Two YouTube videos, five Fan Pics and several crazy pills later and Jenny/Damon is suddenly extremely appealing to me in terms of Crack Pairings. I don't even know what I'm doing...


P.S. Don't worry about 'I'm not a drinker, I'm a drunk' because this is just a little procrastinating side-project. Chapter eight of 'I'm not a drinker, I'm a drunk' will be up soon.

Chapter One: Let's do something to regret.

New York City was always one of Damon's favourite places in the world. He had been everywhere – pretty much – and somehow he always found himself in New York because, hey, why not? The city never slept and neither did he, so it was a match made in heaven.

Although, since the whole Mystic Falls schtick two years ago, he had become very... humanised. To say the least. He slept a whole eight hours some nights, which was even more ridiculous when you consider that his kind usually slept during the day.

Through word of mouth he heard about some throwback burlesque club called Victrola. Soon enough he found himself in what could only be described as a retro escapist strip club. See, this was why he liked New York. It was so much better than The Grill back in Mystic Falls where the prime entertainment was pool and annoying cougars. Yes. This was much better.

Damon settled himself into one of the plush couches and a scantily clad brunette in nothing but a corset and stockings offered him a drink. He asked for a scotch – no, make it a double. Then he made himself comfortable and observed his surroundings. He had just eaten that morning (a very eager waitress at the corner diner left him her number, so he had tasted and compelled her when she went out for a cigarette break) but all of these girls were quite exceedingly attractive. Of course, they were slathered in red lipstick and covered in perfume that marred their natural blood-lust inducing scent, but they were still appealing.

Damon was on his second scotch when she walked in. She was being tailed by two other girls and didn't look a day over eighteen. He wondered briefly how she was even allowed in before a young man (who he had previously recognised as the owner) came up and greeted her, giving her a chaste and polite kiss on the cheek. That explained it. The friend of the boss doesn't need I.D.

She and her cohorts slid into a booth near Damon. The leader – a tall, pretty blonde with dark eye makeup and long legs – had a sour expression on her face while her two friends giggled and pointed around the club. They had clearly never been there before. The leader nodded to her friends and offered them a small, half-hearted smile and they ran off to go get drinks. She was all alone. Ripe for the picking.

Damon didn't approach her. In the fifteen minutes they had been there she had already been hit on three times and all of those men – no matter how young, attractive or wealthy – were turned down with a pursing of her lips and a raise of one slim eyebrow. Instead, Damon thought, she would come to him.

Vampires are predatory, but subtle. They are built to attract their foes and be alluring. It had something to do with endorphins, although Damon never cared enough to find out the exact details. He had no doubts that her eyes would find him sooner or later.

And when their eyes did meet, it was an explosion. Her dark blue eyes met his bright azure ones and he saw her take a sharp intake of breath. Of course she did. She wasn't expecting the intensity of his stare or the allure of his very presence.

It was perfectly normal.

What he didn't expect was the way she pursed her lips at him – at him – and turned her head away.

Oh, it was so on.

When her friends got back, they noticed him staring at their leader. They giggled, the way teenage girls often do, and pointed him out. Over the music of the club, Damon could still hear them.

That hot guy over there is totally staring at you, J!

Yeah. What of it?

He's so fine! We think you should go over and speak to him.

He's just being a pervert.

Oh my god, J! Please go talk to him or I will.

Then the leader – named 'J' for some reason – let out a resigned sigh through her red painted lips and rolled her charcoal smudged eyes. She rose from her seat, all long limbs in a short dress, and made her way over to Damon's table. He didn't take his eyes off of hers until she was right in front of him, staring him down.

"Hello," he said smoothly, raising an eyebrow. The girl didn't blink, she just let her lips curve into the slightest approximation of a smile.

"You're staring at me."

"Was I?"

She looked away in obvious frustration with his attitude. She was used to people following her every move. She was used to being the Queen.

"I'm Jenny. Jenny Humphrey," she introduced herself.

"Bond. James Bond," Damon mocked, taking a sip of his scotch. Jenny huffed and let out an uncontrollable smirk.

"I know the owner, you know. I could have you kicked out."

"Damon," he replied. "Salvatore."

Jenny took his real name as an indication that she was welcome to sit down. She sat down on the lush sofa beside Damon and called over a waiter, ordering a gin and tonic.

"Aren't you a little young to be drinking?" Damon queried, cocking an eyebrow again.

