The Helldesk Ch. 02

I motioned to the suitcase and watched her slowly crouch down to open and start rifling through her traveling wardrobe.

"Oh, by the way my little gateau, there are a couple of ground rules: Number one, you get to choose any heels so long as they are tall enough for my liking, and you get one more thing to wear other than the butt plug. Oh, and I guess you can probably have a coat should it happen to rain, because I'm generous like that."

She glared at me at the mention of one item, probably wishing she could wear panties to hide the butt plug or make sure it didn't come out. However, I was under no illusions as to the likelihood of that thing coming free with anything short of a pretty violent spanking or caning. It had taken a seriously firm touch to get it all the way home, so she could look as pouty as she wanted. A dress, heels and butt plug were all any good slutcake needed to have fun on the town!

After rummaging around for a few minutes, she held up a very girly, but entirely too chaste, sleeveless floral sundress. I shook my head and she held it against her torso encouragingly. I let my brow furrow and sink into a frown as I put my hands on the arms of the chair, as if to rise. She dropped the dress over the edge of the desk and dived back into the case with alacrity and I settled back into my throne. She seemed eager to please, but I wondered how much of that might be an act, and whether she was trying to lull me into a false sense of security. I had a feeling I had quelled her rebelliousness earlier with the ruler, but she could easily be a long way from truly broken, so I resolved to sleep with one eye open at all times.

Her next attempt hit the bullseye. A plain black, figure-hugging cocktail dress that looked like it would strike just the right balance between sexy, slutty, and elegant. The cleavage was distracting without being too revealing, the hem was just far enough up the thighs to make you take a second glance without showing anything too untoward on a flight of stairs, and the lack of ornamentation or frills would only work to more truly showcase the body wearing it. I nodded my approval and suggested she put it on. She turned, as if to head to the bathroom, and I rolled my eyes.

"Just why, exactly, would you need to go to the bathroom in order to put it on?" I laughed. She colored and reached it above her head and slid it down her very lithe torso. As I had thought, it looked stunning, and I licked my lips in anticipation of removing it later, just when she was least expecting it.

By now it was a little before 9pm, and the restaurant I had in mind would be closing at 11pm. With half an hour or so to get there, a little time for an aperitif and for our orders to be prepared, we should probably be finishing around closing time. Perfect timing! I couldn't stop the evil grin that was threatening to split both cheeks in two. A ghost of a frown flickered across her brow before she lowered her eyes and asked demurely "Does Sir approve? Are any adjustments necessary?"

"No my little toy, you look good enough to eat. Literally. If I didn't know better, I might have thought you brought it with you expressly to make me salivate. Alright let's get this show on the road!".

With that, I started tossing things in the relevant bags - work stuff in the rolling bag, kinky accessories in the duffel. After reminding my prize to pick a pair of heels to match (she went with some strappy, black, four inch Louboutins), I told her to grab her suitcase and to toss the rest of the stuff I had taken earlier from the kitchen into the sink. Apart from the bag of popcorn. I was keeping that for later, in case I needed a snack. It would teach the former owner a lesson for thinking it was safe in a communal kitchen.

With the last of the earlier toys cleared up, and with her laptop stashed in the top of my rolling bag, I set off towards the elevator, my new toy trotting after me in an effort to catch up before I reached the elevator. As we sank toward the infernal depths, I looked at the view in front of me. It would have been one thing to have someone I wasn't particularly attracted to as my slave, but this particular one was quite spectacular. I was tempted to lean forward and enjoy the feel of her in that figure hugging dress, but there were cameras in the elevator, and I didn't want to leave any incriminating evidence.

As we hit the first sub-level, the elevator glided to a halt, and I held up the laptop as if to show her something. "Get your car and meet me on the corner of Vanderbilt and Main Street - I'll be in a black Beemer with brass colored wheels. Five minutes."

She nodded, and I walked past her into my office, the elevator doors sighing their disappointment at not getting to see what would happen next. I dumped the rolling bag, picked up the duffel and, flicking the lights off as I pulled the door closed, walked back past the elevator to the staircase leading to the lobby. I waved to the night security guard as I swiped out, and walked the short distance to the parking lot used by the 'not so high and mighty'. After dumping my bag in the trunk, I jumped in the front seat and pulled rapidly out onto the street in just the same way I would have done on any normal Friday evening.

