Young Boss Takes Advantage Ch. 19-20

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Two more women are hired, and experience office discipline.
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Part 10 of the 10 part series

Updated 06/09/2023
Created 03/23/2020
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Barefan
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Part 19

The next two weeks were anti-climactic for Tim. Both of his young employees were on their best behavior after their humiliating exposure during the previous week. After all, the office was an actual place of business, and both young women were good at their jobs, as was Tim.

Tim pitched a handful of potential clients the next week, and Mia pitched several of her own. They signed three new clients, and completed short campaigns for two existing clients, and the following week brought more of the same.

The fledgling satellite office was off to a great start, and Tim was only mildly disappointed that both Julie and Mia made no more than 3 mistakes in each of the next weeks, even though he did look forward to the next time he'd have a chance to get his hands on each of their pert bottoms.

His boss Shawna came by from the main office several times to check in on their progress, and she liked what she saw. Tim showed her their books, and she liked that even more. When he asked her if he could hire a new account rep, as had been promised, she surprised him by giving permission for him to hire two.

Tim called Mia and Julie into his office to talk about it. "I've got the OK to hire two new account reps. Since Julie recommended you, Mia, and since you've done so well, I was wondering if either of you know of any other good prospects for the new hires?"

Mia blushed happily at the compliment, and looked at Julie. "We do know a couple of other girls from our old sorority. They both graduated last year. I think they'd both be great at the job, but I'm not sure if one would go for it."

Tim said, "Tell me about them."

Mia said, "Both of them are really smart, and really outgoing. They both majored in advertising. Kaitlyn is very high energy, and bubbly, and she was especially good at writing ad copy during her internship. Anna is a little more on the serious side, but she can be very charming, and she was always an idea machine during our group projects."

"They both sound great. Which one do you think might not go for this job, and why?"

"Well," Mia said, shooting a glance at Julie, "Kaitlyn would love the job, I'm sure.

But Anna might be a little... hesitant."

"Why?" Tim asked, fearing that he might know the answer.

Julie stepped in. "Anna is a real feminist, so I'm not sure how she would react to your... disciplinary methods."

Tim tried not to look disappointed. "Don't you two think of yourselves as feminists?" Both women nodded. "I think of myself as a feminist, too. You know that I'm not against hiring women, and compensating and treating them well."

"That's true," Julie said. "But you also spank them when they make mistakes at the office!"

"Not too many feminists would be okay with that," Mia agreed.

"And yet you two are," Tim pointed out. Mia and Julie both shrugged, and nodded.

"Okay," Tim said, "why don't you two talk to Kaitlyn and Anna, and see what they think? Tell them the way the office works, and be honest. If Anna is offended, I'll move on. But if one or both of them are interested, I'll have them come in for an interview."

That evening, Mia and Julie met Anna and Kaitlyn at a local bar. They explained the nature of the job. Everything went extremely well, until they got to the punishment system.

"You're kidding!" Anna said.

"That's crazy!" Kaitlyn said. "He actually spanks you if you screw up, like you were naughty children?"

"It's hard to explain," Julie said, blushing.

Mia jumped in. "It sounded crazy to me, too, at first. But it hasn't been that bad. He's actually a nice guy, and the work is challenging and fun. The base salary is in line with industry standards, but the commission on any accounts I bring in is really good!"

"Mr. Johnson has given me a commission incentive, too, which never happens. I've got the title of office manager instead of secretary, and I get monthly bonuses that are tied to the total amount of business the office does each month."

"But he spanks your asses!" Anna nearly shouted. Several patrons nearby looked at the four women at their table, and Mia said, "Keep your voice down!"

"I just can't believe this," Anna said, more quietly.

Mia said, "I know it sounds crazy. I gave Julie a hard time about it when she brought it up. But there's something about the way he runs things. He's not mean, or unfair, and he's not a leering perv about it."

"Do you think he's gay?" Kaitlyn asked.

"No," they both said at once, and then giggled a little. "I mean," Julie said, "it's obvious that when we had our skirts up and our panties down, he liked what he saw."

Kaitlyn leaned forward. "He had a hard-on?!"

Mia and Julie both nodded, blushing just a little.

"How... big is he?"

"I can't believe this conversation," Anna said.

"I didn't have a ruler out or anything," Julie said, grinning.

