Disclaimer: I own nothing.

A/N: another B/C one shot, good lord I'm obsessed. Reviews are loved.

Serena was his first kiss.

Blair was irritating, intriguing and complex, too complex for a five year-old Chuck to figure out. She ignored him, never even saw him: he may as well be invisible to her. All she did was trail that boy Nate, who always had his head in the clouds, around and complain about getting her dress dirty. In an effort to captivate her attention he'd pushed her into the mud. She'd cried and wailed and told on him to the teacher. She'd sent him to the naughty-corner, where he spent most of his time, and he'd told Blair she was a big baby before running off outside because he didn't follow rules unless the iron fist of Bart Bass enforced them.

He'd scrambled up a tree and hidden in its branches, soon to be followed by Serena Van Der Woodsen. Serena was everyone's friend everyone liked her. She was smiley and giggly and loved to run and play. 'Are you okay?'

'That Blair is so horrid! I didn't do anything!' He persists with a pout before crossing his arms. 'I just want her to play with me.'

'I'll play with you.' Serena offered, her tiny legs dangling from the branch and swinging out of rhythm.

'You're not Blair.' He told her with his nose in the air because he was a Bass and Bass's didn't do second bests.

Serena had leant in and pressed her plump red lips to his. Her long blonde hair had tickled his face and her clammy little hand had clutched his lightly. It lasted no more than a few seconds but it made his lips tug into a smile. The sun shone brightly, filtered through the green leaves of the tree. 'Let's go to the sandbox!'

Serena may have been his first kiss, but Blair was his first love.

Chuck loved firsts. He loved being the first, and he usually was. He loved being the first to know a secret or a juicy piece of gossip. He loved being the first of a group to do something, anything. He was the first to get drunk, first to lose their virginity (his father's business partner's beautiful, exotic daughter. Gabrielle had been a year older and equally as inexperienced as thirteen year-old Chuck. It had been awkward, clumsy and rushed. She'd left to go back to Italy with her Father, leaving Chuck with only a memory. He'd also been the first to have his heart broken.), first to smoke a joint, first to snort coke, first to have a threesome, first to pay for sex, first to get arrested (had any of the others even got arrested?).

Yes Chuck loved firsts. He loved bragging to Nate about things his best friend had never done, maybe never would.

His favorite first was being Blair Waldorf's first.

Mrs. Bass used to crawl into Chuck's bed late at night, alcohol on her breath, and wrap her dainty arms around her son's tiny frame. Chuck would hold her tight, burying his head in her neck and hiding behind her curtain of blonde curls, sheltering him from the harsh world that lay beyond his bedroom door. He couldn't understand why his mother was so unhappy, though he understood that her misery was slowly driving her insane. He hated it when she got drunk, it scared him: her moods would swing like a pendulum. One minute she'd be dancing on the couch, the next she'd be sobbing all over him and the next, what he hated most of all, she'd be snarling about how he had trapped her, that if he hadn't been born then she would still have a life.

The hefty ring on her finger, so heavy it was slowly dragging her down.

She was wild and untamable by nature, much like Serena. Beautiful but damaged. She was so damn broken.

One day, at the tender age of eight, he'd come home to find her sprawled out on his sheets. She was wearing a dress, her face plastered with make-up and her shoes clad in high heels and he wondered why she was clothed for a night out. He'd called her name and approached hesitantly almost tripping over the empty bottle of vodka on his bedroom floor. Sensing something wasn't right and wondering which stage of drunkenness she was at, he noticed the white bottle lying in her lax fingers. Her face was peaceful; a few tear tracks stained her colorless cheeks, her crimson lips parted and her eyes closed. There was no rise and fall of her chest.

He'd painted the silence with his sobs.

He never wanted to sleep in that bed again, revulsion causing his skin to crawl and fear making his throat constrict. He'd begged Bart to allow him to change rooms, anywhere - anywhere but there. He was so afraid that her restless ghost would haunt him at night, so afraid that guilt would consume him whole. Bart had refused, had forced his son to sleep in that room, in that bed, to help him "get over" the irrational fear. And however much Chuck sobbed and pleaded and threw himself at his father's feet, Bart was set in his decision.

Chuck had to have the maids sing him to sleep at night, or tell him a story or anything to get his mind off the fact that he was sleeping in the room where the world fell apart, where he felt closest to hell.

He didn't know the world could fall apart more than once. But it did.

Seeing Blair in Nate's arms at the night of the cotillion felt like seeing his dead mother on his bed all over again.

Chuck hates being second best more than he hates having second best. He is last resort for no one: least of all Blair fucking Waldorf. So he rises above her, attempting to pull some dignity from the situation and effectively pulling the carpet from under her feet. She goes crashing to the floor, falling without grace. Her throne has already been stolen, her crown snatched away from her. Checkmate. Well he just smashed the whole fucking board to pieces so take that because Chuck Bass is not second best.

Of all his regrets, and though he feigns that he has none; there are plenty, the most painful is choosing pride over Blair. His pride will not comfort him now. His wounded pride, for what's salvaged of it from the wreckage of Blair Waldorf's life, will not save him now.

He regained his pride, only to lose his heart. She didn't know it but she walked out with it in her handbag that night at the bar.