Summary: When Chuck Bass lost a bet to bed the most respected actress in all of London, not only did he lose money but a part of himself when she was announced dead. But a year later when he discovers Blair Waldorf claiming to be Serena Van der Woodsen, an heiress who was lost for eighteen years and only found a year ago, he decides to find out what she is hiding and what happened to the real Van der Woodsen heiress. And would the imposter see him as a friend or foe.

Chuck lay sprawled across one of the seats watching as girls clad in clothing that left nothing to the imagination danced across the stage. He knew his father would not forgive him for disappearing again and also that his father had men who were by now scouting the whole of London for him but he could care less just like his father showed no interest in his business plans and ideas. He closed his lips around the glass of scotch he had been swirling while pretending to be interested in what his companion Carter and his friend Daniel Humphrey discussed.

"Hey Chuck only two days more to redeem your bet" Carter said drawing Chucks attention. He only turned to Carter with his famous smirk on his lips "more than what I need. Just a day would be enough to have Blair Waldorf writhing under me in pleasure" He said staring Carter in the eye with a lazy smile grazing his lips.

"What bet?" Dan who had just met the two asked."Blair Waldorf refused to see me or receive any of the gifts I sent her which by the way were very expensive jewelry" Carter explained. "But Chuck... "Chuck cut Carter midsentence as he continued in a lazy drawl "I declared it was only because she wasn't approached by the right guy or in the right way besides we all know no actress is a saint so I bet a ten grand to not only seduce her but bed her by the end of the week". Chuck said. Dan whose eyes were now widely open in shock (whether it was over the large amount these men were ready to loose or the horrible way they spoke about the young actress no one knew) finally found his voice " There's no way you're going to win. The whole of London knows Blair Waldorf is a respectable actress when it comes to character and no one can rob her of her virtue".

Chuck looked Daniel Humphrey in the face not a bit shaken by his words and confidently and quietly said "I'll double the bet"

Everyone was silent at the table as they stared at him

"You must be crazy" Dan said. Chuck coolly replied, "Take up the bet then" but Dan for fear of losing all that he had ever worked for if only it was up to that amount quietly refused. It was quite obvious to everyone who had heard what transpired between the men that this man Chuck Bass would likely succeed where a whole lot of London's most eligible men had failed and that Blair Waldorf may finally find her match in this man whose indifference and confidence spoke volumes. Apart from Daniel and Carter no one knew anything about him except the fact that he was from New York and the fact that he was a rich, self assured and confident man who most of London's aristocratic women could not resist. Blair Waldorf on the other hand was almost a household name for theatre lovers. Word about her great talent, admirable beauty, grace and poise as her reputation when it came to men spread around London. Blair Waldorf never gave any man a chance. Some said it was because she was frigid and a prude who did not know how to satisfy any man in bed, but her loyal fans knew those were rumors spread by the many men she had so unceremoniously turned down. Some secretly compared her to Elizabeth I, the virgin queen. For the most part Blair Waldorf reputation remained untainted.

Chuck stood up from his seat to bid farewell to his companions for tonight was the night he was going to to meet the famous actress and there was no way she could avoid him this time. For she had returned the two gifts he had sent earlier with a note saying she would not allow herself to be insulted by accepting such a gift. He knew the gift was sure to get a rise out of her and that is what he wanted. To get a reaction out of the woman who was known to be an ice queen.

"Hey Chuck, are you leaving so soon" Carter asked

"Yes I must go I have some important matters to take care of".

"But you'll be at the theatre?"

"Perhaps" Chuck answered nonchalantly.

"You know, its Romeo and Juliet tonight and its one of her best parts" Dan said. Chuck turned to look at Dan pretending to be absorbing this 'new information' with his trademark smirk .She's the best Juliet I've seen, she's a genius. Dan added.

"I'll have to see that for myself" chuck said as he picked his hat. Goodnight gentlemen.

He walked over to the vehicle waiting outside for him and gave directions to the theatre where Blair was going to be performing tonight. He was glad he had other things to occupy his mind so he wouldn't have to think of other matters that troubled him. Time for a little fun told himself as his chauffeur drove off.

Blair Waldorf sat in her dressing room staring at the box she had thrown across the room. The contents were however not what she expected. She had expected to see more insulting lingerie from the box but it seemed the insufferable bastard had a little decency after all. She stared at the expensive red gown that spilled out of the box. She was sure whatever pig of a man Chuck Bass was he had no moral fiber bestowing upon her gifts that even whores would refuse. But she was no whore and she could not be bought. She called for the gown to be sent back.

Chuck Bass entered the theatre through the backdoor and headed straight for the manager's office. The manager rose to meet him. "Ah Charles, glad you could make it and thank you for saving us and agreeing to be our new Romeo on such short notice. Blair would be glad to meet her new partner for tonight. I assure you."

Chuck Bass smirked in response. "she sure will "