Cassy's Awakening Ch. 05

"Uuuungggh----" I bit my lip, crumpling into the desk as Jane spanked me a third time in quick succession.

"Count 'em off," Jane said, "Let's say -- ten spankings for your misbehaviour. Does that sound fair?"

It did not!

SMACK!

"Count 'em!" Jane repeated, "Start with one! And keep that ass in the air, or it won't count!"

My knees were wobbly, and my tender ass was already on fire, but I desperately needed to please Jane.

I put all of my strength into pushing my ass back up into the air, gripping the edges of Jane's desk to brace myself for the inevitable-

SMACK!

"Uuunghhh-" I grunted again, gritting my teeth in a furious attempt not to scream out.

Fuck! It smarted so badly -- Jane was really putting everything she had into the harsh spankings!

"Oon-one!" I managed to get out the first count. It wasn't fair, really. This was the fourth spanking I'd received! I should have been able to at least-

SMACK!

Oh God!

"TWO!" I said through gritted teeth, burying my head down onto the desk. This time, Jane had made sure to smack the exposed skin next to my ass hole. The impact had been doubly torturous, stinging like hell, but also sending a twinge of arousal up my spine-

SMACK!

"Ahhh!" my mouth fell open as Jane's next spank landed directly next to my parted pussy.

"Ttthhrrr..threeee..." I groaned, feeling my body come alive.

God. Was I actually getting off on this depraved treatment?! With my naked, exposed ass in the air, I felt vulnerable... and naughty. Jane was smacking me just hard enough to punish me for my transgressions... but masterfully, with every stroke, she was managing to delight my intimate parts-

SMACK!

SMACK!

SMACK!

I counted each spank in succession, buckling at the knees with every blow, but thrusting my ass back up for more each time as quickly as I could-

"Tell me you're a stupid slut," Jane ordered me with an authoritative bark, "Tell me how sorry you are for displeasing your mistress!

SMACK!

"Seven-" I forced through grit teeth, and then added, "I'm a stupid slut!"

I bounced on my legs, trying to shake off the latest stinging blow. I could sense the tell-tale feel of a bead of moisture beginning to trickle down my parted pussy, and make its way down my naked leg.

"I'm so, sorry sorry for displeasing you, Mistress," I forced out, "I promise I'll be-"

SMACK!

SMACK!

"Nine!" my mouth dangled open, drool splattering onto Jane's desk as I writhed against her latest blow.

This one had been lighter -- smacking just sharply enough against my parted, wet pussy to send a wave of pleasure through my body.

Instinctively, I'd shoved my legs apart as far as they could, hearing a telltale rip from the poor panties which were stretched around my thighs.

"See, Cassy? This is why I told you no panties!" Jane laughed, tugging at the tattered remains of my underwear. She pulled them from my body with ease, and plopped them down in front of my face. They expensive silk panties were shredded ; utterly destroyed.

I braced for my last spanking, gritting my teeth and closing my eyes in anticipation.

Instead of a painful smack, though, I felt Jane place the cool metal measuring tool against the parted cheeks of my ass.

"Are you really sorry for earlier?" Jane asked, flicking the cornered tip of the ruler over my unguarded ass hole.

"Yes!" I gasped, both delighted and horrified at the teasing touch, "I'm sorry -- just please, Jane -- Ma'am -- let me get dressed! Someone could come in at any-"

SMACK!

Just as I'd let my guard down, Jane had swatted my ass a final time.

Once again, I saw stars -- feeling electric jolts bristling up my sensitive skin.

"Ten!" I grunted in pained relief. My ass was on fire. I was sure it would be bright red. Still, through the stinging pain... all I could think about was the throbbing desire coursing through me. Jane's brief but purposeful prodding at my ass and cunt had, combined with my thorough punishment, brought me nearly to the brink once more.

What the hell was wrong with me?! None of this should turn me on. I should be enraged-

"Oooh!" I let out an involuntary moan as I felt Jane's fingers on my ass. Against my throbbing skin, the coolness of her digits felt divine.

"You're not off the hook yet, Sassy Cassy," Jane's voice was soothing as she touched me. I felt her fingers slide down around my parted thighs, and up, across the quivering skin of my cunt, "You disappointing me this morning. We'll have to teach you better manners in the future."

As she spoke, her finger had made it up to my exposed ass hole, and lingered around my shivering skin.

Instinctively, I felt myself push up slightly against her, thrusting my ass up ever so gently against her waiting fingertip.

"Something on your mind, Slut?" Jane cooed, and I sighed in humiliation.

