Madison the Intern
Introduction:
Madison thought her summer internship at the law firm was going to be a “free ride”. She should have checked the fine-print.
‘Hey Maddie, you’re late,” Sheila observed, looking up from her stack of paperwork. “She’s already called to ask about you.” I glanced at the glow of the digital clock on her receptionist desk. 8:02, it displayed in nonnegotiable terms — two unforgivable minutes overdue. I gave her a pleading gaze with my large brown eyes, knowing in my heart that she was powerless to help.
“She’s in a state this morning,” Sheila warned sympathetically. “The new girl from Accounting has been in there for almost an hour, and it sounds like she’s getting torn a new one.”
As if to punctuate the point, the heavy oak door to the inner office of the CEO was pulled open and a petite, redheaded girl rushed out, looking disheveled. Head down, unable to meet our eyes, she sniffed and wiped a tear from her cheek as she hurried by, leaving a black streak of eye liner across her cheek. High heels clacked a receding rhythm on the tile floor as she rapidly made her way to the glass door of the receptionist office. A sob escaped her lips as she fled into the hallway. The pneumatic closer hissed, drawing the door shut once more.
“Your turn,” Sheila offered quietly, gesturing with her hand towards the open office door of the proverbial lion’s den. I nervously swallowed and then attempted to paste a strained smile onto my expression as I approached the office of the CEO.
Ms. Booker, CEO, brushed her shoulder-length black hair back over one ear as she shot a subtle look at the large clock on the wall as I entered. It was all the chastisement that was needed as the minute hand crept its way towards the three-minutes-after-the-hour mark. I padded my way across the plush Oriental rug, choking back the urge to offer an apology for my delay, knowing it would only further inflame the issue.
The happily-divorced woman executive simply didn’t have the patience for delays. In her mid-thirties, she was young for the position of CEO in a large legal firm. But she ran her business with the same driving zeal as the rest of her life, dividing her waking hours between long days at the office, hard workouts at the gym, and the remaining fragments of the day spent with her two daughters.
I set the coffee and bagel down on the desk, careful to avoid a spill. “They were out of strawberry cream cheese, so I had to get you raspberry,” I explained. Ms. Booker favored the bagel with a disapproving look, but said nothing. She lifted the coffee cup and took an experimental sip of her morning brew. Her lips pursed into a sour expression as she set the cup back down with a hint of irritation. “Remind me, Madison, how do I take my coffee?” she inquired in a conversational tone.
My heart sank, realizing I had forgotten to add the required amount of sugar. “Sweet as a cheerleader, and twice as creamy,” I recited her desired formula from memory in a hushed voice. Ms. Booker fixed me with a piercing look and then retrieved a pair of sugar packets from her desk. As she made the necessary correction to her cup of java, my eyes were drawn to a familiar looking document on her desk. It was my first draft of the legal analysis of the Carson merger. The work was a tall order for a first-year intern like myself, and apparently my efforts had failed to measure up. The top sheet was a bloodbath of red ink, promising additional carnage on the following pages. I found myself wishing I could do a complete restart of the morning.
Ms. Booker slid the report across the desk to me with a light push. “I’ll need that revised by the end of the day,” she instructed.
I nodded and then looked down at the floor submissively. “Yes, Mother,” I responded. A shock jolted through me, instantly catching the vital breach of protocol. She slowly looked up at me with an ominous expression. Making reference to our family relationship while in the office was an offense of the highest order. As a summer intern in my mother’s law firm, I was afforded no special considerations due to our family ties. If anything, Mother tended to set the bar of approval several notches higher for me than the already demanding performance levels required of the rest of the staff.
I trembled, feeling a heavy fog of silent tension hanging in the air as she stood up from her desk and crossed the office. The woman moved with the graceful ease of a cougar on the prowl, hips rolling sensuously in her tight black business pants. A subtle creak of hinges told me she was closing the wooden office door. The gentle metallic click of its latch into the frame causing me to flinch as if a steel-barred door of a jail cell had just slammed shut behind me. Her footsteps treaded lightly back across the carpet as she approached me from behind. I stood stock still, facing her desk, unwilling to turn and embrace her wrath.
“You know, Madison,” she said quietly as I felt her hands find their way lightly to my waist, “I think sometimes you purposely try to vex me. Do you? Does it excite you? Did you come here this morning wanting to be taught a lesson?”
“No, Mother… I mean, Ms. Booker… I… I would never…” I stammered in denial, feeling a nervous tremor shudder through me. A shiver raced up my spine as the tell-tale sound of a zipper could be heard. The back of my skirt split apart as the plastic teeth of the garment’s fastener disengaged from top to bottom. Fully opened, my pleated grey skirt fell away from my hips, slithering down my shapely thighs in a silky cascade to puddle around my feet.
