The Games the Gilf Plays

NOTE: This is another in an ongoing series of stories involving horny older women playing devious sexual games with younger men and/or women. These won't be connected, though some may be, and are meant to stand-alone individual stories in a themed series. Thanks and enjoy.

*****

Gloria Thibeault drummed her fingers on her desk, waiting. She didn't like to be kept waiting. Ever.

Gloria was one of the most powerful women in Massachusetts, running a high-profile software company in Boston from an office tower built by her company housing other firms paying high rent. Hers was the best office at her headquarters on the top floor, a lofty location fitting the style of a woman routinely on lists of the country's most powerful women.

It was a corner office, the walls of floor-to-ceiling glass affording stunning views of the city, the harbor, and on clear days, all the way into southern New Hampshire.

It took a lot of hard work over decades of a career that was long ago mired in the good-old boy machinations of a men's-only world.

She'd made it big, and as a result, could put her finger on anything – or anyone – she wanted. Now the 68-year-old blonde beauty sat in her office, waiting, looking devastatingly gorgeous in her expensive, smart gray business suit with matching slacks and jacket, black blouse beneath and high heeled leather boots, loose fitting and extending a quarter way up the firm sexy legs beneath her pants.

"Has she arrived yet?" Gloria growled impatiently into the intercom.

"No, Mrs. Thibeault, not yet," said her secretary, nervously, even after many years under the employ of 'The Dragon Lady', as she was known in the company, a name the boss lived up to and loved. "I'll send her in the second she arrives."

She'd sent for Jamie Condon, an underling, a pretty little 25-year-old in accounting that had been working for the company since graduating college and had a report Gloria wanted to discuss. It had been done quickly and shoddily in the boss's estimation and the boss's estimation is all that mattered.

Gloria clicked off the intercom, drumming her fingers on the desk again. She felt her body tense beneath her expensive clothes, a body tall and lean and trim, five-feet-eight inches in height, encompassing a sinewy and strong 130 pounds. She worked out constantly, when not on the job, and it showed in a body the envy of women half her age.

"Bitch," she snarled to herself, picking up Jamie's report and flipping angrily through it.

Seconds later, the door creaked open. Jamie shyly stuck her head inside, eyes filled with fear. She'd heard things about Mrs. Thibeault, bad things about how The Dragon Lady treated her employees, particularly newer, inexperienced ones. She wasn't looking forward to this.

"Mrs. Thibeault?" Jamie said weakly, clutching her purse up to her chest. "May I come in?"

"Stupid question, I sent for you didn't I?" Gloria snapped. "Get in here."

Jamie shuffled in nervously. She wasn't crazy about her job, but knew success in it would be a stepping stone to administration, either at this company or another.

Gloria eyed the pathetic creature inching her way toward her huge desk by the window, Boston's skyline gleaming behind her. Jamie was a short girl, with long dark hair pulled into a ponytail, wearing clothes of poor quality and ill fit, a black skirt and matching jacket, white blouse and sensible dark shoes with sheer pantyhose.

Gloria watched her shuffle to the chair before her desk, purposely crafted lower than usual to put the boss on a higher level, symbolizing her superiority over anyone sitting in it. She motioned with her head to sit, and Jamie quietly obeyed, legs crossed politely at the ankles, hands over her knees, together.

She scrambled in the purse on her lap, pulling out tissue from a small package near her cell phone, hoping she wouldn't need it. She kept her head down, not wanting to get into Mrs. Thibeault's laser line of vision.

"This is crap, young lady, and I think you know it," she snapped, slamming the report down on the desk, startling Jamie and glaring at her, her pretty and somewhat wrinkled face framed by her impeccably coifed shoulder-length blonde hair, green eyes flashing in anger.

"I'm...I'm sorry, Mrs. Thibeault...I did my...I tried...I worked late that night and..." Jamie stammered.

"Look at me when speaking to me!"

Jamie looked up into the gorgeous but angry face and noted her equine features, long face, chiseled and firm, with a slight jutting jaw that contributed to her overall dominant mien.

"Yes...Mrs. Thibeault," Jamie warbled in quavering voice, her own eyes watering slightly, staring into her purse.

"I don't think your excuse is in that cheap pocketbook you're staring into, young lady," she snarled. "Put it on the floor!"

Jamie obeyed, retaining a clump of tissue in her shaking hands and dabbing at her eyes.

"I don't give a damn how late you worked, how it meant you couldn't have dinner with your boyfriend or husband or girlfriends or whatever, I just don't give a good god DAMN, do you understand!" Mrs. Thibeault growled in a cutting voice. "You work for ME, you do good work for ME, or you're gone! Do you understand that?"

