Cassy's Awakening Ch. 05

The impromptu ass fucking had really gotten to me, I realized. My short walk over to my office had caused me to begin to sweat. Hopefully it hadn't been too noticeable.

I shuddered at the thought of somebody catching me in such a lewd act. What would have happened had the felt pen slid out of me in the hallway -- revealing my depraved secret?!

"That fucking bitch..." I muttered, cursing Jane as I clumsily made my way to my desk.

My next task was sitting down -- no small feat with such a thick pen poking out of my poor hole.

In the end, I had no choice but to just go for it. I sat down as gently as I could, feeling the pen thrust up into me as I put my weight onto the chair.

I let out an involuntary groan.

Fuck!

I hated to admit it, but it felt... good. Against my better judgment, I rocked my hips gently, letting the pen wriggle up into me with every jolt.

This was ridiculous! I was practically giving myself an ass-fuck in the office, using the same permanent marker I'd just used to write "MY ASS BELONGS TO JANE" all over my poor, heavily spanked ass!

I forced myself to stop gyrating my hips. I had to get a grip!

I powered up my computer, eager to sink into some real work. I needed to get my mind off of everything! I couldn't survive if I didn't find a way to distract myself-

PING!

As soon as my computer had fired up, a notification popped onto the screen.

It was from Jane, I could see immediately. She'd sent me a message over our office's internal communication system.

Nervously, I opened the digital chat system up, and her message shone across my screen.

"Having fun, Slut?" Was all that it said.

Furiously, I began typing a return message.

"NO!" I wrote in all capital letters, "I AM NOT."

There was a pause... but then a reply came back.

"Too bad. Next time, listen to your orders better, and I might go easier on you. How is your ass feeling? Did you learn your lesson?"

I glared at the screen, but didn't respond.

Another message shot up anyways.

"Failure to respond to your Mistress is cause for punishment."

I glowed in rage.

"YES. I LEARNED MY LESSON. NOW LEAVE ME ALONE!" I wrote, but before sending it, I deleted the whole thing. It felt like defeat not to send snarky message... but that was what I was, wasn't it?

Defeated?

"Yes ma'am," I retyped my message, much more politely this time, "I've learned my lesson."

It pained me to hit 'send', but I did it. When no message from Jane returned to me, I closed the chat window, and opened up my work files.

Hopefully she was done with me for now, I mused. I needed the break. Already, I could barely focus.

My mind was squarely on my poor ass. I could feel the felt pen inside of me... and it was all I could to resist the urge to grind against my plush office chair.

I felt like a slut. My nipples were hard, pointing out against the loosely fit fabric of my top.

God -- my body was on fire!

Part of me wished Jane would burst through my door again, and repeat our earlier session.

Humiliating as it had been... my body had obviously enjoyed the treatment, and was betraying me now, craving more.

I leaned back in my chair, trying to regain my composure. It proved to be a mistake. Leaning back only caused the felt pen to slide up out of my ass again, and I was forced to lurch forward again, jutting it back into me with at thud-

"Dammiiiit...." I whined out loud to myself, slumping forward against my desk and trying to force the depraved thoughts from my mind.

I began to get to work -- or what counted for work in the moment. Clicking through my computer files, I did my best to focus on anything but my quivering ass.

I wasn't very successful, but I had little choice. I HAD to get some work done!

Over the next hour, I was only mildly successful. Aside from my constant mental interruption, there were the regular occurrences as well. Several times, co workers would pop their heads into my office for a chat, or to drop off a report for me to go over.

Every time, I'd wince in terror as their eyes fell over me.

Could they tell the state that I was in? Had they caught me gyrating my hips? Had I been biting my lips, stifling a lusty groan? Had I been perspiring, or blushing, or were my tits hanging too far out of my top-

Oh God!

I was in hell!

Finally, an hour and a half into the day, I couldn't take it any more.

I re-opened the chat box on my computer, and brought up Jane's name.

"Ma'am!" I typed hastily, messaging Jane again with the messaging system, "I can't work like this!"

Sent.

I watched the message box for a response. It took a few agonizing minutes for Jane to respond.

"Take out your tits." was all the message said. I balked.

"Please," I replied, "I can't take any more of this! I'm not getting anything done!"

Again, I waited a minute for a response.

"Take out your tits," the message repeated, "I'm giving you two minutes to play with yourself. Consider it a favour, Slut. You can let off some steam."

My mouth was hanging open.

That... fucking... bitch!

