Guess Who's The Boss? Ch. 01

Story Info
William meets Jenna, and visits an old friend and sub.
2.8k words
4.35
12.6k
7

Part 1 of the 2 part series

Updated 06/08/2023
Created 05/02/2017
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

"I've tried writing a book," she exhaled, "but I've never quite gotten to finishing it."

The man behind the desk nodded, scribbling something down in his expensively bound leather notebook before looking back up at her.

"And why do you think that is?"

"What is?"

"Your inability to finish things you start."

Her mouth opened in surprise, taken aback by the question.

"It's not like I leave everything I start halfway through..."

He nodded again, muttering something under his breath and scribbling away. He then stood up, holding out his hand.

"Thank you for your time, Miss Rogers. I think I have everything I need."

Jenna was on her feet in no time, well aware that like the others, this session had been a sinking ship since the moment she walked into Mr. Brown's 20th story office. She politely shook his hand, gathered her things and walked out the door of Ice Publications, probably never to return.

~

He watched her pack her things with the same keen eyes that he watched her with when she walked in. "Jenna Rogers," he thought to himself, "has one amazing body."

She leaned over his desk when he handed her her portfolio, her ample breasts straining the buttons of her shirt. It didn't help the poor satin thing that she wore her shirts a size too small, something he had noticed whenever he saw her in the hallway, as she was working her way up to the coveted interview with the CEO.

Her pencil skirt was just long enough to be called decent, but it rode up her thighs when she sat, leaving him with nothing to complain about as a man, and the growing discomfort in his pants was testament to that.

But as a boss, boy was she disappointing.

William was sure to walk her to the door, being the gentleman that he was, taking the opportunity to check her out from the back. Her hair cascaded down to the small of her back, the flow of curves picked right back up by her ass. No wonder her skirt was acting up.

The sound of her heels was muffled by a carpet that had muffled much else, but the way they made her calves look made it more than obvious that she took time out to work out, and that made him happier.

As he closed the door and headed back to his desk, his eyes glossed over the emails his juniors are written him, detailing what a wonderful candidate Ms. Rogers was for the position they were considering her for. One email even said, very boldly, "Her assurance in her talents and abilities is just the right amount of smug, far below the borderline of overconfidence."

All the employees spoke so highly of this woman that it confused him. This could not be the woman that walked into his office today. That woman was nervous and flustered, and completely unfit to be bossing people around.

He clicked the attached copy of her portfolio.

Assistant to Inaya Langford at 'Talk of the Town'.

Inaya? William scoffed.

He shut his laptop down, and picking up his phone, he stepped out the door.

~

The driver was cursing the car in front of theirs, and the car in front of that one, and the car in front of that one. Jenna was cursing him. She knew they should've taken the highway, and despite making it abundantly clear that he should listen to her, there they were, stuck in an endless queue of traffic.

It surprised her how quick she was to recover from the calamity of an interview that she has just given, snapping back into her outspoken self, mere moments later. She didn't know what changed when she walked into Mr. Brown's office, and if it was the coldness of the office space that chilled her to the bones, or his gaze.

From the moment she walked in his door, he looked at her in a way that made her afraid of him, in a way. He was detached and to the point, power just flowing out of him, and that intimidated her to her breaking point, and even after all the late-night preparation, all that was left of her was a flustered mess.

"Idiot," she muttered under her breath.

"Nobody said you have to sit through it. I have hearing aids, and I can hear everything but your thoughts. No need to call names, so get out before I kick you out."

The cabbie suddenly thought his opinion mattered.

Jenna opened the door and leaned over to the driver's ear, her voice almost a whisper, "Listen up, you little shit. Maybe if you'd used those aids to hear me tell you to take the highway instead of letting your deeply rooted tendency for being a misogynistic asshole cloud your senses, we wouldn't be here. So instead of eavesdropping on what your customers say, try your ear at listening to a woman, for once, because it seems like you aren't capable of making any decisions of worth on your own."

With that, she was gone, down the stairs, to the subway, and late for work.

~

"I didn't know you had an appointment. But then again, I don't know shit without my assistant, and she seems to have conveniently disappeared."

"I was in the neighbourhood, and my next meeting is way after lunch," William said, as he walked into the office of Inaya Langford. "Besides, I hadn't checked up on you since the last time we met... about a month ago?

Inaya slapped his shoulder, letting out a chuckle. "You tease."

"Meeting way after lunch," she continued, "What's wrong? Is your company losing business?"

