Disclaimer: I do not own Gossip Girl or "Happy Endings;" all characters and initial concepts/structures belong to their respective owners.
C.
When Blair Waldorf was twelve, she asked Chuck Bass to be her first kiss.
"Why?" he asked.
She shrugged one shoulder. "Because I want to be good for Nate."
Chuck frowned and ignored the disappointment churning in his stomach. The beating of his lovesick heart.
"Please?" She bit her bottom lip, embarrassment tinging her cheeks.
"Okay."
He sat her down on the couch next to him. He pressed his lips to hers for precisely three seconds. They broke apart.
"Thanks."
"Any time, Waldorf."
Blair left his house that day with a slight spring in her step. Both tried to ignore the butterflies.
When Blair Waldorf was fifteen, she asked Chuck Bass to make out with her.
"Why?" he asked.
She shrugged one shoulder. "Because I want to be good for Nate."
Chuck frowned and ignored the disappointment churning in his stomach. The beating of his lovesick heart.
"You and Nate haven't made out yet? Geez."
She blushed fiercely, turning to go. "Forget I asked."
"No, Blair." He grabbed her by the arm and pulled her back. "Sit, it's fine, I'll do it."
It was her turn to frown. "Well, don't make it sound like torture."
"Blair Waldorf, I would love to make out with the hot piece of ass that you are, so sit the fuck down so I can attack you with my lips."
She rolled her eyes. "Thanks, Chuck."
"Any time, Waldorf," he smirked before pulling her into his lap.
He leaned in to kiss her. Their lips brushed. She jerked back.
"I-I don't know how. You can't make fun of me."
"It's okay." He rubbed the small of her back with his hand. "Don't be so self-conscious, everyone has to learn how."
She nodded and he leaned in again. They kissed. He coaxed her mouth open with his tongue.
He didn't realize he was opening the Blair Waldorf edition of Pandora's Box, featuring pent-up sexual frustration and serious tongue dexterity.
Time passed. Chuck didn't know how much. How could he with Blair Waldorf kissing him like the world was ending tomorrow? But he did know that his leg was falling asleep.
He grunted.
"What?"
"My leg is asleep."
She looked down at how they were sitting, pursing her swollen lips. "Sorry." She swung her legs over and straddled him. Her skirt inched up towards her waist.
"My, my," Chuck drawled, "what a risqué position for such an innocent young girl."
Her cheeks turned pink. "Shut up."
He smirked. "Anyone ever tell you you're a good kisser, Waldorf?"
"Well, Serena did this one time in Aspen…"
Chuck coughed. "What?"
A smile touched the corners of her lips and she kissed him again.
Pressing against Blair's innocent, untouched inner thigh was the bulge in Chuck's pants. If she just moved her hips slightly then it could press against her underwear…
"What are you doing?"
She looked away.
"B, look at me."
Her eyes reluctantly made their way back to his face.
"Have you ever… touched yourself?"
"Pardon?"
"Have you ever masturbated?"
"… No."
"God, you're totally pure," he muttered to himself.
She stood up and smoothed down her skirt. "Sorry."
"It's not a bad thing I just… I can't be the one to corrupt you."
"Excuse me?"
"You want to, er, feel things that I can make you feel, but they're not my place to make you feel."
"Are you saying that you think I want you to have sex with me?"
"No, I'm saying that you want me to make you come."
Blair narrowed her eyes.
"It's not a bad thing. Trust me, I want to make you come. There is nothing I would like to do more right now. But I just can't. I'm not your boyfriend."
"My boyfriend doesn't want to do anything with me, so, whatever."
"Come on, B, you know that's not true."
"It is true!" Her bottom lip quivered. "Nate would rather be jacking off while thinking of Serena than get physical with me. Don't you dare deny it."
Silence.
"Well, Nate's a fucking idiot. You're twenty times hotter than Serena, and I'm not just saying that to make you feel better."
"Yeah, you are."
"I'm not. I think about you when I jack off."
Blair scrunched up her nose. "Huh?"
"You heard me."
Her eyes brightened.
"That's kind of gross."
He laughed. "But you like knowing that I do, don't you?"
"Well, yeah…"
"Who knew you'd be such a slut at heart?"
She grinned cheekily. "Serena did."
"Oh, right, Aspen. Why don't you tell me about Aspen?"
"I can't, I should get going," she leaned in and pecked him on the cheek. "I have to go change my underwear before I meet the girls for lunch."
"You're a fucking tease."
"Hey, you almost had me today," she giggled as she floated out the door, tossing the door shut behind her.
Blair left his house that day with a spring in her step. Both tried to ignore the butterflies.
When Blair Waldorf was sixteen, she asked Chuck Bass to go to third with her.
"Why?" he asked.
She shrugged one shoulder. "Because I'm horny."
Chuck's eyebrows furrowed together. "Now?"
"For like the last six months."
He smirked. "Nate not satisfying you, Princess?"
"Nate's not doing anything, period," she sighed, stretching out on his bed. She pressed a pillow over her face and sighed loudly.
