tagErotic CouplingsRisky Business

Risky Business


At the center of the Chicago Loop stood Ellis Oil Tower. It was 10 p.m. and a single light remained lit on the thirty-fourth floor—one of nineteen floors owned by Grant Hill Investments. Patrick Davis, wearing his round rimmed glasses, sat in his plush leather chair vigilantly monitoring stock tickers scrolling across the screen of his trusty, yet aged, IBM ThinkPad.

Patrick was the only one in the office without a MacBook. At forty, he was set in his ways. Not a soul attempted to change him because beyond his mannerisms flowed a river of gold. Patrick's success could never be confused with anything other than raw talent. Grant Hill's early major investments in eBay and Google had secured Patrick's large glass desk and the sprawling office that had become the envy of every employee.

He had never been in a romantic relationship and had only kissed a girl when he was in his twenties. He also had sex that night; he just didn't remember it too well. It all started with the necessary roommate he didn't want and a celebratory dinner he had refused to attend. Patrick was twenty-four and had just graduated from Wharton with an MBA. Harrison, the unwanted roommate, dragged him to a bar after the dinner to celebrate. He coaxed Patrick into drinking more and more, causing Patrick's inhibitions to crack and the games to begin.

The next morning Patrick woke up in a hotel room with his head banging and an over-filled condom sticking to his abdomen. He remembered enough from the night before to know he'd fucked the attractive, curly-haired brunette whose sleeping body still clung to his. Maneuvering away from the naked brunette, he kissed her lips, grabbed his clothes, dressed, and dashed from the hotel room.

A week later, Goldman-Sachs New York hired Patrick. However, even though he was a solid investor, his extremely introverted personality made him a laughing stock among the alphas who dominated the elite firm. This was everything he had assured himself the real world wouldn't be like. After a year at Goldman-Sachs, an executive at Grant Hill's Chicago branch, Mike Paterson, stole Patrick away.

Mike understood Patrick and decided to employ his unusual but lucrative skills while also mentoring him. When Mike was promoted so was Patrick. Mike built an environment that catered to and grew with Patrick.

After fifteen years at Grant Hill, Patrick's office was as large as Mike's but isolated by a gatekeeper assistant. Limiting his interactions with people, the assistant in the outer office was his only contact to the hundreds that answered to him. Patrick was now one of two Executive Partners and one of the three top bosses at the Chicago office—the second Executive Partner managed the office while Patrick managed the investment side. Mike Paterson, now the Managing Partner, was Patrick's only immediate boss. Patrick's success in growing billions in profits for the Chicago office frequently left the New York head office's profits in the dust, resulting in their frequent recruiting efforts of him.

Everyone else had gone home five hours ago. Patrick sat at his desk watching numbers and writing down solutions on a notepad before shredding them and retaining all the data photographically. Below his desk, the shredder was buzzing at maximum speed to dispose of the notes.

A knock on his office door soon distracted him. "Mr. Davis...sorry for interrupting, but I need to go now. I am sorry, sir. I would stay longer, but I have a family emergency," said Ashley Limpkin, his executive assistant.

Patrick didn't say a word. He simply nodded, ignoring the gorgeous, southern California, blue-eyed blonde. At five-eleven, she was an inch taller than he was. Today, her sizable, natural bust was hidden underneath the blazer she had purchased on impulse. Not that she was afraid her boss was looking at her striking, statuesque body.

When Patrick hired her three years ago despite her limited experience, she had assumed she'd have to tackle the usual sexual advances that would be made towards her. When none came, she had briefly assumed he was gay because shy men weren't known for advancing in management. Over time, however, Ashley learned that Patrick's confidence spilled out in his work, especially during meetings, when discussing data and trends; he was outspoken and clear when discussing business and work—a complete contrast to how he was anywhere else.

She had dropped the gay theory after a month, realizing Patrick was an extreme introvert who felt safest and happiest in his work. She felt sorry for him, and she did her best to assist him by adapting to his work style. He never asked her to stay late, but she worked late anyways. Tonight was the exception; she needed a break. "Do you need anything before I leave, sir?"

He indicated no by shaking his head.

"Night, Mr. Davis," she said, turning, her long blonde hair rippling.

