In the future, Blair Waldorf would always wonder if had she known, would she have changed her stars? If she could know, would she have stopped him from ruining her?
It was the winter holiday after her fifteenth birthday and she was elated to be home in New York. It was her city, and while boarding school in Switzerland was... what it was, nothing was like home, in New York, with her childhood friends. Bendel's and Bergdorf's and Barney's with Serena, feeding ducks in the park with Dorota, ice-skating with daddy, it was everything she could want. There was all the gossip to catch up on, lazy afternoons in bed watching movies and reading magazines- alone, or with Serena, and they were at the age where watching boys had become even more enjoyable than before.
It was one of these lazy afternoons that it started. Stepping off the elevator, into the van der Woodsen penthouse, Blair heard deep laughter. Turning the corner, she saw Serena's stepbrother, Chuck Bass, with no doubt a fellow lecherous friend, in tow.
She had grown up watching him, the older brother of her best friend. Bart and Lily married when Chuck was seven, Blair and Serena were five, and Eric was barely three. So, Chuck became a requisite satellite in their little universe. He naturally disapproved of having to take his step-sister anywhere with him, no matter their age, and he was always happy for Blair to join so that he had to worry about his very blonde sister staying out of trouble a little bit less.
But Blair, with her keen brown eyes, had found him cute in their youth. Once, when she was seven, he carried her home on his back when the strap on one of her Mary Jane's broke. He complained the entire time, but he still insisted on carrying her. She adored the little times he would ever pay her attention. The age difference always felt so large when they were children, and Blair was too infatuated with him to ever risk exposing her emotion.
There was one afternoon when she was eleven, after watching too many Disney movies in one sitting, she did think of at last proclaiming her 'love' for him. She went so far as to put on her best headband and march herself over to their penthouse. Only to find him heavily kissing another girl on the sofa. Horrified, she swore to never watch Disney movies ever again- at least, not more than one per day. However, looking at him now? She swallowed hard, her sweet feelings towards a childhood crush suddenly taking on much more tangible sensations.
He was tall and dark, more mature looking- more mature overall, than the boys her own age, at a well worn seventeen. He glanced at her briefly as he and his friend passed her on their way out. For a moment, his gaze lingered on her, quickly assessing her presence. He looked at her like a guppy in the big fish pond, hardly noticing her as being much of anything to him, and going on his way.
Blair's cheeks flared pink. She had been feeling more and more differently around boys for a while but looking at Chuck just now? She was embarrassed at how he made her feel; he had become incredibly handsome and it made her knees weak. Her mind instantly pondered him doing a myriad of very bad bad things to her. She had to stop in the guest bathroom a moment before finding Serena. Her best friend would notice her flushed face and that was unacceptable. She ran the cool water over her hands, trying to sap the heat from her veins.
When she entered Serena's room, her step was once again light, "Hey, S."
"Hey, B!" The other girl was laid out on her bed with the latest issue of Vogue.
"I just saw Chuck leave; we have the whole penthouse to ourselves!" Blair bubbled.
"Oh thank heavens. You are so lucky you go away to school. No girl should have to grow up cohabiting with... that." Serena tossed the magazine aside.
"Only the best for Harold and Eleanor's only daughter!" Blair sighed and flopped down onto Serena's bed, her thoughts turning to Chuck, "What do you mean about Chuck? Has he changed much since the summer?" Blair was confused with the tone, ire? in Serena's voice.
"Not so much- but the sex! Mom and dad are at the other end of the penthouse- though I don't know how they don't still hear him. If I try and say anything to him, he just glowers at me, saying I can't understand it, and that he has a reputation to uphold." Serena tousled her hair, "A girl needs her beauty sleep you know."
Blair listened intently, trying to restrain her imagination- Chuck, doing... things... to numerous faceless girls. When Serena flipped her hair though, she had to laugh, "Like you need to worry about beauty sleep!"
"Well, I'm not getting any younger," the blonde quipped.
"You sound like Lily." Blair laughed again.
That afternoon the girls relaxed, eating macarons and watching old Hollywood movies. In their glutton induced states, they both lay out on Serena's big bed and talked about everything and nothing at all.
"Don't you wonder what it's like? Especially having to listen to him?" Blair wondered aloud.
"What Chuck? Ew, I don't think about Chuck!" Serena grimaced.
"Not Chuck," Well, that is not what she was asking his sister, "Sex and... orgasm."
"Listening to it as often as I do?" Serena sighed in annoyance, "is a real turn off. I asked for a sound machine for Christmas."
"It can't really be that bad!" Blair balked.
Serena just raised her eyebrows. After a beat, she kicked her feet off the bed, "I want something to drink. Do you want anything?"
"Sure, I'll come with you." Blair slipped off the bed and followed behind her tall friend.
