A/N: When inspiration comes calling, you must answer its call. In my opinion, every diehard CB fan needs to write at least a few different versions of B losing her virginity to Chuck in the back of his limo. It's where it all began and it demands to be depicted in a variety of different ways by endless fantabulous writers. ;) Here's a version of B losing her virginity with maybe a more realistic, vulnerable approach. Hope you enjoy. =)

*I own nothing. No copyright infringement intended.

It had been the heat of the moment. It had been the way he had looked at her. It had been the smooth vibrations as the wheels of the limo moved over the road beneath them. There, in that moment, everything in her yearned to throw herself at Chuck Bass and let him have his way with her.

That was some time ago though. Ever since she had plunged headfirst into the deep end, her mind had gone blank and all she could feel was his hands on her, his lips, his tongue, the way he pressed himself against her or pulled them from one side of the seat to the other. The moaning, the brief moments where they had to catch their breath and so alter movements to taking each other's clothes off, those moments were all that she had of not being totally and completely consumed in him.

But now, twenty heated minutes later, after all barriers had been stripped away, one needed to be put in place, and it was there, in that moment, that Blair Waldorf had a coherent thought and almost voiced it aloud.

She was going to lose her virginity to Chuck Bass in the back of his limo in less than an hour after she'd broken up with her boyfriend of what had to be at least five years. She couldn't gather the exact amount at the moment, which was shameful if she actually had the brain power to focus and think about it.

She didn't.

It wouldn't be till the next morning when all of that would truly set in and propriety, social standards, and other people's feelings would come into play. Even the name Chuck Bass and the word limo didn't appall her here where no one else could see her, where it was just them alone together living in a world she would have never called her dream world and yet had somehow become absolutely perfect and just what she needed.

No. The only words in that particular thought that had suddenly out of the blue begun to gnaw at her were: lose her virginity.

She'd thought about it once. Okay, several times. She'd romanticized it of course. There would be candlelight, flower petals maybe, possibly quiet romantic music further enhancing the atmosphere. It would be in a bedroom, and as far as she could remember, the plan had been that it would be with Nate.

Only briefly had she thought about potential pain or awkwardness. Now the thought wouldn't leave her alone.

Would it hurt? For how long? Would Chuck notice? Would he mock or tease her in the future? Would he think back on this occasion as the worst lay he ever had? Would she be so clumsy he would stop halfway through? Would he push further regardless of any pain she might have or maybe because of it? He wasn't exactly known for letting the lady decide. She didn't know if he'd done it or not, but she didn't think it was beyond him to enact date rape.

"Blair?" Chuck said, and the sound alone brought her back to reality. He had turned away to grab the condom stuffed in his pocket and slide it on. She hadn't gotten a good view of it before he turned away, but she certainly had one now.

When he'd first pulled away excitement had thrummed through her, knowing the moment was almost upon her, but now that thrilling feeling had dimmed considerably and fear was creeping up on her at the speed of a jackrabbit. A cold sweat was developing on her forehead and all she could think about was the incident in The Palace kitchen Serena had told her about. She had been enraged of course, but she hadn't been overly surprised. And it wasn't like harping on Chuck was going to change anything. It was a part of who he was and he wasn't about to change, and she was fine with that. Aside from herself, Serena was the one girl Chuck had never been able to get his hands on. She imagined it was particularly infuriating because she'd slept with just about as many guys as he had girls.

Now, with herself in the same position, except willingly, she felt the same fear she saw on Serena's face that she'd tried to hide when she confided the secret.

Blair cleared her throat, bringing her back to the present when she realized she'd been quiet far too long. She'd been staring at his erection ever since he turned back to her but the smirk she'd felt from him at first had faded and she could've sworn she felt concern drumming into her forehead from where he was staring at her face.

"Do you not…"

Her eyes flashed up to his. "No, of course not!" she said quickly, forcing herself not to acknowledge all of a sudden that there was not a single piece of clothing on either one of them. She felt very self-conscious.

But she couldn't tell him to stop now. That would be absolutely humiliating if she asked him to stop after she'd gotten him all riled up. She hadn't touched him there yet, but she imagined he was hard and warm.

At least that was what she had heard.

"Let's do this," she insisted, sliding over to him and kissing him fiercely, careful to keep her legs angled away from his and so avoid touching that particular part of his anatomy.

Not so surprisingly he didn't respond to her kiss. Instead, he pulled away.

"I asked you if you were sure…" he said cautiously.

"And I am. Kiss me, Chuck Bass." She leaned forward, but he pulled back before her lips even brushed his. She frowned. "What is it?"

"It's okay if you don't want to do this, Blair."

And just like that he had lit the fuse and she was angry. He had no right to treat her like a weak little girl when she was the one that had launched herself at him.

"What the hell is your problem? I'm here, aren't I?" she demanded. He hesitated. "Don't tell me you're concerned about how this will affect our friendship," she spat.

"What? No," he insisted.

"Well then what?"

He grabbed her arm and lifted it up so that she could see her hand hovering at eye-level.

"This, Blair."

She gulped when she finally realized her inward thoughts and feelings had now become visualized.

"You're trembling," he said softly. "You're scared."

