Risky Business

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loquere
loquere
224 Followers

"No, it's not you. You're fine...great actually. I can't say what it is."

Patrick stood, closed his laptop, and moved to sit beside Ashley. He sat there not saying a word until she began to stand.

"I'm sorry."

"Talk to me?" Patrick asked pleadingly.

"I can't."

"Talk to me. Trust me."

Ashley took a breath and sat back down.

"Talk to me...Ashley," he said again, struggling to connect by using her first name.

She leaned back and took a breath. "I...I..." she stammered.

"Trust me."

She took a deep breath this time. "During college, and after for a while... I had sex for money."

"You were an escort?" Patrick asked with an unchanged steady, emotionless face.

"Yes, but I haven't been one in three years." She stood as her eyes swelled with tears.

"Sit...it's okay." He handed her his handkerchief. "I'm assuming this has something to do with Jack the Jackass."

"Yes...he videotaped me. God, I can't believe I'm telling you this."

"You don't feel safe here anymore."

"Yes, that's why I need to quit," she said, standing again. Patrick stood as well, and Ashley fell into his arms. Feeling her soft mounds pressed against him, he fought his natural feelings and patted her on the back.

Letting her go, he said, "Can you work from home until next Monday?"

"Sure, but I can't work from home forever."

"Trust me; he'll be gone by Monday."

"You're okay with everything?"

"You've been okay with me for three years. Go home, and come back on Monday morning."

"Are you sure?"

"Yes," he said with certainty.

Ashley left Patrick's office with a smile, wanting to hug him but knowing he would feel uncomfortable. She ran into Jack at the elevator bank. "You really are just a stupid whore. It doesn't matter where you go. I know who you are now..." Jack ranted on until people neared him, giving Ashley the opportunity to exit.

She feared for Patrick a little, not knowing if he could outmatch Jack. On Friday, while watching CNN, she got her answer. There was a reason why Patrick was the boss.


This is CNN's Wolf Blitzer and you're in the Situation Room. Yesterday, a federal grand jury indicted investment executive Jack Elliot, who was then promptly arrested by the FBI. Mr. Elliot, who was facing multiple counts of securities fraud, amongst many other charges, has been quick to accept a plea deal that will see him spend the next twenty-two years in federal prison, instead of what could have been fifty years.

These charges are limited to his career at Rosewood Schmidt & Company in San Francisco prior to his start at Grant Hill Investments in Chicago. Grant Hill, of course, is a name synonymous with investing. Managing Partner of Grant Hill Chicago, Mike Paterson, said, and I quote, 'Grant Hill's investments are solid and remain secure. Mr. Elliot's move to Grant Hill was part of an orchestrated investigation, coordinated with the SEC and the FBI. Our clients' finances were never in any real danger.'

As more details arise, we'll keep you informed. CNN, the most trusted name in news.


Ashley smiled as relief swam over her. Later that night she received an e-mail from Patrick telling her what she already knew—he'd rescued her, and Grant Hill was trying to cover their ass. "Thank you," she emailed back.

"Come back to work. I need you," he fired back seconds later.

Ashley had unusual dreams that weekend. She kept dreaming about Patrick—nothing sexual—just him—running with him, playing chess with him. In the last dream, she took off his thick glasses and gave him a single kiss.

She was in the office extremely early on Monday, for once finally beating Eric and Patrick. She wore a tight dress that fully maximized her assets while still being conservative enough for the work environment, with just enough risk entwined in the vibrant colors. She had never worn the dress to work before; she didn't know why she did today.

"Good morning, Ashley," Patrick said, using her first name, which was unusual. Her eyes popped like he had offended her. "Sorry...was that inappropriate? I'm sorry, Ms. Limpkin," he said, rushing into his office.

Ashley walked into Patrick's office with his green tea. "No, that was fine. Thank you for everything. I can't imagine what you think of me..." She paused. "Well, I should leave you," she said, turning around.

"I lost my virginity to an escort," he dropped.

"What?" she asked in shock. She closed the door and sat down, listening eagerly.

"I don't know why I said that. I was just trying to say that we're in the same boat. I mean, I didn't know she was an escort...I should get to work."

"I trust you, and you can trust me." As she sat across from him, he confessed how his friends had gotten him drunk the night of his graduation and paid a beautiful escort to deflower him.

