Chuck and Blair had always been friends. They were in each other's circles even before kindergarten. When Blair was little, she believed Chuck was an evil child. Always making jokes about the other girls in the class and trying to give them a peck on the lips. Right into middle school, Blair was sure that he got even more wicked than before, flaunting his scarf at girls who seemed to be attracted to him unlike Blair, and kissing half of the bratty children of their class. Around the time they were in high school, she realized that Chuck had changed. Not only he had his way with the girls of the first year but with the seniors as well.
For some weird reason, it annoyed her. She was both disgusted and envious that he went so easily into the sex field – unlike her. She had only eyes for Nate but not the guts to give herself to him, and after all that he had done, she didn't want to please him and give away what she couldn't. She had asked herself several times why. Was she insecure? Totally. Was she scared? That is for sure. But aren't most of the people like this?
As she slowly opened her eyes in Chuck's limo, all that had just happened dawned on her. They had slept together. In a moving car. Her eyes snapped open when she realized her surroundings: black leather seats that could be probably over 5'7 long faced each other and over those, a line of tinted windows divided the side of the car from the top. She was sitting in the furthest seat across from the driver and luckily there was a wall that separated the two chambers of the limo.
She sighed and placed a hand on her forehead, then flipped the lights on. "Oh my God", she tried to calm herself down. When she looked around, her head spin a little. She looked at her left because the silence was too deep, and realized that she was alone. Where did Chuck go? She thought about what if he left her alone and a part of her loathed the possibility.
A wave of relief washed over her, though. She could leave the limo and run away to her house before he returned, which wasn't a nice thing to do but she did not care. She had already given her chastity to him, she was super ashamed already. She closed her eyes and bit her lip. "You're crazy, Blair!" she told herself as she checked the state she was in. Now it was a shriek that escaped her lips, and it wasn't one of pleasure, one of those screams she remembered she did while Chuck was with his head between her thighs and he was...
She shook her head to forget what she had just replayed. Looking down, she saw that she was still in her nude chemise and that a dark suit jacked covered her lap and a little of her legs. Her bag was in the proximity of the lateral seats along with her headband and on the opposite side, she caught her matching panties and bra scattered like trash. Her dress was folded on a seat.
Her hand covered her mouth and she narrowed her eyes when she saw the mess in front of her. She decided to take her things and get out as fast as she could so that she could get back home, get in her bed, sleep and hopefully forget all of this. It must have been a dream.
She put his jacket on the seat beside her and she crouched down and helped herself reach her bra and her panties when she heard a whistle. "I thought you were great in the front, but you are even hotter from the back."
Blair jolted and quickly turned to face a lips-licking Chuck with a raised eyebrow. He looked aroused and wild, like a lion eyeing his prey. She realized what he might have seen and she felt her cheeks get hotter. "You're disgusting, Chuck. You know that?"
"Of course I know" he said, his eyes roaming up and down Blair's body. "But I am not prude to admit it. You, on the other hand, should embrace your feisty side."
Blair rolled her eyes. If there was a person who should lecture her, it wasn't going to be Chuck. She grabbed her things and sat down on the seat opposed to his. "You haven't seen anything tonight. Am I clear?"
He glanced at her legs, then at her face, and smirked. She wasn't sure why, but she found that sexy. Had Chuck always smiled like that? "I haven't seen anything, huh? I have seen enough, Waldorf." He stated, nodding his head slightly and focusing on her lap.
She was exasperated. What had she got herself into? She put both hands that were full with her clothes on her lap as to cover herself. "You are a slimy bastard."
He tilted his head to the side and grinned widely. "Yes, I am. But you knew that already, didn't you? Yet, you fell into my arms and lost your virginity to me."
Blair massagged her temples. She lost the count of how many times she did it today. Once because of Jenny and the masked ball truth, then because of Nate and his closed mouth when she asked if he loved her, and now with Chuck. She wasn't sure which one of these frustrated her more. Perhaps Chuck's brutality and lack of diplomacy about what had just happened.
