Young Boss Takes Advantage Ch. 05-06

Story Info
Tim's friend speeds up Julie's embarrassment.
3.1k words
4.41
62k
15

Part 3 of the 10 part series

Updated 06/09/2023
Created 03/23/2020
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Barefan
Barefan
268 Followers

Part 5.

That evening, Tim got a call from an old college buddy, Neal Roth. He'd been one year behind Neal in school, and they'd kept in touch in the years since, partly because they stayed in the same town, and partly because they'd gone into the same business. Neal had been a marketing major, and in the years since school he'd climbed the ladder as a brand specialist for a large company who owned a variety of personal care and consumer product lines. Neal had established himself as an aggressive up-and-coming star at his workplace.

He was also an inveterate skirt chaser, so when he and Tim had a couple of beers at a local pub that night, Tim naturally told him the story of his pretty, gullible employee Julie.

Neal couldn't believe Tim's luck. "She let you whack her on the ass with a ruler?!" Tim smiled and nodded, taking another drink of his beer. "She pulled her skirt up first, and showed you her bare ass?"

Tim said, "Well, it wasn't bare. She was wearing panties."

"What kind?"

"Regular, cotton ones, I guess. Light blue."

"And she has a nice ass?"

"It's great," Tim said. "Round and firm. It's pretty big, for her small frame."

"You dog!" Neal said, slapping Tim on the shoulder. "You've got to be the luckiest guy in the world. First you get your own office to start, then your first employee is a hot blonde bimbo!"

"She's not a bimbo," Jim said. "She's a nice girl."

"Well she must not be too smart, if she fell for your line about spanking your employees."

"She's not stupid, either," Tim said, feeling a little disloyal to his first employee.

"She's just a little gullible."

"A little gullible?! I bet if you put your mind to it, you could talk her into flashing her cute little tush at you every day." Neal slapped Tim's shoulder again. "You ought to explain to her that any employee who screws up your coffee order has to work the rest of the day topless."

"You jackass," Tim said, laughing. "She's not an idiot!"

Their conversation moved on to other topics, but on the way home after they parted company, both men thought about the mental image that Neal had created: Julie, looking at Tim's disapproving look as he put his coffee cup down, and then slowly pulling her shirt up and over her head. Neal decided that he had to find some reason to stop by and see Tim at work, just to get a look at his cute blonde secretary.

The next morning was a pretty normal one, although Tim and Julie both felt a little nervous excitement around each other. Each of them had spent a lot of time the previous night thinking about what had happened yesterday. Tim remembered the smooth skin of Julie's half-exposed, jiggling butt as she wriggled her skirt up over it, and Julie remembered the tingly embarrassment as she bent over in the office like a naughty girl, sticking her bottom out at her handsome boss, with only her thin cotton panties as cover! They were both self-conscious around each other as the day began.

Just before lunch, Tim had to go across town to meet a potential client. As he left the office, he said, "I'll probably grab lunch after I see this client, so I'll be back around 1:00, Julie."

Neal arrived at Tim's office in the middle of lunch hour. Tim had said that Julie usually had lunch at her desk, so Neal wanted to get a look at the naïve hottie, and maybe give Tim a hard time in his office, asking him to call the secretary in and let Neal give her a spanking for some made up reason.

When Neal came through the front door, Julie was at her desk with a salad in front of her. Tim had described her accurately: blonde, blue-eyed, petite, and pretty.

"Hello, I'm Neal Roth. Is Tim - er, Mr. Johnson around?"

Julie pushed her salad to one side and said, "No, I'm sorry. He had a meeting with a client, and now he's at lunch. Did you have an appointment?"

"No, I'm an old friend of his from college, and I was just hoping I could catch him in." He told Julie about who he worked for, and said that he had a project that he wanted to pick Mr. Johnson's brain about. "You must be Julie," he said, sitting down on the edge of her desk."

"Yes, I am." She looked pleasantly surprised that Mr. Johnson would have told his old friend about her.

"Tim just hired you as his first employee, right?"

"Yes. My first day was this Monday, in fact."

"Well I think you made a good first impression on him. Picking your first employee is a big decision, and he told me that you are off to a great start."

