Guess Who's The Boss? Ch. 02

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Jenna and William go out for dinner. We meet Jess.
2.3k words
4.25
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Part 2 of the 2 part series

Updated 06/08/2023
Created 05/02/2017
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"I'm not quite sure why he wants to take me out to dinner," Jenna screamed from inside her bathroom.

"Maybe he just wants to take you out of a formal setting after he saw what, as you call it, was a disastrous interview this morning." Her roommate, Jess said, peeping in. "You'll need to shave your legs if you want to wear a dress. Wait..."

Her eyes widened in horror.

"You are wearing a dress, aren't you?"

Jenna gave her a sheepish smile, looking over at the blouse and trousers she was planning to wear.

Jess rolled her eyes. "Stockings cover it for office work. This is a dinner."

She grabbed Jenna by both her shoulders and looked her in the eye. "You are on Impress Mode. You want this job. You have wanted this job ever since you moved here. You fucked up the first interview. This is your chance to make up for it."

At the end of her motivation, Jenna was in the bathroom, the door slammed shut to her face, razor in hand, and a dozen different emotions in her head. She turned the tap on and sat at the edge of the bathtub, thinking about everything she had to say. She glazed through all her notes and revised all the key pointers she had picked up through her days at university, and soon, she found her mind drifting off to the one challenge she had never though she would face.

Her soon-to-be boss was hot as hell, and she was sure she would never be able to take her mind off him. Him and his perfectly toned body... and the blue in his eyes... and the way his lips curled into a sly smirk when someone said something outrageously stupid... Stupid. Shit.

She checked the time, and with 20 minutes to go, she rushed out, and opened her closet to an abysmal selection of formal wear. Jess was back at her side in no time, munching on popcorn this time, and rolling her eyes further into oblivion as she shuffled through the little clothes that would be fitting outside the workplace.

"Remind me to take you shopping," she scoffed, "and until then, you'll be wearing one of my dresses, because frankly honey, I wouldn't be impressed with you in one of yours. And I already love you!"

She walked out of the room and was back before Jenna could call out her name to stop her, with three dresses neatly draped over her arm. She laid them out on the bed and the two girls started at the clothes for a solid two minutes before Jess spoke.

Picking up the first one, she went into game show host mode, giving a laughing Jenna a detailed description of what the dress was, what wearing it would entail, and what she would owe Jess if she decided to wear it.

She ended up picking a royal blue cocktail dress that was cut short at the knees, but had ruffles a little longer around the back. Jess watched her as she put it on over a dark blue, low cut bra and matching panties, and helped her zip it up, letting her pinkie brush against Jenna's skin as she went higher, and she was sure to let her hand linger at her neck for just a second too long. She walked around her to stand in front of her best friend, and took the liberty of sliding her hands down the deep neck of the dress, slipping her hands into her bra, grabbing her breasts and adjusting them well enough. Jess stood too close to the vanity table, and Jenna took the opportunity to push her against it, pinning her hands behind her back as she kissed her neck. Jess sighed, relaxing against the table as Jenna made her way up to her lips, kissing her full, exploring the way her mouth tasted like caramel, and at the end of the kiss, she smiled her own cocky smile, gently pushing Jess out of the way so she could proceed with her make up. She didn't forget to gently smack her on the ass as she scurried out.

She chose a deep red lipstick to go against the borderline slutty dress Jess had picked out for her, but let the rest of her face look natural to go with it. She left her hair down, setting the light brown locks into beach waves, making sure to let the golden in it be highlighted.

It was 8:05, and when she looked outside her window, wondering why Mr. Brown hadn't arrived yet, she saw the silhouette of what appeared to be a Cadillac, and taking her cue, she opened the door and stepped out, leaving Jess staring at her, mouth agape. A man stepped out of the driver's seat and walked around the car to her door. She stopped, and before he could open it, she asked him,

"What's your name?"

The driver was taken aback. "John, ma'am."

She looked at him with unsure eyes, and he understood. He nodded, an indication of confidence, before opening her door.

She got into an empty backseat, a little disappointed.

"Where are we going, John?"

"The Great Bay, Ma'am."

~

William checked his watch. 8:35pm.

He sat at the bar of The Great Bay Hotel, taking a swig out of his glass of whiskey before setting it down at the centre of the monogrammed coaster. The bartender seemed to have forgotten all her other customers at the other end of the bar, and he noticed her hover.

He checked his watch again.

Assuming that he had the time, he tore his eyes away from the door of the restaurant to entertain himself. The bartender's eyes lit up when she saw him looking at her.

"Can I get you anything, sir?"

"As much as I like the sound of that..." he trailed off, letting his dominance hit her as arrogance, and waited. He waited for her to subtly move away from him, and when she didn't, he went on.

"How about you repeat this?" He swirled the remnant of the caramel fluid in his glass, and before he could gulp it down and set it on the counter, she had another glass waiting for him.

He returned her kindness with a smile, making a note of what a talented woman she was, before glancing at the door again, and then at his watch, and back at the door.

That's when he saw her. She strutted in the doors of the restaurant with an aura of confidence around her. She claimed the room as hers, and turned the heads of every single man away from the women they were with. Who could blame her? That dress was... fuck.

