AN: Hi everyone! Sorry this story and my other one have been on an unplanned hiatus. I've just had so much going on, and to be honest I've had most of this chapter written for weeks, before I got an awful case of writers block. If you're subscribed to me, you might have noticed I've written a couple one shots, and it's because writing other things sort of helps me with writers block but woah! this one was bad. Anyway, I'm so happy for all the reviews and anyone who's read my story and took the time to let me know what you thought! I appreciate it. And if there's still anyone out there who remembers this story, I really hope you enjoy this chapter. XOXO

Disclaimer: I own none of the characters.

Damon watched as her eyes lit up the moment he slipped through the small crack of the door. He hadn't wanted to wake her but to his surprise he found her wide awake the moment he walked in. Grabbing a chair, he sat right besides her staring down at her lovingly.

"Good Morning." He whispered, taking her tiny fragile hand in his large ones. The nurses informed him that she'd been having a tough week, tougher than usual, and he'd made it his mission to make her laugh every morning before he headed out to work. Especially since he'd Her warm smile melted his heart and he squeezed her hand affectionately.

"How's my boy?" she cooed her hand slowly reaching to cup his face in her palm. "You're all dressed up, aren't you late for school sweetheart?" she took notice of his attire.

"Don't you worry about that," he smiled sadly. "I wanted to make sure you were okay first." Damon felt the pang of hurt in his chest at her words; if it wasn't obvious before, it clearly wasn't a good morning for her.

"Don't forget to hold your brother's hand when you're crossing the street." She told him. "Where is he anyway?" Damon's heart shattered into pieces, as her eyes wandered around the room for Stefan. He never hated his brother more than in that moment, but he was almost grateful that she couldn't remember that it'd been almost a year since she'd last seen Stefan.

"He's probably in the bathroom sculpting his hair." He managed to hide his anger enough to reassure her. She let out a genuine laugh that almost made him forget how much he despised both his brother and father, but not quite. Under their father's influence Stefan managed to completely abandon their mother in this most vulnerable time. He couldn't understand how his brother and father could be so cruel. The woman lying in the bed beside him devoted her entire life to them, he couldn't have asked for a better mother. She was the sweetest and most nurturing woman in the world, always level headed and sometimes too nice for her own good.

As little boys he and Stefan had her wrapped around their little fingers, all it took some begging and pleading eyes, and it was impossible for her to deny them anything. She lived to see her boys happy, and it pained him to see her slowly slipping away from him. He loved his mother more than he ever loved any woman in his life, in fact she might've been the only woman he's ever loved at all.

There was no doubt that Giuseppe was holding something over Stefan's head, but Damon made no excuses for Stefan. He held Stefan completely responsible for his choices no matter how much of a monster Giuseppe proved to be. Stefan was a full grown adult who could make his own decisions, and he let fear and his desire to live up to their father's expectations control his life.

"You should get going sweetie, you're already late." She squeezed his hand gently before letting go.

"Are you sure you're okay, I can take the day off if you need." His hand gently ran through the long raven strands of her hair that almost matched his own. He felt guilty knowing he it'd be a week before she'd see him again. As much as he hated it, work sometimes took him away from her longer than he wanted, but he'd always bring her back a gift or souvenir from his trips and it always made her smile.

"I'm fine Damon, now go on." She reassured him with another warm smile.

He fluffed her pillows and pressed a gentle kiss to her forehead before reluctantly exiting her room.

Elena sat impatiently at her desk, her eyes glued to the ticking clock as she waited for her boss to appear. She sighed frustratingly as she recalled he'd been late every morning that week, but Damon wasn't usually one for being punctual.

Surprisingly enough they actually managed to find a comfortable rhythm and worked well with each other. Even though the tension lingered thickly in the air, she was beginning to realize that Damon was a pretty good teacher after all, over the weeks she learned more from him than she ever expected to. His inappropriate 'jokes' seemed like a small price to pay for the knowledge she was gaining under his tutelage. She'd never admit it out loud but she didn't mind it much anyway.