Julie smiled, but felt a slight flush. "Thanks. I'm glad that he feels that way." It felt great to get a compliment, and to know that Mr. Johnson was happy with her work so far, but she wondered for a fleeting moment whether... Surely he wouldn't have told this man about smacking her bottom with a ruler, would he?

Neal smiled as he saw the blush on Julie's pretty face. She was cute! And between her shy, flushed smile and the little nervous movements of her hands on the desk, she gave away her thoughts as clearly as if she'd spoken them out loud. Neal got a sudden, sneaky idea.

"If this is your first week, I'm sure that he's still showing you the ropes, right?"

Julie nodded, not meeting his eyes. "There's so much to learn! I'm just trying to get used to the way that he wants his office run."

"There's always a learning curve in a new job," Neal said, waving his hand in dismissal. "Even though Tim's pretty young for a boss, and this is his first office, I'm sure that he's already teaching you the best practices that you need to work together as a team. Efficiency. Goal setting." He watched for her reaction. "Motivating employees through small rewards and punishments."

Julie's eyes instinctively rose to his for a moment, before she went back to her salad, her face once again flushed. "Yes, he's been starting to show me those."

Her reaction was perfect. Neal leaned in a little, and lowered his voice, even though there was no one else in the office. "How many mistakes have you made in a day so far?"

Julie was surprised again. "Three."

"Ooh," Neal said. "The ruler over the panties."

Julie quickly nodded, her thoughts in a whirl. She had suspected that Mr. Johnson had just been making up those office punishments, which caused two simultaneous reactions: a little tingle of pleasure that he found her attractive enough that he would scheme to get a look at her pantied behind, and a little resentment that he would manipulate her that way.

But to hear Mr. Roth talking about the punishments as if they were well known, and common practice, surprised her, and embarrassed her. She wasn't sure what to think.

"I remember my first day as a boss. My secretary was a little older than you are, and she'd worked for the company for two years. I knew the management techniques, of course, but I was a little worried about the punishment side of things at first. But my secretary made it easy for me. When she made her third mistake of the day, she said, "Don't tell me," before I could even say anything, and then she turned away and pulled up her skirt, and waited for me to get the ruler out.

"She did?" Julie asked.

"She did," Neal said. "She was very professional. I just whacked her bottom, and we got on with our jobs." It all he could do not to laugh out loud when he saw the thoughtful expression on Julie's face as she nodded.

Neal felt suddenly inspired. "I guess he's already told you about what happens if you make your fourth and fifth mistakes?"

Julie said, "He hasn't, but I was wondering about that." She felt the squirmy feeling down below again.

Neal smiled, and began speaking in barely more than a whisper. As he spoke, the pretty blonde's eyes widened in surprise. As he continued, her mouth dropped open, and she began to unconsciously squirm in her seat.

Fifteen minutes later, Tim returned from lunch, to find his old friend and his new secretary deep in conversation. "Neal, what are you doing here?"

"Oh hey, Tim." Neal got up off of the corner of Julie's desk and extended his hand to Tim. "I was in the neighborhood, and thought I'd stop in for a chat. At first I was disappointed that you were at lunch, but Julie here has been excellent company."

Tim shook his hand, and looked at Julie, who seemed a little flushed, but smiled at him. "Has she? I- I mean, of course she has."

"I told her that you have been singing her praises," Neal said. "And now that I've met her, I don't know that you've done her justice." He stepped back over to Julie, and shook her hand. "Miss Julie, it was great to meet you, and I hope I'll see you again soon."

Julie shook his hand and smiled, "That would be nice, Mr. Roth."

Tim watched this exchange curiously. "I'll walk you out," he said to Neal, and they stepped outside together. "What did you say to her?" Tim asked suspiciously.

Neal raised his hands in innocent protest. "Just the usual. How does she like working here, how are you as a boss? The usual."

"Tell me that you didn't bring up the - " he looked back over his shoulder toward the office, even though they were outside, and out of earshot, "... the ruler thing!"

Neal grinned. "Now that you mention it, that subject did come up."

"Oh come on! No! What did you say? What did she say?"