"Aren't you a little old to be hitting on eighteen-year-olds?" she asked as she sipped her drink.

"You have no idea."

Later that night, when the gin and scotch was swimming in their respective systems, Jenny agreed to let Damon come home with her. He had no place to stay as he was only there for the night and had to be off soon. Katherine was in New York and he desperately needed to avoid bumping into her, though that wasn't what he told Jenny.

She had just nodded at him. She had an apartment on the Upper East Side in a hotel building. He knew her family must be rich but she didn't reply when he commented on it. In a slur, she simply mumbled...

"Ever been to Brooklyn?"

Even in his drunken state, Damon took in every inch of her small but lush apartment. There was a mannequin in the corner and textbooks with F.I.T written on them in big letters. Fashion Institute? He was piecing together Jennifer Humphrey's puzzle and it seemed a large one.

He didn't get much time to think, though. Because Jenny hooked her fingers into the buttons of his shirt and brought him close to her. Her sweet, gin scented breath tickled his face before she lowered her mouth onto his. Then he could taste her. He tasted her last cigarette, her gin and tonics, her chocolate strawberry snack, her dark red lipstick. Her tongue swiped the inside of his mouth, trying to taste him, too. What would she taste? His scotch, his death, the blood of the waitress he had that morning?

Damon had promised himself No More Teenagers. Caroline Forbes had thrown herself at him and Elena... well, Elena had been something else entirely. What they both had in common was an unparalleled innocence about them that made him uncomfortable. He wasn't the 24 he looked. He was over 160 and he felt it in his bones and teenagers were so gangly, and awkward and trying to find themselves.

Jenny was different. She knew who she was. She was an old soul.

He could taste that on her, too.

When she undressed she was wearing a garter belt, which made Damon chuckle. She took off her high-heels and suddenly became shorter than him and her dress was over her head. She was pale in the moonlight, milky white skin that glowed in the dark. Damon removed his clothes and manoeuvred them to the bed. She smelled of gin and Chanel Number Five.

He kissed down her translucent flesh and could feel her pulse under her skin. But he was far more aroused than hungry and instead guided himself inside her while she moaned and bit down on his shoulder softly. He rocked and she moaned breathily and low, her black fingernails digging into his back and leaving half-moons in his flesh.

When he finally climaxed after what felt like the most long-lasting and intense sex of his un-life, Damon felt Jenny clench and orgasm around him, quivering with pleasure as she rode him off the edge.

Afterwards, they lay there. Damon wasn't asleep, though he was exhausted. He could feel the light coming in through the window. It was almost morning. How long had they been going at it? He wrapped his arms around Jenny's thin waist and listened to the sound of her steady breathing. He played games with her breathing – trying to make them breathe in sync, in canon. He made patterns with their breaths and inhaled her.

Damon was not a romantic.

Sure there was love and puppies and all that boorish nonsense, but he didn't believe in soul mates. He didn't even know if he believed in souls. But when he awoke without recognising that he had gone to sleep and found her gone, he felt a pang of disappointment. Girls didn't skip out on him. He was Damon fucking Salvatore! He bled girls dry and left them braindead and they most certainly enjoyed it.

He got up, slipped on his boxers, and exited the bedroom to take a good look around the apartment. On the windowsill was an ashtray with a few butts in it. Fresh, new from his morning. She had only left a few minutes ago. He moved over to the kitchen and saw a post-it on the fridge.

Damon (if that is your real name),

I had to go to class. Help yourself to anything in the fridge, though I know you probably didn't need permission.


He laughed aloud at the note. She was awfully flippant for such a young girl. Did she do this often? Drag drunken strangers into her apartment, have her way with them and then leave behind a post-it? Damon opened the fridge and pulled out some leftover pizza, though he knew that the dull aching throb in the back of his throat wasn't a regular kind of hunger. He looked at his watch absently and decided to see if any of the Victrola girls had slipped him their phone number...

When Jenny got home from class, it was almost dark. She sighed and threw the samples she'd made in Design over a chair in the living room before making her way to the kitchen for some water. On the fridge, underneath her mandatory 'Thanks For The Fuck' post-it was another note.

Jenny (if that is your real name),

I'm thinking of staying in New York. Look me up at Victrola.


She resisted the urge to smile. Damon Salvatore was most definitely one of the most charming and good-looking people she had ever met. But it was an uneasy charm, something dangerous about it. Distantly, her mind recalled Nate Archibald and his easy charm which had something more to do with his family, his money, his green eyes, his easy smile and his flicky hair. No, Damon Salvatore had another breed of charm altogether. An animal charm.

