Disclaimer: Neither Supernatural nor The Vampire Diaries belongs to me. The End.

Summary: After being resurrected from Hell, Dean follows Castiel's request and drags Sam to Mystic Falls to find a girl that might just be the key to stopping Lucifer. But when they get there, they find the town overrun with vampires and encounters the beautiful nineteen year old, Elena Gilbert, and her powerful guardian, Bonnie Bennett. With reluctance on both Elena and Dean's parts, the group begins to travel together, leaving a trail of sexual tension between Dean and Elena wherever they go. However, wherever they go, trouble seems to follow Elena and Castiel has yet to spill. What's so special about Elena? And why is she so damned important?

Prologue

Small, almond-shaped brown eyes fluttered open to see a car window, images blurring past her vision. Moaning fitfully, Elena Gilbert rose on her elbows slightly and rubbed her eyes sleepily. Yawning once more, she glanced around herself to see that she was in the back of the family car. The air was frigid, though Elena felt stuffy in her black long-sleeved turtleneck. Her parents were in the front, her father driving.

"Mom…Dad?" Her voice came out groggy. Neither of her parents seemed to hear her. The only answer she received was the constant pitter-pattering of the rain outside and the sound of the window-shield wiper as it struggled to keep the pouring rain from blurring the sight of the road. "Mom?"

"Hold on, Elena," her mother whispered, still reading some paper. Elena sat up fully now, recalling packing her things only a few hours ago. Her mother had woken her up at midnight and told her to pack a small bag and then Elena saw all black. She didn't even remember getting in a car. Matter of fact, when the hell did she get dressed? They had been in Georgia last time she checked. She glanced to her left to see an empty seat.

"Mom, where's Jeremy?" Miranda Gilbert glanced back at her daughter with a solemn look and Elena's heart started to thud in her chest heavier.

"We had to leave him behind, Elena." Warning bells went off in Elena's head. "Don't worry. He is safe." Elena leaned forward.

"Safe from what?" Her mother did not reply. Instead, the older woman went back to reading some strange looking paper. Elena glanced at it momentarily, catching what she thought was the glimpse of a strange looking symbol. "Mom, where are we?"

"Virginia," Grayson Gilbert replied gruffly and Elena glanced at him as he stared into the rear view mirror. Elena gulped as she noted the gun in between her parents. "We're five miles from Mystic Falls."

"But why are we here? I don't have to go to school until September." Elena was attending Mystic Falls University, one of the smallest universities that Elena had ever seen. It was the only one that she could think of that was closest to her best friend, Bonnie Bennett, who lived in Mystic Falls. As a student in the National Honor Society, Elena was accepted with a full scholarship.

"Elena, understand that things are complicated right now." Elena gulped at her father's words and the sharp tone in his voice. Something was completely off and Elena wasn't sure if she actually liked this.

"Complicated how?" No response. A flash of lightning shot across the sky and the thunder crackled right along with it. Elena gasped before turning back to her parents fearfully. "Complicated how!?" Miranda Gilbert sighed as she hid the paper in a book. Turning in her seat, she smiled to Elena with tears in her eyes.

"Elena, you need to do exactly as I tell you," she said and Elena nodded, tears gathering in her own eyes. Miranda handed her the book. "Something is about to happen and whatever you do, go find Bonnie. She is the only person you need right now. Follow the trail in the woods. Do not stray from the path, do you hear me?" Elena nodded as a single tear fell down her cheek.

"Mom…please." Elena was sobbing now. "I don't understand."

"I know, sweetie. And I wish I could make you understand." The older woman reached back and tucked a strand of Elena's pin-straight dark brown hair behind her ear lovingly, thumb stroking her child's cheek and brushing away a tear. "Just know that you will always be my little girl. And I will always love you." Elena didn't need to even look at her father to know that he was thinking the same thing.

"I love you both too," she replied and Miranda sighed, turning back around in her seat. Another flash of lightning struck the ground before their vehicle and a violent scream tore through Elena's throat as the car flipped. It crashed onto the pavement upside down and Elena fell onto the roof, glass shattering all around her.

