Summary: She remembers looking out her window as a little girl, feeling like a royal princess looking down on her subjects as they moved about her kingdom. But it's been a long time since her life felt like a fairytale. These days it's more of a tragedy.

AN: Okay, I've had this story in my head for a very long time. It's AU and it's kind of different but for some reason I finally got the urge to just sit down and start actually writing it. It might seem a little confusing at first, but all will be explained. I've actually planned out some of the story, which is something I never do lol, but I really wanna know what people think. Let me know if you are interested in more! :) Or if this is just too strange… [and yes I am continuing my other stories but you just have to write what is inspiring you at the moment, and that was this sooo….]

1

Blair shivers against the cool, late November air as she makes her way down the concrete sidewalks of 5th Avenue, her heels clicking beneath her. The city lights twinkle all around her, creating a warm glow beneath the dark skies. But not even the beginning signs of Christmas in New York can bring the tiniest of smiles to her glossy lips.

Coming to a slow halt, her deep brown eyes skim, bit by bit, up the brick building she used to call home. It's been years since that was the case, but her eyes still instantly train on the window of the room she remembers was once her own. There's a soft light coming from inside that fills her with a longing for something she's been missing for years and she instantly wonders who lives there now.

Is it a family? Is there another little girl who lives for fairytales and happily ever afters calling her old room home?

She squints and tries to catch even the tiniest glimpse inside, but her old home is so high up and she's all the way at the bottom, so it's useless.

A sad smile curls her full lips as she remembers looking down onto this street as a little girl, watching the people walk by with their fancy outfits and pretty shopping bags. She always felt like some sort of royal princess, looking down on her subjects as they moved about her kingdom.

She shakes her head and her gaze drops to the dirty concrete. It's been a long time since she felt like she was living in her very own fairytale. Now she feels more like she is living in a tragedy.

Taking a deep breath, she steps back and continues her trek down the busy street, an uneasy feeling settling in her stomach.

She's avoided this part of the city since the moment she'd stepped back in the US. The Upper East Side holds some of the happiest memories of her life; memories so full of joy and love they should make her smile to think back on, but all they do is hurt all the way into the depths of her soul. Tonight, though, she doesn't have a choice. This is the richest part of the city and therefore it's where she has to be if she wants to keep the fragmented pieces of her life she'd managed to scrape together intact.

Blair turns down a street and tries to swallow back her emotions and restore the stoic determination she had felt when she left her apartment earlier in the evening.

She rounds a corner onto Madison Avenue and forces herself not to think of distant memories of following her mother down the streets as she shopped or sipping hot chocolate while she held her father's hand as they walked through the falling snow. Her unshakeable gaze falls on the towering building of the Palace Hotel and she stubbornly tightens her fists at her sides, determined not to turn back.

Carefully, she crosses the street before passing under the elaborate arch and into the beautiful courtyard. She takes a steadying breath and then pulls open the glass front door.

Pausing once inside, her eyes scan the elaborate decor. Her research had been spot on. This was definitely one of the poshest hotels in the city. This was her mark.

She makes her way to the bar and finds the patrons to be kind of sparse and she frowns, wishing she there were more people around so she could hide a bit in the crowd. Subconsciously she tugs at her hair but still holds her chin high, confidently walking in like she belongs even as she passes men in $3,000 suits and women in dresses that cost more than she cares to think about, while she herself is wearing clothes she'd carefully selected from a thrift store.

In the end though, she knows it won't matter what her outfit costs, all that matters is that she looks good- which she does. Really good. This should be easy.

Her hands shake helplessly as she pulls out a seat at the bar before sliding in.

She pulls off her dark trench coat and rests it against the back of her stool. Her long auburn waves fall against her bare shoulders, the tips just brushing against the top of her tight, strapless black dress.

"Vodka martini," Blair commands to the bartender, challenging him with her eyes to ID her.

The man's eyes scan her body and she feels herself blush, before he simply shrugs and fulfills her request. She calms a little at her first victory of the night and settles into her seat.

Time passes slowly as she looks around the bar nervously. She crosses one leg daintily over the other and slowly spins her drink and tries to look as much the part as she can.