"Nothing to worry about, buddy. I reinforced the idea that all of us bosses are constantly motivating our female employees by increasing levels of discipline."

Tim looked confused. "What does that mean? What did you tell her?"

Neal laughed again, and slapped him on the back. "Not much. I just explained the escalating series of punishments, so that she'll know what to expect. She's a very motivated employee, and she really wants you to be happy with her work."

"Neal, what did you say to her?"

"You'll find out, Tim." Neal waggled his eyebrows, and turned to leave. "And you're welcome."

Tim watched his friend walk around the corner, and then he turned back to his office. Through the glass front door, he saw Julie sitting primly at her desk, and wondered what kind of mischief his skirt-chasing old friend had filled this young girl's head with.

Part 6

Tim walked through the open lobby area, nodding at Julie as he passed, and went into his office.

Julie watched him walking away from her. He was wearing business casual khaki pants, and they were just snug enough in the seat to suggest a firm, round rump. Julie found herself warming up a bit at the thought of what her boss' ass looked like under his pants, then she felt a little guilty. Then she remembered that he'd already seen a lot more of her butt, and she felt a little resentful.

Tim stepped into his office, closed the door behind him, and took a seat behind his desk. He looked up through his office window to see Julie turning away and picking up some papers. What had Neal told her? It was driving him crazy! He forced himself to do some actual work - reading emails, returning a few, making some notes - for over an hour. Every other time he looked up, it was as if he'd almost caught Julie looking at him.

What had Neal told her?!

Julie had similar thoughts going through her mind. She took care of some routine paperwork and filing, all the while sneaking glances into Tim's office from time to time. It seemed like he was looking out at her quite a lot; he'd almost caught her watching him several times. She thought about what Mr. Roth had told her, and squirmed in her chair again. Would her boss really do that to her, if she made another mistake?

Finally Tim hit the intercom on his desk. "Julie, could you bring the Cycle Wear report to me, along with a cup of coffee?"

Julie responded, "Right away," and she went to the closest file cabinet to locate the paperwork on Cycle Wear, a local female-owned clothing business that Mr. Johnson was hoping to snag as one of his first solo clients. She found and pulled out the file, and then put it onto her desk. Then she went to the coffee maker, and poured a cupful into Mr. Johnson's mug.

She was distracted, thinking about everything Mr. Roth had said during his surprise visit earlier. When it came to the coffee, she was mostly intent on not spilling it, as she held the cup in one hand, and the Cycle Wear file in the other.

She carefully walked over to Mr. Johnson's door, and more carefully turned the knob with the hand that held the file. Her tongue stuck out slightly between her front teeth, as she concentrated on not spilling a drop of the coffee, as she finally got the door knob to turn. She turned slightly to one side and bumped the door gently open with her left hip, and walked through.

Tim had watched her movement throughout the office, appreciating the rounded curve of her hips as she retrieved the file and poured the coffee. He thought she looked adorable with a slight frown of concentration and her tongue sticking out, and he didn't miss the sexy wiggle involved in her hip-checking the door open.

"Here you are," Julie said, as she stepped to his desk. The file," and she put it on his desk, "and your coffee." She placed the cup down, happy with herself at avoiding a spill.

Tim reached for the file and was pulling it open when he heard Julie gasp. He looked up, and saw a panicked look on her face, as she stared at the coffee cup on his desk. Tim looked at the cup, hoping he'd see that a few drops had splashed onto his desk. But there was nothing there, and he felt a tangible disappointment as he looked back up at—

The coffee! Tim looked again, and saw that it was true. He looked back up at Julie, who lifted her eyes to his, a gorgeous look of consternation on her pretty features. "I- I-," she stammered.

Tim allowed himself a very small smile. He thought, "It's too bad that this is only her first mistake today, and there are only around 3 hours left in the work day." But it wouldn't hurt to reinforce the rules of the game that he'd been playing with his pretty employee. "I think there's something missing, Julie."

She nodded, staring nervously. "Your cream. I forgot."