Despite my denial, the sopping wet crotch of my tight pink panties revealed the truth — ‘Exhibit A’ in legal parlance. Mother’s fingers travelled up my inner thighs, finding the tell-tale abundance of vaginal wetness soaking through the sheer mesh of the lace. Her fingers withdrew, her hand reaching over my shoulder to bring the slimy digits into view. She rubbed her glistening fingers together, demonstrating their liberal coating of my girlish lubrication. I blushed, caught in my obvious lie.
She issued a quiet chuckle under her breath. My pulse quickened as I braced myself to hear the command I knew was coming. “Panties down, please, Madison,” she instructed. My flush of shame flared to a more intense shade of crimson, the air-conditioned office suddenly feeling uncomfortably warm. Her tone was calm, but I immediately complied without question, years of discipline causing an instinctive reaction to obey. I dragged the waistband of my underwear downward, peeling the wet panty crotch away from my steamy wet pussy as long strands of vaginal juices pulled taunt and glistened in the florescent lighting. I slid the panties to my knees, leaving them suspended between my naked legs. The scent of my moist pussy wafted around me as more undeniable evidence of my arousal. The fleshy, ruffled lips of my twat — throbbing with anticipation — unfurled further, blooming open like a rose. My heart hammered in my chest, my breathing rapid.
Her hands found their way once more to my now naked hips. Goosebumps rose on my bare skin as the tips of her fingers trailed downward, lightly raking her red, manicured nails over the rounded cheeks of my firm little ass. Her digits slid intimately into the crack of my butt, secure in the knowledge that this was territory she claimed as her own. “Oh, you chose pink today,” Mother observed casually. “How cute! It matches your panties.”
I breathed a sigh of relief, happy to have finally done something right. Mother always appreciated a well-coordinated outfit, so I made it a point to color-match my panties with my choice of butt-plug. Some sort of anal insertion was part of the mandatory dress code for all the girls at the legal firm, and Mother took a strong personal interest in the inspection process to assure compliance. Some days I found myself in the mood for a string of anal beads, but on a whim this morning, I had gone with the tastefully petite plug, adorned with a glittering faux jewel on the end. My mother’s fingers closed around the exposed end of the small anal probe, gently giving it an experimental tug. My little rectal rosebud was snugged down firmly, flexing backwards but refusing to yield its prize to such a delicate pull.
“Ummm, that… is… tight,” Mother complimented. I brushed my long blonde hair back over one ear in a flirty motion, allowing a shy smile to creep into view. Applying a more insistent force, she firmly grasped the end of the pink little butt-plug and succeeded in freeing it from my anal embrace. I stifled a small gasp of pleasure as it popped loose with a barely audible sound. The taunt little ring of my sphincter puckered back and forth and then sealed itself up securely. She set the butt-plug on the desk next to her neglected raspberry cream cheese bagel and then turned to walk across the room.
A brief sound of rummaging was heard and then the crush of soft carpet fibers under Mother’s heels revealed her return from behind. I cringed, reacting to the all-too-familiar plastic ‘pop’ of a plastic lid off a small container. The pungent smell of mint washed over me, causing my nostrils to flare. “Please, no… not that…” I begged, knowing she was already dipping two fingers into the jar of Vicks Vapo-Rub.
“Hush,” she responded in a tone that invited no further argument. With a firm hand on my upper back, she directed me into place. The sound of my rapidly-increasing pulse throbbing in my ears, I complied, leaning forward across her desk and spreading my legs as wide as the straining panties around my knees would allow. I wobbled unsteadily on my high heels, wishing I could kick them off. But Mother would never have allowed that, liking the way they accentuated the posture and firm curve of a young girl’s ass.
I choked back a mewl of protest, biting my lower lip as Mother’s fingers made intimate contact with my pussy. Already I could feel the initial effects of the Vicks — a cooling sensation on the delicate tissues of my cunt. I quivered, knowing from experience that would quickly transform to a blazing heat as the formula set to work on the hyper-sensitive nerve endings. I squirmed as she dug deep, burying two gel-coated fingers to the hilt in my twat, twisting and rubbing to ensure a uniform spread of the diabolical lotion. I hissed a sharp intake of breath as the chemical reaction began. A seething heat began to surge to a boil in the interior of my snatch. I clenched the cheeks of my ass as I felt her fingers withdraw from the velvety sleeve of my pussy. Not allowed to touch myself without Mother’s permission, I desperately wriggled my hips in a futile effort to react to the stimulation of my vaginal tissues.
My efforts were rewarded by a sharp crack of flesh on flesh as my mother’s open hand lashed out and landed a sharp blow on the naked cheek of my rump. Firm, bare skin quivered with the impact. I shrieked, a combination of surprise and actual pain. I bounced on my toes, daring to reach behind me in an attempt to rub away the lingering stinging sensation of the slap. Mother’s fingers closed around my hand, pulling it away.
