Chapter 10

Blair Waldorf was a princess in every sense of the word. She could be whiny, childish, needy, and insecure. Incredibly spoiled didn't even begin to describe her. Worst of all, she continually obsessed with her life fulfilling a checklist of storybook perfection, no matter how badly she had to warp her perception of reality. But while no one could deny that Blair was a princess, Chuck Bass could never be confused for the golden prince Blair had pined over since birth. Hell, he couldn't even pass for a noble white knight, just waiting on the fringes to swoop in and rescue his fair maiden once the golden prince turned out to be a complete toad. Chuck's rescue plans, though plentiful and sometimes well intentioned, were based on scheming, ulterior motives, deceit, and, more often than not, blackmail. It was hardly a checklist for the makings of a hero. No, with his dark features, wicked smirk, drawling tone, and questionable moral, Chuck bore far more resemblance to the dark and dangerous villains of fairy tales than he ever did to the goodness and light of any make believe protagonist. Unfortunately for Chuck, happily ever afters most definitely did not apply to the antagonists of fairy tales.

And so while the villain may fleetingly get the girl, she was not his for the keeping.

Chuck had long since accepted the fact that everything good in his life inevitably fell apart. It was always a case of when, rather than if, his happiness would bite the dust. Like trying to hold water in his cupped hands, it trickled out from between his fingers no matter how tightly he tried to retain it within his grasp. It was inevitable, and, even at sixteen, Chuck understood this. Unlike his best friend, Chuck knew better than to ever think happiness of any kind was due to him. That's what happened when you didn't grow up with the protective bubble of Anne Archibald to shield you from anything even remotely unpleasant. But the month Chuck had spent with Blair had almost been enough to make him forget. That just made the fall so much worse.

And so Chuck sat on the roof of the Palace hotel, decompressing with his two favorite mood altering companions, the finest hash in Manhattan and a bottle of aged single malt.

There were few people in the world who understood Chuck's fascination with rooftops. It was a simple explanation, really. Living in New York had a multitude of benefits. The social scene was unrivaled. It was the pinnacle of culture and shopping. The food, both in terms of extravagance and diversity, was unparalleled. It also helped that, in New York, the Bass family name was a ticket to getting Chuck whatever he wanted whenever he wanted it. Even so, living in New York, particularly in the hovering and gossipy neighborhood of the Upper East Side, made escape nearly impossible for someone like Chuck Bass. There was always a chance of being seen by someone he knew or, worse yet, someone who knew his father. And though Chuck specialized in flying under the gossip radar of detection for most of the Upper East Siders, he'd yet to figure out how to escape the unrelenting scrutiny of his father.

The great, powerful, and all knowing Bart Bass, Chuck thought with a contemptuous sneer.

Any chance Chuck did have for privacy was ruined by the ever-increasing depths of his father's paranoia. Bart was probably the only man in the world who would rather hire a tail for his son in lieu of having an actual two-sided conversation with the boy. But even Bart's PI has his limitations. Thankfully for Chuck, probing for weaknesses was among his many talents. It hadn't taken long, really. Soon after Chuck discovered the tail his father had on him, he also realized that roofs provided the perfect hiding place. With only a singular exit leading to and from the hotel to the rooftop, the roof of the Palace hotel was among the very few places that Andrew Tyler couldn't follow him. And so, even if it was only for a few hours at a time, Chuck could escape and at least dream of some semblance of privacy.

Of course that was just the surface of Chuck's fascination with rooftops. There was more, much more. It was never enough for Chuck to simply be on the roof. He needed to be perched on the very ledge. While it was true that any location, even those seating positions that were a safe distance from the dangerous ledge would offer most of the benefits that a rooftop had to offer. There would be privacy. The view of the Manhattan skyline at sunset would still be just as spectacular. The breeze would still be able to ruffle his hair; and the warm sunshine would still beat down in delightfully warm pulses on his neck and shoulders. In short, all of the relaxing, therapeutic benefits of being alone on the roof would be there regardless of where he sat on the roof.

But where was the thrill in standing so far away from the ledge, all safe and sound?

He was a Bass, and Bass men never did anything halfway. It was all or none. That was precisely the reason why, despite the expanse of much safer seating arrangements looming behind him, Chuck Bass perched on the ledge of the roof, dangling his expensive loafers over the open air of the city that was several dozen stories below him.

At least that was the very pretty lie to cover up the very ugly truth.

Chuck sat on the ledge because, one day, he would finally find the nerve to do what the world seemed to be tempting him to do since birth: jump. Just a few careful inches in the wrong direction and Chuck would be eating concrete. Physics, a course Chuck had bribed and cheated his way through, suddenly made sense. Abstract ideas, such as the force of gravity and inertia, were made so much easier with real world application. Neglecting air resistance, it would take approximately 32.5 seconds for him to hit the sidewalk.

Bart would be practically brimming with pride to know that Chuck was finally putting his overpriced private education to good use.

