Disclaimer: Nate is cute, Chuck is sexy I don't own Gossip Girl and neither do you!

Warning: This is rated 'M' for a reason so if you don't like sex, drugs or words that rhyme with 'truck' and 'blunt' then move on!!

Chapter Four - Understanding.

Authors Note: I was asked about S and K, They are from the film Cruel Intentions, if you haven't already watched it then you so should It's amazing and utterly heartbreaking. I'm planning on writing a gossip girl fic based on the story line of C.I read more below.

Gossip Girl here only bringing you a small message.

Were we wrong about J having Damon as a lover? If not then I'm not sure he'll be pleased about this! Spotted none other then J and the devil himself C sipping scotch at the Palace Bar, What's going on here then, Are they really picking up from the Kiss on the lips party? I don't think so, Perhaps planning a scheme? I don't know you tell me, Get your shovels out and start diggin UES, this bit of drama is something everyone wants to know.

You know you love me

XO XO Gossip Girl.

Jenny chuckled at the most recent post on Gossip Girl before sliding down her phone and turning attention towards Chuck who was staring off into the distance, With a look Jenny had never seen on him before; It actually made him look human.

"Ok Chuck what's so important you had to drag me down here?" Jenny asked feeling kind of pissed off, Right about now she wanted to be in her nice pj's tucked up in bed listening to some music before drifting off into beauty sleep. 'ahh'

"I erm, Well it's just erm." Chuck stuttered caught off by Jenny's voice, He was shocked she'd even agreed to meet with him.

"Wow Chuck Bass stuttering? That's something I'd never thought I'd see!" She laughed amused, her head throwing back.

Chuck felt a burst of anger shoot through him, Who did she think she is to take the piss out of him? Wow she lived in the UWS but that did not give her a right to laugh at him when he was trying to do something right.

"You know what Little J, screw this. I went out of my way to try and do something right and you throw it back in my face!"He snapped.

"I'm not Little J no more Chuck! You're lucky I even agreed to meet with you, You know what screw you, Why don't you piss off!"She snapped back

Both of them were pissed off now.

"No why don't you piss off back to your sugar-daddy!" He barked.

"Funny Chuck, I got two dad's and they both care about me, Your dad couldn't give a shit about you!" She snapped.

"Low blow Jenny, You don't know anything about my father!" He barked.

"He's an old stuck up prick who doesn't care about his own son and fucked off and left him here whilst he ran off with some twenty year old tart!"

"Jenny shut up!"

"No Chuck you shut up!"

"Your a little Brooklyn wanabe, You may live in this world now but you're nothing!"

"So fucking what if I'm from Brookyln, At least I have friends, real friends Chuck not people I buy with my money." She hissed out with a laugh.

"You think you're fucking special Jenny, But your not; Heck Nate ditched you for Vanessa of all people what does that say."He laughed dryly.

"Screw you Chuck." She whispered biting back tears.

"What got nothing to say back J? I'm surprised he even looked at you twice, You're nothing, Just another notch on his bedpost, Another girl to had to the list, Another girl for others to point and laugh at, Have sympathy for, Face it J your a nobody if it wasn't for me that night of the Kiss on the lips party you wouldn't be known, I done you a favour.!"He barked laughing loudly.

Jenny sat there tears streaming wildly down her face, Nothing matched the embarrassment that she felt right now, Did people really laugh at her? Talk about her behind her back? Everything he said was true, she didn't have nothing to say back to him so she knocked back her scotch and stood up grabbing her clutch.

"Your right." She whispered out, her voice now cracking. And then she walked away leaving Chuck alone.

He was shocked he didn't think she'd give up that easily, He didn't think she would even give up at all, But then he remembered his words to her about Nate, Brooklyn and...The kiss on the lips party, Immediately he felt guilty he had got her down here to apologize for that night instead he ended up throwing it in her face saying she owed him, And why? Because she laughed at him stuttering, Which is rather funny.

'Oh shit what have I done' he thought to himself gathering up his stuff and attempting to chase after her.

"Jenny wait!" He shouted as he shot out of the bar and towards the reception where he spotted Jenny stepping into an elevator, He quickened his strides but did not make it in time so he headed towards the fire escape and flew up the stairs if anyone was to see him now they'd probably think he was crazy, Chuck Bass did not do crazy, He always calm, cool and collected. Stopping n the 6th floor catch his breath he rushed out and towards the lift his chest heaving in frantic breaths.

"Come on come on!" He hissed repeatedly pressing the button for the 23rd floor, As soon as the lift dinged signaling him that he was at his floor destination he shot out and up the stairs towards her bedroom only to find sobbing into a pillow.

"Jenny...."He trailed off in an unsure voice, He was never good with situations like this, Never having to really go through them as he didn't ever let himself get close enough to a female, never having a mother figure nor any siblings, And technically not any female friends.