"It looks that way," Tim said. "We both agree that that counts as a mistake, don't we?" He was rubbing it in a little, but it seemed like she was over-reacting. He was just about to say that he was going to have to rap her knuckles, but she spoke first.

"Mr. Roth told me about the cumulative punishment system," she said, sounding almost frightened.

Tim thought, "What the hell? The cumulative punishment?" But out loud he said, "So I don't need to explain that to you, then?"

Julie hung her head and looked at her shoes, and said, "No," in a very quiet voice.

Then, as if she were reciting the exact wording of a rule, she said, "During my first two days of training, I started with a clean slate each morning. But starting yesterday, my mistakes would accumulate over the rest of the week."

"Yes," Tim said, his mind racing. "So that means that this mistake was your..."

"My fourth," Julie moaned.

Tim smiled again. "And Mr. Roth told you what that means, didn't he?"

Julie nodded, not trusting herself to speak. She stepped tentatively to the front of his desk, and leaned forward over it. She reached back with both hands, grasped the edges of her snug business skirt, and tugged it upward. Tim stood up and walked around beside her, in time to see her use a few sensuous hip wiggles to help ease the pencil skirt up over the roundest part of her luscious buns. As he took his position, she wordlessly leaned over his desk a little farther. He expected her to flatten her arms on the desk, but instead she reached back behind her again.

Tim sucked in a small breath soundlessly as she grabbed both sides of her panties - yellow cotton ones today - and pulled them upwards. Like the world's sexiest magic trick, the material bunched together, and then slipped into a thin strip that almost disappeared between the two pale, smooth globes of her fantastic ass.

She leaned forward again and put her forearms on his desk, which obscenely thrust her almost totally bared butt outward.

Tim cleared his throat, and said, "Did Mr. Roth tell you how many spanks you get for a fourth mistake?"

Julie's voice was low, muffled even more by the fact that she was staring down at the desk in front of her eyes. "Five per side."

"That's right," Tim said. "So, 10 total." He rubbed his hands on his khakis, then turned and walked back around the desk, pulled open the drawer, and came out with the ruler in his hand. Julie's blue eyes locked onto the ruler, and she turned her head to follow it as he moved back into position beside her.

He said, "Okay then. Let's get—"

"Mr. Roth said your hand," Julie interrupted. She was looked back at him, over her mostly bare behind. "He said the ruler would hurt too much... on the b- bare... On my bare... behind."

Tim froze for a moment, looked at the ruler in his hand. Then he recovered. "Oh, that's right. I forgot that the fourth mistake calls for a hand spanking." He put the ruler on the desk, then gave Julie a small smile. "Lucky for you that Mr. Roth explained the rules to you. Otherwise I would have forgotten, and that ruler would have really stung."

Julie blushed. "Yes, Mr. Johnson." She looked back at the desk.

"Did Mr. Roth mention that you should count the spanks?" Tim said, playing a hopeful hunch.

"Yes," she said. "And that I should thank you after each one." She was really blushing now.

Tim thought, "God bless you, Neal Roth!"

Barefan
Barefan
268 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousalmost 4 years ago
Delightfully naughty

This is a lovely kinky story and thankfully not as vicious as the blackmail sex type of stories.

I much prefer stories with a female submissive as opposed to your other story.

Thanks for sharing

Tess (UK)

AnonymousAnonymousabout 4 years ago
Mooore

Hi, this is very good in my opinion, do please continue soon!

AnonymousAnonymousabout 4 years ago
Mistakes

When I was a boss at the restaurant after three mistakes they bent over and pulled their skirt up but I didn’t spank them. Loved how wet some would get.

Share this Story

Similar Stories

A Very Personal Assistant Manager harasses his busty not too bright new assistant.in NonConsent/Reluctance
Claire's Christmas The Busty Redhead goes to work as Mrs. Claus.in NonConsent/Reluctance
Tricking the Cheerleader A lucky loser meets a ditzy cheerleader.in NonConsent/Reluctance
The Stupid Secretary Can Todd take advantage of his stupid secretary?in NonConsent/Reluctance
Teams Colliding Pt. 01: Bus Ride Forced to share a crowded bus, Anne gets screwed.in NonConsent/Reluctance
More Stories