The Assistant (Part 1)

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Status: Finished  |  Genre: Literary Erotica  |  House: Booksiesilk Classic Group

Janelle expects perfection from her new assistant and will not hesitate to punish him until he reaches it.

“Yes?” Janelle called when there was a soft knock on her closed office door . She tried to keep her voice light and not show how irritated she was at the intrusion. It was well before nine a.m., and she didn’t expect anyone else to be in the office. This was her time to drink her coffee (two creams, no sugar) and go through her unread emails. She liked to have both finished before she interacted with anyone. 

She scooped her waist-length braids to one side over her shoulder so they fell against her right breast. It was something she did out of habit when she thought she would be meeting with the CEO, who told her once that she liked it when Janelle put her braids that way.

Her door creaked open. That was the only problem with being in an old, converted building. Besides all the doors and floors that creaked, there was no modern design like glass walls and doors that could be tinted. None of the building’s décor was to her taste—from the exposed pipes in the ceiling to the exposed brick wall opposite her desk. Also, the offices weren’t very big. “We give you big homes, not big offices,” the CEO told her when Janelle was hired five years ago to fill the executive position.

She barely glanced up from her email at the young man who stood just inside her doorway. She was mildly disappointed that he wasn’t the CEO. “Yes? Can I help you?” she asked, her voice taking on the customarily stern edge.

“Um, I’m your new hire?”

Janelle made a neutral noise and continued typing her email.

“We, ah, we talked on the phone the other day?” he added when a few seconds passed and she didn’t jump up to welcome him. “I’m sorry you were out of the office when I came in to meet the rest of the team during the final stage of the interview process?”

She paused in her typing long enough to wave a dismissive hand at him. “Fine. You’re here early.”

“Yeah, ah, you asked me to get here before eight.”

She stopped typing again and scowled up at him. “I don’t recall our conversation, but if you say so. Have a seat.”

He perched on the edge of the stiff chair across from her desk. She didn’t like the nervous energy he gave off and would allow him to stay in her office for another ninety seconds before she dismissed him. “What’s your name?” she asked, going back to typing as she talked, the clatter from her keyboard filling in any awkward silences between them.

“Um, Kai.”

“Well, Um Kai, my job is to groom you for your next position so you’ll be ready to move up within our organization. If you work hard and apply yourself, this process can take eight to twelve months. You’re up against other assistants in this organization, and I want you to succeed. First thing, I expect you to speak with more confidence. So, I’ll assume your name isn’t Um Kai, but Kai. Second thing, stop making everything you say sound like a question.”

“I do?”


Kai laughed nervously. “I see what I did right there.”

So, he has a sense of humor. Janelle finally stopped typing and looked up at her new assistant.

“I like that you’re clean-shaven. You have a nice face.”

He blushed and then glanced down at his lap.

She was pleased she could get such an immediate reaction out of him. She didn’t like it when her assistants were hard to read. She also liked that he was giving off Boy Scout vibes. When she was younger, she only fell for bad boys, those with fast vehicles, or weed or arrest warrants. If they had all three, it was a bonus. But now that she was in her forties, she gravitated toward the opposite. Janelle shifted in her seat as her panties began to moisten as she talked to Kai.

“Yes, I said that out loud. You’ll quickly learn that I don’t sugarcoat what I’m thinking. If you didn’t have a nice face, I would probably tell you that too. After all, we’ll be working long hours together, and I’m the one who’ll have to look at it.”

Janelle held his gaze, challenging Kai to bolt out of her office to HR. But then his shocked expression changed as the corners of his mouth turned up, and he laughed. He relaxed against the back of the chair when he did. “That’s good to know that I fit aesthetically within your working environment.”

Janelle smiled for the first time. “So, you’ll let me know now if my directness bothers you? If you think you need to report me to HR, please have the balls and courtesy to tell me first. I don’t fire people for stupid reasons because they didn’t like it when I complimented them or thought I was standing too close. I fire them because they’re bad at their job. Good assistants that do what I need them to do are way too hard to find.”

Kai nodded earnestly. “I’m a hard worker. I worked full-time while I was going to college and graduated magna cum laude.”

Janelle sat back in her ergonomically correct chair and assessed him further. “How old are you?”


She nodded again as if filing this away. “You’re a little old to be right out of college.” Despite this, Janelle calculated that she was still old enough to be his mother if she had him when she was eighteen.

Kai dropped his big eyes again. He really did look cute when he did that, but this no-eye contact thing that he did would prevent him from being a good assistant.

“You should look people in the eye when they speak to you,” Janelle said. “Unless it’s me, and I tell you otherwise.”

Kai looked confused for a second, as if trying to understand when she would tell him not to look her in the eye. “Um, sure,” he said before he dropped his gaze again.

Janelle had to suppress the urge to stalk around her desk, take a clump of his fine, brunette hair in her fist, and force his head back, so he looked her in the eye. Patience. It’s only his first day. The first hour even, she reminded herself.

“Your eyes,” she said in a firm voice.