William raised an eyebrow at the brunette, her face still glowing like it did fifteen years ago when he saw her for the first time. She noticed his gaze on her, just the way he knew she liked it, and as much as she tried to hide it, the growing pink on her cheeks betrayed her.

"Aah! She's texted me. She's running late, but thankfully she's almost here and I have no appointments till..." her voice trailed off.

"Till?"

"Lunch."

That elicited a laugh from even him, and the two of them headed to the couch.

William sat down. "Still as comfy as ever."

Inaya's expression changed from jolly to borderline cocky, and he could see that out of the corner of his eye. He wasn't going to look at her, though. Instead, he chose to stare out of her window, watching the traffic crawl down the street.

A knock on the door startled her, and a rough "Come in!" was spurted out, before Inaya got up to greet a woman, he assumed, with the scent of a familiar perfume filling the room.

That's when he heard the voice that had impressed so many people, and his best friend, before him. He couldn't help but smile.

"The reports are back from the audience poll that we took on our latest publication, 'Sky,' and before you look at them, I have to tell you that it is my opinion that they are completely bullshit. At least the analysis is. There is not a chance in hell that 'Sky' is a book that lacks creativity and elegance, and the readers aren't stupid enough to want a supernatural story with a message wrapped around a romance, because if they do, they need to get out of their 15-year-old mindsets and think about what they really want. Overall, we either need new polling people or new analysts."

William stood up, walking across the room as Inaya walked to her phone and dialled an extension. "Analytics?"

He used his walk wisely, choosing select areas to focus on, sizing up the 27-year-old as he made his way towards her. His mind was made up, and the boss in him knew his next move.

~

She only heard him when he was a foot away from her, and quickly turned, her eyes widening in horror. Her mouth opened just a little, and that is when she actually saw him. "Sitting behind a desk does this man no good," she caught herself thinking, "He should probably just always stand."

William Brown was 6'2" with the body of a sculpture. You wouldn't notice his build under the three layers of formal wear he put on, but you'd be blind if you didn't notice the way his biceps curled under his jacket when he ran his fingers through his hair; and that was just what he was doing as he walked over to Jenna.

He loomed over her 5'7" frame, eyes as if they were staring into her soul. Sure enough, her throat dried up. Desperate to not make a fool out of herself, she swallowed the sense of déjà vu and barely got a bit of a word out of her mouth before her boss returned.

"Jenna dear, meet William Brown. He started 'Ice' before 'Talk of the Town' managed to stand up on its feet, and the two-month head start has been a pain in my ass ever since, just like he has."

"Will," she went on, "this is Jenna, my assistant, and one of the brightest and most outspoken minds here at TTT, and a real valuable asset. You'll like her."

He shook her hand with the same strength that he did that morning, except this time, she felt something terribly inappropriate. "Maybe he's better off behind a desk," Jenna thought.

"Well, I'd love to get to know her, and she deserves my appreciation for being able to sort out your very busy schedule, I."

Jenna's boss rolled her eyes.

"She should." He took a card out of his wallet, and walked over to Inaya's desk. Writing something on the back of it, he handed it to Jenna. "Call me if you need anything."

Jenna looked at Mrs. Langford, for answers or reassurance, she didn't know, but, "you can go now," was all she got.

She balanced the files in her arms and pushed the door open, dumping them all on her desk when she reached it. She sat at her table and looked at the card lying amidst the mess. Picking it up, she read, 'William Brown, CEO, Ice Publications.'

She scoffed. Who didn't know who he was? She turned it over, and written in the neatest handwriting she had ever seen was, "Dinner. I'll pick you up at 8."

~

As soon as Jenna was out the door, Inaya turned to William.

"Why are you really here, Will?"

The cockiness was back, and this time, he did look at her.

"What do you think I'm here for, I?"

She walked up to him, not before locking the door first, and kissed him, full on the mouth, her hands in his hair and his hand in hers. His other hand trailed down her neck, almost caressing her, and he waited for a moan to slip the lips he was devouring.

In the snap of a second, the hand in her hair was tugging her head back, hard, and his other hand was firmly wrapped around her throat, reducing her to a gasping plaything, just the way he liked her.

He eyes closed as he tightened his grip on her hair, and her heard a little whimper. Oh yes, he was going to make sure he got more of those. He loved to hear her whimper, and although he had gotten off seeing so many men fucking her, his favorite was when he was the one making her body make that carnal, helpless sound.

His fingers left her throat and grabbed her bottom lip, pulling on it until her mouth opened. Without wasting a moment, his fingers were in her mouth and down her throat, hindering her attempts at both moaning and screaming, and the hand still in her hair ensured no struggle.

