A/N: Hi guys, so this is my first fanfiction and I'm really excited for it. Season 4 is coming up and I'm even more excited for that! This story is gonna be mainly Elena and Damon, but you'll see some Stefan and Caroline action, and I'm gonna try and incorporate as many of the characters as I can into this. I got my inspiration from the movie Welcome to the Riley's, but know that I'm not really going to go in that direction, just using it as a baseline. This first chapter is written in each different character's point of view, but in upcoming chapters I may keep it to just one character's point of view. I will eventually attempt to write some smut into this story but bear with me at first! I'm gonna try to update every week. I hate being kept waiting while reading my stories and I don't want to do that to you guys! Okay, I'll let you read now. Thank you and enjoy!


"Come on, brother. You can't keep living like this. I can't take it anymore," Stefan complained as he leaned against the doorway and looked at his brother with saddened eyes. Damon was slouched at his desk, his head hanging low. For months now, his brother had moped around the office, smelling of bourbon and pissing everyone off. It hurt to look at him. His normally brilliant blue eyes had lately become dull and empty, his raven hair was disheveled and unkempt, and he even looked thinner around the face.

Damon didn't even look at him when he said coldly, "Oh, spare me your pity, Steffy. I don't want it." Stefan didn't understand, how could he? His life was perfect. He had a beautiful, neurotic, loving girlfriend. He was their father's shining star and never had a care in the world. Damon was always the one who had to bend over backwards to please their father, who wouldn't even give him the time of day outside the office. He never took a single day off of work, even worked weekends, and got no appreciation for it. Granted, he always kept a bottle of bourbon in the office to take the edge off, but who wouldn't if they worked 90 hour weeks?

Stefan sighed. He knew his brother was miserable, but he just wouldn't accept help. "I think you should take the week off. Go for a vacation." Damon opened his mouth to speak, but his brother cut him off with his next words. "I don't wanna hear it Damon. You're miserable here." He looked at him with consoling green eyes. Getting Damon out of the office was the only option. Stefan hated seeing him like this and would do anything to save his brother.

"It's not your job to save me, Stefan," Damon growled with hard eyes. "I don't need saving, I'm perfectly fine living the way I do."

"You're not fine! You call this fine?" He threw his hands up in the air and walked towards his brother. "Have you looked at yourself lately, Damon? You can't tell me that you're pleased with yourself. There used to be days when you would come into the office smelling like sex. When was the last time you were even with a woman? Maybe you haven't noticed how miserable you look, but they have. They look at you and they practically see "Damaged Goods" on a flashing neon sign over your head! Come on, brother," he pleaded, and ran his fingers through his hair. "You're lifeless here. You need to get out." Stefan stared Damon in the eyes. He knew those words would get to him. It may have been a low blow, but if that was what it took, then so be it.

Sure enough, Damon looked up a few moments later with a resigned look on his face. Stefan was right. He hadn't been laid in well over 3 months. And it sucked. If he was being honest with himself, he hadn't truly looked at himself in a while. He examined himself enough to make sure he didn't cut himself while shaving, but he was never really seeing how bad he had gotten. It was obvious that Stefan wasn't going to let up, so why not? A vacation would be nice. Maybe the Bahamas, nice tropical weather, spend all day at a bar on the beach. His eyes glazed over and his lips stretched into his famous smirk.

As if reading his mind, Stefan said, "I'm not telling you to go drown yourself in alcohol for a week straight, brother. Just get out of New York. Who knows, when you get back maybe you'll finally be pleasant company again."

Just then, a scoff was heard from the doorway, made by a perky blonde previously unnoticed. "Please, Stefan, when was he ever pleasant company?" She rolled her eyes and gave Damon a smirk that rivaled his own.

"Well hello to you too, Caroline. It's a pleasure, as always," he said, his voice dripping with sarcasm.

She gave him a pointed look. "I did not come to see you, obviously." She ran to Stefan, threw her arms around his neck and gave him a passionate kiss. They stayed locked in their sickening lover's embrace a few moments too long for Damon's tastes. When she finally pulled away, she was all smiles and murmured a soft, "Hi, baby," to Stefan.

"As much as I'd love to watch, you have your own office, Steffy. I need to get back to work anyways." Damon hoped that with Caroline here she could distract Stefan of his mission from a few moments ago. However, Caroline is nothing if not nosy.

When Stefan gave a heavy sigh and began to slump his shoulders in defeat, Caroline immediately picked up on their tension. "What's going on, boys? Damon, what is it that Stefan wants you to do that you clearly don't want to do?" She turned and gave Stefan a knowing smile, and he smiled at her in return.

