A/N: This is my first attempt at an all human story and I will admit that I am very nervous. Not being able to rely on the canon of the show has proven to be a challenge, but I am hoping I put something together worth reading. My goal is to update this story weekly (most likely on the weekends).

Summary: Each of us has a past that shapes and defines us. Some pasts are filled with pain and heartache. Can Damon and Elena overcome their pasts to allow themselves a chance at happiness? Or will things from their past resurface to destroy their future?

Disclaimer: I do not own the Vampire Diaries stories or characters.

Happy Reading!

Chapter 1

"You're leaving" the blonde whined as she watched the toned muscular backside of a man walk around her apartment looking for clothes.

"Andie" his velvety voice chastised. "I don't do sleepovers. You know that." His ocean blue eyes were full of mirth as he flashed Andie his patented smirk over this shoulder as he pulled on his jeans. "Plus the international markets open soon. Need to go make some money." He saw her face fall in disappointment.

"Anyway, aren't you filling in as anchor for Good Morning New York today?" He stood up, jeans sitting low on his hips, and continued to hunt around for the rest of his clothes that were hastily stripped off as they did naughty things to each on every service they touched in her apartment.

Andie sighed sitting in the middle of her bed clutching the sheet to her chest. "That's all you do is fuck and make money. Isn't that a shallow existence, Damon?"

"I also like to drink" Damon wiggled his eyebrows as he slid his arms into his black shirt and buttoned it over his chiseled chest. Damon sat down on the edge of the bed to pull on his black boots that were ever present on his feet when he wasn't in the office. He would like to wear them every day, but dressing casually as a stockbroker was frowned upon.

Andie reached over and grabbed a tabloid from her bedside table throwing it on the bed next to Damon. He looked over at the cover with his picture standing next to a tall red head and the blaring headline 'Damon Salvatore, Playboy Stockbroker.'

"Don't you want more? Something more than that?" She pointed at the tabloid. She inched closer to Damon reaching out to touch his shoulder. "I could be something more for you. Marriage. Family. I care about you." Damon glanced over his shoulder and could see the desperation in her eyes.

Damon picked up the magazine his back to Andie and glared at the picture of his smirking face fighting the growing anger inside of him. He turned back to Andie his face a mask of indifference and threw the magazine into her lap. "I'm an asshole, Andie. You don't want me." Damon stuffed his wallet into his back pocket and looked around for his cell phone locating it on the bedside table.

"But you'd be my asshole" Andie purred crawling across the bed towards him.

Picking up the phone, he scowled as he saw multiple missed calls and texts. He stuffed the phone into his back pocket. He leaned over putting his hands onto the bed his lips inches from Andie's. She smiled and seemed to be waiting for him to lean in and kiss her.

"If my face wasn't on every God damn tabloid and I worked some mundane job making a middle class wage, would you still want me and the future you think you can give me? Would you still 'care' about me as you put it?" Damon's eyes narrowed and his chiseled jaw clenched.

Andie scooted back on the bed shrinking under his gaze. Her mouth opened and closed a few times like a fish gasping for air before her gaze dropped down. Guilt and shame was evident on her beautiful face.

"Exactly." Damon grabbed his leather jacket and walked out the door without a second glance.

Every woman thinks they know what I want and can provide me some version of domesticated bliss, Damon thought to himself. All women really want is their own picture in the tabloids and a cut of my money. Damon allowed his thoughts to continue to ramble. Drink, fuck, go home, lather and repeat. That is my present and future bliss. Damon flagged down a cab and slunk down in the seat as the cab maneuvered the 3 am barren streets of New York City to his condo on 5th Avenue. Pulling out his phone he listened to the missed voicemails and read the texts. Just as he was about to put his phone away it started to ring. Looking at the phone he scowled seeing the number was the same as the missed calls.

"You have left me twenty voicemails and countless texts over the past few weeks. Take the hint. I want nothing to do with you" Damon growled.

"I don't like being ignored" the voice whined.

"Get used to it." Damon hung up the phone as the cab stopped in front of his building and he hopped out.

Damon nodded to the doorman as he entered ignoring the little smirk on the doorman's face acknowledging Damon's late night activities. Entering his home he looked around at the modern design and sleek lines of the impeccably designed apartment and again the hole inside of him entrenched itself further into his soul. Damon headed into the kitchen and poured himself a shot of whiskey before heading off to bed to catch an hour or two of sleep before he had to be up ready to head into the office.

Damon worked for one of the most prestigious brokerage firms on Wall Street and quickly climbed the ranks in the four years he had been with the company. At twenty-six he was already in a corner office with a view that had Manhattan at his feet. Damon managed to get through his day making his firm copious amounts of money. Looking up at the clock he saw it was almost nine at night. He unbuttoned the cuffs of his blue designer shirt and rolled the sleeves up and rubbed his tired eyes.

