Billionaire Dream

It was the opportunity of a lifetime for one lucky man, a year long mentorship with billionaire Lucy Stockholme.

There were plenty of attractive young men gathered for the event, an evening of presentations, where each applicant was able to present their business ideas in the hope that Lucy would not only mentor them, but also provide a significant grant towards achieving their dream.

The men thought the presentation was the sole criteria being judged.

Lucy, as always, was judging on one other important consideration.

“A glass of champagne, sir?” She held out the tray to the first young man on her path. He grabbed it, grunting something unintelligible and striding across the room.

“Thanks, love.” The next man was a little older, and he at least met her eye as he took a glass from her tray.

“Just what I’m after,” a third man took a glass of wine from her tray. “Thank you,” he glanced at her name badge, “Lily.”

Lucy smiled. “No problem, sir.”

His gaze burned into hers and Lucy sensed an attraction. “Call me Leo, please.”

She wandered the room, delivering drinks and canapes, making sure to serve each and every person.

“These are delicious.” Leo gestured to the oysters in garlic sauce. “Please pass my appreciation onto the chef.”

As each man stood to give his presentation she kept mental notes as to their ability to present a clear and concise argument for why her company should fund their dream, as well as the ingenuity of the idea, and how much it might be needed in the community.

In the end it came down to a tie between three men, Thomas, the older man who’d caught her eye, Alastair, the younger man who’d barely looked at her, and Leo.

Her CEO stood on the stage and thanked everyone for coming, announcing that the board of directors was retiring to another room to make a decision, which would be announced shortly. Lucy took her final tray of drinks around the room. She always liked to have a final test, and luckily enough, her top three selections were standing within close proximity of each other. She headed over, tripping at the last minute so the remaining drinks crashed to the carpet, splashing over the trousers and shoes of all three men, and several others. Lucy herself ended up on her hands and knees.

The younger man shrieked. “There’s champagne on my suit pants.” He yelled at her. “You useless klutz. You’ll be paying for my dry-cleaning bill.”

“Oh, get over it.” The older man chastised him.

“Lily, right?” Leo offered her a hand, a tingle travelling her arm as he helped her to stand. “Are you all right?” he asked, concern furrowing his brow.

“I’m so sorry.” Her gaze flicked to his and away again, as she rushed to gather up the tray and the spilled glasses.

“And so you should be. Do you have any idea how much these trousers cost? Far more than your yearly wage. You ought to be fired.”

“For goodness sake, shut your trap!” Leo snapped at him as he bent to help her collect up the glasses. “Have you never made a mistake in your life? How about you help?”

“Do I look like the wait staff to you?”

~

Twenty minutes later Lucy was transformed. She’d pulled her hair loose from the bun it had been in while she was dressed as the waitress named Lily, and now it cascaded around her shoulders. She’d applied a fresh layer of make-up, and wore her a specially tailored suit, befitting her position as Company Director.

She stood up at the podium, announcing Leo’s success. The crowd clapped politely, and Lucy stepped down from the stage to meet Leo as he crossed the room.

His gaze roved over her body, and Lucy smirked to herself.

“Congratulations.” She shook his hand, another warm tingle shooting up her arm. “I look forward to spending some time with you.”

His gaze came to rest on his face, and he raised an eyebrow. “I look forward to spending more time with you, too, Lily.”

Lucy grinned. “Do you know I could go and shake Alastair’s hand and he would have no idea I was the same person who spilled wine on his expensive suit.”

“So it was a test, then?”

She nodded. “It was. The wealthier we get, the easier it seems to be to forget that those people less fortunate enough are humans, too. Everyone deserves respect. And what Alastair and those like him seem to forget is that if everyone was rich and expected to be waited on, there wouldn’t be anyone to serve the wine, or prepare the food, or clean up after accidental spillages.”

~

As the year progressed, Leo was a perfect gentlemen, and quick learner. Though Lucy sensed his attraction he never once crossed the line, remaining perfectly professional at all times. There were days the air was thick with desire, and Lucy wished he’d just kiss her.

She couldn’t make the first move, she was in the position of power in this relationship, and there was no way she was going to take advantage of that.

All too soon the year came to an end. Leo’s business was flourishing, the injection of Lucy’s time and money, and his hard work, had brought him the results he’d hoped for.

“Can I take you out to dinner?” he asked at the end of their last session together.

Joy swelled in her chest. “Of course.”

He picked some place expensive, arrived in a new suit to pick her up.

He was gorgeous; and after a year spent working together he knew her as a person, not a rich figurehead, and treated her as such, making her laugh in ways no one had for a long time.

“I know this is quite forward of me,” he said as dinner drew to a close. “But you’re a beautiful woman, and I don’t know if I’ll ever see you again after this, so I was wondering if you’d like to come back to my place?”

~

Leo’s place was a small minimally furnished two-bedroom flat, not that Lucy got to see much of that.

Now he’d made the first move, Lucy had let loose, and they left a trail of clothes from the front door all the way to his bedroom.

His cock was thick, and Lucy loved the feel of it in her hand. But despite how submissive he’d been while learning from her, in his bed he was completely different.

“You can play with that later,” he growled, pushing her back onto the bed to bury his face between her legs.

He kept one eye on her as he circled her clit with his tongue, sucking and kissing, then shifted slightly to lap her vulva and explore her folds.

Lucy fisted the bedsheets, moaning and writhing as he found all her most sensitive spots and played with her till she came, crying his name as an orgasm tore through her body.

He sat up on his knees, a damp grin on his face.

“All right,” he said. “You can play now.”

She laughed, pushing herself up into a sitting position to grab his cock again. “Thank you, sir.” She got onto all fours, taking him in her mouth and sucked him as she played with his balls, rolling them between her fingers, stopping now and again to lick up and down his shaft.

He groaned. “That feels even better than I imagined.”

She grinned up at him, around his cock, and continued to bob up and down, increasing speed as his moans and groans spurred her on.

“I’m coming.” He gasped, as a shot of warm cum hit the back of Lucy’s throat.

She swallowed, sucking and licking him clean.

“Fuck.” He dropped back onto the bed, his gaze on hers. “That was hot.”

“It was, wasn’t it? I’m glad you asked me out to dinner.”

“Well I figured you weren’t going to ask me.” He laughed. “So what now?”

“What now? Well my pussy is still waiting to be filled, so I very much hope that isn’t it for the night.”

His cock pulsed in response, and Lucy grinned. “I’ll take that as a good sign.”

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