For a few moments, all was silent save for the constant raindrops. Then Elena coughed, raising her head slowly to reveal a small cut on her forehead. Coughing again, Elena struggled to raise herself on her elbows and glanced at one of the back windows. Shards of glass dug into her forearms and Elena, gritting her teeth at the pain of having to move her pained body, kicked the window, knocking out the rest of the broken glass. Heavily, Elena climbed through the window and fell onto the cold, wet floor.

"Mom? Dad?" She croaked out, but neither person responded. Elena, now stronger, climbed to the passenger side and gasped. Her father was draped over the wind-shield, not having worn his seatbelt. He had crashed through it, glass embedded along his forehead. His eyes were wide open. It didn't take a genius to know that he was dead.

Miranda Gilbert was still strapped to the car and was hanging upside down. There were cuts all over her face, a severe one dripping with blood. Elena even made out a piece of glass in it and cringed. The woman's arm was bent awkwardly, a silver chain visible from her hand. The rain soaked up Elena's clothes and hair, but she stayed and shook her mother, praying like hell that she was still alive.

"Mom?" Elena cried. Miranda Gilbert didn't stir and Elena shook the woman even fiercer, determined not to lose another family member. "Mommy!" Miranda moaned, stirring slightly. Her eyes opened slowly and blurrily, she saw her husband's corpse hanging out of the car. Sighing, she turned to see her daughter's tearful face.

"Elena, go," she moaned and Elena shook her head.

"Not without you!"

"Go," she said forcefully and Elena only sobbed, covering her mouth with one of her hands. The rain mixed with her tears and another flash of lightning shot out. Elena glanced around her fearfully, wondering what was out there. "Elena, do what I say and go. Do you remember what I told you?"

"Find Bonnie," Elena replied and choked back a sob when the hand of her mother's bent arm opened slowly to reveal Miranda's beloved necklace. It was a diamond-encrusted angel-wing necklace hanging from a sterling silver chain. "Mom, don't do this."

"Take it. God will always keep you safe." Elena peeled the necklace from her mother's hand and stared into those familiar brown eyes one last time.

"What are you going to do?" Miranda Gilbert smiled sadly, a small cut forming on her lip that Elena hadn't noticed. Blood slowly started to ooze from it.

"What I have to," she replied softly. Thunder roared in the air and Miranda narrowed her eyes at Elena. "Leave, Elena. NOW!" With one last sob, Elena took off, slowly disappearing into the dark forest. Before could get too far from the road, Elena heard a loud explosion and whirled around only to see smoke float into the air.

"NOOOOOO!" Elena screamed and slid down against one of the trees, sobs tearing through her body as she cried. She didn't know how long she stayed in the rain crying, but when she arose, the rain had stopped. Fighting back the desire to go see if there were any remnants of her parents, Elena followed the ground with her eyes before coming across a small path.

After five minutes, Elena knew that she was officially lost. But she refused to stop running. That was the last parental order that she had received and if she hadn't followed any of them in her eighteen years of existence, she would now. Her boots sunk into the wet mud and before, Elena would have thrown a bitch fit. But she didn't care. Just as she was about to make a left turn, a cold hand shot out and grabbed her by the throat, slamming her into the nearest tree. Elena gasped as she stared into piercing black eyes.

"Please…" She begged tearfully, fear causing her chest to constrict painfully. "Please don't kill me." The strange man just stared at her evilly, a sinister grin on his face. His hand tightened painfully around throat and Elena, recalling old defense lessons, brought her leg up to kick him.

However, the man gripped her right leg and used to swing her to the floor. Elena slid into the mud until she slammed into a tree, hitting the back of her head first. Elena's vision blurred momentarily before she stared up at his face dazedly.

"HELP!" Elena screamed as he approached her, struggling to raise herself onto her hands and knees to crawl away. "Somebody…please! Help!"

Without warning, the man began to cough and Elena watched in disgust as black smoke began to erupt from his mouth. He gagged repeatedly as the cloudy substance surrounded his body until there was nothing left and his crumpled body collapsed to the floor. The dark clouds faded away and Elena glanced to her left at the sound of approaching feet. Brown eyes met with understanding and familiar green ones.

"Bonnie," Elena breathed, relief and confusion filling her soul. Bonnie nodded sadly, green eyes observing Elena's bruised and cut form.

"It's been awhile, Elena." Was all Elena heard before she completely blacked out.