This is my first M rated fanfic. Please review. I hope you all like.

Elena Gilbert sat at her vanity mirror brushing her long, chestnut hair. Thinking about her life … that was slowly going to hell. Her cousin Isobel was moving to Mystic Falls. Mystic Falls of all places! It was only because her father, Elena's Uncle John, had gotten a job at the FBI office in Richmond. John claimed her wanted Isobel to have people to care and look after her while he was away and that was the reason he was moving back. Elena called it bull. Isobel was eighteen, she could look after herself, too bad her father or uncle did not see that. Isobel had it out for Elena, everyone knew that. Isobel wanted everything Elena had including him. That was the only thing she had ever gotten or so it had seemed. Elena pulled open the top drawer on the desk and took out the picture of her mother with her and her sister, Katherine. Katherine had no idea Elena had taken the picture from her, and Elena did not know why she or Katherine bothered to even keep it. Katherine Gilbert was Elena's twin sister, identical in every way except personality, the shade of brown of their eyes and the birthmark that rested on Katherine's neck. At seventeen, these twins were inseparable still. Elena's eyes stung with the threat of the impending tears which she would not let fall. Their mother, Miranda Gilbert, was not anyone special to cry over. Their family had learned that the hard way when Miranda left when the girls were seven. No warning or sign, just a closet devoid of clothes. Elena found the picture in drawer buried under important papers. She remembered the day they had taken it like it was yesterday. It was the day after her parents' anniversary. Miranda had taken Elena and Katherine out for a girls' day. It was one of the best days of her life. Miranda paid for the picture that was in her very hands, it was at the zoo. Elena and Katherine loved the zoo. Elena's favorite animals were the polar bears and Katherine's were the panthers. It was a perfect day, no knowledge that three months later Miranda would leave. Katherine resented Miranda that much Elena was sure of. It was an unspoken agreement that the woman would not be spoken of or referred to in Kat's presence. Elena neither loved, liked nor hated the woman. She was indifferent to her, cold even. The only reason she could think of why she kept looking at this picture was because of the perfect memory it held, not in remembrance for the woman who abandoned her three children. Elena heard footsteps coming toward her room and quickly stashed the picture away. A couple seconds later Katherine walked into the room she shared with her sister and plopped down on her king sized bed. Elena didn't mind sharing a room with her twin; they loved one another despite their differences. The bonus was that their room took up half of the second floor to the Gilbert home. It reminded her of a penthouse suite minus the kitchen. It held a large bathroom with a shower to fit twelve people and an oversized tub which one could have a party in. The girls made a lounging area for when they had guests. Elena turned back toward Katherine smiling.

"What's wrong Kat?" Elena questioned.

Katherine was not one to hold things in. Sure, she was a first class bitch. Anyone who had spent more than a few hours with her would discover that. However, Katherine was also loyal to a fault, sneaky, vindictive, charming, brutally honest, trustworthy and she cared too much about those in her tight circle.

"Jeremy's looking for you." Katherine spoke with a hint of amusement to it.

Jeremy was their older brother. He was turning twenty-two in five months. He was overprotective over his little sister to the point where it could be suffocating ever since Katherine sprouted breasts at thirteen. Jeremy was a successful businessman with his partner and best friend. He took care of his sisters paying their car insurance bills and making sure they always had money to spend. That money however did not always come from his "businesses." Elena and Katherine knew about who Jeremy really was. Sure, he owned the hottest clubs in Mystic Falls and the three surrounding towns as well as almost every bar except The Grill. That was his cover. Jeremy sold weapons, illegally of course. He was a loan shark. He owned working girls who worked at his "strip club" in Wellington, the next town over west. The funny thing about it was that Jeremy went to church every Sunday, repenting for his sins. Elena found that the most funny. Her brother must have a lot of sins to repent for, but who was she to judge? His dealings, legally and illegally insured her safety and wellbeing . His illegal dealings started when she was in the seventh grade, because she knew he never had the money to open the bar and the club at eighteen with his best friend. Jeremy and his friend owned the town and they knew it.

"Why?"

"Apparently Mason called looking for you." Katherine revealed.