It was a short ride to the agreed upon meeting place, and I didn't have to wait more than a minute or so before an expensive rental car pulled up next to me, the passenger window rolled down to show my prize looking perfectly at home in the driver's seat.

"Your hotel - lead on," I said as I held up her phone, reminding her that I hadn't yet returned it.

She accelerated smartly away, and I had to pay attention to the rest of the traffic to keep up. It didn't take more than ten minutes to pull up in front of one of the nicer hotels in the neighborhood, something quite in keeping with her level of corporate privilege. I got out of my car, and walked over to where she was retrieving her case from the trunk. As I pulled the keys from her hand, I turned to look at her and said, "You have exactly ten minutes to check in and get all pretty. For every minute thereafter that you are late getting back here you will lose one of the three items you have to wear, that little emerald plug not included. Any later than that and I will add ten strokes of a nice little rattan cane I own for each minute. And that punishment will not be limited to the backs of your thighs. Palms, breasts, pussy lips and feet will all be game."

She blanched and almost ran for the lobby, dragging her suitcase behind her. With her out of the way, I grabbed my duffel from the trunk of my car and pulled the small remote vibe from the box I had squirreled away in the bottom and stuck it in my jacket pocket before tossing the bag into the rear of her luxo barge - you could never accuse me of failing to plan ahead!

I smiled to myself as I settled into the driver's seat of her rental. The warmth and softness of the plush, hand tooled leather was about the most cosseted I had ever felt in a car. I reached down to the side of the seat and found the controls to glide me a few inches further away from the pedals. I looked around at the leather and real wood veneer, and marveled at just how much they must be paying her for her to be able to command a vehicle of this quality whenever she visited. She might be even further up the ladder than I had initially supposed. That thought only brought a grin back to my face at the idea of a VP-level piece of skirt giving me a blowjob in a hotel parking lot. I leaned back and luxuriated in the perfectly cooled interior, my impromptu daydream causing a stirring in my shorts.

I checked my watch and realized that my daydream had lasted longer than I thought. Eight minutes had passed since I had last seen her toned rear hightailing it towards the hotel lobby. The prospect of getting to use my cane on her already savaged behind was enough to make my mouth water. One and a half minutes to go, and she would be in jeopardy. I imagined she might prefer a caning to the prospect of going into a public restaurant naked, so if she was a couple of minutes late I expected she would probably give up the shoes with little argument, but not the dress. Maybe in a more managed environment she might be prepared to show off that quite delectable figure to others, but I doubted she would toy with the prospect of getting arrested for public indecency.

As the seconds ticked away, and the hands on my very sadistic watch hungrily devoured the time leading up to her deadline, I kept my eyes fixed on the entrance, counting down in the back of my mind until I looked down and watched them sweep eagerly into the tenth minute since she left. I smiled and unconsciously licked my lips, looking up to see whether she had appeared yet. The answer was no, and as the watch solemnly counted her passage into deeper and altogether hotter water (pun intended), I asked myself if I would really make her walk naked into a public restaurant.

Our intended venue was a place I had been going to for over five years now. I'd done some work off the books for the owner when they first opened and had gotten to know both him and the guy who invariably managed the evening shifts for the busier Friday and Saturday nights. The owner was almost never around, which was a good thing as I doubted he would have been entirely sanguine with the idea of what I was planning.

Carlo the duty manager, on the other hand, was someone I had played poker with on a regular basis for about a year, and had also enlisted his assistance in scoping out some of the tastier bar and wait staff as they were signed on. I'd picked up more than a couple of these tasty young wenches using some insider info gleaned by Carlo from his recruitment interviews. By inserting them strategically into conversations with some of these sweet, naive, and very enthusiastic young ladies, I was able to make it appear as if I had an uncanny grasp of what they enjoyed and what made them tick. Carlo was someone I knew I could trust, and I planned to enlist him in the debasement of this much more exclusive bird of paradise. I knew he would be more than up for it.

