Break Your Boss

Margaret Hutchinson: A 26-year-old secretary who has recently lost her cock virginity to her boss Giovanni Fumagalli, the notoriously pompous CEO of Vangalli Industries. Hardworking and kind, Margaret takes her work seriously but is often put down by Giovanni for no other reason except that he enjoys watching her squirm. A quick shot, Margaret is unable to handle foreplay or actual sex without creaming herself due to her lack of experience which Giovanni does not waste a second teasing her for. She's only ever managed to have proper sex with Giovanni once because of this. She is 5'1, 115lbs, has G-cup breasts, a 20-inch cock, and likes to dress professionally. She has dark skin and keeps her hair in a cute pixie-cut style.

Giovanni Fumagalli: The 37-year-old CEO of Vangalli industries and the object of both Margaret's hatred and desires. Haughty and imperious, Giovanni is an elitist who proudly steps on and degrades anyone who isn't of the same social standing as him but is known to make slight concessions if sex is involved. He will fuck anything and anyone but has a particular fondness for dickgirls that borders on fetishism. He is 7'7, 285lbs, bespectacled, has pecs big enough to fit an H-cup bra, a 15-inch cock, and dresses very provocatively. He has long curly dark brown hair, tanned skin, stubble, and hair on his limbs and chest.

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Margaret considered herself a good secretary, so it was only natural that as the very person who managed her boss' finances and personal accounts, she'd be respected a little more by Giovanni every now and then. As CEO and founder of one of the world's leading luxury fashion brands, Giovanni made millions each year designing purses, loafers, tailored suits, and underwear for rich clients, and as his reputation and earnings grew, so did his ego. Haughty, arrogant, and condescending as he was patronizing, Giovanni didn't care for anything that wasn't his looks, his money, his reputation, or anything that didn't involve himself and the influence he held in the fashion world. Most people can look past his snobbish behavior simply because he was just too damn handsome to stay mad at while sane people like Margaret, the 1% of the population that deigned to find a flaw within Giovanni's character, couldn't stand him. Margaret has been a dutiful, compliant secretary for the man for over three years now and she's never received a single "thank you" from him; just the same emotional and verbal abuse she's been forced to take on the chin ever since he hired her. She only stayed because the money was good, but now she isn't too sure if the money was even worth it anymore.

Or at least that's what Margaret likes to tell herself.

Margaret wants to leave. She wants to move on and find a job with a boss that will actually appreciate her, but it's so fucking hard to do that when Giovanni effortlessly exploits the one thing about Margaret that keeps her from leaving. While Giovanni was a prim and proper elitist who would sooner step on Margaret's back to cross a muddy puddle than to ever get his loafers dirty, Giovanni behaved no better than a back alley whore when sex was concerned. He'd fuck anything with a pulse no matter age, gender, or status so long as he was able to get his rocks off, but his favorite type of partner by far were girls like Margaret; short and voluptuous young women that not only had tight little pussies between their legs but hulking cocks that hung to their knees as well. Margaret was one out a few thousand women born with this condition, and while Margaret hated the added annoyance that came with hiding as well as managing her monstrous prick all the time, Giovanni didn't care and immediately singled her out as his latest "pet" if it meant gratifying his cockgirl fetish. At first Margaret was confused why her boss, this devilishly charming rogue of a man with the strength of a bull and the body of a god, would even think to choose her to have an affair with, but his reasoning, though lurid, was as solid as the cock throbbing in his slacks when he pressed his teeming erection against her own after propositioning her.

"The best of both worlds, wouldn't you agree?"

Suffice to say, Margaret was hooked.

Dating for Margaret was difficult given her penis, so before ultimately succumbing to her fate as Giovanni's hybrid secretary/jizz dispenser, Margaret was forced to release her work-related frustrations or whatever else pissed her off by masturbating. As a cockgirl, Margaret naturally had a much higher libido than most men and women her age, so she had to jerk off at least five times a day to get her length down to a manageable size. If she didn't, her balls would swell into taut, sensitive heaps of oversized flesh that thrummed painfully between her legs if her thighs so much as brushed against them. Backed up sperm that aged and ripened in her trembling sack was to blame for her condition, and while it certainly felt good to shoot it all out after depriving herself of her needs, it didn't bode well for her mental state. The longer she went without busting a nut, the less focused she became, and her mind would turn into a mushy mess obsessed with sex if she went a day without orgasming. That's thankfully where Giovanni came in, a typical muscle slut willing to drain her balls if need be whenever he had the time to take a break. It was an odd arrangement for Margaret at first, but after letting Giovanni cradle her giant balls in his big hands and watching him work his tongue up and over her weeping piss slit, Margaret had very little reason to complain.

