A/N: Hey guys thanks for the great reviews and a big thank you for even reading my story! I've been having a lot of fun with it and hope you stick around to see how it unfolds. I hope you love Chapter 2 as much as I do and please review! Your feedback means a lot, thanks!

P.S Will try to finish Chapter 3 as soon as possible.

Chapter 2

"What were you thinking?" Elena's voice echoed through the awkward silence.

"She was probably thinking she had an itch that only Damon could scratch," Damon responded, with a smug look that made Elena want to slap it out of him.

"I don't think I was talking to you," Elena muttered. She kept her eyes on their faces; she didn't want to see any body parts. "Caroline get your clothes."

"But I didn't even get to orgasm!" Caroline pinched her voice in disapproval.

"This is why I didn't want to come to this stupid party."

"Did you just call my party stupid?" Damon tilted his head to the side.

"Caroline. Clothes. Now."

She picked up her clothes off the floor and rushed out of the room into the bathroom across the hall.

"Seriously? You had to go after one of my best friends?" Elena said with disgust.

"It's not like I forced her. She came to me darling."

"Do not call me darling. Ever." Elena stormed out of the room, down the stairs, and ran to Bonnie who was chatting away with Stefan. She felt horrible for interrupting them.

"Elena what's wrong?" Bonnie asked worriedly.

"Caroline…she…" Elena trailed off. "…you know what? Forget it. I'll be over there. You have fun with Stefan."

"Are you sure?" Bonnie grabbed her elbow to stop her from leaving.

"Positive," Elena ingested. "I'll come in a while so we can leave."

"Okay then." Bonnie nodded and turned back to a confused looking Stefan. Elena gritted her teeth when she saw a now fully dressed Caroline coming down the steps.

"Elena let me explain," Caroline pleaded.

"Explain what?" Elena said, through her teeth. "That you just became another notch on Damon's belt?"

"It wasn't like that," Caroline replied, her voice shaking with registered embarrassment. "It just hit me right now…I have no idea what I was thinking. He's just so charming with those lovely blue eyes and he makes you want to tear off your clothes just being around him."

"Really? I didn't realize I was naked when I was talking to him," Elena voiced sarcastically.

Caroline jabbed a finger towards her. "Stop being judgmental…you're supposed to be the understanding best friend."

"Yes," Elena said. "but I'm also the logical friend. What you did was stupid as hell. I know you aren't a virgin or anything but you couldn't have been talking to the guy for more than a couple of minutes and already you let him in your pants."

"Elena," Caroline spoke, examining the floor with carefulness. "Don't make this harder than it already is. I got the memo and I already feel like shit."

Elena glared at her and shook her head in displeasure. "Fine, but please do us all a favor and stay off of him."

"Are you going to tell Bonnie?"

She shrugged. "I'm not the one who should be telling her."

Caroline was about to reply when the sound of Damon approaching them interrupted.

"I hope what occurred tonight won't make you leave," he told them. He sounded so sincere Elena couldn't believe what a good actor he was.

"Who are you trying to kid?" Elena spat, recovering her composure. Damon, humming a tune under his breath, retrieved the jacket that hung on his shoulder and stuffed his arms into it.

"Why would I kid about that?" He asked in a cool voice, while buckling his belt. "Maybe I want you around?"

"Are you seriously trying to flirt with me?"

"Don't flatter yourself darling. I'm doing this so you won't be mad at my Care-bear." He tilted his head towards Caroline. Caroline cowered behind Elena. "It's not her fault she found me irresistible. I could only blame it on whoever decided to bless me with these angelic good looks." His glacial blue eyes were making Elena feel a little out of it. Just staring at him made it hard to stand straight….Having him so close only added to her insanity. Still, she felt no desire in ripping off her clothes for him.

"We are leaving in a little bit. You can go now, thanks."

"As you wish." Damon raised his hand in defeat. "But if you ever change your mind and want a good roll in the sack…let me know."

"In your dreams," she muttered.

"I wish you wouldn't have dragged me to this party," Elena sighed running her hand through her long brown hair. "As much as I love parties…I can't stand him."

"I know I'm sorry…no more Damon parties, promise."

"Let's hope so."

The next day at school Elena had found that word about Damon and Caroline hooking up had spread like wildfire. She could here hushed frantic voices as she passed people in the hall. She didn't know why it was such a surprise…Damon had a reputation of sneaking into every girl's pants no matter the age or how innocent. Elena had no response to the girls who would approach her asking for confirmation of the said "hook up."

"Everyone knows," Caroline said gloomily to Elena who was now retrieving her books out of the locker. "They all have the 'I know what you did slutty girl' look."

"Well what did you expect?" Elena scoffed. "For them to invite you to the 'Nuns are Us' club? You knew that having any sexual involvement with Damon would have its consequences. Gossip being the number one."

"You really know how to comfort your friends Elena," Caroline observed.

Elena shut her eyes and inhaled before replying, "I'm sorry Caroline…I guess I'm just mad about what happened last night."

"It's okay. I completely understand why you are mad," Caroline nodded. "I'm a slut. I love dicks and cum all over my face. It's a horrible lifestyle, I know."

