First of all, I would like to thanks amara97 ,my awesome beta… You rock girl… She helped me out with this chapter and I loved it.. Hope you guys also enjoy this one… Happy Reading… :)

6 months Back…

Something was going to happen.

I couldn't help but feel on edge sitting near the window holding my journal as usual in my lap. That deadly feeling creeping up my skin that something bad was going to happen was giving me the jitters. Fiddling with the pen as I tried to gather my thoughts but I could not write anything. My hands just hovered over the blank page.

I sighed and shut the journal. "Maybe it's because of lack of sleep." I muttered into the silence of my room as I stood up for a much needed shot of espresso. As I passed my parents' room, I heard my parents whispering to each other. I was about to rush by when I heard my dad.

"I don't know Isobel" That did not seem like lovemaking or sweet nothings. "We don't have enough money to pay."

Not having enough money?

My eyes went wide in surprise. I mean aren't we 'The Gilberts', one of the richest family in New York City. Sure we were not that rich when I was in high school but everything had changed during the mid senior year. Dad had married Isobel Petrova. Mama had died when I was just a freshman. After two years of mourning for Miranda, Dad had finally found love. Stepmom was a rich woman and after the union of the Gilberts and the Petrovas, Gilberts had become one of the rich families.

After high school, we moved here to New York, the city that never sleeps. So, I couldn't believe it when I heard dad tell Mom that we were having shortage of money.

"Grayson" I heard Mom's voice trying to soothe my tense father. I knew he would be pacing in their room. "They won't stop until we…"

"Elena?" I jumped as dad called me. I took a small step into the room and faced mom and dad's shocked face. "What are you doing here? It's Friday night."

I looked down as I was at loss for words. Yes, it was Friday night but I didn't have many friends or those I could say real friends. After high school, I had left behind everything and everyone, who loved Elena. When we moved here, everyone was more interested in knowing the Gilbert Perks rather than the girl behind.

"I wasn't in mood to go out" I said nervously. "I'm sorry for eavesdropping."

"You were eavesdropping?" Isobel said in disbelief.

"I heard your conversation and I have some money. I can help." I said quickly and there was a dead silence for a minute.

"Elena. Go back to your room and sleep. There is nothing to worry" Dad said in his 'go to your room young lady, this is not a place for you' voice. I nodded and made my way upstairs.

As I left, I heard Isobel say something in annoyed tone to Dad.

After Mama had died, I missed a mother's love and when Dad brought Isobel home to meet me, I had been very happy. But alas, I was not going to find a mother in her. She scolded me for almost everything, from my grades to my choice about studying literature. Following mama's dream of me going to Harvard to study English literature was almost foiled by her. 3 months when I had graduated as valedictorian with a literature degree, the two of them had not even come. But I did not care. I knew they were trying to express their disdain.

The sound of loud bang startled me, snapping me out of my thoughts. I rushed down the hallway. My heart leaped into my mouth at the sight. Dad was on his knees and a man with a broad chest pointing gun at him. My eyes then moved to see Isobel, whose arms were forced behind her back in a tight grip by another man. 3-4 men were scattered around the room with guns and the sight made my knees almost give away.

"Oh we've sweet Elena here" a black haired man who I hadn't noticed before said. He was leaning back on couch, wearing a look like he had own the house.

"Don't drag her in this" Dad pleaded and I looked at him, my eyes blurring as tears pooled into them.

"Dad what's going?" I choked out.

"I guess beautiful Elena is still clueless about everything. Right Grayson?" He smirked as he checked me from head to toe.

"William please… We're going to pay you every ounce, just give us more time" Isobel pleaded but the guy William just barked out a dangerous laugh.

"Don't fucking say that. I gave you two, a year but now I think that I've been too soft" he said and waved his hand, signalling me to come to him.

My whole body was trembling with fear. I didn't know these men and judging by their personality I was sure that they were dangerous. They were just the people Mama would rush by when we saw them lazing in the park. I had no idea why Isobel and Dad would get involved with people like them. It was clear to me that they want money, 'their money', as they called it.

