Playing the Bosses

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A/N: So, this chapter ended up being longer than expected... BUT, it’s worth it for the chapter that comes after 🙃.


“Fuck! I can’t believe I did that,” Adrian chided himself when he entered his apartment. “I hope I didn’t fuck up too bad... I mean, Eva did kiss me back. Hell, she was in total control when we were kissing... Then again, I’m the one who initiated it... But she called me ‘darling’ and then got all... authoritative."

He ran his fingers through his hair and pulled off his shirt as he went into the bathroom and turned on the shower, figuring a cold one would be best. While he would at times fantasize about Eva, Adrian never went as far as masturbating to his fantasies, though he had come close. He was afraid that he’d throw himself into more dangerous territory and have an even harder time resisting Eva.

“Whatever, I’ve kissed her at this point,” he said before turning off the shower and deciding to relieve himself beforehand.

Adrian sat at the edge of his bed and pulled out a small bottle of lubricant from his nightstand before putting it on his hand and holding his length with it. He closed his eyes and started slowly stroking himself.

“Such a good boy,” Eva cooed as she approached Adrian. “Always so well-behaved...” Once she was close enough, she took his chin between her fingers and lifted his head to meet her gaze.

“Why have you stopped?” she questioned when her eyes drifted down to his member in his hand. “Keep going for me, darling.”

“Yes, Ms. Eva,” Adrian breathed before he returned to pumping his hand.

Eva traced her thumb across his lips, just as she had when they kissed in his office. “You know that I’ve already got a read on you, right darling?”

“What read, Ms. Eva?”

“You like to serve. Don’t you?”

Adrian nodded and sped up the pace of his hand. “I want to serve you, Ms. Eva,” he confessed.

“I know that you do,” she replied softly.

His eyes finally parted from Eva’s to look at what she was wearing and he groaned at the sight. She wore an all red set with a caged bra, matching panties, and platform heels.

Adrian licked his lips at the sight and he felt Eva’s hand push against his chest for him to lay down. Once he was on his back, still stroking himself, Eva crawled on top of him on all fours with her face hovering just above his. He didn’t realize it, but his hand slowed to almost a stop as he anticipated Eva’s lips meeting his once again.

“Did I tell you to stop?”

“No, Ms. Eva.”

When Adrian started stroking himself again, Eva met his lips and just as she’d done when they kissed before, the woman was in complete control. He nearly came when she wrapped her hand around his neck and he winced when she broke away.

“You always kiss me so eagerly, darling... Is it because you want to put your lips somewhere else?”

“Please, Ms. Eva...” Adrian gulped. “May I?”

A smirk etched into her face and Eva crawled further up his body until her knees were on each side of his head.

“Stick your tongue out,” she directed and Adrian did as he was told.

“Good boy,” she purred as she started grinding against his tongue, still with her panties on. The vibrations caused by his moans against her caused Eva to release some of her own.

“You want more than this, don’t you, darling?”

Adrian’s response was muffled against her core and he nodded while his eyes locked with hers.

“Your desperation really turns me on...” Eva pulled her panties to the side so that Adrian’s mouth could make direct contact with her lower lips.

The moment he tasted her, Adrian couldn’t help but start eagerly moving his mouth on his own.

“Did I say... you could... do that?” Eva said through light moans, but Adrian was already too far gone, focusing on eating her out.

Those were the last coherent set of words he heard from her before bringing Eva to her climax, her sounds and trembling body pushing Adrian to his own.

“Fuuuckkkk,” he groaned as he came all over his hand and abdomen. Once he finished, he regretted his decision to masturbate to a fantasy of Eva because now his desire for her only became more intense.


“So, what do you think, babe?” Justin asked Ashley when she put on the very tall black pumps that he bought her. He was sitting on the couch as she stood in front of him wearing the heels along with an all black leather lingerie set he also purchased for her.

“They’re really cute and comfortable,” she beamed. “How’d you manage to pick these out?”

“I just did some research and found a few sites that people online recommended as having comfortable shoes.”

“Well, you did a great job. So...” Ashley joined Justin on the couch and straddled him. “Now that we’ve talked about it in more detail, I’ll try this control thing.”

“Oh really?” Justin questioned with a smirk, looking up at her and holding her hips.

“Yes, I’ll at least try it. I’ve never been interested in dominating, but I figure I can give it a shot since you want it so much.”