When Serena turned out of the hallway, Blair's steps slowed and her mouth became dry. Chuck had returned and was leaning lazily against the countertop. He cradled a tumbler of scotch between his fingertips and she watched with wide eyes as he tipped his head back. She took in every detail; the way the light hit his features, how his long eyelashes barely brushed skin when his eyes were closed, the way his mouth pressed against the glass, how his Adam's apple moved up... and down... his thick neck as he gulped the amber liquid.
She was completely mesmerized and her feet barely tried to shuffle down the hallway. They stopped completely when he turned towards her to walk to his room. Blair was engulfed in a wave of his cologne as he approached her, and for a moment his eyes were on her, and she felt her senses slipping.
"Nice headband, Waldorf."
He said her name! Sort of... and, he liked her headband? And with that he brushed passed her. Blair's skin was hot and she knew... she knew... the heat radiated from between her legs. She instinctively pressed her thighs together, once again wondering what all those girls were experiencing with him.
"B?" Serena called from around the corner.
Blair rubbed her temple, feigning discomfort, and shuffled the rest of the way into the kitchen, "Sorry, just feeling a bit of a headache coming on."
"Here," her friend pressed a glass of water into her hand, "I'll get you something to take for it."
Crawling up into one of the bar stools, Blair sipped the cool drink, feeling the heat drain from her face, and wiggling her hips a little, creating that good feeling. Of course she knew the birds and the bees, she knew what hormones were, and masturbating, and orgasm. But what she did not know was... what Chuck was doing to all these women. The cries and the screaming and the pleasure. Those are things they do not tell you- why does it happen? How does it happen? She had given herself little bits of pleasure before, but... she wanted to scream from it.
It was a week later that fate happened.
"S!" Blair was half running down the stairs in her home as she grasped her cell phone, "Where are you?"
"I'm out with Mom. She's debating several new pieces of art."
Blair could hear the false joy in her friend's voice, "No! I left my dress in your room, and Mom will be home from Paris soon- if I don't have that dress, I'm dead!"
"I'll let Vanya know to let you up, it's okay."
"Oh, thank you, S! I owe you!" She felt a flood of relief.
"Yes, yes you do. Next round of Dean & Deluca hot chocolates are on you!" The blonde laughed and the girls hung up their phones.
Entering the building, Vanya told her no one was home at the moment, so she would not be disturbing anyone. As Blair walked towards Serena's room, curiosity niggled in the back of her mind. After quickly retrieving her dress, she snuck into Chuck's room. Her heart pounded in her chest, nervous and excited. His room was done in dark, rich colors, and she could smell the scent of his cologne. This made her even more excited, and she sipped into his walk-in closet. She lifted the sleeve of one of his shirts, pressing it to her cheek. It was clean laundry, but she tried to imagine what his shirt might smell like at the end of the day, after cologne mingled with scotch and a little sweat. Burying her face in the fabric, she imagined the strength of his arms around her, the feel of the little white buttons popping open, the sight of the shirt rolling back off his broad shoulders. Blood was throbbing between her legs at the thought of it.
And then she heard a noise. Not a noise- noises! Suddenly, she heard Chuck tumbling onto his bed with a new conquest. Blair held her breath, counting her lucky stars she had not turned on any lights in his room. Serena was right- they were quite the noisemakers and she had no hesitation about scooting closer to the closet door. She had left it open a few inches, nudging it open a little more to peek out at them.
Chuck was ravishing the girl- he seemed to be all over her at once, touching, kissing, rubbing. Oddly, Blair noticed he was not keen on getting undressed- a few shirt buttons undone, and she was sure she turned red when he opened his trousers. Though, she was thankful she was not privy to seeing too much, for he was quick to... enjoy his partner's company, skillfully slipping on a condom rapidly before he sank into the depths of his newest conquest. Part of her brain knew what she was doing was wrong- she should not be here, should not be seeing this. Yet, she was trapped and the throbbing between her legs was becoming unbearable. Leaning against the wall, Blair slipped her hand under her skirt.
Her eyes were hot as she tried to study them, the way he was moving, kissing, touching her, and how the girl was responding to it. Her fingers felt good as she rubbed herself through her underwear; the heat was incredible and the sensation made her feel tingly. Before long, Chuck was making the girl scream with pleasure. Blair rubbed herself a little harder at this, desperate with envy. Her legs trembled a little, but it was hardly enough. She watched as Chuck came, he was as beautiful as she imagined as he spent himself. She gasped a little, wanting to cry with disappointment at her body's unwillingness to take her to such heights. They were done, and now so was she.
Shrinking back deep into the shadows, Blair listened, waiting for them to get up. She heard movement, and the girl going to take a shower. Sighing a little with relief, she knew it would be just a few more moments before she could make her escape. She heard the sink running and the girl squeal as she entered the shower.