Damon waved his hand, trying to act nonchalantly. "Oh nothing, he just wanted me to cover one of his meetings for him, but I don't have the time." He truly hoped that Caroline would leave it at that, but he knew that his hope was in vain.

"Oh no, Damon Salvatore, you know better than to lie to me." She narrowed her eyes at him and crossed her arms across her chest, waiting for him to fess up. When a few moments passed with him just ducking his head, she turned to Stefan. "If he won't tell me, you will baby, won't you?" She looked to him with her big blue eyes and pouted her lips, knowing that he would definitely tell her.

"I think that Damon needs to take a week off and go for a vacation." Damon groaned at him in response, and Stefan knew that if his head was up he'd see him roll his eyes. "He's miserable here. He's rude to the employees and sooner or later he's going to start to get sloppy in his own office."

At this statement Damon immediately sat up, ready to defend himself. He lived and breathed this company. He would never slack at work. Hell, his whole life had become work. He had nothing else to live for other than this company. With a hard voice he said, "I may take my stress out on the people who work here, but I would never, ever slack in my office. This company is all I have. I worked my ass off to get here and I wouldn't do anything to jeopardize that. You know that Stefan."

"You need a life, Damon!" Stefan sighed, exasperated. "I know that this company is important to you and father, it's important to me, too. The difference with me, however, is that I know how to live outside of the office. Do you truly want to end up like dad?"

Damon knew that Stefan wasn't asking if he wanted to be president of the company with a million-dollar bank account. He was asking if he wanted to be a miserable old man, bitter and alone. Their mother, Arietta, was no longer with their father. She had left many years ago due to their father's constant absence. He always put the company before himself, and once Damon and Stefan were old enough, Arietta left the old fool. She kept in touch with her sons and saw them more often than they saw their father, and they worked in the same office building as him. Neither son truly wanted to end up with the life their father had.

Stefan and Damon shared a look, and Stefan had his answer without needing Damon to say it. Before he could press the matter, Damon's intercom rang and his secretary's voice was heard through the speaker.

"Excuse me Mr. Salvatore, I know you're otherwise occupied but Alaric just called and said it's urgent. I told him you were busy but he was not taking no for an answer, I'm sorry."

Damon sighed and said, "No need to be sorry, Andie. Alaric's nothing if not persistent. Put him on Line 2 and make sure he's on hold. I'm just finishing up here." The line went silent and Damon brought his attention back to his brother and Caroline. "Well, this has been fun, but duty calls. Out," he finished in a tone that implied the conversation they had been having was over, and waved them away.

Stefan took hold of Caroline's hand and gave a heavy sigh. "We're not done here, Damon. I'll drop it for now, though." With downcast eyes he turned to lead Caroline out of the office. She turned back for a moment to give Damon an icy glare, then walked out slamming the door behind her.

Before getting to Alaric's call, Damon opened his top desk of his drawer and popped some Advil in his mouth. It seemed he always had a headache after talking to Stefan nowadays. He groaned and picked up Line 2, ready to get this conversation with Alaric over with. "Do you really need to hassle my secretary all the time, Ric?"

"Oh, c'mon Damon, I was just having a little fun. I think she likes me." Alaric laughed and Damon could practically see his friend's goofy grin over the line. "Besides, this really is important. I just got a call from one of our new authors, Elijah Mikaelson. As you know, he just published and released his newest book, and to gain more publicity he wants to hold a televised book signing event up in Portland and he wants one of his publishers with him. Well, he wants to do it this weekend." He paused, giving Damon a moment to see if he could figure out his apprehension.

Damon groaned, knowing exactly what this meant. This weekend was Ric's one year anniversary with his wife, Jenna. He already planned a romantic weekend for the both of them, and Jenna already knew about it. If he cancelled for a book signing event, Jenna would blow a gasket. As his good friend, Damon knew he had to take this one. Elijah was a nice guy, and Portland isn't too far, so it shouldn't be too big of a deal. Sighing dramatically, Damon said, "Alright, Ric. I'll go to Portland for you. Just remember, you owe me." He practically sung the last statement, and couldn't help the smirk that appeared on his face; it was inevitable with all the crazy ways his friend could pay him back.

"Yes, of course! Thank you so much Damon! Jenna would have killed me if I cancelled, I'm sure of it. I'll concede that I owe you, but nothing too crazy, okay?" He knew Damon way too well to know all the fucked up kind of ideas that were flowing through his head. "You know that Jenna will kill you too if you try to make me do anything outrageous."

