After Hours with Ornella

"Danny! Ornella needs you."

Danny put down the report he was reading, left his cubicle and walked down the hall toward his boss's office. Her door was closed, but Jennifer--Ornella's secretary, who had just called for him--motioned for him to proceed inside.

"She's on the phone," warned Jennifer, so Danny eased the door open carefully.

Ornella's back was turned to him as he entered her office, which offered an expansive view of the city through a window that extended the length of the room. She held a phone to her ear while shuffling through a mess of papers scattered across her desk, seemingly irritated with whomever she was speaking to.

Danny's gaze immediately magnetized to his boss's exquisitely formed rear. A pair of heels and sheer black stockings accentuated chiseled calves, and a jet-black pencil skirt clung tightly to her muscular thighs and wonderfully plump ass. The Latina's lower half matched the stereotypical description: impeccably toned legs and mouth-wateringly juicy cakes. A milky white blouse was tucked into her skirt above the waist, and her shiny black hair was tied back in a ponytail.

His boss glanced at the door as he entered and held up a finger, indicating that she needed a moment.

"That should work fine, but make sure the client knows we won't budge from that price." Her voice was clear and confident, with pronunciation that betrayed only the slightest traces of a Spanish accent. "Hang on a second Bill, someone's at my door--"

Ornella lowered the phone from her ear and covered the receiver with her hand as she turned toward Danny. Black glasses framed her sharp brown eyes and elegant tanned features, and she wore an expensive-looking pearl necklace to match her blouse. The top button was undone, displaying just enough cleavage to hint at the rest of the enormous bosom concealed beneath the silky fabric. The only signs of Ornella's age were the faint streaks of grey through her hair and subtle wrinkling around her eyes, which enhanced the overall MILF-effect.

In short, she was stunning; a master sculptor would be hard-pressed to capture a better example of the natural ripening of a curvaceous female physique.

On top of her tantalizing, succulent figure, she exuded competence, professionalism, and class, which altogether made her an intimidating figure in the business setting. Apparently, she had been a star performer for the firm since her twenties, and now in her forties she was the CFO of the entire North American division. Needless to say, she was leaps and bounds above a bottom-rung intern like Danny in the company hierarchy.

"There you are. I'm going to need you tonight, so come by my place around seven. Oh, and stop by Jennifer's desk before you leave--I had her pickup some stuff for you. Bring it tonight."

With that, she returned the phone to her ear and turned away from him dismissively. They both knew that Danny would follow her instructions without question.

"Sorry about that Bill..."

After gently shutting the door, Danny exited Ornella's office and made his way to the reception desk, where Jennifer was eating a salad and fiddling with her cellphone.

"Ornella said that you have something for me?" Danny asked in response to the questioning look the cute blonde secretary gave him.

"Oh, right. Your, uhm, supplies." Jennifer cleared her throat nervously and handed Danny a bag from beneath her desk. He blushed at her expression, which contained a mix of something like sympathy and distaste. Danny didn't need to look inside the bag to have a pretty good idea of its contents. "Good luck with your... project!"

Danny thanked her abashedly and headed back to his cubicle. He sank into his chair with a sigh, remembering when he'd thought he might have a shot with Jennifer. The idea was laughable now.

Sorry, can't play tonight. Work stuff.

Danny sent the text to his buddies over their group chat; he was supposed to join their party in a multiplayer video game tonight. It wasn't the first time his boss's plans took priority over his, and it certainly wouldn't be the last.

*********************

Six hours later, Danny was on his knees in front of Ornella, eye-level with her waist on the floor in her apartment. He watched as she unzipped and dropped her skirt to expose, strapped to the inside of her right thigh by a stretchy satin band, the most impressive cock he had ever seen. Despite Danny's intimate familiarity with his boss's awesome package, it was always a humbling reveal.

Ornella stepped out of the skirt gracefully, then pulled down the band and unslung the beast from its restraint, allowing it to tumble out a few inches from Danny's face. He breathed in the virile wave of pheromones that radiated forward with fragrant, aphrodisiac effect, wincing at the slight pang of jealousy he felt. Without hesitation Danny leaned forward and gently dragged his tongue across the underside of her shaft, causing blood to flush through its length as her python angrily reared its head. By the time he reached the end, a pearl of precum had formed on her slit, which he lovingly enveloped with a slimly smooch. Ornella tilted her head back and groaned with relief, temporarily pausing to allow the boy to suckle on her swelling head. It wasn't long before Ornella's cock stood at its full, glorious mast: thick veins latticed up the dark skin of her appendage to the glaring tip, and her heavy, bloated balls hung low, seemingly locked in a tug-of-war contest with her giant member.