Giovanni wanted nothing to do with her between the hours of 9AM and 11AM because, as he liked to put it, was still recovering from the "trauma" of waking up so early, so Margaret acquiesced to making phone calls and setting up appointments for him until noon, when Giovanni was lucid and ready to greet Margaret with a proper, albeit delayed, "good morning". Margaret would frown at this, but would accept his presence when Giovanni smothered her with his heaving man titties as a playful way to "apologize" to her, an action that immediately shut Margaret's reservations down. From there, Margaret would indulge in Giovanni's gorgeous body for half of her shift, unable to tear her hands away from his beautiful physique until it was high time for her to go home and jerk off to the hot sex they engaged in earlier that day. Today was one of those days, and Giovanni, being the "generous" boss that he was, would let Margaret do what she wanted until she was satisfied.

The door to his office locked and window shades closed, Margaret sat across Giovanni's lap, nose and mouth buried deep into his armpit while her hand kneaded a big round tit, dusted with fine dark hairs, beneath her trembling fingers. Moaning and humping her cock into the air like a rutting dog, Margaret sucked and laved at tanned skin buried beneath curling hairs and clinging sweat like a woman starved, the strong scent of musk and sweat washing over her shuddering tongue making her mouth water and her eyes roll into her skull. It was rare that Margaret got the chance to truly enjoy Giovanni's body, but now that she had the whole day to do just that no thanks to Giovanni's lax workload, Margaret had literal hours to burn fucking and licking the hot body that Giovanni was blessed with.

Margaret heard Giovanni chuckle as she continued to drool over the hair under his arms, tongue worming around the crease of his armpit as she quickly worked herself up into a heated frenzy.

"That's it Maggie, good girl." Giovanni teased, finger prodding the slit of her cock. "Keep it up and I might let you stick it in me this time."

Margaret moaned and pinched Giovanni's nipple through his shirt out of reflex, her cock twitching in interest when she feels something warm and wet seep through the pristine silk fabric of his button-up. His shirt then clings to his stiffening teat like it was a second skin, the milk expressed by his soft tits forming a wet enough damp spot that lets Margaret see his big puffy nipples through his shirt. Much like Margaret, in a unique twist of cosmic irony, Giovanni had added biology as well; a pair of big tender breasts that gushed with sugar sweet milk when she played with them long enough. Round and fat like real tits, Giovanni's breasts resembled big squishing pecs many times larger than her own, and Giovanni loved showing them off. His wardrobe consisted entirely of low cut tops and thin shirts that barely contained the jiggling heaps of fat and muscle that were his breasts, and the sight of those gorgeous man tits never failed to make her hard while working in the office.

Ripping herself away from the crevice of his arms, Margaret set her sights on Giovanni's chest and latched onto a leaking teat as she let her fingers grope and pinch the other. Giovanni moaned and sat back in the couch he was laying in then, eyes admiring the way Margaret sucked on his covered tit, her overeager mouth and tongue aggravating the growing wetness around his areola with her spit. He then promptly returned the favor by grabbing and stroking the trunk of Margaret's shaft with a great big hand, the older man's ruddy palm barely closing around her shaft when he made long passes over her twitching length. Margaret groaned pathetically at that and chewed around Giovanni's swollen teat with gentle drags of her teeth, her tongue briefly catching the faint taste of sweet cream through his sopping wet shirt as she humped feverishly into his fist.

"Don't stop, Maggie, keep sucking those tits," Giovanni smirked. "Tastes good, doesn't it, sucking on those fat titties? I bet this fuckstick would cream in an instant if I let you drink more, hm?" He then grips her shaft tightly and watches precome erupt from her cockhead and roll down her venous skin in thick rivulets. "Virgins are so cute..."

Margaret grimaced at Giovanni's comment and bit down on his teat, the pressure making Giovanni flinch in a stark mix of pain and pleasure. Margaret wants to call it hot but is too prideful to give Giovanni the satisfaction.

