A Hundred Thousand Years of Pussy

"Ready?" Gail Appleton, the head of the company's training department asked the young executive, sliding into the seat next to him. A little too close.

Normally, Jack Price, the twenty-five year-old rising star in the home office of one of the largest retail chain's in the nation would have been about as ready for this individual training session as he would be for a root canal or a colonoscopy. But, when he saw today's attire donned by the attractive, reed-thin forty-six year-old training director, he suddenly had an interest in learning all about the new Stock-Keeping Unit software.

Jack was making the rounds in the operations divisions within the organization, six months in one position at a time, as part of the master plan to facilitate his meteoric rise to the top of the management chart, to learn each department's function first-hand, with the idea that he would be ultimately responsible for each of them in the not-too-distant future.

Jack was also making the rounds among the many nubile young lasses in the company, whose employee base was about eighty percent female. Being a young, handsome, single male in a company with such a disproportionate number of sexy, college-educated, available females was perhaps the best perk of this gig.

Jack had some knowledge about Gail's own reputation for enjoying a company cock or two. He had witnessed her, as had dozens of other employees, practically rape Tom Corcoran at the company picnic a few months ago, playing tonsil hockey and a rousing game of Bump The Pelvises, clothes on, albeit, at least at the picnic. And it was no secret that Gail had a long-standing on-again, off-again affair with the company CEO, Tim Rittenhouse. Rumor had it that Gail had enough goods on Tim to keep her duly and safely employed for as long as she wanted to remain so.

Which left Gail more than a little leeway to pursue some fresh, younger cock. And she had her eyes set right on Jack. Gail had heard through the very fertile company grapevine that not only had Jack been dipping his pen in the company ink with regularity, but apparently he had quite the implement.

Gail was not a natural beauty by any means, and their age difference did not make her instantly attractive to Jack, especially since he had so many other vernal options, but there wasn't any argument that Gail had the tight, athletic body of a woman half her age.

Gail was a marathon runner, and a legend in the company exercise room for her sessions on the treadmill. Nobody could go with more endurance than Gail, rumor had it, both in the gym and in the bedroom. She may have been way in the back of the line when God was handing out tits, but her toned legs, tummy, and ass were worthy of a cover girl for 'Fit' magazine.

And today, those tanned, sculpted legs were encased in a short miniskirt that was molded to her taut hips in a manner that walked the tightrope between 'acceptable' and 'risque' in the company's "Proper Business Dress" handbook.

And that was why Jack answered, without false enthusiasm, "Ready!" when Gail sidled in close, real close, for their two-and-a-half hour personal assembly in Jack's office, located just off of the loading dock, in a separate building from the main office across the street.

Jack had admittedly been curious why Gail had scheduled this get-together in the somewhat cramped and rather secluded confines of his office, and more so, why Gail had not delegated this task for his individualized training to one of her many minions.

In the next several hours, he was about to find out. He was going to experience the talents of a master trainer.

Immediately upon sitting down in front of his computer, Gail moved her chair next to Jack's, so that their legs had no choice but to touch under his desk.

Jack glanced a bit apprehensively toward his outer office, where the only other occupant of this entire section of the distribution center was his elderly assistant, Jean. Jean was approaching retirement, and was now working reduced weekly hours, which meant that she departed daily at three o'clock, leaving Jack by his lonesome for the remainder of each afternoon.

Jack enjoyed the solitude, it gave him a chance to catch up on his daily chores without the constant interruptions of buyers clamoring for their merchandise, since the outer door was locked up promptly when Jean left each day.

Jack couldn't help but to look down and get distracted by Gail's bare legs rubbing against his own, the tops of her thigh-high stockings protruding more visibly each time she shifted in her chair, which was often. jack had to squirm himself when his bulge started to become more prominent. For a forty-six year-old woman, Jack had to admit, those were some pretty fucking incredible gams.

With each correct response that Jack made to Gail's direction, she patted him softly on his thigh, each tap getting imperceptibly higher. About thirty minutes into the session, Jean poked her head into the office, and though she thought it a bit odd that the pair were arranged so snugly, Jean had been around long enough to know that the "See No Evil" edict was a good way to survive in the company for forty-one years. Besides, Jean reasoned, if she were twenty years younger, like Gail, she would have been under Jack's desk twice daily herself.

