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.

Short Story: Caught

"So... Both of us know why you are here right?" Clarissa sat silently in front of her teacher's desk, trying to stare anywhere but at her form teacher.

"Yes Mr Lim." She shifted her weight about the chair, wishing this was already over.

"So please tell me what you were doing, Clarissa."

"I just... Wanted... To see him." Clarissa stuttered, knowing that that was a lousy excuse for being in a male's toilet, when she could meet her boyfriend just about anywhere else in school.

"I believe you and I know the amount of trouble you are in, Clarissa. Please be truthful about what exactly you were doing, right from the beginning."

Clarissa thought of how she stumbled into the boys toilet, all giggles and butterflies in her stomach. She grabbed her boyfriend about his waist, squishing him for the first time after the long holidays. She looked to Mr Lim and shook her head.

"Were both of you doing anything that you should not be doing?" Immediately her mind went to the french kiss they shared in the first cubicle, his hands cupping her breast underneath her blouse, her own hands massaging the growing bulge over her boyfriend's pants. Clarissa shook her head more, and looked down at her shoes.

Mr Lim sighed. "Well, I guess I have to call your parents down if you're so uncooperative."

Clarissa panicked, knowing how her parents were strict with her. They would not tolerate any of this nonsense. "Please. No. Don't do that. I will tell you everything."

"Please go on."

Clarissa recounted of how she rearranged to meet her boyfriend on the 4th floor outside the male staff toilet, which they thought no one would use. She said they started kissing at the door, and her boyfriend started to undress her...

"Show me." Clarissa paused. She stared at the phone on Mr Lim's desk, knowing her parents were only a call away. She had to comply.

She continued with her story, sharing with Mr Lim how her boyfriend unbuttoned her blouse button by button, and she unbuttoned her blouse as she described that she liked it like that. There Clarissa stood with her blouse unbuttoned, her fair skin underneath only covered by her bra.

Clarissa continued, telling of how her boyfriend lifted her skirt up. Mr Lim eyed her skirt, and she got the cue. She lifted the hem of her skirt up, revealing a pair of panties that matched her bra.

Goosebumps stood on her exposed legs, and it was not due to the cold of the air conditioned staff room. She traced her fingers across her bare skin, running them along the tiny bumps of her hair folicles. Her senses were heightened and she felt herself twitch a little from the contact.

She tucked the hem of her skirt under the waistband of her panties, elaborating on how her boyfriend touched her. She groped her breasts just as how he did, showing Mr Lim how she liked it.

As she reached down to her panties, she felt her own wetness, something that she did not realise earlier. She was getting aroused from recounting what happened. Clarissa paused for a moment while Mr Lim watched, his attentive eyes on her.

"Did both of you continue?" Clarissa blushed, knowing full well that they did. She nodded. "Show me what he did next."

No words were needed, Clarissa then started to fondle herself, massaging her breast and her pussy. Despite the layer of clothing between her skin and hands, she felt pleasured by the contact, her senses heightened, her face flush with the blood of arousal.

She leaned against Mr Lim's desk just as she leaned against the toilet seat earlier, getting herself comfortable. Lost in the heat of arousal, Clarissa suddenly did not bother about her teacher being there at all.

Her hands moved underneath the fabric of her underwear, feeling the tush of her pubic hair, the mound of her pussy within her hands. Her other hand reached back to unclasp her bra, allowing her breasts to now hang freely.

Clarissa massaged her breast with one hand and found her clit with the other. She felt her pussy, warm and moist. She felt a slight moan exit her lips as she continued to touch herself.

She lifted her bra upwards to expose a pair of young and firm breasts that were still growing. Her nipples stood out from her breasts, and were sensitive to her touch. She circled them with her fingers, from one breast to another, just like drawing an infinity sign. And in that moment, she truly felt infinite.

Her other hand toyed with her pussy, drawing a finger down across her wet slit. Her panty was in the way of her movements, so she pulled on the waistband and let it fall to her ankles, exposing her most private regions.

She watched Mr Lim move his hand over his groin to cover up his unmistakeable bulge slowly forming in his pants. While staring at it, Clarissa started to play with her pussy, circling her sensitive clit with her index. She imagined what it would be like to feel his cock up against her.