Time to run for it. Peaking her head out, she saw that the room was clear. Blair had put barely a foot out of the closet when Chuck rounded the corner. His face was as cold as his form, and without even needing to touch her, he backed her into the closet. She gasped, nearly stumbling over her feet as she reeled backwards. Standing in the doorway, he blocked her exit, and with a casual turn of his hand, turned on the wardrobe lighting to a soft, low light.
Curled up, cornered against the wall and his rows of suits, Blair wanted to die, or be invisible, anything to escape the furious brown eyes that were staring directly at her. She trembled as she stood, petrified by her horror, unable to imagine what might happen now.
"I thought something felt off... and that I had heard something. Did you enjoy yourself, Blair?"
Her cheeks were burning and her whole body trembled with fear, "I'm sorry, I just..." He was bearing down on her, and she felt like her brain was shutting off.
"Did you at least get off on it?" He had her completely cornered now, and it was all she could do not to burst out in tears. His power rolled off of him- his scent, his presence, all overwhelming her. In her fear and frustration, she cracked.
"No!" she half cried, "I don't think I know how!"
"You don't..." Chuck paused and tilted his head, intrigued, "That's unacceptable."
"I want to scream like that..." Blair whispered, her eyes vacantly staring at a point of air past his shoulder- anything to not look at him.
One corner of Chuck's mouth upturned at her confession. He leaned his head down to hers, his mouth pressed against her ear, "Here..."
Blair swayed under him, as his hand slipped under her skirt.
"It's all about the touch," he purred in her ear. His finger dragged her underwear aside to rub against her wet, heated flesh. Blair's hips bucked against his hand with delight. Her fingers released the dress she had been clutching the entire time, her hands now raising to his shoulders, curling the fabric between her fists. Her legs parted more for him.
"Now, pay attention, Blair," He waited for her to nod against his chest as she clung to him, "This..." his thumb pressed roughly against the cleft of her sex, "is your clit, feel how much pleasure it gives you?"
Her mind swam as his thumb stroked her, her hips jolting against his hand uncontrollably. Blair eventually muttered some noise in the affirmative, her voice completely failing her.
"And this..." Chuck slid a finger inside her, listening to her gasp, her back arching, as he curled his finger inwards, pressing forward hard as he reached deep inside her. The pad of his thick finger began rubbing left, right... up... down... and then, in delicious little circles, which seemed to be her favorite, "is your g-spot," he chuckled a little, "very clearly not a myth."
By now Blair was hanging from him as she rode his hand. There were stars in her eyes as her head lolled back and she stared, unseeing, at the ceiling, her breath burning in her lungs. Just another moment, just another inch. It seemed as if he knew- knew what she needed, what it would take. "Let go, Blair. Come... come and scream for me."
The entire moment, every sensation felt like it was forced into this tiny point, burning low in her stomach. Him, her, his scent, his fingers, her hands on his shoulders, the deep tone of his voice, scream. And then it exploded. Her whole body shook against him, her hips bucking against his hand uncontrollably as her muscles clamped hard around the finger he had buried inside her. She could feel him smile against her hair as she screamed... screamed his name, over and over again, the sound tearing from her throat, slowly dying down to a quiet whimper as she sighed.
It would be the moment that would haunt her for the rest of her life, but for now, Blair Waldorf felt nothing but bliss.
She whimpered in protest when he pulled away from her. Swaying a moment, she had to look away from him when he stuck his finger in his mouth, "Sweet," he murmured.
The bliss was quickly receding to be replaced with shame and horror. Grabbing her dress, Blair fled from Chuck... from him, his closet, his room.
He chuckled to himself as he watched her run. One girl down, just one more to discard before he could enjoy an afternoon with his best friend and a bag of premium weed.
The remainder of Blair's holiday was spent trying to avoid going to Serena's penthouse. She had to go over once, just once, to say goodbye to Lily before returning to school in Switzerland.
Chuck was there, and he eyed her for a few moments with mild interest, a devilish upturn to his mouth. He said nothing the entire time, only sat at the breakfast table as if he were a stylish new piece of art his stepmother had recently acquired. He was eating a croissant with his fingers and it was all Blair could do to pry her eyes away from him as he sucked the layers of flaky pastry from his fingers. She tried to fight the color rising in her cheeks, but her underwear was a lost cause- soaked through in a minute at the sight of him.
He finished his breakfast just as she was beginning to depart. She thought she was safe, but… no. He made the briefest of pauses as he walked passed her, glancing down with his cat eyes as he purred, "What a sweet… headband," before he leisurely continued on back to his room. Blair pondered with slight horror if it were possible to become so incredibly aroused that it would run down your legs?
AN: This story has a special place in my heart. I was a true labor of love and I hope you can see that while you are reading. Please do consider reviewing as you read. It took a lot of amazing people to get this story off of my hard drive, so knowing you are enjoying it means a lot. xoxo -K
Cover art made by a fan, who wishes to remain anonymous, but thank you!