Glancing down at my watch once more, I realized that it was almost twelve minutes since my slut had departed and things were about to get truly interesting. I jumped slightly as the passenger door was yanked open, and the subject of my attentions threw herself into the adjacent seat, breathing in a way that dragged my eyes down to her perfectly delightful breasts. Her nipples were quite evident, standing very erect underneath the black fabric and it was all I could do not to stare. However, there was something strange going on with the fabric of her dress down between her thighs - I would have to come back to that shortly.

I made my disappointment evident as I pouted and held up my watch to show her just how close she had been to either giving up everything she was wearing, or in having to negotiate the return of her dress in exchange for some equally significant forfeit. "Twelve minutes, slutlette. What are you going to give up?"

With barely a shrug she removed her shoes and pulled the seatbelt across her torso to nestle it in a most enviable location. I paused and turned to face her. "So," I reminded her, "you get to wear one item - the dress, so it appears - in addition to that cute little plug. I believe I was quite clear on the rules?" She nodded and settled carefully into the seat.

"Lift up your dress," I commanded. He face twitched slightly and for a moment she didn't move. Then she slowly lifted the hem of her dress to her crotch to reveal a flesh colored band around one thigh with a small pouch attached, almost hidden between her thighs. I tutted and shook my head slowly.

"Hmmm, maybe we have a different understanding of what one item entails?" I asked. I extended one hand towards her and waited. She sighed and leaned forward to slip the band down her thigh and off her leg. She dropped it into my hand and smoothed the skirt back down her thighs. I opened the thin pouch to discover a couple of hundred dollars in cash, a credit card, her hotel room card, as well as a small, neatly handwritten piece of paper with names and telephone numbers. Interesting. That would definitely bear investigation later on.

I continued to stare at her, and watched her swallow nervously, her eyes seemingly fixed on some (apparently fascinating) point somewhere out beyond the windshield. "Let's try that again - but all the way this time you little tart," I told her, the menace in my voice causing her to start as her eyes snapped round to look at me.

"Sir?" she asked nervously, her eyes wide and reminiscent of a wild animal watching a predator approach.

"Because of your efforts to cheat, you will take the dress all the way off and prove that you have nothing else hidden either underneath, or in the fabric itself." The fear I could almost smell told me that the prospect of being naked in a car no more than thirty yards from the door of an exclusive hotel was not a prospect she relished. Probably not an exhibitionist then, maybe not even as confident in her body image as she should be, which might go some way towards explaining the padded bra and the little girl panties I had destroyed earlier.

"No, please, I can't get caught doing something like that, I might lose my job... I..." Her eyes were beseeching, her distress apparently genuine. She probably hadn't yet realized that she had laid a hand on my thigh in an effort to connect with me.

"Nope. Not going to work, you have to learn your place," I told her. "Did you really think you could put one over on me so easily?"

Before she had time to move, my left hand darted out and latched onto one of her very apparent nubbins. I relished the way it felt between my fingers as I squeezed down hard causing the pupils in those big doe eyes to widen even further and her other hand to leap to cover her mouth in an effort to stifle the involuntary cry that escaped her lips. I continued the pressure, adding a twist to the equation, and she moved the hand from my thigh to her breast, fighting to remove my grip in an effort to reduce the pressure I was applying.

"Put your fucking hands in your lap before I see if there are some nice bitey jumper cables in the trunk of this car," I spat, as her cry turned into a steady whimper that leaked out from behind her hand. She slowly dropped both hands into her lap, the twitching thereof showing that it was all she could do not to reach back up and try to get me to let go of her nipple. I squeezed a little harder and her eyes clamped tightly shut as her whimpers became more pronounced. I leaned forward to remind her, "The dress comes off over your head as soon as I let go, and then, hopefully, we can move on to the very overdue subject of dinner."

She nodded, eyes still clamped shut, and I let go of her and sat back in my seat, watching as she wiggled out of the dress and handed it across to me. I turned it inside out, watching her slink down further into the seat, out of the corner of my eye. I checked the hems and underarm seams for any hidden items and told her to sit up straight.

