Dinner with Oscar

Later that evening, Oscar sent his driver to pick her up at her place. This time around, she went for a classy look in her navy Tom Ford blazer dress.

She paired the look with a black blunt-cut bob wig, minimal jewelry, and a pair of black YSL sandals. Her makeup was cool, and she opted for a mild fragrance too.

“You look phenomenal,” Oscar commented when she met him on his rooftop terrace where they would be dining that night.

“Thank you,” she acknowledged his compliment with a smile.

“And you look…the same,” she said with a laugh. He was dressed in his usual formal attire comprising a dark suit, a crisp white shirt, and a black tie.

Oscar laughed. “Yeah, I’m boring like that.”

They sat at the table that had been set for two and shared a drink. The ambiance was serene and alluring. It was a perfect setting for romance or falling in love.

At Oscar’s insistence, Vivian scanned the menu that had been laid out on the table for her. She requested a pasta dish with grilled chicken and vegetable salad. Her host went for a seafood dish with stir-fried veggies.

While they waited for their meals to arrive, they had a light-hearted conversation to get to know each other better.

“I’m a junior at UCLA,” she informed him. “I’m studying Fine Arts. I love it, and I can’t wait to graduate and put my skills to good use.”

“You don’t have to wait till you graduate before you start testing out your skills, you know,” Oscar said.

“Sure. I have a bunch of amateur paintings I’ve done over the years. I tried selling some not too long ago when I was so broke and being hounded by my creditors. Unfortunately, nobody would buy them.”

“Ouch.”

“Yeah. Not many people appreciate art if it’s coming from an unknown newbie like me. One of my uncles once told me that I was wasting my time going to school to learn something that everyone can do. He said I’d never make it in life if art was the only thing I knew. His words hurt me, but when I was unable to sell my paintings to get out of debt, I started to wonder if he was right.”

“I disagree. Every famous artist in the world today started as a newbie. Give yourself some time to grow.”

“Sure…”

“I would love to see your paintings if you don’t mind.”

“Really?”

“Yes. As you said before, not many people appreciate art. Your uncle might be in that category, but I’m not.”

She appreciated his attempt to make her feel better about her craft. “Thanks.”

Their food arrived along with a bottle of vintage wine. It almost seemed like they were a regular couple on a proper date.

“So, are you going to tell me about yourself?” She asked after the servers had left. “And please don’t tell me what I already know, such as your career and how you made your first billion. I’ve done my homework, and I already know all that.”

He chuckled. “What else do you want to know then?”

“I want to know what the media and G****e don’t know,” she replied boldly.

Oscar smiled. “You already know I like me some kinky action behind closed doors, right?”

“Yup. What else?”

“I’m an orphan, and I was raised by an aunt – my mother’s younger sister. She was a stay-at-home hooker.”

“A what?”

“You know, a hooker who did her business at home. She didn’t have a pimp, didn’t go to the brothels or the streets. She did her stuff at home.”

“Oh.”

“Her clients came in to transact with her, and if I’m home, I get to watch the show live. I was six when I started living with her.”

“Aww, that’s terrible,” Vivian said, feeling sorry for him.

“I lived with her till I finished high school. That was in Houston. When I got a scholarship to continue my education in L.A., I moved out of her house and never looked back.”

“That’s understandable.”

“She did her best to feed me and take care of me for many years, which I’ve always been grateful for. But she exposed me to a lot of messed up things that I had no business knowing as a child.”

“I’m sorry you had to go through that,” Vivian said softly. “It must have been a nightmare for you growing up in such a toxic environment.”

“Yeah, well…” he said with a grin. “I’ve had years of therapy to reset my mind and let go of whatever pain I experienced in the past. But the therapies didn’t fix my voyeuristic tendencies.”

“I see…so you still like to watch,” she said with a knowing smile.

“Yes, and I genuinely enjoy it.”

“More than having sex?”

“Way more than having sex,” he admitted.

“So, you don’t have sex?”

Oscar sighed. “I do have sex, but when that happens, I tend to hate my partner after the act.”

“Hate? Why?”

He shrugged. “It’s a psychological thing. One of my therapists said in my mind, I see my sexual partners as my aunt, and that is why I hate them after sleeping with them.”

“Is that why you haven’t had sex with me?”

He nodded in response.

“Wow. So, I better enjoy this phase for as long as it lasts, yes?”

Oscar chuckled again. “I like your personality, and for some reason, I want you in my corner always. I don’t want to call the matron to send me any other girl; I just want only you. And now that you’re no longer affiliated with her, I think it’s a done deal, right?”

Vivian didn’t mind having him as her only client going forward. That’s less work for her yet more money. She felt like she’d hit the jackpot.

“Deal,” she said with a grin.

“Perfect!” He exclaimed excitedly. “I’ll place you on a monthly salary, and you’ll get some cash upfront to shop for whatever you want. You’ll get to travel with me on my overseas trips, and you’re free to come here as often as you like.”

“If I didn’t know better, I’d think you were recruiting me to be your girlfriend.”

Oscar laughed. “You’re my professional girlfriend.”

“I like the sound of that,” Vivian giggled. “In fact, I think I need to celebrate my new position.”

“What do you mean?” Oscar asked suspiciously.

In response, she unbuttoned her blazer and let the jacket drop around her waist on the seat. She wasn’t putting on underwear, so her full boobs were exposed for him to get an eyeful.

“Damn, Celia,” he groaned, obviously enjoying the view.

“It’s Vivian,” she corrected him. “My name is Vivian.”

“Vivian,” he repeated slowly. “Suits you perfectly. I love it.”

“Do you love this too?” She asked as she cupped her boobs with both hands and began to caress them gently.

She leaned back in her chair as she continued to massage her breasts, then she slid one hand down her body and began to stroke herself between her legs. Oscar watched her with glazed eyes, and she knew he was turned on.

Vivian moaned as she worked herself, tweaking her nipples, massaging her core, and having an all-around good time. When she noticed that his breathing was becoming shallow, she stopped.

She didn’t want to tempt him into pouncing on her and having sex with her right there. That would automatically terminate her contract with him before it officially began.

We can’t have that now, can we?  she thought wryly. There’s too much money at stake here.

Vivian quietly got dressed and continued eating as if nothing had happened. Anyone walking in on them right now would assume she’d been eating all along.

“You’re really good at this,” Oscar said with a satisfied smile. “I definitely chose the right one.”

“You bet your sweet billions, you did,” Vivian giggled. “Eat up, boo; I’d like you to show me around the house when we’re done here.”

“Sure thing,” he said. “You’ll love this place.”

“Who wouldn’t?”

Oscar laughed. “There’s more to me than my money, you know?”

“Of course, don’t mind me. It’s just that I’ve never had any sort of relationship with someone of your status before. So… pardon my excitement.”

“It’s fine. I find your honesty quite refreshing, so don’t feel the need to act properly around me or try saying the right things. Just be yourself. That’s what attracts me to you every time we meet.”

Vivian smiled. “I’m happy to hear that.”

He watched her eat for a while before speaking again. “I think this is going to be an interesting relationship,” he said with a smile.

“We’ll see,” she said coyly and sipped her wine.