The bartender was hovering, again. He didn't look at her. He couldn't. He just finished his glass with one long slug, placed a handsome tip on the counter, under his glass, and walked up to the woman who was going to be his newest employee, and couldn't stop thinking about all the other things he wanted her to be. He was focusing on being her boss at the moment, or else his attention would inevitably divert to her endless legs.

He held out his hand, and she went in for a handshake, the poor girl, but he held her hand and brought it to his lips, placing a gentle kiss on her fingers before letting it go. The way her eyes expressed shock was priceless.

"It's dinner, Miss Rogers. There are no handshakes in dinner."

The smile that she gave him to accompany a little chuckle made him laugh as well.

"Of course, Mr. Brown."

"Call me William," he smiled. "For now."

She laughed again. "Jenna."

The maƮtre d' walked them over to their table. As he was placing Jenna's chair back, William checked his watch again.

"Traffic?" he asked.

"Not a lot. John has been great."

William smiled. He'd known she was the kind of person to make conversation, and he pat himself on the back a little for selecting the right man for the job.

"I hope you don't mind, but I went ahead and ordered. You see, I had a little time on my hands."

Jenna blushed, visibly ashamed.

"I'm so sorry..." she begun to say, before William cut her off.

"No need for apologies just yet, Miss Ro... Jenna. As you and I both know, the interview you gave in my office the other day was," he took a sip of water, "not very charming." Jenna opened her mouth to speak, probably to apologise, but he put his hand up and she slumped back down in her seat. 'What a good girl,' he thought.

"But after reading every single godforsaken email your previous interviewers had sent me, I figured that the woman they went on and on about was not the woman who stepped into my office today."

The waiter interrupted them, and William paused, waiting for him to finish pouring the wine and leaving before he continued.

"The logical thing to do would have been to make my decision on what I had seen that day, but I'm a man that works by his gut, and my gut told you that there was more to you."

"Is that why you followed me to my office?"

William smirked, taking his time in drinking his wine, letting her grow uncomfortable in the realization that she had overstepped. When he was confident she had learnt his lesson, he went on.

"Your office is run by one of my oldest and closest friends, and forgive me if I fail to pay heed to your belief that the world revolves around you."

He went on, "Irrespective of why I was there, I do not regret being there. It gave me all the more reason to trust my gut."

He swore he saw Jenna's cheeks flush at the compliment. He could not help but return the smile that spread across her face.

~

Jenna's eyes met William's, and she could swear she saw more in those eyes than what she deemed appropriate. But who was she to judge? After all, it's not like she didn't have inappropriate thoughts about him.

She was the first to break eye contact, and while some might've told her it was weak of her to do so, she was not going to let the wetness of her panties grow.

"So, William. If I might ask... Why are we here?"

William smirked, and Jenna's eyes twitched as she stopped herself from rolling them.

"As I was saying before you interrupted me, your interview was abysmal, and when I saw you in I's.. Inaya's office, I knew I would have to take you to a setting in which the dark wood of my office won't be intimidating you."

"It's hardly the wood that intimidates me," she thought to herself, sipping on her wine. "So, tell me Jenna. What is it about the publishing industry that interests you?"

Jenna was the one to smirk, now. It is considered completely out of line to show up drunk to an interview, but of course the alcohol quantity of absurdness is different for dinners.

With her newfound wine-fuelled courage, Jenna began.

Over the next hour, the two spoke about the literature of today's era and drama, the ballet and the talent in the youth, and the spontaneity of attraction towards good content.

At the end of it all, Jenna knew that if she was ever going to be offered an internship at Ice, she would pounce at the opportunity. She told herself that it was because the work would let her learn so much, but deep down, she was fighting her desire to talk to this man even more.

~

William walked her to the car, and unlike her drive there, he actually got in from the other side, marvelling at her shocked expression.

She did not object, or even acknowledge his sudden imposition, and that both amused and disappointed him.

After a good twenty minutes of silence, he spoke.

"You applied for the internship at 'Ice' and while I do admire your humility, I'd like to offer you something better."

Jenna's eyes widened.

"Head of any department you choose."

He was surprised to see her wide eyes widen further, and let out a chuckle.

"I'm twenty seven," she said. "Am I even ready for this kind of responsibility?"

"Well," he said, reconsidering his offer. "You could start off as my assistant. Gain experience with each department and then see which one floats your boat."

"Holy fuck," she mumbled under her breath. He pretended to ignore that.

For the rest of the drive to her house, they both stayed silent. Jenna, looking out the window, obviously contemplating whether or not to let go of the job that has taught her so much. William, reminding himself to breathe, and trying as hard as he could to ignore the sexual tension in the car.

As John pulled over, William turned to Jenna, who was too deep in thought to notice that her destination had arrived.

"Jenna?" She snapped into the present. "We'd love to have you at 'Ice.' Think about it." He leaned over to her side, and heard her breath catch in her throat. He pulled her door open.

"I want an answer by Monday."

Jenna scurried out of the car, and he briefly considered following her and fucking her on the first bit of furniture he sees, but as she turned the kitchen lights on, he decided against it.

~

Jenna unlocked the door and stumbled into her house, slamming it behind her. She walked to the kitchen, flicking the lights on on her way there, grabbed a glass and poured herself some water.

Halfway through the glass she felt warm hands wrap around her waist, and she closed her eyes, sinking into the feeling of Jess' sweatshirt against her skin.

She turned around and kissed her, not stopping as they made their way to her bedroom.

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