"Yes, Mrs. Thibeault, yes, of course, I tried to do good..."

"SHUT UP!"

Jamie did, gulping hard, feeling the bile rise in her throat.

"Now, little girl, what are we going to do about this?" Mrs. Thibeault said more quietly, leaning on her desk and forward, staring at the frightened waif trembling in her chair.

"I...I'll do the report again, Mrs. Thibeault, right now, I'll go back to my cubicle and I'll..."

"No, you will not," she snarled. "You get no second chances here. Consider yourself fired."

Jamie's eyes welled up more, a single tear running from one eye and down her smooth cheek. She blinked it away, her mouth open, her expression one of plaintive disbelief.

Gloria let it sink it, let Jamie squirm, let her try to form some words of begging to keep her job, let her fear all hope was lost, before she added a single word.

"Unless."

Jamie cocked her head.

"Unless?"

"Unless," Gloria said, her slightly puckered mouth curling into a slight almost imperceptible smile. "You do as you're told."

Jamie blinked, her mind racing, trying to figure out what she meant. She couldn't, and her expression remained quizzical, much to the boss's delight. Her mouth moved into even more of a smile, something rarely seen around the office.

"Do you want to keep your job, young lady?" she asked.

"Yes, yes of course!" Jamie said excitedly.

"Then you'll do exactly as I tell you, won't you?"

"Yes, Mrs. Thibeault, of course, what is it?" Jamie asked excitedly, eager to keep her low-paying, high-hour job and get out of the dragon's den in one piece.

Gloria sat back, slowly, and then raised her legs up, plopping her feet on the desk, hanging them near the edge. Jamie looked at those boots, and the slight glimpse of shiny tanned shin above them as Gloria's pants rode up slightly. She knew those boots, she knew how expensive they were and something she could never afford on her meager salary.

She looked at her boss, more quizzically than ever. Gloria sat back in her huge leather chair, hands behind her pretty head, locked together. She motioned toward her boots.

"Lick them," she said.

Jamie blinked. She couldn't mean what she just said, she thought.

"I'm sorry?" she said in a weak tone.

"So you're deaf as well as dumb, is that it?" Gloria snapped, thumping her boots on the desk, Jamie's eyes drawn to them, the exquisite soft black leather, the high arch, the long, sleek heels. "I said lick them. My boots. THESE boots, you stupid bitch!"

She thumped them on the desk again.

"If I have to repeat myself a third time, you can just get up and leave, you're through," she growled. "Now, what will it be?"

"You want me...to lick...your boots?" Jamie asked slowly.

"Very good, now we're getting somewhere," Gloria said with a fake smile that quickly morphed into a condescending sneer. "Yes, I want you to lick my boots – and anything else I want licked! Do you understand?"

"Anything...else?" Jamie said, mind awash with implications of this, trying to formulate a way out and still keep her job. "Like...what?"

"Oh, my GOD, you are so fucking stupid!" Gloria barked. "My pussy, my ass, my tits, even my fucking sweaty armpits if I want! Is that clear enough? Do you want to keep your shitty job or not?"

"But Mrs. Thibeault!" Jamie cried out, suddenly finding a voice. "That's..that's not just sexual harassment, that's extortion!"

Now a full smile broke out on Mrs. Thibeault's lips.

"Precisely, it's sexual harassment AND extortion!" she laughed. "Sexual extortion, in fact. And believe me, you prissy little twat, I'm quite good at it."

"You..you've done this before...forced employees to have...to do things, sexual things?" Jamie gasped.

"Yes I have," Mrs. Thibeault said with perverse pride. "Women AND men!"

She watched Jamie squirm, loving her unease.

"Well?" she hissed. "These boots aren't gonna lick themselves!"

Jamie looked at her, then the boots. She knew she had to do what she had to do to survive. She shuffled off the chair on her knees, to the boots. She inhaled. The smell of fine leather was heady, sensual. She delicately planted a kiss on the toe of each one.

"Like ya mean it, bitch," Mrs. Thibeault snapped angrily. "I said LICK my boots, not kiss!"

Jamie let the tears flow with neither the need or ability to hide her emotions now, and scrunched up her eyes as she slathered up and down the boss lady's boots, from the toe to instep, around the side, her tongue brushing the tops and tasting the salt of her exposed shins.

Down she went to the bottom, the slight grit of the soles tainting her slavish tongues, then the heels, those long, pointy spikes. She opened her mouth and sucked each one inside, eyes still closed, feeling the long, strong legs trembling, the tremors of them running into the stiletto heels.