Elena sighed. Mason Lockwood who was now in medical school at twenty-two was a godsend in Jeremy's eyes. He wanted someone like Mason to marry Elena. Elena knew for fact Mason was enrolled at the University of Richmond but it was June now. Everyone was on break for school. Mason made it clear his sophomore year of college that Elena was it for him, Jeremy was overjoyed. Okay he was hot. Tall, built like a quarterback, caramel swirl hair and a smile to make panties fall. Elena would never deny that. Elena had rolled her eyes saying "Mason's not my type." Yet neither Jeremy nor Mason got the hint.

"Can't I just fall for some young jock like you?" Elena joked.

Katherine had been in a relationship with Elena's best friend, Stefan Salvatore for the past three years. It had been rough at first with Stefan's crazy ex-girlfriend Rebekah not letting go of him. Katherine however was sneaky and manipulative; Elena knew it was only a matter of time. Stefan Salvatore had an innocence to him that was easily convincing. Everyone thought that Elena and Stefan would end up together but Elena had a thing for bad boys. Stefan was the captain of the lacrosse team, president of letterman, Mystic Falls High Radio producer and the best person Elena knew. They had been best friends since they were born. Stefan had light chocolate hair, a lean built, luscious green eyes and a smile that could light up a room. He was serious yet playful, honest yet cautious, loyal yet fair and Elena had no idea why he dated crazy girls like Rebekah or even her sister. There were so many girls who still wanted to date him regardless of his relationship status, girls like Amy Bradley. Opposites must attract, Elena had thought when she had met Rebekah. The two dated for a troubling six months before Stefan ended things. Elena had a feeling it was because Katherine made her interest in Stefan obvious after years of pining after him. Of course, her sister denied it whenever Elena teased her of having a crush on Stefan. As soon as Kat flirted with him, he dumped Rebekah without so much as a reason why. Elena knew the two had started seeing one another even though they had tried to hide it. The late night calls, smiles, heavy flirtation, lustful stares and the hickies lining Stefan's neck were all the evidence she had ever needed. Rebekah had tried to everything to get Stefan back from spreading rumors to attempting to assault Katherine. The latter failed miserably and everyone realized it when Rebekah had to change her entire schedule to avoid Katherine. The black eye, busted lip and multiple facial and arm bruises on Rebekah were a warning to everyone that Stefan would always be Katherine's.

"Well we all can't have the perfect romance." Katherine said smiling a Cheshire cat smile.

Elena pushed back from the mirror and desk and headed to the door. She paused before turning the knob.

"Are you coming Kitty Kat?" Elena asked smiling brazenly.

"Well, seeing as how Isobel is supposed to be getting in about now I don't-"

"Oh, if I have to see the bitch so do you. Plus I might need someone to keep me from strangling her when she comes through the door."

Katherine pushed herself up from the bed laughing.

"Funny. How could you kill you favorite person?"

"Now that was funny." Elena replied.

The girls left out of the room arm-in-arm.

"Is Dad here?"

"Yeah, his shift at the hospital ended an hour ago."

Grayson Gilbert was the head of the household. Grayson was a well-known doctor and heart surgeon at Mystic Falls Hospital. Elena knew her father knew just the minimum of what Jeremy did to help support the family, not that he needed too. Grayson provided his children with everything they would need from cars to phones to clothes and the six bedroom four bath home they lived in. Grayson did not appear to be a day over thirty five yet he had just made forty-two. Elena never knew if her father had dated after her mother, if he did, he did it well enough to keep it a secret for ten years.

"So is Stefan coming over?"

"Yeah. He misses you." Katherine tells her sister.

Elena wondered why Katherine had never jealous when it came to her friendship with Stefan. Elena figured Katherine assumed that if Elena and Stefan wanted to be together they would have been years ago.

"I know. My best friend has been way too much with his high maintenance girlfriend." Elena joked as the girls walked down the stairs.

Katherine nudged her sisters in the side. Elena could see Jeremy standing in the vast living room with father talking.

"Hi Daddy." Katherine said, putting on the innocent act.

"Hi Kitty. How was your day?"

Elena could never get why Grayson insisted upon nicknames for his children. Katherine got Kitty. She got Butterfly. Jeremy was the lucky one who got Tiger.

"Good. Stefan is coming over later. I hope you don't mind."

