Disclaimer: This story is based on characters created by L.J. Smith, as portrayed in the TV series created by Kevin Williamson and Julie Plec. The plot is based on the novel The Cardoss Luck (1974) by Janet Louise Roberts. All rights to their respective owners. No copyright infringement intended.

Author's Note: Ok, so another AU/AH story for ya : ) This, as I mention in my disclaimer, is based on a romance novel set in aristocratic Regency England. I'm moving it to 19th century Mystic Falls. I'll put up a "family tree" on my LJ to explain the connections, but all will be revealed throughout the story. Most importantly, Damon and Stefan are cousins, not brothers, and Katherine and Elena look nothing alike. This is purely a work of fiction, and I will bend time and language to my will, meaning this can in no way be viewed as a proper period piece, although I have aspirations to make it believable. Enjoy!

PS: Thanks to tamilnadu09 for helping with the title… I would not be publishing this tonight without your help! : )

FORTUNE FAVORS THE BRAVE

~ Prologue ~

Elena Gilbert's doe brown eyes scanned the ballroom. Over there was Mason Lockwood, who had paid her much attention since she first arrived in Atlanta and ventured out into society.

This was all very new to her. She hadn't grown up with money. Instead, she had lost her parents at a young age and was taken in by her uncle George. He had treated her much like a servant, and she had done everything he asked. She cooked, cleaned, taught his children and nursed him when he fell ill. Not a word of gratitude fell from his lips. Instead, all Elena ever heard was what a burden she was to him and his family. Nothing she did was ever good enough.

George Gilbert's two sons died on the battlefields of the South, and when he himself took his leave of this earth, Elena was his only living relative, apart from his other brother John, whom George had never gotten along with. Thus, he bequeathed all his worldly possessions to Elena, with the stipulation that she marry. Until she did so, John Gilbert, a greedy and cruel man, would manage her inheritance.

During this past year since George Gilbert died, John had somehow managed to squander half of the fortune. If Elena didn't find a husband soon, there would be nothing left. And that was why she was scanning the ballroom of the Lockwood mansion in hopes of finding a man who would agree to marry her whilst leaving all romantic feelings at the door.

Elena didn't want a man in her life. All her life she had been subject to the guardianship of men. One year spent as a married woman and she would be free to use her inheritance as she wished. As soon as she was married, John Gilbert would lose all access to the Gilbert fortune.

"Miss Gilbert, you look as though you are million miles away," a smooth voice drawled.

Elena blinked to find Mason Lockwood standing before her, a charming smile gracing his full lips. She liked Mason. He was well-behaved, polite, attractive. He was the sort of man she could see herself falling in love with. Which was exactly why he was out of the running.

No, she needed someone who was willing to accept her conditions and who also had something to gain. Mason Lockwood was already rich. She couldn't offer him anything in return for his cooperation, other than her heart and body. And that was a price Elena was not willing to pay.

"I apologize, Mr. Lockwood. I was admiring the many art pieces. Mrs. Lockwood has excellent taste."

"Indeed. My sister-in-law has gone to great lengths to make the ballroom appealing to all senses. For example, the string quartet will begin playing shortly. Would you like to join me on the dance floor?" he said and offered his hand with a slight bow.

"Of course, Mr. Lockwood. I would be delighted," Elena replied sweetly and slipped her gloved hand into his.

As they danced several turns around the room, Elena caught sight of a most peculiar occurrence. A door at the far end of the room had been left ajar and inside she could see what appeared to be a card game going on. That was not what caught her interest, though. It was a pair of piercing blue eyes under a mass of raven hair, fixed on the player seated opposite him. His expression was hard and he gave away nothing. A voluptuous blonde was draped over his shoulder, batting her eye lashes and tossing her curly hair as much as her updo allowed.

"Miss Gilbert?" Mason's voice brought her back to the ballroom.

"Yes?"

"Are you interested in cards, Miss Gilbert?"

"No. Why do you ask?"

"I noticed your eyes lingering on the card game going on in the adjoining room."

