Chapter 1: Nocturnal Beginnings
A/N: This plot is loosely based on a story I read. I hope you enjoy.
Bonnie Sheila Bennett was a formidable woman. Hell, in her will she purposefully wanted some reference on her tombstone of how revered she was. The former wife and mother had to be in this world of business. Being both a woman and one of color to be specific made the hoops she jumped through entrenched with fire and barbed wire.
Let's just say she's earned her dues.
Her father, Rudy, saw her ambition from a young age from the way she fiercely argued with her siblings and conquered each debate. His little girl was a complete firecracker and he saw a profit in the midst of her fiery personality.
Law was a first and natural career choice for the gifted girl. It changed into business after a standard take-your-kid-to-work day at his law firm when she was 13. Her younger brother, Darryl, and sister, Crystal complained how boring it was the commute back home to their place in Brooklyn.
Walking with the busy people invigorated Bonnie's adolescent spirit and from that very day she vowed to be that big boss with the grand window that peered at the many other skyscrapers in Manhattan.
Even though she was high-ranking at her company, the college-educated woman's ultimate goal was to be CEO before she was 40 but she was content with being the company's CFO. Or she wasn't and secretly was plotting on the haggard old man she called Dad to finally retire so she could take over the firm.
Right now the 5'2 woman was speed walking with or *ahead* of her struggling assistant to the elevator. The somewhat awkward assistant had been the only one she had kept longer than 3 months. He was a blonde kid, fresh out of college with his undergrad in business law.
"Ms. Bennett, I think your schedule looks completely free today. I can head to the accounting office and see if there 's anything they want you to approve."
She turned towards Luke. "Listen Parker, the first thing you should know about time is that it is not free. I always have something to do or a deadline to complete."
"Of course," The elevator dinged and they walked out together, headed in two different ways. Luke handed her schedule and she verified it—there was virtually no hard work for her to complete. Then again it was Friday so she met the majority of her quotas earlier in the week.
At 3pm, she texted her daughter asking how her day was and got a vague answer back saying that it was okay. Oh, and also that she was going over her friend's house and that her father would send a car for both of the girls to travel in. Bonnie sighed sadly before putting her phone to sleep.
More work was bandaged her wounds about not being able to fulfill her duties as a weekend mom. Truthfully, she felt terrible and had no other choice but to take her consequence for separating the family. This was the 3rd time in a row that her adolescent daughter, Amaya, ditched her for her friends or some school event.
Bonnie met with her fellow financial advisers around 4 and was done in the next quarter hour. All of them grabbed all of their belongings and were out the building before 5. She was still in her office checking her emails before Luke interrupted her replying to a customer.
"Knock before you enter," She gritted through her teeth.
"I'm sorry, Ms. Bennett. Almost everyone is gone except Stefan, Caroline and the cleaning staff. What do you want me to say?"
"The security team is supposed to be present 24/7, it's what I pay them for—mines and my employees full safety."
"Okay," He pursed his lips. "and before I leave is there anything you want?"
"Nothing at all, you can go."
"Are you sure-?"
"Luke," Bonnie smiled, her face with an almost sad expression. "Have a nice weekend and I won't tell you to leave my office again." He gulped, nodded, and sprinted mainly in fear that she would call security to escort him out.
Later on, Bonnie was interrupted yet again. She looked up to see her sassy friend, Katherine, dressed in a rose gold dress suit. Being a lawyer definitely had to be her second career choice after modeling.
"Caroline is totally crushing on the NYU boy, he's way too pretty for her if you ask me."
"I strongly advise people not to engage in workplace romances, but wait—Salvatore?"
"Yeah," The woman in tall heels confirmed. "I think he's just trying to be nice since he's new. Anywho, guess what?"
"I don't play the guessing game." Katherine rolled her eyes.
"Your best lawyer settlement's check just cleared." She sang happily.
Bonnie narrowed her eyes. "You mean your client's?"
"Well," Katherine popped her glossed lips, walking closer to Bonnie's desk. "Technically yes, but I got him to agree on a 25% cut."
"Mmm, maybe this isn't the career for you, the fashion industry is pretty big here." Bonnie said sarcastically.
"Oh, Bonnie, you know how much I love to prove my counter wrong and it just intensifies when the person is a man. I am currently 12-0 in my cases and I want to go out so I am dragging you with me," Katherine announced, looking at her friend who crossed her arms defiantly.
"And I'm not taking no for an answer, boss." The brunette emphasized.
"I just wanna go home and soak, no sulk in the tub, and reflect on the mistakes I've made as a mother and wife," Bonnie stood up in her designer tan suit, showcasing her height of 5 '2 ish in heels.
"Oh my god," Katherine said in realization-it was January. "It's around that time of the year."
"What time of year-" Bonnie coughed as Katherine hugged her tightly.