"Goodnight, Ms. Limpkin," he said, finally raising his head, his eighties hairstyle sitting atop a cute enough face. "Good morning" and "good night" were the two things she was sure he would say—and some days were the only things Patrick would say to her, as he preferred to communicate with people via email instead of in person, even if they were just a few steps away.

Ashley walked to the elevator bank. As the elevator doors opened, she remembered something and was about to turn her designer heels around and head back to the office, but then decided against it. Instead, she pulled out her Blackberry and sent an e-mail to Patrick to remind him that the new second Executive Partner would be starting the next day.

A second later Patrick received Ashley's e-mail alert. Both Mike Paterson and Patrick were responsible for hiring Jack Elliot—the new Executive Partner—who seemed extremely outgoing and full of himself, the type of guy that could, and would, get any woman. In the end Mike was won over by Jack, despite Patrick's objections to the discrepancies in Jack's financial history.

After exiting the lobby Ashley strolled over to the polished black Mercedes S-class parked outside the Ellis Oil building and knocked on the window. Seeing Ashley, the driver brought down the passenger window. "Eric, he's going to be up there late again. I apologize for him," Ashley said to the older man.

"That's why I get paid the big bucks, Ashley. I'm fine. Do you need a ride anywhere? I could drop you off and be back for Mr. Davis, I'm sure."

"No, if he comes out and sees that you're gone, he'll freak out."

"If it's for you, I'm sure he'll be fine with it...this once."

Ashley didn't understand but she got in the back of the Benz anyway. "Alistair's Bar," she directed. "Are you saying he likes me? It sure doesn't seem like it. What does he say?"

"No, he doesn't talk about you at all."

"I don't get it."

"You're the first assistant in the ten years I've been driving him that he doesn't complain about. In the first two weeks, yes, he thought you did everything wrong, but it seems like you adapted quickly. At first, I thought he would fire you like the twenty others."

"Well, I guess that's good. When you think about it, I'm lucky. All the other assistants knock on him, but their bosses are constantly propositioning them. It's a cesspool up there. He's actually a good boss."

"Mr. Davis is what I call asexual. In the years I've known him, all I've ever seen him do is work and nothing else—no girls, no boys, nothing."

"Jesus...that's sad."

"Well..." Eric said.


"For a while I thought he was seeing someone. He leaves work the normal time, once every other week. He sends me home and walks. I later found out he started seeing a psychiatrist a few years back." Eric pulled up in front of Alistair's and left the motor running.

"I thought he was attending meetings when he did that... That's good," Ashley said, before sliding out of the leather cabin of the Benz and thanking Eric for the ride.

Ashley sat with her fellow assistants and ordered a White Russian. The others already had a head start on her and were borderline tipsy. "I'm surprised The Ogre didn't keep you late again. He's usually such an asshole," one assistant added, as more chimed in. Ashley mysteriously found herself defending Patrick. He had taken a leap of faith when he hired her; she had been twenty-four with a bachelor's degree but zero business experience. Her beauty had gotten her so far but didn't seem to be helping in her quest to manage multi-million and -billion dollar investment portfolios. Her feelings for him were mixed, but right now she was going to the mattresses for her boss.

After Ashley's onslaught of words, the others changed the subject to Jack Elliot, the hot new Executive Partner. The name rung in Ashley's head...it seemed familiar. She only knew tidbits about the new EP though; he'd received his MBA at Berkley, which meant he was from California like her, but this was the first time she'd heard his full name. She soon forgot about it and partied with the girls. Since the next day was a weekday, she didn't hit the juice too hard.

The next morning, Ashley arrived early at work with Patrick's green tea and her black coffee. She knocked on Patrick's door; hearing his response, she entered his office. It was Thursday so he had on the red tie, pink shirt, and charcoal suit that his consultant had picked for that day. Even with the special occasion of his new equal's first day, Patrick kept to his schedule.

As Ashley handed Patrick his green tea, someone knocked on his office door. "Patrick? Jack Elliot. Can I come in, bud?"

"Sure," Patrick said, secretly wanting to say no.

As Jack entered the spacious office, his eyes lingered on Ashley's skirt-covered long legs. Jack was tall with black hair and a defined jaw. His eyes devoured Ashley's form with a predatory stance, and then out of nowhere a smile formed. Ashley was pleased with what she saw too, but his smile started to shake her, especially as it began to look familiar.

"Bridgett, is it?" Jack asked, sending a cold shiver through Ashley's body.

