Summary- 'I realize later that for the first time tonight my troubles with Serena, Nate and mother were out of my mind due to Chuck Bass. The Basstard.' I'll bring you into the wondrous lives of Chuck Bass and Blair Waldorf. Serena and Nate's sinful night is the catalysis for the beginning of Chuck and Blair in a way we never knew. A story on how these two teens struggle for their feelings in a land filled with designer goods, expensive clothes, private limos, and exclusive parties.


A.N Haven't done this in a long time. I do not know if people even read GG fics anymore but this was in my head for a while now so here it is. Picking up from the originally plotline of Serena van der Woodsen return to the UES this is story told through Blair and Chuck's point of view. I pretty much follow the original episode but things are going to change greatly by the next episode. Blair and Chuck already have feelings for each other when we began that they fail to recognize in themselves. The rating might go up in later chapters. Gossip Girl characters are somewhat wild and unbelievable for teenagers. I try to stay true to the personalities of all the character (besides Eleanor and Bart). Additionally there will be a lot of Blair and Eleanor as well as Chuck and Bart in this story. Since this will be told from C & B POV very little Dan and little J in the beginning.

Disclaimer: I do not own Gossip Girl or any persons or places that are depicted in my story.


"How characteristic of your perverse heart that longs only for what happens to be out of reach."
― Pierre Choderlos de Laclos -Les Liaisons Dangereuses


Spotted at Grand Central, bags in hand: Serena van der Woodsen." Was it only a year ago our It Girl mysteriously disappeared for "boarding school?" And just as suddenly, she's back. Don't believe me? See for yourselves. Lucky for us Melanie91 sent proof. Thanks for the photo, Mel, -XOXO

Sometimes I wondered why I bothered with such a simple predictable best friend. He was the golden boy of the Upper East Side and was everything you expected with it. Perfect on the outside and sometimes dreadfully boring on the inside but he was loyal. He was only an Archibald and his family name was cemented in this city while mine was only newly plastered. See here in this part of Manhattan certain names -Vanderbilt, Astor, Whitney - go a long way. You cannot buy your way in with a few million like in South Beach, San Francisco, or like those wannabes in the Silicon Valley. You need billions. Bass billions. Yet even with my billions here, I was searching for the Golden Boy with direct order from the Queen herself.

Nathaniel had gone 'missing' a few hours ago. He was supposed to turn up at Blair's mother parities tonight for fashion week and failed to show. She needed him to go over details for her Kiss the Lips Party this weekend. This was not unlike him and Blair was on the verge of throwing a fit especially after the gossip girl blast about Serena's return. Wanting no part in the uptight princess's oncoming rant or wanting to socialize with UES preps and gold digging models now I gladly did her bidding. Figuring Nathaniel was holed up in my suite I made my way back to the Palace. Opening the door to 1812, I walked into the two dumb blondes going at it on my couch. Serena was straddling Nathaniel while his hands fisted in her hair pulling tightly. I snapped a photo on my photo because you never know when you need blackmail. Gossip Girl loves her photo evidence. I leaned back against the door to close it. Crossing my hands over my chest waiting to see when they were going to notice me. It was only would Serena's dress was flung in my direction did I cough to announce my presence.

"Chuck! What the fuck man" Nate yelled over Serena shrieking at me to throw her dress back.

Fuck was right. Serena was Blair's best friend or was. Who can keep track. Serena was supposed to be at boarding school not about to have sex with Blair's boyfriend. Blair's prince charming. Flashing them a classic Bass smirk I walked to the bar for some scotch. I needed a drink and maybe a smoke. Pouring the amber liquid into the glass slowly giving the blonde-haired people sometime to sit in the uncomfortable silence I thought of Blair. Blair Waldorf was top grade bitch. Moreover, I cherished her for it. I thought the three people in this room cared for her the most in the world. Well maybe not so much Nathaniel but in his own way I am sure he has 'deep' feelings for her. She is elegance defined; she felt like silk, tasted like smoothest scotch, smelled like lavender, had the strength of diamonds and in no way deserved this. I rolled the liquid in the glass before throwing it back along with my foolish thoughts. A good scotch should be drunk slowly but this was the not the time for that. I poured myself another.

"I done some fucked up shit. But I would have never…" I turned to look at them not finishing my sentence. Honestly, if I had the chance with Blair I might just take it too. Forbidden fruit and all. Serena was crying as she often does and Nate was holding her close.

"We feel shitty enough Chuck. Don't act like you haven't done some shady shit on your own. You are Chuck Bass after all" Nate spat.