Re-watching her favorite movie this afternoon had been no help what-so-ever. She wishes Tiffany's had covered more of this part of Holly's life, maybe she would have been able to learn a thing or two.

Pulling out the speared olive from her drink, she listlessly chews it.

Certainly there must be something more to this whole thing that she was missing?

Suddenly she hears footsteps approaching from behind her and her heart speeds up. The stool next to her squeaks against the ground as it's pulled out and her back straightens in anticipation.

She hesitates and keeps her eyes on her glass timidly.

There's at least five other open seats at the bar so it can't be a coincidence that whoever it is has chosen a seat next to her.

You can do this, she tells herself. You can do this. You have to do this.

She takes one last deep breath before finally looking up from her drink, a flirtatious smile she'd practiced in the mirror fixed on her lips. Her brown eyes glide over and land on the face of the man who has sat next to her and she freezes.

Chuck Bass.

Her stomach instantly drops.

This is why she didn't want to come to the Upper East Side. She didn't want to risk being recognized by anyone from her former life here. But now she'd walked right into the boy who used to steal her headbands and push her on the swings. The one who, according to the glimpses of the papers she'd caught, was now one of the richest, most notorious womanizers in the city.

She can only watch in horror as his eyes narrow at her and she knows she's been recognized.

She opens her mouth to say something, anything, but finds herself speechless. She doesn't want to have to explain her non-designer clothing or her slightly over worn shoes, or worst of all have to admit that she's currently residing in Brooklyn of all places.

Abruptly, he shakes his head as if to clear it and moves forward.

He leans into her and she swallows at the feel of his breath against her skin. The stench of scotch and expensive cologne is both suffocating and intoxicating.

"How much?"

Her mouth hangs open in shock.

She can't believe she did it. This was really easy. Too easy.

Somewhere in the back of her mind she's disappointed Chuck didn't remember her, but she decidedly ignores the feeling. Instead, a small smirk curls her lips because she won. She knew she could do this.

He pulls back after a moment and looks at her, his eyes narrowing in a peculiar way again.

Her smirk falters as she realizes he asked her a question, but she doesn't know how to answer. How much is she supposed to say? She's never done this before, she doesn't know how it works. All she knows is she needs $750 for her rent. But she needs to pay her electric too… And she should probably get groceries.

"A thousand," she blurts suddenly, hoping she doesn't sound like she has no clue what she is talking about.

He studies her petite frame for a long moment, and she can't help but flush at his heated stare.

His hand suddenly moves forward, warm fingers curling tight around her exposed thigh and a tiny gasp of surprise escapes her lips.

A small smirk curls his lips and he nods almost imperceptibly in agreement to her price.

After that Blair barely has time to think before Chuck is off, sliding out of his seat and heading towards the exit without even another glance in her direction.

It takes her a few seconds before she realizes she is supposed to follow. Hurriedly she gathers up her coat and heads after him, catching up to him just as he makes his way into the elevator. The door closes behind the two of them, locking them alone in the silver box.

She studies his reflection in the doors in trepidation, trying to prepare herself for his next move. Surprisingly, though, he doesn't advance on her. Instead he stares almost sightlessly ahead, his eyes disinterested and heavy as he looks at his own reflection.

The elevator dings and opens, and once again he's walking off without even acknowledging she exists.

Her palms start to sweat and she rubs them anxiously against her dress before following him out onto the 18th floor.

He's already unlocking the door to his suite when she spots him, and once it's open, he finally trains his eyes on her. But his hooded gaze doesn't find her face but instead studies the curves of her body in veiled appreciation. He holds open the door for her and can feel his eyes burning against her body as she passes.

She tries to stop the shaky breath that escapes her lips as she twists the ruby ring on her finger uneasily.

The door closes and the metal click of the lock sounds unbelievably loud from behind her.

She's barely has the chance to turn around when suddenly Chuck's right next to her.

Without preamble he pulls her coat from her grasp and throws it carelessly aside. His hands find her waist and push her backwards until she's pinned against the wall. His lips quickly find her neck and gently suck against her skin before he brushes his teeth the same spot.

She bites her lip and rests her hands atop his shoulders, unsure of what to do with herself. She can't deny what he's doing feels good, but suddenly she's so overcome with nausea at this that she's not sure what to do.