Damon scoffed. "I'm not afraid of your little wife. You should probably hang up now, before I change my mind." To his surprise, the call ended with a click immediately. Wow, he must really have something special for Jenna planned. Damon was happy for his friend, how could he not be? They had been friends and business partners for over six years. They used to go out drinking and partying every night, but ever since the day Alaric met Jenna, he had totally changed. He had to admit that the change was good. Jenna had done wonders on him, and Damon couldn't help but admire her. She was even good at holding her own against his snarky comments and snide remarks. She had much more bite than bark, the total opposite of Ric. They were good for each other, though, and as much as Damon hated to admit it, he would gladly cover a business trip for him so Ric could be with Jenna.

Pulling out his bottle of bourbon and pouring himself a glass, Damon hit the intercom button for his secretary. "Yes, Mr. Salvatore?"

"Andie, I need you to clear out my entire schedule for this weekend. I'm going to Portland."


As he pulled up to his hotel, Damon couldn't help but feel relieved. The whole past week he had spent with Mr. Mikaelson organizing this book signing event. There had been so many bumps along the way that he didn't think it was going to happen. However, with the event all smoothed out and ready to start tomorrow, Damon could now have a seat at the bar and just relax. He checked his bags, then moved to sit down on one of the unoccupied stools and ordered a bourbon.

The hotel was beautiful. It had an old-fashioned, elegant design with deep red and a mustard yellow being the main color scheme. It was comfortable, and the lighting was calming. The bar, located just to the left of the main lobby, was in the center of the room surrounded by small dining tables.

Damon's phone vibrated in his pocket, signaling a text. It was a message from Elijah telling him that he had just checked in and asking where to meet. After finishing his first drink, he sent him a reply telling him to come to the bar, and then flagged the bartender down to get a refill. As the bartender returned, Damon heard his name being called from across the small room. He turned to see the tall, well-groomed, brown-haired man walking arm in arm with a lovely blonde with blue eyes. Even though they were holding each other, there was nothing intimate at all about their embrace.

"Ah, Damon, thank you for coming." Elijah said in his slight English accent, and held out his hand for Damon to shake. Elijah then brought his attention to the woman next to him and said, "This is my sister, Rebekah. She'll be accompanying me to the signing event tomorrow afternoon."

Damon took her hand in his and brought it slowly to his lips, smirking at her. "It's a pleasure to meet you, Rebekah. I'm Damon." He couldn't help but feel smug at the blush that tinted her cheeks at his affectionate display. Stefan wasn't completely right; he still had some of his winning charm.

"Come, Damon, let us go sit at a table and eat. I hear the food here is exquisite and I'm absolutely famished. I'm sure you're hungry after that plane ride." In reply, Damon gave him a tight smile and accepted his offer. Rebekah eagerly seated herself across from Damon as they sat down, and all through dinner kept trying to win his attention. She laughed too much at everything he said, continuously smiled and batted her eyes at him. The whole experience unnerved him. She was extremely attractive, but she was trying much too hard. Her blatant eagerness was an abrupt turn off, and Damon found himself wanting to get away from her as soon as possible. She reminded him of a type of mountain lion, stalking her prey. However, there was nothing sexy about the way she did it. He tried to focus all of his attention on his conversation with Elijah, and for the most part it helped distract him from her advances.

After their meals were finished, however, Rebekah had started to play footsie with him under the table. After the initial shock, he just tried to ignore her, hoping that she would get the hint. Unfortunately, she was extremely persistent and was just annoyed by his lack of response. She started to slowly work her feet up and down his leg, and he stared at the table awkwardly, still trying to pay attention to Elijah. He jumped in his seat and let out a small gasp when her foot suddenly found its way to his groin and she started stroking him with her toes. At this, he could no longer take it. He made a sudden movement out of his chair and gave a quick excuse about not feeling well and needing to head up to his room. He very politely apologized to Elijah and told him that he should expect to see him early the next day. With a quick, and not so polite, nod to Rebekah, he quickly fled the dining room and the hotel.

He immediately felt better when the chilly evening air hit him. At the table, with Rebekah fawning all over him, he had felt suffocated and trapped. Being out on the city street gave him a nice sense of freedom. He had the rest of the night to himself, having nowhere to be and no one to see until the next morning. However, he had never been to Portland before and didn't know where to go or what to do. He decided to just wander around. He knew where his hotel was when he needed to come back, and until then he would just walk until he found something to do.

