A month later

Disclaimer: If I did own it, CB would be married by now. Grins.

Notes: Sorry it took me forever to do this. I keep forgetting I have 2 gossip girl fics to finish ugh. But thank you so much in advance for the interest and reviews!

Thanks to my beta and idea popper, Jackie!!

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"Mmm, you look ravishing… if I was your man, I wouldn't need clues to find you."

Blair looked over at him and gave him a disgusted glance.

"You'll ravish me, I'm sure." She kept her mask up as she looked around for Nate, but she was fully aware on how amazingly dashing Chuck was tonight. He was wearing all red. His pants, his jacket and his devilish mask were red and it matched his demeanor perfectly.

The dashing devil. That was his nickname for that night.

"Go look for Nate, he's late and I'm loosing heat!"

Chuck whipped his head to look at her and quirk a brow under his mask. Shit, she was standing in black looking so sexy. He was gaining heat just standing next to her. He shook his head, shaking the thought out of his head. She made it super clear two months ago that she wanted a serious relationship with Nate and to stop their mistake.

Chuck scoffed. Mistake. That's what Blair thought of it.

XXX XXX XXX

Flashback. 2 months ago

"I am serious about him!"

Chuck looked at her incredulously, "Really?" he quirked a brow, not believing a single thing she said. "I recall you calling him a boring ol' confused tool who looks blank most of the time."

"He's a confused tool yes, but he's super sweet! And he really likes me!" she defended Nate. They'd been spending a lot of time together since the party, and she was determined to make herself like the boring man. Chuck cherished Nate and all but the man was an idiot sometimes. He wouldn't know south to north!

"Yeah, because he's confused." He rolled his eyes. Blair fumed as she glared at him.

"I want to date him. A nice man, who likes me for me! He treats me like a princess, Chuck! And I'm against cheating! It's disgusting and immoral!"

"Much like yourself." He smirked. Blair walked over to him and stomped on his foot angrily. He yelped as he jumped back from her. "What was that for?!" he shouted.

"For being a jackass!" she screamed back. "This whole thing is wrong, Chuck. Wrong! Have you ever wondered how WRONG this is? We're best friends!"

"With benefits," he added.

Blair's eyes widened, "No! We should just be friends! Friends! Best friends! Plus, I've liked Nate since we were kids! I'm glad he asked me out, I'm glad he confessed to me. So I don't want you to mess this up for me!"

"He… confessed?" Chuck asked in a low voice. Did Nate Archibald really… confess that he liked her? Did he even like her?

Blair smiled triumphantly when she saw Chuck's features falter and she didn't know why. "Yes. He said he likes me. We kissed, we held hands. He told me he likes me. And honestly? I like him too!"

He quirked a brow, studying her. "No you don't. Not that much at least."

She clamped her mouth shut, then opened it again, "I like him, Chuck. Accept it. Accept that I don't want to… make out with you anymore, or do anything of the sort. We're best friends. I don't know why I continued experimenting with you until now. I should've stopped when we first kissed at 14. I want to find out whether this relationship will work out… I know it will! Nate is everything I've dreamed off. Handsome, rich, smart." Chuck scoffed at every single word, "Plus he was my first kiss. When I was eight…." She sighed thinking about it.

"Seven."

"What?"

"Your first kiss was at seven," Chuck reminded her, his eyes suddenly darkened as he stared at her as if prodding her to remember something.

"Oh…" she frowned, "Yes… Yes, seven." It looked like she remembered. "He was so cute hiding behind his thick scarf, and he kissed me."

His entire demeanor faltered, and his face was replaced by annoyance and anger.

"Yeah. You go be happy with Mr. Stepford; make little babies and buy a big white house and be a miserable boring housewife with him. Who knows, maybe you'll learn how to knit," He said nastily.

"He's a better man than you ever will be, Chuck. At least he doesn't sleep around."

Chuck frowned, "How did my hobbies find its way into your equation?"

Blair just glared angrily at him, wishing he would burst into flames, then she let out a frustrated cry, before turning around and walking away from him. Leaving him standing there, confused.

What the eff?

End of Flashback.

XXX XXX XXX

Since then she was trying her best to shack it up with Mr. Prince Charming.

