Advancement
What a ball buster, Leo thought.
Sitting across from him, separated by a grand, sweeping, dark-toned office desk, Jessica smirked in calm repose. Her regal air gave her the appearance of a cat-like sphinx and Leo couldn't help but be, at least, slightly unsettled by Jessica's focused gaze. It also didn't help him that she dressed in the nearly provocative ways for which she was well known in the office. Plunging necklines, short skirts, sometimes the occasional pair of stockings that peeked out mid-thigh as she sternly, and knowledgeably, lectured those around her, Leo was familiar. Today was no exception with the small, amber mini dress wrapped around Jessica's tight frame. Why did it have to be her, a fully fledged Vice President, who conducted the interview and not one of the many Directors Leo was on good terms with?
Quietly confident, Jessica leaned back in stoicism continuing to stare at the young man. The question was simple, "Describe a time when you failed at work and what did you do to solve it?" Jessica ticked off the item from her mental checklist and waited for Leo's response.
Jessica's tenure at the Company far eclipsed Leo's more youthful presence. It had been more than ten years since she'd joined and Jessica had not only shifted her way into a male-dominated tech industry, but thrived here as well. Through sheer grit and determination she had earned her place among the upper echelons of the Company's ranks. It didn't hurt that she was attractive to look at too.
Leo, by contrast, was a newly-minted graduate, fresh from an MBA and looking to cut his teeth alongside his peers who had encouraged him to go back to school for more opportunity. Working full time while attending his MBA had proven a challenging task. The Company had subsidized some of his tuition, that part was nice, and he'd been encouraged to stay with the organization with the prospect of increased pay and more responsibilities. But those conversations seemed far, far away now as he was faced with the only person in the organization he didn't understand.
"Well..." Leo began, sensing his wavering confidence.
Jessica listened to Leo's words, gently tapping a pen between her fingers in time to his rhythm. She didn't care if Leo noticed. He was a diligent worker, a good student based on his academic marks, and someone she imagined was as reliable as he was uncertain at times. Like all recruits into the Company, Jessica paid special attention to Leo's performance when he initially arrived, looking for talent that could be fostered and turned into a significant asset. As a Vice President, Jessica had the unique task of vetting all candidates, internal and external, for advancement.
Leo finished his thought, "...which is why I now commit myself to seeing projects through beyond the scope of my team's work."
Jessica turned her mouth up at the corner in a tortuous smile, "So you take on more responsibility than you're assigned? That doesn't sound like a solution to me."
Leo reeled. The nerve of this woman to take such a position irked him. He felt his heart quicken and his cheeks flush with warmth at the thought of having to prove himself. It wasn't a feeling Leo enjoyed and he closed his eyes briefly to recenter and calm a bit.
Jessica broke her metered demeanor and leaned over the table, revealing her voluptuous bosoms as they pressed against her dress. "What? Do my words bother you?"
Leo couldn't help but fall on the defensive, "It's not that they bother me. I just. Don't agree with your perspective." He paused, then finished, "no offense."
Jessica took a beat and looked somewhere above Leo's gaze and far into the room beyond, considering. She liked Leo. His short, brown ringlets and ambitious nature gave him a youthful appeal. More than a few times, she noticed his encouraging laughter lilt through the halls to her cracked office door. For someone in the tech industry, Leo also carried his physique well. Whatever he did to stay in shape, she thought, it worked. It was clear he had a social life outside the four walls of the Company and sometimes Jessica wondered what he did with that time. Sensing some satisfaction, Jessica resumed her sphinx pose and looked back at Leo. In this case, she knew she had the upper hand.
"Get on your knees." Jessica said, staring Leo through, unmoving.
What!? Leo's mind raced. He couldn't believe the words that exited Jessica's pouted mouth. For a moment he didn't know what to do. As far as he could tell he had two options. First, turn tail and run, kissing his current chances at promotion goodbye. This, in addition to giving up the Vice President and causing a human resources nightmare he wasn't sure he was ready for, seemed like an unkind option. Second, and by all accounts the more intriguing course of action, was to listen to Jessica and see where her line of thinking went.
Leo stammered before he knew what he was saying, "But-, but what about the rest of the office?"
Jessica gently reached forward and grabbed a small remote sitting in the middle of her desk. With the press of a button the glass to Jessica's room turned opaque and the bustling office outside disappeared behind a thin layer of electric gossamer. One couldn't see in nor out.
"Get on your knees." Jessica repeated, as stoic as she had been when Leo initially arrived.
Leo could feel his heartbeat in his throat. Mindless, he slid off the front of his chair and settled on his knees. What in hell was happening? He wondered.
Jessica smiled and stood. In a metered sway she walked to the door and flipped the lock.
