A/N - Here's a one shot of what might have happened in the limo between Chuck & Blair in season 1. This is my very FIRST Gossip Girl fanfic, and i really hope that you like it! :) REVIEW, REVIEW, REVIEW, please!! :)

I do not own Gossip Girl or the characters! If I did, CB would be together right now, and they'd stay that way :D

"Thanks for the lift home," she said, looking so beautiful in Chuck's eyes. Why hadn't he noticed this before?

"You were…amazing up there," Chuck said in a voice that conveyed that he was in awe.

Blair looked over at him, and saw something in his eyes. Something that she had practically been begging Nate for since Kindergarten – desire – and she just couldn't stop herself. She scooted across the seat of the limo, leaned up, and then kissed him.

Chuck pulled back quickly to look her in the eyes. He knew that, obviously, if she had been saving herself this long, after having the same boyfriend for years, then taking this step was special for her. He didn't want to just take that from her. She was his friend, after all. "You sure?"

And then her lips were on his. She leaned into him with her left shoulder, and very boldly, for Blair, reached up with her right hand, and ran it through his hair, and to the back of his neck as they kissed.

He knew that she was probably nervous, deep down, so he took a little bit of initiative, and put his arms around her waist before hoisting her up into his lap. He didn't want to scare her off, but he found this situation so hot. He was hard already, and to show her that, he rubbed himself against her thigh that was splayed across his lap. When he got a little whimper out of her, he pulled back from the intense kiss. "Blair, if we don't stop now, I'm not sure that I'll be able to."

Blair moved her body so that she was straddling him now. "Maybe I don't want us to stop," she said looking him squarely in the eyes as she rubbed her center against his growing erection. She threw her head back a little bit, and moaned his name quietly. "Chuck…"

Chuck's resolve wavered and he reached up to put his hands on each side of her face. He pulled her back down into another searing kiss while she continued to rub herself on him, eliciting a groan from somewhere deep within him.

After a few moments of this, Blair reached forward, mid-kiss, and blindly pushed his jacket off of his shoulders, and then throwing it to the side before starting to unbutton his shirt. He pulled back again, suddenly, and she moaned from the loss of his lips. "What now, Chuck?" She didn't mean for it to come out so frustrated, but Chuck chuckled a bit.

"Don't worry, Blair. I just need to tell the driver to keep driving around. I wouldn't want us to be interrupted, would you?" He asked with a smirk and a sweet kiss on her forehead. He slid the divider down just enough for the driver to hear him, gave him his instructions, and then rolled it back up again. "Now, Waldorf…where were we?"

"I think we were right about here," Blair said as she pulled him by his collar back into a deep kiss. Her eyes rolled back into her head a little bit as she felt Chuck's very talented tongue roll inside of her mouth. She frantically finished undoing the buttons on his shirt now, and then pulled it off of his shoulders before throwing it off somewhere – probably next to his jacket. She started to run her perfectly manicured nails down his chest, over his nipples, and down his abs towards the hem of his pants.

As Chuck felt her begin to undo his belt buckle, he pulled out of the kiss. "Tsk, tsk, Waldorf. It's your turn first," he said as he ran his fingertips down the front of her shoulders, over the lumps of her breasts, and then down her sides to the hem of her slip. He felt her tense up a little bit, and then remembered that she had issues with her body image. He realized that she was a bit nervous because he was going to see her naked, along with the fact that it was her first time. He had almost forgotten, considering how bold she was acting. He gave her a small smile before leaning forward, and kissing the side her jaw, and then down to her neck. As he felt her relax into him again, she slowly pulled her slip up her body, and then pulled back to pull it over her head…and when he looked at her, he froze.

Blair felt uncomfortable under his gaze, which ran up from her waist, over her breasts, and finally to meet her eyes. She suddenly felt a bit more nervous about being naked in front of him, and pulled her arms up to cover herself. He grabbed her arms, and pulled them away from herself while shaking his head.

"Don't. You're beautiful." His eyes raked back over her body, and his eyes rested on her breasts. "So, so beautiful," and then he reached up, and ran his thumbs softly over her nipples, causing her to moan out loud.