"This was—" Patrick began to say.

"Good...this was good. I've never really known you for the three years I've worked here."

On her way out of his office, Patrick said something that caused Ashley to turn. "My psychiatrist said to be more open with you." Ashley questioned him, but he turned all sweaty and nervous, so she left.

"Did he like me this whole time?" she thought. Ashley brushed it off, and over the course of the next month everything seemed to smooth out. That was until Ashley realized Patrick had arranged for her to be transferred to the Investment Management division as an Associate. She'd been waiting for the upgrade since she had started and had taken all the credentialing exams. Because Patrick already paid her exceptionally well, there was no change in pay. However, she would have her own assistant, independence, and the ability to make much, much more money later.

On her first day at the new job, Ashley accidentally exited on her old floor. She saw a guy working where she once sat but thought nothing of it. A few weeks later, she returned and discovered that the guy who had replaced her had been replaced by another guy. It was then that Ashley discovered that Patrick had requested only male assistants. She waited one night until his assistant had left; Ashley then barged into Patrick's office. Did I become the slut you couldn't stand being around...are you afraid of me...are you afraid of women now?"

Patrick began to sweat, stammering, "I...I don't think poorly of you."

"Why can't you work with me then?"

"Because..."

"Because what?"

"Because I finally worked up the nerve to at least come close to asking you out...and I couldn't put myself in the same position as Jack. Plus, you deserved the promotion. I—"

Ashley smiled inwardly. "Was this what you wanted, or was this your psychiatrist?"

"—Look, I'm sorry. I should have handled this differently. Everything was better the way it was. I don't know what I was thinking."

"I quit," Ashley declared with a sense of relief.

"Why?" Patrick asked, all wide eyed at the tall, beautiful woman.

"I'm doing what I should have done originally. I have enough money saved. I'll go back to school to get my MBA and earn my place."

"You don't need to quit for that. You can work part time. I can arrange it."

"No, I need to do this for me." She stood up, walked over to Patrick, and kissed him on the forehead. She walked out of his office and headed toward the elevator.

Patrick left his desk and walked after her. "I'm sorry if I treated you badly."

"God, Patrick you're the nicest guy I've ever known. You should never change. I'm not leaving because of you," she said, walking over to him and kissing him flat on the lips. Then she pulled away, leaving him heaving and breathing wildly. "I'm just curious. When were you planning on making that move?"

"What move?"

"Asking me out?"

"In the future," he said, sweating.

Ashley smiled as she entered the elevator, hoping that he'd actually do it on his own, knowing he'd have to change just a little for them to work out. She found herself genuinely wanting to be with him. She left Grant Hill for the very last time and walked out of the Ellis Oil lobby. Passing Eric in the sleek Benz, she waved at him for what she predicted was the last time. Turning back, she lamented about the one guy she had grown to trust with all her heart. She realized then that she had deeper feelings for him than she'd ever had for any other man. It didn't make sense to her. He was an extreme nerd, and he was average looking—but still, she kept seeing him in her dreams.

A year had now passed by. Ashley had taken another assistant position with a dramatic drop in pay, but with much less work, which allowed her to focus on her full-time studies at the University of Chicago's Booth School of Business. She was halfway finished. Without asking, Patrick had e-mailed her a glowing reference that had secured her entry into the highly regarded MBA program. He'd kept in touch with her, e-mailing her often throughout the year. She realized he was getting better; she didn't know how much until one day when she received one particular e-mail.

"This Saturday, would you like to go to dinner, as in a date with me?" She smiled and broke into laughter because of the shock, not because she was laughing at him.

Ashley didn't respond. For once she was in Patrick's shoes and didn't know what to do. She knew he was probably fretting in anticipation.

The next day, with intel from Eric, she stood next to the shining black Benz outside the Ellis Oil building at normal closing time. Exiting the building with a stream of workers, Patrick appeared in a classy designer suit. Ashley noticed he'd abandoned his suit schedule. She waved at him, but Patrick seemed to be the only man who didn't notice her. When he finally saw her, he was like a kid in a candy store. Smiling, he walked over to his driver and his love interest. Ashley was wearing a white dress that ended just below her knees and showcased her beautiful, ample bust and her long, beautiful legs. Mindful of the fact that she was an inch taller than Patrick, she wore flats.

