The Contest

Casey’s New Job

By Fielding J. Melish

“Oh, God, Miss Burns! Please do it HARDER! Oh, yeah….YES! YES!! God, YES!! I’m cummmmmmmmmm…inggg….!!! Casey Kelly screamed in complete and genuine ecstasy at the top of her lungs, as the thick, ten inch black dildo drove deep into her stretched and soaking pussy. Casey’s cries rang off the walls of the small studio apartment.

Sherrie Burns, Casey’s Office Manager at Hardwood Industries, squealed demonically with triumph and delight as she drove her latest lesbian conquest to the edge of orgasmic madness with her huge vibrating strap on. She leaned over Casey’s back, her torso dripping with sweat as she plunged the ebony dong deeper and deeper in to the depths of Casey’s cunt, and hissed in her ear, “I always knew you’d love it, you little dyke whore! Now tell me how much you want me to give it to you, you fucking bitch!”

“Please, Miss Burns……I WANT MORE!!…Please, PLEASE FUCK ME MORE!!! Casey could hardly believe the passionate trash talk that spewed from her mouth as she ascended to the heights of pleasure on Sherrie’s fake dick. As the latex cock thrust into her again and again, she finally, inexorably, lost control as her body exploded into an intense, cascading climax.

As Casey slowly came down off her high, Sherrie gloated over her with the mastery of her well refined sexual technique.

Sherrie finally removed the strap on and tossed it casually over the edge of her hard, narrow bed. She fell back exhausted on the soaking mattress with her head up against the plywood headboard. The lesbian Office Manager looked up at Casey and sneered, pointing to her own dripping snatch. Grabbing a handful of Casey’s flame red hair into a tight ball with her fist, she roughly dragged her subordinate’s face down to her waiting crotch while her sub cried out in helpless pain.

Sherrie laughed sadistically. “My turn now, slut-EAT me!”

An hour earlier, while making out with Sherrie on her couch, as Sherrie thrust her eager wet tongue down her throat, Casey never would have believed that being a bottom for Burns could give her this much pleasure.

Only a week ago, Casey was just another lowly little drudge of a thirty-two year old typist/file clerk in the Secretarial Pool at Hardwood. Another faceless, powerless girl who struggled to make ends meet in the New World Order of Employer’s Rights: Rights for men that gave them absolute authority over women in every aspect of life. Rights for women that had completely disappeared.

She’d been briefly infamous for nearly winning Hardwood’s First Annual Hot Legs Contest a month before, but that near victory was long forgotten as Casey once again blended into the regimen of strict discipline and endless trivial rules and abuse that was her lot as a loser in the Secretarial Pool.

She was still the pretty, girl next door redhead, with a short but tight body, a perfectly rounded ass and a new reputation for owning a great pair of legs. But she had slipped even further behind in obtaining her ultimate goal of becoming a PA since losing the contest she had schemed so hard to win.

Time marched on very quickly for girl her age with few prospects for promotion.

Every morning, Casey would see many of the over forty hags recently laid off from Hardwood, lurking outside her office building. Some had reached their mandatory retirement age without being approved for their pension; others were blacklisted for having “attitude” problems, placed on the National Employer’s Index and could no longer find work. Their faces were all coated with heavy make up and they wore obscenely short skirts, as they pathetically offered their middle aged bodies to any available male looking for a cheap lay before the work day began.

Company security routinely ignored this blatant prostitution, perhaps as a warning to the younger girls to mind their attitudes. “This could happen to you,” their leering grins seemed to say, as they walked calmly by the newly minted whores.

And in fact, this was Casey’s biggest fear. She knew she was only a few short years away from joining these aging hookers if things didn’t turn around-and fast!

One Tuesday evening after another long day of mindless busy work, Casey was lucky enough to secure a seat on the final leg of her three bus rides home. She was riding with the other female office drones returning to their overcrowded apartments, when it started to rain heavily. The vehicle quickly filled up with a group of young high school boys. They were loud, crude and sweaty, probably returning home from a soccer practice. As the empty seats became scarce, the surly boys began to glare at her. She groaned silently to herself, but knew the law. Reluctantly, she gave up her seat to a brash boy and the pimply faced adolescent quickly jumped to take her place.

The bus was overcrowded now, and Casey was forced to stand next to the boys, while they leered at her and made obscene comments. She tried not to make eye contact with them, but every few seconds, she felt an adolescent hand groping her ass, or copping a feel of her leg, beneath her coat. Every time she turned to confront the culprit and protest, a tall, gangly boy of about sixteen would flash a nasty grin at her and his hand would disappear instantly back into a jacket pocket. As soon as she looked away, she’d feel the hand on her ass once more and hear the muffled sniggers from his teenage friends.