"Ooh, Chuck…" she called out. Her nipples became erect at the first touch, and she reached up quickly, and held tightly to his shoulders before burying her face in his neck. She brushed her lips over his pulse spot, and then reached a hand around to tickle his hairline, eliciting a deep groan from his chest. She ran her hands down to his waist, and blindly undid his belt buckle. Her hands shook a bit because of her nerves, and she hoped that Chuck hadn't noticed.

Apparently he did notice, because he reached down, and unbuttoned his pants before lowering the zipper, and then lifting up to push them down his legs. They fell around his shoes, so he moved Blair to the side so he could take them all off, and kick them to the side. When he was finished, he looked over to see a very sexy-looking Blair who was sitting up onto her knees, and lowering her stockings down her thighs. He leaned forward, and helped her to pull them off of her legs before tossing them to the side.

By this time, they were both sitting on the seat facing each other, naked from the waist up, and in their underwear from the waist down. Blair moved towards him, and with shaking hands, wrapped her arms around his neck before pulling him down so that he was lying on top of her on the seat. She pulled his face to hers when her nerves started to get the best of her, and captured his lips with hers again. Oh gosh, this is really happening, she thought. Is it supposed to be this nerve-wracking? But that was as far as she got before all of her thoughts went out the window when he started running his hands down her body.

Chuck's dick was so hard, he thought he might explode right then and there, but he knew that he couldn't rush this. Blair had never done this before, and he didn't want her to regret a single moment of it. This thought surprised him. Sure, he'd been with virgins before. Quite a few of them, in fact, but for some reason, Blair was different. He'd done it with "friends" before, and he never cared this much, but this time he did. He'd known her his entire life, and her friendship meant a lot to him. Right now, he was going to let that be his reason.

He braced himself over her with his right hand, while he brought his left one down to her left breast. He ran it slowly over her nipple, causing her to arch up into him. Man, that is so hot, he thought, and then he broke their kiss, bent his head down, and captured her right nipple in his mouth. He spent a few minutes just flicking and circle his tongue around that one, while his hand lightly tugged and teased her other nipple…then he switched. Another few moments later, and she was writhing around moaning his name.

"Chuck…please…" she moaned.

He smirked, and moved his hand down to brush over her center through her panties. They were already soaked. "Please what, Blair?"

"I need you, Chuck. Please…"

He lightly pinched her clit through her panties. "You need me, huh?" He hooked his finger into the front of her panties, pulling them down slightly in a teasing way. "What is it that you need from me, Waldorf?" He kissed her lips softly, and then looked down at her with his trademark smirk playing on his face.

Blair moaned. "I need you inside me, Bass. Please, just do it before I lose my nerve here," she said, giving him a meaningful look.

Chuck nodded his head, still smirking at her. "My pleasure, baby," he groaned as he sat up, and slowly pulled her panties down her legs, and then off. He looked down at her naked body, and groaned. His cock twitched a bit from just looking at her. "Fuck…Blair, you're so fucking hot." His cock was straining so much against his boxers. He stood up, and slipped them off before throwing them aside with the rest of their clothes. When he turned back, he noticed that Blair had stiffened.

Oh, God…he's so big. Is it even going to fit? She wondered. She looked up to meet his eyes, and tried her best to smile like a Waldorf should. She hated feeling so weak.

Chuck caught on because, in all honesty, he was the same way when it came to having fears. He'd sooner hide them than let them show. "Hey…we don't have to do this if you don't want to, Blair." She was about to argue, and he could see it, so he went on. "But, I want you to know that if we do this…I'm going to try real hard to make this whole thing as….fun as possible."

Blair's smile got a little wider and she nodded her head. "I know. I'm just…nervous about the….well, you know…the pain. I'm not so good with that, but if you're willing to be…gentle, then I'm willing to try. I'm probably not going to be as fun as the rest of the girls you've…been with." She looked away shyly.

"Don't even think about that. You're one of my best friends. Obviously you mean more to me than any of them…and for what it's worth, I do promise to be gentle," he said with a smirk. He put his hand behind her head, and kissed her softly. He lifted her thighs up so that she'd wrap her legs around him, and when she did, he lifted her up off of the seat, and then laid her down on the larger floor of the limo.