Chuck was still very much pissed at her for forgetting their first kiss.

If she wanted her prince charming, she's on her own. He spotted a very beautiful blonde across the room wearing yellow.

"First things first," he said as he walked past her to the blonde bitch. Blair felt herself fuming as she watched Chuck walked towards the girl and put on seduction mode.

"Ugh. Pig," she muttered under her breath. She didn't know whether she was mad at him for not helping her find Nate…. Or for ditching her for a blonde.

XXX XXX XXX

Ring ring. Ring Ring.

"Scuse me," Chuck pushed the girl right off him to grab his phone at this vanity table butt naked.

"Hey!" she protested angrily. They were in the middle of having sex when he just pushed her off him to grab his phone. She was annoyed as she waited for him on the bed.

Chuck didn't even have to check his caller ID to know who it was. It was 1am in the morning, who else called him at this hour?

"Yes, what is it princess? Another Archibald disaster to save?"

"Oh? Another whore to tend back too?" she shot back. "I saw you go back with one after the party. Blonde-."

"Brunette. I left with a blonde ended up with a brunette." He corrected her with a smug smile.

"Ugh, you are freaking disgusting," he heard her disgust on the other line and chuckled.

"But you need me, evidently, if not you wouldn't be calling me at such an hour. Therefore, care to tell me as to what pleasure do I owe to receive this call from you?"

Damn, Chuck Bass knew her well, and she hated and loved it at the same time. Who else could she call at 1 am and still had the balls to joke around and tend to her? Definitely not Nate Archibald.

"It's Nate."

Chuck rolled his eyes as he walked over to this bar (still butt naked) and poured himself a drink, "Well obviously. What else could it be about? Nothing important, evidently, " he said sarcastically.

"I can't find him. We went to the party together and somewhere in the middle of my mingling I lost him."

"Blair, I haven't installed a tracking device on him. If you want to do it, go buy one and stick it on him. God knows he won't notice it at all. You know how clueless he is."

"You don't understand! Tonight is the night!"

"The night you lost your boyfriend in the crowd?"

"No idiot! The night we… we do it!"

Chuck pursed his lips, "Spare me the pre-school talk, Blair, we're all adults here, you mean sex."

"God! Don't you know anything about discreet?"

"Come on, say it. S-E-X."

He heard her huff angrily on the other side. "Are you done mocking me?"

"Not even close," he chuckled. "Listen you didn't call me to just complain. Although, that is what you do on a daily basis. Now please entice me with something I actually care to listen about?"

He heard Blair grit her teeth on the other end, and he tried to stifle his amusement, "I want you to call him and ask him where he is."

"Can't you do that yourself? You are after all his girlfriend." He basically spat out the word.

"I can't! It'll make it sound like I'm needy."

"Which you are."

"Are you going to help me or not?"

He sighed. Chuck Bass didn't do what people tell him to do if he didn't want to do it. But when it came to Blair, he always did it. Minus those few random moments where he'd just ignore her and do other things. However, this time around she sounded like she needed his help desperately, and Chuck was her best friend; he never bailed out on her.

"Fine," he said. "But, on one condition."

"Well, obviously. You can never do something sincerely for once. There's always some odd perverted condition," Blair said, obviously relieved he asked for something. If he didn't then she'd know he was mad or something. It was abnormal if Chuck didn't ask her for anything.

"You know me well," he smirked. "If he picks up I'll tell him to pick you up and he can whisk you off to do some friendly boring activities."

Blair rolled her eyes.

"If he doesn't pick up…." His silence trailed after what he said, and Blair was getting impatient. "If he doesn't pick up... I will come and get you and we can do some friendly activities of our own."

He heard Blair gasp in disgust on the other line. He chuckled. How could she be surprised at this request? Had her time with Nate made her stupid and clueless too? He'd have to salute Nate if he managed to make her as clueless as he is.

"You. Are. A. Disgusting. Creature!" she spat out every word loud and clear for him to hear. Oh, Chuck has heard all of this before. Since when they were kids. She'd call him names, he'd smirk. She'd piss him off. He'd get annoyed. They fight, and still stay best friends. They had a very odd friendship, but it worked.