"I'll be leaving in a half-hour, boss," she called in to the young exec. "So if ya need anything before today ends, give me a holler, OK?" That was Jean's way of telling Jack, "I'm not going to bother you, and I don't want to know what's happening in there." Jean was good that way, Jack thought. She was like Sergeant Schultz in the old Hogan's Heroes show, she saw NOTHING.

"Thanks, Jean, we'll be just fine, I'm trying to concentrate, so just lock it up when you go!"

Jean gave the hairy eyebrow to the training director before she turned to leave. 'Oh, to be a fly on the wall for this one', she thought to herself. 'The spider weaves a cunning web'.

As Gail heard Jean's shoes clacking on the tile floors in the outer office, signaling her return to her chair, Gail reached behind her back and began to fumble at a spot below her shoulder blades."God damn, it's hot back here, I don't know how you can stand it, I'd want to take my clothes off if I could." Gail's voice was just low enough so that Jean could not hear her in the other room.

Jack was only vaguely paying attention as she fidgeted and whined, his eyes were riveted to the computer screen. Until he saw it out of the corner of his eye. Gail's lacy bra was snaking through the arm holes of her silk deep-blue blouse, and she was tugging on it, coaxing it to freedom like a kitten caught in a gopher hole.

"Aaah, that's better, much better." Gail heaved an exaggerated sigh of relief as Jack's eyes nearly popped from their sockets. Gail opened up the top drawer on Jack's desk and stuffed the garment inside. "So.....where were we?" she asked with doe-eyed innocence.

The next ten minutes proceeded without incident, and Jack wasn't sure whether to be relieved or disappointed. He was doing his utmost to ignore the curious removal of one of Gail's undergarments, writing it off as just a quirk of the sometimes unpredictable training czar, and tried to focus on the task at hand.

'If I don't say anything about it, well, maybe it never happened," Jack thought, not believing his own attempt at rationalization for a second, especially since Gail's fingers kept easing up his leg, now perilously close to his crotch, which was twitching like a windmill in a brisk wind.

He heard Gail's voice, her mouth now grazing his ear. "Is it just me, or is it getting really fucking hot in here?" She raised her hips off the leather seat of the chair, and wriggled her butt, placing her hands under the hem of her painted-on skirt, exposing the seams of the lacy stockings, and then, to Jack's astonishment, she produced a microscopic piece of black fabric that jack deduced must have been serving as a thong. Gail yawned and pressed the tiny triangle into the same top drawer that now housed her bra.

Jack's big, raging dick could have banged the keyboard hands-free now, this was cruel, fucking torture. But it got worse. Or better, depending on one's perspective. Gail looked at Jack with unbridled lust, there was no duplicity in her actions. "Are you hot, too, Jack?" Gail purred.

Not waiting for a reply, Gail leaned down and unzipped Jack's zipper on his trousers before he knew what hit him, and felt Gail's warm, long, manicured fingers start to extract his cock from his briefs. She pulled it out with two determined yanks, not bothering to loosen jack's belt, and he yelped a bit at her maneuver.

Before he could say anything, Gail lowered her head and began to suck softly, slowly, on Jack's throbbing cock head.

"Jamie Ellis, right?" Jack looked down at Gail, confused. 'What did she have to do with anything?' he thought. 'The coat buyer?'

Gail smiled up at him while stroking Jack's big dick leisurely, as if she were twirling a Sharpie. A very, thick Sharpie. "You fucked her, right? What was it, last week, two weeks ago, maybe?" Gail's head descended to his lap once more and she took two more, slow, long, licks. "And Carol Young?"

Gail continued the interrogation, like a good attorney, one who just happened to be a world-class cocksucker, also, knowing full well the answers to each of her inquiries. Each time Gail name-dropped a woman who was one of Jack's conquests, she sucked on his cock for about twenty seconds, her mouth releasing with an audible 'POP' each time she came up for air.

"Leslie Bobman? Kim Morgan? Ann Malley? Barbara McDevitt?"

With that last one, Gail raised her head and smirked up at Jack, a strand of saliva extending from her mouth to his purple, engorged cockhead. "Truth be told, I wouldn't mind fucking Barbie McDevitt myself, mmmmm."

Just as jack was convinced he was about to explode into Gail's wonderfully talented mouth, Jean's voice wafted off the walls and ceiling. "Night, boss have a good evening! Oh,and g'night to you, too, Ms. Appleton!"

Jack's voice came out in a muffled squeak. "Um, good night, Jean, see you tomorrow, drive safely."

