Playing the Bosses

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Keep Them On

It was yet another day of another week at PMC Group and Eva was just finishing up her lunch when she received a notification that it was time for her 2:00PM with Justin to prepare for an upcoming conference call they’d have with more Japanese executives in a few days.

Sitting in meetings with Justin became a regular routine for Eva and she started spending just as much time with him as she spent with Adrian, if not more. He was looking to expand PMC Group’s reach to an Asian market starting with Japan because it was where he had the most connections through his family.

Also, with each meeting, Eva was completing two tasks in one. Her very thorough notes were impressive to Justin, gaining more of his confidence in her, and she was also able to feed the information she gathered to Alexis.

“Hi Eva,” Justin greeted when she entered his office. “How are you doing this morning?”

With the two of them spending more time together, Justin grew more comfortable with Eva and they found themselves conversing more casually. For Justin, Eva was easy to talk to and their chats had gradually turned more candid the more they spoke.

As she approached to take her seat, Justin scanned over Eva as he often did since spending more time with her. He admired her sense of style and the way she managed to dress professionally, yet still with an alluring undertone that he wasn’t quite sure was due to the outfits or the woman wearing them. Also, Justin didn’t understand why, but he often found his eyes drifting down Eva’s legs and lingering on her heels; it seemed like she had a different pair every day.

“I’m great,” she replied with a small smile as she sat across from him. “And you?”

“I’m fine, just hate this time difference we have with Tokyo. I’m glad they were willing to speak even though it’s evening their ti—”

Justin was cut off by his phone ringing with a distinct tone and he immediately rolled his eyes before picking it up.

“Hey, babe,” he answered dryly. “I’m in a meeting. Can we talk later?”

Eva figured it was Ashley, though she couldn’t hear what she may have been saying on the other side of the phone. All she knew was that Justin looked agitated to even be speaking to her.

“Okay, okay,” Justin said quickly, trying to rush Ashley off the phone, but she kept going until his tone turned sharp. “I told you I was in a meeting. I’ll call you back later.”

A few more seconds went by and after he finally hung up, Eva gave him a curious look.

“What?” he questioned. “Why are you looking at me like that?”

Eva had no qualms with asking such a personal question, but she knew she’d have to feign timidness in her approach. “Well, Mr. Matsuda... And I don’t mean to pry or be inappropriate...”

“Go on,” Justin urged.

“Ashley is your girlfriend, right? I think you told me before that you two have been together for a few years... But it just doesn’t seem like you like her that much.”

Justin’s eyes went wide before he cleared his throat and straightened himself up. “What makes you say that?”

“It’s just that whenever I see you interact with her, you seem annoyed and you never get excited about her calling or coming into the office. You just treat her like another chore or work task for the day.”

“Interesting observation,” he said coldly.

“Like I said, I didn’t mean to pry—”

“No, it’s okay,” Justin assured. “With Ashely and I, it’s just that... It’s that we...” He huffed to move past his hesitation. “Eva, we’re speaking plainly right now, right? I mean, you asked me a question and I want to answer you thoroughly, right?”

“Oh, um... okay?”

“Ashley and I... She’s a nice woman and I like her and all. We make sense as a couple, I mean, we have similarities in what we like to read and watch and we both fit in the same tax bracket and come from wealthy families. But there’s just not much of a spark like there was before when we first started dating. I’m not sure if we’re just used to each other now or if it’s something else.”

“I see...” Eva nodded thoughtfully. “You could always reignite the spark, though. Do something new, something fun... Maybe take a three-day weekend or full-on vacation and go somewhere exotic. It’s possible all you need is a change of scenery.”

“We’ve tried that...” Justin twisted his mouth while staring at Eva with tensed brows. “I think it’s the sex,” he blurted and Eva’s eyes went wide at his openness. “Sorry, Eva... I’m not trying to make things weird, I’ve never told anyone... and it just slipped out.”

Eva was somewhat surprised at Justin’s revelation, but mostly annoyed that he would bring up being unsatisfied with their sex life, feeling embarrassed on Ashley’s behalf.

“My advice still mostly stands,” Eva said flatly. “Just change things up in the bedroom. I’m not sure what the dynamic between you two might be, but in any relationship, you should be able to be open with your partner about your desires. So, if you’re feeling unsatisfied, you should talk to her about it and be straightforward with her about what you’re interested in trying or how you think you could improve the sex.”

Justin considered Eva’s words before he released a low chuckle and scratched the back of his head. “Sorry, I guess I did a bit of oversharing, but I do appreciate the advice.”

“Of course,” Eva replied with a smile. “Like I’ve told you before, I’m here to earn your trust and as your assistant, I want to make sure I’m as helpful as possible, even when it comes to things in your personal life like this.”

“Thanks, Eva.”

After her exchange with Justin, Eva started thinking back to her relationship with Eric and the way the two of them ‘made sense’ just as Justin had explained about himself and Ashley. She and Eric were both business savvy and came from affluent families. He was also nice enough and showered her with gifts, but something still didn’t mesh with their relationship.