"Yes or No answers only, Waldorf. Take it or leave it." He finalized that conversation for her. He couldn't hear Blair seething on the other line, but she gave him a disgruntled answer of a 'yes' in the end.

He laughed again when he heard Blair bitch about his conditions.

"You do know this could've been avoided if you called him yourself." He told her as he walked over to his hotel phone and dialed Nate's number.

"Whatever. He's going to pick up. If fate permits it, he is going to pick up. Which is why I'm not worried at all," Blair said a little bit too confidently.

"Overconfidence gets you nowhere Blair," he told her as he held the other phone to his ear.

"Obviously not. Look where it got you Bass," she spat back. He chuckled again. He loved bickering with his best friend. It was much more amusing than his sex with his current flavour of the night. Speaking of which… he turned to look at the girl smoking on his bed.

"Pardon me, but I have more important matters to tend to, we'll catch up soon…I'll call you later," he told her sweetly. It was a lie; Chuck Bass never called a girl. The girl smiled and slid off his bed naked to get changed in his bathroom. Ah, cheap easy girls. How they bored him so. He needed someone feisty… someone challenging… someone like his best friend.

"Got rid of your latest whore?" he heard Blair's voice through his cell phone.

"Gracefully. Are you relieved?" he questioned her.

Blair scoffed, "I don't care what you do or do not do in your spare time." Although deep down she was happy that he sent his latest whore home. But she will never ever admit it.

He chuckled again. His ear against his other phone waiting for Nate to pick up, but he never did, it went straight to voice mail. Chuck frowned, what was Nate doing?

"Hello Chuck? Did you call Nate yet?" Blair was still on the line with him.

Chuck was stuck should he or shouldn't he tell Blair Nate wasn't picking up?

"Uhm, no. Not yet," he chose the higher path. Damn you, Bass. "I was getting rid of my whore, so to speak. I'll call him now." He lied as he dialed Nate's number again. He didn't know why he was doing this for Blair or Nate for that matter. Where was he? And why was Blair hell bent on choosing him as her 'one'? It bugged him that she wanted Nate to be the one to deflower her.

Oh yes, Chuck knew very well she's still a virgin, and every fiber of his being wanted to be the one on her special night. But he gritted his teeth, shaking the thought out of his brain. He is her best friend, such thoughts are preposterous… then again he is Chuck Bass… no thoughts are preposterous enough…

Back to voicemail.

What the eff is Nate doing? Chuck thought exasperated.

"Blair, Nate's not picking up," he finally told her.

"You're lying."

"No. I'm not. I called him twice he's not picking up," he repeated again.

Blair was silent for a while before answering, "You're not lying are you? Just to make me loose, so you can come over and—,"

"No, I'm not lying," he said, cutting her off. He was annoyed that she didn't believe him, and that he would be unscrupulous enough to not call Nate… which he is capable of doing… so he couldn't blame her. He heard Blair sigh sadly.

"I'm still at the party. Hurry up and get me," she said before putting the phone down.

Chuck sighed as he got off to get dressed. Blair really liked Nate is that it? She sounded devastated when she heard that Nate wouldn't be coming. She was seriously trying to make this work, didn't she? He watched them frolic together for the last 2 months, just watching closely over Blair hoping Nate didn't hurt her, and so far they look like the happy perfect golden couple. It bugged him, but it didn't hurt him, not yet at least. Why should it? He's just watching out for his best friend.

It didn't take him long to find Blair outside the hotel in which they had the party in. She looked bored and sad. Damn Archibald, where the hell was he?

"Hey," he came up to her.

"Hey," she said looking up at him.

"Want me to take you home?"

"There's nothing else to do," she shrugged then sighed, "I can't believe I lost my boyfriend in the party. I'm so mad at him right now. I want him to suffer tomorrow."

This is the Blair he knew. He chuckled, "Well, I'm sure you'll do a good job of it."

"He's such an idiot sometimes." She shook her head as she slid into the limo, followed by Chuck.

"That's Nathaniel for you. Sweet and dumb. It's a package, ma Cherie."

Blair smiled and moved closer to him, "Thank you for picking me up."

