A/N: Okay, so basically the premise of this story is that Blair experiences her first time with everything other than making out with Chuck. This doesn't include the first time they have sex, because we all know how that one turns out. But all other kinds of sexual foreplay are included, so enjoy. As for my other story, Finding a Way Back, I promise I'll add to it again eventually... it's been a busy month, but I should have more time to update once I'm home from school next week. This story just sort of occurred to me out of nowhere, so I decided to go for it. I hope you like it... please read and review!

First Time

Blair glanced over at the clock sitting on her bedside table. 11:30. Perfect. That meant her mother had already been asleep for half an hour, and that Dorota was just turning in for the night. She would not be disturbed until Dorota woke her for school at 7:30 the next morning.

Blair was lying on her bed, propped up against her pillows and not yet under her covers because it was a warm night. She was wearing her favorite pale green slip, the one that always made her feel sexy. Or at least sexier than she ever felt when she was around Nate. She loved Nate - well, she was pretty sure she did, anyway - and she knew he was her golden prince, her happily ever after. But at the same time, she couldn't help but notice that when he looked at her, their was never any desire in his eyes. In fact, it always seemed like he was more enthralled by Serena than by Blair - as if Blair didn't already have enough of an inferiority complex as Serena's best friend. All she wanted was for a man to look at her with lust in his eyes, to throw her against the wall and whisper dirty words in her ear and ravish her. The problem was, she knew Nate would never do that. The even bigger problem was that she wasn't sure she even wanted Nate to be the one who did that to her.

Blair wanted to be touched. Really touched. But not by Nate. For some mysterious reason that probably involved the universe conspiring against her, Blair could tell that even if she and Nate ever did more than make out (which, up to this point, they hadn't), Nate would not be able to touch her the way she wanted to be touched. And so she had resorted, without much success, to doing it herself.

It was not something she was proud of. It was her darkest, dirtiest secret, and she felt embarrassed every time she slid two fingers inside herself and tried to make herself feel the kind of pleasure Serena had always described. But at the same time, she desperately wanted that incredible feeling, whatever it was, and she refused to stop trying until she felt it. And so at 11:30 each night, she allowed her hand to trail down her stomach, slide into her panties, and begin rubbing circles around her clit. It felt good, and a few times she swore she had nearly orgasmed. But, much to her frustration, it had never actually happened.

Tonight was no different. As her fingers worked her core, she could feel the tension building in her body, but she could already tell it wasn't going to work. With an angry sigh, she kept pushing her fingers in and out, around and around, feeling almost desperate. And then she heard a familiar voice, and her heart nearly stopped.

"Well, well. I think I may have just died and gone to heaven," Chuck drawled, the signature smirk on his face mixed in with an expression of awe, and, unless Blair was very much mistaken, lust.

Blair flushed crimson red and hurriedly pulled her fingers out of her panties. "Chuck! What the hell are you doing here?! Get out!" she hissed, not wanting to wake the rest of the house.

Chuck merely smirked and strode across the room so that he was standing beside her bed. "I was stopping by to share with you the latest dirt my PI uncovered regarding Penelope's... ah, extracurricular activities with her flute instructor. Let's just say that she is most definitely playing his instrument. But enough about that... it seems that God had much greater plans for me tonight." He reached forward to stroke her cheek, but Blair slapped his hand away.

"Haven't you ever heard of knocking? And since when do you believe in God?" Blair said angrily, pulling a pillow across her chest to serve as a barrier between her and Chuck.

"Since I walked into your room and discovered Blair Waldorf, the virgin queen, all hot and bothered and trying to get herself off." He sat down on the bed and leaned towards her. "What's the matter, princess? Nathaniel not satifsying your needs? I always knew you were too much for him." It was true. Chuck had stifled his attraction to Blair for years out of respect for both her and his best friend, but he had always known that Blair deserved so much better than Nate. She was, after all, the most exquisite thing Chuck had ever seen, but stupid Nathaniel was always too busy gazing longingly at Serena to notice what was right in front of him. It infuriated Chuck to no end, but he had kept that to himself because he thought Blair was happy. Now it seemed that she had finally realized there was something missing in her perfect relationship with Nate. And the fact that she had resorted to touching herself - well, that was essentially Chuck's greatest fantasy come to life. He had nearly come in his pants just watching her.

Blair didn't know whether she should feel more scandalized or mortified. Both seemed like appropriate reactions to having Chuck Bass walk in on her masturbating, but in an effort to preserve her dignity, she opted for scandalized. "You're disgusting. Of course Nate is satisfying my - needs. Not that it's any of your business."

"I'm Chuck Bass. Everything is my business," Chuck said. "Besides, you forget who you're talking to. Nathaniel is my best friend. He has no idea how to touch a girl. And even if he did, I know he's not touching you. If he were, you wouldn't lying in bed alone finger-fucking yourself at 11:30 on a Wednesday night. Not that I'm complaining."

Blair opened her mouth to retort, but she couldn't think of anything. Finally, she settled for a threat. "If you ever speak a word of this to anyone, including Nate, I will personally see to it that every female in Manhattan hears that you have been mysteriously afflicted with a highly contagious and untreatable case of genital herpes."

Chuck sneered. "Be my guest. I could use a bit of a challenge. And it's not as if I'm opposed to calling in foreign company."