"If your here to rub more salt in the wound Chuck, Then don't bother it won't work." Her muffled crys was like a kick in the balls, Not knowing what to do he walked over to the bed and perched himself on the end facing the door

"I thought I told-" Jenny started in an angry voice, shuffling about on the bed but was cut off by Chuck.

"You're right,"He said still staring straight a head.

"I'm jealous, Me Chuck Bass jealous of little Jenny Humphrey. Your so lucky Jenny you don't understand, When you left you Dad was devastated and a wreck for quite some time, My Dad? He wouldn't have been bothered hell he would have probably been the one who suggested it, You have a Mom who loves you shows you right from wrong, Comforts you in bad situations, Point you in the right directions and make sure you make the right choices, Me? I don't have a Mom she died giving birth to me." He said seriously still not making eye contact causing Jenny to feel awkward.

"I'm sorry Chuck, I didn't know."

"No of course you wouldn't, I don't talk about it, And even if I wanted to I wouldn't know how, From as young as I can remember my Father learnt me to bottle things up and push my feelings aside, If I needed comforting I would be laughed at and told to 'Suck it up Chuck', I've never had any type of a stable relationship with anybody because I was taught not to, My Father hates me and blames me for my Mothers death, So he avoided me as much as possible making sure he was never around, I was practically bought up by the maids." He stopped again to take a deep breath.

"I had a hard upbring and have so many expectation to live up to, But then my Dad met Lilly and everything seemed to be going good for once, He actually listened to my idea's, Then he had to go and screw that up. And it hurt. I was finally feeling accepted and getting the idea of what having a family feels like only for him to ruin it. You Jenny are so lucky, You have a Mom and Dad who would do anything for you, Then Step-parents who love you just as much, I'm not sure about your step-father as I've never met him but Lilly? She thinks of you as one of her own, Like your her second chance, She was never there for Serena so she hopes to be there for you, And then Dan," Pausing one more time when he felt Jenny take his hand and give it a reassuring squeeze.

"I've never seen a sibling bond as strong as the one you two share, He's always going to be there for you, I've never had a sibling but this past year I've got the idea of what it feels like and it's amazing, Having someone to turn to, them coming to you for advice, Covering for each other. You walk into this apartment and it reeks family, It's in the atmosphere, even when you guys are arguing, I grew up in an empty house never had a brother to play foot-ball with or compare girls with, A sister to protect, And go out and kick some guys ass because he didn't treat my sister well enough." Chuck stopped to take a deep breath, Because he felt tears coming.

And Chuck Bass does not cry in front of anyone.

"Friends? I don't even know the meaning of friends Jen, I've always had to be careful because you can never tell who's your friends or not, If people are using me just because I'm loaded or if they genuinely want to be my friend, Of course I have Nate, But what does that say, One friend? You Jenny you have tons of friends, You should have seen how many people were upset about your departure, That's friends. And your respected by people because you don't give a damn what people think, I mean you were living in Brooklyn just a small freshman and you dethroned Blair when she was at top, you through that guerrilla fashion show and amazed people at just 15! Your respected, Me? I'm feared, people are nice to me and don't want to get on my bad side because they fear what I might do otherwise,"

"It's like when you done that fashion show when my Father and Lilly received an award you showed remorse and guilt even tho everyone love it and you done them a favour, But when I bought a building and had to kick out all the tenants not thinking about where they'd go, I didn't even feel remorse, Not the tiniest bit of guilt. You can actually have a relationship with someone, but before I even introduce myself to some one my palms are sweaty and I feel nervous, Not for the same reasons you would, You fear you'll be rejected, Me I fear that I'll be accepted, People letting me hurt them, And as soon as the word commitment comes up I'm gone like a bat out of hell, You'd be overjoyed,"

"I mean look where everything got me with Blair? Sure it was for the best and looking back on it now we both agree what a disaster it would have turned out, But I didn't care that I was hurting her at the time, I was hurting Nate my best friend, I ruined Blair's fairytale if it wasn't for me those two would have their happy ever after, And I ruined that and couldn't offer nothing in return,"

"I crush people and don't care who I hurt as long as I get what I want, I can never let my guard down, Every-time I get feelings for a female I have to push them aside an end up hurting them, And I can't even apologize for it because I've never been taught to,I've always been an ass, But it's because it's what I do and know best, It's like people expect it from me, You know Jen, Tonight my plan was actually to apologize to you for what I put you through at that stupid party and the nightmares you probably suffered after, But then look what happened all you said was about me stuttering and I blew up, But looking back now it is funny cause hell I'm Chuck Bass and I fucking stuttered." He laughed harshly

"Your lucky Jen," He said taking her other hand and now looking straight into her eyes, Her big blue lapis lazuli eyes, Where Jenny could see the tears brimming and threatening to fall over his now red lids, But what scared her the most was his eyes, They were so hollow, And she almost cringed from all the pain and hurt that was shining through as if they were projectors.