"You always beg for my dick..." Margaret grumbled. "Even if I'm not the most experienced, this virgin can still turn you into a wailing slut no problem."

"Oh really? I'd love to see you try, Maggie." Giovanni then took hold of Margaret's waist and made her lay down on the couch so he could straddle her. "Aren't you the same sad little virgin girl that comes untouched when she so much as buries her face into my chest?" Giovanni moved further up Margaret's much smaller body to swaddle her face in his hanging breasts, the older man laughing at the hitch he heard in Margaret's voice when his plump tits smothered her cheeks. "Such a weak constitution... If not for that big cock, I would've found a better bitch who can actually satisfy me by now."

Margaret narrows her eyes at Giovanni's words as she fights down the urge to nuzzle her face into his breasts. While Margaret was still very new to sex, that didn't mean she was a helpless virgin like Giovanni claimed. Never in a million years did Margaret ever expect herself to be the willing plaything to a gorgeous egomaniac like Giovanni, so her tolerance for blowjobs, handjobs, tit sucking, and actual intercourse was...poor to say the least, but she was getting better dammit! Giovanni never spared a moment to tease and insult her for her lack of endurance, but she'll show him. She withheld jerking off for the past two days for this very moment and she wasn't going to let this big mean bimbo take the piss out of her anymore.

"Asshole..." Margaret squirmed away from Giovanni's massive body to point at his desk. "I'll turn you into a walking fleshlight when I'm done with you. Just watch."

"Ooh, I'm shaking," Giovanni got off the couch to strut towards his desk and lay his big body across the polished mahogany surface. Twirling a bit of hair around his finger, Giovanni patiently waited for Margaret to make her next move as he slowly spread his legs for her. "Well come on now, you know I hate waiting. Let's see if you can actually get the tip in without coming all over yourself this time."

Margaret's brow twitched in annoyance, but kept her opinion to herself for now. As she stripped herself of her blouse, Margaret hobbled over to where Giovanni laid, cock swinging and swaying in time with her steps as her rapidly swelling balls bounced between her thighs. Giovanni meanwhile licked his lips at Margaret's big tits and leaking prick and immediately shedded himself of his slacks and underwear, revealing a bronze cock and heavy sack of nearly equal length and mass to Margaret's that sat above a winking asshole. Margaret shivered at the sight of Giovanni's oversized hole in full display and quickly mounted the older man so she could line herself up along his twitching entrance. Broken and ruined for good thanks to his own sexual escapades, the sunken hole that was Giovanni's man pussy clung to the tip of Margaret's thick cock like a sucker, protruding outwards and holding onto her prick for the briefest moment before receding into place again as it left a sticky trail of sweat and pre-ejaculate in its wake. Margaret loved servicing this big broken hole with her mouth until her nuts ached, but as much as she wanted to make out and tongue-fuck this literal manwhore until the cows came home, her cock was practically pleading with her to fuck him already.

Breathing sharply through her nose, Margaret slowly pushed into Giovanni's ass and watched her length stretch out his hole to its limit. His wrinkled ass puckered and gave into the turgid meat sinking into its depth, conforming to the shape of her girth effortlessly like it was quite literally made for her cock and her cock alone. Just watching her prick sink into her boss' well-used ass was enough to make Margaret's balls clench up into her pussy, and the tired secretary had to hold onto Giovanni's hips to steady herself.

"Mmm, it's actually going in this time..." Giovanni bucked his hips happily, making his tits bounce. "Good girl, Maggie, you're not as pathetic as I thought you were."

"Fuck off," Maggie cursed, unable to maintain her composure when she finally bottoms out inside Giovanni. Despite how loose his actual hole was, Giovanni's guts were still deliciously tight by comparison; the slick, trembling walls of his ass doing a splendid job at stimulating her girth. It's enough to drench her cunt and force the oversized balls pressed firmly into the swollen rim of Giovanni's hole to pulse and undulate against his skin, a sensation that made Margaret rock her prick into Giovanni's ass. As she dug her nails into olive-tinted skin, Margaret humped her boss's hole like a dog, her cock planted firmly in his guts as she pumps her wide hips in short, fast bursts, doing everything she can to revel in the wetness that closes around her length. Giovanni moans out his pleasure through it all, his voice loud and wanton as he alternates between jerking himself off and massaging his expressing breast with one hand.

