The Assistant: Owned by the Boss

This work is a collaboration with Nothinglefttoburn.

She was an absolute delight to work with, and helped make this story so much hotter and more enjoyable to write. Seriously, she made exploring the darker side of my writing so much fun! You should really check out her works, they are very hot and enjoyable!

We are also planning on continuing this story. Let us know if you want more.

Please let us know what you think of the story, feedback is always appreciated.

Obligatory all persons are over 18.

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"Fuck, fuck, fuck," Becca muttered under her breath, as loud as she could, given that several people were sleeping within feet of where she stood. She was brushing her hair and attempting to get dressed at the same time, yanking a brush through her matted hair and stepping into a tight pencil skirt. She stepped over her roommate's boyfriend, who was sprawled on his back with his shirt off in the middle of their living room, to get to her heels and slipped them on, heading for the door without even bothering with makeup. What's the point? she thought miserably, I'm just going to get fired anyway.

She was late for work and couldn't find her cell phone. A major problem, considering she had an extremely important client call scheduled 10 minutes from now. She was supposed to be behind her desk at this very moment, not pretending to be James Bond dodging laser beams, tiptoeing over drunken idiots in her apartment. She tried to wake her boyfriend Alex, who was sleeping on the couch, but he just grunted and rolled onto his other side. I'll tell him later, she thought, kissing his forehead, and then rushed out the door.

+++

Pulling into her parking spot at work, Becca let out the breath she'd been holding since the moment she woke up. She had no phone, looked like shit, and was probably about to lose her job, the best paying one she'd ever had. She thought about the climbing balance in her savings account and how just last week, she and Alex had started looking at houses. Now those dreams were definitely dead. A flash of her father's face when she broke the news nearly made her back out and drive to the nearest bridge to fling herself off of it.

Somehow she gathered the strength to open the door and walk into the office building. She decided that instead of heading to her office, it would be best to just go straight to Mr. Anderson's office and get it over with. Maybe I could beg? she thought desperately. The thought started as a joke with herself, but as she stood in the elevator, it started to blossom into something more.

No two ways about it, Becca was a beautiful young woman. She had never had problems getting men, in fact, she had problems fending them off most days. Mr. Anderson had never been outwardly inappropriate, but she had definitely felt his eyes linger on her ass or cleavage more than was probably acceptable for a boss -- especially one twice her age. Begging was actually beginning to sound like a viable solution to this mess.

Becca reached the 19th floor and stepped off the elevator and into the reception area of the corporate office at which she was (at least currently) employed. She made a beeline for her boss' office, ignoring her coworkers' waves and friendly hellos, feeling like an asshole but knowing stopping to chit chat would make this so much worse. She raised her fist to knock on the door labeled BOB ANDERSON - CEO, but stopped short when the door suddenly opened and she was face-to-face with the CFO, Mark Thorpe.

"Mr. Thorpe," Becca said in a strangled voice. "Good morning!" She tried to inject an air of casual cheerfulness into her tone, but she just sounded squeaky.

"Miss Ambrose," he said with a twitch of his eyebrow. He looked over his shoulder into the office. "Bob, looks like one of your girls is here to chat," he said with a laugh, pushing his way past Becca and out the door.

Becca stepped into the office as he left and shut the door behind her. She was seething from the "one of your girls" comment, but obviously there was fuck-all she could do about it. She plastered her most charming smile on her face and approached Mr. Anderson's desk.

His eyes were glittering with happiness for someone who should have been angry.

"Miss Ambrose...Becca, right?" he said with a grin. "How did the SureTek call go?"

She nodded, confirming her identity. "Yes, Becca. Um, actually, that's what I'm here about. I, uh, unfortunately, missed their call this morning and... well, I know from the past several meetings we've had that they won't be rescheduling. I'm fairly certain we... I... lost their business. Sir." Her face was red-hot, and her palms were slick with perspiration.

Mr. Anderson's face remained pleasant, which was somehow scarier than if he had transformed into a monster at her admission. "I already know about the call, Becca. And that you're over an hour late. And that this is the third time you've been this late. I honestly think we need to have a serious discussion about your future here," he said. His serious tone did not match his gleeful demeanor.