He snapped his head up. “Right. Yeah. So, you wanted to know why I just graduated?  started college a little late? My dad died suddenly during my senior year of high school, a heart attack, and my mom was a mess. We both were. I didn’t want to go on to college and really just wanted to burrow under the covers and sleep the rest of my life away. I made some bad choices with prescription meds to stop some of the pain and loss I was feeling but got help, and finally went to college like my mom begged me to do.”

“Your mom seemed pretty influential in your life.”

Another smile from him. Janelle liked how his smile went all the way up to his blue-gray eyes and seemed to make them light up. “If I had lashes like yours, I would be able to save myself at least ten minutes in the morning during my make-up routine,” she murmured.

“Excuse me?”

She shook her head. “Nothing. You were going to tell me about your mother.”

“Yeah. I don’t know what I would do without her. She’s my best friend and taught me everything I know. She and my dad that is. I miss him,” he added quietly, his face solemn.

The conversation was getting too heavy for Janelle. She was fearful his eyes, which reminded her of looking up into the sky on a cloudy day, would become misty. She tried to lighten the mood. “So, you’re a Mama’s Boy, are you?” She was curious to see if she could get a rise out of this Boy Scout, but he shrugged.

“Yeah, I guess so. She’s an amazing woman, and I admire her. You know, she always wanted to be a professional woman like you and work for a multi-billion-dollar corporation. But she became pregnant with me freshman year of college, dropped out, and never went back. She ended up picking up odd jobs and always made sure she was home to help me with my homework.”

Janelle decided she liked his mother. They were probably in the same peer group, and she thought they could have been friends in another life.

“Okay, Kai, thank you for the background story. I like you more already. Now let’s get to work.” She rose and carried a file of papers around her desk and sat on the corner of it, a few inches away from Kai so she could show him what she needed him to do. The tip of her black heel with the red bottoms barely rested against the top of his brown dress shoes. His shoes looked new, and he probably purchased them just for this first job. She suspected the suit was new too. It fit him well and looked good on him.

When she was finished, she looked up at Kai to make sure he understood. He quickly shifted his gaze from her breasts and up to her eyes.

Oh, did I just catch you looking? She’d forgotten when she leaned forward like that her cream-colored blouse billowed out in front of her. He’d gotten a good look at her C-cup and white lace bra that contrasted against her dark skin.

“Do you have any questions?”

“Um, no.”

Was he now looking at her legs? They were bare and peeked out from under her black leather pencil skirt. She’d been a runner in high school before a knee injury ruined any chances of her competing at the Olympic level. Despite that, Janelle still went for a daily run. She’d conducted her share of conference calls while jogging around her neighborhood or on her treadmill in her basement.

“Are you sure you don’t have any questions?”

“What else does the job entail?”

Janelle uncrossed her ankles and gave him another thoughtful look before she said, “Kneel.”

His brow creased into a frown.

Janelle leaned over Kai and placed her hands on the armrests on either side of him. She was close enough that her long braids grazed his chest. She could see flecks of brown amid the gray in his eyes spark to life. He looked like a trapped rabbit, and her sex immediately responded to his fear. She liked when she could evoke that look from her assistants.

“If you’re going to have a problem with following directions, then you’re not the right fit for this position, and you’ll want to leave now,” she said.

His Adam’s apple bobbed when he swallowed. Then a hard, determined look replaced the fear in his eyes. “It’s not going to be a problem.”

She stepped back so her assistant could slide off the chair and onto the floor. He knelt in front of her. His head came just to her middle, and this pleased Janelle. She could easily lean back on her desk, draw up her skirt and pull his face into her sex. But that was for another day, after she broke him in.

She touched the top of his head with her fingertips. “Good. There may be times when I ask you to kneel when you’re in my presence. Will that be okay with you?”

He swayed, blinked up at her, and then nodded.

“Say it.”

“That’s okay with me if you want me to kneel when I’m in your office. Uh, presence.”

“Perfect. I think we’ll make a great team. You can get up now. I have an eight o’clock,” Janelle said as she settled back behind her desk. “Shut the door when you go.”

He was slow getting up as if it was a trick or he expected something else from her.

“You will need to move faster than a snail’s pace,” she said, gesturing with her hands that he needed to rise.

“Sorry, sorry,” he said as he bounded up, and his face grew crimson. “I just wasn’t sure if you wanted … needed … I don’t know, something else?”

Was he alluding to what she had been thinking? The thought of his tongue playing with her clit made her recross her legs. She would love for him to service her, but work always came first. She didn’t make it this high up in the corporation by giving in to every carnal urge.

Her features softened as he looked at her with sincerity. “No, nothing right now. Thank you,” she said, waving him off.

Her assistant stepped through the door but then turned and poked his head back in. “For what it’s worth, you have a nice face too.” And then he was gone.

She smiled to herself but then scowled. She hated when her assistants got in the last word. Janelle took a moment to jot down on a pink Post-it a note about her new assistant: Needs a good spanking. She underlined her neatly written words twice before getting online to join her meeting.

Check out my Patreon ( to become a member and read Part 2.

Submitted: February 08, 2022

© Copyright 2022 j.l. jenson. All rights reserved.

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