Title: Eternal Contemplations

Author: fading_tales

Pairing: Damon/Blair (Vampire Diaries/Gossip Girl cross-over)

Disclaimer: I do not own Vampire Diaries, Gossip Girl or any of their characters.

Rating: PG-13

Summary: Timing means nothing and everything when you have an eternity to live. Companion/expansion? fic to Bloody Roses.

Damon loved Katherine. That was a universal truth. But as much as he had loved her, he had hated her for damning him into living an eternity when she went off and got herself killed. Despite the façade of a glamorous eternal stud (his own words), Damon Salvatore hated his immortality. He often wakes up everyday wondering why he doesn't just take off his blasted ring, walk into the sunlight and end it all. Then he remembers. Vengeance. He had promised his brother an eternity of misery, so now he was going to keep that promise. It's the thought that while he may live forever in utter loneliness and agony, he's not going to be doing it alone. It's this thought that keeps him from welcoming the warm embrace of the sun.

Blair loved Nate. That was a universal truth. Unfortunately for her, the object of her affections never really reciprocated the feelings. He was always chasing the sunshine of a girl by the name of Serena Van der Woodsen. As it turns out, that sunshine of a girl was also Blair's best friend. Life's just full of disappointments. She's the girl who has everything and nothing. She doesn't know how it is that she can wake up everyday and pull on a smile that coordinates with the latest Eleanor Waldorf original her mother laid out for her to wear, but she does it to perfection and no one is ever the wiser. She hopes that if she can keep up the act, one day she'll trick herself into believing it. Better yet she can trick others into believing it. One day she'll be the one that preferred over sunshiny blondes with a bubbly personality.

xxx

The party is a bore and truth be told, so is her boyfriend. He's spent most of the night out on the balcony smoking various herbs with Chuck. Nate has never been the same after Serena left. None of them are.

She idly wonders if anyone has ever died of loneliness before, but then berates herself for being so melodramatic. She's a Waldorf for god's sake. Self-pity doesn't wear well with her outfit. For a moment she lets her mask slip and just be. Just when she's starting to get a bit of peace of mind, a girl with a noxiously blue drink spills the contents of her glass down the front of her dress.

One out of two things could happen at this moment. One, Blair could let this lapse of grace go and accept the poor girl's terrified, stammering streams of apologies, or two, she can tear the little wench a new one. While she doesn't necessarily like donning the whole "oh, woe is me" look, if anything Blair Waldorf loves putting on a good show of being a world class bitch.

xxx

New York had always held a certain allure for Damon. He loved the smell and sounds of the city that never sleeps. Insomniacs and nocturnal creatures fill the city, nobodies that will not be missed by anybody. They make for easy pickings.

He's looking for his next meal when he spots her. Amongst the pulsing crowd, she oddly stood out in her silent contemplations. A small frown perched itself delicately on her brows. She's a pretty little thing in her silky white dress, hair in mahogany waves. He forms a little story in his mind of what type of girl she is. Sweet, lovable, innocent… he wants to do naughty things to her that will make her blush.

Her moment of peace is interrupted when a drunken nobody manages to drop a glass full of some toxic blue concoction down the front of her pretty dress. Damon tsks at the disruption of such a pretty picture.

He watches as the stuttering blonde stumbles through a hysterical apology. He waits for his girl in white to accept with a syrupy smile and silence the bumbling blonde idiot. His mental image of a virginal princess who has various cuddly woodland creatures braid her hair in the morning is instantly crushed. He watches as his girl in white smiles a deceptively angelic smile and then proceeds to tear the other girl to shreds with her verbal assaults. With a mouth like that those woodland creatures would die of shock.

Damon scraps the delicate subservient girl in white fantasy and replaces it with this new image of a sassy sharp-tongued dominatrix. He likes this version better.

xxx

Blair successfully reduces the clumsy blonde to tears. She rolls her eyes at the girl's dramatics. Where does this girl get off for crying when it was her who got her Eleanor Waldorf original silk white dress ruined by some frilly blue sorry excuse for a drink? Doesn't the girl know that anyone with class would be drinking a gin martini anyways? With a final eye roll, Blair pushes her way to the ladies' room, her entourage of Kati and Iz, who finally extracted themselves from the dance floor, in tow

She emerges in a new dress, borrowed from Kati and last season, but of passable taste. By now, the evening is all but ruined and she makes her way towards the bar to get that long deserved gin martini that might help soften the blow of being abandoned by her best friend and boyfriend as well as getting one of her mother's precious dresses ruined. She sits herself down at one end of the bar, hoping to find some quality alone time only to have the moment ruined when a stranger sidles up in the seat next to her.

"Hi."

Blair ignores the greeting and merely sips her drink, not sparing the newcomer a passing glance.

Damon chuckles at her snub. The night had been full of pleasant surprises and he's always one who loved the thrill of a chase.

"What? Not a fan of social conventions like greeting? Cat got your tongue? You seemed to have quite a bit to say to that blonde over there earlier."

His supposedly charming remarks falls on deaf ears as the object of his current fascination remains adamant in her efforts to ignore him.

Blair polishes off her drink and before she can order another, the stranger besides her whom she has been consciously ignoring manages to beat her to the punch.