Jenny immediately had the impulse to grab her coat and head down to Victrola and start the whole act again – the staring, the drinks, the sex. But she thought better of it and instead whipped out her mobile and tapped in a quick text.

You know that guy I left with last night? X J

While she waited for a reply, she wandered around her apartment before winding up at the windowsill. She reached into her bag to light a cigarette, but stopped when she saw the ashtray. It was filled to the brim with cigarette butts and there was a post-it hanging off of it as well.

They'll kill you. – Damon

Jenny just laughed and lit her cigarette, briefly pondering the point of chainsmoking a whole pack just to prove a point. She was halfway through her cigarette when her phone buzzed.

Indeed I do. Being nasty, are we? –C

Jenny rolled her eyes and replied to Chuck's text.

He said he'd be at Victrola tonight. Keep an eye out, will you?

The reply was instant:

Of course. Any particular message you'd like conveyed?

Jenny thought for a moment, taking a deep, long drag on her cigarette.

No. Just tell me when he leaves.

Jenny got changed out of her school clothes – flats, skinny jeans, a singlet and her hair in a long plait – into her more signature style. She had spent most of her teenage years running up and down the Upper East Side in 5 inch heels and tight dresses. Starting at F.I.T had meant that she had to be more practical, which wasn't something she enjoyed very much. She casually made her way to her closet before deciding on a short black dress, lace stockings and a pair of Steve Madden pumps. She then shook out her long, white blonde hair and picked up a Burberry coat.

Hanging out with Blair wasn't something she did often, or very willingly, but they had maintained a strained friendship since Blair got over the whole You-Slept-With-Chuck thing and Jenny had wised up and become less of a brat. Meeting at the hotel bar to bitch was about as close as they got to being teenagers in the Constance Billard hierarchy again, though they weren't particularly fond memories for Jenny.

Blair was waiting for her at the bar, as usual, tapping on her phone and sipping on a martini. When she saw Jenny approach, a smile quirked on her lips and she sighed.

"You're just a little slut, aren't you?"

Jenny rolled her eyes. It wasn't the usual greeting, but it was the usual animosity she expected from Blair.

"Yes, Blair. I'm a bit fat slut," Jenny sat beside her at the bar and just ordered water. She was still trying to get all of the gin and tonic out of her system from the night before.

"I'm talking about Gossip Girl, J," Blair sighed and flashed her phone at her. On Gossip Girl's page, there was a picture of sitting at Victrola with Damon, a picture of her leaving with Damon and a picture of her letting him into her apartment building.


"What, so now I'm not allowed to have a social life?" Jenny queried, raising an eyebrow.

"J, you can't have one-night-stands. It's really not good for your reputation."

"It wasn't a one-night-stand," Jenny defended herself automatically, frowning.

Blair was silent, before tucking a strand of chocolate hair behind her ear and lifting her chin in interest.

"Oh, really?"

Jenny bit her lip slightly, thinking of how to reply. "His name's Damon. He's... older than me," she conceded.

"How much older?"

Jenny was about to say 'I don't know. Early to mid twenties?' but that would have supported the one-night-stand theory that Blair was (correctly) sporting, and she didn't want to admit that she didn't know him well.

"Twenty-five," Jenny said, before deciding to elaborate, "Well, almost. His birthday's coming up."

Blair probed even further, taking a deep sip from her martini.

"Last name?"



"His family is."

"Lives in New York?"


"Then where?"

Jenny had to think. Back at Victrola she had asked him that same question. And the answer she'd received was as mysterious as he was – 'I don't have a home'. But then she'd asked where he came from and he said something about a nosey little town called Mystic Somethingorother. She couldn't remember.

"A town called Mystic. Very small," she settled on, knowing full well that Blair would do a raincheck on any and all towns with the word 'Mystic' in them.

Blair just nodded and said in her usual, clipped tone, "Well, the Fashion Week Fundraiser is tomorrow night. You should bring him. Introduce him to everyone."

Jenny began to stammer, "Uh, I don't think we're at that point yet, B. I mean, really we've only been seeing each other-"

"So he's good enough to sleep with but not good enough to meet your friends and family?" Blair questioned, knowing that Jenny couldn't argue with that one.

Jenny just forced a smile and said, "I'll ask him."

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