Frustrated and tired, she finally turned and shouted at him, “Quit groping me young man!”

The boy looked straight at her and spat back sarcastically, “I bet you get ‘groped’ a lot, Honey- Bet ya like it too!” All the boys gave each other high fives and laughed hysterically. Casey knew better than to protest too much and prayed for her stop to come. After an eternity of more molestation from those kids, she finally got off the bus.

As she walked the last four blocks home in a pouring rain she finally formed an idea that might get her a little relief, at least at the office. At this point, she was ready to try almost anything.

Sherrie “The Enforcer” Burns was her Office Manager at Hardwood. She was very beautiful on the outside, but a true Bull Dyke at heart. Sherrie brutally ruled the Secretarial Pool staff with an iron hand. Even the slightest infraction of the rules, would bring a stinging, public spanking, with the errant girl forced to pull her panties down to her ankles as Sherrie whacked her time and again with a thick metal ruler that was her constant companion. She always gave the bosses a great show and this enhanced her status as office Nazi.

Sherrie had once hit on her, but Casey was straight and foolishly let Sherrie know she didn’t enjoy the oral sex Sherrie performed on her during one of her infamous “chats” in the copy room.

Since that day, Sherrie made life miserable for Casey. Not a day went by when Sherrie didn’t try to intimidate her by tricking her into breaking a new rule and threaten her with punishment.

It was only Casey’s constant and vigorous adherence to every rule that kept her from feeling the pain and humiliation of a Sherrie whipping.

But the tension was getting to Casey.

Although she feared and hated Burns, her life’s disappointments were giving her a “what the hell” attitude. If sucking up to Sherrie would make her life a little easier and take the pressure off just a little bit, she was ready to do things she would never had considered before.

Besides, as she remembered many pleasures with her roommate, Brit, a little girl/girl action occasionally really wasn’t all that bad.

Finally, exhausted and soaking wet, Casey made it through the front door of the cramped one bedroom apartment she shared with her roommates, Brit and Sally. All she wanted was to flop down on the threadbare old living room sofa, but she was disturbed by the sounds of loud grunts, and the creaking of rusty mattress springs coming from the direction of their one tiny bedroom. Casey was about to investigate when the reason for the noise became apparent.

Emerging from the room was roommate Brit and the obnoxious Mr. McCurdy, the married manager Brit was dating. McCurdy was forty nine and at least thirty pounds overweight. His balding head sported a bad comb over, and he wore thick black glasses with coke bottle lenses on the nose of his pockmarked face. Before the new laws took effect, no girl would ever consider giving him a second look. Now, he had his pick of attractive girls, powerless to resist his advances without fear of losing their livelihoods.

Assistant Engineering Manager at Hardwood, McCurdy spoke with a slight lisp and had an unpleasant, aggressive personality. He was about five inches shorter than the statuesque Brit- a stark contrast to the busty, platinum blond beauty with her long legs, full, sensuous lips and fashion model features.

McCurdy was infamous for forcing himself on helpless office girls and had dangled the prospect of a PA position in Brit’s face along with the threat of termination to give her extra incentive to see him outside of work.

Now, he was obviously a little tipsy and his tie was hanging loosely from his collar while he grabbed Brit possessively with one fat fingered paw around her thin waist. His glasses were askew, his cheek was smudged with lipstick and his fly was wide open. He wore a satisfied smile and looked immensely pleased with himself. No need to guess what the noise from the bedroom was all about.

As for Brit, she was trying frantically to button her torn blouse and pull down her dress that was hiked up around her shapely hips, making a futile attempt to pull herself together after the couple’s recent session on the bed.

McCurdy grasped Brit’s pink panties as a trophy in one hand and with the other, dragged Brit to the old sofa. He pushed her down and continued to feel her up as Brit tried to look pleased and satisfied.

“Hey roomie,” Said McCurdy smugly when he spotted Casey. “Wanna join us sweetie?” He laughed rudely while nibbling Brit’s ear and Casey declined. “We were just leaving anyway, weren’t we baby?” He stroked Brit’s stocking clad legs, and then reached higher to play with her bare crotch, disregarding Casey’s presence in the room. “Tell your cutie roommate where we’re headed Brit”

Brit looked at Casey with total embarrassment but still used one hand to caress McCurdy’s groin area as he demanded.

“Yes, Sir.” She looked right at Casey. “Mr. McCurdy and I are going to amateur night at the Cheetah III so that I can dance tonight.” She assumed her bimbo role, with a forced, happy smile on her gorgeous face.

