Her true intentions

Aileen just sat there, staring into Jared's eyes. He was trying hard to meet her gaze without melting. She always had the ability to scowl her employees into submission.

Jared thought to break the building tension by asking her what was up, but just as he was about to, she broke all composure and let out an exasperated sigh. It was as if she had transformed into a new, incredibly stressed version of herself in an instant

"That little brat is driving me insane," she said, sounding exhausted. Jared admired her ability to remain calm on the surface.

"Oh, she doesn't seem that bad. She's what? 19? I remember that age, I was always get—"

"She's helpless!" Aileen interrupted. She began pinching the bridge of her nose, something Jared had never seen her do. He wondered why she was telling him all of this.

"When I was her age," she began, "I was very similar. But my father was a tough, strict man, and he wouldn't have stood for any of the shit that girl has put me through. He would have pulled me across his lap for a good, long spanking." Jared's heart began pounding. The thought of 19 year old Aileen being spanked was sending shivers down his spine and blood to his already swollen dick.

"Just yesterday, I get home from a long day here at work, and what do I find? My house is thrashed! She must have thrown another fucking party in the middle of the day, and yet she's nowhere to be found! Kids these days can't just party in one place, they gotta keep the party going from place to fucking place until they've all passed out! Luckily, Kayla got home around the same time as me, so I had some help cleaning up Becca's mess."

Jared thought about Kayla, Aileen's younger daughter and only other child. She must be about 17 by now based on Rebecca's age. He hadn't seen Kayla outside of some pictures of her as a child in Aileen's office, but seeing how Rebecca has turned out made him wonder what her sister would soon look like.

Aileen continued, as if having a conversation with herself, "And don't get me started on the boys she brings over. My God, they're a bunch of fucking losers! Yet time and time again, she brings them home to have sex in my house. How do I know their having sex, you might ask? Because I just happen to stumble upon it everywhere I go! It's like they she likes being caught or something. Fucking pervert!"

At this point, Jared was struggling to keep up. Not only was he completely unprepared for a conversation like this, but the way in which Aileen kept making gestures with her arms was quite distracting. Every movement sent her breasts jiggling within their push-up prison, begging for Jared to free them.

He could sense that Aileen was getting carried away, so thought to intervene.

"Hey, Aileen?" he asked softly.

"Yes?" answered Aileen, as if pulled from a trance.

"What's all of this about?" Jared asked, plainly.

Aileen let out another sigh, not as grand as her first, but it seemed equally satisfying.

"You remind me a lot of my father, Jared." she began, adopting a friendlier aura.

"Not in appearance, obviously, but in the way you conduct yourself. The way in which you managed the creative department was both efficient and clean. You didn't put up with any bullshit, but you didn't reign like a tyrant either. You nurtured your team and they loved you for it. Unfortunately, I was unable to keep the entire department long-term. So, in an effort to kill two birds with one stone, I wanted to give you the help you deserve while getting that brat out of the house during the day until she leaves for college."

"I suppose that makes sense," Jared said, trying to convince himself that Rebecca would be of any assistance to him. If anything, she would be the worst possible distraction for him right now.

"There's something else to it, Jared. I've seen what it is you do when you are alone here at night." She said, dropping a bomb in Jared's stomach.

WHAT!? Jared screamed in his head.

Aileen's demeanor shifted again, this time she sported a wry smile while crossing her arms, pushing her tits out even more than Jared thought possible.

"I had Sean from I.T. give me an app that allows me to view what is on anyone's screen here at work. I rarely use it, but when someone pulls OT, I generally take a peek just to make sure they are actually working. For the most part, that seemed to be what you were doing..."

Jared couldn't believe what was happening. How could he have been so stupid?

"It was late, and having seen you working on an important project, I was about to log off. But just then, you pulled up an incognito browser."

What began as a pit in his stomach evolved into a confusing mixture of shame and arousal. Why was Aileen smirking? Why wasn't she angry? Jared mostly feared what came next, as he wasn't sure which night Aileen was talking about, but he most certainly remembered what he did in between working.

"I'll admit, Jared, as soon as the first video started playing, I was incredibly disappointed. But that was quickly replaced with curiosity as I found myself drawn to what was on the screen."

Jared was now paralyzed. What the actual fuck was happening?

"A schoolgirl was getting quite the spanking by what appeared to be her very angry teacher," she explained, "and I found myself getting incredibly aroused. My hands took on a mind of their own as I began masturbating to the same video as you. Of course that wasn't the only video you watch that night, but they all followed the same basic theme. Although, the ones involving anal punishment were what really sent me over the edge. I hadn't watched porn in a long time, let alone some good stuff like that."

His mouth went completely dry. Did she really just say that? Was this some sort of strange test? Was he failing?

Aileen stood up and turned toward the window behind her, leaning on the window sill. In this position, the fabric of her pencil skirt was stretched to its limit around her firm bottom. There was no doubt she was doing it on purpose.

Without turning to face him, she continued her monologue.

"It was only after my third orgasm that the idea came to me," she said, slowly turning around, catching Jared in a drooling gaze. At this point he had lost all self-control, and was openly gawking at Aileen's body.

Aileen leaned on the desk, allowing Jared the most amazing view of her cleavage.

"Pay attention, Jared." she stated coldly. He collected what little dignity he had left and met her eyes, feeling the heat of shame on his cheeks.

"Becca wants to pursue a career in marketing and advertising, but lacks the discipline and focus to even get through college. I need you to whip her into shape, Jared. I want you to be tough on her, and provide her with the strong, male presence that I was fortunate to have grown up with. The absence of a father figure in her life has had it's consequences. I'm not asking you to fill that void, just to provide her with the structure that I was apparently unable to. Do you understand what I'm saying, Jared?"

He did his best to collect himself by clearing his throat, but his mouth was so dry it turned into a small coughing fit. Aileen dropped her head to the side as if saying "really?"

"Y-yes, ma'am. You w-want me to m-manage... err rather, provide s-structure to uhh—" he stammered as Aileen cut him off.

"Jesus, Jared, I get it. It's a lot to process. Here let me lay it out for you. When Becca fucks up, I want you to discipline her however you see fit. That means you have my permission to spank her, humiliate her, and fuck her if necessary. Obviously, that last part needs to be in a disciplinary manner as well, just like in your favorite videos. Oh, and don't worry, I've got some dirt on her that all but guarantees her cooperation. This is equal parts a lesson for her and a reward for you, so don't make me regret it," she ended, with a finger slightly pointed in his direction.

That's it, Jared thought, I've gone insane from sleep deprivation.

Aileen began walking seductively around her desk toward Jared, slowly tracing her finger across the top as she did.

"And if by the end of these couple of months I find that Becca is adequately prepared for school," she said, completing her journey and sitting down right in front of him on the desk, "I'll have an even better reward for you." She finished by biting her lip and crossing her legs, giving Jared a flash of her red, wet panties in the process.