A/N: Okay, sorry it took me so long to update this story! I'll try to get the next chapter up sooner. Just to clarify, this is set some time at the beginning of season 1, before Chuck and Blair have sex. The idea is that Blair is still with Nate, but she's beginning to doubt their relationship, especially because of what happened with Serena. Basically I just wanted to write about what it would be like if Blair experienced all of her sexual firsts with Chuck. So that's what this is. There will probably be 2 more chapters after this one... Oh and also, let me just say that the Chuck and Blair scenes in the finale (especially the last one) absolutely made my life. I'm so happy he finally said it!!!! I LOVE THEM. The only thing that was missing was some very steamy Chair sex scenes, but hopefully we'll get more of that next season. And speaking of next season, I don't know how I'm going to last all summer without new episodes! I suppose I'll just have to immerse myself in writing Fanfiction :). Okay, now I'm done ranting. Please read and review!

First Time Chapter 2

As Blair lay panting in something of a post-orgasm daze, Chuck rolled on to his back beside her and debated what to do about the increasingly pressing need in his groin. Fingering Blair and watching her orgasm because of him had made him hornier than he had ever been in his entire life, and he needed some release as soon as possible. Of course, ramming his dick into Blair would have been the best solution to his problem, but seeing as that wasn't going to happen any time soon, he needed an alternative. Normally, he would have gotten whatever slut he was with to blow him, but Blair was different - she was his friend, and he respected her. He didn't want to ask her to do anything that made her uncomfortable. He supposed that if he had to, he could go jerk off in her bathroom or something, although he wasn't entirely sure that would work.

"Chuck?" Blair said after a few minutes of silence.

"Mm?" Chuck replied, shifting slightly in an effort to relieve some of the discomfort in his groin.

"Thank you," she said quietly.

Chuck let out a small laugh. "Any time, Waldorf. I'm happy to help whenever your needs need satisfying."

They lay in silence for another minute or so, Chuck growing more and more uncomfortable.

"Chuck?" Blair said again. She had suddenly been struck by an idea that was simultaneously terrifying and thrilling.

"Yes?"

"What about your needs? Could I maybe give you a hand?" Blair smirked to herself, pleased with her little play on words.

Chuck looked over at her, eyes wide. "Are you serious?"

Blair propped herself up on her elbow and nodded. Her heart was beating very fast, but she was pretty positive she wanted to do this. She wanted to give Chuck the same kind of pleasure he had just given her. "Completely."

Chuck watched in awe as she reached over and pulled his shirt out his pants, then began working on his belt. She had it off quickly, and before he knew it, she had pulled down his pants and boxers, exposing him. He was pleased to see her eyes widen and her lips part slightly when she saw how big he was. "Umm," she said, her voice trembling slightly. "How -"

"Wrap your hand around me, Blair, and just move up and down," Chuck instructed. She did as she was told, tentatively wrapping her fist around the base of his penis. His breath caught in his throat at the feel of her hand on him. She slowly began moving up and down, taking it as a good sign that Chuck's breathing was getting heavier and heavier. Emboldened by the way he was responding to her, Blair decided to play with him a bit. She traced a finger over his balls, then ran it up the underside of his penis. Chuck gasped as she began to massage the head with her palm.

"Fuck - Blair - up and down, like I told you," he grunted, his hips arching towards her. Blair merely smirked wickedly and began devising a scheme to torture him. After leaving a few kisses on Chuck's neck, she temporarily abandoned his throbbing dick and redirected her attention to completing removing his pants, which had thus far been around his knees. She tugged them all the way off and tossed them to the floor, then climbed on top of Chuck, straddling his right leg. She ground her bare, still wet pussy against his thigh, causing his eyes to roll back in his head.

"Jesus Blair, stop messing around and put your fucking hands on me!" he moaned. His cock was painfully hard by now. How was Blair, the untouched virgin, so damn good at torturing him? It was like the girl had been specifically designed to drive him absolutely out of his mind.

"Only if you ask nicely," Blair purred, making him flinch as she allowed her fingertips to graze over his tip.

"Please," he groaned, and he felt her small, warm hand close around the base of his penis once more. "FUCK, please!" She started working her hand up and down again, varying the pressure she applied and gradually picking up the pace. Chuck could feel himself getting closer and closer, he was nearly there... "Shit - Blair - move - I'm about to come -" he choked out.

"It's okay, I don't care," she replied, and seconds later, he exploded on to her stomach. The normal Blair would have been completely grossed out, but the post-being-fingered-by-Chuck-Bass Blair was so thrilled to have successfully jerked him off, and so turned on by the fact that she had literally had him - Chuck fucking Bass - begging her to touch him, that she really didn't care that much.

"Sorry," Chuck said, grabbing some tissues from her bedside table and using them to clean her up. Blair was pleased to feel that he was still trembling in the wake of his orgasm.

"It's fine," she replied honestly. "So, how'd I do?" she asked with a smirk as Chuck tossed the tissues into the trash.

Chuck looked at her, still unable to believe that Blair Waldorf had just given him the best orgasm he had ever had in his life - and they hadn't even had sex. She looked so beautiful right now, her eyes bright, her cheeks flushed, her hair a bit messy, and her body still gloriously naked. She was more free and uninhibited than he had ever seen her before. Why she had chosen him of all people to show this side of herself to, he had no idea, but he wasn't about to complain about it. He only hoped that this would be more than a one time occurrence. "You were incredible," he said, and Chuck didn't think he had ever answered a question more sincerely in his entire life.