Internally I was a bit surprised at his outburst but I kept a cool facade and ignored him. "I thought you were away at school? Well I guess things were getting a bit boring with you away and all. I can see the GG post already. Spotted Our It Girl is fucking our Golden Boy. Guess our Queen was a little too virginal and frozen for Golden Boy" I laid into them.

"Chuck, fuck man. Let up. You know how many girls you screwed in the Upper East Side alone."

"Not a single one was my girlfriend because Chuck Bass doesn't do girlfriends. O wait you never slept with your girlfriend either"

"Both of you stop fighting. Chuck is right this is wrong. The Shepard wedding was wrong this is wrong. Blair is my best friend.

My phone ringing cut off Serena thankfully. IF she said the word wrong one more time, I would have just walked out. Noticing it was Blair I thought about hitting ignore but she is like a bloodhound and I figured I would get it over with now.

"Bass. Did you find him? Is he still alive? Cause if he is I am going to wring his neck for not being here. Did you see the blast? Serena was spotted in Manhattan. If she thinks she is going to waltz right back into the UES and everything is going to be normal she is wrong. I am queen now and she is…"

"She's with Nate and me," I directly told her. My motivations unclear even to me. The blonde-haired people looked up in horror at me with the realization that I meant Serena.

Clearly surprised Blair flattered and stuttered "sh-she is ?" Sounding her age- the sixteen-years young- that we were for the first in a long time. I knew that the thought of Nate and Serena being alone together was suspicious to her because she was all too familiar with their looks at each other before Serena fled to boarding school. I instantly felt sick at the thought of causing her pain. It was a feeling I have never felt before. The ache felt like the embarrassment I felt when my father has to bail me out of trouble but also with a sense of protection that I have felt only for Nathaniel.

"Yea we will be there shortly. Bye" I hung up before she could say anything else. "Wipe your tears Serena we have a party to attend. Before we get there, you two should decide your next steps. Tell Blair of the affair or lie about it. But both of you have horrible lying abilities I shudder to think of what you will come up with. So choose wisely."

"Chuck, why did you tell her we were together? What happened to my man, bros before hoes?"

"Have I taught you nothing? The best lies combine a bit of the truth. Would you want to risk that there is no photo of you two entering the Palace together or if no one will snap one leaving. Gossip Girl is sniffing around for another picture of Serena in Manhattan. You can say you had a drink in the palace bar if Blair asks where you were." I shook my head knowing Blair would have instantly understood this concept.

"I am not dressed for a party. I should go see my mother and Eric first anyway. Nate we should tell her first chance we get together. I don't want her to hear this from anyone else," Serena said before glaring at me. Clearly thinking her stern stare could frighten me. The ditz. I pinched my brows together thinking of their stupidly.

"I can hold my tongue. You think this is the first time I had a front row seat to you two. The bar stool was a bit adventurous for a first time Nathanial but I figured you were following Serena's lead. But it was quite a show. I just assumed the guilt made S flee and never return. But here you are once again on top of dear old Nate. I guess the guilt wasn't too strong. Don't worry I've kept my mouth closed for quite a while." Embarrassed they looked away.


"1136 Fifth Avenue right by Central Park" Nate angrily told the yellow cab driver and all together ignored my request to wait for Arthur who was probably only moments away in the Palace parking garage. Apparently, Serena was staying at the Palace with her family as they renovated their penthouse.

"Now you are in a rush. So we have to drive in cheap plastic and tin," I grimace as the smell off knock off perfume engulfed my senses as I slide across the plastic.

"I don't want to hear about your fucking limo right now dude. And since when are you one of Blair's minions?"

Pink bubblegum stuck behind the driver's head. The creative gum artist had arranged pieces to form a smiling face. Currently, the only smile in the vehicle since Nathaniel seemed to be mad at me and the driver looked worried as if we were going to have blows.

"I do no ones bidding. But if my suit gets stain from these seats I am sending my dry cleaning bill to you."

I was trying to avoid this conversation not wanting to further understand my own feelings or this sense of protection I had for Waldorf that seemed to be getting stronger every day. Sure, we have all known each other since kindergarten but once the drugs, liquor and girls became my life three years ago I barely saw her as anything more than Nate's girlfriend. Recently in Serena's absence and Blair's rise to queendom of the Upper East Side, I admit she amazed me. At first, she ruled over Constance and then took over all the prep schools or the five families as she called them. I watched as she took down the skanks of Spence, the bitches of Brearley, and the Blair-clones of Chapin while Nightingale surrendered quaking at her feet. Within months of that, every matron on the UES knew Blair Waldorf and she was cementing her place on the boards of every major charity years before she submitted her high school transcript to Yale. I wondered what she would look in the Bass boardroom and I only could imagine what the she could do. The older executives would not stand a chance. Quickly I began to think of Blair on the table in the Bass boardroom and all the things I could do to her. I felt the tugs of a smirk begin that I had to force down. Once again, I wished I were in my limo where I could have had yet another glass of scotch that I so desperately needed. Instead, I fiddled with my signature patchwork silk scarf. Silk that I could tie Blair up with. Fuck.

