Your New Job Pt. 04

Author's Note:

Thank you for the overwhelmingly positive feedback!

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Part 4 - Monday Afternoon

You moaned in deep frustration, grinding your knees together as your empty pussy ached, denied orgasm yet again. You laid there for a few moments, your nipples pressed against the cool wood of my desk, drawing deep breaths as your cunt throbbed, trying to regain your composure as I sauntered away.

I washed and clinked around in my private bathroom. As I finished up I clapped loudly, startling you, "Freshen up, my dear. I don't know about you, but I'm famished. There's a cozy little bistro around the corner, you'll love it."

As soon as I said it, you realized that you were hungry as well. You pushed up your lithe nude form, grabbing your dress as you followed me to the washroom, slipping it on over your head with practiced ease. Which is when you noticed the pair of chrome plugs poised on a cloth on the counter along with a small bottle of lube, one plug was small and the other intimidatingly larger. The bigger one looked like it might be similar in girth to my cock...

Examining the dainty little one as you picked it up, you immediately noted how it was much heavier than it looked. Turning it over in your hands as your fingers slid over it's smooth silver curves, the faceted jewel on the end glittering.

You looked up into the mirror to see me standing behind you, the silhouette of my broad shoulders blocking the door as my strong hand came to rest on the back of your neck. "Have you ever worn a princess plug?" I asked, a lopsided grin quirking my lips.

I could see the trepidation written on your face as you gave your head a short shake, No.

"Not to worry. We will take things nice and slow." I said, winking at you as I grinned at the incongruity of my statement and the time we had spent together so far. Sliding my hand down your back as I pulled a towel off of the bar, and with a little flick of the wrist, laid it flat on on the floor. "Kneel," I commanded, continuing while you began to lower yourself, "The most important point to remember about anal penetration," I was gently pushing down on your lower back, guiding you to lay over your folded knees, "is to relax. Can you do that for me?" I lifted your dress up onto your back to display your glowing pink cheeks.

"Yes, Sir." You replied, though the tension in your back and shoulders showed me the brave face you were putting on. The little bottle of lube made a rude noise as I squirted some onto my finger behind you.

"This may be a bit cold," I warned in a silky tone. You could hear my smile in my voice.

You gasped as the cool gel on my finger touched your hot little pucker and I started stroking soft circles. You closed your eyes and began to take deep breaths, as deep as you could folded over top of your knees. Your empty pussy still aching with pent up need. Your shoulders sinking toward the floor as your hips relaxed and turned down, tilting your ass to align towards me invitingly.

Reaching over to the sink I turned on the hot water and carefully placed the small plug under the stream to warm up, my other finger stroking lazy circles around your sensitive ass. "This position you're in, with your knees to your beautiful breasts, allows everything to align internally." I spoke in calm, liquid tones as I applied just enough pressure to push the tip of my finger into your tight sphincter.

You moaned at the shallow penetration as I pulled back to stroke a few more circles before pushing back inside again. Repeating this new pattern I murmured, "Fuck you're tight, girl. We have some work ahead of us if you are ever going to take my cock in here, don't we?" I forced my slippery finger up to the first knuckle to emphasize my question.

Your breath caught in your throat before you moaned, "Yesss, Sir." Flinching as my other hand touched your horny clit again, stroking both erogenous zones together.

"Does that feel good?" I asked. Slowly, patiently pushing my finger deeper into your tight little ass with each penetration. So soon after my cock had vacated your hungry pussy this new stimulation brought you right back to the edge. I stroked my thick finger gently in and out, my other hand slipperily teasing your clit until you twitched and moaned. You were so close again.

My hands left your body. How many times had I teased you right to the edge today? I washed up in the sink and lifted the warm little plug, turning off the faucet.

You laid there breathing deeply as you heard the burp of the little bottle. My free hand came to your lower back, rubbing over the tops of your ass cheeks, still tender and glowing bright pink from your spanking, "Now be an Angel and relax for me." I purred, the tip of the plug gently but firmly pressing into your yearning ass.