"Not so fast..." Ornella pulled away from Danny--who reluctantly relinquished her rod like a bitch in heat--and strode out of the room to the adjacent kitchen, her bountiful posterior jiggling with each lilting step. Danny waited until she returned, a glass of red wine in one hand and her cell phone in the other, her raging erection jutting out brazenly from the waist. Ornella sank into the seat of a black leather couch and took a healthy swig of wine before setting the glass down on the coffee table beside her.

"Okay, go ahead puta."

Having received the green light, Danny impaled his face onto Ornella's massive cock. He made it a respectable distance down her shaft before getting stuck, unable to squeeze her bulbous head past his tonsils. Struggle as he might, he couldn't quite make it fit, and came back up with a retch of slobber that coated his chin and nose.

GLUCK...

After steeling his resolve, he tried once again, and this time managed to push past the constriction at the back of his tongue. Once Ornella's tip breached the opening to his throat, Danny was able to slide down the remaining inches of exposed skin, feeling a measure of pride at accomplishing the sword swallowing feat on only his second attempt. When his lips reached the base of her length, he buried his nose into the luscious brown tangle of her pubic mound, and--stubbornly suppressing a momentary gag reflex--inhaled deeply as he urgently lapped at her engorged balls and gazed up from between her thighs.

Danny crossed his eyes in the classic ahegao face that he had learned from Japanese hentai and moaned earnestly into her modest belly pudge, attempting to arouse her by demeaning himself in as lewd a manner as he could manage. She preferred him to use solely his mouth and throat for blowjobs, so he obediently kept his hands on his knees while he knelt on the rug in her living room. The interior of Ornella's home was upscale and modern, fitted with tasteful décor that reminded occupants of her lavish salary.

Ornella sprawled out carelessly on the couch, still clothed apart from the skirt and heels she had discarded, her generous hips and ass protruding from the seat-cushion to ensure that her cocksucker had full access to her groin and taint. She lazily swiped through a dating app and messaged a few of her new matches, for the most part ignoring the lingerie-clad boy at her feet. Danny was naked aside from the matching set of black lace thigh-highs and open-nipple bra that Jennifer had given him earlier. A strand of precum oozed from the flat steel chastity cage between Danny's legs down to the floor, and every so often he ground his hips down on the hilt of the buttplug--which he had also received from Jennifer--that was firmly embedded in his ass.

Danny held the deepthroat patiently, continuously lapping at the slick, spit-shined underside of Ornella's shaft, and even managing to swallow around her pole a few times to enhance the throat-massage. He waited until she flicked her gaze down to her lap and grunted approvingly--indicating that she liked what she saw and felt--before he drew back and gasped for air. Her meaty shaft slapped down wetly across his face, and he let it rest there while he panted, tongue lolling and eyes shining adoringly up at his boss with the look a begging puppy gives its owner.

"That's a good little cunt-boy," Ornella purred distractedly, seemingly more interested in her phone than in her fit young boytoy's slutty display.

Once he had caught his breath, Danny dove back onto her pole, this time remaining near the tip and focusing his efforts on her regally-formed crown. He kissed her head with pouty dick-sucking lips, teased the slit with his tongue, and pulled her tip from his vacuum-suctioned mouth to produce moist, erotic smacking sounds. The blowjob dripped with sultry desperation, as if Danny were attempting to seduce the woman attached to the whopping cock and the only possible means of conveying his desire was through fellatio. He repeated this pattern a few times, then slid down the shaft to her sack, tenderly alternating between each of her swollen balls before sucking them both inside his mouth. He caressed them with his tongue while they steeped like a bag of tea, causing him to salivate excessively until every crevice of his mouth was filled with the salty brine of Ornella's unwashed ballsack. He finally relinquished her nuts and gulped down the mouthful before moving further south, spending a couple of minutes on her gooch before arriving at his ultimate destination. Once there, Danny orally embraced Ornella's asshole, and proceeded to toss her salad with doting, cringeworthy indulgence.