His lips make a path down her chest to the neckline of her low-cut dress before traveling back up to her neck until she can feel his hot breath against her ear.

"You know," he murmurs huskily, "I'm spending a lot of money for me to be doing all the work."

She swallows the bile at the back of her throat.

He pulls back and meets her gaze, giving her a pointed look.

"Um," she stutters, her gaze finding the wall, the ceiling, as she tries to find the resolve and strength in her that led her to this hotel tonight, but it seems impossible. "I - Um.."

One of his large warm hands leaves her side and digs into his front pocket and he produces a tiny vial. He smirks at her as he dangles the white powder between them. "Maybe you just need something to get the party started?"

Her eyes widen in horror and she quickly shakes her head. "No, no," she says as firmly as she can manage, "definitely not."

His smirk falters and he lets out a sigh, his other hand dropping from her side as well, and she panics. She can tell he's getting bored with her and that just can't happen. She needs that money. There is no other option than to go through with this, because if there was, she never would have come here in the first place.

So in an act of desperation, she squeezes her eyes shut and leans forward to kiss him.

Some part of her knows that this is not really what she is supposed to do. The kiss is far to chaste for the situation and she wonders if kissing is even allowed or if that was some old wives tale, but he seems to like it.

In fact he seems pleasantly surprised by the gentle kiss, but he doesn't hesitate to take it one step further.

She allows his tongue into her mouth and even enjoys it just the slightest. Her full lips match his kiss for kiss, breath for breath in some instinctual rhythm that overcomes her with an odd feeling.

She lifts one of her hands to move it from his shoulder to his hair but the way it trembles in the air makes her think better of it.

Blair is perfectly content to make out against the wall like the teenagers, but this isn't the arrangement that they have. It's not very long until his hands start to wander and she pulls back in slight alarm, feigning the need for air.

His gaze finds hers and he studies her curiously.

"Do I know you from somewhere?"

Her mouth goes dry at the question, her heart speeding up in her chest, but she can't even open her mouth to answer before he continues.

"Have we done this before?"

She frowns and shakes her head as she stares longingly into his hazel eyes.

Honestly, she doesn't want him to remember her. She doesn't want him to equate the perfectly put together little girl from his childhood together with the mess of a young woman that stands before him. A part of her, though, wishes she weren't so forgettable.

She waits as he continues to study her in question and she realizes the boy she remembers doesn't really match the one before her now. Sure they both have the dark, mischievous eyes and an apparent affinity for bow ties, but the Chuck from her childhood was as well mannered and gentlemanly as you could be at age seven and was always one of the most thoughtful, loyal people she knew. He certainly didn't seem like the type that would grow up to be paying for the company of woman and carrying around a vial of coke at the age of nineteen.

"Are you sure? Because-"

Cutting off his questioning with another kiss, she digs her fingers into his shoulder blades, trying to act more powerful and in control.

Chuck, in turn, begins his exploration of her body again. This time, though, she lets him, ignoring every impulse in her body to stop this.

His hands eventually find their way around to cup her ass underneath her dress and her mind seems to go blank. He pulls her flush against him, pressing himself against her and she can't help the sudden sound that escapes her lips.

It's not until he pulls back and stares at her wide-eyed that she realizes it was a sob.

His eyes suddenly soften as his hand moves to touch the side of her face almost in fascination, the pad of his thumb sweeping across her cheek.

She dumbly wonders when she had even started crying.

He watches her with something in his eyes that she can't quite read, but all she feels is his pity.

She tries to step back, but she instantly hits the wall. She panics, feeling trapped and embarassed and ashamed.

"I-I'm sorry," she mutters, looking anywhere but at him as she slides away from him against the wall. This was a huge mistake. She has to get out of this place now. "I'm so sorry…"

"Wait," she hears him call to her in confusion, his hand gently grasping at her wrist. "You don't have to…"

Blair easily shakes off his hold and finds her way to the door. She flings it open, her vision blurry with tears as she stumbles toward the elevator, ignoring the gaze she can feel burning into her back, watching her run away.

It isn't until she the doors close behind her that she completely falls apart.

What am I supposed to do now?

TBC….?

Please let me know what you think of this. Any feedback would be greatly appreciated. I'd love to know if there is any interest for me to continue. :)