"OMG its Damon Salvatore, can I have your autograph?" Alaric Saltzman mocked, hands waving in the air, as he walked into Damon's office and plopped down in the chair across the large mahogany desk as he loosened his own tie. Alaric threw a magazine he had been holding on the desk with a sly smile.

Damon looked down to see his ocean blue eyes and trademark smirk on the cover of GQ magazine as one of the country's most eligible bachelors. "What can I say? I am God' gift." Damon put his Armani clad feet on his desk and stretched out his arms. He ran his hands through his raven locks before linking his arms behind his head wiggling his eyebrows at his best friend.

"You're a dick. First the New York Post declares you one of New York City's most eligible bachelors now GQ declares the same thing!" Alaric just shook his head.

"Look at me. I'm hot, I'm rich, I'm the youngest and most successful stock broker in Wall Street history…what more could a woman want." Damon leaned back further in his chair.

"You never stay with any woman longer than five minutes, you're ego is the size of the state of New York, and you're a workaholic…." Alaric quirked an eyebrow at this friend.

"I think you need to buy me and my GQ declared hotness a drink." Damon got to his feet and grabbed his coat circling the desk and slapping Alaric on the back.

Alaric and Damon hopped into a cab and headed to Taboo, one of a handful of bars and nightclubs that Damon was a primary investor in. Of all Damon's bars, it was the most high end and all of New York's elite as well as elite wannabes frequented the club. The two exited the cab and paparazzi started snapping pictures as they bypassed the long line and headed straight for the bouncer.

"How are you doing Ben?" Damon asked slapping the bouncer on the shoulder.

"Great Mr. Salvatore, thanks for asking. Have a good evening." Ben held the door open, the loud base of the music spilling out the door as Alaric and Damon crossed the threshold.

Alaric and Damon wound their way through the throngs of people. Women's eyes were practically having sex with Damon as he passed through the crowd. Damon stopped at the bar to check in with the bartender.

"That's Damon Salvatore, go talk to him. You look hot tonight." Damon glanced over his shoulder and saw two blondes whispering loudly to each other. They were obviously too drunk to realize he could hear their entire conversation.

"He's loaded; talk about one hot sugar-daddy."

Damon face clouded in anger before he quickly put a smirk on his face. As he made his way to the VIP area with Alaric he purposely walked between the two blondes. "This sugar daddy wouldn't fuck either of you if his life depended on it." Damon said lightly as he brushed passed them without a second glance.

Once they entered the VIP area a waitress was at their side in minutes. "What will be this evening Mr. Salvatore?" The redhead asked reaching out to touch Damon's shoulder and giving him her brightest smile.

Damon flashed a grin back before dropping his eyes to her nametag pinned strategically on her chest so he could stare at her breasts unabashedly. "Well, Callie, a bottle of bourbon for me and the professor over here." The waitress returned pouring two glasses of bourbon and leaving the bottle on the table between them winking at Damon as she walked away.

"To the good life" Damon raised his glass and Alaric clinked his glass against Damon's before downing the amber liquid in one gulp. Damon stared into his glass for a second and with a sigh downed his own.

"So who was last night's conquest. Work or pleasure?" Alaric grimaced as he asked the question.

"Pleasure…Andie Starr" Damon had a chesire cat grin on his face.

"The news lady?" Alaric's eyes shot up in surprise.

"The one and only." Damon grabbed the bottle of bourbon and refilled each of their glasses.

The two sat watching the dancing bodies from the secluded booth and continued to drink. Alaric pulled out his phone and Damon saw Alaric's face light up.

"I have to go make a phone call. I'll be back." Alaric jumped up and walked through the crowd. Damon watched Alaric go find a quiet spot to make his call, assuming it was to his girlfriend by the look on his face. Damon rested his head back against the cushioned chair he was sitting in and closed his eyes. A few minutes later her heard someone sit next to him and a hand grazed his thigh. Bolting upright at the contact, Damon turned to the chair that had been previously occupied by Alaric.

Damon's jaw dropped open slightly at the woman that sat before him. She was dressed in a tight black dress that hit above mid-thigh with her breasts spilling out the corseted top. Her long chestnut hair hung in ringlets around her shoulder and large brown doe eyes held a look of lust and her body language portrayed the carnal desire that was just below the surface.

"Hello lover" she purred stroking her hand up his thigh again.

Damon looked at the woman that once held his heart before she crushed it between her finely manicured nails. "Katherine" Damon said in an acerbic tone his eyes narrowing at his ex.

"I told you I want to nothing to do you with. Never want to see you, talk to you or think about you. Leave!" Damon barked.

