Faking It With The CEO

Oliver Sterling, the CEO with a winning personality and drop-dead looks—sharp jawline, mesmerizing green eyes, perfect nose, luscious lips, bushy eyebrows, and sleek black hair. Standing tall at 6 and a half feet with an athletic build, he strutted through his office holding onto a bunch of papers. Emily, his hyper-organized secretary, stood there all prepared with her clipboard.

"Hey, Ms. Collins, what's my schedule for today?" Oliver flashed his usual charming smile, eyeing Emily's simple yet sharp look.

Her ginger hair is styled in a neat bun, and a no-nonsense outfit consisting of a dull-colored long skirt, an old-school blouse, no makeup, thick glasses, and pink lips. Those lips were the only colorful thing on her.

"Good morning, Mr. Sterling. Here's the deal for today's meetings." Emily handed over the clipboard. "Your 9 am got pushed to 10, and the Johnson account review is happening this afternoon."

"Got it. Thanks, Ms. Collins. What about that Jenkins project report?" He quickly scanned the notes, multitasking as usual.

"It's already on your desk, sir," 

Throughout the morning, Emily expertly managed Oliver's schedule, handling all those tiny details he tended to overlook. He barely acknowledged her when she took his jacket as he headed to his desk.

"Thanks, Ms. Collins," Oliver replied, still glued to the clipboard.

"No problem, Mr. Sterling,"

During the office commotion, a reminder pops up on Oliver's calendar: "Family Dinner - 7 p.m." 

His expression changes upon reading the reminder. 

"Ms. Collins, can you clear my evening? Family dinner at 7" 

"Consider it done, Sir" 

After wrapping up the day's meetings, Oliver was feeling accomplished yet worn out. He settled back into his office, thoughts still racing from the meeting earlier.

"Let's push the marketing presentation to tomorrow morning," Oliver decided, his voice showing fatigue.

Emily nodded, quickly noting down the change. As she moved closer, she noticed his tie was a bit wonky, and there was a strand of hair out of place. Without a word, she stepped up and effortlessly fixed his tie. Then, almost like second nature, she smoothed down that stray hair, making sure everything was back in order.

Lost in the papers on his desk, Oliver barely registered Emily's attention to detail.

Oliver glanced up, an air of fatigue still evident in his eyes, but a faint smile gracing his lips. "Thanks, Ms. Collins. You always have an eye for detail."

"It's my pleasure, Mr. Sterling," Emily responded with her tone as composed and professional as ever.

As Emily reached for a document, she glanced at the window's reflection—a reflection showing Oliver with a tidier appearance, courtesy of her discreet touch-ups.

“You can leave early,” Oliver reminded before leaving the office.

……..

Oliver strolled down the familiar path to the Sterling family dinner, a grand mansion. The fancy marble floors and extravagant décor greeted him as he entered the grand hall. His grandparents, the esteemed figures of the family, greeted him warmly. 

"Oliver, my boy! Wonderful to have you here!" his grandmother exclaimed. 

"Hey, Grandma, Grandpa," Oliver replied, giving them each a hug. 

“How's work?” Grandma inquired, motioning for him to take a seat.

He shrugs, “Well, busy as always”

“I heard your folks are still in France?”

“Yeah, Nana. They'll be back next month, I think.”

“Oh, that lovely couple”

During the meal, the topic he expected was opened by his grandfather. Give it to his grandfather to open pressing matter in the middle of the meal.

"Got any special lady in your life, Oliver?" his grandpa asked without any reserve like always.

Oliver chuckled, knowing this drill too well. "Nah, Grandpa. Just hustling hard at work."

His grandma jumped in with a teasing tone. "Come on, darling. A successful guy like you ought to have a charming lady”

"I'm savoring my free time, Nana."

"But it's about time you got serious about finding the right one. There's this amazing girl at the charity event next month. What do you say? Interested in meeting her?"

Oliver let out a strained chuckle, glancing briefly at his grandparents. "Grandma, appreciate the suggestions, but I'm focusing on work right now."

Despite his outwardly charming smile, the constant matchmaking attempts were suffocating him. He couldn't bring himself to tell them about the someone already on his mind—a person he longed to introduce but couldn't, no matter how much he wished for it.

"Oliver, the charity event next month means a lot to the family. It's about time you brought someone special around."

Oliver gripped the fork a bit tighter, "Grandpa—"

"We keep on postponing that plan since you always told us that you already have someone but it's been 4 years and we still haven't met her. If you haven't found someone suitable by then, I'll take charge and find someone perfect for you."

His grandpa's words weighed heavily on his shoulders, knowing that his grandfather would do it in a heartbeat. Or worse, his parents would support it.

As the night wound down, Oliver found himself sitting in his car driving back to his penthouse, and dialing Emily's number without hesitation. 

"Hey, Ms. Collins, did you drop off the food and flowers at my place?" 

"Yes, Mr. Sterling. Everything's sorted," Emily confirmed, her voice calm and composed as always.

Soon after, Oliver reached his penthouse and was greeted by the delightful smell of the meal Emily had set up in the dining hall. But what caught his attention wasn't the food—it was the elegant figure sitting there.

Sophie, his secret girlfriend, was lounging in one of the seats, looking effortlessly beautiful. She was a rising star in showbiz, known for her killer performances and graceful vibe. She was beautiful with her dark blonde hair like a smooth waterfall of waves framing her perfect face, and her blue eyes sparkled as she noticed Oliver walking in.

A real smile spread across Oliver's face as he made his way over, planting a sweet kiss on Sophie's cheek. 

Sophie flashed him a knowing grin. "Hey there, handsome. Your secretary has great taste in food."

Oliver laughed, "Yeah, she does. Do you like it?"

"Absolutely," Sophie said, giggling. "It's delicious."

“I'm glad you like it”

Sophie smiled at her, “So, how’s work? Did you come from meeting your grandparents?”

He sighed tiredly, “Yeah, I am”

“But why do you look like that?” she frowned, holding my hand.

With his grandpa's ultimatum weighing on him, Oliver decided to bring up the topic.

"Sophie, there's something I gotta talk about," Oliver started, sounding a bit nervous.

"What is it?"

Oliver drew in a deep breath, now playing with her fingers, "The charity event is coming—it's expected that I introduce someone special to my family."

Sophie's frown deepened, realization dawning in her eyes. "You mean….us?"

"Yes. I've been considering whether it's time for us to meet my family?"

Sophie's expression shifted, a flicker of concern crossing her features. "Oliver, you know how crucial my career is right now. News of my dating could affect everything, especially at this peak of my popularity. And you know your family can be quite overly excited and publicize it"

His family being criticized irked Oliver, but he brushed it off. No matter how much he assured her that his family would not do it, she still wouldn't believe him.

Oliver nodded again, "I understand, Sophie. We've kept it private for four years—I'll handle it."

Sophie's eyes softened, "I'm sorry, Oliver."

She leaned in, planting a gentle kiss on his lips. But when he didn't respond, she pulled back.

"Ollie, seriously, I'm really sorry," she apologized once more. “Please, just this one last time”

Oliver smirked, snaking his arm to her small waist and then under her shirt to fondle her breast. He immediately heard her moan. Then he leaned to her ears, whispering, 

“Baby, you should show how sorry you are in other ways”