Damon continued to walk for about a half hour, enjoying the sights and sounds of a different and new city. Portland wasn't like New York, but it was still a city; it was refreshing to be somewhere new and yet still familiar at the same time. Eventually, he came to what looked like a deserted, more run-down part of the city. He thought about turning around, but he decided it wouldn't hurt to continue down a block more. Halfway down the block, he heard loud music coming from a dark doorway across the street. There was a neon sign above the door of a female figure on a pole that was flickering. He knew instantly that it was probably a strip club. He could have, probably should have, turned around and went back to his hotel. After a few moments hesitation, he just decided, 'fuck it' and walked across the street into the club. It was extremely dark inside, and surprisingly the music wasn't hurting his ears. There were a fair amount of men in the club, and he could see about five women up on the bar dancing. Just as he did in his hotel, he took a seat on a stool and ordered a bourbon. When his drink arrived, he took the cold glass in his hands and just started at it. He let out a humorless laugh. I'm in a strip club and I'm staring at my liquor. How pathetic. He looked up at the woman on the pole in front of him and didn't feel anything. She was hot, yeah, but she just looked dirty and desperate. He looked back down at his drink.

The song faded out and in the silence, the girls moved around and switched poles. He didn't look up at the new woman when the music started up again; at this point he kind of just wanted to leave. The woman on the pole was not taking kindly to the fact that this man wanted to ignore her. In an attempt to get his attention, she tapped her white stiletto heel several times against the table right near his hand. He snapped his head up and gave her an annoyed look, one that quickly faded once he actually met her eyes.

She had big, soft chocolate eyes that screamed innocence despite her 'profession'. Her hair was dark brown that hung poker straight against her olive skin. Beautiful didn't even begin to describe this woman; she was absolutely breathtaking. Damon ogled her with his mouth hanging wide open, eyes glued to her. He was finally able to pull his gaze away from her eyes and brought it down the rest of her body. Oh God, her body was magnificent. She was wearing red and white lace lingerie that accented her curves wonderfully. He was so busy staring at her that he didn't even realize she had asked him a question. She tapped her heel against the bar again and looked at him expectantly.

"I- I'm sorry, what did you say?" He actually stuttered. Less than a minute and this woman was already making him crazy.

"I said, how're you doing tonight?" Now it was her turn to look annoyed. Had he not been paying attention to her? She internally scolded herself. Of course he wasn't paying attention to me. He's in a strip club, he's only here to look at me, not give a damn about what I say. She quickly pulled herself together, tonight had been slow and she needed any tips she could get from this guy. He still hadn't answered her question, so she just moved on anyways. "Do you want a private lap dance in the VIP room?" She asked him in the most seductive voice she could manage, and ran her heel down his chest.

Damon was absolutely speechless. He didn't know what he was doing here; he had never been to a strip club before. He never had a reason to; he would always be able to pick up any girl from any bar. He looked at the beautiful woman and could see that she looked kinda desperate, but not in the same way that Rebekah did and not in the same way that the other stripper had either. It was sad, like she didn't want to be here but desperately needed to be. She wasn't desperate for him; she was desperate for his money. He had a sudden strong urge to help this woman, but he was still at a loss for words, so he just nodded his head.

She gracefully slid off the bar and up against his body. She pulled at his shirt collar and led him upstairs to a private room. Just like the rest of the place, it was dark and small. There was a small couch in the corner, a chair in the center of the room, and a small box in front of the chair. "I'm Isobel," she said in a husky voice as she pushed him into a chair. She went to straddle him, but he gently pushed her off and sat her on the box in front of him.

"How about we just talk?"

She looked confused for a moment, and then she came to a realization and said, "You want me to talk dirty so you can get yourself off?" He made a face that was purely disgust and she found herself confused again. She got up and sat on his lap, putting her arms around his neck. She brought her lips to his neck and purred. "What is it you want?"

Damon felt himself harden instantly when she purred against his neck. Determined to stick with his original plan, he grabbed her wrists from around his neck and pulled them down, then he lifted her off of his lap and set her back down on the box. "I want you to sit down, and I just want to talk." His voice was harder than he meant it to be, but trying to do the right thing while being so aroused was making him moody.

"Alright," she said in a soft voice. "I was just trying to- you don't have to be mad at me." She turned her head to hide her face and looked at the ground. She couldn't help the crippling feeling of rejection rush through her body.

Damon looked at her and she suddenly looked so vulnerable and hurt. He immediately felt remorse for using such a harsh tone with her, when she was obviously just doing her job. He reached out his hand to her chin and turned it to face him. "I'm not mad at you." He stared into her eyes for a few moments, and then chuckled. "You're just persistent."

