Fetish

Defy Your Supervisor

Margaret reprimands her condescending supervisor.

Spankmasters
Jun 3, 2024
16 min read
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Break Your Boss
Break Your Boss

Defy Your Supervisor

Margaret, a 26-year-old secretary, recently lost her cock virginity to her boss Giovanni Fumagalli. He's the CEO of Vangalli Industries and has a reputation for being cocky and arrogant. He often puts Margaret down, and even though she does her job well, he doesn't seem to care. Margaret has difficulty handling foreplay or actual sex, causing Giovanni to tease her. She's only managed to have sex with him once. Margaret is 5'1, 115lbs, has G-cup breasts, a large 20-inch cock, and dresses professionally. She has dark skin and sports a cute pixie-cut hairstyle.

Giovanni is a 37-year-old CEO who's always dressed up, with a sense of elitist arrogance. He's known to degrade anyone below his social status, but accedes if sex is involved. He enjoys sex with anyone, including those with big cocks like Margaret. Giovanni is 7'7, 285lbs, wears glasses, has pecs large enough to fit an H-cup bra, a thick 15-inch cock, and a provocative style. His hair is long, dark brown, curly, and he has a full chest and body hair. He's not kind to others, but his devious side comes out during sex.

~~~~~~~~~~~~~~~

Margaret, a diligent secretary, manages her boss' finances and personal accounts. But she also faces condescension, with no thanks or acknowledgement from the slimy Giovanni Fumagalli for all of her hard work. Giovanni is the founder of a popular fashion brand and earns millions designing purses, loafers, suited apparel, and lingerie. Despite his deserve, she struggles to put up with his superiority making her feel worthless.

But Margaret tries to justify her servitude in order to cope with his demeaning behavior. He's haughty and domineering when on professional matters, trampling on her self esteem. However, he's a different man altogether when it comes to sex. He's a playboy who takes advantage of the situation.

Giovanni fancies Margaret because she has a huge cock. She's one of few women born with this, and he's obsessed with this 'gift'. He chooses to have an affair with her, promising her the 'best of both worlds'. As a doll, Margaret feels attracted to his charms and physical prowess, being unable to resist him. She is 5'1, 115lbs, and has G-cup breasts, a 20-inch cock, and dark skin. Her hair is a pixie-cut.

Giovanni is a CEO who flaunts his wealth and success. He's handsome but also arrogant, driven by status. He even connects with Margaret based on his sexual preferences and exploits her sexually. This makes Margaret think she may have to stay with Giovanni in exchange for his sexual favors. His sexual tendencies have nothing to do with gratitude; instead, he's more interested in the novelty of the situation.

Margaret dreams of finding a better job with a kinder boss, a goal constantly frustrated by his ceaseless attempts to satisfy his libido. Each time she wants to tell him to 'shove his job up his ass,' he seduces her. In fact, Margaret's boss has challenged her to a competition. She can't just walk away, Giovanni won't stop until he's had sex with her.

For Margaret, dating was complex due to her penis, so before finally turning into Giovanni's secretary/semen dispenser hybrid, she had to vent her office-related tensions or any other annoyances by masturbating. As a cockgirl, Margaret's libido was way higher than that of most middle-aged people, so she had to masturbate at least five times a day to reduce her length to a bearable size. Otherwise, her balls would swell into painful, sensitive clumps of enormous flesh that grated between her legs painfully if her thighs accidentally brushed against them. It was her stored sperm that caused her situation, and while it felt great to release it all afterward, it wasn't ideal for her mental well-being. As the time passed without climaxing, the less focused she became, and her mind would become fixated on sex. Fortunately, there was Giovanni, a typical muscle slut happy to drain her balls if necessary whenever he had some downtime. It was an unusual circumstance for Margaret at first, but when he kneaded her massive balls in his large palms, then licked up and over her weeping piss slit with his tongue, her concerns disappeared.

Giovanni didn't want anything to do with her during 9 AM to 11 AM because he claimed to still be recovering from the "trauma" of getting up so early, so Margaret stuck to making phone calls and scheduling appointments for him until noon when he was coherent to greet her with a proper, though usually late, "good morning." Margaret would frown at this, but would acquiesce when Giovanni hugged her with his swollen man breasts, a playful apology that indisputably shut her reservations down. For the remainder of her shift, Margaret indulged in Giovanni's stunning body, unable to pull her hands away from his gorgeous form until it was time to go home and masturbate to the searing sex they shared that morning. On this particular day, Giovanni, being the considerate manager he was, allowed Margaret to indulge in pleasuring him until she was content.