"But you could tell that he wouldn't have come up short," Mia said, and all four girls laughed, Anna in spite of herself.

"And you said he's hot?" Kaitlyn asked.

Julie and Mia both nodded, and Anna repeated herself. "I can't believe this."

Mia said, "We didn't think you'd go for it. We'll tell him you're not interested."

Anna held up a hand, and Mia remembered her initial conversation with Julie about the job. "I'm not saying that, necessarily."

"You are interested?" Kaitlyn said, surprised.

"I'm not thrilled about it," Anna said. "But I need a job. And if the rest of the job is as you describe it, it might be worth at least going in for an interview."

The other girls were excited. "It would be so cool to all be working together!" Julie said.

"Yeah," Mia said. "And we'll have him outnumbered. Maybe after we get a little experience and start bringing in our own clients, we can renegotiate with him."

Kaitlyn said, "We could threaten to all quit at the same time, unless he agreed to stop the sexist punishments!

"I like the sound of that," Anna said. She grinned at her friends. "Maybe if we bring in enough business, we can turn the tables on him. We can tell him that if he makes a couple of mistakes, we get to whack HIM with a ruler!"

"Yes!" Mia said, her eyes sparkling. "And if he makes another mistake, we'll make him drop his pants for a hand spanking!"

"And if he screws up after that," Julie said, "we totally pants him, and spank his cute bare butt while he's bent over his own desk, with his pants and boxers at his ankles."

All four women howled at that idea!

When they'd recovered, Mia said, "Let's not get ahead of ourselves. First we need to get you two hired, and then you need to do a good job. We might be able to eventually even out the power politics in the office, but in the meantime, Mr. Johnson is going to be wearing the pants in the office, and it will be our butts on the line if we screw up."

Part 20.

Tim interviewed Kaitlyn first, and he knew within a few minutes that she was on board. She was tanned and attractive, with shoulder-length dark hair and the kind of glasses that make her look both pretty and smart. She had a good figure -- Tim guessed that her breasts were C-cups, and her tush filled out her conservative skirt nicely.

When he brought up the office disciplinary plan, she blushed and nodded and said that she'd do her best. She beamed when he offered her the job, and he put her together with Julie to start going over the hiring paperwork.

He interviewed Anna later that day. She also wore a conservative skirt and blouse combination, with short heels. Her dark hair was pulled back away from her pretty, even features. Her eyes were light brown and her skin was fair. She wore subtle makeup, and a bolder red lipstick.

She was a little reserved, but she was impressive throughout the interview. She was intelligent and relaxed, and had answers for all of his standard interview questions. Finally, Tim asked her, "Do you have any questions for me?"

She said, "I think I understand the job, and your compensation plan seems more than fair. My only question is about your disciplinary methods."

Tim kept his expression neutral. "What's your question?"

She fidgeted for the first time. "It seems anachronistic, and sexist."

Tim raised an eyebrow. "That's not a question."

Anna rose to the challenge. "Would you let a female boss spank you, if you made a mistake on the job?"

Tim said, "I guess that would depend on the boss, and the job, and what kind of mistake I made."

She looked at him for a moment. "Is this a sexual, pervy thing?"

"Absolutely not. It's purely intended to motivate my employees."

"It sounds like it's meant to embarrass them."

"Avoiding embarrassment can be a strong motivator, wouldn't you agree?"

Anna considered the question. "It could be, I suppose. It could also be harassment."

"I've never behaved inappropriately with any of my employees. I'm sure that your friends have told you that."

"Other than making them expose their backsides, and spanking them, you mean?"

"As I said, that's a motivational technique. I don't consider it harassment, but you are entitled to your own opinion, and of course you are free to turn down this job offer if you object."

"Does that mean that you are offering me the job?"

"I am. I think you'll be a good fit here, and if you do your job carefully and avoid mistakes, my disciplinary policies will be a moot point."

Anna looked thoughtful. "Can I think about it?"

"Do you really need to?" Tim asked, a slightly amused expression on his face.

Anna saw that expression, and wanted to wipe it off his handsome face. Julie and Mia hadn't lied: he was good looking. But being disciplined by her boss? She felt her face flush a little.

Finally she said, "If you ever did need to... discipline me, I'd like there to be witnesses."

