Cassy's Awakening Ch. 05

"Fuck-" I nervously began to pace around my desk, fidgeting with the felt pen in my hand.

Every step I took reminded me of my unbridled desires. My ass felt empty without the thick plastic marker. I'd gotten used to it stuck up inside me...

With shame, I realized I'd already made my choice.

But I couldn't force my hands to listen! I couldn't comply with such a ridiculous demand! I couldn't circle my poor, eager ass hole, and admit to Jane that it was where I wanted her to pay her attentions to!

Whimpering quietly to myself, I stepped up to the front of my desk, facing away from my door.

I took a deep breath, praying that what I was about to do wouldn't be the end of my career.

My door was unlocked. Anyone could walk in. I had to trust that Jane knew what she was doing.

It was surreal.

I bent over my desk, slowly, with no small trepidation. My ass was aimed at the door, and I reached behind me to flip up my ink-spattered skirt.

"Pick a hole..." I repeated to myself quietly, steeling my resolve.

I knew what I had to do.

If I wasn't convinced I was a whore earlier, surely this would seal my fate.

I considered circling my cunt. It would be slightly less embarrassing than admit I was so eager for Jane to play with my ass. Plus, I knew my poor quivering pussy would have loved the attention...

But no.

As I leaned against my desk, my ass poking up into the air, I knew what I had to do.

Still holding the uncapped marker, I reached back with both hands and parted my poor, tortured ass. I pressed the felt pen down, and while I held myself open with one hand, the other drew a thick, obvious circle around my ass hole.

The feeling of the ink tracing its circle around my ass was exhilarating. An ultimate mark of submission that sent shivers up my body.

I went over the circle twice -- and then once more, for good measure, surely leaving a dark, obvious ring around my slutty hole.

There. It was done.

Just as Jane had instructed, I'd marked one of my holes for her. I'd chosen my ass, like a good and proper slut, and there would be no denying it now.

I reached up, setting the marker down, and pressed my chest down onto the top of the desk.

As Jane had ordered, I presented my chosen, marked hole -- thrusting my ass up towards the door, and parting my legs just as she'd taught me to do.

It was over, I knew. Jane had won completely, now.

If she could get me to do this... to wait patiently, naked, in my office for her to arrive...

She could get me to do anything.

I was going to be fired. Somebody was going to find me like this, naked and exposed. How would I explain it?

I wouldn't be able to.

My mind screamed out to resist.

Stand up! I shouted inside. Cover yourself up! You can't do this!

But I didn't move.

With a shudder, I realized a part of me had indeed been trained into obedience. I feared another spanking session. I feared punishment.

But I also desired to please...

I knew if Jane found me like this, submissively following her orders to the letter, she would be thrilled.

So not only would I not be punished... but I might be rewarded.

I felt sick with the realization that I wanted a reward.

How depraved had I become?

Was I REALLY willing to risk everything in my life just for a quick, hard fuck?!

I'd never felt so much confusion in my life...

It felt like an eternity that I stood at my desk, patiently waiting for my Mistress to come into my office. Every second I waited, I considered standing up, and simply fleeing the building.

But something compelled me to say. Be it arousal, discipline, or something more ; I stayed at my post, keeping my marked ass proudly on display.

I jumped in fright as I heard the door click open.

This was it. The moment of truth.

I didn't even bother looking behind me to see who was entering. There was no point.

Either it was Jane, and I would please her with my performance, or it was somebody else, and my life was over. There was no time to turn back, and no excuses I could make. It was the point of no return!

Letting fate take the wheel, I arched my back, and presented my ass for my Mistress -- or whoever else was entering the room.

"Good GIRL, Cassy!" Jane's voice, and the relief it brought, practically brought me to orgasm right then and there.

Oh, thank God!

Jane clicked the door shut, and mercilessly, I heard her lock it.

"Oh -- thank God it's you-" I almost burst into tears of joy, "I was so horrified someone else would come in and see me. I can't believe I'm doing this -- we have to stop-"

"I see you've picked a hole," Jane said softly as she approached me, "Nice choice. I figured you were a bit of an anal slut. Your ass was practically vibrating after our little session earlier."

I kept my head down, too ashamed to look at her. My hands were stretched out, clutching the opposite end of he desk as I'd done in Jane's office this morning. In fact, I was in the same position as I'd been in when I'd received my spankings. It was almost poetic.