Ornella unconsciously spread her legs a bit to open up her cheeks for Danny, who eagerly dragged his tongue across her pucker with deep, heavy strokes. He alternated between licking and kissing, creating a sloppy mess of sweat and spit as he hungrily made out with Ornella's rosebud. The relaxed vixen began to absent-mindedly stroke her meat while Danny polished her hole, occasionally murmuring with appreciation when Danny's tongue pressed especially deep past her sphincter. Her hefty scrotum rested comfortably on his face, further clouding his senses with the overpowering musk of ass and genitals. The pathetically fervent ass worship continued for about ten minutes--although it felt like the blink of an eye for Danny--before Ornella broke into a laugh as she finally noticed just how vigorously the boy was frenching her asshole.

"Well, someone certainly seems to be having fun! Nothing like a good make-out sesh is there? I suppose you wouldn't know, seeing as how you've never had the traditional mouth-to-mouth kind... this might be the closest you'll ever get to the real deal though, so I get the enthusiasm. Plus, considering all the kissing practice you've had with my ass, you'll definitely be prepared if some drunk girl at a bar ever takes pity on you. Oops--" she grunted as she let out a wet toot into Danny's face.

Danny whined with embarrassment but sucked in through his nostrils, filling his lungs to the brim with her scent. He squirmed beneath an irrepressible wave of humiliation, but continued to doggedly slurp on his boss's anus. The oral performance would put a seasoned pornstar to shame, and was sincere enough to warrant an affectionate pat on the head from the recipient.

"Alright, that's enough. Hop up here and show me your tush. I've got about an hour before I need to leave for this party and I'm pretty backed up. Haven't nutted since Monday."

"Yes Ma'am," Danny replied before doing as Ornella instructed.

Ornella hadn't needed Danny for two weeks, which meant she'd probably been fucking a new girl in the meantime. This wasn't unusual; Ornella had a voracious sexual appetite and never had much trouble picking up chicks. Publicly, she exclusively dated girls, but Ornella had discovered that Danny was a pretty good outlet when she needed to unwind, often after a long day at the office. In addition to his responsibilities as an intern, Danny had become Ornella's on-call cumdump. Essentially, a masturbatory aid when no hot girls were available.

Occasionally she would even summon him directly after a hookup, if Ornella was left partially blue-balled by a girl who'd been unable to handle her donkey-sized dick. She never showered in between, and liked to show him a picture of her date--always a babe--so that Danny could visualize someone when he cleaned up the residual coating of pussy juice from her hog. Now you can say you've tasted some pussy, she'd joked the first time it happened. Danny couldn't help but imagine how intoxicating the real thing must be, and he burned with the thrill of discovering a unique flavor of sweetness and tang in each new woman's froth. As backward as it might be, he had even started to feel lucky that Ornella allowed him taste the sex of such gorgeous women. Albeit, only indirectly, once they had creamed all over her monster. He couldn't blame them for being tapping out, either; Ornella's size could rival any of the biggest mandingos Danny had seen in porn, and usually not even the size queens could fit them fully inside.

Holy shit, most girls can only take me halfway! Ornella had exclaimed when she'd taken his anal virginity, clearly surprised at being able to fully sheath herself into his butt. I can't remember the last time I bottomed out in someone...God it gets annoying. Not something you'd understand, but honestly, having a big dick isn't all it's cracked up to be. I could really get used to this...it might be a fake pussy, but it's tight as fuck, and I can't even get you pregnant! I should've started fucking gayboys a long time ago. Kind of a win for you too--even if you only get to use your ass, at least you're getting some action right?

Danny made sure to arch his back once he assumed the face-down ass-up position next to Ornella on the couch, submissively offering his fresh, deliciously smooth rear--she made him wax twice a month--while thin tendrils of precum dripped from his cage. Doing so exposed the base of the new buttplug Ornella had gotten him, on which the word "SLUT" was printed in bold font. Ornella, still seated, leaned over and began to ease the plug out of his butt, causing Danny to moan as his asshole clung greedily to the toy. Ornella whistled when Danny's ass finally widened enough to accommodate the absurdly huge sphere, releasing it with a sickening suction noise that left his delicate pink gape twitching in a pitiful attempt to close.

