Cassy's Awaening

Synopsis : Jane's grip tightens around Cassy, and the business executive begins to learn the intricacies of her new role. With the weekend coming to a close, and an impending return to the Office on the horizon, Jane takes Cassy out to make sure she won't soon forget who is in charge.

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 4 : Trip to the Mall

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The first thing I felt when I opened my eyes was a hot, beguiling feeling between my thighs.

Before I even sat up in my plush bed, my hands snaked down under the covers, sliding up in between my legs.

"Fuck..." I muttered, feeling the wetness that clung to my skin. My body was still aroused from last night. It had taken me forever to fall asleep. I'd laid awake, battling the temptation that I'd built up over the long, torturous evening.

Last night, after Isabelle had left us, I'd waited patiently in the living room of my mini-mansion for Jane to return to me. I'd been so nervous... anticipating any number of great horrors to emerge from her foreboding duffle bag. With all that had already happened to me ; my impromptu poolside training session, my oral fuck-session with Isabella, the humiliating experience of being shaved in my own back yard, I didn't know what else Jane could throw at me. But I'd learned to expect the worst.

Which is why I'd been surprised when Jane had simply wanted to watch a movie.

I'd been prepared for another round of exasperating torment. I'd been sexed up, turned on, and left in a sloppy state by my ordeal earlier.

I'm ashamed to admit it, but I'd been halfheartedly looking forward to Jane finishing me off with the tricks and toys she'd brought with her. After all, neither of the two tantalizing women had allowed me to cum, despite repeatedly bringing me to the edge over and over again...

But Jane had simply kicked her feet up, and ordered me to play something on my giant flat screen TV. I'd flipped through the pay-per-view menu for her until she'd found something she'd wanted to watch. It hadn't been anything crazy, even. Some old monster movie from the 50s. It was black and white, and corny as hell...

Not that I'd watched much of it. Even though Jane seemed content to relax for the rest of the evening, I learned I'd have no such luck. She ordered me up onto the couch, and I'd obeyed. I'd stretched over her, lying on my back over her lap.

Then I'd parted my legs, and felt her hand slip down onto my cunt.

Though I'd been initially confused over her actions, her torturous plan had revealed itself to me quickly enough.

While she watched the cheesy monster flick, she'd fondled me on her lap. I'd stared up at her, my back arched across her legs, as she'd teased my pussy and pinched at my nipples.

Her eyes had been on my wide-screen TV, but her hands had never left my body. They'd spent an hour and a half tickling my delicate spots and edging me into a state of utter lust.

She'd treated me as if I was simply something to fidget with while she watched the movie. She'd toyed with me like a play thing! She'd hush me when I got too loud, but always maintaining my constant state of arousal with an endless fondle that lasted long after the credits had rolled.

All the while, I hadn't been allowed to cum!

It was a greater torture than anything I'd endured so far, and when she'd finally pushed me off of her lap, and declared that she was leaving for the night, my mind nearly broke in half.

That was it? That was her master plan? To rile me up, and then leave me be?!

It turned out to be a master stroke. Jane had left her duffle bag in my living room, but ordered me not to investigate it. Then she'd given me what turned out to be an absolute body-slam of an order :

I was not to touch myself without her explicit permission, no matter how aroused I felt.

I squirmed in my bed, remembering the ordeal I'd gone through yesterday.

After Jane had left, I'd spent the the remainder of the evening in a tizzy.

She'd left me precariously close to the edge ; desperate for an orgasm that had been denied to me for hours... and it drove me nearly mad.

Though I should have rejoiced at finally being left alone in MY house, I found myself pitifully wishing she'd return, and finish me off.

"Fuck!" I swore again, getting up from the bed, and throwing on a white, silky robe over my naked body.

I cursed at the feel of the fabric against my body. Even the touch of the robe on my naked ass and tits felt like a gentle caress, sending sensations of desire flooding up my spine.

I was a mess. I looked at myself in the mirror, and the reflection staring back at me confirmed as much. My cheeks were flushed, my breathing was heavy. I needed to cum.

Fuck Jane, I thought darkly. She didn't own me.

She might be able to order me around when she was here -- but she couldn't control my every waking moment! She'd left me alone, and I damn well could do what I please!

This was still my house, I told myself. I was still Cassandra Riley. I forced myself to remember that I wasn't just some sexed up fuck-pet, no matter what Jane had decided.