Becca took a deep breath, pushing down the tears that threatened to spill over. "I know, Mr. Anderson, and I am so incredibly sorry, I promise to do better from here out. And I'm willing to do...whatever it takes to stay in my position here," she said, meeting his eye deliberately, trying to convey her exact meaning without having to say it.

"Whatever it takes, Becca? Do you really mean that?"

+++

Bob was extremely pleased. He could have kissed that hairless old bastard at SureTek when he called.

Bob had been eying Becca for some time. He liked his whole "....Becca, right?" He had known her name since her second day when he had seen her bending over to retrieve something from the drawer in her desk and her delicious ass had been up in the air.

He knew everything in her file, and more. Once his secretary, Amanda, had told him the office gossip, he knew the last piece of information he needed to know that informed his decision to make her his own once the time came.

She had a boyfriend.

Some execs craved money. Some craved power. Some craved pussy.

Bob craved all three, of course, but pussy was the number one thing he wanted. But specifically, he craved a pussy that belonged to another man, whether it be a loving boyfriend or husband.

To Bob, the greatest pleasure in life was to have a woman willingly submit to him (Bob didn't consider a bit of coercion as force at all), let him humiliate her, then send her home to her faithful spouse with his sticky cum leaking from her sore asshole, her well worn cunt, and still on her breath as she kissed him.

Bob laughed quietly to himself as Becca stood there, trembling, though she was having difficulty telling where the trembling was from fear or excitement as she felt Bob fucking her with his eyes as they roamed all over her hot young body, stopping to openly stare at her chest.

The bastard didn't even try to hide it!

"Sir?" She tentatively asked, only to stop as he raised his hand in contemptice dismissal.

"Miss Anderson. You will remain there while I put my thoughts in order. You will remain silent. You will remain still, except for when I ask a question or instruct otherwise. Am I understood?" He asked calmly, voice chill and commanding.

Becca nodded, squeaking out a "yessir" as she blushed.

Why the FUCK were her panties getting wet? She knew what she was going to offer, but she sure as shit didn't plan on enjoying it!

Bob went back to his ruminations.

He laughed internally. He knew he wasn't a good man. Or a just man. Fuck. Justice was just for people who couldn't take what they determined was theirs.

Hell, his secretary Amanda called him Daddy when no one else was around. He WASN'T her Daddy. That was Todd Philips in accounting.

But Todd had gotten caught hiding mistakes, caused by his daughter, so Bob had taken her much like he would take young Becca here, to save both her and her father's jobs.

When she started calling Bob Daddy while he was balls deep in her tight pink asshole, of her own volition, he had gotten that moment on tape. She had begged him to take her asshole to show him she belonged to him, as she would never let her wimp of a husband to do.

Bob had taken a ghastly glee in sending that video to her father AND her husband. He gave her a raise after that, since her husband had divorced her and left town.

Those thoughts and the young, terrified woman standing in front of him had Bob at full mast inside his pants.

11 inches of iron hard flesh, as big around as a coke can,was ready to plunder this trembling cunt and make her his as it felt like it nearly lifted his desk from the floor.

"You really mean anything, Miss Anderson?" He asked again.

She started as she realized he expected an answer.

"Yes, sir!" She said softly, possibly rethinking this in his intimidating presence.

+++++++++++

Bob leaned forward on his desk, stared at her for almost a full minute silently, and then simply said "strip."

Becca looked back at the door, worried that someone could come in before she remembered whose office she was in, and that nobody would dare to just bust in.

"You did say ANYTHING, Miss Anderson, did you not?" He questioned coldly, his eyes like ice.

"THEN STRIP, CUNT!" He barked, a commanding voice normally reserved for long term military members.

Amanda, startled and frightened, began to quickly shed her clothes.

"Ah, ah, ah!" He said, shaking his head pleasantly, "Slowly. Make it worth my time."

Becca slowly stripped, imagining a popular dance track in her mind that she had stripped to for Alex on multiple occasions.

She slowly writhed and twisted, getting lost in the naughty memory, realizing what she was doing as she bent over double in Mr. Anderson as she slowly peeled her wet panties from her soaked pussy and brought them down and over her heels.

She stood there with the soaked panties in her hand, not sure what he wanted next, only then noticing the multiple webcams throughout the office, the lights indicating each of them were on, and she was naked with her cunt soaked panties in front of them.

