A/N: I Don't Own Gossip Girl..... yet?

Chapter One: Beginnings

Ever since he was a little boy, Bart Bass had known he would make something of himself.

Seeing the business men walk by in their fancy suits as he walked to school he imagined all day long what it would be like to be in their shoes, just for a day.

His parents were not well-off, but you couldn't call them poor. He went to an upstanding school and worked tirelessly of achieving outstanding grades.

He was not, unfortunately, one of the many that would grace the hallowed halls of ivy league institutions. Instead he worked tirelessly, once again, at different business firms collecting coffee, running errands and secretly tuning into the inner working of business.

By the time he was twenty he had secured a higher position within a business. Not a huge promotion, but he was now working on things that mattered (all the while saving every penny towards his dream).

Five Stirling recommendations, a colossal loan and deposit later Bart Bass strolled out of the bank with a skip in his step and building in his possession.

A very good investment indeed, the building slowly raked in the money and confidence needed to set Bart on his path to greatness. His years of business experience helped him gain confidence in old colleagues and new investors leading to a second and third bass building purchased.

At twenty five, Bart Bass had three buildings and a plan for a mighty industry to unfold with nothing standing in his way. An astounding accomplishment from someone who started off with next to nothing.

When Charles Bartholomew Bass was a little boy, his greatest dream was not to be an astronaut or a superhero. He simply ignored the stupid children who played with their heads in the clouds. Young Chuck demanded his nannies play mansions with him. Mansions was a game he invented, wherein everything was exactly the same, except Chuck was master of the household (it made him feel less alone to imagine he was in charge)

His greatest dream was to play mansions with his father, but instead he would have to settle for toys, blank stares, cold forced hugs forced chit chat whenever his father could spare time.

When he was six, Chuck's father moved them to a much bigger apartment on the Upper East Side. They had been well-off before, but this was a whole new level of indulgence for the young boy.

His nanny count went from two to five, the presents became clothing and electronics and he began to socialise much more regularly with the children of the area, sons and daughters of powerful New Yorkers his father sought to mingle with.

When Chuck did see his father, he was in awe.

The man had such power, and it all seemed so easy.

So logically, if having millions came naturally to Bart, would it not also come naturally to Chuck?

This was the mindset he lived in. And by the time he reached ten he lived his life barely awake during classes, flirting around with any female that caught his eye and lazily rolling pages of text books into joints behind trees in the park with Nate Archibald.

Chuck Bass started off with everything, but it was worthless when compared to how empty he felt on the inside.

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