I had agency! I had free will!

If I wanted to fuck myself in my own damn house, so be it!

I should have done it last night! Immediately after she'd left me, I should have plunged my fingers up into my cunt and fucked myself senseless!

Feeling defiantly naughty, I spun back to my bed. My thighs were burning, so I laid down onto my back over the sheets, and spread my legs.

"Aaannhhh..." I let out a pent up moan as my hands slipped under the robe, and into the shivering folds of my soaked cunt.

My mind felt conflicted, but my body exploded at the touch.

On one hand, Jane had been explicit : NO TOUCHING YOURSELF.

On the other hand -- fuck that lecherous whore! How would she possibly find out about my rules violation?! She wasn't omnipotent -- far from it!

Yesterday, she'd debased me in a way I'd never thought possible. She'd humiliated me in front of my gardener, and trained me like a dog!

It felt good to rebel against her! I almost wished she was here, to see me fucking myself in spite of her stupid orders.

I slid a finger inside of my cunt, gasping at the feel.

Oh God, yes! I was so desperate for this-

"Breaking the rules, aren't you?" The sound of a voice coming from the door of my bedroom caused me to practically jump off of my bed in terror.

I leaped up, yanking my hand out from in between my legs, turning to the source of the voice.

"I thought you weren't supposed to touch yourself?" It was Isabella. She was standing in the doorway of my master bedroom, wearing a casual pair of blue jean shorts and a white tank top. Her hair was done up today, pulled back above her ears, giving her a sexy, fun look -

"What are you doing in my house?!" I exclaimed, surprised to see her. I fumbled with my robe, trying to cinch the belt so that I was covered, "Did you break in?!"

Isabella laughed.

"Oh, for fuck's sake," even as she cursed, her South American accent sounded sexy, "Is that immediately where your mind goes? Poor, Colombian gardener... she must break into people's houses, and rob them!"

"That's not what I-" I began, blushing at the implication she was making, "I meant, how did you even get in-"

"Jane left the key outside for me, dummy!" Isabella laughed again, and I fumed, "She told me to come over nice and early, and get you ready for the day."

"She took my keys?!" I exclaimed, more concerned about Jane's bold decision to hand my key out to my gardener than I was about the fact that Isabella was here in the first place, "She can't do that!"

Isabella shook her head, and shrugged.

"Seems to me, Puta, she can do whatever she wants around here," she said, "You're pretty much her Bitch, far as I can see. And speaking of that-"

Isabella pulled her phone out of her pocket, and began to type at the screen.

"She's not going to be very pleased to know what you've been up to this morning," she said, nodding at the ruffled sheets on my bed, "She told me to make sure you were behaving. Guess you weren't-"

"Wait!" I said, bounding across the room and reaching out for Isabella. I put my hands over hers, stopping her from texting Jane for the moment. "Wait, Isabella -- you can't message her that! Please! She'll -- you don't understand -- she's got blackmail-"

Isabella laughed again.

"I don't care what she's got," she said, "I'm just here to enjoy the ride, Hussy."

She turned her phone screen off, and I breathed a sigh of relief.

"OK, I won't tell her what you tried to get up to," she said, "But you only get one strike and you're out! I doubt you'd have had the same mercy with me when I was in your employ."

I blushed, knowing she was right. I'd have never given Isabella a free-pass like the one she'd just given me..

"Thank you!" I breathed, truly meaning it, "I swear -- I won't give you any more trouble. Whatever you need to do... whatever Jane told you to do- just please, trust me when I say it's incredibly important that I manage to keep her happy-"

"Oh, right!" Isabella quipped, "Speaking of all that, we're already running late! We've gotta get you shaved, showered and dressed. Take off that robe, and let's get going!"

I blushed again at Isabella's words.

"I- but-" I began, not sure of what I was trying to say. Somehow, I'd thought Isabella might go easy on me. But evidently, she was still planning on carrying out Jane's sordid instructions...

"Of course," I accepted with a tone of dejection.

I opened my robe, and let it fall to the ground.

Immediately, my skin flushed with goosebumps. Isabella ogled me my tingling body, making me feel even more naked than I was. My bare nipples began to harden as she watched me, and my ragged breathing betrayed any notion that I wasn't still heavily aroused from last night.

