Disclaimer: I do not own Vampire Diaries, however consider this story mine. Any dialogues not canon from the show as well as any descriptive sentences are the end result of over twenty years of writing. I have poured my heart and soul into every beautiful paragraph, every perfect sentence, every hot and/or romantic scene, and every funny one-liner. To copy this work or any other and claim as one's own, in whole or in part is a criminal offence punishable by ostracism, harassment by my loyal readers, and possibly even dismissal by the MODs. It's not worth it; don't be a thief :)

Prologue

Dear Diary,

I still can't believe it's been six months since Stefan and I moved in together! We've pretty much had this gorgeous colonial boarding house all to ourselves and it's been amazing. Well, I will admit that I do get a little bit lonely sometimes in this big house; Stefan's been working most nights at the hospital while taking classes during the day. He's so determined to be a doctor and follow in the footsteps of his father, who passed away when he was seventeen. Because it was his dying wish, I don't really have the heart to tell my boyfriend that his career choice isn't exactly the best option for him; Stefan is sort of squeamish around blood, you see. Still, he's working so hard to get over his phobia, and as his long-term girlfriend I guess I have to support him in this. Still, I feel like I'm spending more time alone with my thoughts lately and less time with him, and to be honest I'm going a little stir crazy. I'm almost tempted to leap off this straight and narrow path I've been treading the past few years, (ever since my senior year of high school, actually). But the problem is that I'm a little scared to let loose, because that sort of behavior has gotten me into trouble in the past. Fortunately, Stefan has no idea, and I'd prefer to keep it that way; he doesn't need to know that his perfectly angelic girlfriend used to be a wild child. Honestly, he'd probably freak out on me if he knew the sorts of things I used to do for fun, which is one of the reasons he's so good for me. I'm far less likely to resort back to my self-destructive patterns as long as I have him in my life; he'll be the perfect husband for me, I just know it…

Elena Gilbert was curled up in the corner of the plush leather sofa, enjoying the cozy warmth of the fireplace and taking full advantage of her time alone. As usual on a Friday afternoon, Stefan was in class and would be for several hours; at which point he would then come home for about an hour to shower and dress for his shift at the hospital. Elena was also a student at the university, but she was majoring in Professional Writing; it wasn't as glamorous or exciting as it seemed. When her mother Isobel had first pushed her into it, she'd insisted Elena would find it far more lucrative than her aspirations to become a first-rate novelist.

"You're not going to be able to support yourself by selling a bunch of fictional stories," she'd pointed out after Elena had expressed her desire to study creative writing her first year of college. So while she was severely disappointed, she'd agreed to take the classes her mother had suggested and save the creative expression for her diary. That had been two years ago, and while her grades were decent enough that she could scrape by each semester without landing on academic probation, she might as well be failing. Today she had simply decided to take the afternoon off; she had to write yet another boring document for her Business Writing class and it was due first thing Monday morning. She had barely started on it and couldn't seem to find any motivation to work on any of her other assignments either; more than likely she would be scrambling at the eleventh hour (again) to complete everything and scrape by with another C.

She sighed to herself and started scribbling again, lost in another train of thought.