She hadn't been prepared for him to lean back in his desk, unzip his pants, and pull out what must have been the most imposing pillar of fuck flesh she had ever even contemplated.

11 inches of solid man flesh jutted obscenely from his pants as he placed his hands behind his head and looked expectable at her.

"Now, Miss Anderson, this is a negotiation, like any other, just with different bartering tools. Come show me what YOU think anything is. Then I will inform you of my what counter proposal of anything is." He said, with an arrogant tone that told her he knows she will do whatever he says, but is just enjoying the game so far.

Everything happened so fast, Becca hardly had time to establish that this was actually real, and she was, in fact, fully nude in her boss' office with her (confusingly soaked) panties dangling from her finger. Also, her 50-something year old boss apparently had a literal horsecock, which was equal parts intriguing and terrifying. So that was something.

She was supposed to be negotiating the terms of keeping her job, and something told Becca that he would not settle for a strip tease and a handjob. She decided her best bet was deference. Submissiveness. She took a deep breath and reminded herself of what she had to lose.

Becca approached him behind his enormous desk -- *definitely not compensating for anything, though,* she thought idly -- and dropped to her knees next to his chair. She didn't meet his eyes, instead gazing at his chest, trying to keep herself from staring directly at his incredibly large dick. She was even more terrified of it up close. She heard him make a satisfied sound. Bob Anderson was easy to read -- he wanted power, and he was not someone who would handle brattiness or backtalk. So Becca sat, still as a statue, and waited.

Finally, he spoke. "Look at me," he said, and his tone was gentler than it had been before. Becca tilted her chin up and met his eyes from under her long lashes.

"What are you offering me, Becca? Hmm? Use your words. Don't be coy or shy, I want to hear it." He said. There was no room for negotiation, really, when it came down to it. Whatever she offered, short of *everything*, wouldn't be enough.

She shifted on her heels and licked her lips. Her mouth was suddenly very dry. She dropped her gaze again. Before she could speak, Mr. Anderson's large hand was gripping her chin, yanking her face up. "Look at me when you speak," he said.

She nodded and Bob leaned back in his chair, one of his hands casually dropping to the monster cock in his lap, stroking it lazily. His eyes were glued to Becca's mouth.

She cleared her throat. "Well, *sir*... I guess I'm offering...um, myself? Anytime I'm at work and you... uh, need something... a release..."

He laughed, deep and throaty. "A release. So cute. I think you mean, anytime I need to paint your face, throat, pussy, ass, or any other body part with my cum?"

Becca's face reddened. She nodded. "You said this was a negotiation, though...so can I ask... not to, um, fuck my ass with that?" She motioned to his dick, which was back at full mast and leaking precum from the angry-looking head. The thought of that in her virgin asshole was enough to make her want to cry.

Bob tossed his head back in a full belly laugh, his face reddening. He laughed for almost a full minute, the power he was already exhibiting over this young woman beginning to fuel his lust.

"Becca," Bob said chuckling, after he had gotten his laughter under control.

"This is a negotiation, yes. However, in a negotiation, the person with power over the other has a lot of leeway in what they can demand." He began, enjoying the look of terror in her eyes as she thought of his behemoth splitting her like cordwood.

He let the tension build in her, noticing how tight her nipples were, how her eyes dilated in what he thought might just be a mixture of fear and excitement.

In fact, with her this close, he could smell her excitement, especially from the hand that held those decidedly damp panties.

"How about I offer a compromise?" He demanded in the form of a question.

"I won't claim your tight little asshole...right this moment. But I WILL have it. The when is up to you. You may choose to ask for it nor not. If you serve satisfactorily, that time will be pushed back. If not?" He paused, scooting his meaty weapon closer to her, her eyes crossing to keep it in view, the threat clear.

"However, I have a feeling you will ask for it sooner than you might think," Bob said.

"For example. If you ask me for it now, I will give you a 20% pay raise. For every day you delay, it drops by 2%." He followed up.

The smell of his precum hit her nose this close up. Heady, heavy, virile. She had to fight to keep from dodging back from it, or swooping towards it.

The veins were pulsing, the fucking thing looked like it belonged in an X-rated version of one of Alex's Hobbit movies. On the Dragon.

And he wanted to use that. On her. IN her. Oh, fuck.