Gail raised her lipsticked mouth and wiped the spittle off of her cheek. "Good night, Jean, I have him in good hands, don't worry!"

The nanosecond that Jack heard the deadbolt lock click on the outer door, he picked Gail up by her hips, carried her to his office door, slammed it shut, and, gripping Gail's muscular thighs, he began to savagely fuck the middle-aged training slut, ramming the back of the woman twenty-one years his elder into his door, again and again, and she pulled on the base of his skull and thrust her tight, clenching cunt into his hard slab of young man meat until they came as one in a shudder, the heated, vicious fuck lasting no more than two minutes, but serving to leave them both covered in sweat, heaving in shallowed breaths.

Johnnie carried Gail's lean body over to his desk, his hard rod still oozing cum into Gail's sopping tunnel as her own juices streamed out of her slit and down onto their connected stomachs, and laid her down gingerly. Accomplished and ravenous cockslut that she was, Gail still wasn't expecting what occurred next. After all, she hadn't been fucked by a stud twenty years younger than her, in, well, never.

"You think we're done, old lady? Fuck you," he growled. "We're just gettin' started, you dick tease. You wanna get FUCKED?" His eyes blazed now, both exciting and evoking a sense of fear in Gail. Her heart raced wildly, she had unleashed the beast. And it was between her legs, still hard as the concrete floor, her legs being spread wide as Jack gripped her hard by the ankle, placed her legs over his shoulders, and speared her with his eternally-hard cock.

He pounded Gail's cunt until his dick snapped again and again and again against her cervix, his one hand grabbed her ass so hard it bruised the tender skin on her firm buttocks, he pulled her hair so hard she thought it would come off at the roots.

And Gail loved it, she fucking LOVED it, she loved every enraged, hormonally-fueled thrust of Jack's monster cock into her pussy, she had never been so filled, so fucked into oblivion, the cum pouring out of her gash now, saturating Jack's working quarters and she screamed and wailed and moaned into the empty, deserted walls of the loading dock.

If a tree falls in the forest, and nobody is there to hear it, does it make a sound?

If a pussy gets fucked into a screaming frenzy, and nobody is there to hear it, did the pussy still get fucked?

You're fucking right, it does, Jack thought, as a second massive load of his jism shot like a jet stream into Gail's ravaged cunt.

He pulled out mercifully, Gail's head turning like Linda Blair's in 'The Exorcist', writhing on his desk in a puddle of her own cum, and he slapped his big dick, still hard, against her hugely engorged clit. "Now get the fuck out. Training over." He reached into his top drawer and roughly flipped Gail her bra and thong. "For today. I'll let you know when I want some old pussy again, you fucking dick-teasing cunt."

If Jack thought his actions were having the effect of humiliating Gail, he had severely underestimated his adversary, Gail thought as she gathered her lingerie and exited his office, walking unevenly, bow-legged, the recipient of the roughest fuck she had ever had.

Just the way she liked it, Gail mused, feeling warm and sticky all over. Wait until tomorrow. This young stud's training is far from over. In fact, she grinned to herself, rubbing her cum-covered pussy, it's just beginning. After all, I didn't get to be Training Director just by fucking Tim Rittenhouse.

Although, that certainly helped, Gail inwardly admitted.

Jack may have fucked her pussy with Olympian stamina, but Gail was going to fuck with Jack's mind. And Gail's cunning brain was an infinitely more powerful organ than Jack's Herculean dick.

By the time Jack arrived for work very early the next morning, as was his norm, the voice mail light on his office phone was already blinking, which was NOT necessarily the norm.

"Jack," the voice began sternly. John's heart skipped in recognition of Tim Rittenhouse's voice, the CEO and part-time paramour of one Gail Appleton. "Meet me in Tracie Heavens' office at 9 o'clock sharp this morning." No please, no thank you, no hope.

Tracie Heavens was the head of Human Resources, the second-most feared person in the company behind Rittenhouse. Jack was dead, at least from a professional standpoint, there was no getting around it. "Fuck me", he grumbled to himself in abject misery. "All because of a fucking training course that turned into a training course on fucking."

Jack made preparations in anticipation of the inevitable by grabbing a few small personal belongings in the event they would have him escorted directly from the building, and he sat and watched the clock click, agonizingly slowly, towards the witching hour, 9 a.m., the death knell for his career.