"Mmmm that is nice, so nice, suck 'em bitch, suck 'em like you suck your boyfriend's cock!" Mrs. Thibeault growled in a gravely low voice. "If you have a boyfriend! Maybe a girlfriend! No, can't be that, you definitely don't like what you're doing to me, so you can't be a dyke!"

She cackled, a demeaning harsh laugh as Jamie continued to worship her boots. She then slowly pulled up each pant leg, exposing those long, fairly well muscled calves, tanned and firm, freckled and flexing.

"Lick my shins, each one, up and down, I love my legs licked," she cooed playfully as Jamie obeyed, running her tongue up the bone of each smooth, hard leg. "Now my calves..."

She plunked both legs on Jamie's shoulders. The startled girl looked side to side at them, marveling at the silkiness of them, the defined muscles beneath the sleek skin. She gulped and darted her tongue out to the left calf, lapping at it, then the other. Mrs. Thibeault grinned like a madwoman watching, tensing her leg, making the muscles in her calves ripple and flex under Jamie's trembling tongue.

"Wanna see a trick I do with these calves?"

Jamie could only nod helplessly, unsure of what was coming – which was Mrs. Thibeault suddenly and savagely lashing her calves together around Jamie's neck, cinching her boots together, the expensive leather creaking.

The power of her muscular lower legs caught Jamie by surprise, and the pain overcame her, then dizziness as the muscles knifed into her soft neck, compressing the arteries.

"I could fucking KILL you locked in my calves like this!" Mrs. Thibeault snarled, leaning up in her chair to look at Jamie's bluish face trapped in her punishing legs. "But I think I'll just knock your sorry ass out instead!"

And she did, squeezing with brutal severity, shutting down the blood to Jamie's brain. The girl passed out cold in the viscous scissors, and slumped to the floor. Mrs. Thibeault released her, laughing.

When Jamie awoke, it was with the boss's stinky feet in her face. She was sitting on the edge of her giant desk, having peeled off her boots and now placed her feet on Jamie's mouth and nose, feet encased in low black trouser socks.

"Had these on awhile, they smell frightful," Mrs. Thibeault barked down at her slave. "Smell 'em!"

Jamie did, blanching at the acrid, foul foot funk of them as her boss rubbed the sweaty fabric all over her face.

"Peel 'em off," Mrs. Thibeault continued. "With your teeth!"

Jamie obliged, pinching the top of each sock in her teeth, slipping the foul-smelling sock off. She lay on her back watching in horror as Mrs. Thibeault wiggled her long, painted toes at her. Her feet were long and perfectly shaped, veins criss-crossing the insteps and ankles, the soles thickly wrinkled. A slab of yellowing callous was visible on each heel.

"Lick," was all she said.

Jamie did as the feet were pressed down on her, running her tongue over the thick soles with a papery feel to them, then sucking and lapping the heels, the calloused flesh scraping her lips. The humiliation increased as Mrs. Thibeault had her kneel, crossing one leg, wiggling those long toes and spreading them.

To Jamie's horror, she saw grit and grime between each one, held in place by a day's worth of sweat.

"Suck 'em, bitch, suck your boss's toes!" Mrs. Thibeault laughed. "Suck 'em clean!"

Jamie sobbed now, ingesting each toe, one by one, tasting the foulness of them, smelling the funk between, a deeply pungent vinegary smell. As she fellated each toe, she ran her tongue around it, slipping it between the toes, pulling out the grimy residue and trying not to vomit as she ate it down.

Finally, Mrs. Thibeault pulled her feet from her mouth and stood before the crying underling, who looked up at her through wet eyes.

"Am I done?" she cried. "Is it over? Please?"

"Not hardly, bitch," Mrs. Thibeault snapped. "My pants. Take them off."

Jamie knelt up slightly to unsnap the gray slacks as Mrs. Thibeault shed her jacket, draping it over her chair. She watched Jamie's shaking hands undo her pants, then the buttons, then pulling at the waistband.

"Panties, too," Mrs. Thibeault laughed down at her. "Let's not waste time."

Jamie tugged the pants and panties down over Mrs. Thibeault's incredibly well shaped ass, over her lush and hard thighs and freshly licked feet. She gasped as she sat back, and Mrs. Thibeault kicked the pants away: Inches from her face, at eye level as she knelt, Jamie looked into a thick gray bush of pubic hair, gleaming with dewy droplets. Inside was the pucker of dark lips, gleaming wet.

The smell hit her, thick and profound, reeking of sweat and urine and uncleanliness. Mrs. Thibeault's dominant grin widened.

"Stinks, huh?" she laughed. "And bet you've never seen a hairy pussy like this before, have you? Or any pussy besides your own? Do you shave your cunt? Bet you do...but maybe we'll save that for later."