"Please..." I begged Jane as I felt her hands on my unguarded ass, "Please... just be quick, Mistress. I have to attend a meeting any moment, and if I miss it-"

"Oh, don't worry," Jane said sweetly, "You won't miss it."

I sighed in relief. So, Jane WAS going to have mercy-

"You'll just have to learn to multi-task!" Jane laughed, and finally, I looked back at her.

Oh. My. God.

Over her work-suit, Jane was once again wearing the strap-on we'd purchased at the sex-shop.

The large, purple dildo was jutting out proudly. The other end was tucked neatly under Jane's flipped up skirt, no doubt already tightly inside her cunt-

"Spread 'em!" Jane said, kicking my already parted legs further apart. I complied, horrified at the implication of what Jane was about to do.

She'd actually brought that monstrosity into the work place?! How had she smuggled it over here?!

Was she really going to use that this purple dildo on me here, in public?!

"I thought-" I whined, "I thought you were just going to tease mee--aaah!"

My mind went blank as Jane slapped the tip of the strap on against my unguarded ass.

"Wait!" I begged, "I can't- not now! Oh, please Mistress! Please ma'am! You're going to ruin everything I've worked so hard tooaaahh-" Jane wasn't listening, and soon, I wasn't able to coherently speak. She pressed the hard, rubbery blunt dildo against my ass remorselessly.

Already slick with wetness, my ass gave little resistance, parting eagerly to allow her to funnel it deep inside of me.

I grunted a guttural, pleasurable moan.

"Oh -- oh my fucking Go-" my mouth fell open as I spoke, and all I managed to get out were a few sloppy words. I was lost in arousal. I reached behind myself in a foolish attempt to stop Jane's thrust against me, but she simply pushed through my weak hands.

Jane didn't even pause before she began to slide further into me, and back out again. She was fucking my ass without delay... and it felt...

"Oh... yesssss...." I practically drooled at the explosion of pleasure, and snapped my hands back out to the sides to clutch the edges of my desk.

"Still want me to stop, Whore?" Jane asked, slowly gyrating in and out of my eager hole.

"No!" I immediately responded, "Oh God, Jane, keep going-"

Jane stopped, and my eyes went wide.

"Oh shit-" I realized my mistake, "I'm sorry. I meant Mistress! I'm sorry! I'm so duummaaah-"

She continued immediately, and my eyes rolled back into my head in delight.

"Have you gotten one lick of work done all day?" Jane asked, sliding the slippery shaft deep into my ass.

"N-no!" I admitted, "I haven't -- you've ruined every moment of myaaHH!"

"Well, then you REALLY shouldn't miss your meeting," Jane said, and without warning, she reached down to my office phone. While she fucked me, she pressed the intercom button, and dialed a number-

In the back of my mind, I knew I should stop her. But it was all I could do to hold on to the desk as she rode me.

"Ms. Riley?" A voice over the speakerphone caused me to jump in surprise. It was a male voice -- Mark's, by the sound of it, "So glad you could join us. We almost got started without you!"

My eyes went wide. I struggled to look up and back to Jane, who was still giving my ass a rhythmic ride.

She wasn't serious?! We couldn't do this while on speaker phone-

"We've got Larry, and Samantha from Sales on the line," Mark said, "And of course, Lisa and Kelly from upstairs-"

Mark trailed on, but I was barely listening. While he listed the members of our group call, Jane continued to ride my ass without remorse or pause.

I was forced to take it. Spread, bent double, and splayed out on the desk, she began riding me faster.

She was really going to do this, I thought.

She was going to fuck me in the ass during my remote-meeting.

"Uhh-" I fought to speak clearly, gritting my teeth in between words to brace for Jane's repeated pounding, "Hi -- hi everyone-"

"Everything okay, Cassandra?" someone's voice, a woman's piped up, "You sound like you're preoccupied."

"No!" I forced out, just as Jane bottomed out against my stretched ass hole, "Sorry -- um -- ah -- just trying to get comfortable in my chair."

I sounded like an idiot, and I knew it. But I guess my excuse passed, because somebody else started speaking immediately.

"So, let's get to it," A male voice -- a board member from upstairs -- began, "Who's got those fourth quarter numbers..."

Jane slapped against my ass, slamming me into the desk. I was mortified that someone might hear the sound, so I did the only thing I could think of -

I pushed back into Jane, countering her blows with my return thrusts so that she couldn't slam me against the desk top-

"Uuhmmmph-" I began to let out a moan, but stuffed my own hand into my mouth to stop myself.