As I'd thrust up against her, she'd pulled back, leaving me mercilessly unfulfilled.

"You looking to get a finger up your ass, Cass?" Jane giggled, gently prodding my ass hole with her fingers, delighted at my automatic, aroused moan in response, "I mean, this is hardly the place. After all, anyone could walk in..."

Delicately, Jane traced a circle around my tortured ass, finally flicking the tip of her digit inside of me with a surprised thrust.

"Uuugh-" I grunted in delight, thrusting back against her again without thinking. My movement pushed her finger deeper inside of me, and she continued the fluid moment with a forceful shove.

"Who's ass is this?" Jane asked me, pushing hard against my ass and shoving her finger deeper inside of me.

I grunted in response, knowing what she wanted to hear but unable to get the words out.

Jane pushed harder against me, bottoming out her hand against my parted ass.

My mind was lost at the feeling of her finger inside of me. I pushed back, once, twice, continuing to thrust against her in a slow, rhythmic motion.

"Who's ass-" Jane began to repeat, but I cut her off with another grunt.

"Yours!" I answered through grit teeth, responding exactly as I knew she wanted me to, "It's your ass! It belongs to you!"

As a reward for my admission, Jane thrust her hand against me a couple of times in rapid succession.

"Oh... my god-" I panted, still feeling the sloppy strings of drool trailing out of my mouth onto Jane's desk as she finger fucked my ass. I gripped the edges of her desk with white knuckles, forcing myself to remain quiet and obedient.

Just as quickly as she'd started, however, Jane withdrew from my weary hole.

In my horny state, I actually mewled in protest as she abandoned my ass. I pushed my ass up into the air, almost pleading with her to continue, but all it elicited was a condescending laugh from my coworker.

"Eager for more, I see," Jane mocked me, watching as I blushed in humiliation. She picked up my shredded panties, and used them to wipe off her wet hand. Then she tossed them in the trash, with my bra.

"Almost time to get back to work," Jane said, looking at the clock.

My heart leaped. Through my humiliation and arousal, I was still well aware of my precarious state of dress. Topless, skirt hiked up -- exposed to the world should anyone open Jane's office door.

But as I began to stand up, Jane's hand pushed down on my back, keeping me in place.

"Not QUITE yet, Dummy!" she scolded me, "I'll tell you when it's time!"

I sighed pathetically, but lay back down against her desk again, keeping my naked ass up in the air as she circled around to the front of her desk again.

Once more, she fumbled through her desk drawer, putting her metal ruler back in place and pulling out a fat purple permanent marker.

"You ever written lines, Cassy?" Jane asked, and I stared up at her awkwardly and confused.

"Um... you mean like... as punishment... in school?" I asked. Jane nodded.

"Exactly," she said, "I think that's a fitting punishment for a ditz like you, don't you think?"

I blinked.

Was Jane really going to make me write lines?

It seemed a little... tame... at least by her standards. Humiliating and petty, of course, but I'd expected something more-

"Yes, I think it is more than fitting," Jane answered herself, and rolled the felt pen up against my face on the desk.

"You SAY your ass belongs to me, but I want to make sure you REMEMBER. Since you're too dumb to keep too many facts in your tiny, Bimbo head, you're going to write it down."

I let go of the desk, and picked up the marker with no slight trepidation.

There was more to this, I knew. Jane smiled, revealing as much.

"I think ten lines should suffice. One for every spanking you just received. It'll help you remember your place." Jane sat down in her desk chair, and pulled a small hand mirror out of her blazer pocket. She slid it up on the desk.

"What should we write..." she feigned a thinking pose before snapping her fingers, "How about -- 'My Ass Belongs to Jane'?

I was still confused.

"What is the mirror for?" I asked, nervously. Jane laughed.

"Well, you're writing the lines on your ASS," she said, "So if you think you can manage without the mirror, be my guest."

My eyes fell open.

"What?" I gasped, "I'm not writing that on my ass-"

I paused. Jane was staring down at me with an authoritative gaze.

Shit.

There was no getting out of this either, I realized.

If I wanted to put my clothing back on... I needed to get this task done, ASAP.

"If I do this..." I asked pitifully, "Will you let me put my clothes back on...?

There was no response from Jane. Just a smirk.

With a reluctant groan, I grabbed the small hand-mirror and held it out behind me.

I strained to look behind me while keeping my naked tits pressed against Jane's desk, but with a bit of effort, I was able to shift slightly enough to see the reflection of my sore ass in the mirror.