Before she could ask Patrick where he was heading, even though she knew he had a psychiatrist appointment, he floored her with his compliment. "That's a beautiful dress, Ashley."

"What...thank you," she said, her eyebrows rising before lowering.

"It's true."

"That's why it was so sweet...thank you. Do you want to go to dinner now?"

"I have an appointment with my—"

"Your psychiatrist? I know, Patrick. I don't think he'll mind."

He smiled at Ashley as he held the door for her to get into the Mercedes. She had noticed the subtle differences in him as they drove to a restaurant. Sitting on the patio of a five-star restaurant, Patrick closed his eyes and pointed to a random dish on the menu. His method caused the waitress to smile.

"Lamb, that's different from the tuna sandwich you order every single day."

"I'm trying new things," he admitted.

"Do you want to have sex with me, Patrick?" Ashley said straight faced.

Patrick's eyes widened in surprise; spouting socially unacceptable phrases was his thing. "Yes."

She sipped her red wine. "How much would you pay me to do it?"

His sweating began. "I wouldn't do that. The time I told you about, I didn't know. You're not like that either—"

"Sorry, I was just testing you. We women do that sometimes. I'll try to be honest and direct with you because I know you'll be the same." He nodded, and they had their meal. When it was over Patrick started to pay, but Ashley wouldn't let him. "I invited you to dinner. I'll pay now, you'll pay on Saturday."

They left the restaurant and entered the Benz. Ashley gave Eric the directions to her home and then asked Patrick if he would like to join her for dessert in her apartment.

"Thanks, but I'm full," he replied, at which point she smiled and got out of the Benz.

"I'll see you on Saturday," she added. Five minutes after Ashley entered her apartment, someone knocked on her door. When she opened it, Patrick kissed her. She pulled him inside and they landed on the couch, with her on top. She began to disrobe.

Patrick tried to control his now erratic breathing, while saying. "You're the most beautiful...prettiest woman I've ever seen." Ashley smiled, rising above him enough to pull away his belt. "Stop!" Patrick said, shocking her. "We should go to your bedroom." Seconds later, Ashley was dashing to her bedroom, holding Patrick's hand behind hers.

Her white dress fell to the floor along with her bra, leaving only her black panties. Patrick, except for his jacket and belt, was still clothed. Ashley sat on the end of her bed and slowly eased down her panties as he struggled to unbutton his shirt. His hands went faster and faster and soon the shirt was off. She bit her lips in anticipation, knowing she'd already committed emotionally to Patrick for the long haul. His underwear came down next. At six inches, his cock wasn't the longest she'd seen.

Girth was another story as Patrick's cock hardened. It was at least the circumference of a soda can, or bigger. When it was fully hard, her fingers couldn't meet when she encircled it with her hand. His girth would scare most women, but Ashley knew the full pleasure of a thick cock and smiled at the rigid monster. She was excited about the journey ahead. With Patrick now lying on his back, she straddled his waist. Lowering her breasts to his chest, and then her mouth to his, they kissed for ten minutes. His tongue was stronger than expected, which made her wet with anticipation. Pulling her face back, Ashley looked into Patrick's brown eyes and said, "Your cock is beautiful."

"Thank you."

"Don't be afraid, Patrick. Touch me wherever you want," she said, upon seeing his hands planted to the bed. His hands slowly rose, spanning her back. He slightly squeezed her ass cheeks as their mouths rejoined. She removed his glasses, deciding she would buy him contacts later, and paused. Looking down as she straddled him, the whole picture didn't look bad at all.

"Can you...?" Ashley listened, waiting. "Can you put your breasts around my...penis?"

"Only if you don't phrase it to me as a question," she said, smiling and pushing her long blonde hair out of the way. "Tell me to do it. Patrick."

Patrick swallowed down some saliva. "Put your breasts around my penis—"

"Call it your cock, Patrick."

"Put your breasts around my cock!"

At his order, Ashley lowered her body. Her full breasts surrounded his girth, and again she told him how beautiful his cock was. With the first touch of her soft breasts, his cock began to spasm. "Oh crap, look out!" he cried, as jets of cum erupted upward and landed on her large, firm boobs. Ashley pressed on as she made his penis hard again between her mounds. Her tongue stretched forth, licking. Her mouth didn't dare tackle the gigantic girth. "I want to have sex with you now."