After all it's not like he was all to blame, she hated how her body instantly responded whenever he was in close proximity, the way her breath hitched, the tiny electric shocks that buzzed through her whenever they 'accidently' touched. Earlier that week he placed a hand at the small of her back while demonstrating some new software and she practically hyperventilated, only managing to catch her breath after his hand slid agonizingly slow off her back.

Thankfully he didn't seem to notice her discomfort or at least she hoped, but Damon was a cocky and arrogant man, he walked around the entire building fully aware that he could have any woman he wanted. Sadly it was true, given the number of women that came strutting into his office during the day, desperate for his attention. Elena would listen intently as she pretended to be occupied with her assignments while he showered them with compliments, undoubtedly making them feel like the most beautiful thing in the world.

Elena could never understand why it bothered her so much, she tried to tell herself that it was the lack of professionalism that annoyed her and not the image of her boss flirting with Nancy from the copy room, but deep down she knew better even if she'd never admit it.

God she was pathetic. So what if he called her pretty? Was she really that desperate because he threw a lousy compliment at her? He was an asshole, which she already established. Why did it matter what he thought of her?

He came strolling into the room forty minutes late wearing his bright charismatic smile, his raven strands unruly as ever, in a finely tailored suit that flattered his muscular frame, and immediately she was taken out of her thoughts. He made his way towards his desk sliding a white envelope to her without uttering a word.

She looked at him puzzled before slowly reaching for it. Inside was an invitation. Her eye brows furrowed at him as her confusion increased.

"I usually take Ric but since he's got something to do next week, you're going." He wasn't asking, he was telling her. She fought the urge to roll her eyes at him but whatever it was, if it was work related she had no choice but to oblige.

"Is it just us?" she questioned her heart racing as she read the invitation. It was some week long Conference in Las Vegas and she desperately hoped that she wouldn't have to spend all that time away with him.

As if he could sense her apprehension, he tilted his head to the side. "It's just us, is that a problem?"

"No…no… It's fine."Elena shook her head vigorously. The other interns would die for this opportunity and she'd be a fool to pass it up. It was just Damon, she hated his guts (or so she desperately tried to remind herself). There was no reason why her stomach should be all tied up in knots over the idea of going away with him for a whole week, to Sin City of all places. Elena didn't even want to think about the temptations that awaited them there, being closed off in Damon's office with him 8 hours out of the day, was all the temptation she could handle.

She only had the weekend to prepare for this trip that he randomly sprang on her, she didn't know if she could ever prepare enough for it. Nothing would make her less anxious about spending a week alone with Damon.

"Good." He smirked. "It's all expenses paid, Rose should have your ticket and hotel reservations by the end of the day."

"Thanks." She supplied awkwardly, not knowing how else to respond.

"You earned it." He smiled at her. It almost looked genuine, but she knew better than to think he was capable of seeing anyone else as competent other than himself and at times Alaric.

What'd I ever do to deserve that? She thought quietly. Rebekah was going to have a field day with this.

It was well after five o'clock by the time they arrived at their hotel. The plane ride was much too short for the amount of money that was spent on their first class tickets. Damon had a car waiting for them as soon as they checked out of security. Elena barely got used to the luxury of the flight, before they pulled up to the Forbes Hotel, probably the classiest and most luxurious hotel in the entire country, maybe even the world? She had no idea. It's not like she frequented these kinds of places.

When Damon said the company would be handling all her traveling expenses, she assumed she'd be staying in some dirt cheap motel, flying coach and if she was lucky she'd get a seat right next to a wailing baby. She never expected that he would spend so much money to bring her along on this trip, not to mention he practically scolded her for attempting to pick up her own bag, insisting that someone else would get them for her and take carry them up to her room.

She knew he had to be well off, just with the knowledge that he was part owner of one of the biggest architectural firms in the entire country it was fairly obvious. Then of course there was the car or rather the cars she'd seen him drive to work, but being here in this lavish establishment she had a better idea just how well off he was.