"I've been reviewing your performance Leo," Jessica began as she walked back to the front of the desk, stopping in front of where the young developer remained on his knees. "I must say, you seem to rise to the occasion when called upon."
"Th-. Thank you." Leo stammered.
Jessica enjoyed seeing Leo tortured like this. So out of his element. So unsure. Her efforts had worked and she was turned on at the thought of continuing to play with the young man.
"Well, we'll see." Jessica continued. "Are you ready to rise to the occasion today?"
Leo looked up at Jessica who peered down at him over her full breasts. Her imposing stature only encouraged him, though he wasn't sure what to make of the situation. "Yes. I'm ready." Leo swallowed hard.
Jessica cocked her head and smiled. "Good," she said and turned around, pushing her ass toward Leo's face. With her anticipation reaching an intolerableness, Jessica was confident Leo wouldn't spook. "You can start here."
Jessica leaned over the desk and lifted her dress to expose her panty-less bottoms. Leo knelt inches from her smooth, peachy rear. Between her spread legs, Jessica's pussy looked delicious, trimmed and glistening.
Leo blinked, frozen and uncertain what to do next.
"Lick me," Jessica's firm tone resonated as she gestured at her naked backside and looked at Leo.
Dumbfounded, Leo closed his eyes and leaned forward. The soft, spicy wetness of Jessica's groin sent electricity down Leo's tongue and through his stomach, settling somewhere warm between his legs. Jessica dropped her head and let out a soft moan.
Grabbing Leo's hair, Jessica pulled Leo's head against her ass. Leo could feel his face buried somewhere between Jessica's asshole and pussy.
"Don't stop." Jessica's words came firm, but breathy.
Leo reached to either side of Jessica's legs and pulled her curvy thighs tight against his mouth. He could hear Jessica's stifled murmurs as he buried his tongue deep inside her.
Jessica reached her free hand to her mouth and bit her finger, knowing she and Leo both had to be quiet. The sensation of Leo's tongue running across her pussy and up around her tiny asshole set her mind ablaze. Only a few feet from where she stood, on the other side of the obscured glass, the rest of the office worked naively away. For all intents and purposes, behind the locked office door, Jessica and Leo were neck-deep in their interview, not each other. But Leo had capitulated perfectly, a willing participant in Jessica's deeply seated desires.
And now Leo was both eating her out and rimming her ass. Perhaps she and Leo would need to have a conversation about the state of affairs before he left her office, but in the moment Leo was proving his worth, a worth Jessica had believed existed from when he first started at the Company.
Jessica released her hold on Leo and she could hear him gasp for breath as he leaned back.
"Fuck..." Leo said quietly, catching himself.
Jessica rose once more from her position over the desk and turned to Leo. "Take your pants off and sit," she commanded, pointing at the chair Leo had vacated.
Leo reached for the arm of the chair and scrambled to get up.
"Slowly." Jessica looked Leo dead in the eye.
Leo took a breath, removed his shoes one by one, and reached down to his pants. Undoing his belt and zipper he let his slacks fall to the floor.
"Boxers too." Jessica waited, tapping a finger against her crossed arms.
Leo sheepishly smiled and bent over, putting a thumb on each side of his waistband and letting the fabric fall to his feet.
Leo's cock stood at full attention, freed from where it had been hidden inside his pants. His modest length and girth was enough to elicit a quick smile from Jessica. Without warning, Jessica put a hand against Leo's chest and pushed him back into the chair below.
"I said sit." Jessica's clear tone ricocheted around the room. "And hands to your sides."
Entranced, Leo put his hands on the arms of the chair and held his breath.
"It looks like you have risen to the occasion today." Jessica's words were both playful and serious. "Now, let's see if you go beyond this project's scope of work."
Jessica reached down and grabbed Leo's thick erection. As much as she wanted to feel Leo in her throat, Jessica wasn't going to give him the satisfaction. Instead, she imagined she'd tease him for a while, milking his cock with her pussy until he couldn't stand it anymore.
"Remember, hands to your sides." Jessica stated plainly as she moved her dress, once again, up over her hips. Using the desk to brace herself, Jessica squatted down above Leo's hard rod. She loved making her suitors wait, teasing them while they weren't sure what might happen next.
Jessica squeezed Leo's erection in her hand, forcing its head to swell and sending shivers up Leo's spine. Jessica smirked and plunged herself firmly down, feeling Leo's swollenness fill her completely. Putting a hand over her mouth, she muffled the urge to make noise.
Below her, Leo also did his best to stay quiet. He had been taken aback by the forcefulness of Jessica's actions and it only heightened his pleasure. Now, he couldn't help but focus on the sensation of the Vice President's tight pussy wrapped unrelenting around his stiff cock. Without thought, Leo reached up to touch Jessica's breasts.