He closed the door to his office and drew the blinds, Margaret sat on Giovanni's lap with her nose and mouth deep in his armpit while her hand massaged a substantial breast, smooth with dark hair, beneath her shaking fingers. She moaned and humped her penis in the air like a feral dog, her mouth eagerly sucking and stripping at tan skin buried under curling hair and sticking sweat like a woman on the verge, the pungent odor of musk and sweat making her tongue salivate and eyes roll back in her head. Margaret rarely had the opportunity to truly appreciate Giovanni's body, but with the entire day to do so due to his light workload, Margaret got literal hours to burn fucking and licking the flawless body she was blessed with.

Giovanni chuckled as she continued to salivate over the hair under his arms, her tongue sinuously twisting within the crease of his armpit as she quickly roused herself to a heated craze.

"That's it, Maggie, good girl," Giovanni teased, finger dancing along the slit of her cock. "Keep at it, and I might even let you fuck me this time."

Margaret moaned and pinched Giovanni's nipple through his shirt intuitively, her penis twitching with interest when she recognized the warmth and wetness seeping through the pristine silk of his button-up. His shirt then clung to his jutting nipple like a second skin, the milky substance he dripped exuding through his shirt. Her fascination with the role reversal was a secret admiration: Giovanni, like Margaret, had added biology to the mix; a pair of humungous, tender breasts that pumped out sweet milk when she caressed them long enough. Like her, Giovanni's breasts looked like soft, flabby pecs way bigger than her own, and he loved displaying them. His wardrobe consisted only of low-cut tops and thin shirts that couldn't contain the jiggling masses of flesh and muscle that were his breasts, and the sight of those tremendous man tits never failed to make her excited when she worked in their office.

Breaking away from the cracks of his embrace, Margaret set her sights on Giovanni's chest and fastened her mouth onto one of the dripping teats. As she maneuvered about, trying to grasp the other, Giovanni groaned and rubbed his back on the couch he was seated in, admiring how Margaret devoured his nipple with her gnashing teeth. Pulling himself together, he seized Margaret's shaft with a large, red hand and ~~took long pumps up and down it~~ caressed it in an up-and-down motion. Margaret whimpered loudly, pleasuring Giovanni's burgeoning bud with bites and nibbles, while at the same time, her mouth left ... a slightly sickening taste at his hard point.

"Keep that up, Marga", Giovanni smirked, "It feels so good, doesn't it, sucking on those fleshy titties? I bet this [swollen dong] would shoot cum instantly if I let you lap more, eh?" He squeezed her girthy shaft even tighter, and his hand traversed along her fucking length, making it throb as he jerked it. Margaret moaned feebly as her lips closed on the bearded teat, sucking and munching on it with her teeth, teasing the freshly minted goo seeping through his shirt. With each pulsating grind into his palm, her jaw tightened, nudging the sweaty fabric aside, tasting better than she thought.

"...No...stop, Ok, Stop...", Giovanni demanded. "Besides that, Marga, I bet you don't know what you're dealing with...", he insisted. beaming, he tightened his grip and sped up his strokes, urging an affectrip from her immense twitch, a whitish liquid dribbling out the end of her knob.

"Bitch? What the fuck are you calling me...", Marga seethed, and abruptly broke away to glare at him, her nails digging into the man's insolent smile. He'd been gibing her about her inexperience in sex, referring to her as an easily broken virgin girl, but she knew what he hadn't seen yet. She was definitely new at sex, but she wouldn't let this snarky son of a bitch make her feel like a weak, unworthy loser. She clenched her fists, silently planning her vengeance...

"Pathetic..." Marga kind of lurched away, her upright form pointing to Giovanni's desk. "There's a lot more to me than you think, " she called out matter-of-factly, "I'll show you."

"Please...", Giovanni trailed off, flipping around on his belly and positioning her gigantic frame over his groin. "I can't wait anymore. Are you going to fuck me or not?", he asked desperately. "I'm almost dripping off the edge."