Tim's eyebrow went up again. "Really? Do you have an exhibitionist streak?"

Anna felt her face get hot. "No! I just don't think it's appropriate to do... that... when I'm alone with my boss."

"I would never take advantage of the situation, but whatever you say. If I were ever to have to discipline you, I can promise that you can have an audience."

"That's not—" Anna began, but stopped herself. She was about to say that that's not what she meant. But what DID she mean? That if she would have to bare her bottom and get a humiliating spanking at her place of work, she wanted her co-workers to see it? On the other hand, would it be any better if she got spanked by her cocky hunk of a boss behind closed doors, alone?

"Fine," Anna finally said.

Tim smiled, and stood up, extending his hand. "That's great! Welcome aboard."

Over the next three weeks, Mia and Julie made Kaitlyn and Anna feel at home, while Tim oriented them both to the job, and their responsibilities. During the first week, neither of them made any mistakes, and they both proved to be quick studies, smoothly picking up the nuances of the job.

Julie and Mia were also on their best behavior that week. If an outside observer had watched the activity in the office, he would never have known that Tim Johnson had an unusual approach to employee motivation at all.

The following week, Kaitlyn and Mia both made a series of mistakes, and earned themselves first the ruler on their hands, then on their skirted bottoms. When they simultaneously mixed up some client files that Thursday, both of them blushed when Tim called them on it.

"Okay," he said, gesturing toward Julie's desk. "Let's get this over with." They marched over and turned toward the desk, standing next to each other. Kaitlyn looked at Mia, who took the lead, by raising her own skirt, revealing a pair of snug but fairly conservative pair of light blue boyshort-style panties.

Anna stood in her doorway, shocked. The others had told her all about this, and she knew that it could happen. But she realized that she'd never really believed it, until now.

Kaitlyn quickly glanced at Mia's boyshorts, and moaned softly. With trembling hands she lifted her own skirt, to reveal a much more daring, nearly thong-backed pair of panties that exposed most of her perky, round bottom.

"Ooh," Julie teased. "You must not have seen this coming!" Mia smiled, but Kaitlyn just blushed.

As she quickly joined Mia, leaning away from him and over Julie's desk, Tim kept his poker face on. But he was very pleased to see Kaitlyn's firm buns, which looked as good as he'd imagined they would. He quickly started slapping the two women's quivering behinds with his ruler.

Anna watched, mesmerized. She couldn't help but wonder what it would be like to be in their position. The thought made her even more resolved that she would NOT end up in that position, even though she found herself unwillingly beginning to play that scenario out in her head.

During the following week, Kaitlyn once again ended up making three mistakes, but this time, Anna joined her. When she made a couple of minor faux pas on Tuesday, Tim had carefully observed her reactions.

After the first infraction, she held her hands out in front of her, while keeping her expression carefully neutral. Tim rapped them lightly, and then said, "That's not so bad, is it?"

Anna didn't give him the pleasure of a reaction, turning back to her business with no comment.

She kept the same neutral expression after her second mistake, turning her back on him quickly, but being careful not to bend forward, or make any other concession to the fact that her boss was about to slap her behind, through her skirt, with a ruler.

Tim put a little more force than necessary into the spanks, just to try to get a reaction from Anna. She wouldn't give it up though, and stoically accepted the punishment before heading back to her office without a word.

Tim did smile, though, when he saw her right hand quickly sneak back behind her to furtively rub what he knew must be a little sting out of her slender but still curvy rear end.

After two days on her best behavior, and shortly before the end of the work week, Anna made her third mistake. Shortly before lunch she left a voice message for a potential client she was cultivating. Then she and the other women went to lunch.

When they got back, Tim asked if he could talk with her a minute. She stepped into his office, and he gestured for her to close his door.

"I just got a call from Dianne, my dry cleaner client. She said that she didn't understand why you were trying to set up a meeting early next week."

"But I didn't try to—" Anna said, before stopping herself. Tim noticed a slight blush at the base of her neck, as she frowned just a little. "I mean, I called the lead you gave me to set up a meeting early next week. But—"

"But you actually called Dianne, by mistake," Tim finished for her. "So you need to call your actual client again, and give them the message that you meant to send earlier."

"Right," Anna said quickly. "I'm on it." She spun quickly toward the door, but before she could open it, Tim's voice stopped her.