I fumed, but as I glared at the monitor, my thoughts began to wander...

I DID need to let off some steam. My body was practically vibrating at the thought.

Maybe it WOULD help me concentrate... and besides... I didn't REALLY have a choice, did I?

The more I considered the absurd notion, the hornier I became. My nipples were practically pleading to be released from their torturous confinement, and my poor, sexy ass was just begging for attention...

Biting my lip, I reached up and flipped the loose fabric of my top down over my breasts.

I knew I shouldn't do this. I knew that by doing this, I was allowing Jane to beat me yet again.

But I couldn't help it...

Immediately, as I felt the cool air of my office hit the sensitive skin of my pierced nipples, I knew I'd made a mistake.

There was no stopping now.

Two minutes, I thought to myself. That's what Jane had said. I could do whatever I wanted for two minutes!

I slid my hands over my sensitive breasts, fidgeting playfully with my piercings and gasping at the electrifying sensation.

"Yesss..." I moaned... twisting the metal piercings gently and feeling my body explode with pleasure.

Two minutes. I had two minutes. I knew exactly how I would spend them.

My left hand stayed on my tits, pinching and playing with my nipples, but my right hand shot down between my legs, and yanked up my skirt.

I leaned back, feeling the felt pen begin to slide out of my ass again, but this time, I caught it in between my fingers.

"Uuugh-" I groaned in delight as I thrust the thick marker back up my ass. I pushed it hard, and then withdrew it again, only to thrust it inside of me in once more.

"NO CUMMING!" A message popped up on my screen, and I caught it out of the corner of my eye as I began to rhythmically fuck my ass with the marker.

"Fuck!" I cursed, already feeling myself begin to reach the edge of an orgasm. I was mashing my tits with one hand, and fucking my ass with the other, completely lost in the moment.

I wanted to cum!

I increased the pressure against my ass, speeding up my hand and giving myself a thorough, deep fuck with the marker.

I could feel beads of moisture trailing down from my cunt, over my hand and the felt pen.

Fuck Jane and her idiotic order, I thought! I needed to cum, and I was going to -

I gave myself a powerful thrust, rocking against the pen as I shoved it deep inside of me.

No! I couldn't!

I bit my lip with enough force that I winced in pain.

I couldn't cum! I couldn't break her infuriating rules!

"Fuck!" I cried out again, desperate to send myself over the edge, but unable to muster the rebellion.

I cooled off for a moment, and then got back to work, twisting and pinching and fucking myself

"Uuugh-" I was on the edge again, biting my lip to stop myself from cumming.

I looked at my monitor. The last message, "No cumming!" hung on the screen. I prayed Jane would send a new one, allowing me to go all the way.

I started fucking myself again, praying for a miracle.

Nearing the edge, I saw the indicator that Jane was typing spring to life.

Yes!

This could be it!

I began thrusting the felt pen in and out of my ass as furiously as I could manage.

She was going to let me cum! I just knew it! My Mistress was going to take pity on me and -

"Two minutes is up!" the message said.

My body felt like it had just been dunked into ice water.

"No!" I responded verbally, continuing to fuck my eager ass with the felt pen.

No! I couldn't stop now! She couldn't do this to me!

"If you don't stop now," a follow up message appeared on the screen, "You'll be in for another spanking session."

Immediately, my hand released the pen in my ass.

I let go of my tit, too, feeling stupid and frustrated as I obeyed Jane's digital demand.

Was I THIS whipped?! She couldn't even SEE me, yet I was leaping at her demands like a trained dog!

"I stopped!" I typed hastily, unsure of why I was admitting to have done anything at all. Again, Jane had no idea what I was up to in my office. I could have just lied...

"Good Girl," Came Jane's response, "Now, cover those tits up. Hurry."

I stared at the message, confused for a moment. Almost immediately, before I could even follow through with the request, my office door began to open.

Shit!

I hurriedly reached up, and pulled my open top up around my naked nipples just as Stacy poked her head into my office.

"Stacy!" I blurted, barely managing to cover myself as the blonde receptionist entered the room, "What -- what the hell are you doing?!"

Stacy looked aghast.

"Are you an imbecile!?" I angrily shouted at her, too unnerved by the close call to keep my temper in check, "How many times have I told you to KNOCK before entering!"

My face was red, and full of rage, and Stacy looked like she'd just seen a ghost-

"I -- I just wanted to remind you about your remote-meeting coming up soon..." Stacy's face wavered. The poor girl looked like she might cry. "You asked me to remind you, and-"

Shit. Stacy was right.