The board members continued discussing idle business over the speakerphone, and I continued thrusting back against Jane, desperately trying to stop her from pounding me against the desk and making too much noise.

Oh God, my body was so alive-

I felt like cumming already. The meeting had just begun. I didn't know how I was going to-

"Cassandra?" A voice caught my attention, "Are you still there? I asked you a question!"

"Yes! Of course!" I blurted, ignoring the increasing pressure on my ass as I forced out coherent words, "I'm sorry -- can you -- uh, can you repeat the question!?"

Shit. Someone had asked me... something. But I hadn't even been listening.

An annoyed sigh was my response.

"I'd appreciate it if you paid attention," the snarky voice continued, I was asking you about-"

"Don't worry about it. I've got those numbers for you-" somebody else interjected, answering whatever question I'd evidently missed.

"Thanks," the board member answered, "At least somebody's on the ball today."

I grit my teeth, infuriated that I'd been made to look so incompetent.

"Uuunghh..." I grunted quietly, again biting down on my hand to prevent from making too much noise. Pleadingly, I looked back to Jane for mercy.

"Please!" I mouthed, "I'm begging you!"

Jane leaned forward, pressing the thick dildo into my ass as she pushed down next to my face with her own.

"Tell your Mistress you love her," Jane whispered, once more beginning to thrust against my ass.

I gasped. The pleasure was becoming overwhelming.

"I love my Mistress..." I whispered.

Jane smirked.

"What was that?" she answered back in a hushed tone, "I didn't hear you..."

"I love-" I began, but just as I started speaking, Jane reared up, and gripped the sides of my hips with her hands. In passionate, furious thrust, she bucked against me, thudding me against the desk and bottoming out in my ass-

"MY MISTRESS-" I finished, loud enough that the callers surely heard me.

"What was that Cassandra?" somebody asked over the phone, "I didn't quite catch-"

"I said-" I huffed, "Um -- I was just going to say...it's... MY BUSINESS... is to... um, ensure... a profitable quarter."

There was silence.

"Uh... huh..." A female board member's voice responded. "That's... a correct statement, I guess. Though I hope you got a little more out of all that ivy league education, Cassandra!"

There was laughter over the phone, and I blushed in humiliation.

"Sorry," I blurted out, trying to soften my stupidity with a casual, forced giggle, "I'm just... uh... a little distracted..."

Fuck! I was reaching the edge. I needed to cum -- badly. I couldn't believe that I was ready to orgasm just from Jane's ass-fucking... but I could feel myself gushing down my naked legs, trembling in anticipation-

"This is no time to be distracted," This time, it was Mark's voice on the phone, "In fact, Cassandra, I think we might want to go over some of your numbers before we continue. I worry you're starting to slip, and honestly, we really need to start seeing some better results."

I was horrified. So far, I'd sounded distracted at best, and like an absolute bimbo at worst. The meeting had been going awful for me already, but now, my coworker was taking advantage of my obvious disarray.

"I'd like to hear those numbers," A board member's voice popped up, and I cringed, "If there's room for improvement for one of our executives, I think we should all discuss it."

"Cassy, if you have no objections," Mark said, using my short-hand name to rub even more salt in the wound.

Of course I had objections. But I was also still looking back up towards Jane, who shook her head, giving me my answer.

"No..." I answered as nonchalantly as I could, "I've got... no objections..."

To my absolute dread, Mark began listing my business figures, discussing my recent quarter and financial reports.

While Jane rode my naked, slutty ass relentlessly, Mark began to tell various board members every about all of my so-called failings.

"If you factor it in per-dollar, considering your salary, you've had the lowest return-" Mark was droning on, but I was barely able to listen to him. He was full of shit, and if I'd been in a better state of mind, I might have been able to defend myself.

But right now...

Jane was burying the strap on so deep in my ass, with every thrust, I thought I might scream out in ecstasy.

"-room for improvement. If you need more assistance, or-"

I bit my lip, closing my eyes and squeezing the edges of the desk with my hand.

"-so young, maybe you need a little more experience before you tackle the larger-"

Jane's hands gripped my thighs again, and without warning, I felt her pull out of me.

"Uuugh-" I let out a guttural grunt, unprepared fro her sudden withdrawal.

"I mean, uh-huh," I added immediately, covering for my outburst, "That all sounds fair, Mark. You know best."

He knows best?! Why the hell had I said that!?