"I hope he stops by before I leave for my next shift in four hours. I haven't seen my son in law in weeks."

Elena could only laugh. Stefan had Daddy's blessing from the womb.

"He will. I don't think Damon wanted to intrude on John and Isobel's welcoming so they will be here later."

As soon as Damon's name came out of her sister's mouth, Elena zoned in on the conversation.

"Damon is very smart. He should continue to get that business degree. It could help the businesses Jeremy."

Elena saw her brother only nod at his father's comment. Damon this and Damon that, who cares Elena thought. Damon was a self-glorified douchebag. Damon Salvatore was Stefan's older brother and Jeremy's best friend. He was like a god with sex appeal as his greatest attribute. His dark raven hair always glistened like grease in the sun. His cerulean blue eyes were intense and pulled you in with one look. If one took a look at his body, it was obvious he had could have been a professional swimmer. Elena knew he would have been if he wasn't left to take care of Stefan and his younger sister, Amelia Salvatore who was twelve. Damon was getting recruited for the Olympics when his father was murdered in a robbery. Everyone knew that when the same men who robbed his father and stabbed him turned up dead two years ago, Jeremy and Damon had something to do with it. Damon was cocky to a fault, persistent and most of all dangerous. Well as dangerous as Jeremy. He had pulled Elena in one time but that was then. Now she could barely stand the sight of his stupid signature smirk that made her core vibrate with need.

"Whatever." Elena mumbled catching Katherine's attention.

Katherine was one of only four people who knew everything that happened between Damon and Elena two summers ago. Elena had been fifteen and foolish but she would never be again.

Flashback

Elena watched at Damon grabbed a towel off of the rack in the bathroom she shared with her sister. His chest was glistening with a mixture of sweat and water from the day down at Tyler's water hole. She couldn't help but stare at the Adonis before her.

"Elena, did you hear what I said?"

His velvet voice pulled her out of her own trance.

"Hmm?" She asked looking up at him.

Her cheeks flushed red as she realized he had caught her staring at him. It was no secret Damon Salvatore was sexy. Everyone including Damon knew it.

"No need to be embarrassed. Lots of women stare at me."

Elena's breath hitched in her throat before she shoved Damon. She knew he was only teasing anyway. She was his best friend's little sister. He was four years older than her. What would a nineteen year old sex god want with a fifteen year old virgin? It seemed like she was the only virgin left in the world. Caroline was having sex with her summer fling Trevor. Katherine was always gone with Slater somewhere and Katherine wasn't modest about her sexual needs. Stefan was letting his crazy girlfriend Rebekah get him off. Matt was doing all sorts of crazy things with the new girl Andie. Tyler was getting tail from girls who didn't even know his last name. Elena was the only one stuck, not that she had minded before. Yet ever since Damon came back from getting his little sister Amelia from North Carolina from their Uncle Zack, she couldn't help but notice how she wanted him. Her lack of experience and his inexperience of not getting any was a problem for her.

"Elena." Damon said, drawing out her name with sexual implications like he had been doing all summer.

Elena just turned around and smiled at him angelically.

"Yes Damon?"

Damon's breathing went uneven. Elena watched him close his eyes and breathe slowly like he was practicing restraint. When he opened them, he just smirked at her. Elena's core filled with a warmth she was familiar with all too well ever since Damon arrived back. He approached her slowly, reminding her of a black panther stalking its prey.

"This isn't supposed to be happening." Damon whispered to her as soon as they were close enough that their noses touched.

"What isn't supposed to be happening?" Elena asked with curiosity.

"You're my best friend's little sister. My little brother's best friend. I'm not supposed to want you."

Elena's mind suddenly went into overdrive. Damon wanted her? Did she get sent into a parallel universe where all her dreams would come true?

"You probably think I'm just some big pervert now. Jer would kill me if he knew I was even in your room."

"Jer's in Georgia." Elena sprouted out.

It was the only thought her mouth could process at the moment. She shook her head, trying to gain momentary control.

"You're not a pervert. I … all summer I've been feeling like I'm losing my mind. You … came back and I don't know why I feel like this. Maybe it's because I've barely seen you in the past year and my teenage hormones are in overdrive now that I'm becoming a sophomore. I just feel like a magnet. You're drawing me into your field." Elena replied back, voice husky with lust.

