this many times already...

"I'm sorry you're so stressed out..." I purred, leaning in to gently kiss Jane's lips, "Thank you for working so diligently to sort out your Slut's messes... I'm ever so grateful to my wonderful, sexy Mistress..."

Jane smiled. She loved it when I talked like a little a dirty little ditz. I was getting good at this.

I gyrated my hips gently against her, pushing down onto the tip of the thick strap on. I knew she could feel the pressure of my ass pushing down on the dildo that was lodged up inside her own pussy.

I wanted to get things rolling quickly. Not only was my body craving the continued pleasure of the strap-on, but my work-mind was racing as well.

I had so much to do today. After this, Jane would probably want me to fetch her a snack from the break room. Beyond that, I had reports and projects to manage, plus clients to call, people to get a hold of-

But I knew better than to rush my sessions with Jane.

Jane came first, I told myself. No matter what. No matter how run-down I may feel, she had to come first!

"Cassy will make her Mistress feel better..." I cooed, pressing my ass hole against the strap on. I felt my tiny hole give way to the thick shaft, and I sat further down, pressing it up inside of me slowly but surely.

I grunted, feeling the penetrating toy shove further and further into me. It was electric, sending jolts of pleasure up into my brain with every inch I slid down over it.

My parted pussy was practically gushing, running down onto the base of the sex toy. My mind was on fire, unable to focus on anything else but the pleasurable mission at hand.

But in my mind, I repeated my well learned mantra :

My Mistress needed relief. I was to provide it.

I began to slide my ass up and down on the strap on, riding Jane's lap on the chair. I grunted with every thrust, feeling beads of sweat forming on my skin.

My tight white shirt was already pressed taught against my tits, giving Jane a nice view of my pierced nipples underneath.

Jane sighed, and I saw her cheeks begin to turn pink. She was enjoying this. It made me blush as well. I felt a swell of pride that my Mistress was enjoying my efforts. My poor ass worked so hard to please her, I thought.

I increased my tempo, rising up only to thrust down onto her lap again.

I was pounding the hell out of my own ass, but I knew she was getting a decent fucking as well -- and that was all that mattered.

"Good girl," Jane said, closing her eyes and relaxing as I rode her, "I can feel the stress melting away-"

The phone on Jane's desk began to ring, interrupting her.

Shit!

Jane opened her eyes, looking rather annoyed at the sudden distraction.

Without breaking my stride, I wrenched my body back, reaching towards the desk and grasping at the phone before it rang a second time.

"Miss. Scott's office!" I answered hastily, holding the cordless phone to my ear as I desperately tried to continue riding my Mistress, "How may I help you?!"

Jane smiled, and closed her eyes again.

Yes! I continued to pound down against her, forcing the grunts and moans to stay tucked into my mouth as I listened over the phone.

I could do this, I thought. I'd keep my ass wrapped around that dildo as firmly as ever -- no matter what distractions I was facing! I could keep Jane happy -- no matter what! I needed to!

"I'm sorry," I said into the phone, clenching as best I could to stop myself from cumming as I rode Jane, "Miss. Scott is unavailable right now, may I be of any assistance?"

I blushed, feeling like an imbecile. The truth was I HATED answering Jane's phone calls, yet she made me do it at every opportunity. To my chagrin, I was getting very good at it, often snapping up the receiver before it even finished with the first ring.

I listened to the line for a moment, wincing as my ass engulfed the thick shaft beneath my thighs.

"I'll let her know," I promised the voice on the other end. It wasn't an important call. Just some random prick down in the tech department, calling to confirm he'd completed some task or another.

Actually, I considered for a moment, he was actually calling to confirm he'd completed a task for ME. But of course, all of my jobs were forwarded to Jane now...

"Thanks for the ca--aaah-all!!" I groaned, slamming down the phone as Jane's hands gripped my tits.

She was cumming. I could feel it. Her hands squeezed my breasts, pulling me in as she orgasmed under me-

"You're becoming such a good little employee," She said, kissing me on the lips as she came, "And a wonderful pussy-masseuse, whether it's your mouth or your ass that's doing the work."

I beamed, despite the humiliating compliment.

"I feel much better," She said, pushing me up off of her. I groaned reluctantly, feeling the strap on mercilessly slide out of my tired, sweaty ass.

"I'm glad, ma'am," I said, straightening out my tiny skirt as she did the same with her own, "Do you need anything further, or should I get back to work...?"

I was flustered as hell, craving release of my own... but I knew better than to ask for such a thing. I'd hardly earned a reward yet today, and I hardly had the time anyways.

Priorities, I reminded myself. Work had to come before my own desires... because my work was now Jane's work, and Jane was number one!

No matter how much I wanted to beg for a little play time for myself...

Jane kicked off the strap on, tossing it into the bottom drawer of my former desk.

"You eager to leave, Slut?" she said, cocking an eyebrow.

"N- no ma'am!" I answered quickly. I was fixing my makeup in a tiny hand-held mirror, doing my best to get rid of my freshly fucked look, "I -- I just have a ton of work to do- I've got reports, and projections to write up, and-"

I snapped the mirror shut and faced Jane with a forced smile, trying to look nonchalant.

Jane clearly didn't like my efforts to slip out.

Shit!

I kept a smile on my face, trying not to look as beleaguered as I felt.

She waited an agonizingly long time before responding to me.

"You're looking like you're running on empty, Cassy," Jane said coyly, "Any complaints you need to discuss?"

My cheeks went white.

"No ma'am!" I said at once. I knew what Jane was getting at, but I wasn't falling for THAT trap. I wasn't about to complain about a single thing, come hell or high water! I wouldn't risk more discipline just to vent my stupid, pathetic inner thoughts!

"I'm more than capable of keeping up with my workload," I promised, sounding less convincing than I'd tried to.

"Well, at least you're getting used to doing some actual work," she said at last, and I blushed. "We'll make an honest girl out of you yet, Sassy Cassy!"

Her comment cut me deep.

"Yes ma'am," I answered as I knew I ought to, "Thank you for all of your efforts, Mistress."

Humiliating.

I was a very diligent worker, I thought! It wasn't my fault that I spent most of my time fetching her coffees, or acting as her personal de-stress fuck toy! If I had more time to do my REAL work -

"I think I might take an early lunch today," Jane said, "It IS Friday and all, and I've put more hours of work in this week than you usually do in two."

I blushed, once more feeling the deep cut of her words.

Jane was exaggerating, of course, but as much as I hated to admit it, she had a bit of a point. Not in terms of hours -- we worked the same hours, of course -- but with me at her beck and call, she'd managed to increase our combined productivity substantially.