“I appreciate the effort, babe.” Justin readjusted, sinking further into the seat so that his dick aligned with Ashley’s core.

Ashley wrapped her hand around his neck, holding it tighter than last time and started to move her hips to grind against him while Justin caressed her thighs.

She leaned in to kiss him and Justin remained mostly still to allow her to take the lead, though she had a hard time doing so. However, in an unexpected move, she pulled his bottom lip between her teeth and Justin felt his dick twitch when she did it.

“Did you like that, honey?”

“I did,” Justin whispered.

Ashley continued to grind against him as she began placing kisses on his neck. Justin’s hands move up her thighs and he started grabbing her ass aggressively as he’d been doing for the past few months. Ashley liked when Justin was more dominant, but something about the way he seemed to try groping her more heavily when they were intimate bothered her. It was as if he didn’t realize he was touching her, like he was thinking about someone else.

Between that and not being totally comfortable with dominating, Ashley stopped him and pulled his hands off of her.

“Why do you keep doing that?” she asked, not hiding the agitation in her tone.

“What do you mean?”

“Lately, you’ve been grabbing at me in such a weird way, like it feels like you’re handling my body as if it were larger or something. You open your hands up wider and when you grip my ass or thighs, it feels more aggressive.”

“I don’t understand. You like it when I’m rough with you.”

“But what you’re doing isn’t exactly rough, it’s just different and it makes me uncomfortable.”

Justin let out a deep sigh. “I’m not trying to make you feel uncomfortable, babe. Sorry about that.”

Ashley rolled her eyes, got off of him, and started walking toward the bedroom.

“What is it now?”

“Everything you say to me feels rehearsed, Justin. It’s like you only say what you’re supposed to say, but not what you actually want to say. None of it feels genuine.”

“But babe...”

“But nothing,” Ashley snapped. “I don’t know what is going on with you, but I need a break until you figure out what the hell it is.”

“Ashely, please...” He pleaded unconvincingly.

It wasn’t lost on her that Justin was still in the exact same position on the couch and didn’t even make an effort to follow her when she left him.

“You’re so full of it,” she sighed. “Let’s just take a week or so to think about it.”


Caleb was in the bathroom showering while Casey and Fiona — the women he’d told to come over that night — sat in his bed talking about the evening they just had.

“Is it bad that I’m shocked he made both of us come this time?” Casey asked Fiona.

“Not at all,” she replied. “I’m surprised too. Usually it ends up you and I having to get each other off, but Caleb actually seemed somewhat interested in our pleasure this time. Who knew a jerk like that could eat pussy?”

“Right,” Casey giggled. “That had to be the most surprising part. Either way, fucking men with power like him comes with other perks. And at least he’s hot, which is super rare.”

“I know, right? He could be a model himself—”

“The fuck are you two still doing here?” Caleb interrupted when he walked out of the bathroom and found Casey and Fiona still in his bed. “Both of you have been here plenty of times to know the rules.”

The green-eyed blonde and freckled brunette exchanged a look before getting out of bed and quickly putting their clothes back on.

“And there it is,” Fiona whispered sharply. “Asshole.”

“Yeah,” Caleb scoffed. “And you were just licking mine not even an hour ago while Casey had my cock in her mouth.”

“Whatever,” she said under her breath.

“Anyway... I already spoke to Madeline and you’ll be able to model her pieces for Paris fashion week.”

“Thanks,” Casey replied dryly before she and Fiona finished getting dressed and walked out the door.

Caleb was still annoyed even after the women left. He realized that for the past several months, he’d been more frustrated than usual and his ongoing failure at gaining more attention from Eva only made it worse.

“Those girls don’t know their fucking place,” Caleb grumbled as he walked over to the kitchen to mix up a protein shake. “Speaking of people who don’t know their place...”

He pulled out his phone and open the video of Eva took earlier, hoping to get ideas on ways he could edit it. However, his reaction as soon as he started the clip was the one Caleb had hoped to avoid, especially after relieving himself with Casey and Fiona.

Sitting on his large sofa with his phone in his hand, Caleb found himself readjusting again as he did earlier and a tent was growing in his pants.

“What is wrong with me?”

As the video repeated on its loop, Caleb completely forgot about planning his edits and went into almost a trance at the way Eva’s body moved. Without even noticing, his hand was in his shorts and he was holding himself. He refused to admit it, but he was attracted to Eva — she carried herself with such an unshakeable confidence and managed to have a domineering attitude that was subtle, yet effective.