"Your divorce was finalized 3 years ago today, I know you aren't fine."
They broke apart and Katherine watched Bonnie's stoic eyes with great concern.
"I'm fine, I swear I am. Maya didn't have time to hang out with me this weekend, it's okay I'll just try again next weekend."
Katherine came towards her and linked their arms together.
"Bonnie...you can't keep locking yourself in your condo every weekend. I need you to live a little, so we're going to go shopping tonight, post some pictures on the 'Gram, and go to the club."
"That sounds awful and more geared for attention-seeking people in their 20's with no tangible career."
Katherine grabbed the woman's purse and handed it to her. If they were going to shop then she would need that magic black card in her wallet.
The shopping ironically went rather quick for Katherine standards. They knew their sizes and the blonde knew what exact night attire she wanted her friend in and discarded most of Bonnie's suggestions. She eagerly swiped their cards and Bonnie reluctantly verified her personal PIN number.
Bonnie's driver left his seat to put all the bags away for the women. There had been about 15 of them from three different luxury designers since neither of them were big fans of mixing brands.
Katherine sat comfortably with her legs crossed, sipping on rosé wine in Bonnie's walk-in closet. They (she) thought it was best if the businesswoman tried on all the outfits she bought before deciding which one was perfect for the night.
"This is like the fourth mini-dress I have tried on, please tell me that you like it," Bonnie told her.
"Hmm, turn around." She did as asked. "No, we have to go through the rest."
Bonnie rolled her eyes, and flipped Katherine off before heading back inside in her closet to change once more.
...
Katherine's eyes widened as she gulped the rest of her glass hurriedly so she could speak. Bonnie was clad in a red satin mini dress. That was all what was different from her usual appearance but it made Katherine cheer and applaud.
"This is the one."
"Thank God," Bonnie exaggerated, stripping out of it and revealing her cotton underwear set.
Katherine shrieked in horror as the woman hung the dress on a hanger. "I know you aren't wearing another set of those to the club."
"They're breathable."
"Yet totally not sexy, I know you used to spice it up when you and Luka were together." Bonnie rolled her eyes.
"Just because you two are history doesn't mean she can't have any other mates," Katherine said with a suggestive flare in her voice.
The thought of Bonnie sleeping with some random stranger made her want to hurl. She wouldn't know their last name, political alignments, financial and social standings.
Bonnie Bennett at the ripe age of 35 would not be giving her goodies away to some barfly. All she did was lift an eyebrow at her friend's vulgar suggestion.
"I'll consider it. The underwear, not being loose."
"Okay, and I might have forgot to mention that I am bringing a date-ish and he wants to bring his friend too." The stylish woman spoke all in one breath.
"What? Kat, I have no interest in playing a double date tonight."
"Look, I already told my partner that you aren't really talkative so his friend won't force you to talk to him—unless you want to." Katherine informed her.
Bonnie had a T-shirt on and hugged herself. She felt more comfortable knowing there wasn't this immense pressure for her to be paired with the other third wheeler. Hell, she had to entertain herself when Katherine would eventually leave her to go mingle.
"So. Where did you meet him?"
"Oh, on a sugar baby website," She answered casually.
"What, why and how long have you been doing this?"
"Um, we've been pretty non-exclusive for three months now and yes, Bonnie I do pay him for his time."
"But-but you don't have to pay anyone to date you, you're stunning, Katherine," The CFO stammered, in utter confusion.
"Guys in their early to mid twenties aren't that eager to date me because of how fierce I am and they damn sure don't want to keep things super exclusive and that's what I want: a good time." She turned around to face Bonnie's face and saw that her mouth had an 'O' shape.
"No constraints, no complications, and more importantly no drama. Just fun."
Bonnie snapped her fingers trying to recall her memory. "What about Mikael...? Mikaelson! Elijah two doors down from your office, you should see the way his face lit up that day at the meeting."
"Bonnie, that was a month ago, we're flirty at work and have went out on a date once but he wants something long-term and I do not, so-"
"Wait, you slept together?"
"Well," Katherine quipped, looking down. "I don't kiss and tell but he did wake me up to the smell of English muffins and freshly squeezed orange juice. So, naturally, I had to get out of there."
Bonnie held the sides of her head. Her friend was nothing short of aggravating.
Bonnie and Katherine stepped out of the limo, and onto the pavement. Bonnie consciously covered herself up despite wearing a black mink coat over her dress. Whereas Katherine exuded confidence and familiarity with her fur coat over the shimmery, golden v-neck dress she wore. The eccentric longtime friend looked over to see two dark-haired males standing in line.
Katherine pointed and waved at their company for the night. "Hey, I see our-I mean my date and his friend who will not totally try to pursue you tonight." Bonnie looked at her as she corrected herself. Katherine grabbed her hand skipped to the front of the line.