"You realize that this is your third mistake this week?"

Though she was turned away from him, Tim could detect a slight stiffening in her posture, before she turned back toward him. "Is this really a mistake, though? I mean, it was no big deal for your dry cleaner, and I can leave the message for my clients right now, and they'll never know the difference."

Tim just stared at her evenly, without saying anything. Finally Anna said, "Fine!"

She stepped over toward his desk, her blush now extending up her neck and into her cheeks.

"What are you doing?" Tim asked.

She stopped in her tracks, and gave him an irritated look. "Very funny. Let's just do this so I can get back to—"

Tim actually gave her a small finger wag. "You said during your interview that if you ever needed to be punished, it had to be in front of your co-workers."

Anna instinctively glanced back toward the office and frowned. "I've thought about that, and I've changed my mind. Here will be fine."

"No, no," Tim said. "You said that being alone with me for this wouldn't feel right, and I promised you that I'd honor your request."

Anna put her hands on her hips. After working here for almost three weeks, she now knew that whatever else he was, Mr. Johnson was not the sort of creep to take advantage of his employees sexually. The thought of pulling up her skirt so that he could slap her pantied behind with a ruler in his office was very embarrassing.

But not as bad as doing it in front of her friends in the outer office!

"I'd really prefer to—"

"I'm a man of my word," Tim said. "So I insist. I'm going to honor what I told you during your interview."

Anna swallowed hard, as Tim came around from behind his desk and opened his door for her. Trapped, she had no choice but to walk through. As Tim lead her toward Julie's desk, Mia was just stepping out of her office. "Ladies, I'd like your attention for just a moment."

Mia walked over, and Kaitlyn came out of her office to join them. She saw that Anna was looking at her shoes, and all three women wondered what was going on.

"When I interviewed Anna for this job," Tim said, "she asked that if she ever made a third mistake in the office, she wanted her punishment to take place in front of witnesses. Well, she just made her third mistake this week.

"Ooh," Julie said, "this is going to be good!"

"I didn't think this day would ever come," Kaitlyn said, grinning.

Anna glared at her friends. Earlier in the week, she had joked with them all, saying that she was the only one in the office whose panties Mr. Johnson hadn't seen. Now her playful teasing came back to bite her.

"All right," Tim said, "even though this is your first time, you know the drill." He gestured toward Julie's desk.

Anna dropped her eyes again and stepped quickly forward. Her hands were noticeably trembling as she reached back and grabbed both sides of her skirt. Because it was a fairly long one, she had to bend a bit to grasp the bottom, and when she straightened up, she began to squirm subtly as she started to pull her skirt up.

Mia stepped to the desk and performed a little drum roll with her fingers on the wooden surface, and Anna shot her a dirty look. Then she looked down at the desk, and wriggled as she tugged her skirt upward and over her flared hips.

Tim watched with delight as the skirt cleared those hips, unveiling a pair of pale, inviting bottom cheeks, covered only partially by a pair of white cotton panties.

"Wow! Catholic school girl panties!" Kaitlyn said, giggling.

"How cute!" Julie said.

Anna muttered, "Shut up," but she wouldn't meet their eyes.

"Very nice," Tim said, just to rub it in a bit. "Now let's give you something to motivate you."

Anna snorted, and then yelped as the cold ruler found the roundest part of her protruding left cheek. Then the right, and she couldn't stop from giving a little waggle that she knew must have looked ridiculous. Mia clapped as Tim continued to make Anna's tush jiggle.

After the last spank, Anna quickly dropped her skirt, but not before all four witnesses had seen the 2-inch stripes of pinkening skin already appearing on the pale flesh of her gorgeous derriere.

Anna steamed off to her office, amidst the giggles and teasing of her friends. She closed her door and sat behind her desk. How humiliating! What had she been thinking, to take a job that involved this kind of degrading treatment?

And why was she feeling some small measure of tingling, naughty pleasure at being treated so disrespectfully?

For that entire weekend, Anna's first spanking was never far from Tim's mind.

She and Kaitlyn were great additions to the office, and not just because of how quickly they'd made it up the learning curve. He was now the boss of his own, already strong-performing satellite office, and he had managed to surround himself with attractive young women who would willingly allow him to discipline them in the most enticing, pleasurable ways!

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