The Cheetah III was a notorious sleazy strip club downtown where all the married managers took their dates from the office.

“Go on baby, tell her why,” McCurdy giggled, highly amused with himself.

Brit looked directly at Casey and forced herself to say the words McCurdy obviously ordered her to repeat.  “Mr. McCurdy says that my tits are so nice, I should share them with everyone!”

McCurdy roared with laughter at this and squeezed one of Brit’s big boobs. Casey was embarrassed for Brit, but for her sake, smiled politely and turned toward the bedroom to change her clothes. McCurdy suddenly pulled Brit off the sofa and as they neared the door, the nasty Manager blocked Casey’s path, pinning her against he wall with his bulk.

“Maybe we can make it a threesome tonight cutie.” He spit into Casey’s face with his annoying lisp, and then grabbed her hand with an iron grip, forcing her to feel his growing erection.

Casey kept her cool and smiled sweetly as she gently pulled her hand away from the pig. “Yes, Sir, that would be very nice, but I have a date tonight,” she lied. “Maybe some other time, Sir.”

McCurdy just grunted and Casey shivered with disgust as he and Brit stumbled out the door.

Casey went to work the next day determined to change things with Sherrie, but working the bitchy Office Manager wasn’t going to be easy because of Casey’s past rejection of her advances and Sherrie’s naturally suspicious nature. 

Each day at work, Casey attempted to pique Sherrie’s interest by finding some excuse to speak with her or make some kind of bodily contact, until Sherrie got the idea that Casey was definitely interested in a second go round. At first, Sherrie, was her usual sarcastic and caustic self, reacting to any initiation of conversation by Casey with a hasty rebuke and implied threat of punishment.

But little by little, Casey began to patiently make some progress, thawing Sherrie out.

She might subtly brush up against her at the water cooler, and ask for advice on movies with lesbian themes. Or she would ask for Sherrie’s help in straightening a stocking.

On afternoon, just before one of her mandatory “stress relief” masturbation sessions, Casey asked Sherrie for her advice on the best sex toys to get off on, and with a sly wink, Casey also inquired if Sherrie would be kind enough to “show” her how to use them properly some day.

Finally, about three weeks into this daily seductive dance, Sherrie came around Casey’s station on the pretext of checking if her skirt was regulation length. They both knew it was, but it gave Sherrie a convenient excuse to feel Casey up a bit and see if her new found girl lust was genuine.

“Thanks so much, Miss Burns.” Casey would say in her best Marilyn Monroe bimbo voice. “Your hands feel soooo good!” Burns stopped to look in her eyes with a quizzical look.

“Oh, I know we didn’t hit it off right at first Miss Burns,” Casey continued as she sensed the opening. “But lately, you’ve been in my thoughts a lot.” She whispered this right into Sherrie’s ear as she leaned forward, touching her lobe with the tip of her tongue as Sherrie felt up her stocking leg.

“I know this is a little impudent, Miss Burns,” Casey quickly added, “but I really was hoping we could have another ‘chat’ in the copy room some day.”

Sherrie was very cautious, but curious. Lust got the better of her and she took the bait.

“Maybe we can do better than that Kelly.” The way she said this gave Casey an uneasy feeling, but she feigned excitement and giggled happily.

Sherrie grabbed a post it note from Casey’s desk and scribbled something with a pencil.

“Here’s my address, Kelly. Why don’t you come on over for a little visit tomorrow night, say around eight.” Then she as she turned on her heels and strutted away, “wear something pretty for me.”

Four long nights later, after taking Sherrie’s huge black dildo up her butt and being forced to please the insatiable Office Manager with her lips and tongue, Sherrie finally began to warm up to Casey.

One evening after a particularly intense session of oral sex that left Casey with an aching jaw, she confessed to Sherrie that she had always hoped for a PA interview.

Sherrie caressed her hair with a touch that was almost tender. “Don’t worry Kelly, something might turn up yet.”

Then the moment was gone as she pulled Casey’s head back to her pussy. “Now get back to work licking my cunt!”

A week later, the big break she prayed for finally came.

Casey walked confidently down the west wing of the office. She still could hardly believe her good fortune and wanted to pinch herself, but this was reality. She was about to enter the office of Howard Finnegan in Human Resources and interview for a position as his new PA!

Only yesterday, Sherrie Burns had walked over to her station with the urgent message: Mr. Finnegan in Human Resources had specifically requested Casey for an interview!