"Fuck yes, keeping fucking me with that fat girl cock," Giovanni groaned. "If you stop, I swear to God, I'll gut your pay..."

Margaret barely heard Giovanni as she was too focused on her own pleasure to give the spoiled whore any mind right now. She did however hear the condescending tone in his voice and figured it was high time to kick it into overdrive and give her slutty boss the dick down he deserved.

"It's about time someone shut your mouth for once..." Margaret growled as she held onto his sculpted thighs. "You'll be my bitch before the day is over."

"I wonder where this confidence came from." Giovanni scoffed through his nose. "Finally hard enough to fuck me for once and now she thinks she can call the shots? You forget your place sometimes, Maggie--!"

Suddenly, with power that belied Margaret's petite figure, the younger girl reared her hips back as far as she could, pulling her cock with her, and then slammed back inside Giovanni's guts to sheathe her length again. The force behind her thrust shuts him up instantly and Margaret pounds his hole again and again to keep it that way, the young secretary battering his prostate with such power it makes Giovanni cling to the edge of his desk.

"Fuck, fuck!" Giovanni cried out, his body jostled by the pummeling she was giving his ass. "T-Take it easy, you--!"

"Shut up and take this cock, slut!" Margaret panted out and went faster, fat nuts slapping against Giovanni's taut rear end. "Sick of you and your pretty pompous ass putting me down everyday, gonna take you down a peg and pump this bitch hole with my jizz!"

Margaret then bent over Giovanni's body to steady her thrusts and rip off the tight shirt that kept Giovanni's tits hidden, revealing jiggling pecs and puffy brown nipples that weep gut-busting milk Margaret can't stop herself from indulging. Hips still going a mile a minute, Margaret sucks a bouncing titty into her mouth and greedily drinks up the sugar-rich cream that washes over her tongue while her hand works to milk Giovanni's other breast dry. Her boss gasps and then throws his head back as he's fucked and sucked into submission by his pent-up secretary, the grunts and groans that escape his throat belying the words that quickly fall from his mouth.

"Maggie, slow down!" He pleaded. "You're too rough!"

"Can't break what's already broken." Margaret said against his skin. "I dunno why you're complaining. This is what you wanted right? For me to fuck this big ass like the slut you are?" She then cupped his pecs in both hands and pushed them together, forcing more milk to spill from his swelling teats and roll over her fingers in fat white drops. "When you strut around the office showing off these big titties all day, did you really think I'd go easy on you? You're dumber than you look, Mr. Fumagalli."

"You fresh mouthed little...!" The bite that Giovanni held in his voice softened when Margaret went faster, the older man's eyes rolling into his head as his puckered asshole drags along Margaret's cock before it's slammed back into place. Margaret can tell Giovanni wants to complain, wants to threaten her and hold his status over her head to get her to ease up on him, but Margaret knows better. Giovanni got off to control, and now that Margaret has seized that control, he was just as helpless as the countless men and women he's stepped on to get his way. The thought alone is enough to make Margaret's pussy clench, and before Margaret knew it, the secretary was blowing her load deep inside Giovanni's guts, the pleasure that surged through her cock and sack so intense it knocks the wind out of her lungs, but not enough to stop her pumping hips. Giovanni let out a broken scream then and cringed when his belly filled up with virile girl spunk. He absolutely despised having come inside his hole, but he was just gonna have to deal with it until Margaret was finally done with him.

"No, Margaret, you cunt, pull it out...!" Giovanni spat, the older man pitifully watching the muscles in his stomach fade into his skin as it bloats round and full with seed. "Get your filthy come out of me, you rotten--!"

Margaret shut Giovanni up once more by taking both of his teats into her mouth as she fucked him silly with newfound fervor, the come that flooded his bruised innards shooting out from his loose ass in spurts. Margaret enjoys the added lubrication that her sperm provided and felt her mind go blank. This was fucking heaven, she thought blissfully to herself. Here she was, gorging herself on the sweet man's milk that welled in Giovanni's chest as she emptied her balls in his huge ass, revenge for all the grueling hours she spent sitting in his office taking his abuse. Today will definitely be the day that Giovanni Fumagalli officially becomes Margaret's bitch.