"Well, I want that back!" She cried out, opening her arms and shaking her head.
He looked amused as he leaned in towards her. "Too late, Blair. You can't give yourself to me and ask me to erase the tape. Which, by the way, I have really enjoyed."
She slapped his arm. "Forget that it ever happened or –" she blurted out with a hateful tone before she was interrupted by Chuck's face getting even closer than before.
He raised both eyebrows questioningly. "Or? What will you do, Blair? Pretend that it never happened and get back with Nate? Spread dirty news about me at St. Jude? I'm sorry for you, but Gossip Girl does that already and I have nothing to hide."
She sighed. She didn't like to admit that he was right, but it stung to believe that she had just lost her V-card to such a manwhore like Chuck. They had known each other for years, but this didn't mean he would give her special treatment; he would just add her to his long list of girls he had fucked and that was it. She would just be another trophy for him. She shook that thought out of her head. Did she just imply that she wanted Chuck to remember their intimate encounter?
She gazed at her folded dress on the left. She wondered if Chuck had put it there then told herself not to hope too much although who could have done it? Arthur? Shit. She bit her lip. "Did you fold my dress?" she asked out of curiosity and to avoid replying to his question. She knew he was aware of her answer already, and this scared her – how he could read her easily.
He looked at the seat. "Yes. I know how you hate that your things get crumpled and dirty" he glanced back at her with a neutral expression. "I got it from the stage before the dancers would step on it with their heels", he explained.
Blair reasoned about his words. He retrieved her dress from the stage before it could get dirty. He knew that she hated what wasn't clean and it surprised her. This simple statement from him moved something in her chest. "Thanks" she murmured with a smile.
He shrugged his shoulders and his eyes met with hers again. Then he moved closer to her - even closer than he had done few minutes before – until they were face to face and their noses could almost touch. Blair's heart started racing out of the blue and she put a hand there as if she was aiming to stop it from doing that. Chuck's stare was so deep she needed to blink and look down and sigh before she could actually gaze back at him. For a moment, he was different.
Into his eyes she was seeing something she had caught two hours before when they had sex the first time. Was it affection? Was it lust? She couldn't tell. She melted into Chuck's eyes and realized that they were of a caramel color and not the usual brown. There was a light in them that she couldn't name... And it allured her. It was as if he had stripped down and was showing his true soul. Or maybe she was being hypnotized and fooled, she couldn't figure it out.
At some point Chuck caressed her cheek and tucked her hair behind her ear and it made her shiver and close her eyes briefly in return. It was a small gesture, but it felt romantic. She realized Nate had never done something like this. He had been a caring boyfriend as much as a 16 year old guy could be, but he was rarely a romantic fella.
He put his other hand on her neck and leaned in until his mouth covered hers and they kissed. It was a slow and shy encounter at first then the rhythm intensified until they were both out of breath and leaned back. Blair put her forehead on his. "Why did you ask me if I was sure?"
"Because I wanted to give you a choice, Blair" he panted as he caressed her neck. "So you wouldn't regret it." His tone was firm, so she believed that he was telling the truth.
Chuck's words amazed her in a good way. He seemed... Caring. Concerned. Some things she had barely seen in him when he was in public. "Thank you" she whispered softly, "for giving me a choice. I appreciate that."
He looked up and smiled at her. Then his face grew sorrowful as he wondered more. "Tell me. Was it worth?"
"What?" she asked first. She meant it as an astonished question, but perhaps her inner self was questioning herself more about him in that moment. "I mean... Yes, it was."
His features seemed to relax as he grinned and kissed her again. She wasn't sure but he looked content about her reply. His hands started to work on her back as he gently laid her down on the long seat of the limo and hovered her. He touched the side of her leg and it made her shiver and make clear that she was pleased through a moan.