She nearly fainted when Bob Anderson reached out, grabbed her by her hair, and pulled her toward his monstrous phallus.

"Tell me, Becca. Do you know who Nikita Kruschev was?" He asked, the fucking elephant trunk 3 inches from her face leaking so much precum she thought it would flood the office as she stared at it like it was the hypnotizing snake from that old cartoon.

"...what?" She asked distractedly as the monster moved up and down with each beat of this maniac's heart. She may have known, but she was so distracted she didn't really hear the question.

Her dry mouth...could she fit it? If she didn't, the house would never happen.

"I'll take that as a no," Bob said, gripping his Titanic shaft by the base, causing more of his precum to ooze out. She swore there was like a quart of the stuff.

And it kind of smelled good. Damn her, it smelled delicious, she thought guiltily.

"Nikita Kruschev was a Russian who had a unique method of negotiation in the U.N. I like to take a page from his book, with my own spin, of course" Bob spoke as if she had never answered.

Without warning, Bob swung his massive tool and it impacted Becca s cheek with a meaty THWACK!

A trail of precum led from her face to his swollen angry head.

Then from the other side, another THWACK! And another gooey string of precum.

"I WILL DESTROY YOU!" Bob yelled, before sitting calmly back in his seat, stroking his cock like some cartoon villain stroking a cat.

Becca was naked in the boss's office, scared and stunned, kneeling and offering up her body to save her job, and now she had been cock smacked and her face was dripping with this man's precum.

She bit her lip to keep the impending orgasm from taking hold. And to hold back tears. The man had done nothing other than smack her with his pussy destroying fuckrod, and for some reason, she thought she might cum.

She would not give in. She may be giving him her body, but she would not allow herself to enjoy any of it.

She knew, looking at the beast that had just marked her face, that that promise was doomed to fail. Probably before the end of the day.

"Now Becca," Bob said, using Becca's hair to hold her face still, "I want you to look me right in the eyes and open wide. It's time to see how skilled you are, and how much additional...On the Job Training you will require. So...Suck my cock, you worthless cock holster! Show me you're worth my time and money!"

Her mouth opened as the monstrous head tried to push past her lips. She opened wider, thinking of the house...and wondering about that 20% raise...

And realizing that Bob had lied...this wasn't a negotiation. This was a hostile takeover.

She had one brief moment to think of Alex before her world became filled with a cock that should have been on a bull instead of a man.

When she finally opened her mouth wide enough and let him in, Becca realized that she wasn't sucking this man's dick, she was being completely invaded by it. His cock was a fucking battering ram, and her mouth was a flimsy gate, easily breached. She tried to remain calm, to breathe through her nose, but he was so *big*, it was literally impossible to access any air, even from her desperately flaring nostrils. After just a few moments, she was pressing her hands to his firm thighs, trying to gain enough purchase to push away, to come up for fucking *oxygen*.

Bob smirked and shook his head, making a *tsk* sound. "Lots of 'On-the-Job' training, then, eh?" He said condescendingly. Despite the clumsiness of her blowjob technique, Bob was secretly pleased. She was sexier than he'd imagined under those cheap 'professional' clothes, and he knew once he could get her into some proper lingerie - a personal favorite La Perla set came to his mind - she'd be even more of a knockout. It didn't hurt that he enjoyed watching her struggle, enjoyed knowing that his was the biggest cock she'd ever seen, let alone touched.

"Stand up," he suddenly barked, yanking her off of his dick with a brutal tug of her long hair. She complied immediately, gasping for air, a thin strand of mixed saliva and pre-cum trailing from her lips to his cockhead, connecting them even as she stood. "I got a bit carried away there, your mouth looked so inviting, but it clearly needs more training before you're anywhere near ready to make me cum. Anyway, I need to inspect my new toy properly."

Becca bowed her head and said nothing. Her heart was hammering against her ribcage like a frightened bird. She was aware of her throbbing pulse in her neck, which was normal enough, but what alarmed her was that the same pulse echoed in her clit. Bob reached out and grasped her upper arm, spinning her around so that she faced away from him. "Bend over," he said gruffly. Without waiting for a response, he used his other hand to push her forward. Her ass was now at his eye level, and she could practically feel the searing heat of his gaze on her most intimate, sensitive parts. She was mortified at what he knew he would find there.