"I'll pick you up anytime," he said inching closer to her.

"Uh uh, Bass, I'm not cheating." She pushed him away. "Whatever we had before I had a boyfriend was just experimental."

Chuck's jaw clicked, but he nodded, "Just experimental."

"Never to be repeated again."

"Definitely."

"You're my best friend, and I thank you for teaching me uh, things." She turned slightly red.

Flashback.

"Happy birthday, Chuck!" Blair greeted her best friend out at the balcony. They were both at Chuck's 14th birthday party.

"Came to give me my present?" he asked her with a cute grin.

"What present?"

He inched closer to her, "You know. A kiss. We talked about this before. I want a kiss from you."

Blair glared at him, "Yeah but I didn't say I was going to agree!"

"You were interested at that time though. You know. When your other best friend was kissing the life out of that new kid."

"Serena's been whoring since I can remember," she said angrily. She hated being outdone by her. She loved Serena cause they're best friends but she hated that Serena could do everything better. She was the prettiest, she was well liked…. It was annoying.

"Besides, you should try it…"

She sighed as she finished thinking about it.

"This is strictly because I want to learn."

"Learn what?"

"Learn, you know!" she hissed. "Argh! You know… kiss…. To kiss like a woman,"she said meekly.

Chuck burst out laughing, causing Blair to turn red and grab her bag to hit him repeatedly.

"You are an evil mean jerk! I wish I didn't ask you this!"

"Ow! Ow. Stop hitting me! Fine, I'll teach you. What normal 14 year old doesn't know how to kiss?"

"The ones that hadn't lost their virginity in the seventh fricking grade!" she nearly shouted. Chuck laughed again. Blair was cracking him up today.

"Fine."

"STRICTLY experimental learning. We're still friends. Nothing more! Nothing less. Got me?"

Chuck stared at her, refusing to answer at first. He loves kissing Blair, it's a different feeling, its WEIRD kissing his best friend though… Maybe if they were more….

He felt a painful tug on his hair causing him to yelp.

"Got me?" she was still gripping his hair tightly, inflicting pain on him.

"OW OW, fine! Shit, if you wanted to do the crash course and inflict pain on each other while giving pleasure you should've just asked." He rubbed his head.

Blair's eyes widened, "What the hell have you been doing Bass? How can you feel pain AND pleasure at the same time?"

Chuck smirked, "Trust me. You can." Then he walked closer to her and slid an arm around her waist as his other hand tilted her chin. "Pain and pleasure, you'll feel it one day." And with that his mouth covered hers, and Blair experienced the best thing she'd felt since she started eighth grade…

Bliss.

End of Flashback.

"Apparently I didn't teach you enough." He smirked thinking about he first time they became make out buddies. Blair rolled her eyes and threw her clutch at his face. Chuck caught it, laughing.

"How can this friendship even be normal?" she asked rubbing her forehead.

"It's not. That's the beauty of us, Waldorf." He smiled at her, and she smiled back. They halted to a stop. He leaned down, and before she could protest, he kissed her cheek. "We're here."

She turned red again before grabbing her clutch and sliding out of the car. Suddenly her phone rang and she hoped it'd be Nate, so she can put him in his place, but the caller ID clearly said Serena.

Blair knew where this was going.

"S?"

"BBBBBBBBBB!!" she heard Serena shriek on the other line.

"Where are you, S?"

"I dunno, B," hic, "Where are YOU?" she asked, then it followed with a hiccup. "I… I don't know. I just see your …" hic, "Mom's store across and I thought …" hic, "…of you!"

"What? You're walking down the streets alone, drunk?" Blair shook her head, how could she be surprised? This ALWAYS happened.

"I dunno I see…" hic, "Waldorf on this store, seems like your mom's store. Should I…" hic, "go in and say hi to your mom?" hic.

"It's 2 am in the morning, S," Blair said boringly. She was tired of Serena's antics. She always did this every other night. Getting drunk, and it wasted Blair's time because she always has to pick her up and look after her. Lily would be mad at Serena for acting out and might send her to boarding school to which she has threatened her with more than once. "Know what… you go ahead and say hi to my mother. But STAY where you are okay? I'll come say hi with you."