A red blush of shame once again crept up my face, matching the crimson shade that now surely glowed in the outline of her hand on the creamy flesh of my taunt little rear. It was a well-established fact amongst the staff that the CEO’s office walls offered precious little privacy in the way of sound-proofing. The deeds carried out in that inner sanctum were quite routinely the topic of speculation as unusual noises filtered their way out into the adjoining hallway and legal library. I knew that any cries — be they born of complaint or enthusiasm — would be fast-spread through the efficient office rumor mill.
“You are such a squirmy little thing,” Mother observed, stepping around her desk and punching a button on her office phone. Taking advantage of the distraction, I dared to stand, reaching down and pulling my panties back up into place, hoping that my morning ordeal had come to a quick and merciful end.
The response on the phone was prompt, as expected. “Yes Ma’am?” the receptionist’s voice answered professionally over the speaker.
“Sheila, what is my first appointment this morning?”
The girl knew to have the information at her fingertips. “Nine o’clock, Ma’am, with the Denton group, in our downstairs conference room.”
“Thank you, Sheila,” Mother replied, disconnecting the call.
I turned my head, seeking out the clock on the wall. 8:15. I shuddered. Forty-five minutes of Mother’s undivided attention held almost unlimited potential for abuse and humiliation. I prayed that she might have some other pressing matters to attend to.
Mother caught my sideways glance as she approached. “Oh, don’t you worry, Madison,” she assured me. “I’m sure we’ll have plenty of time to get you sorted out before my meeting. Defeated, I resumed my position bent over her desk, grasping at the edges of the wooden top with both hands with a secure grip.
Mother once again picked up the jar of Vicks rub, scooping out another liberal glob with a pair of elegant fingers. The earlier application of the balm into the depths of my pussy was just beginning to come into its own, every nerve receptor in my juicy little twat throbbing like a live electrical wire. Mother gave a ‘tsk’ of disapproval, finding my panties pulled back up. “Madison, you continue to test me,” Mother warned. Another firm swat landed on my rear, a reward for my impertinence. This was followed by another, even more intense. I squealed in protest as my panty-clad rump jiggled in response to the punishment. I felt my pussy twitch, the Vicks continuing to work its heating magic.
With her free hand, Mother tugged my panties aside, exposing the crack of my ass to her intense scrutiny. I squirmed self-consciously, feeling the invasive nature of her stare into my most private parts as surely as any actual physical touch. My worst fears were realized as Mother’s free hand tugged at the firm cheeks of my ass, spreading my crack open. The tips of her other fingers — thick with the gelatinous coating of Vicks — zeroed in on the tightly clenched little pucker of my butthole. I flinched, feeling the incestuous touch of my mother’s digits on the soft, crinkled flesh of my rear portal. The initial cooling effect of the Vicks took hold, causing me to rise up on my toes in a futile attempt to escape the chilling sensation.
Mother paused. I could sense her patience wearing thin. I obediently settled back into position and spread my legs into a wider stance in an effort to appease her. Stimulated by the chemical reaction of the lotion — as well as my Mother’s gently probing fingertips — I felt the snug little pucker of my rectum begin to tremble. Mother’s hands tugged more insistently at my butt cheek, spreading me further. The tight ring of my anus responded, pulsing in and out in a series of muscular contractions. She took this as an open invitation, applying steadily increasing pressure. My head came up off the top of the desk with a gasp. Two stiffened fingers plunged their way into the steamy tunnel of my ass, stuffing a generous glob of Vicks in hard and deep. I hissed through my teeth, feeling the cooling action spread as Mother worked her fingers, twisting and thrusting, sheathing her twin digits full-depth in the clutching embrace of my tight little shitter.
The Vicks took hold, igniting an inferno of sensation in the incredibly tender tissues of my bowels. I howled — heedless of how the sound might carry beyond her office — clenching my ass cheeks and raising up on my toes in a uselessly desperate bid to escape the blistering sensation. Mother’s fingers slipped from my ass, leaving the little rear portal puckering frantically open and closed in a rapid series of spasms. She delicately pulled my panties back into place, giving me a soft pat on the rump as she stepped away. I whimpered, squirming as the over-stimulated nerves in both my cunt and asshole throbbed in response to the chemically fueled surges of heat. I bit my lower lip, only partially managing to choke back yet another cry. I desperately wanted the sensation to end, and yet a more primitive part of my mind rebelled, savoring the incredible sense of stimulation. But regardless of my wishes, I knew from experience that the blazing, sensual itch of the Vicks formula in my two little love tunnels was only just beginning, and could take up to an hour to fully run its course. I glanced once more at the clock. 8:17 — a scant two minutes since the last time I had checked.
Mother returned, having retrieved a familiar box from the closet in her office. She pulled back the lid, proudly displaying the contents. I saw that several new additions had been made to her collection since my last private session in her office. “You pick, Madison,” Mother offered, displaying an uncharacteristically generous state of mind.