I had a remote meeting coming up in a half hour, and one of Stacy's jobs was to remind me in advance of such things.

"Stacy, stop!," I barked, not caring if she was right or wrong in this moment. She'd nearly caught me fondling myself, and the thought was humiliating. I needed somebody to take out my frustration on, so the poor girl would have to suck it up and take it!

"I've had it up to hear with your incompetent, sorry excuses-"

Before I could finish my angry tirade, a message flashed up on my monitor.

"THAT WAS MEAN." Jane's message said. I shuddered.

What the hell!?

How did Jane know what was -

"APOLOGIZE TO STACY."

The message had appeared so suddenly, it had startled me. I didn't even have time to fully consider it before a follow-up message appeared below the first.

"APOLOGIZE NOW. OR PUNISHMENT."

"I'm sorry, Stacy!" I blurted out hastily, unable to process what was happening.

Stacy looked taken aback. I cursed myself for being so obvious with my sudden change of tone and demeanour, but I'd been unprepared for Jane's unexpected instruction.

The messages on my screen weren't visible to the receptionist, thankfully.

"TELL HER YOU'RE SORRY FOR BEING SUCH A BITCH." another message flashed up, "AND DO IT WITH A SMILE -- I'M TIRED OF STARING AT THAT FRUMPY FROWN."

It hit me at last.

My webcam.

Jane must be watching me through my monitor webcam!

I felt stupid for not realizing it earlier, but it felt so obvious now! Jane had already revealed her ability to access the backdoor network of our office's systems. It would be no struggle to tap into my webcam. Hell, I could do the same to her -- at least, before she'd taken control of my own access routes.

"I'm -- I'm sorry for... for being such a bitch to you, sometimes...-" I blurted out again, watching Stacy's face morph from horror into utter confusion as I forced my best smile.

"Um... it's fine, Ms. Riley," She answered me, absolutely confused, "I mean, you're -- you're not a bitch!"

There was little conviction in her voice.

"DO YOU WANT TO FUCK HER?" Jane's message caused my eyes to widen. There was no instruction in the message ; just the lewd, bold question.

"Stacy, why don't we talk later, okay?" I said quickly, desperate to get the receptionist out of my office before Jane pushed things too far. The perverted inquiry had made me even more nervous. I still had vivid memories of how quickly she'd turned my simple gardener into a second Mistress...

"I... ummm..." Stacy fumbled her words, clearly uncomfortable and unsure of what was going on, "Yes, ma'am. If you need me, I'll be at my desk..."

The timid receptionist looked all too eager to leave my office.

I feigned my best, warmest smile, and nodded as the receptionist closed the door behind her after making a quick departure.

As soon as the door clicked shut, I breathed a huge sigh of relief.

"WHAT THE FUCK WAS THAT?!" I practically smashed the words into my keyboard the moment I was alone again.

"Oh, calm down," Jane's reply came quickly, "You know you've wanted to fuck that little tart from the moment she started working here. Stop acting like you've got a stick up your ass."

I winced, remembering the thick felt pen that was still rammed up my ass.

In the horror of the moment, I'd almost forgotten it was there. Immediately, the arousal flooded back into me.

"Don't lie!" Jane's messages continued, "You'd love to stick your tongue up in between Stacy's tight, sexy ass."

I blushed.

"That's completely inappropriate!" I typed back, trying my best to ignore the visual image Jane had planted in my head. "And if you keep making me say and do strange things in front of people, they're going to realize something is going on!"

"Just imagine her legs wrapped around your slutty face..." Jane continued, ignoring my remark, "Looking up at her perky little tits as she cums against your lips..."

I squirmed in my chair, feeling beads of sweat forming on my body.

Fuck. The thought of Stacy's firm, supple body wrapped around my own sent shivers down my spine.

The twenty-something college girl was undeniably sexy, and as much as I hated to admit it, I'd taken my fair share of glances at her tiny, pert ass...

I caught myself reaching down in between my legs again. Instinctively, my hand had been moving towards the felt pen -- but I'd stopped myself, remembering Jane was watching me over the web cam.

"I'm not like that! I'm not a WHORE!" I typed, punching 'send' with enough force to nearly break my keyboard.

For a moment, the screen was blank.

Then, another message.

"Let's put that to the test," Jane's message felt ominous, and the follow up confirmed my fear.