"Come on Damon. I've been gone a long time. Let's forget the past and just try and be civil." Katherine crossed her legs and leaned in closer to Damon overwhelming him with the scent of her Chanel NO 5 perfume.

"Fine. I can be civil. Katherine Pierce. The wicked bitch of the west. What brings you back to New York…..marrying some old geezer worth millions in hopes he'll leave you his fortune?" Damon snarked.

Katherine narrowed her eyes slightly, but put a wide smile on her face shifting slightly in her seat. Damon couldn't help but drop his gaze to her chest as she had strategicly positioned herself so he could see down her dress.

"Oh, I recently moved back from LA. I saw you sitting over here and thought it would be nice to catch-up with an old friend." Katherine reached for the bottle of bourbon he and Alaric had been drinking from earlier and filled Damon's glass that was sitting on the table.

Katherine took a sip from the glass before handing it to Damon. "I've missed you Damon." Katherine leaned in even closer to Damon and he sat perfectly still. Her lips curled into a smile and stopped as if waiting for Damon to lean the rest of the way in to kiss her. His gaze never wavering he reached up a foot and kicked the base her chair to pushing her away from him.

"I know my sexual prowess ruined you for all other men, but it's been four years Katherine. You obviously didn't miss me that much. Why are you really here?" Damon sat up straighter holding his drink it front of him as if a shield to protect himself from whatever web of lies Katherine was trying to pull him into.

"I have thought about you every day for the past four years. I'm back for us to be together again. What we had was something spectacular. We were good together Damon. We will be good together again." Katherine looked up at him through her fake eyelashes.

Damon looked at her his eyes full of anger and fury. "No, you don't get to waltz back into my life after four years." Damon jumped out of his chair and stepped back to put some distance between himself and Katherine.

Katherine stood up and stepped in front him. She fisted her hands in his shirt and pulled him into a searing kiss. She pulled back before he came to his sense enough to push her away. "You know we are meant to be together Damon. You haven't had a serious relationship since me. Once you remember how good we were together you'll never want to let me go." Katherine released his shirt running a hand down his jaw with her manicured finger before swaying her hips as she exited the VIP lounge.

"Where the hell happened to you?" Alaric asked as walked up next to Damon a few minutes later. Damon was still standing breathing heavy and Alaric could see the pain written all over his friend's face.

"Katherine happened." Damon dropped into his seat.

"Katherine? As in Katherine Pierce? As in your ex-girlfriend, er, fiancé? She just showed up, what has it been, four years?" Alaric sputtered out his question as his eyes scanned around them.

"She left." Damon crossed his arms across his chest and he saw Alaric breathe out and his body seemed to relax.

"She's been calling and texting me the last couple of weeks. I even saw her at the Starbucks near my condo a couple of times as well as at a charity event or two. Always managed to avoid talking to her though. She called last night and I told her to go to hell. Guess it encouraged her to pay me a little visit." Damon shook his head.

Alaric eyed his friend cautiously. He knew Katherine was a touchy subject and Damon's temper was legendary. He didn't want to send him off the deep end to do something stupid, adding to Damon's long list of stupid stunts he has done in Katherine's name.

"Please tell me you're not thinking of getting back together or having angry revenge sex with her" Alaric groaned.

Alaric refilled both of their glasses and each down their drink in one gulp.

"Not to worry Ricky, but I will go have angry sex with someone else to forget her." Damon suddenly jumped up. Damon headed out without a good-bye to his friend. Alaric just stared having a bad feeling that things would be rough for Damon going forward with Katherine back in town and pursuing him.

Damon weaved his way through the crowd ignoring the looks most of the women were giving him. He needed to fuck someone and he needed to fuck someone now, without having to explain it's just for one night. He searched the crowd and he spotted the perfect candidate leaning up against the bar. Sauntering over the bar he grabbed the girls hand and started pulling out of the bar.

"Damon" the girl squealed as they reached the street and he pulled her into a passionate kiss.

"You're coming home with me Jessica" Damon said breathlessly as they headed for a cab. He gave the cab driver the address of the apartment he kept in the financial district, his official hook-up bachelor pad and they headed out into the night.

"Make me forget the things I secretly wanted more than anything." Damon pulled her into his lap.

"That works for me" Jessica ran her hands through his hair. "You can fuck away whatever woman you are running from and I can get my name in the tabloids. I'm up for a part in a movie and getting my name out there may help get me the role."

"Win-win" Damon growled pulling her into an anger fueled kiss. He can't complain about her using him as he was using her to forget the pain of Katherine. Plus at least she was honest about what she wanted from him unlike most women that used him as their personal sex toy to get free publicity since he is common tabloid fodder.

Elena leaned against the door frame of her little brother's room watching him pack clothes into an open suitcase on the bed. Her twenty year old brother was transferring to a new art school across the country.

