"You guys go ahead, I'll meet you inside in a few minutes" I tell Stefan and Caroline once we've reached the bar

"Why, what's up?" Stefan asks

"I uh, I invited someone to meet me here, so I'm just gonna wait for them out here" I shrug

"You invited someone?" he moves closer and drops his voice to a whisper "Is it coffee shop girl?" he asks

"She has a name…" I correct him

"I know, but I'm not privy to that information so for now, she's nickname girl"

"Who's nickname girl?" Caroline asks

"The girl Damon's been spending time with; he won't even give me her name" Stefan answers

"Aw! " Caroline squeals "you have a girl!" she smiles

"She's not my girl blondie… and I would appreciate it if you two would go inside now" I nod towards the door

"As you wish brother" Stefan wraps his arm around Caroline and leads her inside

It's a chilly night in New York city, there's something about the city at night that I've always appreciated, it's like everything comes to life, and it's so beautiful

"Hey" Elena greets, bringing me out of my thoughts "You day dreaming?" she asks

"Just appreciating the city" I smile and pull her into a hug

"There is something special about the city at night" she says thoughtfully

"You read my mind Gilbert" I smirk "shall we?" I gesture towards the door

"We shall" she smiles and head for the entrance

It's a decent sized bar, eclectic decor, a few couches here and there, and a back door leading into some old alleyways with another bar in the back

I spot Stefan sitting a table in the corner

"There's my brother" I point and lead us that way

"Stefan this is Elena, Elena, This is my little brother Stefan"

"Younger brother" he corrects and extends his hand to her "It's very nice to meet you Elena"

"It's nice to meet you too" she smiles sweetly

"Where's blondie?" I ask

"At the bar, she sound be back soon..."

"I brought shots!" sure enough, here comes Caroline, holding a tray of eight shot glasses "Elena?"

"Care?" Elena sounds as confused as I feel

"Wait, you guys know each other?" I ask

"Yeah, she's my roommate" Elena answers

"Wait, is she nickname girl?" Caroline asks

"Am I what?" Elena laughs

"Nothing" I quickly jump in "It's nothing"

What the fuck are the odds of that…I knew this was a bad idea, and yet I had to be an idiot and ignore my internal warning

"Wow, I know they say its a small world, but I just figured that didn't exist in New York" Stefan adds

"Wait, how do you know Damon and Stefan?" Elena asks

"Stefan is the guys I was telling you about…" Caroline starts explaining

While Caroline rambles on; I take the opportunity lean towards Stefan and whisper "How much does she know?" I ask

He creases his eyebrows "What do you mean?"

I sigh in frustration "How much does Caroline know about me?"

"Nothing" he shakes his head

"What do you mean nothing, you had to tell her something" I ask

"I told her that you moved in with me because you were going through a hard time, no details"

A hard time, that's basically the truth, and basically what I told Elena.

"Ok" I sigh "thank you"

"You're going to have to tell her eventually" he says knowingly

"I know that, and I want to make sure it comes from me, I'm just not ready yet"

Stefan's expression changes to one of understanding "ok, when you're ready" he nods

"It really is a small world" Elena speaks up "Care and I grew up together in Virginia"

"That's awesome" Stefan smiles

"Yeah" I nod, still dazed that this is happening

"We have to toast to this" Caroline says as she hands out the first round of shots she brought to the table "to old and new friends" she hold her glass in the air

"Cheers!" we all say in unison

"So how did you two meet?" she asks

"Oh um, he came into the coffee shop one day, and we've been friends ever since" Elena answers

"Aw, that's so cute" she squeals

Elena turns a deep shade of red, fuck, I'm gonna need some more drinks to get through this night, I grab a second shot glass and quickly swig it down

"Yeah, it's downright adorable" I say sarcastically "I'm gonna go get another drink, you guys want anything"

Stefan gives me a concerned look "wanna slow down?"

"I'm fine dad" I say with a dirty look

He must be able to tell I'm not going to back down because he resigns with a "Beer please"

"Sex on the beach for me" Caroline adds

"Typical" I scoff

I look at Elena, waiting for her drink order

"I'll go with you" she gets up, and we head to the bar "So, there's some tension there" she motions back to the table

My brows furrow as I try to think of the best way to answer her "we actually get along really well, he's my little brother and I love him, but lately he's taken on the role of big brother and I don't like it, I don't like him thinking of me in a way that makes him my protector, I'm supposed to do the protecting. Does that make sense?"

