This story will be first set in Season 1 starting at the episode A Few Good Men and will continue all the way through to season 3. Not sure what the pairing will be but I'm pretty sure it will be Damon/OC leading upto an eventual Damon/OC/Klaus.


How do you continue to live a life that's not worth living? When there is no one worth living your life with? Knowing your life has no purpose? You give up. That's what I did. I gave up.

But just as I decided to leave it all behind, I met the one man who changed me. Changed my life, changed who I was and gave me a new life. A life as a vampire. I was free.

I have spent the last 430 years travelling from town to town, city to city. I had travelled every continent and encountered so many people. I found that I could never stay in one place for too long, though I was never concerned about outstaying my welcome, I always felt the need to move on to somewhere new. I hardly visited the same place twice but no matter how hard I tried to escape it, I always felt myself being dragged back to that one place that I found so hard to leave all those years ago. Which is why I now find myself returning to Mystic Falls.

I pulled up in my white Audi R8 V10 and stepped out of the car. Looking around I could see that the town hadn't changed that much since that last time I was here which if I remember correctly was probably about 30 years ago. As I said, there was something that just constantly pulled me back here. I came and went, staying unnoticed, but this time I felt the need for change. I was going to stay for a while and make myself known to some old faces I hadn't seen in a while. I grabbed my leather jacket off the passenger seat and pulled it on before walking down the street to a somewhat familiar sight, the Mystic Grill.

I had seen numerous advertisements on my way into town to know there was some sort of event on today, I mean, really, when is there not some kind of event happening in this town? They will use any excuse to hold some kind of gathering. But this particular event caught my eye. A fundraiser at the Grill in order to raise funds for some annual founder's day celebration thing. Surprise surprise. But the idea of it being a bachelor raffle made things particularly interesting.

Stepping through the doors I was greeted by a mass of people. To be honest, I was surprised to see that it was not in fact full of desperate single cougars and there were in fact young people here. I found myself automatically walking to the bar, the sound of my heels following me gaining the attention of some unwelcoming eyes at the sight of a new face.

'Double whisky on the rocks please' I said to the bartender whilst sliding onto a bar stool.

'Here you go, hey wait, are you new around here?' Glancing over at him, I grabbed my drink and casually replied.

'Thanks, and uh...yeah, kinda' Turning back around to face the stage in the bar I took a sip of my whisky, feeling the pleasant burning instantly.

'Yeah, you don't sound like you're from around here, if you want it can show you around and maybe we could you know, go out for a few drinks later?' Sighing I turned back around to face him leaning on the bar. Why can't people let me enjoy my drink peacefully?

'Look' I started, catching his eyes and making them dilate 'How about you just shut up, carry on doing your job and get me another drink.' He blinked then stepped back and smiled.

'Let me go get that drink for ya, it's on the house.' Before walking away. Wow, it seems the town doesn't change and neither do the people, they still love to talk. I downed the remains of the drink before grabbing the new one out of his hands and taking a few steps from the bar.

My attentioned was directed to a small platform where some perky woman in a blue dress started to address everyone in the Grill.

'Tickets for the raffle are now on sale. All proceeds benefit the annual founder's day celebration.' she announced into the microphone before stepping down to gossip with the other women scattered around. Looking around I spotted a group of teens where they were selling the raffle tickets.

I walked over to the group which consisted of a blonde guy and two girls. Standing in between the blonde girl and the guy, who I had seen walking around the Grill a few times, obviously working, I turned to him and put on my most charming smile before looking up at him.

'So, are you part of the raffle?'

He looked down at me whilst I could feel the other two girls slightly glare at me. I saw his eyes slightly widen in shock before laughing. 'Me? Nah, I just work here.'

'See! He's already been hit on like, thirty five times. He's total cougar bait.' Blondie said to the other girl whilst pointing to the guy, completely ignoring me. Wait, how old does this kid think I am! I am 21, well, my body is 21 so I know for a fact that I defiantly do not look like one of the cougars crawling around this place.

'Impressive' the other girl said. Looking up my eyes slightly widened in shock. This was the first time I had taken a real look at her. Well wasn't this a coincidence, Katherine's doppelganger. I knew that this wasn't Katherine because I had known her for a long time. Unfortunately.

The guy next to be broke me out of my trance.

'More like embarrassing.' He shyly said glancing at the girls surrounding him before slightly glaring at the woman approaching us. I couldn't help looking at the doppelganger once again. She looked so much like her...only more, innocent.

'Elena, honey.' The woman greeted her with a hug. So, her name was Elena. I'll keep my eye on this one. I wonder if she knows anything about Katherine or was she just living in a fantasy where she knew nothing of the real horrors of this world.