I flashed to a mental image of a felon being allowed to personally pick the gun to be used for his own execution. With a trembling hand I reached out, fingers venturing into the box and grasping a smooth purple dildo, perhaps an inch in diameter and about five inches in length. I held up my choice with hope in my eyes. Mother laughed and I felt my misplaced optimism melt away like a spill of ice cream on a hot summer sidewalk. “Oh, Madison,” she chided with a light lilt in her voice, “how are you ever going to grow if you refuse to challenge yourself?”
She took the small purple dildo from my grasp, dropping it back in the box with a mild look of distain. She rummaged, and then proudly pulled out her choice for a replacement — a new addition to her extensive fleet. I groaned, my eyes going wide in distress as I viewed Mother’s idea of a ‘challenge’. It was a monstrous dildo, crafted of a shiny black rubber. Fourteen inches in length, it sported a huge penis-shaped head, two inches in diameter. Below that, the shaft of the cock tapered, dropping to a merciful inch or so in thickness. But that reprieve was short-lived as the size then once again began to enlarge. A series of ringed ridges, ever increasing in diameter, built their way towards the base. At its most extreme, the far end of the rubbery prick measured an alarming three inches across. A series of small bumps and soft rubbery bristles studded the length of the shaft, presumably emblazoned on the original packaging as being “for her pleasure.” I found myself doubting the truth in advertising.
“Yes, I think this will do nicely,” Mother pronounced with a satisfied tone. My vote in the matter had apparently fallen short of the ballot box. She set the cardboard container on the floor and placed the massive rubber cock down on the desk with a heavy thump, a few inches in front of my face. She stepped away, leaving the dildo and I an opportunity to get visually acquainted.
Mother’s fingers announced their presence on my hips, sneaking their way down into the elastic hem of my panties. My hips wriggled, the burning sensation of the Vicks now fully ignited on the suffering nerves within my quivering cunt and asshole. The muscles in my naked inner thighs twitched. She tugged downward on the tight little undies, peeling them off my hips and down my legs. “Step, please,” she requested as she knelt behind me. I did as requested, shifting my weight from one foot to the other and lifting my feet as she fully removed the pink, lacy undergarment. I spread my legs into a wide, accommodating stance, knowing better than to make her ask.
“Madison, my dear, you are a sloppy sight this morning,” Mother chastised. I craned my neck, turning to look back at her from my vulnerable position across her desk. Standing, she held my panties up to the light for inspection, spanning the lacy crotch open across her fingertips. Numerous pearly smears of my female wetness glistened, soaked in liberal quantity into the delicate fabric. A single shimmering droplet of my sweet girlish syrup trailed downward, swaying gently on a suspended strand before breaking off and dripping down to soak into the carpet at her feet. I wondered how many of the other office girls had offered up a similar deposit. It was clear why Mother insisted on a frequent schedule for the steam-cleaning of the expensive rug.
She brought the panties to her face, closing her eyes as she inhaled deeply. Extending her tongue, Mother gave a tentative lick into the panty crotch, seeming to find the syrupy feminine discharge to her liking. Then she applied her other hand, weaving her fingers into the panties, interlacing them around her digits to wrap her entire hand with the slippery material. She flexed her fingers, opening and closing them into a fist. Then she favored me with a charming smile. I groaned and shut my eyes, not even wanting to know what she had in mind.
Never let it be said that my mother lacked for any shortage of creative thought. She took a step closer to me from behind. Her free hand pressed down on my lower back. I submissively complied, arching my spine downward to roll my hips into a more upward orientation. My firm little rump jutted out, my moist, glistening pussy proudly on display between my open thighs. I found myself wishing that I could remove my blouse, thinking perhaps that being entirely naked might provide a more intimate ambiance. Half-clothed as I was, I couldn’t help but feel like an exposed cunt, a toy for my Mother’s amusement.
Her hand trailed slowly up my naked inner thighs, the lacy wrapping of my panties around her digits adding a delicate sensation of friction. Her fingers slid easily higher, lubricated by the steady trickle of vaginal goo that glistened on my tan, well-toned legs. Exploring digits — wrapped in lace — found my pussy, open and eager. Two fingers pressed inside, a wet squelch sounding as I took her with a grunt of animalistic pleasure. Slowly she twisted, buried to the third knuckle. Despite myself, my hips rolled gently, rocking in time with her rhythmic motion.
Her fingers withdrew. I whimpered with longing. The fingers returned — three this time — forcing their way into the sweltering depths of my twat. I clenched my teeth, feeling the strain as my Mother’s fingers stretched me. “There’s my tight little girl,” Mother cooed as I moaned.
“Do you want more, Madison?” my mother breathed, her voice taking on a slightly ragged edge. I couldn’t even understand how she could ask. My pussy was straining at its very limits, clenched down tight in a trembling grip around her three embedded digits. Panting in a state of growing distress, I knew that anything more than this would be an absolute impossibility. I nodded, squirming my hips and begging her for more.
