A/N: Hey guys! After months of reading fanfiction, I've decided to give it a try myself. This is my first story so of course, I'm open to all the suggestions I can get for improvement. This idea just sort of popped into my head and I'm curious as to where it will take me. Guess there's only one way to find out for sure!

Disclaimer: I do not own any part of TVD or its characters.

Beep! Beep! Beep! Be—

Elena Gilbert slammed her fist down on the alarm clock and reluctantly opened her eyes, only to see a flashing 7:30 glaring back at her. Dammit, she muttered as she rose groggily from the bed to her feet. Elena dragged herself to her third-floor apartment window, greeted by the already apparent bustling sounds of an average morning in downtown Richmond, Virginia. She scowled when she noticed a man in a fine Armani business suit rush towards a taxi, grimaced as a woman fiddled with her palm pilot, and clenched her fists as the preppy schoolchildren walked as if on a death march to their boring classes. Elena backed away from her window in an instant and turned to look back at her small dusty apartment, complete with a queen-sized bed, miniscule dresser with one of the tiniest mirrors she had ever seen, and the dreaded alarm clock that sat on a little desk situated in the corner of the room; all she could afford based on her salary these days was this junkyard she called home.

The old Elena Gilbert would never have accepted this type of lifestyle. The reason she was in this situation to begin with was because of her family back in Mystic Falls. After coming home from her best friend Bonnie Bennett's house, Elena found an all-too-surreal sight. Grayson and Miranda Gilbert, as well as her brother, Jeremy, were uncomfortably seated on the couch with their hands and feet bound together. Elena made a move to run right at them until she heard the click of a gun behind her. The terrorist ordered her not to move as he made his way around her towards the rest of the family. Without further warning, he shot each of them and turned towards her, pointing his gun. Elena felt hot tears of rage and sadness fall from her face as a cold and empty feeling surged through her body. She closed her eyes and waited for her impending doom for what seemed like an eternity, but after a few moments she realized that nothing was going to happen. When she opened them again, the only sign of the murderer was his gun left on the coffee table. Elena immediately dialed 911 and within minutes Sheriff Liz Forbes arrived on her doorstep. Apparently, having everyone else in her family murdered with a gun left right by the bodies and no other person in sight did not look good for Elena. The way it seemed to Sheriff Forbes, the murders were carried out too amateur-like for a serial killer to do it; much to her horror, this put Elena as the prime suspect. Before the sheriff could send her off in handcuffs, Elena asked if she could at least spend a few moments alone to reminisce about her family. Sheriff Forbes reluctantly allowed her to do so given this might be her last chance of freedom. Elena shuffled upstairs to her bedroom and locked the door, quickly heading for the window. Elena fled her home that night, no longer feeling safe in the little town of Mystic Falls, and vowed to find and avenge the murder of her family. She was forced to live on the streets of Richmond, a city 100 miles away, going so far as to steal from the local grocery store or pickpocket a man for a few spare dollars.

On the eve of her 17th birthday, Elena found a man that seemed to make everything bad just disappear, even if for a moment; Mason Lockwood was charming, or so it seemed. At first, Mason catered to Elena's every demand and wish, but looking back now she could see that it was all just a ploy to get her to trust him and join forces with him. Elena could still feel the initial shock she held within her when Mason blatantly confided in her that he did business with the Mafia and that he was short an assassin and needed someone to do his dirty work; he had been watching Elena for a time and thought she might have great potential one day in the Mafia wars. On top of all this, he promised good pay. Elena hesitantly agreed to this twisted arrangement since she had become so desperate over the past few months for at least a little bit of good fortune and presumed that she had nothing else to lose in the world; she even considered the fact that maybe working with the Mafia might lead her to the man who murdered her family so that she could avenge their deaths. After warming up to Mason and his troupe, she told her fellow assassins her tragic back story. Mason agreed that the Mafia would help her in her quest to destroy the man that took away her security in life.

Elena stepped back into the present day and went towards her bathroom to take a quick shower before she headed out to meet Mason. He was the type of guy known to only do things for a person if an equal favor was returned; Elena figured that in order to keep him around, only one of two people she still had a real connection with nowadays, she owed him whatever services he deemed necessary. She took one glance in the mirror at her appearance, her waist-length chestnut brown hair brought up into a ponytail. She hurriedly rummaged through the contents of her dresser, dissatisfied with what little options she had to choose from, but decided upon a pair of nice-fitting jeans and a loose white t-shirt before leaving the shabby room.

Elena made her way towards the building complex that held Mason's private affairs. From the outside, not much could be said about the makeshift of the building other than it appeared to be rundown and out of use; the same could be said for the inside as well. As soon as Elena was through the front doors, a pair of strong arms grabbed her from behind. Elena reached up to grab her opponent's head before jerking it forward with all of her might. She heard a loud pop and the arms quickly let go of her.

"Ow! What the hell did you do that for? You know it's only me, Elena," a disheveled man with short dark brown hair and a muscular body professed.

Elena immediately moved towards her supposed attacker. "Oh my gosh, I'm so sorry Tyler! I've just been really out of it this morning."