I'm pretty sure Isobel would flip out on me if she knew this, but sometimes I almost wish Stefan and I were already married and that he was a successful doctor. I know, it's not exactly feminist of me to think, but the truth is I often wonder if it would be so wrong to just let him earn the income so I can quit school. Obviously I'm not going to do that; My birth parents and Aunt Jenna would kill me, and I'm pretty sure my Aunt Miranda and Uncle Grayson (god, it's so weird not calling them Mom and Dad anymore) would turn over in their graves if they knew. I wish they were still alive; maybe they could have paid for my tuition instead, and then Isobel would have just had to deal with it when I chose to study Creative Writing. Maybe if they had been, then I wouldn't be practically failing every single course right now; maybe I might even be on the honor roll and get some sort of Best Author award or something. Well, it's not like I can change what happened that night, no matter how badly I wish I could take it back. The reality is, I can't afford school on my own, so John and Isobel are pretty much the ones who get to decide what classes I get to take since they're the ones paying my tuition. And I know it's awful, but sometimes I wish they'd never told me the truth; that I was adopted by Grayson and Miranda Gilbert, John's older brother and sister-in-law. I didn't find out until I was almost eighteen, and by that time the accident had already happened. It didn't help that the man I had been led to believe was my uncle happened to be a complete jerk all my life, and I'd never really liked him. And as for Isobel, well she just sort of showed up one day and decided she'd try to give this whole "mother" thing another shot; must have been so much easier for her now that she didn't have to actually raise me herself. Anyway, to say I'm not close to my birth parents would be a huge understatement. In truth, the only family I actually am close to are Miranda's younger sister, Aunt Jenna, and my cousin Jeremy, who I'd grown up thinking was my younger brother. Yeah, my life is definitely complicated.

Anyway, back to Stefan…I can't really explain how I know this, but I just have this feeling he's going to ask me to marry him. I mean, why wouldn't he? We've been dating for just over a year, and obviously we're compatible b/c we're doing really well with the whole "living together" aspect of things. So you know, it wouldn't really be such a big deal if we just made it official, since there's really not much of a difference. Besides, "Mrs. Salvatore" has a really nice ring to it, pun not intended. I wonder if he'll buy me a ring, or if I'll get a family ring instead. Apparently Stefan's family line goes way back to the founders of Mystic Falls, just like mine, so I might just get a priceless family heirloom like my mom got from my dad. Of course they had to re-set the stones, but still, it would be nice to have a piece of history. I never got Mom's ring, since she wanted Jeremy to give it to his future wife someday; makes sense, I guess. I wouldn't really be able to wear it, after all, since it is a wedding ring…oh, that sounds like Stefan's at the door. We'll talk later!

Elena turned her head at the sound of the key sliding into the lock. She really hadn't expected Stefan to be home yet; it wasn't even two o'clock. Still, if he was going to be home for a few hours before his shift, she would definitely take advantage of the opportunity. She immediately closed her diary and set it aside before pulling off her shirt to reveal her lacy blue bra and fluffing up her hair for good measure. She raced to greet him at the door; she couldn't wait to surprise him since he likely wouldn't be expecting to have an afternoon quickie in the living room. To say she was shocked when a stranger stepped through the doors instead would be an understatement.

The first thing she noticed was that he was ridiculously hot, with dark hair that fell slightly into his eyes, and rippling muscles beneath a tight black tee shirt and dark jeans; her "aunt" Jenna would have been all over him if she were here. For a moment, Elena even forgot that she was standing in just her bra and a pair of yoga pants in front of a complete stranger, and she wasn't even aware that she was blatantly checking him out; it took the saucy smirk on his face and the sudden movement of his piercing blue eyes as they settled on her breasts for her to snap out of it and remember her modesty and the fact that he had just walked into the house uninvited.

"Who are you and what do you think you're doing here?" she demanded, crossing her arms over her chest and trying to look intimidating.

The intruder smirked, as if she amused him. "Technically, I should be asking what you're doing here, though I can't say I mind so much considering how you've chosen to greet me."

She glared at him; she really didn't like his attitude, and she had half a mind to slap that infuriating smirk off his face.

"I wasn't expecting you to walk through the door," she said indignantly. "I thought I was greeting my boyfriend!"

"Oh, you must be Elena," he said knowingly. He seemed to be even more amused by the situation now; she was beginning to get annoyed, since he'd still not explained what the hell he was doing in her house.

"I'm Damon, Stefan's brother," he explained. Upon seeing her quizzical expression he frowned slightly. "He didn't mention I would be coming here." She could tell it was a statement, not a question. Clearly, Damon had an overinflated sense of self-importance.