Oh God. I looked worse than I felt.

My ass was glowing red, all right -- but it was also glistening with sweat, and shimmering with the splattered remnants left over from my freshly spanked cunt.

I really must have enjoyed the spanking session, I had to admit, and Jane would have no doubt of that fact now. It had stung like a bitch, handily reminding me of my place beneath Jane, but it had undoubtedly left me horny as hell.

The perfect punishment, I realized with a pout.

"I- I don't know if I'm going to be able to write properly-" I began to protest, but a noise outside the door cut me off.

Somebody -- two or three people, by the sound of it -- were standing just outside Jane's office, having a conversation.

Shit! Immediately, the terror of my precarious situation flooded back into me.

I had to hurry.

I reached the felt pen back behind my ass, struggling to figure out the perspective of everything in the mirror.

"My Ass Belongs To Jane," Jane stated again, "Nice and bold letters, Cassy."

I sighed, and began to write.

...My... Ass...

The letters were clumsy. It was no surprise. Writing on my own ass, using a tiny, pocket mirror took no small effort... but every word I heard coming from outside Jane's office compelled me into action.

...Belongs...To...

I scrawled Jane's name last, sloppy as the rest, but just as bold.

The entire sentence had taken up the length of my right ass cheek. It started on my hip, but I'd written too big, and had been forced to end right next to my poor ass hole.

"One down..." Jane said softly, spinning to her computer and firing it up.

I glowed red in humiliation. As Jane's computer hummed to life, she began to click several keys on her keyboard, paying no attention to me.

Grunting again as I strained to watch my hands work behind my ass, I began writing the second line.

My...Ass...Belongs...To...Jane...

And again.

My...Ass..Belongs...To...Jane...

And again.

As Jane paid little mind to my efforts, I repeated the sordid writing again and again, filling my ass with the poorly written words until I began to run out of space.

"Ma'am..." I spoke up at last, "I'm... running out of room... I can't fit anymore- it's too difficult to write properly-"

"Write on your legs," Jane said, "Just try not to go too low, or that little skirt of yours might not cover it all up."

I blushed, but obliged.

Straining to reach farther down my backside, I scrawled the rest of my lines just under my naked ass, finishing my task with a tired, pitiful groan.

"I did it! I'm finished," I said, rather triumphantly at the silly but difficult task I'd struggled through

Placing the mirror and felt pen back onto the desk, I looked up at Jane pleadingly, "May I please get dressed again...? Ma'am...?"

Jane stopped working and turned back to me, as if I'd interrupted something important.

"Only if you've learned your lesson!" She said, smirking at me, "In which case, go for it, Slut! No undies... of course..."

I practically leaped off of the desk, pushing myself up and scrambling to pull my crumpled skirt back down over my now naked hips.

Next, I raced to put my shirt back on, buttoning it up half way before Jane stopped me.

"Half way only," she said, "Your tits deserve to remain on display. I don't want them covered up too much."

"Yes ma'am!" I said, uncaring that the top of my tits were spilling out of the shirt. My nipples were covered, and that was all that was important for the moment!

I swung into my blazer, buttoning it up half way as well.

I figured I knew what Jane wanted me to look like. With both of my buttons half undone, I looked slutty as hell in my office attire. Plus, I noticed immediately, when the loose fabric brushed against my pierced nipples, it was electrifying.

"Hike that skirt up a bit," Jane ordered me.

Hesitantly, I obliged her order... pulling my skirt a few inches up my legs.

Jane shook her head.

"It's too long," she said, "You can't even see all the hard work you spent writing your lines! We'll have to do something about that when we can. But for now, get your ditsy ass back to your office, and pretend to get some work done for a change."

I glared at Jane, humiliated at the implication that I wasn't a valued employee here.

"I'll be in touch," Jane said with a menacing look on her pretty face as I turned to leave her office, "Oh- wait-"

I turned back just in time to intercept the felt pen she'd tossed my way. Clumsily, I caught it before it smacked me in the face.

"Make sure you take your pen!" Jane smiled, "You might need it again later!"

I was still glaring at her, but went to put the marker into my blazer pocket.

"Nuh-uh-" Jane said as I slid the felt pen into my pocket, "That's not where it goes, Cassy."

I stared at her blankly.

"What... where do you want me to put it...?" I asked dumbly as Jane turned her head from me again, back to her work station.

"Mouth, ass or cunt," Jane said idly, typing away nonchalantly, "Those are the holes you use for holding things, after all. Actually -- not your cunt. It's a little wet down there. Too slippery, and you might enjoy that too much."