Three fingers slipped from my cunt, the panty-wrapped digits dragging a deluge of creamy cunt butter with them in retreat. Her fingers returned, pressed together into a group, twisting back and forth as slow, inevitable progress was made on their insertion. I cried out, my breath coming in quick, desperate heaves as I felt the gateway to my vaginal slit spasm in protest at the incredible stretching sensation. Mother paused, slowly twisting. I gathered my courage and then nodded, ready to continue.
Mother’s other hand reached up, her fingers intertwining themselves gently with the long curls of my blonde hair. She pulled back, causing me to shriek in protest as she used her grip for extra leverage. I rose up on my toes, muscles in my thighs and ass clenching tightly in subconscious response. A prolonged squeal escaped my lips as stars exploded across my vision. An incredible straining sensation flared through the lips of my cunt, enhanced to an exquisite level of pain by the over-stimulated nerves enraged by the burning formula of Vicks. Suddenly there was a feeling of being cunt-punched, followed by an amazing sensation of satisfying fullness. I panted like a bitch in heat.
My mother paused, granting me a moment to stretch and adjust to the cunt-stuffing sensation. Slowly she pulled back and I felt the straining lips of my cute little twat distend outward. Then my pussy bulged, clenching down tight. I gasped. “Did… did you?” I stammered.
Mother replied with a girlish giggle of delight. “That’s right, Madison, that’s my entire fist you’re feeling.” My mind reeled in a dizzying spin. This was uncharted territory, even for my mother’s wicked imagination. Gently she twisted her arm, wrenching her panty-wrapped fist in a heavenly rotation inside my steamy twat. Then she eased herself deeper, pressing past her wrist and forcing the lips of my cunt into an obscenely stretched oval, clutching desperately at the middle of her forearm. She pulled back, a wet sucking sound filling the room as I sobbed with ecstasy. Sticky twat syrup drained in slithery rivulets down my inner thighs. She forced herself back in, deeper still, ignoring my blubbering protests that I was stuffed beyond my limit. She flexed her fingers, up in the far reaches of my fleshy vaginal folds, before closing back down into a fist and pulling back on a lengthy outstroke. The incredible sensation of burning friction in my over-stimulated snatch was nearly overwhelming. My fingers clawed at the top of her desk, skittering in mindless patterns across the polished wood. A whimper escaped me.
The retreating bulge of her hand reached the quivering embrace of my aching twat lips, causing them to flare outward as they strained to retain their grasp on Mother’s incestuous, cunt-fucking fist. I cried out, begging her to relent, but she showed no mercy. I grunted, wondering if giving birth might have a similar feeling to my mother forcibly withdrawing her clenched fist completely from my cunt. I had but scant seconds to ponder the comparison though, before she reversed her motion, thrusting her hand back into the quivering cavern of my twat and sinking herself just short of elbow deep in her daughter’s vaginal embrace. I gasped, feeling my hips begin to swivel in response. She rotated her fist, left then right, a circular grinding motion that caused an irresistible shudder to arise from deep within the far depths of my inflamed little pussy.
She pulled back and fully out, ample lubrication from my twat now glistening along the length of her arm. My vaginal lips gaped, opening easier this time as they flared to allow the passage of her fist. My pussy was an open grotto, a fleshy cavern in desperate need of filling. Mother rewarded me with a hard thrust, driving her fist in deep. My hips bucked, meeting her halfway. I felt the crook of her arm snug up tight in the crack of my ass as she buried her sensuous fist elbow-deep in my twat. The mental image sent me over the edge. I howled with lust, the fleshy folds of my profanely overstretched twat exploding into a spasm. I shrieked, mindlessly cycling my hips in a frenzy of motion, fucking myself onto my mother’s arm. The orgasmic convulsions in my snatch reached a fevered pitch and I flailed out of control. Only my mother’s fist securely embedded in my frantically clutching cunt kept me from slipping off the desk and onto the floor in a quivering heap of wrung out pleasure. Mother twisted her wrist, back and forth in a seemingly tireless motion, launching me into second orgasmic fit just as the first was beginning to fade. My sides heaving in desperation I moaned like a whore and felt a violent tremor shiver through my entire body, spreading from the core of my cunt and spreading to all extremities until even my vision began to fade to grey.
After a few moments I regained my senses, hearing only the sound of my desperate panting for breath. I felt a vague stretching sensation, realizing that it was my mother’s loving fist slipping from the cavernous fuck slot of my cunt. “Oops,” she intoned. I slowly turned my head, gazing back at her with glazed, unfocused eyes. She wore a curious expression, glancing from her bare hand, to my loins, and then back at her hand. “I think I may have lost your panties in there somewhere,” she admitted. I moaned as she slipped her hand back inside me, carefully prospecting the depths of my wrecked vaginal fuck cannel for the mysteriously missing undies. Suddenly her thoughtful expression brightened with a look of victory and she withdrew, displaying the elusive lacy pink delicates, dripping wet and limp like a sopping wash rag. I sighed with relief as a post-orgasmic shudder trembled through me, glad that I didn’t have to go digging after them myself. As Mother deposited the dripping wad of twat-soaked panties on the desk, I sank slowly to the carpet, a fit of giggles overcoming me as I curled myself into a fetal position.