"It's going in, but I assure you I will go as slowly as you need, all you have to say is 'mercy' and I will slow down." I pushed just a little harder and the crown of the plug began to stretch you with a little pinch. Your hands came out from under you at the unexpected pain.

"Mercy!" you gasped. As soon as the word left your lips the pressure receded.

"Such a good girl." I praised soothingly, pushing the plug back into your pucker more softly, massaging your tender flesh.

Slowly but insistently the solid steel plug stretched your reluctant little hole. You took a deep, controlled breath as the widest point finally popped past your stretched muscles and your hungry ass sucked it inside. All of the discomfort immediately replaced by an erotic tingle and a deep feeling of fullness, the jewelled cap nesting against your lewdly stretched cheeks.

Wringing out a warm cloth in the sink, I carefully washed all of the extra lube from your throbbing clit, before tidying up around your pretty little plug, "There we go." I said quietly, "A little constant reminder that you are my property... Stand up, please."

You felt your empty pussy twitch as you heard my words, opening your eyes as you took my offered hand and rose to your feet. Your dress poured back down to drape over your ass, hiding any sign of the toy I was subjecting you to. The weight of the plug applying a small pull to your penetrated little anus. Constricting your sphincter teased a small wave of pleasure, as did any squeezing of the muscles in your pelvic floor. You groaned as you realized that while your ass was trapped like this even doing nothing left a subtle submissive bliss radiating from your clenching little hole.

You lifted your purse to the counter, checking your make up as an anxious realization washed over you, and you paused for a moment to stare at yourself in the mirror: you were about to go out in public, again, without panties or bra, because your boss was ordering you to...

Your ass twitched and the heavy plug stroked and shifted with every quiver, sending shocks of pleasure as your cheeks flushed again. You looked back into my office, where I had unplugged my laptop, slipped it under my arm and was heading for the door.

As you followed me you began to fully realize what I had done, the heavy plug tilting left and right with each step. You gasped as the pleasurable sensations in your ass began working their magic on your teased, denied little pussy. I smiled as I handed you your light coat.

You were immediately grateful as you pulled it on, feeling very self-conscious as you covered your aroused nipples.

I held the crook of my elbow towards you, grinning as you slid your arm through mine, leaning against me as you fought with the subtle pleasure that every step was bouncing into you. Feeling that anxious tightness in your chest as we entered the elevator, every erotic footfall taking us further from the privacy of my office.

As soon as we left the building you gasped, the gentle breeze sliding up under your skirt and licking across your moist, naked lips. I loved the concentration written on your face, biting your lip as you worked to stay composed while we walked.

We rounded the corner and a new stab of worry arose as you saw a packed restaurant patio full of people enjoying their lunches. Pleasant instrumental Italian music playing over the outdoor speakers.

You blushed again when we arrived, half a dozen conversations going on around us as a small gust of wind tickled at the hem of your dress, your hand shot down over the billowy fabric even as you realized your overreaction. Flustered, you stepped aside as a few business men walked past, leaving the establishment.

A tall and slim young waiter came out to the patio and smiled at us, addressing me, "Welcome back! I think your favorite table just freed up." he said, nodding toward the interior.

"Thank you, my good man," I smiled back cordially as I slipped my hand around your waist, resting it politely but possessively on the top of your ass, guiding you inside ahead of me.

Blinking to adjust to the dimmer light within you scanned around for an empty table in the busy little place. I leaned over and spoke into your ear, "Second booth from the back." As we headed down the cozy aisle you noted that most of the diners had finished their plates, it seemed we were arriving just at the end of the lunch rush.

You walked carefully to the empty booth. The quaint red and white checkered tablecloth hanging down almost to the floor, draped over the the circular table nested within a cozy, plush three-quarter-circle bench.

I politely motioned for you to sit first, pointing to the seat that would have you facing the rear of the restaurant, "Let me take your coat, my dear."

Your stomach sank as your eyes flitted from me to our waiter while he casually looked away, "Yes, Sir... thank you, Sir." you mumbled as you slid your protection down off of your shoulders, quickly slipping into the booth.