If, by some miracle, he survived the 55-story drop, it would only take a few extra minutes for him to lose the quart of blood necessary to send him into irreversible, systemic shock.

See, that's the subject of biology in real world terms.

And this was only if popular opinion proved to be incorrect. Chuck Bass didn't have a heart. No heart? No blood, no mess, no wait. It was simple, clean, and highly effective.

But he was a coward today… the same as every other day of the past sixteen years.

While Chuck sat recklessly on the ledge, his weight remained shifted towards the interior of the rooftop. Safe and sound, just like the coward he was. His aversion to pain, especially that of the physical kind, kept his morbid fascination with suicide in check. But it didn't prevent him from tempting fate. With enough pot and alcohol coursing through his system, it would only be a matter of time before he simply slipped and the decision would be made for him.

Always the coward's way out.

Chuck sighed before taking a heavy drag from his joint, lazily pulling the pungent smoke down into his lungs as he rhythmically swung his legs. His shoes thudded harshly against the bricks of the building on each downswing of his legs, roughly scuffing the fine Italian leather. The shoes would inevitably be scratched and ruined beyond repair. Chuck knew this. But after the day he'd had, he just couldn't bring himself to care.

Indeed, it was a low day when not even high fashion sparked a flicker of interest in Chuck Bass.

He gently flicked the ashes of his joint, sprinkling the city below with the charred remains of his joint. Simultaneously, his other warm swung around his body, bringing a half-filled glass of scotch to his lips. Yes, it was that kind of day… week… year… fucking lifetime. A joint chased by scotch. And if Bart hadn't banned him from using the Bass jet as punishment and his god damn dealer hadn't been sunning it up in Fiji, Chuck would have added a little blow to the equation just for good measure. After all, what good were the five senses if they couldn't all be put to good use?

But the two depressants would have to do for now. So Chuck chain smoked his joints and shot some of the world's finest scotch like cheap whiskey, in deep, glass emptying gulps that burned as they washed down his throat. And, little by little, he happily let the hazy fog of pot and alcohol dull his overly analytical and relentless brain. Numb, number, numbest. So what if Bart had blocked his usual exit strategy? The illusion of escape was almost as good as the real thing. And it was still much more preferable than the fractured mess his life had become. And what a fine mess it was.

His father had essentially disowned him.

His best friend hated him.

And the girl he'd risked that lifetime of friendship over, the one who made his heart stutter in staccato and his stomach flutter? Well, she viewed him as a heartless villain unworthy of her time. She'd made it all too clear that Chuck wasn't even second best to her dear Nathaniel. He wasn't even her last resort. Simply put, he was a brief detour, made by mistake, and not a final destination.

Story of his mother fucking life.

After sixteen years of stern disapproval, Chuck should have been used to Bart's obvious dislike for him. Even so, being exiled from the family suite had been one of the lowest points of Chuck's life. Sure, he had openly mocked the idea of having a functional blended family with the van der Woodsens. But it had been tolerable. Okay, so maybe it had been even better than merely tolerable. It might have even been nice. After all, a dysfunctional blended family with the van der Woodsens was much better than no family at all. And anything was better than the loneliness of life alone with Bart.

Besides, Serena's disproportionate responses to his lewd teasing were quickly becoming the highlight of his day. And Eric, for all his wide-eyed innocence and sage wisdom, was actually fun to be around. Lily was no Stepford wife, but she had put a little extra effort into playing Mommy since they'd united households. It had been a welcomed change to have a parental figure that didn't cringe at the mere sight of him. And even cold and calculating Bart appeared to have softened a miniscule amount. But, as with any semi-good thing in Chuck's life, it didn't last.

There was no such thing as being innocent until proven guilty in the relentlessly judging eyes of Bartholomew Bass. Without so much as a shred of evidence, Bart had convicted Chuck of needlessly tormenting his future step-sibling and sentenced him to solitary confinement in 1812. All because the blond princess of redemption had opened her disproportionately large mouth and squawked, proving yet again that the few brain cells that rattled around, cold and lonely, in her skull functioned far behind her ever gaping mouth. If Chuck had ever been even remotely uncertain as to where he stood with Bart, that moment had clarified everything about their relationship… or the complete lack thereof.

Chuck shouldn't have been surprised. Had there ever been a time in his life when his father expected anything but the worst in him? If there had been such a mythical and happy time, Chuck sure as hell couldn't remember it. Perhaps before he was born Bart had hoped for a son as perfect as he was. But, then again, it had probably been easier for Bart to see the potential for goodness in his son if he hadn't killed his mother. Murderers, even of the infant variety, have a hard time garnering sympathy.

Since birth, it seemed as if nothing Chuck did was ever good enough for the great Bart Bass. And Bart never had the slightest problem making sure Chuck knew exactly how subpar he really was. If Chuck had managed to color in the lines, his father would criticize the amount of purple he'd used. If he built a Lego skyline full of tall skyscrapers, much like the ones his father built, Bart would point out each and every structural flaw. It wasn't enough to just be good, Chuck was supposed to be perfect. The more Bart demanded perfection from his son, the more Chuck grew to resent the man. Chuck's life became a constant cycle of rejection and feelings of inadequacy issued by and because of Bart. And no matter how deeply Chuck attempted to repress such feelings, he still felt the adolescent urge to please his stone-faced father.