"Elena Darling" William sang breaking my running thoughts. I unwillingly dragged myself towards him, tears were rolling down my cheeks from fear.

"Please… don't h..hurt me" I sobbed quietly as William ran his dirty hand on my cheeks, grinning. He clearly liked seeing me tremble like a leaf. My stomach lurched thinking what he was going to do.

"William please my daughter…" My father's words stopped in mid sentence as the guy pointing gun to him, kneeled him, making Dad groaning in agony.

I took a few rushed steps towards Dad but was pulled back roughly by William. "No.." I shook my head. "Don't hurt my dad" I screamed.

"Will…Please we can settle it down easily" Isobel said. "This doesn't have to be this way."

"It clearly has to be this way" William said as he tightened his grip on my elbow. "Boss isn't happy with you two."

There was a dead silence in the room except for my sobs that I was trying to hold back. I was shivering uncontrollably.

"He has ordered to finish this" he smirked and Isobel gasped. I started thrashing and kicking William to come out of his grasp. He was going to kill my parents, in front of my eyes.

No this couldn't be happening.

"No.. Please" Dad pleaded.

"Don't worry Gray.. I'll take care of Elena" William grinned and I started crying. I could not limit myself to sobs anymore. My stomach twisted in fear.

"Please don't hurt them. You want money, I'll do everything to pay you back. I'll do anything… Just.." I cried.

"You'll do anything?" William's sudden change of tone made me look at him. Curiosity was written all over his face.
Without giving a second thought, I nodded my head many times, determined to do anything to save my dad and stepmom.

"I wonder how boss knew you would propose that" he said amusedly and I gave him a puzzled look. "Boss wanted someone to do his dirty work and he assumed that once I'll threaten your parent's life, you'll be willing to do anything."

"You tricked me" I said with disbelief.

"No Elena… We didn't. We just invented a new way to get our money" he said. "You're going to work for us for a while Elena and I'm sure as hell, we're going to enjoy your company."

6 months later (a.k.a Present)

I missed the time when mama was around. She was calm and lovely woman who always loved and had time for me and Jeremy.

Jeremy.

Just the thought of my little brother filled my eyes with tears. I missed my brother now more than anything. He was away in California for college and I was here alone. He had no idea what's been going on here. Whenever I tried to back off from the deal, they threatened me with Jeremy's life. They had dangled a sword over me.

6 months of training, 6 months of pain and agony but most of all betrayal. I had started working for the organization 'The Five', determined to pay every penny from my parent's behalf. I had betrayed everyone in those six months. I got involved romantically with my victims, seduced them and then took what I wanted. Sometimes, I had to steal money, sometimes expensive things like diamonds and it wasn't easy at all. Luring victims wasn't my favorite thing, my life was always on stake in all that mess. But on the top of all, I never slept with them. I filled the men and women with anticipation but I never stayed long, 3-4 weeks and I was done.

Sometimes, I even regretted my decision to leave mystic falls behind. If we hadn't left our hometown, I wouldn't have been in that situation. I was suffering. The luxurious life I had once lived was what I was paying for. Isobel and dad had been working for that organization and I had never realized that. I never gave it a thought that a doctor and even a successful business woman couldn't earned what we had. I opened a cupboard and took out the photo album to relive my memories.

First picture was of me, Caroline and Bonnie. We were in tears and hugging each other. It was my farewell party that had been captured by Dad just hours before we left Mystic Falls. I smiled as the next picture was of me and Matt. He was my first boyfriend and I had loved him so much. I still feel guilty about not saying goodbye. Bonnie and Caroline found out from God knew where, when I was planning to leave without telling them. I never wanted to say goodbye to my friends and that town but eventually I did.

My eyes scanned the next photo and my breath hitched. I absentmindedly ran my fingers on the photograph. It was of me and Damon Salvatore, my classmate. We were staring at each other in the picture, Damon had that usual smirk on his face and I had that annoyed look ,I always had whenever he was around. —
Flashback…

"Come on Elena, I can't even find one reason why you're with that Donavon guy?" Damon rolled his eyes and I glared at him.