"Why are we down here?" Blair asked.

"More room," he breathed into her hair, and then chuckled. "Don't worry, Waldorf. I'm going to take care of you." He tucked a few of their clothes underneath her head so that she wouldn't have to lay it on the hard floorboard, and then he reached into the limo mini bar, and pulled out a towel. He unfolded it. "Lift your butt up real quick." When she complied, it laid the towel under her lower half.

"What's that for?" She asked confused.

"Sex is kind of messy, Blair. Especially the first time…blood, you know?" He looked at her meaningfully, and realized when she stiffened that she had never even thought of that. "Hey, hey…don't worry." He settled himself down on his side next to her, and began kissing her again. "Let's just do other stuff for a little while. Helps with the nerves."

She nodded, and then threaded her fingers through his hair before kissing him back.

Chuck's hand trailed back down her body, but didn't stop at her breasts this time. Instead, he just brushed over her nipples gently to elicit a moan before moving them down further. He lifted his hand, by passing the place she needed him most, and ran his fingers across her inner thighs. She began writhing around a bit, and moaning out his name rather loudly. He felt her fingers grip his hair a bit tighter as he broke away from her lips. He brushed his lips in the same path that his hand had gone, stopping at her nipples just long enough to flick his tongue across them to drive her crazy, and then moving down to her stomach, before kissing her hips. As he trailed a little lower, she stiffened, and tried to pull his head up by his hair.

"What are you doing, Chuck?"

"Relax, Blair," he traced the hand that wasn't on her thighs across her stomach. "I'm not going to hurt you. In fact, when I'm done here, you're going to be begging me for more."

She looked at him skeptically for a second, and then slowly laid back down and tried to relax like he had said.

He lowered himself between her legs, and lifted both of them to drape over his shoulders. He blew a little bit of air across her glistening center, and she bucked her hips up slightly. He liked this reaction, so he did it again, and again until she was bucking up wildly enough for him to have to settle both hands on her pelvis to still her. He flicked his tongue out finally, and dragged it from her folds up to her clit. She yelped, and tried to buck up again. Chuck brought his hands down just a bit to spread her folds, and then he went to town; sucking, flicking, prodding with his mouth. It didn't take long to have her almost screaming his name. He knew that she was close, so he brought his mouth to her clit, and sucked as hard as he could while he pushed one finger inside of her wet core.

"Ch-Ch-Chuck…" she moaned, and tightened her fingers in his hair. She could feel the tension in her lower abdomen building up greatly, and she began to quiver.

He entered a second finger into her heat, and flicked his tongue across her clit as fast as he could. He could feel her whole body trembling a bit, and then her muscles started to contract, so he moved his fingers in a "come hither" motion. 1…2…3…4 times, and she cried out his name. He continued his ministrations until she stilled beneath him, and then he lifted his head.

"How was that?" He asked with a smirk when he could see her spent below him.

"Mmm…I liked that, Chuck." She said honestly before pulling his head up towards her mouth. She could taste herself on his lips, and for a moment she thought that that should turn her off, but it didn't. "Chuck…I need you. Please."

He chuckled, and gave her a big smile. "No need to beg, Waldorf," and then he was up and reaching into his discarded pants pocket for a condom. He quickly found it, and brought it up to his mouth to rip the wrapper open with his teeth.

Blair watched him expertly roll the condom down his shaft, and when he looked up at her, her nerves started to jumble around again. When he settled back down between her legs, she tensed up again.

Chuck softly brushed a strand of hair off of her forehead. "It's okay. Just relax…try to take deep breathes."

She smiled, and thought for a second that he was really sweet because he was breathing with her to show her how, as if she hadn't been doing it her whole life. She felt his erection press a little bit at her entrance, and he paused for her reassurance. She nodded, and then tried to hold his gaze, but as he entered her, and slowly but surely broke through her barrier, she sucked in a sharp breath, and squeezed her eyes shut. He said to breathe right? Crap…I forgot, she thought, and then she felt him pause. She opened her eyes, and he was staring down at her concerned.

"You okay?" He was breathing hard. She was so tight, and felt so good to him, but he knew that she must be hurting. He wasn't even halfway in, and he was almost afraid to go any further.