Mother wasn’t having any of this self-indulgent nonsense however. “On your feet,” she commanded, her tone betraying irritation that she should even have to tell me. On unsteady legs I stood, resuming my position bent across her desk. She walked across the office, inspecting a nearby bookcase, scanning the shelves for a particular item of interest. “No…” I moaned, knowing full-well what instrument of evil dwelled in a sacred place between her reference books on law. She turned with a smile, issuing a sharp crack of leather against her lower thigh. “Please… I’m sorry. I’ll do anything…” I begged with a sob, my lower lip quivering at the sight of her dreaded riding crop.
She was unmoved by my desperate pleas for mercy. We both knew that I had purposely defied her, testing my boundaries with several minor acts of blatant carelessness or outright rebellion. I shuddered, knowing my fate was sealed. Biting my lower lip, I once again leaned forward across the desk, knowing what was expected. I reached back with both hands, grasping the firm twin cheeks of my naked ass and reluctantly spreading them wide as she approached. Mother purred with approval, moving into position. “Good girl, Madison,” she praised. A choked-back sob escaped my lips, a mixture of fear and anticipation, as I shifted my high heels on the carpet, spreading my legs into a wider stance.
The first blow was but a tease, landing with a light slap on the left cheek of my ass. I flinched, but with only the slightest little whimper. The leather tip of the crop tapped a series of slow, light touches on my naked skin, as if both it and my Mother were pondering their next move. I twitched in response to each of the gentle contacts, anticipation building to an unbearable level of tension. An emotional sob issued from my lips as tears of expectation began to well up in my eyes.
The second lash struck, hard and true, her skillful hand expertly landing the supple leather tip of the riding crop with a wet splat directly on the hyper-sensitive flesh of my puckered little anus. I shrieked a yowl of anguish that surely echoed throughout every hall and office in the building. Fireworks exploded across my vision at the staggering sensation of pain. “Oh my god!” I gasped, blubbering in the brief respite that followed, feeling myself desperately short of breath. I could sense the blazing red welt of tormented flesh rise, throbbing angrily, stopped just short of drawing actual blood. Another aborted sob of dismay escaped my lips, but I dutifully I wriggled my naked hips, gaining a firm grip on the cheeks of my rump and spreading myself wider, as I knew I must.
“Spread your pussy for me, Madison,” Mother requested. Tears trailed down my cheeks. I sniffed with self-pity and then dutifully lowered my fingers into position on either side of my pulsating vaginal mound. Pressing my fingers into the soft pale flesh surrounding my cunt, I eased myself open, trembling as I felt my tender little twat gape. The riding crop announced its motion with a soft whistle, cutting wickedly through the air before savagely biting the leather tip into the exposed interior tissues of my snatch. A mist of wet spray erupted, my dewy female juices splattering in a rain of small droplets from under the stinging impact. Another lash quickly followed, choking back my scream into a strangled gurgle of mind-numbing pain. I squirmed, pulling my pussy open wider, rolling my hips upward to present myself in a more favorable position.
A well aimed whipping motion of Mother’s wrist slashed the riding crop down hard, unyielding leather finding purchase on the delicate and inflamed tissues of my clit. Agony and ecstasy swirled in a raging vortex as my prolonged wail seemed to rattle the artistic decorations on the walls. My clit swelled, throbbing in excruciating pain. I bucked my hips, once, twice, waiting for that next lash to strike. A tremor shuddered through the farthest reaches of my pussy, just the initial glowing embers of a potential orgasm.
Mother paused, surely wearing a bemused expression on her face at my shameless antics. Gasping for breath, I blubbered, a trail of drool trailing downward from my slack and open lips. As the delay extended, I collapsed on the desk, relieved that Mother’s need for corporal discipline appeared to have run its course.
The leather crop cut through the air again, favoring my tender little anus with another blossoming welt. I shrieked, the tender ring of my rectum puckering open and closed in rapid spasms as the flesh tingled in anguish. I groaned, my fingers sliding instinctively upward from my pussy to spread the cheeks of my ass open in wider invitation. Another twitch of woven leather whip rewarded me with yet another emerging welt, precision placed just inside the gaping rim of my wrinkled anal orifice. I hissed a sharp intake of air through clenched teeth, feeling a shiver race up my spine. I squirmed eagerly, the muscles in my inner thighs rippling with anticipation as the staggering pain transformed itself into the pent up energy of a still restrained orgasm. Just one more lash would do it… Mother still held back, letting the anticipation build to a nervous tension. I purred with appreciation at her sense of theater and timing, holding my ass cheeks open wide.