Her brown eyes glazed over at his goading words. Although she'd only just started engaging in the most improbable of sexual practices, she was nothing if not inherently determined. In spite of Giovanni's never-ending taunts, she'd kept her cock pumped for the same purpose, and two days of foreplay were culminating right now in potentially one of the wildest acts she'd ever commit. Hurriedly shuffling off her shirt and then hobbling up to Giovanni, her weight pushing her cock around, slapping against her thighs, Margaret moaned and lined herself up with Giovanni's leaking, sultry orifice, grinding the top of her head against the opening as one enormous mouth consumed the other. Every throb of Giovanni's gash locked onto her head, the words he'd told her refused to leave her mind, his asshole did indeed feel hungry, begging for more action, ever welcoming when he ruined himself. "How does this feel?", she demanded, revelling deep into his asshole; it felt fucking incredible. Biting his chest, she fucked him, watching him writhe and accept her pre-cum-laden cock with a drastic paroxysm of eagerness, readying her spine for a rodeo she better win.

"Gahhhniqueph! You're fucking me... Fuck me, fuck me..." Giovanni urged in sheer panic, panting and gasping like a beached whale. Although her stamina needed vast improvement and her tongue new ways to lock onto and drink the milk from his nipple, she was set to make her mark of domination tonight. It wouldn't be for much longer. "Fuck him! Fuck him hard!"

Margaret glared at him one last time, her eyes dying for his bullying and mean remarks. Carefully, she swung her feet out and hobbled away to gather her breath and marshal her force. Gathering confidence, she noticed a vase full of pearls conveniently positioned by his desk. Cadaverous grey eyes gleamed, focusing on the handsome man on the wood. "You're mine...forever!!" she whispered, "Now...watch yourself!"

She grabbed it, strength rushing into her frame as the brown glass glinted under the lamplight. And while Giovanni wished for her to fuck him right then and there, his eyes fearfully widened when she leapt at him, crushing the vase so hard that her target scrambled onto the floor where the shattered contents tacked him, the sweaty drops nailing his gaping groin...

Sharp, quick breaths escaped Margaret's nose as she inched her way into Giovanni's backside. His wrinkled ass gave way, embracing her thick flesh until it settled into its perfect shape. Her wide hips moved in sync with her cock's descent, and watching this took Margaret over the edge.

"Holy shit, it's actually fitting inside," Giovanni said, grinning. "Great job, Margaret, you're not the pathetic one I thought you were."

"F*ck off," Margaret spat. As she snuggled into Giovanni, his tightly-packed intestines squeezed her cock, causing her balls to tighten inside. She clutched Giovanni's hips to keep her balance.

"Fck yeah, it feels so good," Giovanni said, rocking his chest. "Keep it up. Don't fcking stop."

The pink tip of Margaret's cock slid past that last stretch and bottomed out. She shifted to fully sink into Giovanni's ass. His walls grabbed her thick tool, making her cunt swell in return. As the tender skin of his hole slid over her knob, Margaret felt her entire body flee from erotic reality.

Gripping Giovanni's thighs, Margaret wiggled her hips from side to side, flopping her cock back and forth, ramming him. Despite his gaping hole, the quickening throb of his entrails stimulated her cunt. She moaned as a breathless pulse sent her balls smashing against Giovanni's butt. His ass shivered at the contact.

"Oh God, keep going," Giovanni moaned. He alternated between jacking off and mauling his bouncing chest. "I swear to God, I'll fire you if you stop!"

"Not a chance," Margaret snarled. She yanked her hips back, aiming straight for Giovanni's insides, and collided with them. His mouth snapped shut when she set her prick back. An animalistic sound rumbled in Margaret's chest.

"It's about time someone shut you up," she snarled. "I'll make you into my bitch by the end of today."

Disregarding Giovanni's statement, Margaret's powerful hips slid in and out, rhythmically slamming her cock into his ass. Giovanni shut up from the sheer force of her thrusts. Margaret took notice and sped up; the power held in her hips was unconventionally powerful compared to her petite frame. She rocket into Giovanni's ass, commanding him from behind.

"God, keep fucking me!" Giovanni shouted. "I'll do whatever you want if you keep f*cking me!"

Suddenly, Margaret shuffled back and lunged forward with violent force, slamming back into Giovanni's guts. Pulling her cock, she thrust him, deep and unforgiving. The abdominal hut of his ass halted her movements, silencing the disrespectful whore for good.

"F*ck, fuck!" Giovanni cried. "Watch it! I-I can't handle this!"

"Shut up and let me finish this," Margaret growled. Her quickened hips battered Giovanni's prostate, compelling him to clench her thighs.

"Can't break what's already broken," Margaret said as she sucked Giovanni's nipple, detaching the half-flattened bust. "You thought you could show off those huge tits and get away with it? You forgot that I'd turn the tables on you. You're dumber than you seem, Mr. Fumagalli."