"I see that those martial arts classes have really worked some magic on you," Tyler groaned, rubbing his neck as he got to his feet. "Uncle Mason said he had an important assignment for you by the way. I think this one might actually get him off your back for awhile."

Elena stared past Tyler for a moment as he made his announcement. Tyler had recently moved to Richmond to live with his Uncle Mason after his parents had died in a terrible car accident. Tyler never had much of an appreciation for his uncle after he had been exposed to Mason's "business", yet he was the only person Tyler had left. Elena and Tyler found Mason's antics to be over-the-top and, more often than not, way out of line. However, both of them felt as though this was their revenge for getting back at the world for taking away the people that mattered most to them. Elena shared a lot of things with Tyler and vice versa; he was like the brother she once had. Elena felt as though she could sympathize with Tyler since she found herself arguably in the same situation.

Elena nodded herself out of her reverie and looked towards Tyler. "You mean I'd be done with all of his little errands?" she asked hopefully. Although Mason had kept true to his word about her salary, Elena quickly grew tired of his constant nagging at her to take up her duties as one of his best assassins; however, she tolerated all of this because the Mafia had become a sort of second family to her.

Tyler shook his head in agreement. "At least for a while anyways. I'm pretty sure he found a client with an incredible amount of money to offer this time."

Elena glanced towards the door opposite where she now stood. "Guess I better go see what all the mystery's about then."

"I think Uncle Mason's still with his client. Might do some good to get to know him as well; who knows, it could make this little adventure easier for you."

"Misadventure, Tyler."

Elena walked away from a passive Tyler and closer towards her fate. She paused slightly before knocking on the door as she reconsidered Tyler's words, hoping he was right. She tapped lightly on the door, followed by a gruff 'Come in'.

Once Elena stepped into the room she was met with a pair of magnificent green eyes. She whole-heartedly took in the man before her, his hair the perfect bronze color, his strict jaw-line, and his lean but firm body underneath a very expensive suit. Elena didn't realize she was ogling the man until Mason cleared his throat and began to speak.

"Elena, I would like you to make your acquaintances with Mr. Stefan Salvatore," he said. Stefan smiled politely at her, although Elena could tell something was off from his grin. "He has come here and offered a very good deal for us. Stefan, Elena Gilbert is one of our finest assassins. I'm sure she will not disappoint in getting rid of your brother for you."

Elena felt a slight twinge of regret as Stefan continued to smile at her. The pain of losing her own brother came rushing back to her thoughts; how he could betray his own brother like that was beyond her. However, this was the business and life she chose to go into, and she absolutely had to accept the arrangements at all costs. "That's right, Mr. Salvatore. Mason taught me everything I know. I am quite capable of handling myself in the toughest of situations."

"That's good to hear, Miss Gilbert," replied the sly voice of Stefan. "I'm sure you are a little curious as to why I want my brother out of the picture."

"Maybe just a little bit."

"Ever since we were children, my father, Giuseppe, has always taken a liking to my brother, Damon, giving him everything he wanted while I'm left out of luck; he even offered Damon the CEO position of our law firm until my father realized that he had another son to think of as well. When my father fell ill, he made us Co-CEO's of his business." Stefan paused for a moment before going on with an exasperated look plastered onto his face. "And then the love of my life, Katherine, found me and I thought 'finally I have something that is so much more than what he could have'. She meant everything to me and I thought it was all the same with her, so before long I found myself engaged to the most beautiful woman I had ever laid eyes on. My father saw her as a trophy wife for me and automatically offered her a job as secretary for the firm; she had a way of making everyone around her fall under her captivating spell. It was only until a week before our wedding date that I overheard Katherine mention to Damon in his office how their plan to get rid of me and my father in the law firm would be set into motion a month after the wedding so that I could 'earn her trust first'."

Elena noticed Stefan had abruptly stopped his story. "I don't seem to understand, Mr. Salvatore," she inquired, "but why not just go after Katherine instead of Damon?"

"Because Damon was in love with Katherine as well," Stefan snapped. "And the bitch fell for him as well. Damon is nothing but a womanizer that always takes away the things I love most. He doesn't deserve to be my Co-CEO, let alone my own brother."

"And you want me to kill Damon so that he's out of the picture and earn all the rights to the share in the law firm?" Elena questioned.

"Yes and no. I want you to kill him for taking away everything in my life," Stefan replied.

"You don't know what that's like," Elena mumbled.

"Sorry?"

"Nothing, Mr. Salvatore. When do you need me to start?"

"I was thinking.." Stefan started.

"Now."

Both Elena and Stefan looked towards Mason with shocked expressions. "I can't waste anymore time with this while you too ponder over when to begin. I do have a business to run here after all," Mason noted.

Elena glanced up at Stefan with her wide brown eyes, while Stefan looked down at her and smiled devilishly. "I suppose you're going to meet Damon in a few hours, Miss Gilbert."

"Let's just get this over with," Elena replied. She followed Stefan as he headed out the door.

She felt as though karma was laughing at her for doing the same thing that she swore to vow revenge on; hell, she'd probably end up in the same position as the person who murdered her family, wherever he was. Whoever this Stefan Salvatore was and whatever problems he seemed to have with his brother, he better have paid an enormous sum for this expedition; after all, it was just good business.