Which was the first time your tender cheeks had touched down on something since your spanking. Your sharp hiss of breath drew a curious glance from our attentive waiter as you blushed anew and gingerly tried to find a comfortable position. While you slowly lowered yourself down the plug nestled within you began to push in deeper, applying pressure and stimulation you had never experienced before.

You took slow deep breaths as you worked at maintaining a neutral expression, shifting subtly from one cheek to the other as you tentatively settled in, stroking the plug left and right inside you. Your mind embarrassingly dancing to the thoughts of how close the straps of your dress were to slipping from your shoulders, and how only centimetres of fabric covered your bare pussy.

"Again, welcome folks," our waiter smiled, "My name is Samuel and I will be your server this afternoon." He handed us the menus, "Can I start you off with anything?"

I glanced at the little condiment stand on the table, the paper insert proclaiming Margarita Mondays! "How about a Margarita for each of us?" I asked as I slid into the booth from the other side, shuffling around until I was sitting beside you, our knees just brushing.

His eyes slid down over you, pausing for the briefest moment on your nipples, softly hinted at through the thin fabric of your dress, you nodded self-consciously as you blushed, feeling flustered yet aroused at the attention, and that I hadn't deigned to check with you before ordering, "Of course! I'll give you some time with the menus while I grab your drinks!" he smiled cheerfully, then hurried away.

You picked up the short menu and quickly located the healthy options. Just as you had settled on your choice Samuel returned with our bright green drinks with their lime wheels split over the edge.

I thanked him kindly before he took our orders, a chicken salad for you, and a corned beef on rye with a side salad for myself. He bowed and excused himself.

Holding my glass up toward you, "A toast: to taking advantage of our wonderful new opportunities." I declared, winking at you. You clinked your glass with mine before downing a large gulp of the sweet libation.

On an empty stomach you very quickly felt your drink begin to go to your head, the warmth calming your nerves.

I opened my laptop, pulling up some data I had collected to show you, "So I took the liberty of calculating your first pay cheque, along with your first year - just for completeness." I spun the computer to face you, having already highlighted the final figures so they would stand out against the tax information, "I hope the numbers are to your liking." I grinned.

Your eyes widened at the values staring back at you. I had mentioned your salary during your interview, but this was the first time you had seen everything laid out. "Wow..." Was all you could muster through the haze of your sore rump, your tight ass squeezing on the plug within you, your relentlessly teased pussy still tingling.

"That is, of course, if you choose to stay in my employ." I said as I watched your eyes, "I don't want you to feel coerced in any way, my dear."

"Of course not..." you stated, taken aback.

"'Of course not, *Sir,*'" I admonished grinning, eyebrow arched.

"Of course not, Sir." you blushed.

"Good girl." why was it so arousing when I chastised you?

"I wanted to be clear right up front that I take your 'golden parachute' very seriously." I said, referring to the last item you initialled on your contract addendum, your severance package. "If, for any reason, you feel I am being too demanding, you have every right to leave. And I personally promise I will never order you to do anything you haven't agreed to in our contract. Barring any criminal wrong doing on your part, you are entitled to a half year's pay as severance." I smiled at you affectionately, "But you and I both know what you've given to me with that signature, don't we? And I intend to enjoy you however I desire, within the bounds of our agreement."

I paused to let my statement sink in, "But, as this is your employee orientation lunch, we must use this opportunity to go over your future duties."

We spent the rest of the time waiting for our food discussing specifics as my strong hand rested under the hem of your dress, half way up your bare thigh.

Samuel arrived with our food and we dove in while I ordered us a second round of drinks.

You were beginning to feel much more relaxed as you glanced over your shoulder and the shielding edge of the booth, and noted that most of the patrons had already cleared out.

As we finished eating I brought up a business trip in a few weeks that I needed you to attend with me, we would be out of town for a few days, sharing a single high end hotel suite, and I expected your best behaviour.

We sipped on our drinks as the waiter stopped by to clear the table, leaving a dessert menu for us to peruse.

"The other part of this business lunch is an obedience test, Angel." I stated, my demeanor suddenly becoming more serious. "If you think back to the contract you signed, you have given specific written consent to a broad range of demands from me. Your dress code, for example."