So he continued to try. But because Bart Bass could rarely muster an emotion other than disapproval, Chuck continued to fail. No matter how strained the relationship with his father had become, the fallout always took him by surprise.

And that stung.

It was just another reminder, drawn from a very long list, of everything Chuck tried to forget. He would forever be too stupid, juvenile, arrogant, lazy, and all together inadequate in Bart's eyes. All over again, Chuck was faced with the lonely reality that he really was alone in the world. His father had died sixteen years ago, along with his mother, leaving their only son an orphan in everything but name. A filthy-fucking-rich orphan, but an orphan all the same.

Once upon a time, this had meant Chuck would spend the next few weeks mired in a deep cloud of self-loathing and doubt. But the benefit of being sixteen and loaded meant that any emotion could be easily buried under a binge of scotch, whores, and drugs. It all left him numb, which was exactly what Chuck preferred. It was a defense mechanism developed after years and years of emotional abuse. Emotions were a liability. And so Chuck withdrew from his father, his friends, and the world one toke at a time until a concrete wall separated Chuck from the world.

One of the few people to be allowed past that concrete barrier had been his best friend, Nathaniel Archibald. The more Chuck thought about it, the more he realized that their friendship had been doomed from the start. Despite living within blocks of each other, they lived in two truly different worlds. Nate was everything that Chuck was not. He was athletic and agile, quick to smile, and beamed with a halo of goodness and golden perfection. Nate had two parents who, despite their numerous flaws, loved him. But Chuck had never begrudged him any of that. He had outgrown flailing his arms helplessly at the many injustices of the world before he'd turned six. Even six year olds as stupid, lazy, and arrogant as Chuck Bass understood that life was never fair. And crying about the unfairness never changed anything.

But it remained that the two boys that had bonded during a business deal between their fathers had turned into two very different people with two very different outlooks on life. Everything Nate touched turned to golden perfection. Everything Chuck touched seemed to wither and die. Where Nate saw optimism, Chuck saw naivety. Nate trusted everyone. Chuck trusted no one. They were a real life version of Goofus and Galant.

The fight had never really been about Blair. Nate's feelings for girls ran about as deep as a puddle. He loved Blair today, Serena tomorrow, and Brooklyn next week. Nothing ever lasted because Nate was already on to the next bright and shiny object. But Blair had been the one girl Nate could hold over Chuck's head. She was the one girl that Chuck couldn't and wouldn't touch out of respect for Nate. And so Chuck stood by while Nate blundered through a relationship with Blair. Chuck had kept his mouth shut as Nate dated Blair while lusting after Serena. And despite the undeniable chemistry he felt with Blair, Chuck denied himself ever looking at Blair as anything other than an extension of his best friend.

But once that umbilical cord had been severed, everything had changed. At least for a few hours, Blair was no longer bound by her incessant need for a fairytale ending. She was wild, unpredictable, and incredibly… sexy. Even the great Chuck Bass could do little more than raise his eyebrows and glass to her in surprise. He all but waved a little white flag of surrender as the petite brunette entertained the entire room with her milk chocolate eyes and her gyrating hips.

In the limo, his words to her hadn't been an attempt to lure her into his bed. They had been words as open and honest as Chuck Bass got. And, in the end, she had made the first move. She crossed the boundary first. And Chuck had readily accepted what Blair had offered Nate time and time again. In so doing, Chuck somehow managed to do something the golden prince had never been able to do: make Blair happy. Not the kind of happy where her mouth didn't match her eyes. It wasn't even the fake happiness that Blair got from seeing her life go according to her mental script. It was a deep, glowing happiness. It was a giddy happiness, complete with a smile that went straight to her eyes, wrinkles be damned. Her covert relationship with Chuck, for all its fucked up qualities, made her happy. It made them both happy.

Despite being in a relationship with Blair for years, Nate had never made her smile like that. Hell, in all his years Nate himself had never smiled like that. At least not while sober. And Nate had certainly never expected his dark and dangerous friend, who had always made Nate look particularly golden, to find happiness as well. Not when Nate had searched so torturously for that very same happiness himself, without success. It wasn't fair. Blair was his, damn it. If she was going to be happy with anyone, it was going to be him. And, in return, she would bring him happiness as well. And Chuck would continue to brood and fuck anything with implants and a vagina. That's the way it was supposed to be. The truth was that, for the first time in his life, Nate was actually jealous of Chuck. And, for those reasons, Nate resented Chuck.

Chuck shrugged his shoulders at that thought as he lazily flicked the end of his joint into the street below. Nate had been his constant companion since they were boys. He would miss Nate.

But even Nate wasn't worth ruining his high, Chuck thought with a half smile as he lay back against the concrete.

Drugs… the perfect answer for teenage angst.