It took Casey a long evening of performing exhausting oral sex on the insatiable Sherrie Burns until her jaw was nearly paralyzed, to discover that several managers had recently expressed interest in Casey, but Sherrie had always implied that Casey had “an attitude problem”, and scared them off.

Now, with their new relationship, Sherrie put in a good word when the next PA position came open and implied to Finnegan that Casey was not only really hot but would do absolutely anything to please him.

Finnegan was very important in the company and on his way up the corporate hierarchy.  Only forty two, he was very handsome; over six foot three with a full head of jet black hair, and dazzling white teeth that he displayed in a broad, welcoming smile. He was in excellent, even “buff” physical condition.

Finnegan was still single, looking for that perfect “Trophy Wife” to advance his career. Even better to Casey, he had a reputation for being very polite and well mannered. He was known to have slept with more than a dozen girls in the Secretarial Pool and anyone of them would be thrilled to work under him.

This was a dream job for Casey and she wanted desperately to make a great impression and nail the interview.

Casey made certain to wear her sexiest skirt, underwear and nylons for her interview. Her makeup was flawless with a liberal coating of bright red lip gloss, well applied blue eye shadow to set off her big blue eyes and large gold hoop earrings.

Finnegan smiled warmly as he ushered Casey into his spacious office. He relaxed in his leather executive chair. Behind him, was a long rectangular mirror that nearly covered the entire back wall of the room. He invited Casey to be seated while he went back to shuffling some papers for several long minutes. Finally he looked up and carefully regarded her.

Casey expected the usual: to be ordered to remove her blouse and bra for breast inspection and then allow Finnegan to feel her ass or legs as he saw fit. Perhaps he would demand a blow job that Casey was very prepared to perform.

But he did none of that to Casey’s great surprise and almost disappointment. Instead, he merely said, “Guess you’ll do fine,” and went back to shuffling his papers. “You’re hired. Report to my office tomorrow morning. Panty inspection at nine sharp around here.”

Casey was happily stunned!

“Yes, Sir, Mr. Finnegan!” She gushed. Her dream was at hand! More money, prestige and maybe even a shot at becoming a Trophy Wife, were now within her grasp.

“I want you to know Sir, that you’ll be very pleased with my…..”

He held up one hand to interrupt. “Yes, yes… I’m sure I will. Dismissed, Casey.”

Casey knew better than to speak again to her new boss, and stood to walk out the door.

As she prepared to leave and cheerfully gather her things at her old work station, Finnegan abruptly spoke again and she stopped in her tracks to turn around and face him.

“One more thing Casey,” he added softly.

“We’re having Take Your Son to Work Day at Hardwood tomorrow. I’ve decided to invite my nephew, Steven, to assume my managerial duties for the day. The boys won’t have any real authority in business matters, but they need to learn how to control the staff when they become managers after graduation. They’ll have full authority over anyone working under us, including our PA’s, so Steven will be your new boss while I’m on a brief business trip. I expect you’ll obey all his orders without question.”

Casey was a little perplexed, but addressed this concept quickly. “Yes, Sir, I understand completely Mr. Finnegan. I’ll be certain to follow all his instructions to the letter!”

“Good girl, Casey. Now you may leave.”

Casey exited the office of her new boss and walked back to her old station with great satisfaction. Her plan had worked to perfection.

The next morning, she arrived at Hardwood, excited to begin her new position. She didn’t quite know what to expect, having a young kid as her boss for her very first day as PA, but thought it was a pretty harmless idea.

She walked briskly into Finnegan’s’ office at eight thirty and prepared to make coffee and get acquainted with her new routine. Before she could fill a pot with water, she was totally shocked by the sight of the person now seated comfortably in Finnegan’s executive chair.

Leaning back with arms folded behind his neck, wearing a new pinstriped suit and a world class smirk, was that nasty high school boy from the bus ride home. The same kid who had molested her.

“You’re Mr. Finnegan’s nephew!!??” Casey shouted in dread, totally forgetting her place.

“That’s right, honey,” he sneered, “And by the way, it’s ‘Sir’ to you!”

Casey forced herself to regain her composure. “Yes, yes…Sir,” she stammered. “It’s just that I…..I mean…”

“I’m Steven.” Said the gangly sixteen year old. “My uncle tells me you’re my new PA today. Why don’t we get to know each other a little better?”  He stared into Casey’s eyes and his voice assumed a more ominous tone. “Now lose the blouse right now and let me see your tits!”

For a moment Casey froze. At first, her mind reeled and she didn’t know what to do. But years of conditioning from obeying every command from lust crazed superiors took hold and she reflexively loosened the buttons of her freshly cleaned white blouse.