Your heart leapt immediately as you glanced around, "Sir?" Thinking about how I had leveraged your dress code twice already to demand you strip naked for me.

"If I were to order you to pull up the front of your dress and spread your legs so that I may enjoy your pussy, or I would give you another twenty swats with the ruler, that is completely my prerogative and you would have no choice but to obey or be punished, wouldn't you?"

You shifted nervously in your seat, the movement causing an immediate sting in your tender cheeks, as your clenching ass stroked the plug inside you," Yes... Sir." you responded meekly.

"You have until the count of three to bare your pussy for my inspection, or you will regret it." my stern tone reminding you of a mere hour ago, naked and stretched over my desk, when all you could do was apologize and endure.

"One."

You glanced around sharply as as your fingers grabbed the hem of your dress.

"Two."

Your cheeks ached as you pulled back while rolling your hips forward and spreading your knees lewdly, still mostly covered by the table, the change of position pushing your plug just a little deeper within.

"Three." I paused to enjoy the view you had just presented me, "such an obedient little slut for me, aren't you?"

You looked over your shoulder again nervously, quickly nodding. The chatter from a few tables on the patio drifting back. Inside only one other table at the front was still occupied, well away from us.

"I'm sorry, I didn't hear you." I intoned menacingly.

Bam! You almost jumped out of your skin as Samuel barged through the doors from the kitchen only a few metres away, flipping your dress down as you bolted upright, driving your inflamed cheeks down into your seat painfully. Your plug shifting and bouncing. He didn't even glance over as he headed past to the patio.

"Did I say you could cover up?" I cooed, your heart already racing as you recognized the soft tone I had begun each of your punishments with.

You pulled the hem of your dress up again as you gingerly leaned back, a quiet, "Sorry, Sir." mumbled from your soft lips. Just saying the words while your ass ached reminded you of your last spanking. Your exposed pussy throbbed.

"Better." I stated simply as I leaned forward on my far elbow, licking the finger of my other hand before sliding it down between your legs.

You gasped as my strong finger slid between the lips of your pussy, your knees involuntary spreading wider under the table as you closed your eyes in embarassment. Teasing the gentlest circles around your hungry little clit... too gentle. You pushed your hips forward just a little for firmer contact before you realized how wanton you were acting, blushing even deeper.

You opened your eyes in confusion as my fingers left your pulsing clit, pulling your dress back down as they went, "So, are you two ready for dessert?" Samuel asked loudly in his chipper tone from behind you as he walked back from the patio.

"Still considering," I responded cheerfully, "but thanks for thinking about us."

He nodded as he walked by, continuing on to the back.

"Speaking of dessert..." I said smiling in a conspiratorial tone.

You held up your hand and shook your head, about to voice that you wanted to skip it, until you looked into my cold, demanding eyes, "If I tell you that you are going to slip down under the table and you are going to suck my cock for dessert, then that's exactly what you are going to do, isn't it?"

Your eyes darted around, "But I can't-"

"'Can't' or 'choose not to'? Because we both know you were sucking my cock more than once this morning, slut." I said, pitilessly. "This is an obedience test, my little Angel. If you remember back to the contract you signed I am well within my rights to demand this of you." pausing for a moment before adding, "And I get to stipulate a punishment if you refuse. So what will it be? Forty swats with the ruler maybe? Or how about no orgasm for a week?"

Your empty pussy throbbed as you realized I was correct, and that deep down somewhere you wanted to obey this order. You glanced around nervously, noting that no one else was anywhere close, pleasant voices still drifting in from the patio. You could feel your heart racing as you slid and twisted awkwardly down under the table.

It took a bit of work to squeeze yourself in beside the post of the central table leg. I twisted off-centre to align with you as I unzipped my trousers and we pushed the draping edge of the table cloth behind your head so I could look down into your eyes as you served me.

You fished my semi-hard cock from my trousers as you perched on your knees, shrouded from the aisle by the checkered table cloth. I scooted my butt forward a little and leaned back to get a better view.