Caleb’s resistance in that moment faltered as he became harder and before he knew it, lotion was on his hand and it was wrapped around his length.

“I see this is why your fat ass goes to the gym,” Caleb jeered as Eva rode him. He was sitting on his couch while she was on his lap, facing forward and bouncing up and down his dick. “So you can ride my cock like a good slut.”

“Yes,” Eva moaned in response. “I want to make you feel good!”

Caleb groaned with pleasure and sped up his movements as his eyes closed and his head fell back.

“Then keep going,” he growled and smacked her ass. He firmly held her hips and admired the way her ass moved each time she came down. “Be a good whore for Daddy.”

Caleb began twisting his hand while stroking himself as he raced toward his release.

“Yes, Daddy!” Eva started moving faster. “Anything for you.”

“Shit!” Caleb grunted as he came all over his hand.

“Shit!” he shouted again after realizing what he’d just done.


“Good morning, Mr. Collins,” Eva greeted casually when Adrian walked into the office. It was the day after he’d kissed her in his office and Eva had not feelings about the incident while Adrian was very obviously nervous.

“M-morning, Eva,” he replied without looking at her. “Could you um... C-could you maybe... Can we talk?”

“Sure thing, Mr. Collins. What did you want to talk about?”

“I me-mean in... In my office.”

“Okay,” Eva shrugged and got up to follow Adrian. She wasn’t surprised that he continued to avoid eye contact, even after closing the door behind them and going to his desk where she sat across from him.

“So...” Adrian began. “About last night...”

He paused for a long time, fidgeting with his hands as he appeared to try to put the words together.

“I wanted to apologize to you again. It was completely out of line and as your boss, that makes it even more inappropriate.”

The room returned to silence after his apology. Eva didn’t have a response. She enjoyed the kiss and wouldn’t exactly object to more. However, she didn’t want to give Adrian the pleasure of knowing that. Plus, his obvious discomfort amused her — Eva found Adrian’s times of shy awkwardness to be endearing.

Following the long pause, Eva finally said, “Is that all, Mr. Collins?”

For the first time since they kissed the night before, Adrian looked into Eva’s eyes. “In addition to apologizing, I also wanted to check in with you. Are you okay?”

“I’m fine, Mr. Collins. Why wouldn’t I be?”

“You can still call me Adrian... If that’s okay with you. Are you sure you’re fine?”

“If the underlying question here is if I’ll file an HR complaint or sue you, you don’t need to worry about that,” Eva said flatly. “Besides, what you did is nothing compared to Mr. Peterson having sex with numerous employees in his office and somehow PMC Group has yet to be the subject of a workplace harassment or assault lawsuit.”

“Oh geez,” Adrian groaned. “You know about that?”

“It’s not exactly a secret. Plus, I’m your secretary, it kind of comes with the territory... Anyway, did you want to go over your schedule?”

Adrian scanned Eva’s face for any signs of discomfort. He’d planned to stop their one-on-one morning meetings out of fear of making her uncomfortable or losing self-control again. But now, given the fact that she seemed unbothered about the moment they shared last night, he wondered if it might be okay to continue.

However, before allowing himself to consider it further, Adrian opted to go with his original plan to cease their daily meetings.

“Actually, I think after last night, it might be better if we limit the amount of time we spend alone together. So let’s just change our system to something like what you have with Justin and you can print out my schedule and put it on my desk before I come in.”

“Oh, that was Justin— I mean Mr. Matsuda and I’s old system. We do one-on-one meetings as well now, especially since we spend so much time together on calls and what not... Anyway, I get what you mean and it’s no problem. I’ll do that from now on.”

Adrian knew it was wrong, but he was bothered by Eva’s lack of resistance to his request and it also irked him that she seemed to be getting closer with Justin to the point that she’d called him by his first name before correcting herself. Adrian was also hurt by the way she appeared unfazed by their kiss and Adrian’s decision not to have their regular one-on-one meetings that had turned into one of his favorite parts of the day.

“Right...” His jaw tensed as he clenched is teeth and tried to hide his uneasiness. “Thank you, Ms— Thank you, Eva.”

“Have a nice day, Mr. Collins.”


A/N: Whew! This whole chapter I was getting secondhand embarrassment from all the men. ANYWAY, the next chapter is one of my favorite that I’ve written for this book and I can’t wait to see y’all’s reactions!

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