"Don't fucking move until I tell you." Jessica's words came stern and forceful and Leo immediately retracted his attempts to fondle her, placing his hand again on the arm of the chair.
Jessica kept pumping her hips up and down, even as she commanded, turned on by her authority over Leo. She could feel Leo's cock thicken as she forced herself deeper onto him. "And don't fucking cum yet."
Leo winced his eyes as he did his best to fight the sensation. The feeling of Jessica riding him, telling him to obey, surprised him in how much he was aroused by it. With every vertical pulse up, then down again, Leo worked hard not to orgasm.
Jessica looked at Leo's tense body. She could see how intently he resisted his urges, covering his eyes and twisting his mouth as she rode him. Jessica couldn't help it and shuddered above her inferior, feeling herself cum while she watched Leo's valiant efforts. Leo was too focused to notice Jessica shaking atop him, until, finally, she regained her senses.
"Good boy." Jessica said under stilted breath as she stood up. "I want you to finish in my ass."
Leo blinked and nodded, his throbbing member in need of release. Once more Jessica bent over the sweeping desk and spread her cheeks, her puckered asshole peering out at Leo.
"Now." Jessica demanded, her face resting against the desk.
Without hesitating, Leo carefully stood and stepped between Jessica's parted legs. Grabbing his cock, he pushed its swollen head against her obstinate hole. Leaning against her, Leo could feel Jessica's tight ass swallow the tip of his cock. Slowly, he fed the rest of his length to her until he felt Jessica's ass flush against his groin.
Jessica couldn't help herself and began writhing back and forth. The feeling of the full length of Leo's cock buried deep in her ass drove her mad. But this time, she didn't want to tease, she wanted to feel Leo finish. She wanted to feel Leo's cock explode deep inside her, trapped and throbbing.
"Fuck me," Jessica begged, keeping her voice low, but stern. "Until you cum."
Leo furrowed his brow and leaned hard against Jessica's arched, prone body. He felt Jessica's asshole tighten around his member as he pushed into her. One thrust after another Leo pumped into Jessica as he felt her work to drain him.
Jessica could feel Leo swelling with climax. She knew he wouldn't last much longer and reached back to Leo's legs to ensure he kept pounding her while he came.
"Inside," Jessica whimpered.
Jessica's hands against Leo's thighs, coupled with the feeling of her tightness enveloping his member, sent him over the edge. Squeezing his pelvic floor, Leo tossed his head back and gritted his teeth as he came hard.
Jessica felt Leo's warm load spurt deep inside her. He rocked his member back and forth as hot liquid pumped from his spent cock. Leo let out a low cry at the sensitivity of his member stuck far inside Jessica's stretched hole.
"Don't move," Jessica commanded, bearing down on Leo.
Licking her fingers, Jessica reached a hand between her legs and began to play with herself. The fullness of her ass felt wonderful as she moved her fingers in circles across her clit. Jessica was impressed Leo was about to make her cum a second time.
The orgasm came fast and strong as Jessica tightened her full asshole against Leo's still-hard member. With each contraction, she felt Leo's cum dripping between her spent gape and his thickness until, finally, she forced Leo's cock free from her ass. The waves of orgasm lingered like a distant melody until, finally, Jessica shook her head and stood up.
Reaching across her desk, Jessica pulled a tissue from a small box and wiped her and Leo's cum from between her thighs. Pulling her dress back over her waist and down her legs, Jessica adjusted herself. Taking a moment to regain her composure, she watched as Leo gathered his boxers and slacks and dressed himself.
Jessica crossed her arms and looked at Leo, "So, how do you think your performance went today?"
Leo tucked his shirt and buckled his belt. He wasn't sure exactly what had just happened, but he knew he was now part of something intimate and profound. Leo considered for a moment, then said, "I can do better."
Jessica paused and smiled, taking Leo's words into account. Finally, she spoke, "You start your new position Monday next week. I'll see you for your weekly review on Fridays, just like today. I hope you're ready to keep me impressed."
Leo nodded, adjusting the buttons on his shirt, "I am."
"Good," Jessica mused. "Now get out of my office."
- Leon contemplated the challenging interview ahead with Vice President Jessica, known for her discreet yet provocative attire and commanding presence in the office.
- During the interview, Jessica turned the focus to Leo's past failures at work and how he had overcome them, seeking evidence of his ability to take on more responsibilities and rise through the ranks.
- Leo's promotion was in jeopardy as Jessica gave him a unique task, requiring him to commit to projects beyond his assigned role to prove his dedication to the company.
- Amidst the ordeal, Leo's boss commended him for his performance, mentioning that his ability to rise to the occasion had been impressive during his tenure at the company.
- Post the interview, Jessica offered Leo a new position, inviting him to demonstrate his deep-rooted talents and prove his worth in the office, setting the stage for his potential advancement and growth with the company.