He pulled his fingers out, pulling her head back as he as returned his hand to her throat. He held her there, firmly, as he ran a finger across her lips and then onto her cheek, smudging the fiery red lipstick that she wore.

"You do not have the privilege of kissing me until I say so. I thought I made that clear."

Inaya nodded, frantically.

"Yet here we are," he said, pulling out the neatly tucking in flimsy mesh shirt she wore. "Mistakes and more mistakes, I. I'm starting to believe you like being punished." He pulled her skirt up, a difficult task pulling it over her round ass, and delivered a sharp smack against it, the only thing stopping him from hitting skin, her stockings.

He took her to the couch, moving his hand to the back of her head as he guided her there, and in one swift motion, he pushed her to it, causing her to stumble and land bent over the back of the couch. His hand returned to her hair, and when she tried to get up, another sharp smack silenced her struggle.

He grabbed a handful of her ass, delivering repeated smacks on the other cheek, one after the other, not even stopping enough to let it stop bouncing. "What did you do, I?"

"I overstepped my bounds."

Smack.

"It's funny how I can hear you whimpering, but not talking."

Smack.

"I overstepped my bounds," she said, a little louder, followed by a scream this time, as the crack of William's belt on her ass filled the room.

He looked down at her writhing body. Her pale skin shone in the sunlight, and her legs had spread a little every time her ass was struck. She was so responsive it drove him crazy, her body all but screaming it out loud when he did something that pleased her, making the task all the more enjoyable.

He knew she wasn't wearing any panties long before he lifted her skirt up, so it wasn't impulsive when he kneeled down and ripped her stockings with his teeth, standing up and tearing them further, until her ass flowed out, perfectly round, and still not sagging, even in her thirties. He tore them a little further, exposing her wet pussy to the cold air conditioned air, and he let the goosebumps that appeared down her legs be indication of when to stop.

William unbuttoned his trousers, throwing his phone on the couch, beside Inaya's head. He moved his hand up her waist, stopping to grab her by her 32DD breasts, leaning down and pulling her up as he pressed his dick against her.

She put her hands on the seat and let out a whimper as he pinched her nipple. His fingers were in her, hooking and tugging, making her squirm. He was getting impatient, and just as she began to tense up, he pulled them out, pinching hard, and bringing his fingers to her lips. She didn't hesitate before sucking on them, and managed to get a grunt out when he pushed into her, all 7 inches of him.

He leaned over her, biting her ear and whispering, "Do I hold your hair or your tits when I fuck you so hard you beg me to stop?"

Inaya ignored that question, making another mistake as she pleaded, "Please let me come! Please!"

Another smack.

William began to pump, slowly at first, and when Inaya started to moan, he picked up his pace, going faster and deeper with every thrust. He felt her tense up, and after the years he invested in training her, he knew she could control herself.

"Don't you dare," he reminded her, hitting her ass harder, looking at and loving how red and warm it had gotten. He wasn't done toying with the bitch, and there was no way in hell he was going to let her go this easy.

He grabbed her breast, pinching down on her nipple, hard, as he continued to thrust into her, and didn't realise how hard he'd been pressing as he slipped into the ecstasy of Inaya's timelessly tight pussy, until she screamed, and that shrill, powerless shriek of hers was all it took to push him off the edge, and he closed his eyes as he emptied himself out into her.

"Come for me baby."

Three thrusts later, Inaya joined him, moaning, as her whole body convulsed with her orgasm.

He pulled out and put his pants back on, picking up his phone and tossing the woman over the back so that she lay on the seat, with torn stockings and no panties, a disaster for someone who just got fucked without a condom. He didn't regret it.

"Next time onwards, kiss your husband, I. It'll save you some clothes."

Running his fingers through his hair, William walked to the door and opened it, sending Inaya scurrying to tidy herself up.

"And tell him I said hello," he added, closing the door on his way out.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousalmost 7 years ago
Nice start

looking forward to reading the next chapter

Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Dom's Best Friend Ch. 01 Two old friends secretly yearn for D/s relations togetherin BDSM
I'll Do Anything, Sir A lawyer forces his secretary to an agreement on his terms.in NonConsent/Reluctance
Learning the Rules Ch. 01 Novice meets soon to be Teacher.in BDSM
Compromise A husband desires control in the bedroom.in BDSM
Raw and Broken Ch. 01 Daphne's story.in BDSM
More Stories