Steven gleamed like a kid in a candy store as Casey slowly removed her blouse and set it aside on the chair. She hesitated once more as the intern stood up and approached her, very pleased with his new found authority.

As Steven circled slowly behind her like a predator, Casey just stared straight ahead and fumbled to unhook her black lace push up bra that allowed her smallish breasts to spill into view. She attempted to cover them with her hands, embarrassed to be naked in front of a mere child.

The boy stood directly behind her and folded his arms across his chest, acting like the boss he thought he was. He would have none of this. “Put your arms down!” He ordered and she obeyed.

“Kinda small ain’t they?” He laughed. “I seen better tits in my magazines every day. Well, guess we can still have some fun anyway.” He suddenly grabbed her breasts from behind with both hands and roughly squeezed her puffy red nipples.

“Uncle Howie says I gotta learn the ropes. Says I need to control my staff. You wanna be controlled Casey?” He continued to pinch her nipples, rolling them with his thumbs then digging into her with sharp nails until she squealed in pain.

“Please Sir, It’s my first day,” she almost cried with the agony. “…I want to follow your instructions, but….”

The young bully was puffed up with a feeling of power. He shoved her brutally in the back so that she collapsed chest first onto Finnegan’s massive desk, her bare tits splayed on the glass top. The boy pulled Casey’s tight miniskirt up to her waist to expose the sheer black panties and lacy garter belt she wore.

“Wow!” He exclaimed, all lusty high school kid now as he ogled her firm, round ass and well toned legs. “Love your panties and stockings!” Steven fondled her butt with one eager hand and used his other hand to slide his fingers along the edge of Casey’s smooth pussy.

“Let’s get a better look at your snatch, shall we?” He pinned her against the desk with his weight and began rubbing his hardening cock against her ass in a humping motion while he fingered her pussy. Steven then tugged at her panties and urgently pulled them down until they were bunched around Casey’s ankles.

He leaned over and whispered in Casey’s ear as he spread her legs with his own knees. “You’re getting me all hard, honey. How about a little blow job for your new boss to start his day right?”

He pulled her arms so that she spun around to face him. With a wicked grin, Steven placed his hand on top of her red hair and pushed her downward.

“On your knees bitch and suck me off!” He demanded.

Dazed and startled, Casey had no choice but to obey. She closed her eyes and as she sank to her knees, and willed herself to find the zipper of the youngster’s trousers.

In that instant, the door to Finnegan’s office flew open and Mr. Finnegan himself burst inside! He was waving his hands and laughing hysterically. Casey was completely speechless wondering what the hell was going on.

“That’s enough, Steven!” Finnegan shouted, just as Casey was about to release the boy’s randy teenage dick from his pants.

The boy turned around swiftly and angrily. “Awww, Uncle Howie, it was just getting good and I’m so horny now!” He protested loudly and stamped his feet on the floor as if he were just a petulant little boy.

“Don’t worry, kid,” said Finnegan as he approached the pair. He draped a fatherly arm around the boy’s shoulders as Steven calmed down and Casey remained bewildered on her knees. “Go see Burns,” he said kindly. “She’ll hook you up with someone from the Secretarial Pool to take care of your rod.”

Finnegan pointed down at Casey. “This PA is my property now.”

In another moment, the boy reluctantly zipped back up and sulked off, his shoulders slumping. He was obviously disappointed in the interruption of his entertainment.

Casey remained frozen where she was. Finnegan smiled at her as the boy left.

“The boy’s just a little frisky, no harm done. Some of my fellow managers and I have been watching you Casey,” he said still giggling, as if her near rape was all just innocent fun. He pointed to the huge glass behind his desk that Casey now guessed was really a two way mirror. “Wanted to see if you really were ready to do anything to please. You gave us all a good laugh!”

Casey looked up and saw the vile Mr. McCurdy and two other managers standing and chuckling in the doorway of Finnegan’s office. They nudged each other and then disappeared.

Casey was relieved and began to rise from the floor. Finnegan stopped her with his hand.

“Not so fast girl. Seeing as this is your first day, why don’t we have your orientation right here?”

Finnegan then unzipped his own pants and began stroking a very long and swiftly expanding erection.

A few minutes later, as Casey finished swollowing her first load of Mr. Finnegan’s semen, her new boss looked her in the eye and said seriously, “Well Casey, you’ve just learned your most important lesson as my new PA.”

“What’s that, Sir?” Casey gulped as Finnegan’s thick cream rolled down her throat.

Finnegan sighed contentedly.

“Never send a boy to do a man’s job!”