Clarissa started to walk closer to Mr Lim, allowing her lust to take over, letting her teacher see her developing body. A tingle went through her as Mr Lim made the first contact, placing his hands on her thigh.

She placed her hands on his chest, feeling the strong, well-built body of a man much much older than what she was used to. Clarissa leaned in, feeling his quickening breathing on her naked breasts.

Her hand travelled downwards and underneath his hands, feeling the hard bulge through his pants. It felt large, almost unreal.

Mr Lim's hand stroked her thigh, feeling her soft skin under his hands. Clarissa took her hand, wet with her arousal and directed Mr Lim's hand to her mound. She moaned as she felt his hands upon her sensitive spot, his hands cupping over her pussy, as if to collect the juice that was so rapidly leaking out.

She unzipped his pants and felt his cock over his underwear, warm and pulsing with each heartbeat. She leaned her breasts into his face and felt his erection stiffen, as if it was not hard enough already.

Clarissa felt his fingers start to move, sliding along het wet snatch, feeling the between the folds of her skin, spreading her fluids across her slit.

She reached underneath his waistband and pulled it down, revealing a large adult cock, one of a size that she was not used to seeing. She marvelled at the veins around the shaft, the reddish head that was pulsing with arousal. The scent of precum also filled the air, salty and sexy.

Just as she imagined it, she spread her legs on both sides of the chair that Mr Lim was sitting on, slowly lowering herself to feel his cock right against her pussy. She groaned as she felt his hand give way to let her pussy feel the contact of his member, the thick meat sliding between her legs, just on the outside of her vagina.

Her breasts were up against Mr Lim's face now, and she felt the stubble of his chin rubbing against her cleavage, a sign that she was dealing with a real man, not one of those boys that she made out with. The hairs on her neck stood up at the pleasure of his mouth slowly sucking on her skin.

Involuntarily, Clarissa felt her hips start to grind against his cock, the thick meat sliding up and down against her pussy, assistes by her natural lubrication, probbably leaking down onto Mr Lim's cock, mixing his precum and her wetness.

As Mr Lim took her nipple into her mouth, Clarissa jerked forward with the sudden spike in pleasure, her veins running with liquid pleasure. With that jerk, she felt his cock slide into position over her widening vagina, which was gladly inviting him into her velvetly embrace.

She felt the head pop in bit by bit, feeling the familar stretch of her flesh as she accomodated him. Yet it all felt as if she was a virgin all over again, his thick cock straining against the tightness of her pussy, one which was more used to the cocks of boys who were still undergoing puberty.

Clarissa felt full before the head of his cock was even fully in, and she was surprised she could feel even fuller, even more satisfied. Mr Lim did not hurry, as if somehow he knew how tight a pussy of a teenage girl would feel like with an adult cock for the first time.

Clarissa felt a pop as his cock sunk into her, and the rest of the shaft slowly followed, the folds of her pussy slowly sliding over the veins of his member.

With each centimetre of flesh that slid into her, she felt more and more satisfied, feeling Mr Lim's cock reach into her further than anything ever could. It was like an itch that she could not scratch by herself.

She groaned as she finally felt herself sit down fully onto his cock, her butt on top of his balls.

Clarissa slowly eased herself to and fro, feeling the large pulsing member stroke the walls of the warm cavern between her legs. Clarissa slid herself up and down as she has practiced before, feeling again and again the cock hitting into her deepest regions.

She moaned and groaned, building herself up to an oragsm. For once, she felt her legs weaken and tingles along her inner thighs, pleasant and ticklish. Mr Lim full cock plunged into her, each thrust emitting the audible slapping sound of sex.

As she feel herself reach an orgasm, her pussy clenching itself over Mr Lim's cock, squeezing tight on it. She feel his cock tense up as well, as Mr Lim started to ejaculate into her. The warm semen started to hit her inside, mixing with her fluids.

Clarissa groaned as the waves of pleasure rushed over her, as her mind almost went blank from the sheer release. She leaned into Mr Lim, holding his head to her breasts for support, as she felt her legs give way to her weight.

As she feel her breaths coming back to her, she basked in the afterglow of the orgasm, feeling Mr Lim's cock throb inside her, the last drops of cum spilling into her, inside her very fertile womb.