"Say 'I want to fuck,'" she corrected him.

"I want to have sex with you, make love to you...not fuck you!" he said, bringing a smile to Ashley's face as she straddled him. He shocked her when he suddenly flipped her over and got on top. He had her breathing faster and faster as his cockhead began to breach her tight pussy. Then he paused, nearly causing her to cry out. "Do I need a condom?" Patrick asked.

"I'm on birth control and—" Before she could finish, he pushed his cock head inside her slick pussy. "—Jesus Christ, yes!" she cried out. On only a handful of occasions in her life had she ever felt this full.

"Are you okay?"

"Move your hips. Fuck me...make love to me later, Patrick. Fuck me now. Please, please, fuck me now!" As Ashley spoke, Patrick moved his hips back and forth, causing her mouth to open. Her hands forced him down further and further. "Oh Christ...lord yes...right fucking there!" Wrapping her agile legs around his back, she screamed. He briefly silenced her by putting his lips over hers. His cock sped up, guided by her hands and legs. Her hands now spun into his hair to pull his head in for a rocking, passionate kiss. She couldn't control her senses; she wanted more. Ashley's toes curled and her neck arched backward. Patrick's chest started heaving and his breathing increased.

"I'm going to—"

"Cum in me. Yes, fuck me! Patrick...Pat...Yes...Oh!" she moaned. Her legs weakening around him. "Faster please...move your hips faster...faster!" she pleaded as he fucked her pussy raw until his eruption. Not done yet, she flipped them around, getting on top. Her hand balanced the amount of cock that entered her. "This couldn't be your first time!"

"It isn't. It's my second," he said. Ashley smiled before closing her eyes and lowering herself so that he sank deeper and deeper, stretching her snatch further and further.

"Oh fuck!" she exclaimed painfully, straining her vocal chords and emptying her lungs in one last blissful outcry. Soon, she was lying next to Patrick, panting. His lips trailed down her body and he lowered his face to her pussy. "You're just full of mysteries," she sighed.

"Can I kiss your pussy, please?" He didn't get it right at first, but she had learned that Patrick tried his hardest at everything he did until he did it perfectly, and this was no different. An hour later Ashley was screaming in release during her second orgasm of the night.

In the morning, she begged him to stay. She went downstairs with him and gave him a deep kiss before he got into the Benz with Eric, who had just arrived. "Don't change him too much. I still need a job," Eric quipped.

That day all she could think about was Patrick, and that afternoon she surprised him in the office with a random lunch and a pack of contact lenses. As Ashley passed the assistant's desk, she threatened the cute brunette with her eyes. She was tempted to recommend that Patrick go back to only hiring males. Shocked when she realized she was jealous, she soon came to grips with her feelings for Patrick. When she considered all the times she'd defended him, Ashley realized she had had deep feelings for him before that afternoon.

Sitting in Patrick's lap at his desk, she could see in his eyes how much he loved her, and she hoped he saw the same in hers. "You look hot with contacts. We should change your hair next."

"No...I like my hair!"

His uncharacteristic assertiveness was making Ashley wet. "Fuck me?" she begged.

With one swipe of his hand, Patrick sent his ThinkPad and the other items on the top of his desk crashing to the floor, making room for Ashley's long bombshell body. Soon enough, Patrick was between her legs and sucking on her tongue. His confident business personality had begun to take over. A new day had begun.

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3 Comments
AnonymousAnonymousalmost 11 years ago
Great story

I enjoyed reading it!

ironsoldier80ironsoldier80almost 11 years ago
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First "and" foremost, great story. I love reading about seemingly quiet and shy people getting ahead. That your main character Ashley realized she had developed strong and deep feeling for her boss long before she recognized them and that he looked after her and protected her without judgement was beautiful. Don't let judgemental pricks with tiny dicks, stick you with their annoying ticks. This an ametuer author site and you will find way too many of them. I am suprised he had the balls to comment under his account name instead of going anonymous. Even as a professional author you can't be perfect nor can you please everyone. I am sure he is just angry he favorite character from your story "Jack the Jackass" got his just reward. I encourage you to continue to take up your creative license and write to your hearts content. If you choose another site or choose to keep them to yourself so be it. Don't let negativity hinder your mind from soaring.

LadyVerLadyVeralmost 11 years ago
Great story

I gave you a 5. I hope you continue the story.

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