Just after they checked in at the front desk, she heard a loud squeal and a blonde woman almost knocked Damon down as she ran up to wrap him in a big hug. Not that it was surprising.

"I was beginning to worry that you wouldn't come this year." The blond commented before loosening her grip on him.

"What? You thought I'd let your little boyfriend scare me off?" He smirked.

"Oh I know better to expect you to be scared of anyone." She replied. "I'm just glad you're here, where'd you meet this lucky girl in the lobby? And where's Ric?" The blond looked disapprovingly in Elena's direction.

"This is Elena, our new intern." Damon replied smoothly. "Elena this is Caroline Forbes, she owns the bakery down the street, and her father owns this hotel and many others like it."

"Oh my god I'm so sorry," Caroline apologized in embarrassment, her faced turned a bright shade of red. "I thought you were one of his… god I'm so sorry you probably think I'm a bitch."

Elena laughed it off holding her hand out to shake Caroline's. "It's okay I'm Elena, it's nice to meet you."

Elena couldn't believe she was standing in front of William Forbe's daughter; he was one of the richest men in the world, owning a chain of hotels among other things.

Caroline reminded her of a doll, her blond hair bounced with perfect curls, her eyes almost as blue as Damon's. She wore a short pink dress with matching sandals, perfectly manicured nails and her sunglasses sat on top of her head.

"Oh yay, you don't hate me!" Caroline squealed excitedly.

Elena couldn't help but laugh at her excitement. Caroline reminded her of Rebekah a bit, but similarities stopped at their appearance. Other than that she could tell they were polar opposites.

"It'll be nice to have another girl around this year; usually I get stuck with this one and the other one." She said pointing in Damon's direction.

"You love us." Damon replied before excusing himself so he could take an important call.

Once he was out of ear shot, Caroline smiled knowingly at Elena. "So you're his intern huh?"

"Yeah I've been working there a while now, I'm sorry I never got a chance to make it to your bakery." Elena replied looking around nervously.

"Never mind the bakery; you must be some kind of intern if Damon's flying you out here instead of Alaric." Caroline got right to the point, smiling as if she knew something that Elena didn't.

No, uh actually Alaric was busy this week and since I've been working closely with Damon, he thought—"

"Wait you've been working closely with Damon? Damon Salvatore?" She interrupted. "Now Elena, I'm going to ask you a serious question and please don't be offended but are you sleeping with him?"

"Oh god no, he's my boss!"

Caroline could see how horrified she looked and quickly deduce that she was being honest.

"Again I'm so sorry, I'm really not trying to be a bitch, but this whole situation is just hard for me wrap my head around. It's just…. I can't understand why Damon would be working so closely with you, one of his interns without sleeping with you. It goes against everything I know about that man."

"If it makes you feel any better, I'm aware that Damon is a bit of a—I know he gets around with the ladies." Elena said, "But our relationship is strictly professional I assure you, he barely tolerates me."

"The fact that Damon flew you out here to this place tells me that he more than tolerates you, business trip or not. Sweetie, don't be so naïve."

"I think you might be reading too much into it." Elena answered.

The last thing she wanted to do was fill her mind with silly ideas of Damon having feelings for her. He was her boss; a man who could probably have any woman he wanted, everything Caroline insinuated seemed so completely far-fetched when she kept everything else in mind.

"I was with the man for over a year Elena. There are some things that I just know. There are only two reasons Damon would ever be alone with any woman, either he wants to sleep with you, or he wants to get to know you. And since he spent all this money to get you out here for this 'conference', I'd say it's the latter."

"Wait. You and Damon were a thing?" Elena's curiosity was peaked and immediately she connected the dots. Caroline must have been the girl he was referred to previously.

"Yeah we crashed and burned." Caroline explained casually.

"Oh. Sorry about that."

"Nothing to be sorry about, Damon and I were awful together. Really we were just a mess, but we're really great friends now so I guess it all worked out."