"You're heinous," Blair snapped. "So then what? Are you going to tell the whole school about this?"

"Please," he scoffed. "What would be the point in that? I'd rather keep this mental image for my own personal enjoyment."

"Pervert."

Chuck smirked again. "I do have a proposal for you, however."

Blair raised her eyebrows. "And what's that?"

"Let me show you what it feels like to be fingered well." Chuck watched her face closely as he spoke, wondering if this was pushing her too far. He of course knew she would reject him instantly, but it was worth a shot. Especially considering the uncomfortable state of his groin right now, touching Blair Waldorf was something he wanted very badly.

"No," Blair said automatically, even as the idea of Chuck fingering her sent a thrill through her whole body. It was disgusting. DISGUSTING, Blair. But at the same time, it was intriguing. And so deliciously forbidden. She wanted it - wanted him. She loved the way he was looking at her right now, his eyes dark with lust. Their bodies were so close... if he just moved a little bit closer, they'd be touching. He'd be touching her. Really touching her.

"Fine," Chuck said, trying to hide his disappointment. "I'll see you tomorrow, Waldorf. Thanks for the show."

Just as he rose to leave, Blair caught his hand. His heart leapt. "Chuck. Wait. I-" His eyes flashed back to hers, and he understood. She was too afraid to ask for what she really wanted, so she was silently begging him to give it to her anyway. She tugged on his hand a little, and he leaned in, his lips hovering inches from hers, completely unable to breathe. And then he kissed her, and it felt as if something had exploded inside both of them.

He was on top of her in seconds, pressing her down on the bed and sliding his tongue into her mouth as she kissed him back eagerly. She had never been kissed like this before - with so much passion and urgency. It was as if Chuck couldn't get enough of her. His hand ran up her creamy thigh and under her slip, coming to a halt on her butt. He pulled her into him, and her leg hooked around his back. His other hand found its way to her breast, kneading it through the fabric of her slip. He allowed his mouth to drift down her body, leaving kisses on her jaw and collarbone before pulling down the strap of her slip and pressing his lips to her breast. Blair let out a slight gasp and knotted her fingers in his hair as his tongue glided over her nipple. She couldn't believe that she was actually doing this right now - with Chuck Bass, of all people - but it felt so good and so right that she never wanted to stop.

But then she felt his hardness pressing against her, and she flinched, suddenly scared. Chuck pulled away and their eyes met. She was surprised to see concern in his expression. "What's wrong?" he asked.

"It's just - I - nothing," she stammered, embarrassed.

"Blair," he pressed.

"Never mind. I'm fine."

"Blair." His eyes bored into hers, demanding that she tell the truth.

"I - I'm scared," she admitted, looking away from him.

"Of me?"

"Kind of," she said, blushing. "And just all of this."

"I'm not going to hurt you," he said softly.

"I know."

"And you can stop me whenever you want. I won't get mad."

Blair nodded, still not meeting his gaze.

"Hey. Look at me," he said, lifting up her chin so that their eyes met again. Blair was again surprised by how genuinely concerned he looked. "Are you okay?"

"Yeah. Yes."

"It's going to feel amazing, Blair. Trust me." Trust me. Hearing him say those words was oddly comforting. Blair hated (or pretended to hate) a lot of things about Chuck - like how he was disgusting, cocky, and morally bankrupt, to name a few - but in spite of all that, she had always trusted him.

"Okay," she said, her voice more confident. "Keep going."

Chuck grinned. "You sure?"

"Yes," she said, smiling back.

Chuck kissed her again, this time more softly. He wanted to make her feel comfortable by taking it slow. He also wanted to savor every single moment of what was happening to him right now, because only in his wildest dreams had he ever hoped he would really be touching Blair Waldorf.

Blair tentatively would her arms around her neck and pulled him in closer, deepening the kiss as her tongue delved into his mouth. Chuck slid a hand between her legs, massaging the soft skin of her inner thighs as he inched towards her center. When he finally reached her panties, he was both surprised and pleased to find that they were already damp. He hooked a finger through the strap and pulled them down, then returned his hand to its position between her legs. He heard Blair's breath catch in her throat as he slowly traced a finger across her slit. Chuck couldn't believed how hot and wet she was already, and the fact that it was all because of him turned him on even more.

"You're so wet," he murmured against her lips, his fingers hovering infuriatingly close to her aching center.

"Mm," she replied. "Touch me, Chuck."

The hint of desperation and the breathiness in her voice was all the incentive Chuck needed. Looking her straight in the eye, he gently slid two fingers into her and began slowly pumping them inside of her. Blair let out a cry, lifting her hips up against his hand. She couldn't believe how good this felt. And then he began to pick up the pace, and he brought his thumb up to circle her clit. Blair fisted her hands in her sheets and began to moan in earnest, arching off the bed, desperate to feel him deeper inside her. Chuck watched her face in fascination, absolutely transfixed by this new side of Blair that he had always known existed but had never actually seen.

Blair felt her body begin to clench, and then, before she knew it, she was shaking and screaming Chuck's name as she rode out her first orgasm against his hand. When it was over, she looked up at him, panting, a slightly dazed expression on her face. "Wow," was all she could manage to say. It had been even better than she expected, and although she would never admit it to him, she suspected that had something to do with the fact that it had been Chuck fingering her.

Chuck smirked, feeling very satisfied with himself and more than a little turned on. "Told you."