'Just kidding. Calm down. He found his rebound girl. Oh, here you go sweetheart. However many that'll buy' The woman said before handing the blonde some money. 'I just hope I don't get bachelor three, I dated him in high school. Not impressive...in any way. Very exciting' Giving a sarcastic smirk before taking her tickets and walking away. The teens' gaze following her.

Well that was awkward.

Raising my eyebrows I cleared my throat. 'Well, I guess I'll take two please.' Holding out some cash.

'Sure.' Blondie replied, letting out was seemed to be a sigh of relief. Instantly perking up and handing me my tickets. 'Good luck!' She called before I walked away.

I leaned against one of the podiums at the side of the room and saw one of the people I had expected to see, only a little more drunk. I smirked and raised my forgotten drink to my lips. I decided to keep my distance for now, but being a vampire had it's advantages, I didn't have to move closer to hear their conversation.

'I've got the big date planned. It's a romantic dinner, secluded spot somewhere...woodsy.' I silently laughed; there was that charm that I've missed so much. It's one of the things that made him Damon. And clearly it was working as the woman who seemed to be running the event looked at him impressed and clearly flirted back with him. Now that I looked clearly at her, I knew who she was. Carol Lockwood. She hadn't changed much, except well, she had aged. Obviously.

'You're making me think that I should buy a ticket.' Wait, so she holds a fundraiser but doesn't even contribute towards giving some funding? Real smooth Carol.

'Well, you are in charge. You could always rig it.' I was just about to step forward but refrained when Damon glanced up and following his gaze I saw the Sheriff. 'Pardon me' He said before walking off to go and speak with the Sheriff. I suppose I'll leave him to it, it's better if I don't get involved with council members on my first day back.

The area surrounding me was getting more and more busy by the minute as all the women flocked around the stage as Carol began to introduce the bachelors. I glanced down at my drink and swirled the contents around the glass clearly bored before I realised I should probably be paying attention. If I won a date with one of the bachelors, I wouldn't need to know what they did for a living or how old they were, I would just be quite happy to have a good feed or two.

'And what do you do Bachelor number three?' Carol smiled with her well practiced hosting skills.

'Yeah, I'm a plumber.' What a catch.

'Well, isn't that wonderful? We could always use more plumbers.' She said emitting laughter from the female audience. Seems like Carol is the same old snob she has always been. 'Moving on, number four...Alaric Saltzman. Wow. Well that's quite a mouthful. What do you do Alaric?'

'I'm a teacher at Mystic Falls High.' This guy wasn't too bad actually, but you could tell he didn't want to be here.

'Oh, beauty and brains ladies, this one's a keeper. What do you teach?' Carol asked encouraging him to continue.

'History.'

'Oh, well, give us a fun fact about Mystic Falls, something crazy.' I saw Damon move out of the corner of my eye, he was clearly up to something and Damon being who he is, was probably about to make a dick out of himself.

'Oh well...uhh' Alaric hesitated.

'He's probably just saving the best stories for his date.' Carol covered for him. 'And last but not least, Damon Salvatore. We don't have much on you.'

'Well, I'm tough to fit on a card.' I shook my head, same old Damon.

'Do you have any hobbies? Like to travel?'

'Oh yeah. L.A, New York.' He started, making a show of what he said, 'Couple of years ago, I was in North Carolina, near the Duke campus. Actually I think...I think Alaric went to school there, didn't you Rick?'
I could tell Damon had hit a nerve. 'Yeah, 'cause I...I know your wife did. I had a drink with her once. She was, she was a great girl. I ever tell you that? 'Cause she was...she was...delicious.'

Yep, Alaric looked pissed. I felt for the guy, it seemed like he was a truly nice guy.

There was a short break before the winners were announced and I saw Damon leave the stage, probably to get another drink. Once again, I was stopped from approaching him as I saw a very upset Elena stop in front of him.

'Did you enjoy that? Rubbing it into Alaric Saltzman?' she cried out to him. He genuinely did looked confused.

'What?'

'Just as I was starting to think there was redeemable about you.' She looked as though she was going to break any second. I sighed and stepped closer but I decided to keep my distance as I saw Stefan appear behind Damon.

'Elena.'

Damon's confusion was confirmed as he asked the two 'Am I missing something here?'

That set Elena off big time.

'Did I forget to mention earlier, when we were talking about my birth mother, the one that gave me up. Her name was Isobel. Go ahead. Reminisce about how you killed her.' She finished as she stormed past him with Stefan following her.

I downed the rest of my drink and finally decided to make my presence known to Damon. His eyes were still locked to where Elena and Stefan had just left, his eyebrows burrowed together with a frown on his face. I stood beside him undetected.

'Well looks like someone's had an eventful night.' I smirked at him. Damon sighed and didn't bother looking at me.

'Esmé.'