"Your hotel staff handles your dry cleaning. Stop mentioning the limo. You don't need to come around acting you saved the day with all your fucking money." Nate responding a bit late to my remark but I welcomed the distraction.

"Woah. Chill. Why are you talking about money? Lighten up. Besides you were the one just enjoying the riches of my suite."

Upper East Side 101: never talk about money unless you are in a business meeting. It is considered midtown to discuss money flow, which is why we dreamed up way to display our money through designer clothes, five star restaurants, and private jets that can take us to private islands. The silence made me slightly uncomfortable and I shifted on the fake leather seat.

"It's just…. forget it." Usually at this point in our conversations I would light a joint in the privacy in my limo I thought of mentioning this but I thought better of getting on his nerves knowing we were driving closer to face the wrath of Blair.

"Do you know what you are going to tell the misses?"

"I dunno know," shrugging it off as if he was running late because of traffic rather than sucking face with his girlfriend's best friend. He questioned why I cared so much. I shrugged him off. "Serena wants to tell her together." He added later.

"I am not looking for the drama that is going to come with this. Blair has destroyed people with far less skeletons in their closet than you, my dear friend. Hey, if you want to whore around I can bring you to the best ladies. Hell, I have tried for years to get you to loosen up and enjoy women but you were strictly with Blair. But then you go for Van der Woodsen who is last season's news and probably not a top rate hookup since she is usually drunk off her ass when she is with guys." I paused. "But I can introduce you to these Russian twins. They know how to have fun."

"Serena will never be out of season," was his only reply and I saw that we just pulling up to Blair's building.

We hopped into the elevator quickly as Nate was acting like a bat out of hell. I abandoned my saunter to reach him after throwing a fifty at the cab driver. The ride was silent, as the attendant knew Nate well enough to know we were riding to the top floor where the Waldorf penthouse where Eleanor's party was in full swing. The doors opened to reveal a smiling Blair that was seething on the inside.

"Nate can you please join me in my room in a few minutes," she pretended to ask as she reached up to kiss his cheek. We all knew it was a demand. She glanced at me and acknowledged me with my surname then walked away. She looked sexy in her prim and proper black lace dress and patterned black tights. The heels, man those heels were going to haunt me. Sky-high black pumps.

"Maybe we should leave. Did I mentioned that the twins are lingerie models?" I offered to Nate. He gave me a smile before following Blair who looked too effing good right now. How he could have not sealed that deal yet was beyond me. Walking over to bar, I ordered the finest scotch. The bartender only hesitated slightly before realizing his place.

While Nate followed Blair I chatted with Kati and Iz who looked like Japanese dolls with the way they were dressed. Not in a good way. Lots of colors and even plastic jewelry. I tolerated them as they did me for Blair.

"Oh my god! Did you see Gossip Girl?"

"Someone saw Serena getting off the train at Grand Central." Why was she even on a train I briefly wondered? Commercial train travel was not a Van der Woodsen family trait.

"Of course. Things were getting a little dull around here. I am sure things are finally going to get interesting."

Why'd she leave? Why'd she return? Send me the deets. And who am I? That's a secret I'll never tell- XOXO Gossip Girl


"Where were you Nate?" I was staring down my boyfriend of forever trying to figure why he was with Serena only minutes before. I knew that the two golden blonde-haired people were into each other before Serena's disappearance. Well Nate made eyes at her while she soaked up the attention. It was simple, S was starved for attention, and Nate liked shiny things. AP psych 101. I was trying to keep my cool, not be a doormat, all while trying to sound confident. Being 21st women was tough.

"I bumped into Serena and we were starting chatting. Time got away from us and I completely forgot. I am sorry baby," Nate clearly trying to appease me leaned in for a kiss. I moved before he got close and turned my back to face the mirror.

"What did she say?" I really wanted to ask how my best friend was doing after a year hiatus but stopped myself.

"You can asked her at school tomorrow." Nate came up behind me wrapping his arms around my waist.

"School? So I guess she is back for good." I looked at him and our eyes connected through the mirror. "I love you Nate Archibald. Always have, always will."