She watched Damon's eyes darken into a teal color right before her eyes.

"I think we should do something about it then." Damon told her.

"Maybe you should." Elena replied back batting her thick lashes.

Damon wasted no time. He grabbed Elena's waist and pulled her toward him. As soon as their lips touched, stars erupted under her lids. Her mouth latched onto his. Their tongues fighting for dominance, matching each other perfectly. Elena wrapped her arms around his neck, pushing herself into his body. His want for her became apparent when Elena felt the giant bulge through Damon's swim trunks. Elena wrapped one leg around Damon and he lifted her up to wrap her other leg around his waist. The two fell back into Elena's giant bed with Damon on top.

"This is so much better than my dreams." Damon mumbled huskily.

"You dream about me?"

"Oh, I do more than that. When I came back and saw you for the first time, I had the biggest hard-on in my life. I hid it with my jacket for three hours. When I got home, I got myself off thinking about the way you ate that banana." Damon told her before biting on the sensitive skin between her neck and ear.

Elena shivered with the bite, moaning at the same time.

"That's my favorite sound. I'm going to take you to another world."

Elena giggled a dangerous laugh which neither she nor Damon had ever heard come from her before. Damon pushed his hard on into her core, trying to get some type of friction. Elena moaned into his ear. Suddenly Damon stopped and looked into her chocolate doe eyes.

"This isn't a one-time thing Elena. This isn't just sex to me. I like you a lot. And I know if I'm risking my best friend trying to kill me then I want you to know how I feel. This summer started the physical attraction but I've always had a thing for you."

Elena's eyes widened with the revelation Damon told her. She swallowed heavily before regaining eye contact with him.

"Then we'll be together." Elena told him.

Damon smiled diving back in for the reunion of their mouths but Elena pulled away. The confusion and hurt in his eyes melted Elena's heart.

"I'm a virgin." Elena said looking him in the eyes.

The shock registered in his face before he recovered.

"That's okay. It'll be more special then."

Elena couldn't help but allow a part of her to fall for Damon when he said those words. She quickly reattached their mouths. Damon's hands worked their way to her ribcage before he gave their attention to her breasts. Damon quickly pulled the bikini string loose and threw the fabric across the room. His hands gently cupped Elena's breasts and he smiled. Elena moaned upon the contact.

"Perfection." She heard him say.

Damon took one pebbled nipple into his mouth causing Elena to arch her body up to him. His right hand played with her other nipple as he suckled the dark pebble into his mouth. Elena panted as she felt wetness pull between her thighs that had nothing to do with being at the waterhole all day. Damon's freehand went down to Elena's short shorts which he began to unzip. He unlatched his mouth from her to help her remove the shorts. Damon threw her bottoms in the same direction he sent the bikini fly. He slowly hooked his thumbs into her bikini bottoms and started to pull them down. Elena thanked God she had gone waxing with Kat yesterday. While she had been in pain yesterday, her lust overrode the pain she would ever feel. The bottoms dropped from Damon's hand and he smiled like a lioness on the hunt.

"Scoot up into the bed." Damon told her.

Elena got on her elbows, sliding back through the bed. Damon followed suit, standing up on his knees with his trunks still on. His hard on fighting to get through. He lightly pushed Elena down to lay flat on the bed. He lowered himself level with her core. Elena was breathing with anticipation. She was going to lose her virginity to Damon Salvatore! Elena shivered when she felt his two of his fingers push her folds apart. Her breathing was erratic, her heart beating faster than humanly possible or so she thought. A moan escaped her lips when she felt his tongue swipe across her clit. Damon moaned tasting her sweet juices, pausing for a second then getting back to work. Damon moved his tongue up and down, riling her up for the main event. When Elena relaxed into his swiping, Damon drew her clit into his mouth and sucked on it hard. Elena thrashed and panted as Damon continued to suck on her juices. Elena gasped when she felt Damon add a finger into her opening. There was a slight pain but she felt her walls clasp onto his finger as he pumped in and out of her.

"You taste like honey and peaches."