"You almost done packing Jeremy?" Elena pushed away from the doorframe and walked over to sit down on his bed. She picked up a sweater Jeremy had haphazardly thrown next to his suitcase and folded it for him letting it sit in her lap.

"Yeah this is the last of it." Jeremy looked around taking one last survey of his room. Seeming to be satisfied he crossed over to the suitcase and reached out to take the sweater from Elena. She handed it to him with a sad smile.

"We should get your stuff downstairs. We need to leave for the airport soon." Elena stood grabbing a duffel bag that sat on the floor. Leaving her little brother's room she headed for the stairs with Jeremy following close behind with his large suitcase and backpack. Elena smiled as she passed the family pictures of happier times that littered the stairwell as she descended to the foyer.

"It's only been the two of us in this house for the past four years and before that just us and Jenna since Mom and Dad died. Now it's going to be empty." Jeremy walked through the living room and kitchen his hand ghosting objects as he passed a look of melancholy on his face.

"Look at the Gilbert kids spreading their wings to both coasts. Jeremy Gilbert taking over the west and Elena Gilbert the east" Jeremy smiled as he walked back to stand next to Elena.

"I can't believe you're going to school in California. It's so far away" Elena dropped her gaze to the floor trying to hide the sadness that must be written all over her face. Even though she would miss her brother terribly she didn't want to spoil this chance for him.

"I can't believe you are going to New York to find a publisher for your book. I can't even believe you wrote a book!" Jeremy knocked his shoulder against Elena's. "Do you think Mom and Dad would be proud of us?" Jeremy asked his eyes suddenly full of sadness and grief.

Elena pulled him quickly into a hug. "You've come so far Jeremy. You had a rough time with the drinking and the drugs after they died but you turned things around and look at you now. They would be so proud of the man you have become and so excited that you are following your dream of going to art school. Never think anything different" Elena stepped back looking Jeremy in the eyes holding onto his shoulders. "I'm proud of you too Jeremy."

"Thanks Elena." Jeremy pulled her back into a hug.

"Are you sure about this New York thing?" Jeremy asked as they separate from their hug.

"Not you too." Elena's body seemed to deflate. Everyone was worried about her taking a trip to New York. She had written a book and self published it, but was looking for a publisher to pick it up so it could be widely distributed. Her friends were all worried about her being in a big city and the potential rejection that was bound to come.

"I wanted to come to California with you, but someone wanted to do it on their own." Elena said snidely.

"You're my sister, not my mother. Why not stay here and find some nice guy and get a life? You're twenty-two, but you live the life of a spinster." Jeremy looked down at her.

"Because I can offer such a bright future to the men of Mystic Falls, Jeremy? The future I can provide them isn't what they want. It's better to just not date then to have them leave when they realize our visions for the future are not compatible." Elena shrugged. "Plus it saves me being in this house alone with the town's people staring at me with their looks of pity. I don't know about you but I'm tired of being one of those poor Gilbert kids. I'll be back before you're done with school."

"But New York tends to chew people up and spit them out. I just don't want you to get hurt Elena." Jeremy said softly.

"I know and I appreciate your concern, but someone also has to go check on Aunt Jenna. We haven't seen her in months." Elena turned toward the door Jeremy's duffel in hand ending the line of questioning and they headed out in silence to the airport.

The siblings stood at the security check-in both fighting tears. "Make sure you call Bonnie. She'll worry until she hears from you. I am actually surprised she didn't come with us." One of Elena's best friends, Bonnie Bennett had been dating Jeremy for the past three years.

"We said our good-byes last night. " Jeremy winked. Elena cringed at the meaning behind the wink.

"Make sure you call me when you land" Elena gave Jeremy one last hug before he proceeded through security.

"Yes, mom" Jeremy laughed as he rolled his eyes and walked away with a wave over his shoulder.

Elena watched until Jeremy was through security and she couldn't see him anymore. She walked out to her car and drove back to her childhood home humming to the radio reminding herself that Jeremy going to California was a good thing. He was following his dream and that was all she ever wanted for him. The house was dark when she pulled into her driveway. Entering the house the silence engulfed her. She had raised Jeremy since her parents died when she was seventeen and Jeremy was fifteen. He had been her reason to hold it together and knowing she at least had her brother with her she found the strength to handle getting through each day. Now he was gone and she was reminded that everyone that seemed to come into her life eventually seemed to leave. She was utterly alone.

A/N: As I mentioned above, this is my first attempt at an all human story so I am will be even more reliant on your feedback to make sure I am on the right track with this story. Too much detail, not enough, characters believable, etc. Plus the more reviews the faster I update!

You can follow me on twitter for story updates: wolverine_999