"You're - you're too much," Giovanni panted. "Please, slower."

Giovanni's tits bounced as the smaller girl violently slammed into him with her broad hips. Margaret smirked. "Nah, too late for that. I've proved my dominance today, asshole." Margaret flinched in time with every thrust. Meanwhile, the copious rippling of a pressured gut echoed.

She pressed her breasts together to further squeeze Giovanni. Juices in his pecs surged, dripping from a now helpless Brown nipple into Margaret's cupped hands. She swallowed every pearly drop. Ripping his shirt open, Margaret marveled at Giovanni's chest.

"Do something!" He cried. "It's way too quick!"

"Shut up," Margaret snarled as she sucked each nipple, swallowing as much as she could, while her hand jacked his other boob. No pleading or begging could silence her now. He had ignored her for far too long, but today, Margaret would sate every dark craving, every lust ignited by the self-indulgent, showy man in front of her.

After a few more furious thrusts, Giovanni finally surrendered, crying out and letting slip expletive-filled pleas to slow down.

"Keep f*cking me!" She groaned. "Submit to me."

Faster and harder, she rammed her cock into him. Satisfaction flooded through Margaret as Giovanni moaned and groaned in surrender. He was finally where he needed to be, and he let his guard down. Her crude prowl ended with her forced obedience.

"You young vulgar one!" The gentleness in Giovanni's tone faded as Margaret speeded up, his dilated pupils rolling back as his shallow anus dragged along Margaret's cock before it slammed back home. Margaret sensed Giovanni's desire to rebuke, threaten her, and exploit his position over her to urge her to stop suffocating him. But Margaret understood better. Giovanni lived off control, and now that Margaret had taken control, he was just like the many people he had stepped on to assert himself. The mere thought thrilled Margaret, and soon she was releasing a torrent of cum inside Giovanni's belly, the intensity of the pleasure emanating from her cock and testicles leaving her disoriented, but not interrupting the smooth motion of her humping hips. Giovanni whimpered then and squirmed at the feeling of having come inside his hole, abhorring the notion but resigned to enduring it until Margaret was satisfied.

"Stop, Margaret, you whore, pull it out of me!" Giovanni cried miserably, his youthful appearance blotting as his stomach swelled with seed. "Take out your filthy seed from me, you beast--!"

Margaret silenced Giovanni again by clutching both of his teats in her mouth as she fucked him frantically with increased enthusiasm, the abundant semen that filled his violated insides spurting out of his loose fundament in spurts. Margaret revelled in the lubrication her sperm provided and experienced momentary illumination. This was the divine act of sex, she thought blissfully in her head. Here she was, guzzling the divine nectar within Giovanni's chest while inseminating his expansive anus with her seed, retribution for the countless hours she spent being bullied in his office. Today would certainly be the day when Giovanni Fumagalli became Margaret's -- it would finally be his.

Margaret, in spite of the internal voice advising her not to, detached herself from his nipples and beamed up at him, her disfigured lips and blushing cheeks causing his face to displeased. He yearned to chastise her so desperately, but Margaret was not going to let him.

"Let's establish some clear rules here, Mr. Fumagalli," Margaret began, her erect prick stilling in his rectum. "From now on, you'll stop treating me like a canine you lead with a chain. Changes are coming whether you approve of it or not." She then introduced her endowments to him, substantial mammaries that struggled to fill her hands, and pressed them against his length. "Not only will I get a raise, longer break, and the respect I deserve, but you'll be my enslaved cock-sucking fuck-toy for eternity. A thick, muscular slut who thrives on licking my cock and beating up my testicles. Is not that a good deal?"

"You're an idiot for believing you can dictate me, temporary worker!" Giovanni snarled through gritted teeth, his face contorting as he involuntarily thrust into Margaret's pliant tits. "You're nothing but a work animal! A cunt who should be thrilled just to be allowed to touch me!"

"I see everything you say," Margaret responded with a playful tongue click. "It still doesn't matter." Grinning up at him with her immaculate teeth, Margaret resumed smothering Giovanni's chest with her huge breasts. "Let's find out how swiftly you crack."