She looked at him nervously for a few moments, and then decided to just be blunt. "Look, I get sixty out of the two fifty you're gonna have to pay for the VIP room." She then hesitated and without looking at him said, "You're not gonna tip me anything?"

He looked at her with sad eyes, something she didn't see since she still hadn't met his gaze, and pulled out his wallet. He handed her three bills, and watched her eyes widen in shock. She finally brought her gaze to his and said, "You're giving me three hundred dollars for nothing? I don't understand." She shook her head slowly. Why would he give her this kind of money for nothing? If anything she had done nothing but annoy him. She hadn't meant to be offensive, that's usually what guys wanted when they came in here.

"Let's just talk, okay?" She looked at him apprehensively, but nodded curtly. "So, Isobel," he paused a moment to think then finished, "is that your real name?" He knew strippers never used their real names, and he knew she definitely didn't look like an Isobel.

Her stomach dropped and she immediately tensed up. She looked away avoiding his stare, and then realized that might be suspicious. Her voice was stuck in her throat; she couldn't speak. Say something, you idiot! Desperate to try and brush off his question, she forced herself to make her voice have some power behind it. "Of course it is."

"Hm." She was lying, but how could he have expected her to be so truthful with a stranger? He sighed and said, "I'm Damon." He locked eyes with her and gave her a flirty smirk. He still wasn't planning on using her for her services, but he could still have some kind of fun with her. And oh boy was it satisfying to see her blush. God, she was so beautiful. "How old are you?"

"What's with the third degree?" Shit! She was extremely nervous. She had worked extremely hard to keep many parts about her identity a secret and she wouldn't have this guy blow it. Sure he was extremely handsome and had icy blue eyes that made her heart skip a beat, but she wouldn't let him ruin everything by figuring her out.

"I told you, I just wanted to talk."

"Yeah, well no offense or anything, Damon, but it's kinda weird that you came to a strip club to talk." She did not understand this man. He practically screamed wealthy, in his designer suit and professional haircut. Sure, he looked miserable, but he clearly wasn't looking to get himself off. So why had he come here?

Damon didn't know how to reply to that, because he knew that it was an odd thing to do. In all honesty, he wouldn't have done it for any of the other strippers downstairs. There was something about this one though, this woman was different. He decided to deflect instead, and called her out on her own deflection. "You didn't answer my question."

She pulled herself together and asked sarcastically, "How old do I look?"

He smirked; she had some definite fire in her that refused to be put out. "Eighteen." Once again, he saw fear in her eyes and he knew that he was close. She definitely didn't look a day over twenty.

"Well, I'm not, I'm twenty one." Shit shit shit! She couldn't have this guy figuring anything else out about her. She knew she looked nervous and everything about her body language was giving her away. What is with this guy? No one else had ever questioned her, not even her boss. All they cared about was that she had a nice body and knew how to rub the men the right way. She knew she had to get it together, and quickly. She stared at him with daggers in her eyes, daring him to keep digging.

Seeing that she obviously didn't want to talk about her youth, Damon grudgingly switched topics. "How long have you lived here?"

She shot up out of her chair and started walking to the other side of the room. "I don't like all these questions." She turned to him and shot him a deadly glare. "Stop asking about me. You want to talk, fine, talk about something else, anything else." He was getting dangerously personal and she hated it.

Damon scoffed, not comprehending just how over the line he had already crossed. "You don't like my questions? Got something to hide?" He said it with sarcasm, but enough curiosity for her to know that he suspected her. The smirk on his face set her off. She suddenly felt like she was being corned and interrogated. She felt adrenaline pulsing through her body at the realization of how close he was getting and she needed to get out of there.

"You don't know me," she hissed. "You don't know anything about me, and I'd like to keep it that way. Respect that."

"You strip in front of men for a living; you don't get to ask me to respect you." He didn't know what made him say it, but as soon as he did he regretted it. She walked up to him and slapped him across the face with more force than he had thought she could manage. He would be lucky if she didn't mark him. She pulled out the three hundred dollars he had given her earlier and shoved the bills roughly in his chest.

She looked at him with cold, hard, angry eyes. "Take your money and leave, asshole. Don't come back here and stay the hell away from me." And with that she turned on her heels and stormed out of the room, leaving him dumbfounded with his hand lightly rubbing his face.


A/N: Okay, so how'd I do? Be entirely honest; be brutally honest if you need to. I take criticism very well and I would absolutely love everyone's feedback. Don't hold back on me! Thank you