"Another gin martini for the lovely lady."

Annoyed by this incessant bid for her attention, Blair decides some guys just can't take the hint. She allows herself to direct her gaze towards her companion for the first time, her mouth already open to completely and utterly reject the irritating fellow once and for all. She's slightly taken aback by the handsome specimen with a cocky smirk sitting beside her.

"That's your drink, right?"

She gives him a once over. He smiles and doesn't doubt that she likes what she sees. She has yet to say a word to him, but her mouth is slowly curling into a smile and he knows he's got her.

"Wrong. I'm done for the evening."

This girl is full of surprises, her every smile and polite gesture a double entendre. At least he's gotten a word out of her.

"Ah… the lady speaks. And here I thought that muteness was going to become a permanent problem."

"The only problem here," she says setting the newly replenished glass in front of him "is you."

She gets up from the bar and starts walking out the door. Naturally he follows her. They make it outside and she's all but ready to get in the nearest taxi cab and disappear so he decides to pull some tricks up his sleeve.

"'She walks in beauty, like the night…'" he calls out from behind her in a sing-song voice.

She stops in her tracks and turns around to face him.

"You're quoting Byron… really? Does that sort of thing usually work on girls?" she asks with the snootiest voice she can muster and a quirked eyebrow.

"It made you stop and talk to me didn't it?"

He's smiling like the cat that ate the canary and she can't help, but smile back.

"How about a name for my efforts? Reciting Byron can be really embarrassing after all."

Drinking with Byron who couldn't hold his liquor in public was embarrassing as well, but at least Damon got a few good tricks from the old sucker.

"You tell me yours first and I'll think about telling you mine," she replies haughtily.

He chuckles, but obliges the lady. "It's Damon. Damon Salvatore."

"Damon," she repeats. He realizes he likes the way she says his name. He'd like it better if she was purring it into his ear… his lips trailing kisses down that white neck, coming to rest on that tender part of her throat where he can feel her pulse beat the loudest… He's getting way ahead of himself and quickly turns his attention back to the present.

"And you would be…"

She looks him in the eye and he could almost see the gears in her head turning, forming some sort of assessment of him.

"It's Blair Waldorf."

He guesses he passed whatever test she gave him.

"Aren't you afraid of the dark, Blair Waldorf?"

"No. I'm not. I find it's those who can walk in the sunlight to be much more terrifying."

"Smart girl," he says, toying with the ring on his finger.

"Yes, I know," she replies flippantly, bitchy hair-toss included.

"Well… you might not be afraid of the dark… but I might be. Walk me home?" he says with the most disarming smile he can muster.

She gives him an amused look that tells him he's not going to win her over with the cute act. He's ready to switch to plan B (AKA vampiric persuasion), but before he gets a chance to try she surprises him (for the hundredth time) and asks where he's staying. He answers "the Ritz Carlton on West Street" and before he can get another word out she starts walking off in that direction.

She pauses and looks back at him when he notices that he's not following her.

"Well? Are you coming or not?"

He doesn't need asking twice.

xxx

The hotel is only a block away and for an immortal the short span of time it takes to walk from the party to his most un-humble of lodgings is a mere micro-second.

"Care to join me up in my suite?" he asks cockily when they reach the lobby. "Get that martini you missed out on."

It's prime time for a meal and as much as Damon's enjoying his companion's coy play, he's ready to fast forward this little chase to the good part. He catches her eyes with his and lays on the compulsions thick.

She smiles and he for the second time that night he thinks he's got her where he wants her.

"I'll pass," she answers. "It's a school night after all. And I'm not that kind of girl."

With one last sly smile that puts the Mona Lisa to shame, she leaves his side, flags down a taxi and is gone.

Damon is left standing there in front of his fancy hotel, pondering if he's more starved than he thought since his powers of compulsion seemed to have utterly failed. It's an alarming thought and so he marches to the front desk, fixes his icy blue eyes on a pretty redheaded receptionist. The girl quickly falls under his spell and while he takes her up to his room, he ponders what exactly went wrong the first time around. The only reasons for his powers to fail is either she's a witch or in possession of some vervain. Since the anti-vampire herb is not native to Manhattan, city of concrete, only the other option is possible. After licking his lips clean, he makes the calculated decision to look into this mysterious "Blair Waldorf" and her immunity to his vampire mind tricks. Besides…he's in the mood for spunky brunettes.

xxx

It all comes down to this. Damon Salvatore was born in the age of carriages and horses and Blair Waldorf was born in the age of limousines and engines. Decades and years spanned the difference of time between their births. He should have been dust by the time she took her first breath. They weren't meant to ever meet. That's the funny thing about timing. It makes all the difference in the world.

A/N: So after reading about a possible TVD/GG cross-over happening and the possibility of Damon/Blair going canon…I just had to write something! I originally wrote Bloody Roses as a oneshot, but was playing around with the idea of expanding it a little except… the muses for the rest of the story kinda died with the oneshot, so I might just stop here and make this into a companion to Bloody Roses. Or, I might take this into a new direction and turn it into a whole new series, but I have nothing planned so far. What do you guys think? Do you want more? Please review/comment! Let me know what you think!