Margaret refrained from considering the abrasive words falling from Giovanni's mouth and continued shoving herself into him furiously, sweat trickling from her temples and vaselining her ample mammaries as effort overwhelmed her. She could sense a second load rising into her shaft, far larger than the first, prompting a longing moan from Margaret when her genitals constricted, stimulated her balls, and propelled her last jets of generative fluid into the worn anus within, awakening further yet more protests from Giovanni. Yet her irritating calls failed to penetrate her mind, and Margaret continued the merciless attack on Giovanni's prostate, driven by the ruthless pounding and the softness of her breasts covering his prick, finally managing to fire off the last burst of her arousal. Giovanni erupted at the sound, howling as he vomited his semen all over Margaret's breasts and abdomen. Margaret merely chuckled and kept plugging her ass into Giovanni's fundament.

"Fuck, Margaret, fuck, that's enough!" Giovanni pled, his pupils dilating as deep within his belly, his face convulsing with repugnance. "I'm gonna cum! I'm gonna fucking cum if you keep this up!" [End of paraphrased text]

Margaret's mind was flooded with thoughts of impregnating and penetrating Giovanni as she couldn't even hear him at the moment. Although Giovanni can't carry a child, witnessing his bloated stomach full of her semen was fueling her desire to breed her boss like the womanizer he is.

"I need to reproduce, I need to fuck this guy silly..." Margaret mumbled. "I won't stop until you're pregnant with my sperm..."

Giovanni could only permit Margaret's onslaught as his legs gave in and he sank into the couch. A helpless victim of her whims, Giovanni was unable to resist, allowing Margaret to manipulate him into any position she desired. Margaret fucked him on the couch, on the floor, against the wall, and on the desk once more, emptying her balls into both Giovanni and various surfaces around them. By the time she slowed down, Giovanni was covered from head to toe in a thick layer of her cum that entangled his hair and soaked into whatever remained of his clothes. Once her cock went limp, Giovanni lay there, a moaning, trembling mess of whimpers and moans, writhing helplessly on the soiled carpets beneath him.

Margaret withdrew her rock-hard cock from Giovanni's ass as her come poured out of his gaping hole, forming a torrent of white that puddled around her bent knees before settling on the floor. Despite this, Margaret continued rubbing Giovanni's distended stomach, encouraging more semen to spill forth. Giovanni convulsed wildly at her touch and bared his teeth together when his depleted cock leaked her cum that merged with the mess on the floor. His heavy tits, now stained with hickeys and bite marks, generated pathetic droplets of milk that stained his chest.

Margaret admired the view.

"It seems Giovanni Fumagalli, the infamous fashion CEO, has been brought down a peg," Margaret chuckled as she scuttled over to Giovanni's head, her hand instinctively moving toward her sopping member. "Not bad for a virgin, huh? Instead of a secretary, I don't mind being your personal bitch trainer. Has a nice ring to it." She slid her dick against his lips and prodded forward. "Now why don't you be a good slut and clean this mess up for me, huh? It's your mess, so you better deal with it."

Giovanni had no choice but to indulge Margaret's requirements and suck on her cockhead while licking up her overflowing cream. He remained silent throughout his task, showing no signs of resistance. The world's most renowned fashion CEO was now a shattered slut who lived to serve his secretary, and Margaret found this outcome very satisfactory.

..........................................

Margaret was thrilled with the reality after defeating Giovanni.

Giovanni no longer teased or condescended Margaret. He was now nothing more than a toy she could manipulate for her pleasure, a slave that existed only to harbor her jizz. While ostensibly still cold and unfeeling to everyone else, Giovanni yearned for Margaret's touch whenever she was alone with him. She frequently fucked his face, his tits, and his anus like she couldn't live without it, to which he enthusiastically welcomed her invasion.

"I adore Maggie's woman cock..." Giovanni cheered as he hovered above her thighs, bobbing up and down on her small dick. "It rivers my slutty male rectum so well, I can't go on without it..."

"That's right, Gio, perform for me, show me how far you can take it," Margaret smirked as she watched Giovanni's cavernous ass take her length. "My sperm-filled balls have been so heavy today; I hope you're ready for more."

"Oh please, Maggie, shoot your seed in my gut!" Giovanni hoped, his hips swaying faster. "Fill my tummy with your kids and fuck me with your baby batter, sweetheart!"

"Good boy..." Margaret proudly inspected the masterpiece she'd created from Giovanni and spent her workdays intensively plugging him until she returned home for the night, resting, and then beginning anew every morning. Not many people can say they earn forty bucks an hour to fuck their outrageously handsome boss and he loves it, but Margaret had hit the jackpot; who knew having a large quim would open up so many career opportunities?

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