"I'm so so sorry Jen, for everything that I must have put you through that night and after." He said sincerely tears now streaming slowly down his face, he looked so...Vulnerable. And Jenny felt so bad, No one should ever have to go through what he was put through, And she now made it her mission to make sure Chuck felt equal and accepted.

"Don't be." She whispered pulling him into an embrace his head burried in her shoulder.

"I'll for ever be sorry to you, I could only imagine the pain and fear you went through that night, I was the predator that night and I've been living in pain just thinking about it and what could have happened.."He sobbed his back shaking as Jenny rubbed soothing circles on it.

She was shocked that Chuck Bass finally opened up to someone and let his guard down, But more so that she was that person.

"Do you want to stay in here tonight?" Jenny asked softly.

"Jenny I don't want you thinking that I opened up to you just so you would feel sympathy to me." He mumbled but still not moving.

"I don't Chuck, but I know that last year when I was feeling this down all I wanted was for someone to be there for me, To understand me like really understand me not just say they do, I used to get Eric to come and sleep in my room or I would sneak of to his room, And all though we didn't talk it was just nice you know? Knowing some one was there with you, And this bed is so comfy, And has more then enough room for me, It Plus nothing can beat my cuddles!" She grinned at the latter trying to lighten up the moment.

"What would your Father and Lilly think?" He said pulling his head back and now sitting up, Eyes still raw red.

"Well that's what locks are for, Plus it's so late by now that by the time we wake up in the morning no one will be here!" She smiled softly.

"Thank you for being here Jenny, And for really understanding me." He said sincerely pecking her for head and standing up to strip down to his boxers before locking the door and climbing into Jenny's bed patting the spot next to him for her to lay, Jenny smiled and turned off the lamp before dropping on to the bed, Only to be pulled to Chuck's side where he buried his head in her hair and inhaling slightly.

"Thank you for allowing me to do so, And for me being the one you could trust." She said snuggling closer to him, faintly smelling his Hugo Boss after shave, It was then she decided that it was her new favourite smell.

Both lay peacefully not talking just letting their minds drift off and enjoying each others company, It was then that Chuck agreed that Jenny's cuddles really were the best in the world, And there's no place he'd rather be then here.

"Jenny, are you still awake?" He whispered softly not wanting to wake her if she was sleeping.

"Mmm hmm." She mumbled.

"You know this is the first time I've done this."

"Done what?" She yawned confused.

"Slept in the same bed as a female, Of course I've shared beds but never through the night."He said amused

Jenny just chuckled in reply knowing what he meant, And was glad she was the first he shared this experience with.

"Night J." He whispered.

"Night Chuck."She mumbled shuffling closer to him when his arms tightened around her.

And that was the first night they fell asleep in each others arms feeling happy and content.

Gossip Girl here.

Spotted: A very heated argument between J and C in the palace bar, I wonder what happened there? I know your all dieing to know, I sure as hell am. Well that's Gossip Girl over and out, Goodnight Upper East Siders.

XO XO

Gossip Girl.

Finally! I'm sorry that it has taken me so long to update but I hope your happy with this chapter, I know it's very OOC for Chuck but like I've previously said It's my story and its very very A/U so what I say goes! It's not going to jump straight into C/J romance but it is the start of a beautiful....scheming friendship. Also very sorry about my grammar and spellings, I know they are preposterous but it's still understandable right? Good so review and let me know what you think! Also GLEE ahhh don't you just love it! Puckleberry - Yummy!

Gossip Girl / Cruel Intentions Fic - Currently in progress.

If you have watched the film then you'll understand, Chuck is going to be based on Sebastian, Blair on Kathryn and Jenny on Annette, And Eric on Blain - Because you got to love him. 'Oh Gregory!' LOL. I'm not sure how I'll bring everyone else into yet but I will! For those who haven't watched Cruel Intentions the plot is:

Kathryn and Sebastian, two wealthy, manipulative teenage step-siblings from Manhattan's upper-crust, conspire in Cruel Intentions, a wickedly entertaining tale of seduction and betrayal. Kathryn makes a bet that her step-brother, Sebastian, won't be able to bed Annette (a virgin, who wants to wait until marriage) before the start of the school year. If he loses, Kathryn gets his Roadster, if he wins, he gets Kathryn who he's dreamed of having as she's the only girl he can't have (playboy) and it kills him. But what happens when love gets in the way?

Kathryn - Blair.
Sebastian - Chuck.
Annette - Jenny.

Let me know what you think of this idea, It's been going through mind 24/7.

XO XO Chuck's Girl! ;-)