Disclaimer: I own nothing.


"Damon!" he distantly heard someone yell out his name. He slowly cracked open an eye and saw his younger brother trespassing on his personal space. Damon inwardly cursed himself for forgetting to lock the door again.

"Ugh, boundaries, Stefan. We've gone over this, waking me up is a sure way of losing an eye or two." Damon groaned and pushed his overbearing brother away. Couldn't a man get a minute or two to himself? He decided to ignore the clock on the wall of his office signaling that he'd indeed been asleep for the past three hours.

"You're right, we have gone over this. You cannot take random naps in the middle of the day! We're also talking about my legacy here, I'm not going to let you ruin what our father worked so hard at creating!" Stefan yelled. He was starting to get to the end of his rope when it came to his older brother's antics.

Damon sighed. He knew this was coming, the grand speech about "their legacy". As the youngest CEO of a multimillion dollar company in the US at 25, Damon Salvatore was both as infamous as he was tired. If it wasn't the press hounding him, it was his little brother yapping righteously in his ear. That boy must have been born with a halo glued on to his head, Damon mused to himself.

Stefan Salvatore, 22, was the second biggest shareholder of Salvatore Inc. after his brother, and they often came to blows over how to handle the family business. Giuseppe Salvatore, their late father, passed the company down to his oldest son as tradition required. This, however, did not please his younger and arguably more competent son.

"Aren't you ever scared that one day you'll really grow wings out of your back and join the rest of the angelic kind upstairs?" Damon smirked.

"If it means you'll be far, far away from me, I'm looking forward to it."

"Ouch, Stefan. That really hurt." Damon shook his head and held his hand up to his heart in mock-dismay.

"Damon, I'm serious." Stefan pleaded with his eyes. He'd grown tired of watching his brother throw away what had been given to him on a silver platter.

"So am I. As a heart attack."

"Please, just tell me what's going on. Don't even try to convince me that something isn't bothering you. I know you. You've always been a dick bordering on psychotic but lately you've really been crossing over more and more to the psychotic." Damon had to look down as his brother went on and on, as he usually did. Despite his annoyance with Stefan, he had to admit his brother was right. Stefan often had a way of understanding Damon's eccentricities like no one else.

Damon glanced at the mirror hanging on the wall behind Stefan. He was a good looking man to say the least. His jawline was sharply defined, as was the rest of his bone structure. His body was lean, looking perfect in crisp black suits which emphasized his arm muscles. Damon's eyes though... They were something else. They were impossibly blue and big, framed by long black lashes. His eyes were what had gotten him most of what he had in this world. Because of his model-like good looks, Stefan couldn't have anticipated what came out of Damon's mouth next.

"I won't judge, I promise. Whatever it is, I'll help you so we can finally get back to business." Stefan said.

"It's been a while." Damon stated simply.

"Come again?"

"What I just said. It's. Been. A. While." Damon gritted out through his teeth. This was awkward enough without his brother playing dumb. Stefan's face lit up as he finally realized what his brother meant.

"Is this a joke? Pardon my French, but you get more ass than a fucking toilet seat at the Grand Central! How could it possibly have "been a while"?" Stefan laughed, his face turning red with glee. This conversation had just given him mocking rights for the next 50 years.

Damon shook his head. It had been a mistake coming to his brother with this. How could Stefan understand? After all, Stefan had been engaged to the socialite Caroline Forbes for over a year now and didn't have a clue of the predicament he was in. Due to his dashing looks, getting dates was easy for Damon. However, moving past dinner without the fear of his dick ending up on the internet was a lot harder. Because of his wealth and position in society, a Damon Salvatore sex tape was worth millions if it existed. Yes, he was paranoid but who could blame him? Especially after her. Damon stopped that thought in its tracks.

"Believe whatever you want. It's just getting a little distracting, that's all." Damon ran a hand through his hair. He wouldn't be coming to his saint of a brother if it wasn't serious. As it was, he hadn't had sex for the past eight months and his left hand was getting tired.

Stefan smiled and casually walked over to the door, closing it. He returned to sit in front of Damon and pulled out his leather wallet. Slowly, he pulled out a business card, handing it to his confused brother. The card simply said "Pleasure" with a cell phone number scribbled under it. Damon rolled his eyes.

"Really, Stefan? Does Blondie know you've been screwing around with hookers?" Damon cocked an eyebrow. Even if they were like water and oil when mixed together, Damon had come to see Caroline as part of his family and wouldn't take his baby brother treating her like crap.

"No! How could you even ask me that?"

"Well when my little brother hands me his pimp's digits, I have a right to ask." Damon said sarcastically.