"It's my life Damon. You've no right to say in it" I turned my head away.

"But the guy is too innocent for you" he smirked. "You like it rough."

"God Damon keep your voice down" I hissed. "I don't want everyone to know that…"

"I'm the guy who took The famous Elena Gilbert's virginity away" he completed my sentence and I could feel my cheeks heating up. "Come on Elena you can never be satisfied by another guy now that you know what it feels like to be with me, underneath me" he whispered in husky sound in my ear and I shivered but quickly composed myself.

"Dick" I hissed and got up to leave but Damon held my hand and pulled me down on the chair again. "Sam one picture please…"

Sam, the guy with camera smiled and nodded. Damon wrapped his one arm loosely around my shoulder and looked at me with a smirk while I glared at him. That was when the photograph was clicked…

A knock on the door pulled me out of my thoughts.
"Come in" I said as I placed the album back in cupboard.

"Hey" Klaus, my mentor and only good friend entered my room. "So are you okay?"

I looked away and bit my lip. "Yeah.. Right wrong question." He scratched the back of his neck, nervously.

Of course I wasn't okay. I had completed my 9th target, betrayed another person and I was feeling sick. Oh how much I missed being a small town girl, without worries and care of the world.

"I'm fine" I smiled wanly at him. He was my friend and mentor. Grayson and Isobel were locked up somewhere. They won't be freed until I completed my part of the deal. So, Klaus was the only person I talked to or could rely upon. He trained me physically and mentally to defend myself if situation ever came to that.

"Elena" he held my shoulders and I knew his next words, so I completed the sentence myself.

"I know. I know. No attachments" I huffed. "Klaus I look them in the eye and betray them. What kind of person am I?"

"You're feeling guilty Elena, so you're still human" he chuckled. "Most don't give a shit about their victims but you… Your compassion is a gift Elena."

"You really know how to make me feel good" I sighed and enveloped him in a hug. "I don't know Klaus. I just.." I pulled away from him. "I don't know how much longer I can fight."

"Hey, you'll survive this. Somehow you always do" he patted my back. "Here's your next and last target" he handed me an envelope and my eyes went wide. Did I hear right?

"Last one?" I gulped and he nodded smiling.

"Oh God… I'll be free from all this. Dad and Isobel will be free. I won't have to worry about Jeremy anymore" I said squealing in happiness.

"Yeah" Klaus said. "but this case is different Elena. You're supposed to steal an evidence" At that, my smile faded. "It's your last and most dangerous case".

"I'll handle it" I said and Klaus nodded before he left. He knew I would need time to go through the target's information. I sighed and opened the envelope.

Damon Salvatore

Son of FBI agent Giuseppe Salvatore, owner of his mother Lillian Salvatore's private firm. Have one brother named Stefan Salvatore, who is currently in relationship with town's sheriff's daughter, Caroline Forbes.…

My hands trembled and envelope fell from her hands. I didn't have to go through for more information as my eyes scanned the address… 'Mystic Falls' …

8 hours later

I pulled in front of Mystic Grill, the rain was pouring heavily on windshield and I took several deep breaths. Before I started working on my plan, I decided to grab a drink. Several hours drive had exhausted me and I needed a few hours sleep.

I ran on my way to grill, I was half drenched. My hair which was in a bun, fell in layers on my shoulders and I rubbed my hands for warmth. I took a seat on the booth, making myself comfortable. I couldn't help notice that Mystic Falls hadn't changed a bit. Same shady walls of grill, loud Friday night's chatter….

"Whisky" it was all I said before I started looking around.

"I thought you hated whisky" a familiar velvety sound made me jump. I looked in the direction of the voice to see a man beside me and for a moment I forget to breath. His blue eyes shined and his face broke into his signature smirk.

"Hello Elena" the black haired man tilted his head to stare at me.

"Damon" I breathe out.

So how was it? Please please review guys… Next chapter will be about Elena and Damon's relationship.. Do tell me what you think about this chapter… Please review… :)