As I watched her grow a couple of inches in her seat i could see her eyes darting around looking for people, cameras and possibly photographers. Her hands were spread as widely as possible covering her little soul patch and the juncture of her thighs, her gaze still fixed somewhere off through the windshield again, probably praying with all her might that no one would come walking out into the parking lot in the foreseeable future.

I smiled as I contemplated what I was about to tell her. I reached across and undid her seatbelt, watching it retract rapidly into the B pillar, leaving her entirely unprotected. "Given your performance so far, I'm giving you one last chance to behave in the manner to which you agreed - as a slave, bound to do exactly what I ask, promptly and without question. Do you understand?"

She nodded, mutely, and waited to hear what I was going to ask of her.

"Turn around, so that you are kneeling on the seat facing backwards with your butt pointing towards the windscreen. Do it now, without question, and show me whether you have lived up to the other condition I specified earlier."

There was a momentary pause before she swiveled around in the seat, grabbing hold of the headrest, kneeling backwards on the seat, her butt lifted a meager six inches above her ankles.

"Higher," I prompted, watching her lift her rump maybe another whole inch skywards. "The longer you take to satisfy me, the longer you will be in this position," I cautioned her. With that, her nether regions lifted rapidly up to the same height as her shoulders, and I nodded my approval.

"Very good, now that wasn't so difficult was it?" I quipped as I watched her head twitching back and forth as she now attempted to scan the parking lot through the rear window. "Don't you dare look round," I warned as I shifted in the seat to get a better angle.

I raised my hand and felt around behind her to where I couldn't quite see, and was just a tiny bit surprised to find the shallow curvature of the butt plug nestled right where it should be. I wondered whether she had kept it in due to fear of reprisals, or because she genuinely enjoyed having it in there. She was starting to quiver slightly, probably out of nervousness, and I slid my fingers down into her folds and started to massage her clit and outer lips in long lazy circles.

Her mouth opened and her eyes glazed over a little as she stopped paying the majority of her attention to the parking lot. I tightened the orbit of my fingers and increased the pressure I was applying to the main focal point of her pleasure. She sighed and arched her back slightly, bringing her lips up into closer proximity to my fingers. I increased the speed of travel a little more and her sigh transformed into a low moan, her hips pushing back very slightly every time I passed over home plate.

Suddenly she stiffened, and hissed, "Someone's coming!"

As she started to turn around and sit back down in the seat, I shoved my other arm under her hips to hold her up and delivered a resounding smack to her rear with the hand that had been pleasuring her just a moment before. She leapt a couple of inches into the air and I warned her that if she moved from the position I had specified, I would kick her out of the car and leave her there to explain her predicament to anyone who found her. I also reminded her of my previous threats to release videos randomly and without warning - something she should assume would be standard punishment for any disobedience on her part from hereon out. She quivered, but held her place, her wounded gaze betraying just how cruel she obviously thought I was. I couldn't help but smile as I wondered why she thought that would affect me.

I cast my gaze towards the driver's side mirror and could see a couple walking arm in arm across the parking lot towards us. I checked the side window and noted that the tint was definitely a couple of shades darker than the windscreen. If she was lucky, they would probably walk straight past, enveloped in their own little bubble.

As we waited, the voices of the potential intruders becoming gradually louder, I could see my slave starting to shake, her thighs shifting as she couldn't help rubbing them together, probably in an attempt to alleviate the heat that I had just felt emanating from her very wet and juicy hole. The initial lack of stickiness I had felt earlier probably accounted for the amount of time it had taken her to get back down to the car, in addition to the more obvious once over she had given her hair and lip gloss.

The interlopers were no more than a couple of car lengths behind us now, maybe less (as the written warning in the mirror proclaimed), and I looked over to watch the play of emotions on my captive's face. She had turned her head slightly to watch them, and as they drew level with her car, I caught her licking her lips ever so slightly. From the noticeable tang of pussy in the air, it was clear that this exercise was starting to get to her. The thrill of possible discovery was outweighing the fear of the reprisals that might follow if her luck did indeed run out. As the couple passed my door, less than ten feet way, and kept walking, it was obvious that they were completely engrossed in their own conversation. My companion's shoulders sagged slightly, and her exhalation matched my own as her head dipped forward to rest against the seat back.