But after a prolonged and apprehensive moment, the next stroke of the riding crop still failed to deliver. Confused, anxious, I dared to lift my head and turn my gaze behind me to investigate. I whimpered, feeling the brink of my promising orgasm begin to falter. With wide eyes I looked back at Mother, pleading silently for satisfaction.
But she had discarded the riding crop and was occupied with strapping herself into a familiar looking harness. Wide black nylon straps cinched tightly around her toned upper thighs, blending almost seamlessly over her dark business pants. A stout buckle secured another strap around her waist, completing the ensemble. A flexible rubber pad covered her crotch, sporting a sturdy plastic prong shaped in a series of barbs. I smiled, knowing that plastic shaft mated to a matching hole in the back of each of my mother’s myriad of dildos, offering complete interchangeability on a whim. With a whimper of anticipation I reached with fumbling fingers to eagerly grasp the huge black dildo from the desk top. Wordlessly I handed the monstrous prick back behind me, allowing it to slip from my grasp as Mother took possession. A subtle squeaking sound betrayed the plastic prong of the harness being securely fitted into the back of the rubbery prick, locking the two firmly together.
Mother approached the desk, the massive rubber prick bobbing horizontally from her loins, in a slow, steady rhythm, ominously thick and heavy. My breathing came in short, eager gasps, waiting for that first touch of intimate contact. My eyes went wide, seeing my mother once again reach for the dreaded jar of Vicks and retrieve an oozing glob of the wicked substance on her fingers. She liberally coated the entire shaft of the ponderous rubber prick, adding yet another generous dollop when the initial application spread a bit too thin.
Then — the gigantic black dildo glistening with a thick coating of the gel — she stepped into place behind me. I had no preconceived notions of her intended target, but had to admit to a trembling shudder of lustful eagerness as I felt the huge slippery cock knob fit itself perfectly into the cute little dimple of my butthole. Mother fisted the shaft of the cock, steadily increasing the pressure. I gripped the sides of the wooden desktop with both hands, my knuckles turning white with the strain.
Mother pushed and I gritted my teeth, feeling my tight little anus offer valiant resistance. Again I dared to indulge in a minor bit of rebellious behavior, clenching my muscular little sphincter down tight, resisting her insertion. The rubbery dildo bent in the middle, straining. Her hips bucked forward as the shimmering round tip slipped free of the dimple of my ass, riding up the cleft of my rump cheeks and onto my lower back. I savored the minor victory, knowing Mother did not care for being thwarted. She stepped back into position behind me, pressing one hand down on my lower back as she fisted the massive cock with the other. I knew there would be no escape this time. She maneuvered the rounded nose of the prick once more against the sweet little pucker of my anus.
I clenched again, but this time Mother was wise to my antics. She thrust hard, lunging forward with her hips. I squealed, feeling my tightly clenched anal ring forcibly pried open by the rapidly flaring girth of the huge cock knob. It would have gone much easier on me had I simply been compliant. Tears trailed down my cheeks as my tortured little anus yielded to the irresistible force. I took her with a grunt, feeling the widest part of the rubbery cock head plow past my quivering anal ring and seat itself firmly in my ass. My puckered little rectal rosebud quivered and then sealed itself down in a loving embrace, hugging the narrowed portion of the cock shaft just below the flare of the tip.
I squeezed down with the muscles in my bowels, instinctively trying to expel the invasive head of the rubbery prick. My snug little anus flared, appearing to make progress as Mother was distracted, adjusting her stance. Then, with a lunge of her hips, several inches of the black, Vicks-coated shaft were thrust hard into my ass. I howled in protest, trying to squirm away from her. Mother forcibly pressed down on my lower back, pinning me to the desk. I whimpered in submission, feeling my hips roll sensuously of their own volition.
Mother stroked back as I clenched my jaw, feeling the intense burning friction erupt inside my ass. My taunt little ass ring strained as the rubbery cock knob threatened to withdraw. A powerful lunge of her hips hammered nearly half the length of the monstrous cock back into my ass. I wailed in protest, feeling my bowels stretched to the limits as the flaring girth of the prick made its true dimensions known. “Please… no more,” I begged. Mother laughed, drawing back again in preparation for another ass-plundering stroke. Her muscles tensed, the vibrations transmitted down the length of the rubber shaft to transmit though the bulbous tip of the cock still lodged inside my butt.
A prolonged squeal burst from my lips as Mother gave a powerful lunge. The rubbery knob of her strap-on prick plowed into new territory in the depths of my colon as my tight little rectal portal stretched obscenely around the ever-increasing taper of the cock shaft. Panting with desperation, I knew for certain that I had taken every last inch of the massive cock, and that the worst was surely over. Mother stroked back and then surged forward, proving me wrong as several additional inches of her thundering dildo bored into previously virgin depths of my bowels. The ring of my sphincter puckered in a frantic spasm, desperate to somehow escape the impossible stretching it was experiencing.