When Chuck went down between her knees and started kissing all the way up towards her inner thigh, she imagined the stars, the rainbows and the unicorns. Not that she really did that, but she felt like heaven. When his mouth reached the spot in the middle and placed several kisses over there, she grabbed his shoulders and pushed her head back in the seat with a louder moan, feeling the leather wet as she was starting to sweat. Then when he started licking, it was pure heaven. She never believed that such a simple touch could make her squeal. Rephrasing, she couldn't think that such a thing could be done by none other than Chuck Bass and make her squeal.
He teased at the hem of her chemise and followed his trail up on her belly button. But then Blair exploded when one of his hands captured one of her breasts and then her nipple under the texture. Her back arched and pushed her torso and hips towards him, until she cried out his name.
When his mouth left her skin, she grabbed his hair and stopped him to put herself in a sitting position. He had a questioning look upon his face, which she cared to elaborate. "This is not fair. You're completely dressed."
He looked amused by her matter-of-fact statement. He seemed to think about what to answer and in the end he didn't. He took her hands and placed them on the collar of his white shirt and undid the first button for her, all of this while he locked eyes with her. With expert hands despite she wasn't an expert in this field, Blair unbuttoned the shirt first and threw it away, then his pants until he was left with only his underwear on and the real interaction began.
After another hour, they laid on the floor of the limo with Chuck's suit jacket barely covering their bodies. Blair's head rested on his chest and her hands were on her belly, while his left arm hugged her in a possessive way. She had never lied down with a man that wasn't Nate, and this made her feel weird. It made her have a strange sensation in her chest and her stomach, and it wasn't a displeasing one. Maybe because she would always remember Chuck as her first. Who knew.
They had sex four times, without counting the teasing of the foreplay part. It was the first time Blair had this type of experience and so far, it was great. The only thing she couldn't digest yet was who had made this possible and enjoyable. She couldn't have predicted it.
They had remained silent for a while until Blair broke the religious silence. "I think I should probably go" she informed him, sitting down and taking her stuff from the floor. He simply nodded and let her go. She never made eye contact with him until she was fully dressed and he was too.
Before she opened the door of the car that had been parked under her building during the last two hours, she turned to glance at him. She couldn't read his expression properly, but he seemed a mix of overjoyed and mournful. Was it because she was going home?
He reached for the hand she put on the leather seat and squeezed it. "Goodnight, Blair."
She couldn't help but smile. "Goodnight, Chuck." And then she was out of his limo.
Chuck remained alone with his thoughts. He closed his eyes, took a breath, and focused on the floor. Replaying what had happened on this night alone drained him. For years he had wished to seal the deal with Blair because he was curious how she tasted. In his wild dreams, a girl like Blair was like a panther who would take the charge during the sexual act, which was a kind of woman who aroused him. But she needed a little push to discover her inner qualities. She was a good leader and had a strong character, but he knew that deep down, Blair was unsure of herself.
He hated to admit it, but what happened that night with her made him want to show her that she shouldn't be unsure, because she was beautiful like not even Serena was. Sure, Serena was like a ray of sunshine on a rainy day while Blair was more like a classic old Hollywood movie heroine that not everybody is able to appreciate, but for some reasons, the latter interested him more. There was just something about Blair that he hoped she could see, and it was her strength.
He realized that when Blair wasn't thinking about Nate, she dared to be different and let her bad girl side show up and take the lead, just like she had done in the back of the limo and on stage. She wasn't held back. He had more experience compared to her, but when Blair had grazed his naked body with her dainty hands, it seemed as if she was a natural in this.
The chemistry he felt when they had sex he had never felt it before. It made him ask if this happened because they were old acquaintances, but he believed this was unrelated. He had sex with other people several times but he didn't feel any pull whatsoever. He didn't feel his stomach empty after every touch of her, after every kiss, even after every spat.
He knew that she would probably hate him in the morning, but for the moment he didn't care because he felt thrilled and hopeful. He would never admit it that soon, but get in intimate contact with Blair Waldorf moved something in the depth of a heart he thought he'd lost. And this scared him to death.