"First of all, we're not talking about pimps and their hookers here. That's a girl's calling card. She works alone. Second, Tom from accounting gave that to me over 3 years ago, I just forgot about it. You know I'd never do anything like that, especially to Caroline!" Stefan practically yelled out, exasperated.

"And you think I would? That I would actually pay some washed up woman to have sex with me?" Damon asked incredulously.

"You seem desperate enough. Look, you don't even know the best part yet. She's high class. She gets paid for her services, but most of all for keeping her mouth shut. She's bound by a confidentiality agreement to each of her... Clients." Stefan explained.

"You know, I always thought I'd be the one shoving you towards women of questionable morals, Stefan. I think this would be the one time our father would actually smack you over the head." Damon rolled his eyes. This whole situation was surreal. He was getting hooked up through his baby brother.

"Look, this isn't the ideal situation for me either, but I need you focused. If this is the way to do that, then I have to encourage it. Business comes first." Stefan sighed. With that, he got up and left Damon to his thoughts.

Damon looked at the card once more. Was this what he wanted? More importantly, was this what he needed? There was only one way to find out...


As he looked over the New York skyline from his penthouse apartment that night, Damon slowly drank down the remainder of the scotch in his glass. The city always seemed to come alive at night, reminding him of the glass cage separating him from the rest of the young metropolitan population. He hadn't always felt this suffocated. Everything changed once he inherited his father's fortune. Even if Stefan didn't believe him, he had grown up and was trying to act like an adult. Well, as much of an adult as he could possibly be. With that in mind, he sighed and grabbed his prepaid cell phone, punching in the number scribbled on the card.

Damon waited patiently, listening to the phone ring. As it rang for the 6th time, he grew hesitant and moved to hang up, only to hear the telltale click of someone picking up.

"Hello?" He heard a female voice ask, almost hesitantly. Damon almost chuckled to himself, not expecting a prostitute to sound like...That.

"Hello, gorgeous." He answered jokingly in a husky tone.

"Wow. You do realize that the flirting is both ineffective and useless in my case since you're paying me to worship the ground you walk upon?" The girl answered and Damon could almost hear her raise her eyebrows.

"But it did work as an icebreaker, didn't it?" He was answered with a hearty laugh on the other end. He smiled to himself. It was actually kind of fun to talk to someone, without any of the normal pressure of being Damon Salvatore.

"I guess so. I'm just not used to smart asses calling me up that casually."

"I can assure you that while I am very smart, my ass is best described as delicious rather than smart." Damon smirked. He liked this girl already. She had, what was the word...Spunk.

"Again with the flirting. Almost makes me wonder if you dialed the wrong number, my friend. So why is it that a heartbreaker like yourself is calling me?" She asked. Damon had to give her credit, she seemed smarter than what he'd expected.

"Isn't it obvious?" He had to roll his eyes.

"Actually, it isn't. Are you a virgin?"

"No!" His eyes popped out comically at the question. He'd bedded quite a few ladies before his descent into an eccentric, paranoid millionaire.

"Are you somehow deformed?" He could hear her holding back a laugh on the other end.

"Oh baby. You haven't seen me, but I can tell you that I truly am a sight for sore eyes." He shook his head and smiled to himself. This girl would have to be blind in order to not appreciate his packaging.

"Well you're a tough one to figure out. Why don't you meet me tomorrow at 8 at the Palace Hotel Lobby Bar. We'll figure it out from there."

"How will I recognize you?" He asked.

"I'm gonna be wearing a blue, strapless dress. You're not gonna miss me." She explained.

"Wait! Aren't you the least bit curious to know who I am?" He questioned.

"I'll find out soon enough. And why should your name matter? You're just like anyone else, even if you don't believe it." Something constricted in his throat at that. This girl seemed to have him pegged down after only 2 minutes of talking. He started to wonder what she could accomplish when given more, a lot more, time.

"Fair enough." He said, unsure of what to say, a first during the conversation.

"See you tomorrow!"

"I'm going to rock your world." He grinned, remembering he'd never had any complaints before.

"Oh no, cocky. That's my job." He heard the click and knew she had hung up on him.

Damon had to laugh. Regardless of the outcome, this was going to be fun and he was going to enjoy the ride. Literally.


This idea has been bugging me for so long. Honestly, I can already see the main plot but this is written pretty much for my own amusement. I knew that I wouldn't get any peace of mind before I actually wrote it, so hopefully someone likes it. The second chapter is Damon meeting Elena and a lot of things are going to be explained in it. I'm a rookie writer, I repeat, this is for my own amusement. And for those of you who are as nuts as I am!