"It hurts," she wimpered. "Are you sure we're doing this right because no one really ever told me much about….this part." She could feel a little bit of blood run down her thigh. Great! This is so embarrassing!

He chuckled a little bit. "Yeah, we're doing this right. You're just really tight. Do you want to stop?"

She shook her head quickly. "No…nah, it's okay. Keep going. Just…go slow."

He knew that she was trying to act brave, and was almost tempted to pull out, but he didn't want to tick her off, so he inched in a little bit further. She still wasn't all that relaxed, which he could understand, so he kissed her forehead over and over again softly, and whispered any comforting words he could think of. "It's okay, B. Relax. I promise I'll make you feel so much better. Just relax," and soon he was in to the hilt. He gave her a few minutes to adjust to him, and when she opened her eyes after a while, he didn't see all that much pain left in them. He smiled a little bit.

"You can start moving. It doesn't hurt that much anymore."

He nodded his head. "Okay. We'll just got slow for now." He pulled back slightly, and then moved back in to test the waters, and she moaned a little bit before reaching up to grip his shoulders. He tried it again, and she moaned a little louder. He felt a little better knowing that she didn't sound like she was starting to get pleasure out of it. He then pulled back until just the head of his cock was still inside of her, and then pushed forward a little bit faster than before, and the look on her face was one of pure bliss.

"Ooooh Chuck…" she purred. "Okay…you can go a little faster, now." She closed her eyes, and smiled a little bit.

He chuckled. "You got it, Waldorf," and then he did the same move as before a little faster, just because he loved the look on her face. He groaned, and then buried his face in her neck and thrusted faster.

"Oh, Chuck. That feels so good." Blair started bucking her hips up to meet his. She once again felt that familiar feeling coiling in her lower abdomen, and she wanted so bad to relieve it. "Oooh…harder, Chuck…faster, please."

Chuck didn't need to be told twice to oblige. He knew that she was close. He could feel her inner walls gripping him like a vice, and he wanted so bad to just come right there, but he couldn't let himself do that until her needs had been fulfilled first. He felt her hands gripping at him for control of what was happening to her, and he grabbed one of her hands in his, entwined their fingers, and just lost almost all of his own control. He was pounding into her now, his head buried deep into her neck, and she was purring in his ear.

"Fuck, Blair…you're so fucking sexy," he felt her clench around him at the words, and then she screamed out his name.

"Chuck, Chuck, Chuck…" she chanted into his ear as he helped her ride out her orgasm.

Her clenching muscles pushed his own release over the edge, and he came right then and there. "Ooh, Blair, baby, I'm c—" and then was cut off by her lips crashing up onto his. Her fingers squeezed his tighter, and she helped him to ride out his own orgasm. He collapsed almost onto her a second later.

It took them two or three minutes to catch their breath, and when he did, he slowly pulled out, eliciting a whimper from Blair because of the loss. He pulled off the condom, and disposed of it in the trash in a compartment by the mini-bar, and then he helped her up off of the floor.

They quickly scurried around picking up their clothes, and got dressed in silence. After a few minutes, Blair spoke.

"I should probably get home. Dorota always rats me out for coming in 'too late,'" she said with a giggle.

Chuck nodded his head, and then told the driver where to go. When he sat back in the seat, he looked over at her to see her wide-eyed, and staring straight ahead. He reached over and took her hand into his. "I had a great time with you tonight, Blair. I hope you enjoyed yourself also."

She met his gaze, and smiled slightly. "Yeah…yeah, I had a good time." She nodded.

"Listen…I really want to apologize. I know that this isn't exactly the way that you wanted to do it for the first time…"

"Shh. No, Chuck, really. I had a good time. It's just…a lot has happened tonight, you know? I'm just afraid of saying something to complicate it."

Chuck nodded. "I understand that completely. You probably have a lot on your mind at the moment."

They pulled up outside of her home at that moment. "Yeah, but…thank you, Chuck. I really did enjoy myself like you promised."

He smirked. "Told you so, Waldorf."

Blair giggled, and leaned over to kiss his cheek. "I'll see you at school tomorrow," and with that, she was out of the limo, and walking up to the building, and through the front doors.

…and then the butterflies started.