Short Story: Office Shenanigans

"... and here are the accounts that I have passed for this month, for your approval." I handed her a stack of entries passed during the month, smiling nervously as my boss took it over lazily, and without even so much as glancing at it, she signed it and tossed the documents back at me.

I stared at her face, a sculpted and well-defined jawline, dark red lipstick, matching with a low cut black romper that started between her breasts and ended above her knee. I could see the slight outline of her ample breasts, the bridge of her bra clearly visible to me. Would I look like this 5 to 10 years later?

She looked up from her keyboard, her coloured contact lenses a mesmerizing turquoise, asking me if there was anything else. I blushed and hoped she did not catch me checking her out. I grabbed the documents and excused myself, knowing I have more work to complete.

I shut the door gently behind me and noticed you standing at her door, a new intern. Oh right. Your usual weekly report on how you were doing at the company. I smiled awkwardly, as I do around new people. You smiled and knocked gently on the door, while I hurried along down the corridor back to my cubicle.

As I sat down and perused through my documents, I realized my boss missed out signing on certain important pages. Heaving a sigh, I ambled my way back to her personal cubicle.

I waited outside the dark mahogany doors, knowing that my boss did not like to be intruded upon whilst in a meeting with another person - being you. I peaked through the window beside, the blinds were drawn down but I could see a little between the slits of each fold of the blind.

You were sitting in front of the desk, and I had a side view of your features, young and seemingly innocent, or so I thought. Yet the state of your clothing betrayed that. From earlier on, your blouse lost its top 2 buttons and your chest was almost, if not more, exposed as compared to my boss.

Your skirt was hiked up to expose the upper thighs, the little triangle of panties just slightly visible to me from my view from the window.

What surprised me the most was that my boss stood towering beside your petite frame, her gaze no longer a lazy glance, but a flaring stare, filled with purpose and ambition.

I watched at she lay her middle finger below your chin, tilting the small head up to look at her. I see her lips and yours moving in response to whatever she was saying, but I could hear nothing but murmurings behind the soundproof glass.

I could do nothing but watch as she moved her fingers downwards, her nail dragging across your soft, white flesh, stopping to rest at your third button, halfway down your torso. With two fingers, she expertly released the third button, flipping your blouse open to expose your chests, clad in a nude coloured bra that covered your gently heaving breasts.

My boss placed her hands below your chin once more, this time tilting your head up, till you had to stand up from your chair. Her other hand pushed aside the chair from behind you, and she slowly walked forward, placing her stilettos one in front of another, full of feminine confidence. In comparison, you looked like a trapped bunny, stumbling back in your flats and pencil skirt, which was still hiked up around your upper thigh.

Your back contacted the cabinets behind you, but it did not shock you. Rather, it seemed that you expected it to. Quickly, the last 2 buttons of your blouse came off, and my boss placed her hands around your collar, pulling them downwards and off your shoulders. I thought I saw you shiver, probably due to the cold... or was it excitement I saw in your eyes?

Reaching to the cabinet beside that I have never opened, my boss pulled out a pair of handcuffs, matte grey and solid looking, like one of those meant for high security criminals. She hooked one ring around your hand, and raised that hand above your head to loop around the handle of the upper cabinets, and the other ring found your other hand, locking you in position with both hands above your head, like a lamb prepared for slaughter.

My boss stretched her long fingers around your face, holding your head up in her hands. Her other hand traced downwards and found the hem of your skirt, lifting them higher than before, exposing your innocent white panties.

Her nails dragged across your skin, and I watched you shiver in her hands, your face almost breaking away from her gaze. You struggled to keep your eyes fixed on her, and your mouth quivered under her intense gaze. Her thumb and pinkie stretched apart, forcing you to open your legs as her sharp nails poked against your tender inner thighs.

I held my gasp as I watched her bring her knee swiftly up to your private region, and I felt my insides flip as if I have been kicked between the legs myself. I reached downwards to hold my mound, feeling your pain like my own. Yet you did not falter, but perhaps your blinked a little from the sudden impact.

Her knee remained there, between your legs, pushing you against the wall, and I saw you tiptoe, trying to reduce the pressure of your own weight upon your crotch.

Involuntarily, the action caused you to grind against her leg a little, and I felt myself grow warm between my legs for you, feeling the need to relief myself.

I watched my boss smile, a menacing look I have never seen before. She let you go, leaving you on your feet, your hands still above your head.

You breasts heaved with each breath, heavy and laboured. I saw your eyes widen as you gazed straight forward, it must be something you see my boss grabbing from her desk.

She returned into view with a pair of scissors, and I felt slightly afraid for you. Should I save you? I decided to watch a little longer. You were not screaming yet, so it should be safe... Right?

I watched as she brought the scissors down to your panties, the open blade sliding under the hems of your panties. With two snips, the top of the panty fell forward, held in place by your upper thighs.