Ornella licked her hand and used it to lube up her cock--not that it was particularly needed, considering the copious amounts of precum she produced--then hawked up a wad of phlegm and spit directly into Danny's open gape for good measure. She then shifted onto her knees and gave his cock cage a tug, guiding his asshole back to line up with the tip of her monster. Slowly, but in one fluid motion that knocked the breath out of Danny, the caramel bombshell buried her incredible endowment into the plushy folds of his ass, letting out a sigh of supreme satisfaction as she did so. Danny briefly felt the weight of her magnificent breasts--he'd never actually touched them with his hands--press against his back through her blouse as she clutched him to her chest, relishing the luxurious feeling of his ring spasm around the base of her shaft.

After a contended pause, Ornella began stroke her cock in and out, only slightly withdrawing so that she stirred up the slippery pool of anal juice inside Danny's guts. Within a few pumps she had created such a creamy, gooey mess that it was hard to tell where her cock ended and his intestines began. Danny groaned in discomfort as he willed his entire body to acclimate to her size; not even wearing the plug for the past few hours could entirely prepare him for her girthy, veiny slab of marble.

Ornella slowly picked up the pace, thrusting her hips with precision as she ruthlessly wore down any initial resistance the boy's ass offered. Her face bore a slight frown while she fixated on elasticizing Danny's asshole, as if irked at the necessity of stretching it out prior to use. The process took a few minutes, but eventually her buttfucking elicited a stream of thirsty, feminine moans from Danny, which indicated that he had crossed over the threshold from pain to pleasure. Or at least, some combination of the two.

Once she was satisfied that his hole was sufficiently broken in, Ornella really let loose, gluttonously drinking in the sight of Danny's perky bubble-butt reverberating in time with her progressively more powerful backshots. It was like a carnal, predatory instinct was triggered within the alpha female, a reptilian brain impulse that compelled her to subjugate his ass with focused, smoldering aggression. Danny's awareness of his surroundings slowly began to melt as he succumbed to the irresistible fog of Ornella's lust. The submissive instincts she had drilled into him took over, and all of his cognitive faculties subordinated to one overriding need: to satisfy the gorgeous MILF who was currently brutalizing his bitch-hole.

"Bounce for me."

Danny desperately humped his ass back onto the rigid spear between Ornella's legs, his cheeks clapping against her belly as he endeavored to match her rhythm and help her reshape his insides. Her iron meatbar penetrated Danny with steady, deliberate thrusts, functioning like a piston designed to feminize the boy's ass into a pussy. Ornella continued to fuck him doggystyle but shifted her body so that she could step on his face, locking him into position while she otherwise maintained a firm grip on his hips. Danny enthusiastically licked the sole of her stocking-covered foot while she pillaged his taut body from behind, huffing in the odor that she smeared across his features.

FWAP, FWAP, FWAP, FWAP, FWAP...

"Yeaaahh...now squeeze that butt like I taught you," Ornella cooed as she methodically long-dicked Danny into a daze. The metronome sound of his ass clapping was occasionally interrupted by shameful, squelching farts when air escaped his hole, or by insuppressible beta moans when Ornella's head found Danny's prostate. She admired the obscene sight of her shaft's length emerging--seemingly impossibly--from Danny's ass in between thrusts, each time retracting fully to the tip before plunging back down to the hilt. Danny dutifully attempted to clench his hole for Ornella, earning a few appreciative spanks in return.

"Gooood boy! You've gotten pretty good at that," she grunted through gritted teeth while sodomizing the slut on her couch. "Really though, this is some grade-A fag pussy, the fucking grip... you were built for this, you know that? Aren't you glad we found your calling?"

"Unghh... yessss ma'am... thank youuuu..." Danny groaned with a muffled voice, his face still pressed firmly against the couch by her foot. Ornella planted into Danny for a few moments, addicted to the sight of her monstrous schlong disappearing into the twink's slender body.

SCHLAP, SCHLICK, SCHLAP...

"You could probably become famous if we started making porn, with how popular all that femboy, sissy stuff is right now... What do you think? Feels like a waste not showing off an ass this talented. Although this shit might be too hardcore for the mainstream. It's kind of nasty, really, watching your hole suck me in and out. But hey, there are always freaks out there, who am I to judge."