To my relief she answers without hesitation "Absolutely"

Thankfully she doesn't push it or ask any more questions, so I change the subject "I can't believe Blondie is your roommate" I shake my head

"I can't believe you're the boyfriend's jack-ass brother" she laughs

"Aw, did she say that? I'm touched" I tease

"Well maybe you are a bit of a jack-ass" she giggles "I mean that is the initial impression you left me with as well"

The sounds of her laugh is quickly becoming one of my favorite things, I find myself going out of my way to make her laugh just so I can hear it one more time

"Now I really am hurt" I pout

"What can I get you guys?" the bartender asks

"I signal Elena to go first

"A tom Collins please" she answers

The bartender looks back at me

"One Kronenbourg, bullet on the rocks, and one… Sex on the beach" I cringe "And two shots of whiskey"

"You got it" she pours us the shots right away, before starting on our drinks

"To a fun night" I hand Elena one of the shots

"To a fun night" she agrees, before we both drink the shots in one gulp

"So, you're a tom Collins girl" I state

"No, I'm a gin girl" she smiles

"Ah, the best kind of girl" I wink

"Is that so?" she blushes

"Oh yeah, much better then vodka girls" I laugh "Vodka girls and "woo" girls tend to go hand in hand, and that's a bit much for me to handle even on my best day"

"what exactly is a "Woo" girl?" she asks

"You know the girls that tend to travel in packs, usually for a birthday party or a bachelorette and everytime a song they like comes on or one of them does a hair flip while dancing they all "woo" in unison" I explain

"You're too much" she shakes her head

"That'll be fifty-six dollars" the bartender says as she sets the drinks in front of us

Elena starts to rummage through her purse

"I got it" I place my hand on her wrist to stop her and hand my card to the bartender "leave it open" I tell her

"Damon..." she starts

"No arguing, I invited you here, it's my treat" I swear this girl has the hardest time letting people take care of her, you should have seen her when I paid for lunch earlier.

With a grunt she finally lets out a soft "fine"

"Atta Girl, now help me carry these back to the table" she reaches for Stefan's beer but I stop her "You take Caroline's, I'll be damned if I'm seen carrying that thing across the bar"

She lets out another adorable giggle "you're so ridiculous"

"Yeah" I agree "but at least I'm also adorable" I smirk

"And don't forget cocky" she laughs

"Oh I'm definitely cocky" I know I'm pushing the line of flirtation, but I just can't help it, especially when she blushes the way she just did; and ok, I must already be feeling those three shots because I'm acting looser then I normally would, and it feels damn good to finally let go

We set the drinks down on the table

"Thanks guys" Stefan says

"OH! I love this song!" Caroline yells as so some techno song comes on "Stefan come dance with me" she grabs Stefan's arms and starts pulling him toward the dance floor

"I should've ordered something a lot stronger then a beer" he yells back at us

"Oh man, he's a saint for putting up with that, also Caroline is definitely the type of girl you would find in a 'woo girl' pack" I shake my head

Elena gives me a serious look, and for a moment I think I may have offended her "Yeah, she can be a lot to handle, but at the end of the day she's one of my best friends and she's one of the best people to have at your side when push comes to shove"

"I sorry, I didn't mean-"

She doesn't let me finish "I know, I just want you to know that your brother is a lucky man, and that there is a reason he puts up with her"

I nod "Ok, I'm glad"

She pulls her drink up to her lips and takes a sip "Thanks for inviting me tonight" she smiles

"Thanks for coming, I'm glad you got to meet my brother" This time it really is the truth, I don't know what I was worried about, now that she's met Stefan it all seems so silly

"And Care's mystery man all in one night" she laughs

I laugh and nod "it's a crazy world we live in" I take a long pull of my drink

I've never been a big drinker especially since the accident, but this loose feeling it's giving me has me coming back for more


Three more shots and an hour later, we're all definitely buzzing and feeling pretty good

Caroline and Stefan have been filtering in and out all night, Caroline has shouted "This is my jam" at least ten times and each time she drags Stefan to the dance floor, he stopped fighting her on it about five songs ago

"No!" I burst into laughter at Elena's story of how she lost her virginity "I can't believe you got caught!"

She nods "it was so humiliating! I mean you build that moment up your whole life and here I gave it to the first cute football player to smile at me, in the back of his car no less! And of course Sheriff Forbes told my parents" she shakes her head

"Wait, Forbes as in…"

"Yeah" she nods "Caroline's mom was the Sheriff"

"Oh my god" I start laughing again "I wonder if Stefie knows"

"She's really a sweet lady" she says in between giggles "Ok your turn"

"Oh man, mine is really boring and cliché" I shake my head "It was with a girl named Katherine the night of our senior prom, we rented and hotel room and drank cheap beer and wine coolers, and then we did it, at the time we thought it was magical, but now looking back on it, it was really rather pathetic" I laugh

"Sometimes the ordinary memories are the best ones" she smiles at me

"Yeah, I guess you're right" I nod in agreement

The music changes from the slow song that was just playing to some upbeat Calvin Harris song, Elena starts swaying in her chair to the beat of the music

"In the words of Caroline, this is my jam" she says

"Then I guess it's my duty to take you to dance" I extend my hand to her

She happily accepts it and a lead us in into the sweaty throngs of people swaying, grinding, and jumping to the beat

Once we find an open spot we stop and begin dancing, Elena swaying and rolling her hips in a way that makes my heart beat faster than it should.