I felt the massive cock pull back, breathing a shuddering sigh of relief as the incredible girth diminished along its retreating length. Both of Mother’s hands grasped firmly onto my hips and I whimpered in anticipation. The breath was knocked from my lungs as Mother thrust, powerful gym-toned muscles in her body working in conjunction to once more spike the rubber cock deep into the steamy depths of my quivering rectal fuck tunnel. I felt her weight on top of me, resting on my back as she panted in the aftermath of her effort. I felt the tickle of the fabric of her business pants in the crack of my ass and I knew that she was finally fully hilted. I moaned, lovingly grinding my rump against her loins, feeling the rounded cheeks of my naked ass pressed flat against her. The timing of my ragged breathing matched to hers, our bodies synchronizing, seeming to merge into a single ass-fucking creature.
I jerked in shock as the phone on the desk suddenly buzzed, a red light on its panel beginning to blink in a slow, steady rhythm. Mother looked up. “Could you get that for me, Madison?” she requested calmly. With clumsy fingers I clutched my way across the desktop, nervously knocking her cream cheese bagel to the floor as the phone buzzed insistently for the second time. My fingers fumbled across the number pad, finally finding and stabbing awkwardly once, and then again, at the blinking red button. “Yes, Sheila?” Mother inquired as my fingertip finally completed this complicated feat of manual dexterity.
“Your nine o’clock is here,” Sheila reported over the speaker in a courteous voice. The girl was a wonder of professional decorum. I knew without a doubt that every painful shriek and howl of lust from my lips had found its way into her reception area. Her tone of voice indicated not a hint of anything amiss.
“Ah, yes, of course. Thank you,” Mother replied. Please inform them that I’ll meet them down in the conference room in a few minutes.”
“Yes Ma’am,” her receptionist replied.
“Oh and Sheila…”
“Ma’am?”
“Could you please step into my office? I’m going to need your assistance.”
“Absolutely Ma’am,” Sheila replied, followed by a click as the call disconnected.
Mother’s weight rose up off my back as she stood. Leaving the dildo fully embedded in my ass, she began to unbuckle the straps of the harness, first from around her thighs and then the strap around her waist. She stepped free of the contraption, leaving it dangling off the exposed base of the huge rubbery prick. My bowels trembled, clutching down tightly around the massive anal invader. Freed from the driving thrusts of my Mother’s hips, the straining muscles of my rectal fuck sleeve began to ripple, slowly setting the monstrous prick into motion. At a slug-like pace, the glistening black shaft began to ease its way out of my ass.
There was a polite tap on the office door, followed immediately by the click of the latch. I strained my head to look behind me, seeing Sheila’s face peering inside the half-open door. I should have died on the spot of embarrassment, spread out across the desk of the CEO with a massive rubber dildo buried in my ass. But Sheila was my older sister after all, and there were no secrets kept in our cozy little family. Sheila’s gaze took in my vulnerable and half-naked position across the desk, but her expression remained politely neutral. The strap-on cock shaft eased another few inches out of my ass, beginning to droop as half its length was now exposed.
Mother adjusted her clothing, tucking an untidy corner of her blouse into her pants and restoring her tussled hair to a professional look with a couple of quick brushes of her fingers. “I have to go to that meeting,” Mother informed Sheila, “so I’m going to need you to finish up for me in here.” My sister nodded, a shy smile crossing her lips as she glanced back in my direction. The rubber prick slid further from my ass, its outward progress finally halted as the bulbous knob of the cock head snugged up tight inside my quivering rectal pucker. The mostly exposed length of the long, flexible prick now swung lazily back and forth, the nylon straps of the harness tickling the backs of my calves with each gentle caress.
Sheila stepped into position behind me, hefting the massive prick into a horizontal orientation and expertly cinching the nylon thigh straps into place as Mother gathered a few necessary papers from the file cabinet. She stepped to the doorway, turning with a last-minute thought. “Oh, Sheila, when you’re done here, could you tidy yourself up and then come down to the downstairs conference room? I suspect that Mister Denton might find you… interesting.”
“Certainly Ma’am,” Sheila agreed, presenting an eager grin.
Mother nodded with appreciation. She turned, leaving the office door open and then crossed through the reception area with sharp raps of her heels on the flooring. The clear glass door hissed closed as she disappeared down the hallway. I gave a nervous glance in that direction, realizing that the view from the busy hallway was a straight shot right into Mother’s office. Already a few people had stopped, peering though the glass at the sight that greeted them.
Sheila paid them no mind, cinching the waist band of the harness securely into place. A slow, steady thrust experimentally buried several inches of the rubber cock shaft back into my ass just as the clock on the wall quietly chimed off the nine o’clock hour. I groaned, wriggling my hips as my sister withdrew and thrust again. The day wasn’t turning out to be so bad after all…