"Oh… Well… I was merely curious. That man in there, with the blue eyes, I have not seen him before. Is he new to the city?"

"Oh, you mean Damon Salvatore? No, he is not. He is a notorious gambler. It is a career for him. He inherited a mansion somewhere in the country, but lacks the means to properly care for it. His cousin, Stefan Salvatore, the man sitting opposite him at the table, inherited the remainder of the family fortune. It is a long and rather tedious story, not to bother delicate creatures such as yourself with."

"And the woman beside him?" Elena pressed on.

"Ah… Miss Katherine Pierce. If it were not for the Salvatore fortune, she would be the greatest cause for strife between the cousins. Delightful creature, is she not?"

"You appear rather smitten yourself, Mr. Lockwood," Elena noted.

"Miss Pierce is a most charming specimen of the female population, but I much prefer your company, Miss Gilbert," he said smoothly and kissed her hand.

"Will you introduce me?" she said bluntly, surprised at her own presumptuousness.

"To Miss Pierce?"

"No. To Mr. Damon Salvatore. I wish to make his acquaintance."

"Certainly," Mason agreed, his jaw clenched. She would learn soon enough that Damon Salvatore was not an appropriate connection for a woman of her station.

The card game had just ended and the participants were heading over to the dance floor. Katherine Pierce was now clinging to a fair-haired, green-eyed man and it was not difficult to read the blue-eyed man's discontent on his handsome face. His sculpted lips quirked upwards to form a small smirk as his gaze fell on Mason.

"Mason! How have you been, old friend?" he patted Mason's shoulder heartily.

"Very well, thank you. I see you are in good spirits," Mason smiled politely. The exuberance Damon Salvatore displayed appeared to be connected with his bourbon-scented breath.

"I am, my friend. Lady Luck has shown me great mercy tonight."

"I am glad to hear it. May I introduce Miss Elena Gilbert?" Mason said in an air of propriety, stepping aside to let Elena come into full view in her pale green dress, hugging her curves in a subtle but alluring manner, her heart-shaped face framed with chocolate curls.

Damon's expression fell slightly as he took in the beauty before him, but he quickly composed himself and his handsome features settled back into what might be considered his trademark smirk.

"Miss Gilbert," he bowed and grasped her outstretched hand, kissing it in greeting.

It was the same gesture as Mason had afforded her, but as he looked up at her through dark lashes, a shiver ran down Elena's spine.

"Mr. Salvatore," she said in a soft, melodious voice, as refreshing as a cool breeze on a hot summer's day in comparison to the women who usually sought his company.

"Are you new to Atlanta, Miss Gilbert? I cannot remember seeing you before."

Mason took his leave of them and went to join some of his other friends.

"I am. Relatively. May I be so bold as to ask you to join me in the room you recently vacated?"

"Uh… certainly. Are you interested in learning how to play cards?" he asked as he escorted her into the adjoining room, permeated with leftover cigar smoke and liquor fumes.

"Are you a gambling man, Mr. Salvatore?" Elena asked brazenly.

"I have been known to take risks in favor of great gain," he replied casually, curious as to where she was going with this.

"Will you allow me to tell you my life's story, Mr. Salvatore?" Elena asked, nervousness creeping over her.

"Certainly."

After she had finished her recapitulation, Elena met his gaze fearlessly. "And that is why, when I heard of your nature and your circumstances, I requested to make your acquaintance."

"You want me to marry you?"

"You will be generously compensated, I assure you. I have no interest in finding a man to love, Mr. Salvatore. During this past year, I have had a taste of independence, and I do not wish to give it up for anything. If arranging a marriage is my only option, so be it."

"It is certainly an appealing offer, Miss Gilbert. But before we finalize our plans, there is one obstacle to overcome."

"Please, tell me what it is and we can discuss the matter."

"Could I call on you tomorrow? Are you staying in the city?"

"I am, and you may. I am renting a house on 1864 Honoria Street. My handmaiden will prepare tea for us at 10 o'clock, if that is agreeable to you."

"Until tomorrow, then, Miss Elena," he inclined his head and Elena picked up her skirts and exited the room.