Eva couldn’t bring herself to develop feelings for Eric, no matter how hard she tried, and she wondered if perhaps Justin was in the same predicament.


With the start of the new week, Caleb had been planning to work his charm on Eva and after his very long morning of meetings, he walked into the office around early afternoon ready to put his plan into action. He’d never been denied by a woman before and Caleb knew that once he started flirting with Eva, she’d be on her knees in his office before the end of the week — if not that same day.

He strolled toward Eva with a closed-mouth smile and a twinkle in his eyes.

“Good afternoon, Eva,” he said when he reached her desk with a large drink in his hand. “I bought you a caramel frappuccino with whipped cream and extra caramel.”

Eva hadn’t looked up at him and appeared to be focused on something on her computer screen.

“Afternoon, Mr. Peterson,” she greeted dryly without removing her eyes from the screen. “I’ve emailed you your mid-day update.” That was one of Eva’s standard lines for him the rare times that they would interact and it was obvious to Caleb that she didn’t listen to a word he said.

Hiding his agitation, Caleb sat the drink on her desk and Eva finally looked up at him curiously.

“I bought you a drink, Eva.”

She raised a confused brow because she was pretty sure it was his first time calling her by her name in the several months she’d been working there.

“A drink,” he repeated. “It’s a caramel frappuccino with whipped cream and extra caramel. I’m not sure what you normally get, so I had to guess.”

Eva picked up the drink and looked over it with an aloof expression. “Thanks, Mr. Peterson,” she said, her tone still detached.

“Call me Caleb,” he said with a wink and Eva had to hold herself back from rolling her eyes.

While Eva knew he was still in earshot, she said, “I need to throw this cheap nasty shit away,” before getting up from her seat with the frappuccino and searching for a trashcan away from her desk.

Caleb didn’t visibly react, but something about the way she pretended to accept his offering before insulting it and throwing it away bothered him to the point that he felt it in the pit of his stomach. It was as if she was trying to spare his feelings like he was some sensitive child while underneath her fake smile, she was annoyed by him.

Eva made Caleb feel average. Even worse — she made him feel inadequate.

And he hated that.

As Eva searched for a trashcan, she thought about this next phase of playing her games with Caleb. It appeared that he’d given up on outwardly being an asshole was attempting to charm her, which was exactly what she expected him to do.

Now, she just had to continue showing him indifference or very subtly reject his advances in a way that made it seem like she was treating him delicately, just as she’d just done with the drink. Eva actually liked frappuccinos, but she was very picky about where they came from and there were only two spots in the city that made them just the way she preferred.

The assholes are always the easiest, she thought to herself with a sneer.


Justin backed Ashley into his bedroom as their mouths eagerly moved against each other and they only broke away to remove their clothes. By the time they fell over on his bed, she was in nothing but her panties and heels and he was in his boxers.

Kissing and sucking at Ashley’s neck while he was on top of her, Justin pulled one of her legs up and caressed the side of her thigh.

“Justin,” she breathed. “Let me take my shoes off.”

“No,” he rasped against her ear. “Keep them on.”

Ashley found it an odd but harmless request, so she kept her heels on as he’d asked.

Justin turned them over so that she was on top. With the way his hands glided down her back and griped at her ass and her thighs in a more intense way than usual, it felt like he was grabbing for more than was there.

When Ashley sat up, still straddling him to tug at his boxers, she realized that his erection had grown faster than usual and she assumed it had something to do with his request for her to keep her heels on and the way he’d been groping her more heavily.

Once she freed his length, Justin put his hands gently at her sides rather than holding them and taking the lead as he normally did.

“Why don’t you take control tonight, babe?” He took one of her hands and guided it up his body until it was at his neck and Ashley looked down at him confused.

“You want me to choke you?”

Justin nodded with a slight smirk on his face. “I want to try with you being more dominant.”

“Oh um... Okay?” She slid her panties to the side before lowering herself on his dick and rocking her hips.

Her hand was wrapped very lightly around his neck while she rode him slowly and she could tell that he wasn’t as into as he seemed when he first asked her to choke him.

“Tighter,” he said and Ashley only very lightly tightened her grip around his neck.

Justin put his hands on her hips to guide Ashley’s movements so that she would ride him faster, but he was still unsatisfied with the lack of control she was taking and he could feel himself softening inside of her.

Finally, he gave up on the power exchange and turned Ashley over so that he was on top and started pounding her the way she liked to be fucked with his hand around her neck and leg on his shoulder.

She bellowed his name and was obviously enjoying the experience, but Justin was mostly out of it, keeping himself just hard enough to fuck her until she hit her orgasm.

After Ashley came and Justin went soft without coming — as had been happening for the past several weeks — the two lay in bed, looking at the ceiling.

“I like it better when you’re control,” Ashley admitted. “I prefer when the man is dominant.”

“I know,” Justin replied before closing his eyes to go to sleep.


A/N: Thank you for reading!

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