Because I wasn't thinking -- I couldn't think straight -- not with -

Jane's hands were on me again, this time, pulling me back, and lifting me up. She was spinning me around, rolling me on the desk so that I was laying on my back. My tits -- still naked and exposed, shot up perkily and eagerly for Jane to ogle as I splayed out once more for her.

"So Cassy, you think you can work on some of those issues, or do you need help?" the Board director was asking me this question now.

I honestly hadn't paid enough attention to what had all been said to know how to respond. My legs fell to the side, parting my ass and cunt for Jane to access.

My Mistress leered down at me, staring at my exposed intimate bits like a hungry hyena, and I flushed in arousal...

"Yes, sir," I simply said like an idiot, "I can work on those things..."

Jane pushed me back, pulling up my legs and tucking my skirt up under my ass.

She motioned for me to grab my legs from her, and I obliged, pulling my long limbs back to part and expose my pussy and ass as much as humanely possible.

"Good," the voice on the phone answered, "Because we've taken one hell of a chance on you, and if you're not up to the task-"

"I'm up to it, sir!" I answered, gasping as quietly as I could as Jane slid the thick dildo in between my parted ass cheeks again, lining it up with my felt-pen circled ass hole once more, "I promise, sir, I've just been distracted lately... but I can-UUGH!"

I let out a loud, obvious grunt as Jane thrust the tip of the dildo up inside my tight ass.

"What the hell was that?" someone asked.

"Sorry -" I blurted, "I just -- I stubbed my toe!"

Jane was slowly, mercilessly, sliding the strap on back into my ass.

I reached up, grabbing my tits with each hand, and gripping them as hard as I could in a feeble attempt to remain quiet.

"Sorry guys, I need to talk to Cassy one on one," the board director said. Even through my depraved, foggy mind, I could hear his annoyance and displeasure.

The others on the call quietly acknowledged his request, and before I knew it, they'd clicked off of the call.

Shit!

Jane was half way inside of me again, refusing to speed up from her glacial pace.

I felt like my body was going to explode. My poor ass was already straining to envelop the thick shaft, and Jane's mercilessly slow pace was driving me ever more wild.

"Cassy, I don't know what the hell is the matter with you right now, but it's very disappointing," The board member's voice piped up again, "I think you need some supervision. Something to get you back on the right track. Maybe someone with more experience-"

"YES SIR!" I blurted, barely able to contain my voice as Jane nearly bottomed out against my ass.

"Yes, you want some supervision?" The board member asked, confused at my reply.

"Yes!" I answered, "Whatever you think is best, sir!" I blurted out my response without thinking.

I was desperately trying to buck against Jane's hips now, feverishly trying to get her to fuck me. I didn't care about my phone call. I just wanted my ass to be pounded!

"OK.." he said, "Anybody particular you had in mind?"

I stared up at Jane. She smiled knowingly.

We both knew the name she wanted me to say.

I shook my head. I couldn't do this. I couldn't say what she was waiting for me to say.

Jane began to slide out of my ass-

"Jane!" I practically vomited her name, "Jane Scott! She can work with me-"

"Jane Scott?" The director's answer was once more confused, "Sorry, Cass -- I thought you despised her? You've filed so many reports..."

Jane glared down at me, and the thick dildo slipped out of my tortured ass another inch.

She was threatening to stop fucking me completely, I realized.

"I was wrong," I spat out unexpectedly, "Jane's a very competent worker. If anyone can right the ship, it's her. She's -- she's a genius, sir-"

I was babbling on, saying anything I could to both satisfy the board director and Jane at the same time.

I didn't have a plan. I was just saying the first things my sexed up, Bimbo mind could muster.

"Well... that's fine with me," a sigh from the other end of the phone, "I'm just surprised you'd want to give up any of your status to someone like her. Essentially, you're giving her one hell of a promotion... and taking a pretty big hit yourself -- I mean, she'd practically be supervising all of your projects... it won't look very good to the CEO... oh, whatever. I'll make some calls, and talk to Jane, see if she's willing to take on the task."

I winced. Something told me Jane would be happy to step up to her new job.

"Thank you sir," I said, and without a response, the director of the board hung up the phone.

"And thank YOU, Sassy Cassy!" Jane smiled and spoke up as soon as the call had ended, "After all that praise, I think I owe YOU something in return!"

I groaned. The tip of the strap on was still tucked up inside my quivering ass.

I'd humiliated myself in front of my coworkers, I knew. Asking for Jane's "help" with my job had not only been a major ego blow, but had also made me look completely incompetent.