She lifts her hands above her head in a way that makes her look sexy and free and the same time.

I don't know if it's the alcohol or if I'm just tired of denying my attraction to her, but I wrap my arms around her waist, pull her flush against me, and begin moving to the music with her, I know there are hundred reasons why this is a bad idea, but in this moment I just want to be lost, so that's what I do. I let go and I allow myself to get lost in the moment, allow myself to get lost in her intoxication scent as she leans her head against my shoulder and grinds her ass into me. I allow myself to finally feel.

I don't know how long we stay like this, dancing as one, without a care in the world, but at some point Elena twists back around so we're dancing face to face, she leans up on her tip toes, and presses her lips to mine, there's hundreds of alarms going off in my head, telling me to put an end to this right now, but instead I push my fingers into her hair and pull her closer to me.

When I pull away, she looks up at me with her big hazy brown eyes and whispers "Wanna go back to my place?"

I nod wordlessly, grab her hand and hurry us out of the bar.

There are at least ten cabs waiting outside to take drunks like us home, we pile in to the back and I give the driver Elena's address, I glance at my cell phone and see a text from Stefan saying that him and Caroline are back at our place, and that I don't need to worry about finding them on the couch this time.

I look over at Elena and I can tell she's worried that I'll change my mind before we get to her place, so I grab her face and bring my lips to hers in an attempt to put her worry to rest.

I don't know how, but by the time we reach her place, she's ended up straddling me in the back of the cab.

I grab some cash and toss it at the driver before quickly pulling her into the building and rush us to her door.

Once we're inside we started pulling clothes off all the way down the hallway, I stop and push her against the wall; I let my hand roam it way up her thigh and under her skirt until I find what I want

I push the lacy material to the side a slip a finger inside of her

"Damon" she moans

"Fuck, you're so wet" I groan "Which way to your room?"

"Right here" she pulls me into a room on the right, and locks the door behind us

When she turns back to face me she's chewing on her lip nervously

"You have to stop chewing on that lip" I say "that's for me to do" I say before crushing my lips to her

I pull her skirt down her legs and lift her top over her head, so she's left clad in her red lacy bra and underwear

"God, you're beautiful" I whisper

I bend down to press a trail of kisses from her collar bone to the tops of her breasts; I reach around and undo her bra clasp with one hand

"So perfect", I rub her nipple between my finger and thumb, which elicits a moan from her

She grabs my hand and leads me towards the bed, when the back of her knees hit the mattress she sits down and starts unbuckling my belt, when she finally rids me of my pants and boxers she licks the tip of my cock and I can't help the hiss that falls from my lips

"Not tonight" I shake my head "I need to be inside you"

She lies back on the bed, pulling me on top of her

"Do you have a condom?" she asks

"Fuck" I groan, I haven't had to buy condoms in years

"It's ok, I do" she smiles and leans over to her bed side table, I hear the tearing of the foil packet before she returns, condom in hand.

She leans up to roll it over me.

I reposition myself at her entrance, just as I'm about to push forward she stops me

"Are you sure?" she asks

Oh god, not her too, I can't have her acting like I'm some fragile baby too

So without answering her I surge forward and fill her all the way

"Oh god" she moans

I slowly pull back before thrusting again, and again, and again,

"Fuck Damon, you feel so good"

"Let go 'Lena" say as I push into her

She moans and sinks her teeth in her lower lip

"Come for me baby"

And just like that, she falls apart, hearing my name fall from her lips over and over, pushes me over my own edge and I spill myself into the condom

"Fuck Elena" I say as I come crashing down.

I roll over onto my side so I don't crush her

"Mmm"she sighs in content

I pull the condom off and toss it into the trash

"Damon" she says in a sleepy voice post sex voice

"Yeah" I lay back down next to her

"I'm really glad I met you"

Suddenly, the weight of what just happened comes crashing down on my like a tons of bricks, we were just supposed to friends, we were supposed to be easy and fun, and I just complicated everything.

Oh fuck, what have I done...


A/N: Hey guys! I'm back! I felt bad for making you guys wait so long over the holidays so here's an early update, and a super long one at that! I will be out of town for the weekend, so I wanted to get it to you before I left. I hope you enjoy it! Let me know what you think = ) See you guys on Wednesday! Or maybe sooner if you guys ask nicely in the review section ;-)