Elena giggled then gasped as Damon returned his attention to her body. Elena felt a fire build up in her core. It felt like she was going to explode. She closed her eyes as white lights appeared before her closed lids. She felt like waves of pleasure hit her body. She ground herself into Damon's face. She felt him remove his fingers from her as the waves she felt subsided and Damon rose up with a giant smile, face covered in her juices.

"I felt like a volcano."

"You had an orgasm. Don't worry, it will not be the last between you and I." Damon said cockily making Elena laugh.

Damon pushed his trunks down. Elena could not help that her eyes widened at the sight of Damon's dick. It was big, bigger than any pictures of one that she had ever seen. It was bigger than Jason's, the first and only boy she had repeatedly given hand jobs to at the beginning of her freshmen year. Elena licked her lips as she took a hold of it. She began to stroke it back and forth. Damon moaned as his eyes closed. Elena twisted her hand back and forth as she fisted him up and down. Damon's breathing turned into panting as Elena continued to work on him. Damon's dick begin to twitch in her hand, signaling he was close so she attached her mouth onto him. She sucked greedily and took as much of him in her motuh as she could. She pumped the rest of his shaft with one hand, and played with his sac with the other. Moments later, Elena felt Damon spill in her mouth. She swallowed his cum insatiably, he was all hers. Elena let his cock fall from her mouth with a pop sound. Damon breathed heavily smiling like he was sedated.

"You are a goddess." He said to her and kissed her lips.

The two moved toward the headboard as Elena slipped under the covers.

"Do you have a condom?" Damon asked her.

Elena smiled as she felt his hard-on poking her naking thigh.

"I thought you would take a while to come back for more." Elena teased.

"Normally I would but you just drive me crazy. I have to have all of you." Damon said.

Elena reached over into her nightstand and pulled out a Trojan Twisted Pleasure condom. Damon quirked an eyebrow up at her.

"Where'd you get this from?"

"Kat." Elena said shyly.

Damon pecked her lips and grabbed the condom. As Damon pulled the condom out of the wrapper, the door to the room flew open and slammed close.

"That bitch! I am going to kill her!" Katherine exclaimed.

Both Elena and Damon froze, caught in the act. When she received no answer from her twin, Katherine turned to see Damon in bed over her sister. She could see both were naked just from their position. Her hand flew to her eyes.

"Oh my God! I am so sorry! I didn't know you two were … I'm going to go downstairs. Eww." Katherine said heading out.

Elena let out a giant sigh when Katherine exited the room. Damon rolled over to the side of her. He pulled her to his chest.

"So I guess I'm staying a virgin."

"Just for tonight Lena." Damon said to her, purring.

Elena remembered that night like it was only a few minutes ago. She remembered how Damon held her for an hour before leaving. She remembered Katherine coming back into the room, drilling her for answers and having a million and one questions. The thing Elena remembered most besides that memory was what happened three weeks later when she came from Georgia visiting her grandparents with Jeremy. Caroline was on the porch waiting for her with all the latest gossip. The hottest buzz in the town was that Damon Salvatore had gotten head from Elena's own cousin, Isobel behind the new Starbucks. Elena hid her rage from Caroline who didn't know about her and Damon's almost affair. However, when she saw Kat come into their room she began yelling, crying and throwing things including her vanity mirror. Katherine had managed to calm her down but Elena was still pissed the hell off. She hadn't talked to Damon the rest of the summer or Isobel who made her attraction to the godly Salvatore brother anything but opaque. Damon had called, texted and even took to calling Katherine's phone to get ahold of her. Elena just wasn't having it. The next time she did talk to him, she was short and cold. Their relationship had improved the past two years but she would never go down that road with him again. Had he lied? She didn't think so. She believed he meant everything he said in the moment, but that was the problem with guys like him. They were all about the moment and never about forever. That was why she had started dating Matt her sophomore year, she dumped him too at the end of junior year. They would have made two years in August. Oh well, she thought! The opening of the door and voices brought her back into reality. She saw Stefan come into the house, and kiss Katherine. Her Uncle John was the next to catch her attention. Damon walked in and went straight to talk to Jeremy. Katherine smiled at Elena, giving her an approval with her eyes. Elena's eyes however had found the one thing she wished to never see again. Isobel. The bitch was back.

"Welcome back Izzy." Jeremy said, hugging the girl.

Elena smirked. Welcome back her ass.