Jamie's sobbing increased as Mrs. Thibeault advanced slowly, pushing off the desk and standing before her, feet slightly spread. Jamie saw the bushy lips part, the greasy nub of her clit erect between them. The thighs wobbled as she moved, thick with fleshy muscle.

"Lick my cunt, Ms. Condon," she said, reaching for Jamie's crying head.

"Mrs. Thibeault...please...don't make me eat...lick your...please!" Jamie sobbed, pulling back against the pushing hand.

"I'm not asking, bitch!" Mrs. Thibeault roared angrily, now grabbing Jamie's dark hair in both hands and shoving her face smack into the thatch of her pussy. "EAT MY CUNT!"

The stench was worse than the humiliation, as Jamie, with her eyes forced into the brush of her cunt, had her nose enmeshed in those oily pussy lips, the smell overwhelming her, that savage mix of piss and sweat and cheese. Jamie screamed as the old woman worked her face, holding her head and pumping and grinding her snatch against it.

"I'll do some of the work, but you're doing the rest," she snarled, drawing her hips back and brutally slamming them forward to smash her aromatic pussy hard into Jamie's face.

Then she held it there, positioning the oily nub of her clit on Jamie's nose, pushing hard, grinding and pumping. Jamie felt its slime run down her nose and into her nostrils and screamed into the moist maw of the pussy beneath. She held onto the backs of Mrs. Thibeault's solid thighs for support, the flesh of it hot on her hands, feeling the hamstring muscles tense tightly against her fingers

"Eat it, bitch, suck on that pussy, stick your tongue WAY up my hole!

She had no choice as the lusty old woman held her head, dragging her face lower. Jamie's tongue slipped out of her moaning mouth, through the furry folds, penetrating the greasy lips and getting sucked out into the clenching walls of her boss's cunt. She speared it over and over, trying gamely to ignore the stinging, bitter flavor of the pussy she was trapped in as the grunting woman continued to pump her hairy cunt on the young girl's face.

"C'mon, work it bitch, work that clit now...suck on it...lick it!"

She pushed forward, now forcing Jamie to bend over backwards on the floor in her kneeling position, and trapped her completely in her heaving crotch. The entire pussy embraced her face as Mrs. Thibeault held fast to her head with one hand, the other on her hip, pumping and thrusting back and forth.

Jamie sucked and licked the greasy clit, anxious to make her cum and release her. Mrs. Thibeault's pumping and grinding grew more violent the closer she got and now she stood completely over Jamie's face, her skull imprisoned in the older woman's powerful thighs.

Jamie screamed, her back aching in the awkward position, her jawbones compressed by the grinding crush of Mrs. Thibeault's powerful, scissoring thighs. The old legs held her in place now, and Mrs. Thibeault stood straight up, hands on her hips, swiveling them and glaring down at the crying young woman trapped in her punishing thighs.

"CUMMMING!" she screamed, arching her back and pumping and thrusting her cunt into the groaning mouth, dragging her dripping gash over it.

Jamie prayed to be squeezed so hard she'd pass out, as she'd done in the calves moments before. But she only grew dizzy from the clamp of thighs and smother of pussy as Mrs. Thibeault finished off on her face. Jamie felt the thick gel of her cum sluice from the milking hole and fill her mouth. She swallowed the orgasmic goo, gulping it down, trying to ignore the gamey taste of it.

It seemed to take Mrs. Thibeault forever to finish, slowing her thrusts and now just holding Jamie in her crushing leglock, those powerful old thighs quivering.

She let go, stepping off Jamie's face. The girl slumped to the floor, her face coated with her boss's cum, sobbing at her feet.

"Oh, and one more thing, bitch," she heard her say.

Jamie looked up through watery eyes. Mrs. Thibeault was leaning on her desk. Her ass was full and fleshy and shapely for a woman her age, gleaming white and slightly dimpled, the paleness stark contrast for the rugged, tanned legs below.

"Oh my God, please, Mrs. Thibeault, please!"

The boss looked back over her shoulder. She smiled. And jiggled that ass in meaty waves, one cheek at a time.

"Twerking, is that what you ridiculous young people call this?" she laughed. "Well get over her and SUCK my twerking ass!"

She jiggled it faster and faster as Jamie approached, wiping the sticky cum from her face. She looked inside as the quivering rump stilled and Mrs. Thibeault parted the meaty white orbs with her hands. The asshole was dark and wrinkled, surrounded by strands of wet hair.

The smell hit her like a punch to the nose, musky, funky, sweaty and worse.

"Lick my asshole, slave girl!" came the command. "It needs a thorough cleaning!"