"I am not," she defended, but her voice cracked and faded at the end so that she wondered if she'd stopped breathing momentarily. She gulped, hoping it wasn't too loud. It sounded awfully loud in her own ears, like the way a loud ringtone sounds in a silent room full of people where all is supposed to quiet.

He sighed and leaned forward, pressing his forehead against hers in the most tender gesture she'd ever seen him make, and with her. She was sure this was not the way he went about it with all the other virgins he bedded.

"It's okay," he whispered. "You can change your mind."

She shivered when he reached up to tuck wild hairs behind her ear, doing nothing to improve her overall messy do.

She shook her head. "I don't want to. I want this. I want you." And even in the back of her mind she knew she'd regret those words in the morning.

But right now it didn't matter. Right now she was just scared of whatever pain she might feel, and his reaction to her reaction of it.

"I won't hurt you," he promised.

She nodded, even though she wanted to laugh, because he'd never been this tender and even if he thought he was being gentle she was very likely able to still feel some semblance of pain.

She gulped again and then let him kiss her gently.

"Trust me," he whispered.

She shivered and her voice wavered, but again she nodded and responded, "Okay."

He kissed her again, threading his fingers through her hair. He did this for awhile and gently let his lips press little kisses down her neck and across her collarbone to her shoulders, sweeping past her arms between her breasts and down onto her stomach. Her breath hitched when he reached the nest of curls at her core, but feeling the tension in her, he bypassed whatever need he might have felt to kiss her there and moved down to her thighs, massaging her breasts as he laid her gently flat on her back on the seat and reached down to her gracefully curved ankles before returning back to her lips.

Feeling more relaxed, she threaded her fingers through his hair when his lips returned to hers and nodded before he could even say it.

"Okay," she said, her lips even twitching a bit at the corner. "I trust you."

And with that he kissed her again, this time more passionately, and with that distraction, he used his body to push her legs far apart and slowly but steadily pushed himself into her, using every ounce of willpower he still possessed to not thrust too fast or too eagerly. For the life of him he couldn't understand why he'd taken such pains to make sure she felt comfortable and safe and that the experience was good for her. He certainly hadn't cared that much for any other woman he'd slept with, especially not the virgins, which he often avoided just for the sake of experience made the sex more enjoyable, and memorable, even if he could never really remember names or faces not five minutes after the women left his bed – or wherever they had been.

But this was Blair. She was different, and he couldn't explain why. He just felt for some inexplicable reason that next to Nate, and of course his father, she was the only person he felt the need to really care about. He'd teased about taking her before, if for nothing else just to get a rise out of her, see her crinkle her nose at him or scoff in disgust. But actually doing it, actually committing the act was something else entirely. It was serious, and not something he wanted her to forget, most especially not because of the pain.

"You okay?" he asked suddenly when he heard her breath hitch again and felt her nails dig a little into his shoulders.

She gulped but nodded, closing her eyes. The heart he didn't know he had somehow completely broke when he saw tears fall out of her closed lids and rest on her cheeks, sliding down the sides of her face. He wished there was some way he could make the pain stop.

"Do you want me to stop?" he asked, but her eyes flashed open and she shook her head fiercely, unable to voice the words.

Honestly, she was scared it might hurt even more no matter which direction he moved in.

They both swallowed hard and incredibly slowly he pushed through even more until he heard the sudden cry she made and he pushed forward all the way. Then he waited with bated breath, breathing harder than he was sure he ever had in this type of situation, and honestly not knowing what he should do next.

When he felt her relax only a few minutes later, he was stunned, even if he shouldn't have been. No matter how bad the pain, it usually passed relatively quickly. He'd forgotten.

"Okay," she said, wrapping her arms tightly around his neck. "Continue." She let out a deep breath of relief. "Please," she said softly, because the feeling of his long member inside of her, touching every inch of her core had revived in her the horniness that had enthralled her before all of this had gotten so tense.

He was hesitant, but gradually the slow speed he went at drove her mad and she begged him to go faster. So he pushed forward and suddenly he was lost in it all, pounding harder and faster than he had ever dared go with any virgin, worried for his own contentment naturally – in those situations.

He was careful to make sure she came first and tried not to think about how that was a first as well.

When he'd followed her shortly after, he collapsed on top of her, his propped arms giving out. Her arms came around him and held him loosely. Her head tucked into the crook of his neck and he could've sworn she was nuzzling him. He felt totally and completely content.

It was a shock to his system when not an hour later he was awoken to find her slipping out of the car with even her dress back on and flitting to her building. No good-bye. No snide remark. No shy smile.

No thank-you.

Somehow that one in particular bothered him.

But before he could ponder it further, the car was moving again and he knew any running after her tonight would be pointless. What would also be pointless he was slowly realizing was forgetting this night, or refusing to pursue her the next day.

Because in all honesty, he'd never felt this way before, and Chuck Bass always gets what he wants.

A/N: Yeah, maybe this was too tender, and maybe the actual losing of B's virginity was totally rough and tumble like maybe could be implied from the show. But what is also implied, I think, in vague references in season 1 was that Blair losing her virginity was not a bad experience for her and so the potential is there that the reason for that was because Chuck was gentler with her when it came down to the actual act. *shrug* I just got inspired to paint the picture if B got really scared beforehand. I know I would be. ;) Read & Review if you wish. =)