When Tracie Heavens' assistant told him to enter the HR boss' office, he saw Tim Rittenhouse sitting on the couch next to Gail Appleton, who was looking pale, forlorn, the picture of an abused fellow employee, a virtual poster child for sexual harassment, and dressed infinitely less provocatively than she was yesterday. Tracie Heavens sat stone-faced behind her big mahogany desk which all but screamed, "I'm important and intimidating, bow down in fear."

Rittenhouse spoke first. "Don't sit down, Jack. Instead walk over and stand next to Tracie." Jack did as commanded, thinking the request was strange. Little did he know.

"I'll get right to the issue, Jack," the forty-something human resources queen began. She was attractive enough, short blonde hair with a pretty farm-girl face and matching farmers' country daughter corn-fed tits, but alas, as the saying goes, 'Where big tits are, a big ass will soon follow.'

And Tracie was being followed, alright.

"Gail," Tracie turned toward the woman that Jack had so ravaged about sixteen hours before. "Show us the bruises." With great drama, the training director lifted her modest skirt which was well below-the-knee, turned around slowly, and with rich irony, bashfully peeled aside a pair of cotton white panties that would have looked conservative on Betty White, exposing deep black-and blue bruises on her buttocks and upper thighs. She then pointed to her ankles and upper arms, indicating similar contusions on her nearly transparent skin.

Tracie winced in mock disgust. She wasn't as good an actor as Gail. Tim Rittenhouse, shook his head and clucked his tongue, his face turning crimson, and looked leeringly at Jack, now mortified, ashamed.

He rattled off the names provided by Gail, and apparently verified and cross-checked by Tracie. "Jamie Ellis, Carol Young, Leslie Bobman...." He stopped roll call of the women in the company that Jack had fucked during his short tenure there, having already made his point. "And more, several more, no sense identifying them all, we all know there is quite a trail of your.... swordsmanship." He leered at Jack as he spat out this description of Jack's promiscuity.

He then turned back to Tracie. "Tell Jack what the discipline is for such illicit behavior, Tracie, please."

The chubby HR maven stood slowly, and then hopped her big rear end up on top of her huge desk, and lifted her dress to her belly button, displaying her naked, shaved twat, and Jack gasped audibly as she ordered, "Fuck me."

Jack stood paralyzed, and looked to Tim and Gail for some reinforcement, amnesty, executive pardon, anything. Tim Rittenhouse nudged Gail, who rose form the couch. and walked towards Jack, who was aghast, shell-shocked. Tim made a simple, but authoritative, pronouncement. "Suck his cock, get him ready."

With the skill befitting of a corporate whore, Gail lowered Jack's pants to his ankles and began the same slow, measured cocksucking that had initiated the previous days' carnal activities. Despite himself, contrary to every sensor in his brain, Jack's dick lost the struggle for self-control, and rose mightily in response to Gail's expert oral administrations.

Satisfied that Jack's missile was ready for launch, Gail grabbed Jack by the hips with her surprisingly strong grip, and guided his long dong to Tracie's dripping, waiting cunt, and he eased into the obese woman's snatch, and Tracie came with a yelping grunt after just a few short seconds and a few long inches.

Tracie continued to hump Jack's turgid cock frantically as Gail returned to the couch and snuggled under the chief executive's arms, like a scolded, remorseful teenager whom Daddy had caught fucking the neighbor.

"My cunt, my piece of ass, hands off, understand?" Tim pointed to Gail, and barked angrily at Jack, who stood statue-still while Tracie writhed merrily on his dick, aromatic moisture spilling out of the wide reservoir which was her pussy, her first fuck in ages, such that it was. She had now picked her big tits out of her blouse and was rolling them between her own fingers in orgasmic glee.

Jack nodded shamefully, just wanting it to be over. 'Just fire me and let me get the fuck out of here,' he pleaded silently, relieved when Tracie finally collapsed on the desk, apparently thoroughly sated by Jack's dispassionate, half-hearted fuck.

"That IS a big dick, Gail, I'll have to admit," Rittenhouse's stare at the young man's swinging dick made Jack more uncomfortable than anything else that had transpired today. "Too bad you can't have it anymore, you've had your fun, one and done."

"Twice," Gail thought to herself, her pussy tingling at the recent, vivid memory of Jack's member stretching her as she had never dreamed.

Rittenhouse continued, his demeanor discernibly softening. "Now, sit down, Jack, here's how you're going to help yourself out of this mess, and by doing so, save your career and perhaps the company's future as well. Seeing as how you like to fuck older women, and then mock them, maybe a little humility will do you good, young man. "