"Maybe you should have…oh I don't know…called ahead before you decided to break into your brother's home?" she said, her smile was sarcastically sweet.

"I didn't break in, Elena, I have a key," he dangled them in front of her, rolling his eyes as if she'd said something incredibly stupid.

"All the same, why would you just show up uninvited?" she demanded.

Damon sighed in exasperation. "I don't need an invitation," he was talking to her in a tone that made it seem like he was explaining something to a small child. "I live here."

"Since when?" she arched her brow suspiciously. Stefan had never mentioned his older brother when he'd asked her to move in with him; she'd assumed he was the only one still living at the Salvatore boarding house. Obviously, her boyfriend had left out a few important details concerning the living arrangement.

"Since always," he quipped in a smart-ass tone. "Or did my baby brother forget to mention that part of the rental agreement?"

"Must have slipped his mind," Elena snapped. "It would seem it's genetic, considering I've been here pretty much every day for the past six months and have never seen you once in all that time!"

He shrugged. "I've been travelling," he explained. "But I got bored, so I decided I'd come home for a while; see what the ladies of Mystic Falls have been up to."

"I doubt they missed your absence," she said, rolling her eyes at his arrogance.

"Actually, Elena, I happen to have quite a string of admirers; you might even know a few of them." He smirked again, laughing at his private little joke; his eyes lit up with sardonic amusement. "So you might want to be a little nicer to me, considering you're a guest in my house."

She tilted her head up, staring into his eyes defiantly. "I'm not a guest," she informed him. "I live here."

"I know," he said, shrugging his shoulders as if it didn't make a difference to him. "But considering that it's my house, and I wasn't consulted when my baby brother decided to have you shack up with him, technically I'm the one who ultimately gets to decide who lives here."

"You can't just throw me out," she said, eyes burning into his in challenge. "Stefan wouldn't stand for it."

"Stefan isn't the one who pays the bills around here," Damon said, his expression suddenly serious, if not a little dangerous. "So you might want to re-think your whole plan to have my saintly brother come to your aid, because I have no trouble tossing his free-loading ass out the door."

Elena fought back the choice words she wanted to call him; something in his tone told her he meant every word of what he said. The last thing she wanted was to get Stefan kicked out of his home, and she wasn't exactly thrilled about the very real possibility of having to move back into the dorm, or worse yet, live with Isobel. It was bad enough that she was forced to spend time with her birth mother once a week for the sake of her helping with school and living expenses. Otherwise Elena would really be failing, as a job would severely cut into the time she needed to work on her assignments.

Damon took her silence as a sign that she was finally going to comply with his demands and smirked in triumph. "I thought so," he said simply. "Well, now that we've gotten that whole issue out of the way, we should start over. I'm Damon, Stefan's brother." he smiled, holding out his hand.

"Elena," she sighed, holding out her hand and trying to be as civil as was humanly possible. Seriously, did he ever stop smirking?

Instead of shaking her hand as she'd expected, however, he took it gently in his and raised it up to his lips in an old-world gesture that made her legs turn to jelly. "A pleasure to meet you, Elena," he purred seductively. "I can see why my brother is so smitten."

She was a little unnerved by the jolt she felt at the soft brush of his lips against her skin and the way his eyes seemed to pierce her soul. She found herself smiling and blushing slightly, in spite of her better judgment; she had to admit, he was quite charming when he wasn't being an ass.

Damon obviously knew he had such an effect on her, because he was smirking again as he released her hand. "Well, I should probably go get my stuff from the car and let you get back to what you were doing," he said, breaking whatever spell he'd somehow cast over her the second he'd taken her hand in his. She licked her lips nervously, still feeling a little dazed.

"Oh, right," she said, her words sounding a little more breathy than she would have liked. "I guess you want to get settled in, and you'll probably want to shower too. You can use my…I mean, Stefan's bathroom if you like. I can show you where it is."