"Well I'm glad then." Elena smiled. Despite barely knowing Caroline, the blond seemed really comfortable sharing the details of her life, but she wasn't so sure Damon would appreciate it. He didn't have a single picture frame in his office, and she knew almost nothing about his personal life.

"Now back to you Miss Intern, what are you going to do about your boss having the hots for you?"

"He does not." Elena objected her cheeks burned and she didn't need a mirror to know that they were bright red.

"He brought you here with him, didn't he? And you're an intern; Damon hates interns, if you hadn't noticed. Except you." Caroline teased.

Almost immediately realization began to sink in and Elena began to panic. Her apprehension must've been written all over her face because right away Caroline gave her shoulder a comforting squeeze. "Don't worry; I'll get to the bottom of this."

"God, I can't believe how stupid I was." Of course she'd be beyond flattered if Damon actually felt anything at all for her, which part of her still doubted. But she couldn't help feeling disappointed that all her hard work had been in vain and Damon hadn't even recognized her talents at all. Above all else she wanted him to take her seriously for her work. She'd work her butt off to get that internship and she wasn't about to throw it away just because her boss couldn't control his hormones.

"You're not stupid. Damon can be really convincing when he's trying to hide how he feels." Caroline reassured her. "It's just the way he's always been."

"Can we just forget about it?" Elena asked, she had no proof of any of Caroline's suspicions, and she didn't want to make a bigger deal of it.

"If you say so, I just wanted to give you a heads up." Caroline conceded. "But how about we meet up later, there's a bar somewhere in this place maybe we could hang out later on tonight if you're not working that is."

Elena didn't miss innuendo in her statement, but she chose to ignore Caroline's teasing at the moment. "I'll have to check with Damon, but I'd love to."

The girls exchanged information and Elena made her way up to her room. Her mouth fell open as soon as she pushed the door open. The room was gigantic; it looked like something that belonged in a palace. There were bold gold accents everywhere; smooth silk sheets covered the bed, and the most beautiful view of a city that she'd ever seen.

She put her purse down and fell back against the humungous bed in exhaustion. Even though it was a relatively short plane ride, her talk with Caroline was still heavy on her mind. She'd been so distracted that she hadn't even realized that her luggage had made its way to her room.

After getting her schedule from Damon, she decided she'd need a long hot bath before heading out with Caroline later that night. Yet she'd only been soaking for a few moments before she could hear knocking and soon after Caroline's voice outside her room door.

"Elena!"

She quickly slipped on one of the plush white robes before running to answer it. The bubbly blonde smiled before inviting herself inside.

"I thought we could leave early, I hear the bar gets crowded." She urged.

"Yeah, I'll get dressed." Elena didn't have many girlfriends outside of Rebekah, and Caroline seemed like a nice enough person, but somehow she still felt a little bit uneasy about going out to a bar with her. Caroline seemed like a typical social butterfly and the type that wouldn't take no for an answer when she set her mind at doing something.

"I figured we could get some drinks, talk to some guys, then drink some more. You know the usual." Caroline winked in her direction. "Put on something sexy."

"Why do you care about meeting men, didn't Damon say you had a boyfriend?" Elena asked.

"Well not for me, for you silly. I thought it'd be good if you wanted to keep your relationship with Damon professional, you'd want to meet someone else."

Elena couldn't argue with her logic, but it's not like she's had much luck in that department, the last time she tried it didn't go so well and she wasn't sure if she was ready to put herself out there after such a massive rejection.

"And by the way I'm not rich; my father is; in case you were wondering." Caroline randomly announced. "I make my own living."

"I'm impressed." Elena admitted. She thought she had Caroline completely pegged, but the blond managed to surprise her.

"What? Did you think I was a spoiled daddy's girl?" Caroline smiled. "Would I be working at a bakery if I was?"

"I guess not but you'd probably still inherit your dad's fortune right?"

"Absolutely. But I still like to provide for myself. My dad didn't always understand it, but he's more accepting of it now."

She was amazed by Caroline's independence. "That's incredible. Not many people would be able to do that you know?"

"Having that kind of money is really not all it's cracked up to be. Believe me." Caroline replied, a tiny frown appearing on her face before quickly vanishing.