My mouth dropped open.

"You... you can't be serious?" I asked, "I can't... I can't walk around with a pen in my -"

Mouth? No, of course not. There was no way I could hide that around the office.

That left one hole.

"Please, Jane," I said, correcting myself immediately, "I mean Ma'am, of Mistress - Haven't I suffered enough...?"

Jane didn't even look up from her desk in response. She just kept typing, as if I wasn't even here.

"Ma'am, please-" I begged, stopping as Jane reached out to her intercom.

"Stacy, could you pop in here for a moment?" Jane said, and I flinched.

"Yes ma'am, right away!" Stacy responded.

"Get to it!" Jane said to me after the intercom clicked off, "Or you can ask Stacy for help when she gets here."

Shit!

I opened my mouth to protest again, but gave up.

Instead, I reached around quickly behind my skirt, and flipped it up.

I couldn't believe what I was doing.

Spreading my legs slightly, I flipped the pen around so that its blunt bottom end pointed up in between thighs.

Knowing Stacy was on her way to Jane's office, I didn't have time for pause. I bent forward slightly, assuming a natural parted position, and pushed the pen up into my ass.

"Thank me while you do it," Jane said, "You're lucky I didn't give you the whole box of markers."

I grunted briefly as the blunt, thick felt pen pushed into my ass, but I didn't stop or hesitate. I thrust the entire thing up as far as it would fit, until only the lid was poking out of me.

"Th- thank you, ma'am-" I groaned, feeling the thick shaft snugly inside of me.

I was just in time.

My skirt had barely fallen back down around my ass again when the door swung open, and Stacy entered.

"Ma'am?" Stacy's voice piped up as she entered the room. She looked surprised to see me still in Jane's office, and even more to see me looking so improperly dressed and flushed with pink cheeks.

"Oh -- Ms. Riley, I didn't know you were still here-"

"She's just leaving," Jane said dismissively, as if I was just on my way out the door, "Aren't you, Cassandra? Oh, and don't forget your folder."

Shit! In the chaos of everything that had happened, I almost forgot about the dreadful manila folder Jane had procured. It was still stuffed full of my sordid, nefarious secrets.

I grabbed it from Jane's desk, ignoring the feel of the thick felt pen wriggling in my ass as I moved.

"Thanks for your time..." I said to Jane, though why, I couldn't say. I sounded submissive and weak in front of Stacy.

But it didn't matter, I told myself. I could feel the felt pen in my ass, clenched in my tight hole. I needed to get out of here, into the privacy of my own office.

"Keep in touch," Jane said as I exited her office, "I may have more notes for you later."

I winced at the condescending tone in her voice, but continued down the hallway without pause, leaving the two women in Jane's office.

With every step I took, I could feel the marker wriggle in my ass. I clenched my legs together, trying to stop it from mercilessly teasing me as I moved, but it was awkward and difficult.

On top of this, my shirt was brushing incessantly against my poor tits. My nipples were throbbing, aroused and eager for attention.

"Ms. Riley! Looking sharp today!" An intern passed me, taking a long, ogling look at my obscene cleavage.

Shit.

I didn't respond to him. I had to get to my office. The movement in my ass and against my tits was driving me wild... and I knew I wouldn't be able to keep my composure for long...

"Cassandra!" Another voice surprised me just before I'd made it to my office. This time, it wasn't an intern, but Mark, one of my other coworkers.

Awkwardly, I spun around to face him. In my haste, I felt the marker slide an inch or so out of my ass.

Shit. Shit-shit-shit-

"Oh wow, love the outfit today," Mark said, not hiding his wandering eyes at all.

I feigned a smile, trying desperately to act as if all was normal.

"Th-thanks, Mark," I said, sounding as foolish as I felt. Mark's eyes were squarely on my tits.

Of course the chauvinistic prick would appreciate my outfit today. My tits were practically on display!

Without glancing down, I could only pray that my nipples were at least still covered.

I fidgeted a bit with my blazer as Mark awkwardly ogled me.

The pen in my ass slipped out another half inch.

"Uuhhi've got to get to work-" I blurted out, squeezing my legs together to catch the pen before it slid the rest of the way out, "See you around the office, Mark!"

I sounded like a ditz, I knew. I gave Mark a wide, innocent smile as I hastily spun around to my office, and threw myself inside.

As soon as I closed the door behind me, my hands shot down under my skirt.

"Fuck!" I grunted, reaching up behind my ass to push the infernal pen back up inside of me, and clenching my ass to keep it in place..