Damon couldn't help but laugh softly in amusement; he hadn't realized she'd be so easy to fluster. It was cute. "I have my own private suite," he said, reminding her once again that he lived there. "Unless that was an invitation…" he winked.

She flushed to the roots of her hair and shook her head. "No!" she said, scandalized that he would have the audacity to suggest such a thing.

Damon smirked again; he had a feeling this little arrangement could be fun for him. "I was teasing," he assured her. "You're going to have to learn to lighten up, especially if we're going to be roomies."

"I'll work on that," she said, willing her heart to stop pounding so hard in her chest. His playful smile and expressive eyes were disarming; she would definitely have to keep her guard up around him. She watched as he moved back to the door; she couldn't help admiring the sculpted backside, thinking that his fitted black jeans should be illegal. It really didn't seem fair to her that Stefan's older brother happened to be so incredibly good-looking, and it was so obvious that he was the total embodiment of the Bad Boy; a woman's greatest weakness. She knew she would have to be extremely careful not to give in to the temptation to sample such a forbidden fruit, no matter how enticing; she was dating his brother, after all. No good could possibly come from developing a crush on Damon Salvatore, she told herself.

"Oh, and Elena?" he said, snapping her out of her thoughts before they went down a very dangerous path. He cocked his head to one side, winking over his shoulder at her. "Don't feel like you have to stop lounging around in your underwear on my account; I know I won't."

Another jolt went through her at his suggestive comment and a dull ache started up between her thighs. She stared after his retreating form in stunned shock; oh yeah, she was definitely in trouble.

Author's Note: First of all, I wanted to thank everyone who left so many awesome reviews for all my stories, but especially my "Restless Nights" series, and "All I Need". Seriously, you guys make the hours I spend writing (and re-writing) worth it; I really wouldn't be here without your continued support!

Now, down to business! I sort of came up with this story after writing the final chapter of "Restless Nights" during the scene where Elena wonders if Damon was a stripper. It sort of got me thinking, and a certain image popped into my head. I won't give away the ending, since I haven't even gotten around to writing that part yet (just the outline), but basically the premise is that Damon has a little side business entertaining the ladies of Mystic Falls at private parties. And well, let's just say one of Elena's close friends decides to hire him for a bachelorette party and…I'm sure you have an idea of where I'm going with this ;)

Anyway, once I got that scene in my head, I started filling in the back story and realized I had come up with a story that just had to be written, despite the fact that I'm still working on "All I Need", which isn't even halfway finished yet. But you know how it is; when the muse wants something, it's impossible to focus on anything else.

Back to this story, there are a few things I want to clarify regarding plot:

I've aged the characters a bit. Elena, Stefan, and pretty much all her friends are 22. Damon is 25.

This is (obviously) a Delena story, so there's going to be a bit of Stefan bashing by certain characters (mainly Damon and Isobel). Also, Delena-shippers can release that breath they've been holding because I have no intentions of actually subjecting anyone to a Stelena love-fest. I can't handle watchingthem making out onscreen, so it's safe to say I wouldn't be able to stomach actually writing a love scene…*chokes on bile at the mere thought of doing so*

John and Isobel are Elena's birth parents, but did not raise her. John allowed her to spend her senior year living with Jenna, but only because his business dealings made it nearly impossible for him to actually have time to raise her and his nephew Jeremy after his brother and sister-in-law died in the car crash. In this version, however, it was a car accident involving a drunk driver, and they didn't go off the bridge; it was the impact that killed them. Elena was in the back seat, so she was pretty banged up and knocked unconscious, but she survived.

Elena does have a trust fund, but cannot access it until she's 25. In the meantime, John has control of it and basically this means she is at the mercy of both him and Isobel, who still has influence over his decisions regarding their biological daughter. She moved in with Stefan, against Isobel's wishes, in order to regain some sense of control over her own life.

If you have any questions regarding something in this story, just let me know and I'll answer them in the next chapter! Can't wait to hear what you all think!

~Carly