"Good," she said, taking a step around me to give my ass an appreciative smile, "Now, let's get started."

Nodding, I turned, to head into the washroom that connected to my master bedroom.

"What are you doing?" Isabella asked. I turned around, confused.

"That's not where you get ready," she said, motioning me to get out of my bedroom, "Jane gave me an explicit set of instructions. She says you haven't earned your indoor privileges... so that means-"

I groaned. I knew exactly what that meant.

Stark naked, I let Isabella lead me downstairs. I didn't like where this was headed, but it felt dangerous to protest. I'd already gotten one free pass, and I didn't want to press my luck.

Still, I couldn't believe it : 'Indoor Privileges?!' What the perverse hell did that mean?! Who did Jane think she was, imposing such a childish set of laws for me to follow?!

But I'd swore I'd behave, and I still felt perversely grateful to Isabelle for hiding the fact that I'd tried to violate my 'no-touching' rule.

For some ridiculous reason, I felt compelled to obey her now, if only to prove that I was truly thankful.

"Get down, into position!" Isabella commanded, pointing to a spot on the grass and opening up the bag she'd been carrying.

I whimpered, knowing there was no point in resisting. Exiting my house, I tip toed nervously into my yard, peeking around to make sure nobody was peering over my tall privacy fence.

This was really happening again, I thought, as I laid down on the grass. I knew what Isabella was about to do. She was already shaking a can of shaving cream, watching me part my legs on the lawn to expose my naked pussy to her.

"Damn, Rich-Bitch," Isabella quipped as I felt the shaving cream splatter against my quivering clitoris, "You're practically squirting all over the place already. Jane really got you riled up for the long haul, huh?"

I groaned, feeling the olive skinned beauty's fingers begin to work the cream around my cunt once more. Like yesterday, the Colombian goddess worked me into a frenzy, gently massaging my tender pussy before she got to work with the shaver.

"I'll take that as a yes," Isabella giggled as I moaned in my yard. She ran the razor down my ass, as she had last night, spreading my ass cheeks to gain access to every last inch of me.

"She-" I breathed heavily, "She kept me on edge all night. It was torture! I'm still so horny... I can barely think straight!"

I wasn't sure why I'd offered up that information. It was humiliating to admit, especially to my former gardener, but it had spilled out of my lips unprompted, as if I'd wanted to say it.

"Well, could have fooled me!" Isabella said sarcastically as she hurriedly finished her job between my legs. Once again, I felt her wipe away the residual shaving cream... and once again, she leaned in, and planted a tantalizing kiss squarely on my clit.

"Aaah!" I cried out, bucking against her lips. She pulled back just as quick as she'd leaned in, leaving me writhing on the ground.

Isabella had finished much quicker this morning than she had last evening. It was disappointing... honestly. I burned with shame, but I found myself wishing she would continue tending to me.

"Oh God, Isabella," I panted, "I can't take it anymore. You have no idea how -- how close I am - I feel like my body is going to explode!"

"You're nice and smooth," she said, ignoring my desperate, sordid words, "Almost ready for Jane. Let's get you cleaned up now -- you look like you've just spent the night in a whore house!"

I groaned, knowing what was coming next.

The hose.

I looked around, desperate to re-confirm no one could see us. My expansive yard continued to hide my naked body, and I thanked the Gods I'd had the foresight to get a six foot privacy fence installed when I'd moved in.

The hose water felt especially cold today on my hot, aching body.

Isabella ordered me to stand, and I'd raised my arms above my head as she blasted me with the icy stream.

I couldn't believe this was happening. I was bathing in my back yard -- again! Isabella blasted me from the front, and back. I spun around, letting her get every angle... and when she was done with the basics, she ordered me to spread my legs open and let her power wash my cunt and ass.

I squealed as the icy water blasted my sensitive bits. I held my ass apart, doing my best to follow her instruction and help her get me as clean as possible. She came close with the hose, practically jamming the nozzle up into my trembling holes to wash me inside and out.

I felt like livestock being hosed down by a farmer. The worst part was that despite my humiliation and discomfort, I was eagerly allowing, and even encouraging, Isabella to thoroughly massage my trembling private parts with the hose. My body needed attention, and apparently, anything would do.

When Isabella was satisfied I was clean, she had me sit down on my poolside lounge chair, and got to work on my hair and makeup.