She turned around, glad Chuck didn't leave yet.

"Serena."

It just took her name for Chuck ask, "Where to?"

XXX XXX XXX

"BBBBBBB!! I couldn't find your mom!! She's not opening the door… the… door?" she pointed to Eleanor Waldorf's store.

"Still stupid," Chuck watched a drunk S twirl.

"At least she stopped hiccupping. It's easier to understand her this way." She walked over to S and grabbed her. "Come on, let's go."

"Waiiitttt we have to look for Natie!" she persisted.

"What?" Blair stopped to look at Serena.

"I dunno. I was with Natie… then I think I lost him," she pouted.

Blair frowned, "Nate… Nate was with you the entire night?"

Chuck figured they were. He stood behind them, watching Serena make a fool out of herself, and watched Blair slowly let it sink in.

"I think so? I told him I got bored of the party and decided to go somewhere with louder music! And Natie said, OKAY! I'll come with! Then we went then I lost him." Serena looked terrible and hazy, as she looked up all confused. "Or he lost me. I dunno." She started giggling. "But we have to look for Natieeee," she bugged Blair who was looking very tired and slightly angry.

She let go of her, letting Serena fall face flat on the ground.

Chuck watched the blond fall mercilessly on the ground, and then watched Blair walk quietly past him. He smirked and shook his head. Nate always preferred Serena over her. The four of them were the non-judging breakfast club. Always together, but always messed up.

He walked over to pick Serena up and led her to the limo.

"CHUCK! Chuck is that you?" she screamed into his ear. And he half contemplated to drop her back on the floor. He put Serena into the car where she automatically fell asleep after touching the soft leathery seat.

She started snoring.

Chuck and Blair sat next to each other watching the blonde bimbo snore.

"Well, at least we know Nathaniel didn't go missing," he started.

"Don't. Chuck," she stopped him from continuing. Her arms were crossed and she looked annoyed.

He chuckled, "Some things never change." He looked at her. "You look hot when you're annoyed."

She whipped her head to look at him, and she smirked.

"Is your condition still on?"

He smirked back, "Always."

And with that, Blair grabbed his collar and kissed him fiercely. Chuck grabbed her waist and pulled her against him. He kissed her back with the same intensity. They've been missing their make-out sessions because Blair decided to get a boyfriend, but that went down the drain now.

Serena stirred slowly, and it made them both stop sucking face (lips still stuck together though) and watched Serena move around a bit…. Then she finally fell back to sleep.

They both laughed quietly before resuming to their previous position. They didn't get far because they reached Blair's place sooner than expected. His driver came out to take Serena up to Blair's place.

"Shit. I didn't manage to get to third base," he muttered, taking his hand from under her dress. Blair giggled as she slid out of the limo. She could barely stand after their rendezvous in the limo. She had to admit that Chuck's kisses were fricking orgasmic.

"Are you and Nathaniel done?" he asked her, smiling. Already knowing the answer.

"No. Not really."

Chuck stopped smiling. Apparently he was wrong.

"But it would seriously hurt him if he found out about this wouldn't it?" she let out a whoosh of air before smiling widely. "Besides I needed that. It was… up lifting." She smiled at him.

"You're a bitch," he said slowly. "But I wouldn't want you any other way. Until our next kiss." He winked. "You'd have to settle for Nathaniel's boring ones."

"Mmm and you'd have to settle for everyone else's, since this won't be happening again. Have fun with your latest whore, Bass." She rolled her eyes, knowing he would call up one of his call girls and whore it out Bass-style. And she hated it.

"I will. They're there for me to have fun in the first place, and are you sure it won't happen again? Seemed like yesterday you said the same thing."

"Goodnight, Bass," she accentuated her goodbye.

"Goodnight, Waldorf," he flashed a small smile at her before closing the limo door.

She watched his limo drive off, and sighed. Why she played this game with Chuck, she didn't know. But whatever it is, she missed his kisses.

Right now she had another man that needed to feel her wrath and a best friend that needed sobering up.

XXX

A/n: Yeah remember all of this is AU, so things might be a little off. Hope you guys liked this one! So much for CB cutting off their FWB friendship. Lol.