"No, her name is Ashley," Patrick corrected, his eyes alternating between the numbers flashing on his ThinkPad and the numbers on the wall-mounted LCD TV's.

"Well, Ashley, it's nice to meet you. Why don't you hop out and allow the men to discuss business?" He watched her ass as she walked out. Her conservative skirt did nothing to hide her raw beauty. "You fuck her yet?" Jack asked, sitting on Patrick's glass desk.

Patrick failed to conceal his displeasure in Jack. "Did you come here for something, Mr. Elliot?"

"Did I hit a nerve, man? Mr. Elliot...what, am I my father?" When Patrick didn't respond, Jack quickly got down to business.

Meanwhile, Ashley was at her desk panicking because she realized Jack knew her dark secret. She had no clue what was happening in Patrick's office and was afraid. Jack walked out of Patrick's office and shot her a smile as he passed through the outer office. Stopping at her desk, he said, "I loved the way you used to suck my cock, Bridgett. It's been too long. How much do you charge now?"

Ashley sat frozen and perplexed. Jack smiled at her discomfort. No one was in earshot as she said, "What you're saying is inappropriate. You have me confused with someone else, Mr. Elliot."

"Do you have a twin named Bridgett? I never forget a face I've fucked, trust me," he said with an evil grin before adding a savage whisper, "...whores don't get to live happily ever after. This isn't fucking Disney!"

Jack headed to his office to plot Ashley's submission. The days passed with the office settling into a routine that included his administrating and demonstrating his control as the women in the office fell for him. Ashley wanted to forget her years as an escort; however, it now appeared that she wouldn't be allowed to forget how she paid for college and survived prior to moving to Chicago.

The following Wednesday, Jack walked into Patrick's office. He simply smiled at Ashley as he walked by, torturing her again. He spoke to her on his way out. "Bridgett, it's lunch time. Come with me." They arrived in Jack's office after passing Hannah, his cute, petite executive assistant. Jack closed the door. He and Ashley were now alone in his office. "Can you believe your nerd boss's office is triple the size of mine and that he gets nine million a year, twice what I get? Fucking you should come close to making things even, for now."

"Can you just forget this, please, Jack?"

"So now you remember?"

"I'm not that person anymore, and even then I only did it part-time for a select few."

"I'm not forgetting anything. I paid two grand an hour to fuck you in the past. How much now?"

"I haven't done that in three years. It's not who I am."

"You will, or you won't have your job for long."

"Excuse me?"

"No, I won't, but you can suck my cock."

"No ...I'm going to HR right now."

"Are you going to tell them how you were a Beverly Hills whore?"

Ashley paused.

"Exactly! Get on your fucking knees," he said, grabbing a remote and closing the blinds to the windows in his office.

"It's your word against mine. I haven't been an escort in the three years since moving here, and I won't do it again. Again, it's not who I am anymore!" Jack walked into the center of his extravagantly decorated office and pushed a button on the same remote. Instead of market data showing on his LCD TV, a clear-as-day video of Jack fucking Ashley doggy style appeared.

"You fucker...when did you video-tape me?"

"Such is the risk of an outcall," he said, making her sick to her stomach, to the point where she became queasy and spewed up all over his green leather couch. His smile quickly faded. As he turned off the DVD, Ashley ran out of his office.

"Are you alright?" Hannah asked, questioning Ashley as she ran past her.

That evening and the rest of the week, Ashley searched for a new, comparable job. The salaries for the few listings she found were on average eighty thousand less than what Patrick paid her. It seemed she was far luckier than she had thought; it just took a dark period for her to realize it.

Another week went by. It was Thursday and Patrick was leaving at five o'clock like everybody else. He had a psychiatrist appointment, which he attempted to keep secret. Just as he left, Jack swooped in. "I didn't know I was such a disgusting person, Bridgett." Ashley didn't respond. "Do you have a key to his office?"


"Don't ask fucking questions." Jack extended his hand, and she reluctantly placed her key to Patrick's office in his palm.

As he unlocked the office door, Ashley pleaded to his soulless humanity. "Jack, please don't do this."

"I'm not forcing you. You can leave this job, or suck my cock. New deal...I'm not asking to fuck you. I just want a simple blow job. Most of the assistants here do it already. You know that. Do it, and you get the tape...I swear to god!" he said, guiding her into Patrick's office.