It was a full morning routine, I realized. She'd shaven me smooth, bathed me, and now she was finishing my look for the day.

My autonomy had been completely stripped away. I was being treated like some sort of show girl -- prepared for a day by a doting trainer.

I continued to be completely unable to shake the arousal from my clouded mind. Every time Isabella's fingers touched my hair, or face, or body, I trembled and melted inside. By the time she was finished working on me, I was a mess once more. My legs were parted in my lounge chair, I was breathing heavily. There was nothing I could do to deny the effect she'd had on me.

"There we go!" Isabella smiled, patting me on the head. She'd finished with my makeup, and given my hair a thorough brushing and tending to. I couldn't see myself, as there was no mirror outside, so if she said I was ready, I had no choice but to trust her.

"Say cheese, Hussy!" she said, and once again I watched her pull her cell phone from her shorts.

She snapped a picture of me, not bothering to wait for me to get into a suitable pose.

"Fuck!" I cried out as the flash lit me up. Even in the brightness of the black yard, I could practically feel the camera flash snap across my naked skin. It felt like someone had given me a powerful spanking, and I shuddered involuntarily at the thought-

"Jane will be pleased to know you've been such a good girl," she said, typing away as she presumably messaged the photo to my co-worker.

Still smiling, she flipped the phone around, to show me the picture.

I gasped, finally seeing the results of her efforts. The picture clearly showed me lying in the lounge chair, legs still parted -- fully exposing my cunt and ass to the lens. My face was equally as clear. The makeup Isabella had applied was bright, and tacky. It looked as if I was ready to go out partying.

The girl in the picture was me, but not me at the same time. Dark eye shadow ringed my wide eyes. Thick, shiny red lipstick ringed my mouth, giving me a dolled up, whorish look.

My tussled hair looked ravishing enough. It was wavy -- no thanks to the hose, but Isabella had somehow managed to force it into a sexy, desirable look.

I looked like I felt ; ready to be fucked.

"Let's get you dressed," Isabella patted me on the head, coaxing me out of the chair, "and then we've got to head out!"

I was led back inside, into my living room. Isabella ordered me to 'Sit' in the middle of the room. I slumped down defeated, getting into position, perching on my haunches with my legs parted wide as she dug into the duffle bag that Jane had left here.

I'd already suffered enough to bring me to my limit, I knew. There was nothing left for me to do but comply now.

"Oh wow!" My gardener-turned-groomer exclaimed, pulling out the first part of an outfit from the bag, "Look at this cute little top Jane's picked out for you! She must really like you, Cassy!"

She held the top up for me to see, and I scowled.

It was barely a top at all. Thin spaghetti straps attached to a thin white piece of fabric. As with the bikini Jane had forced me to wear yesterday, the tank top looked like it had been purchased at some sort of novelty sex-shop.

"You don't look too impressed," Isabella smiled, shaking the top in front of me, "Oh well. Don't think you really have a choice, Hussy. Now -- put your arms up, let's get you finished up."

I sighed reluctantly, and raised my arms. Isabella pulled the top down over me, and then returned to the duffle bag to fetch a matching white skirt.

I let her dress me in what turned out to be a ridiculously slutty outfit. The white top stretched over my chest, barely able to contain my heavy tits. Naturally, I wasn't given a bra to wear. My nipples practically pierced through the sheer fabric of the top, and the tiny garment ended just under my breasts, leaving my lower ribs and stomach bare and on display.

The small white miniskirt wasn't any better. Short enough to practically be considered a belt, the skirt clung to my thighs like it had been shrink-wrapped onto me. My long legs practically spilled out of it, feeling naked and exposed.

As a final touch, Isabella laced up a long pair of high-heel stilettos around my feet.

"You look fab!" She beamed, completing the 'outfit' and admiring her work, "Totally ready to head into town!"

My body was practically spilling out of the ridiculous get-up. It felt like lingerie!

"I can't wear this!" I whined, "You can see my nipples through the top! And I've got no underwear on! One wrong move and this skirt will flip up and expose me!"

To show her what I meant, I took a step forward. The skirt rose up around me, pulling up around the bottom part of my ass. I could feel the cool air of the room on my exposed private parts. Inexplicably, it sent a wave of pleasure rolling up my body, causing me to shiver with reluctant delight.