"Now come one let's get you dressed, where's your clothes?"

By the time she'd gotten ready and out the door, her back was exposed, and the hem of her dress fell midway to her thighs, exposing her long tanned legs. She hadn't even remembered packing that dress, but she knew instantly that Rebekah had something to do with it ending up in her suitcase.

He'd been sitting at the bar almost as soon as he arrived, right after another heated argument with his younger brother, only a glass of bourbon could take the edge off. Almost three days before he'd left a very colorful message on Stefan's voicemail after visiting their mother at the nursing home. It had taken his brother days to even return the phone call; if Damon needed any more convincing of how little Stefan cared, that would have been it.

They hadn't resolved much, there was a lot of shouting, accusations being thrown around on both sides, some swearing and finally Damon heard the dial tone, signaling that Stefan had hung up on him. He swore that even though Stefan didn't know it, his brother had just hung up on any possibility of them ever being brothers again.

He was on his third glass of bourbon by the time Caroline and Elena showed up and took a seat beside him at the bar. His eyes were immediately drawn to Elena and her short red dress. As if he didn't have enough of her unintentionally teasing him at the office, he sight of her in that dress suddenly made sitting down painfully uncomfortable.

"What a surprise?" Caroline said sarcastically. Elena shot him a small wave before ordering their drinks.

"I see you've already kidnapped my intern."

"Couldn't let a pretty girl like that sit in her room all night, especially with all these men just waiting to show her a good time." Caroline gestured towards the crowd.

"Yeah, you just be careful with her alright?" It wasn't quite a whisper but it was low enough that Elena couldn't hear.

"Oh. If I didn't know any better, I'd think you cared about her Damon." Caroline whispered in amusement.

"Good thing you know better then. Huh?" He smirked before taking another large sip of bourbon.

Caroline rolled her eyes before grabbing Elena and their drinks and leading her to the dance floor.

Of course he spent the rest of the night watching them, well her. She spent the majority of the night talking to this one guy who seemed really interested in everything she was saying. Yeah right. He thought. He'd been that guy before and that guy only wanted one thing.

Nonetheless, she was laughing, smiling and more carefree than he'd ever seen her. Suddenly the most unpleasant feeling washed over him in waves and settled deep in the pit of his stomach, jealousy? He wasn't sure. He knew one thing however; she never smiled like that with him and for some reason that bothered him more than he cared to admit. This random stranger comes along and manages to make her giggle like a school girl, meanwhile the only reaction he's managed to elicit from her was this awkward tension.

He downed the last sip of his bourbon, suddenly very aware of the weird possessive thoughts running through his head. He had no right to feel jealous, he and Elena weren't dating, hell he barely tolerated her stuck up, micromanaging ways. Why should it matter to him who she dates or the fact that the only time he got to see such a beautiful side of her is when she's with another man?

Nope. None of these things should matter to him. He decides, he's got enough baggage as it is. It's one thing to lust after her at the office, but he didn't plan to let himself get emotionally involved—at least not more than he already was.

Damon was about to get up from the bar and trudge miserably to his room, when he notices the random guy press a gentle kiss to the back of her hand. She smiled at him blushing before slowly walking away as if she didn't want the night to end.

Damon almost felt sick watching them, Elena was clearly smitten by this fool, whoever he was, and he couldn't help but make comparisons. Sure the guy was decent looking, maybe rich considering the hotel, but it still didn't excuse the tacky green dress shirt he wore, or the cheesy hairdo that reminded him of something Stefan would sport. He couldn't see why Elena would be enamored by this guy of all people, he hardly seemed like competition.

"Goodnight, Damon?" He heard her whisper as she walked passed him, effectively pulling him out of his petty thoughts.

"You seemed like you had a good night." He blurted before he could process the words that spilled from his lips.

He could still see the ghost of a smile on her lips, "Yeah I did." She responded before walking away and leaving him standing by the bar.

Thanks for reading guys. Let me know what you think! :)