"That was a long time ago," Ashley said, tears rolling down her face. She now stood in the middle of Patrick's large office facing Jack.

"My cock better be in your mouth in ten seconds, or the entire company is getting an anonymous e-mail with a video of you being fucked—with my face blocked out of course. Do it now. This is your last warning." As Jack lowered the blinds with a remote, Ashley used a wristband to tie up her long, blonde hair before dropping to her knees on Patrick's carpeted floor. She unbuckled Jack's belt and soon had his semi-hard penis out of his pants, licking the tip, her tongue now reluctantly spanning his length.

"Put it in your fucking mouth," he demanded. Ashley reluctantly covered his long cock with her plump lips and moved her head up and down his shaft. His enormous hands soon gripped and pushed her head, forcing her down deeper. Without a care for her, Jack kept working more and more of his cock into her hot mouth. "There's a good whore. Ohh...ummh," he said, fucking her face as tears swam down from her eyes. His hands soon moved to squeeze her breast. "Oh shit!" he let out, as his legs weakened. He pulled his cock out with a pop with enough time to cum all over her face. "Take off the dress and get on the floor."

Ashley looked up at him with her blue eyes and said, "I thought it was just the blow job?"

"You really are a stupid bitch...but fuck, you're hot. That's why I kept coming back. No, this is never, ever going to stop. Get on the floor," he said, shoving her. Her dress was partially off, showing her flat stomach and ample, bra-clad bust. Jack lurched down, getting on top of her. She tried to look away, but he forced her face up toward his so she closed her eyes. "Tell me if you want me to stop, Bridgett. I'm not forcing you. Just keep in mind everyone will know that name forever."

Quickly, Ashley's dress was off and he was on top of her, his cock at her front door. "Put a condom on," she dictated with venom.

Hoping to finally fuck her without one, Jack said, "No, you don't get to—"

"Wear a fucking condom, or I'm yelling rape."

"—alright, fuck," he said, getting up and grabbing his wallet before plopping right back down on top of her. Ashley closed her eyes while his cock breached her smoothly shaved slit. "Sweet, sweet home," he mused. She played a song in her head as he pushed in and out while removing her bra, mauling at her large, full breasts. "Tell me how much you like me fucking you, Bridgett."

"I hate you!" she declared, just as he exploded into the condom.

He grabbed her smooth jaw with his hand. "You're making this more difficult than it needs to be," he said, standing up. Ashley stood as well. While she dressed, Jack watched her as if he was marking territory.

"With the millions you get, can't you get yourself someone who can tolerate you?" she asked coldly.

"I will when I'm old and boring. I think I'll fuck you in the ass next time for that crack. I'm going to make you break all your rules."

For the first time in three years Ashley called in sick. She moved out of her apartment into a new one unknown to Grant Hill. She came into the office on a Tuesday after a week of calling in sick, thinking Patrick had probably gotten a temp by now. As she walked in that morning, no one was around her desk, and then she remembered how her boss was. He'd do everything himself before working with a stranger.

As if he were the devil himself, Jack appeared as Ashley neared Patrick's office. "Bridgett, are you trying to avoid me? I even stopped by your apartment. Did you move?" Ashley ignored him as she walked toward Patrick's office with a letter in hand. "Don't do that. No one ignores me."

"I do," Ashley said with fire in her eyes.

"Do you want to continue working here as the only six-figure secretary?" he said degradingly.

"No, I don't, actually...I'm quitting," she said, leaving Jack in stunned shock.

He grabbed her arm before she walked into Patrick's office. "You make as much as an MBA graduate starting here. No one...no one like you gives that up."

"Let me go—now!" she screamed, causing Jack to leap away as she walked into Patrick's office and slammed the door behind her.

"Ms. Limpkin. Good morning...feeling better?"

"I need to talk to you."

Patrick's eyes left his laptop and he looked up, giving Ashley his undivided attention. She had the letter, but instead of giving it to him right away, she grasped her Blackberry and sat down in a chair on the other side of his glass desk. Patrick looked on, waiting patiently. He took off his round rimmed glasses and scratched his head after reading her resignation email. He responded with an offer of more money. Ashley froze when she saw the new salary that he offered in an email, $300,000 a year.

Speaking now she said, "Money is not the issue."

"Is it me?"

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