AN: This is very different to any story I have previously written. This will potentially be a multi-chapter piece, based solely on response and inspiration to continue. The pairing is not completely decided yet but will be AU...to an extent. This is not a pairing I have ever explored before, but I really love them.

Enjoy! :)

Alcoholic, Drug Addict, Train wreck. All words that would nay should be used to describe her and yet are not.

On the Upper East Side secrets, no matter how dark and disturbing were hidden away in Prada packed closets, or flushed down porcelain bowls, with that mornings low fat muffin and skimmed latte. Alcoholism was laughed off as "a few too many" and drug problems were nasty little secrets that could only be detected on those too inexperienced or wasted to wipe the powder from their nostrils.

Only poor people could be placed under these entirely unpleasant categories. Golden girls such as Serena van der Woodsen were just being typical teenagers, if they knocked back too many dirty martinis on a school night; were merely experimenting, if they snorted a cheeky line, in a cramped cubicle to take the edge off an unforgivably dull evening. After all, no one liked a party that didn't contain a certain pizzazz.

This was the attitude adopted by most Upper East Side princesses and their laughably, stereotypical, soulless mothers. Serena had been right there with them all but a week ago, now though, waking up for the fourth morning in a row, staring at a ceiling she had never seen in her life, she realised that perhaps this kind of lifestyle wasn't all it was cracked up to be.

The body beside her was snoring relentlessly, and she couldn't get further from it on the king sized bed if she tried. Slipping out from under the green silk sheets, she tried not to dwell on the fact that all she was wearing was a ridiculously short, tight white skirt. The purple, ruffled thong she could vaguely remember slipping on the night before, now dangling precariously from a lampshade on the other side of the spacious room.

She felt sick. Violently, dangerously, worryingly ill. She wanted to bolt, grab her no doubt, slutty outfit and fly out the room that was, gradually getting smaller and smaller in her still alcohol addled mind. With the single thought "get the fuck out" swirling through her conscience, Serena gave up the futile search for her outfit from the previous evening, grabbed a men's white dress shirt to conceal her bare upper half, abandoned any attempt to retrieve her favourite Gucci pumps, and fled.

Once panting and retching on the sidewalk in her mismatched fashion faux pas, she attempted to hail a cab. Luckily, attracting attention had never been a problem for Serena, with her statuesque figure, and her glistening golden hair she didn't exactly have to beg to be centre stage in life. True to form, within minutes of standing helplessly on the sidewalk, a yellow cab - a little too bright for her hung-over taste pulled up right in front of her. Some things never change, she mused as she settled against the sticky leather seats. She wasn't commenting on the promptness of the taxi. This conclusion was drawn as she caught the driver give her a discreet pitying look in his mirror and the ever familiar sensation of self loathing tears burned her blue, blue eyes.