"Pull that felt pen out of your ass."

I winced. Shit.

I hated when she took control like this during one of our arguments. It was such an obvious power play, reminding me who was in charge.

In the back of my mind, I wondered why I even bothered to resist her. Every time I lost my cool, it ended the same way.

With my total and complete humiliation.

I sighed, knowing I was about to pay for my little outburst.

I chided myself.

It's your own damn fault, Cassy!

Knowing Jane was watching through the camera, I moved to obey her instruction. With no small level of shame and reluctance, I reached down to pluck the thick felt pen out of my tight hole.

Knowing Jane could see me obediently perform the lewd action sent a shiver down my spine, and when the pen finally slid out of me with a slick 'plop' I glowed red with embarrassment

I hadn't realized just how wet I was. The pen -- my ass -- my skirt beneath me, was almost entirely soaked.

I peeked down in between my legs to an awful sight. The permanent marker on my ass cheeks was running -- seeping down into my skirt, staining the fabric. It was dripping down my legs. I wouldn't be able to walk through the office without people noticing.

I groaned as I held the pen up to the monitor webcam.

"Pop those tits out again," another message appeared.

Again, I didn't resist Jane's order. I pulled my loose top down again, spilling out my tits for the camera.

"Write I AM A WHORE." another message came in, "Write it. Bold letters -- across your tits."

I murmured a pitiful protest, unsure if Jane could hear me over the camera, but assuming she could.

"Wait... please..." I begged, "I'm sorry. I'll just say it! I'm a whore! We both know it. I don't need to write it-"

"TWO SECONDS OR I'M COMING IN THERE!" Jane's message appeared immediately.

My hands sprung into action. I fumbled with the felt-pen cap. It was still slick with my wetness, and took no small effort to remove... but I was able to shimmy it off, and get to work.

'I AM'... I began to write, pouting with every stroke of the pen, 'A'...

The first three words filled the space on my right breast. Again, I was writing upside down -- and the felt pen was slippery in my fingertip

Trembling in humiliation, I scrawled the final word -- 'WHORE' -- large, and bold, across my opposite breast.

"That was fast! Good girl!" Jane's message flashed, "Now tell me : WHAT ARE YOU?"

I stared down at my tits. Submissively, I held them together, and pushed them up at the screen, providing her with her answer.

I'd earned this, I reminded myself. I'd practically asked for the admonition with my insolence.

"I'm a whore," I whispered quietly, displaying my work for the camera.

"Does the WHORE want to please her mistress?" Jane's message was again immediate.

I nodded pitifully. Jane had won, I knew. There was no point in fighting this any longer.

"PROVE IT." Jane responded, "I'll be in your office in a few minutes. I'm going to play with one your holes. Pick one. Your ass, or your cunt -- whichever one you want to be fucked the most. Circle it with your pen, and have yourself presented and waiting for me when I arrive. You know the positions. Leave your door unlocked."

I blinked at the monitor. With my lewdly marked tits still dangling out in the open, I typed a response.

"I have a remote-meeting in a few minutes!" I reminded Jane, "And what if someone comes in and sees me???"

For a moment, there was no response. Then, a simple answer :

"Don't disappoint me. Last chance."

Fuck!

"Mistress-" I began to type, in full begging mode now, "Please, may I ask for your mercy, ma'am?"

There was no response.

"I can't just get naked in my office!!" I typed hastily, but again, the message screen refused to answer.

To my horror, Jane's name had greyed out, indicating she'd actually logged off of the system.

I considered my options. I couldn't go through with this! I DID have a meeting, only a few minutes from now! It was a remote meeting, of course -- speakerphones. But still, there was simply no time for Jane's harassment! Now now! Not HERE!

I picked up my office phone, and pressed the button to dial Jane's office. The call went straight to voicemail.

God dammit! I slammed down the phone.

What was I going to do?!

In the back of my mind, I knew I had little choice. I had to obey Jane. No matter how absurd or impossible the situation at hand was, I had no real option but to trust her to...

To what?

Protect her little Office Whore?

I groaned, standing up from my office chair and leaning on my desk. I re-read Jane's last messages a few times, making sure I hadn't missed anything.

"Pick a hole" she'd said. I winced at the lewd language... but couldn't help but feel a familiar rush of desire swell up inside of me.

Again, I felt my ass begin to quiver in anticipation. I'd had that damnable felt pen packed tightly up inside me for hours now... and with no relief, I was still squirming for attention.