"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."