She was instantly greeted by the tanned skin one who seemingly had a Valley accent. Clearly, Katherine had a type; brainless and pretty. Bonnie analysed how close they were, they didn't look like what she perceived a traditional sugar mama and their sugar baby. Katherine was older sure, but her and Mason looked like an actual couple.
The younger man squeezed her thighs and kissed her. "Mmm-mmm, you are even hotter than the last time I saw you."
"Oh, please. You're only saying that because I pay you for compliments."
Mason rested his hands on her hips and kissed her face. "Don't believe that for a second."
Bonnie felt their intense wave of heat even with the never-ending winter air blowing around them. Mason was a bit too saucy for her liking but she had to be fine with it on the accord of Katherine. The chemistry was so palpable between them as they shared immediate eye contact. Bonnie conveniently checked her phone as they fondled and kissed over and over again. She saw in her periphery that Mason's mysterious friend had done the same.
It wasn't until the bouncer interrupted their PDA and asked for ID. The quartet found their way into the club and settled in a booth. They found one to their liking; two loveseats facing each other. The women sat across the men with their legs crossed.
"Okay, people this is my best friend from college and boss Bonnie, this is Mason, Bonnie and that right there is Mason's friend, ugh I never got your name, I'm sorry."
"Damon," He told her but was looking at Bonnie, who'd straightened up under his mesmerizing eyes. A strong arm reached out to her, and she was less flustered by the action. He was offering a handshake and she had completed a dozen of those a day.
But this one was different than all the others. She quickly took her hand back and placed it on her purse.
"Nice to meet you, Bonnie,"
"Likewise," She choked out.
Katherine kicked her ankle. "Way to be so formal," She gritted.
Bonnie kicked right back. "I'm trying."
The two men stood up, declaring that they were going to get drinks for everyone. They came back shortly with two Long Island Teas for the ladies. After too much chit chat for Katherine's liking, she stood up.
"I am slightly buzzed which means I am ready to dance, with or without someone," The woman alerted them, and left them by sashaying away.
"Buzzed? She's not a lightweight," Mason said aloud.
"Yeah, but she was doing some pre-club drinking at my place.
He looked over to see the woman of hour wildly swinging her hips. "Ah,you know what? That makes sense, I'm gonna check on her."
Mason left and then there were two.
"Katherine mentioned that you're her boss, in our conversation, it feels surreal now that I've seen your face," Damon said, drinking in her appearance.
"I am. I convinced her to work at my firm on the merit of our relationship and we've been like that ever since."
Damon smiled. "Ooh, so you own the firm, you must be the Big Boss, then."
"You make it sound like I'm a villain," Bonnie scoffed. "I don't own the firm but I play a key role in maintaining it. I call it mine because it is and I call the shots."
"Quite the contrary on the villain part, I actually admire how self-assured you are about your position. It's actually kind of sexy."
"Thank you, I think." She eyed his ring shining in the club's lighting. "Is that a Lapis lazuli?"
"It is, family heirloom."
"It's beautiful," Bonnie complimented keeping her eyes on the ring and then to his face, that was watching her. She smiled genuinely for the first time today.
"So, what do you do for a living?" A part of her knew the answer.
"Well, for starters, I am self-employed, that's how I start out explaining my work."
Bonnie clapped slowly. "Bravo. I am a firm believer of the autonomy of working people. I try to give my employees as much leeway as possible."
"That's amazing. I am a male entertainer, sugar baby, boy toy, if you will."
Bonnie sighed. Mason was his best friend so it would make sense for him to be a sugar baby as well. She nodded and tried to understand it but her body failed to give an open-minded reply.
"Yeah, I don't get it, this 'world' is new to me. It seems like you're selling your body for money."
"That's the biggest misconception about this world, I've had sugar mommas who just wanted my company, to just make them laugh."
"Okay." Bonnie nodded again.
He leaned in and spoke in her ear and she naively allowed him to. "Sex is something that her and I agree on, and is simply just a benefit to the job."
The way words oozed out of Damon's mouth made the short hairs on the back of her neck spring forward. She retreated back to her seat feeling small. She felt faint at this touch and she wanted to conceal that.
"Bonnie." The woman faced him after he called her out. "Do you want to get out of here?"
The question was so open-ended and she wanted to analyze each meaning but opted not to. For once, the proclaimed boss lady took an actual risk. She looked at Katherine and Mason practically slobbering on each other on the common floor. They wouldn't notice or care at the moment if the two of them left or not.
"Yeah, let's leave," She said coolly.
Damon stood up, smiled, and extended his hand out like a true gentleman. Bonnie gulped and looked up hesitantly. Was this normal? She knew once she walked out with him then she would be going against everything she thought she stood for.