"I love you too." Did he? Taking a deep breath, I turned to kiss him. I had to make him want me and ensure that he did not need to go anywhere else tonight. I pushed him back onto the bed and straddled him while grabbing the collar of his shirt.

"Blair..." he moaned. I smiled to myself as I kissed his jawline. When I felt him move his hands down to my shoulders I thought he was going towards my breast but he had other ideas. I was embarrassed when pushed me off him rather than grabbed me. "Your mom is downstairs with friends and half the fashion insiders. Shouldn't we get back?"

Knowing I was rejected. I moved away from him and stood up as quickly as I could. I walked back over to the mirror pretending to fix my clothes but everything was still perfectly press. Nate never passionately ruffled my clothing so they were as they should be. So instead, I looked to see what was wrong with me and for a second debated going blonde. I fixed my headband before I decided my skin was far too pale to pull it off. We made our way back down stairs and where I saw my minions in a corner awning over the designers in the room. My mom stopped us at the bottom of the stairs and asked to speak to me for a second. She guided me to the edge of the party before she began to belittle me.

"Dear, your friends are fawning over my guest. Really, are children being raised with no class these days? I do miss Serena she was always such a fun sprite at these things. Much of my design team was often inspired by her graceful line and youth."

"She is back in town mother. Just today and she would have come but she was busy unpacking," I quickly cut her off hoping this was not going to be another Serena love fest.

"How exciting for you. I see that you wore one of my dresses. Really, Blair you could have at least altered it to fit you better but rather I don't really design for your shape. Well next time then." She turned and reentered the party with another thought.

As I watched her walk away, I realized we were in earshot of two guest. Basshole and Marc Jacobs were standing there looking at me with shock and pity. I felt the bile rise to my mouth and the tears to my eyes. I quickly turned away and walked over to my minions not wanting to cause a scene. I knew if I were alone right now, I would have resulted to old harmful habits. As much as I wanted to, I feared Bass would follow me if I did. It was some minutes later and after a lively discussion it seemed with Marc that Bass walked over to us. I purposely walked away from them to the bar to grab a drink. He walked up right behind me, placed his hand on my back, and whispered into my ear "Your mother is a bitch who clearly cannot see beauty. I would love to rip that Waldorf original to shreds and stare at your perfection."

"Gross Bass." I ignored him knowing he meant it as a sexual innuendo thinking it was one of his cheap lines that he throw out to keep up his reputation. As I turned to push his hand off, I made contact with his black dark eyes that were boring into me clearly with lust. My first thought was Bass would definitely make sure my clothes were wrinkled by the time he was through with me. My cheeks reddened at the thought. Chuck just ordered me a martini with two olives and another drink for himself. He probably knew I was only going to substitute the drinks for dinner. He liked to get under my skin in that way. On the other hand, maybe he just knew me too well.

"Did you see S?" I asked hoping to get information out him since Nate proved unhelpful yet again.

"I did. She is staying in the Palace while her mother redecorates. Maybe I should be neighborly and see if she or Lily need any cream," he lecherous smile. I stared him down clearly annoyed by his comments. "What I never told you about my Anne, Eleanor, and Lily dream?" he playfully asked.

"Chuck!" I tried to be angry but just giggled as Bass laughed outright. I realized that my face felt a little uncomfortable laughing once we were done. It had been awhile since I was able laugh to like this.

"I saw you chatting up with Marc Jacob like you were old friends."

"He saw I had style with a little bit of bad boy edge as he said. He is looking for his next line to mix grunge, prep, and couture. Sexy without giving a damn he said. Apparently, I have I mastered the cool but bored look without being too perfect. I think they were complements but he is looking for a couple for his new younger look to be his inspiration."

"I see so sleaze is back in style?"

"Was it ever out? I just wonder if fashion muse will look good on a resume?" he joked.

"I am sure all of Bass Industries will be wearing Chuck inspired items in no time. I am not sure if Bad Bart Bass will improve. Then again, once he commented that you shouldn't wear purple in the 6th grade it was like Barney threw up on you and that was all you wore. So he should know better now," He laughed again and I could not help the small snort in my laugh that I try to cover in public. This made Chuck laugh harder, which gained the attention of our friends and the room.

"What are you guys laughing about?" Nate asked with Iz and Kati in tow.

"Chuck's love of the color purple and all things fashion."

"Confidence is the key when those around us cannot see perfection," he winked at me. My cheeks flushed which surprised me. I told myself it was hunger and alcohol that made my face hot and stomach tingle.

I realize later that for the first time tonight my troubles with Serena, Nate and mother were out of my mind due to Chuck Bass. The Basstard.