With force, I saw her pull the cloth from underneath you, the cotton material dragging across your entire pussy lips. I saw your mouth open a little, not too sure if it was in ecstasy or in pain. There you stood, shaven bare between your legs. I swear even from outside the office, I could see your pussy lips moist, a trail of clear liquid dangling from your pussy lips.

I watched on as she unhooked your bra clasp from the front,  revealing to me a set of firm and young breasts. She unzipped your skirt and let it fall to your ankles, leaving you fully in the nude with only your flats.

You blushed in your nakedness, embarrassed to be exposed in such a manner, your hands tied above your head, unable to cover up even decently despite your nakedness. Your nipples hardened in the cold air, brown little raisins sticking out from two round mounds on your chest.

I must have been transfixed by your nudity that I did not notice my boss bring out a stick with a leather patch at the top, a riding crop. I watched as she scratched her nails upon your inner thighs, motioning for you to open your legs.

She brought the crop to rest on your pussy, the leather scooping out the trail of clear fluids dangling from your private region.

With quick succession, she brought the crop away and slapped it hard against your young pussy, an audible slap sound that I could hear even outside the soundproofed room. The sound was sharp and loud, yet the contact point sounded wet, moist with your pleasure fluids.


I felt my own breath quicker than it was before, and I felt a familiar heat between my legs, aching, wishing I was in your stead. I squeezed my thighs together and felt my own panties having a moisture of their own.

A few more times the riding crop went, tracing around your thighs, across your flat stomach, circling your breasts, but each slap landing upon your wet pussy, the leather staying in place for a tad bit longer while your absorb in the shock, feeling the material against your sensitive spot.

Your pussy reddened with each slap, yet you got wetter as well, the trail of fluid now long enough to drip onto the velvet carpet below. Yet there you stood, helpless and bound, biting your lips harder with each strike of the crop.

My boss placed her riding crop down and came close to you, observing your eyes - needing, wanting, lusting for something.

I watched as she traced her fingers below you, your legs wobbling with the need to be touched, an almost primal need waiting to be filled.

She cupped her hands onto your mound and I saw your gasp, your eyes closed in anticipation of what was to come. I saw your mouth whimper a bit, as if begging, pleading for release. I could only imagine the pain and pleasure coursing through your red and swollen pussy, warm from the beating and sexual need.

She removed her hands and she brought her knee up to between your legs once more, this time gently. Yet you grimaced with the pain of her skin being in contact with your pussy.

I watched as she whispered into your ear, and you replied while closing your eyes, a look of relief upon your face.

You started to buck your hips as my boss stood there, her thigh up against your swollen privates, as you grinded your pussy against her. With each forward trust, I watched as you got off on the mixture pain and pleasure, each movement causing you to grit your teeth together. Yet the desperation was present, the need to find release.

I watched as your fluids were spread across the thigh of my boss, and she gently hiked her own skirt up to prevent it from getting wet.

Your grinding was consistently getting rougher, each hip movement more vigorous than the last. I watched as my boss gazed at you with lighted eyes, this nubile girl getting pleasured upon her bare skin. Your wrists were red from the metal pulling at them, constricted in their cold embrace.

With one last thrust, I watched as you arched you back and pressed your pussy against her thigh, an orgasm ripping through you, relieving you of your need. Your head was tilted upwards and your hands strained against the handcuffs above you. Your mouth opened in an 'O' and I swear I could hear a hint of how loud you were moaning from the release from the slight moans I could her from outside.

My boss lowered her leg as you leaned with your back against the cabinets, your petite body trembling from the aftermath of the orgasms, each tremor a sign of what transpired earlier.

I could see for myself how wet you were from the patch on my boss's leg before she wiped it down, the small patch of dampness upon the carpet upon which you stood.

From the same cabinet, she retrieved a key to uncuff you, massaging your sore wrists with tender loving care. Despite of how rough she was with you earlier, she held you close to her breasts and caressed you lovingly.

She helped you get dressed and I watched as she tossed the ruined panties into the bin, giving you a sly grin as she did. You pulled the skirt down around your swollen privates glad to be covered once more.


Straightening up, I realized you were done with your 'meeting'. I hurried away from the door and turned to appear as if I was just walking down now, and I saw the door to the room open just in time.

I fumbled with my documents and they fell to the floor. You saw that and hurried forward to help me, squatting down to scoop the pieces of paper off the carpeted floor. I mumbled a soft thank you as I helped myself to the paper, staring down the length of the skirt, seeing your bare pussy at arms length away, red and sore.

You must have noticed that as you quickly stood up and straightened your skirt, a shy blush upon your face.

As you hurried away, I knocked and met my boss, greeting her lazy gaze. While I asked her to sign the documents, I could not help but take in the smell of sex and arousal in the room.