"Eww too much information," Elena laughed. She looked at Caroline who was staring blankly at someone. To her terror of course it was Damon.

"Hello ladies," he greeted with his kilowatt smile. "How are you on this fine morning?"

"If you have something to say get to it now," Elena told him.

"Care bear?" Damon crooned sweetly. "Do you mind if I have a quick word with Elena? It won't be long I promise."

Caroline looked at Elena for reassurance and with a nod from her she ambled away.

"What do you want?" She sucked in her breath.

"I know we haven't gotten along lately at all—"

"We've never gotten along," Elena cut him off.

"Right," Damon continued. "But you see…I would love if we could maybe try getting over this silly little grudge you have and—"

"I don't have a grudge you—"

"Could you possibly let me get a word out without interrupting?"

"Go on," she muttered squeezing her hand into a small fist.

"And like I said…I don't want there to be this tension always between us…I was wondering if you would go out with me sometime?" He flashed her a Joker-like grin.

"You are asking me out on a date? Are you serious?"

"Don't faint on me now darling," he chuckled. "I know it's amazing and all."

"Oh no I didn't mean 'are you serious' as in this is the greatest moment of my life. I meant 'are you serious' as in what the hell are you thinking asking me out of all people out? I mean I hate you and when I say hate I mean you are like mustard and ice-cream mixed together. It's disgusting."

"Excuse me?" Damon raised an angry brow.

"Listen…Why don't you pick up your dignity off the floor and leave this conversation because I have a feeling you don't handle rejection well considering you've never experienced it before."

"Oh Elena…little Elena," Damon said amused, no hint of embarrassment tinted his words. "If you really think you scare me off with your imprudent little words you really don't know what vampire you are dealing with." He pushed Elena against her locker door, his breath striking her with such force as he whispered, "I can have anyone I want darling. I'll have you before you know it." He gazed down at a helpless Elena, smirked, and then sauntered away.

Bonnie held her books tightly with her arms as she walked out of the school doors. She needed to get to dance rehearsals and she was already running late. She glanced at the empty surroundings around her and almost died of a scare when Damon appeared out of nowhere besides her.

"Hello little bird," Damon said innocently.

"Hi…" Bonnie glanced at him with confusion etched upon her face.

"You look remarkably beautiful today, "Damon complimented her, his eyes burning into hers.

"Okay what is it that you want? You obviously need something."

"I'm shocked that you would think that little of me." Damon placed a hand on his chest as if he were hurt by her words.

"I have to get to dance class."

"I need you to convince your B.F.F to go on a date with me," he revealed finally.

"What? She would never—"

"Pretty pretty please with a virgin's cherry on top?"

"Damon, she hates you. You are giving me nothing to work with."

"If Elena would listen to anyone it would be you Bonnie. If you do me this teensy little favor I'll help you out with Stefan. I can be very convincing when I want to be hence why you are still in this conversation."

"Why should I help you?"

"Because I like you Bonnie. You are like a sister to me…a hot sister."

"If I do this…you swear you will help me with Stefan?"

"Scout's honor," Damon replied.

"Were you even a boy scout?"

"No but I ate one once."

"How sweet," She responded, looking at him weirdly.

"I'll talk to her when I see her. No promises that she'll actually agree."

"That's all I want. Just a nice girl talk over nails and Dragon Tales or whatever it is that you talk about."

"Dragon tales? Seriously? I have to go now. Bye Damon."

"Bye little Bon-Bon," Damon said with a sly smile. "And remember I will talk to your Prince Caspian tonight."

"Where is Caroline?" Elena asked Bonnie after she shut the door behind her.

Bonnie plopped herself on the couch before answering, "She's running late. She'll be here in a little bit. She sent me a very vague text so I don't know why."

"When aren't her texts vague?" Elena laughed. "So how was dance class?"

"Eh same as usual," Bonnie replied, stretching then letting out a yawn. "Clarissa was being a bitch of course. I swear she just loves wasting her breath criticizing me."

"Why do you put up with her?" Elena asked bewildered. "She's evil…like Gollum evil."

"True," Bonnie agreed. "But I love dance class so I guess it's just a price I have to pay. Besides imagine how great of a dancer I'll be once it's all said and done."

"Way to look at the glass half full." Elena sat beside her, crossing her legs. "So you'll never guess who tried asking me out on a date today."

Bonnie looked at her in the best astonishment she could sum up. "Damon?"

"How did you know?" Elena felt a wave of suspicion.

"Lucky guess." Bonnie shrugged, sinking down into the sofa.

"Bonnie," Elena muttered. "Tell me now."

"Well I mean everyone sees the way he looks at you," Bonnie said with a defeated sigh. "It's so obvious that he wants you. You wouldn't ever consider giving him a chance?"

"Bonnie—," Elena began.

"I know you hate him," Bonnie cut her off. "But why exactly do you hate him? Besides the fact that he is a player and besides what happened last year—"

"You of all people are asking me this?" Elena half closed her eyes before glaring at her. "Damon. He's a prick. He uses girls for his amusement and that does not sit well with me. He's immature and I just can't stand the way he thinks the world is in love with him. I'm not into guys like that."

