*This is the first story I have posted at this site and my first attempt at Vampire Diaries fanfic, cross your fingers it goes well. The story will be totally AU, set roughly between 1868 and 1870.*

~Chapter 1~

Mystic Falls, Virginia was the very last place he wanted to be. Ever.

That was saying a lot, as Damon Salvatore had made enemies in almost every state, county, or territory where he'd been. Aside from collecting a good number of the country's most notorious criminals, he'd also worked for both the North and the South during the Civil War; something many people didn't appreciate. As far as he was concerned, money was money. He did what he had to do to get by.

He'd left Mystic Falls five years ago at the age of nineteen, swearing a personal oath to never return. Yet here he was, riding at a break-neck pace to get to the town on which he had angrily turned his back. He was pushing his mount harder than was wise but the sooner he collected Grayson Gilbert and returned him to Texas, the quicker he'd earn his bounty and finally buy himself a nice parcel of land in some remote section of the Midwest.

When he came across the information that a man he knew from his past was wanted in Texas for murder, his first reaction had been disbelief. What were the odds that Mystic Falls would still find a way to haunt him when he was so far away? He'd turned to walk away from the Wanted poster intending to ignore it, but his subconscious had noted the reward and his feet didn't quite comply. A sum that large meant he could disappear where no one knew his name. He could live a peaceful life in a home he'd build on land that was his and his alone.

While there were others searching for Grayson Gilbert, Damon had a distinct advantage. The Wanted poster had a sketch of Gilbert, but no information other than a first name and that he had passed through El Paso on business, leaving carnage in his wake. Apparently when his request for new investors hadn't panned out, Gilbert killed those who turned him down and took whatever money they had on their person or in their homes.

The Grayson Gilbert Damon had known years ago was judgmental and haughty – maybe even a little mysterious – but Damon had never pegged the man as a murderer. A lot could change in five years though; even Damon had to acknowledge that.

Armed with knowledge that none of his counterparts had – namely a last name, an address, and a deep-rooted disgust at having to do this in the first place – Damon set off for Mystic Falls and the townspeople he wished he never had to see again.

That had all transpired a week ago, and now he was mere hours from walking up the front steps of the Gilbert's front porch, grabbing Grayson Gilbert and then turning right around and getting the hell out of Mystic Falls.

Again.

"You don't have to marry either of them, Elena."

With a weary sigh Elena Gilbert turned away from the mirror where she'd been dressing her hair to answer her aunt Jenna. "Yes I do, and you know that."

Worrying her hands in frustration, the slightly older woman paced. "There has to be another way. Alaric Saltzman has been quite attentive lately. I am sure if I were to give him any indication that I return his interest, I could get him to propose."

With an affectionate smile Elena responded to the doting woman who was more like a big sister or friend, "While I wish you would simply because I want to see you happy and I truly believe the two of you would be," she sighed, defeat entering her tone, "It wouldn't help. Alaric is a tutor; he does not make enough money to support the lot of us."

Jenna's brow furrowed, the feeling of helplessness making her utter the words she had tried so hard to avoid since they last heard from Grayson a year ago. "I just don't understand why your father did this. Why would he abandon all of us… especially with all of this debt? I know Jeremy is eighteen and a man by definition, but he has not a dime to his name and no mentor to guide him. He's stuck playing escort to his sister and aunt and has nothing to offer a woman of his own."

Stepping closer to the niece she'd watched age much too quickly since moving in with the family when their mother – and her sister – had died three years ago, Jenna finished in a whisper as she lightly stroked Elena's hair. "And there is you. You were always his favorite; his little girl. How could he leave us all to swing in the wind?"

Trying to remain positive – a trait she'd inherited from her mother – Elena ignored the stab of pain at her aunt's words and painted a smile on her face feigning lightness. For a reason she never understood, she'd always tried to make others feel better, even if she didn't feel that way herself. "Who knows Jenna, maybe he'll walk through that door tomorrow and all of this will be for nothing?" She swallowed before adding, "If not, then Stefan Salvatore or Tyler Lockwood are both wonderful alternatives to the financial difficulties we're having."

Despite her niece's effort, Jenna could tell that marrying either man to ensure her family's financial security was not the life Elena had planned for herself. She knew, however, that saying so would not ease Elena in any way. Deciding the subject had been discussed enough for the evening, Jenna began busying herself by straightening Elena's dress over her petticoats.

Ironically Elena had always found Stefan Salvatore attractive; she had a crush on him when she was still in the schoolroom. The man was everything Elena and her aunt would have wanted for her before, but having to marry someone took some of the romance out of what should be a glorious occasion. Then there was Tyler Lockwood. He had even more money than the independently wealthy Stefan Salvatore, and he could guarantee Jeremy a place in business as his family owned a thriving shipping company.

Both men could provide for her family's necessities and then some; which was why Elena was primping herself for this evening's Founder's Ball. She was expected to be there as the Gilberts had been one of Mystic Falls' founding families and events like these were mandatory for her, but she was also going to spend more time with Stefan Salvatore and Tyler Lockwood. It was the only way she knew to save her family.

As she mindlessly put the finishing touches on her appearance, she couldn't help but think of the two men. Realistically, she couldn't lose; both had hinted that they would be more than willing to help her family should their future bring a union and neither of them was anything but kind to her. Sure there was talk in town of some of their less savory attributes, but realistically, who didn't have a shadow on his reputation?

In Tyler's case he was rumored to occasionally drink too much and have a bit of a temper. Stefan didn't appear to have any secrets of his own, but his family held some. His older brother Damon – who Elena vaguely remembered meeting when she was younger – was rumored to have killed their guardian, an uncle, before leaving town five years ago.

The older Salvatore had been tried and found not guilty, but the townspeople had been less than convinced of his innocence and let it be known. He reportedly left town shortly thereafter, signing over his uncle's substantial inheritance to his brother Stefan and turning his back on all things Mystic Falls. It was also rumored that he made his living as a bounty hunter and worked for both the North and South during the war. Whether any of it was true wasn't overly concerning to Elena, as the one bit of gossip she did believe was how vastly different the Salvatore brothers were from each other.

While either Stefan or Tyler would be a more than suitable match, Elena couldn't help but feel resentful that her marriage had become a financial necessity. Granted, money or social status was often the reason for marriage anyway; but she had hoped to be one of the lucky few who actually married for love.

Maybe she'd be fortunate enough that the genuine affection she felt for one of these men would someday become more. Maybe not, but at least her brother and aunt would have a roof over their heads.

Shaking herself from her morose thoughts, she gave herself one last cursory look in the mirror. When her eyes met the sympathetic reflection of her aunt, she did her best to smile brightly. She hated seeing that resigned sadness in her family's eyes. Their lives were going to change for the better, by God, and she'd do whatever it took to make that happen.

With a firm nod, she turned away from the mirror. Their luck was going to change. Starting tonight.