"So you don't think he is hot?" Bonnie asked.

"Sure he is attractive but that's not what matters," she admitted. She opened her mouth but shut it quickly before she revealed to Bonnie that she thought he was the most gorgeous guy she had ever seen.

"Maybe underneath that bad boy persona lives a sensitive guy," Bonnie suggested, looking at her wide eyed.

"How cliché. Anyways, why all of a sudden did you become his lawyer?" Elena's eyes darkened.

"Because I think there might be more than meets the eye with him. Who knows you could end up falling madly in love with him."

"Bonnie, I'm a virgin. I do not want to lose my virginity to someone who has done more than half the world. When I have sex…I picture a fireplace in the background and my stuffed teddy bear blindfolded."

"Maybe his experience would make it better for you."

"Eww please be quiet now." Elena indicated with a wave of her hand.

"Sorry," Bonnie spoke softly. "But promise me you will think about it."

"If that helps you sleep at night, sure." They both turned their attention to a heavy breathing Caroline who had just barged into the living room.

"So—Sorry I didn't knock," She breathed. "Water?"

Elena sprang up from the chair, went to retrieve a water bottle from the kitchen and came back to give it to Caroline who was already sitting next to Bonnie on the couch.

"Caroline, isn't it a little too early for your corner job?" Bonnie teased.

"Ha very funny," Caroline said between gulps of water. "My car broke down. I had to run over here!"

After Caroline's breathing returned to normal she exchanged curious glances with both girls. "So…why the weird faces? Don't tell me one of you is pregnant?"

"Oh please," Bonnie scoffed. "We don't even have sex. Out of the three of us you would be the only one with a chance at getting pregnant."

"Yeah why is that? I'm curious to know your insane reasons behind the Mickey Mouse purity rings."

"Not all of us give in with a few words and a smile," Elena responded.

"Ouch, "Caroline's voice squeaked. "Thanks but I already know you registered me for Slut Academy."

"I don't want to have sex with anyone other than Stefan," Bonnie stated. "I do not want anyone else's pinky inside of me."

"Oh well Damon definitely does not have a pinky! I would know—"Caroline stopped short at the look etched upon Bonnie's face.

"What…did you say?" Bonnie asked in bewilderment. "You…had sex with Damon?"

"I—yeah. At his party last night," Caroline admitted shamefully. "Elena caught us."

Bonnie looked over at Elena whose eyes were glued onto the tiled floor. "You knew? And you didn't tell me?"

"Caroline was going to," Elena said, her eyes rising to meet Bonnie's. "I didn't think it was my business to inform."

"We are best friends!" Bonnie shook her head in disappointment. "Caroline…why?"

"I don't know why." She looked startled. "I guess…well I mean…who could resist him?"

"Damon was just using you as his toy. Everyone knows he's been interested in Elena since last year when—"

"Stop, please," Elena spoke quietly. She didn't want to remember the events that had happened last year. They tore at her heart like painful glass wedged into her.

"Sorry," Bonnie apologized quickly. "The point is Damon is off limits. No more…understand?"

"Yes," Caroline sighed. "I understand.

"Damon," Principal Mary Truscott said in surprise as he closed and locked the office door behind him. "You frightened me…Why are you here so late?"

"You know why," Damon said seductively. "I wanted to see my little Mary."

"Damon, I can't….I have to get home to Greg."

"I'm sure your husband can live a few more minutes without you." Damon trailed a finger on her desk and looked up at her with his piercing blue eyes.

"I can't…I already told you. He is waiting up for me…we are supposed to go out to dinner."

"He can have you after I'm done with you." Damon appeared behind her in a blink of an eye. He used his hands to explore her breasts as he trailed kisses down her neck.

"I really shouldn't…" Mary began but her words turned into a moan as she felt his hardness pressing against her back. Mary had only ever had sex with her husband and had thought that his six inches felt big inside of her. She was proven severely wrong when she had somehow taken Damon's anaconda sized gift all the way in. He stretched her in ways she had never thought possible. As Damon continued kissing her neck he tugged her skirt down enough where he could slide into her.

"Damon stop I've never—"

"Never what?" He smirked.

"Never taken it in the back," she admitted her face a deep red.

"Well at least I can take that virginity," he chuckled. Without waiting for approval in one motion he slid into her and covered her mouth as she screamed out in pain. She bit his hand hard as he stroked within her, reaching the end. After she grew used to the intrusion he uncovered her mouth and placed his hands on her hips. He held her tightly as he continued ramming into her little hole.

"I have to ask you for a tiny little favor," Damon breathed into her ear suddenly.

"W-What is it?" She managed to say through moans. "Anything."

"Could you give Elena Gilbert detention tomorrow?"

"E-Elena Gilbert? But she doesn't d-do anything w-wrong."

"Just do it," he growled as he thrust into her hard and fast almost breaking her. "Make something up. I'm sure you can think of a few ideas. Attendance…harassment…too much Bob the Builder?"

"O-Okay." She backed into him trying to swallow him whole. "Done."

"Good." A smile crept onto his face.