"And your fingers aren't doing the trick? A vibrator, perhaps?"
"Obviously not, Chuck," she snapped, pulling the pillow off her face and sitting up to glare at him. "So make a fucking choice before I die from the female equivalent of blue balls."
The pillow came over Blair's face again and she flopped back.
The bed dipped beside her. A warm finger traced the skin of her pale collar, dipping just below her dress to tease the tops of her breasts.
"So you're saying that you have an itch only I can scratch, hm?"
"Stop fucking with me, Bass!" she growled, whipping the pillow off her face and smacking him with it. "I really, really need you to do this for me."
He laughed, pinning her down easily, one hand holding her two wrists above her head. She squirmed against him.
"You're hot when you're horny," Chuck said against her skin, pressing a kiss to the flesh behind her ear.
She held back a whimper. "Please don't start if you're not going to follow through. I swear on Audrey that I'll cry if you're just going to stop."
"I'm your boyfriend's best friend, are you sure you're okay with this?" He licked at her neck.
Her head fell back and she screwed her eyes shut, hips involuntarily rising to meet his. "It doesn't matter. I don't care… I just… I need…"
He frowned. "I don't want you to regret it, though. I don't want to take something special away from you."
"You're not. The special thing was already taken away from me so just don't worry about it."
"Hm?"
"You can't tell Nate any of this, by the way."
She closed her eyes again, fighting off tears. She wiped at her eyes.
Chuck rolled off of her and pulled her up by her arm into a sitting position. "Are you okay?"
"I'm fine." Her nostrils flared.
"Seriously, B, what's wrong?"
"I know about Serena and Nate!" she sobbed, burying her face in her hands. "I know they had sex, okay?"
"I-"
"-Why didn't you tell me? I know Nate's your best friend, but I'm your friend too."
"I was trying to protect you." He rubbed her shoulder.
"That's a fucked up way of trying to protect me," she shrugged off his hand, moving away from him. "It's not like I haven't known about their undying love for years."
"I'm really sorry. I was going to tell you but I just… I couldn't."
"Whatever." Blair pulled a pillow into her lap and picked at the corner of it with her nail. "I guess it's better now that I have an excuse to break up with him."
"Are you serious?"
"Yeah, I haven't loved Nate for, like, years." She shrugged, pursing her lips. "I guess… I don't know, I want love like Audrey Hepburn and Gregory Peck. Not like… I don't know. I just couldn't break up with Nate cause, like, we're the golden couple, you know?"
He snorted. "Trust me, I know."
She stared at him for a moment. "Whatever. I'm just mad because Serena's supposed to be my best friend."
"That's kind of the pot calling the kettle black, don't you think?"
"This is different." She kicked her shoes off and started pulling at the tightly tucked in sheets. "I didn't come over here to get revenge. I really am horny, and you're Chuck Bass. I figured that Nate officially doesn't want me, so, you know, here I am."
He watched as she fluffed a pillow and climbed into bed, hugging her arms around her.
"Can you do me a favor?" Blair asked.
"Mm?"
"Will you hold me?"
"Sure."
He followed her into bed, wrapping his arm around her stomach and pulling her back into his chest.
Silence.
He kissed the top of her head.
"What was that for?"
"You know you're beautiful, right?"
"Huh?"
"Nate had sex with Serena because he's stupid. Trust me, you have nothing to be insecure about."
She turned in his arms, a slight smile on her face. "Why are you telling me this?"
"Because you're quite honestly the most gorgeous girl I've ever laid my eyes on, so… Yeah."
"Eloquent," she laughed.
He blushed.
"I don't think I've ever seen you blush before."
"I don't blush very easily."
"But I make you blush?"
"Sometimes, yeah."
"You make me blush too."
"You blush all the time."
"But not like… this. You know what I mean."
"I do, I do, I'm just teasing."
Blair giggled as she pulled herself up his body, pressing her forehead against his.
Chuck leaned in and kissed her.
She pulled back. "I don't want this to be a pity thing."
"Don't worry, it's not."
Blair smiled and rolled onto her back, pulling him on top of her. He went straight for her neck, sucking and kissing at the soft skin until he'd left multiple bruises all over. Marking her as his. His fingers traveled under the hem of her dress, massaging up her thigh until he reached the lace of her underwear.
He paused. "Do you still want me to…?"
She nodded, sucking in a breath.
His fingers dipped under the fabric and into…
"Ah," Blair sighed.
Whimpers and moans later, she came. A tear leaked out of her eye. He kissed it away.
"Thank you," she said when the feeling came back to her legs.
"Any time, Waldorf."
She fell asleep in his arms. He watched her as long as he could before falling asleep himself.
Blair left his house the next morning (scarf wrapped around her neck to hide the hickeys) with a spring in her step. Both tried to ignore the butterflies.
When Blair Waldorf was seventeen, she asked Chuck Bass to take her virginity.
"Why?" he asked.
She shrugged one shoulder. "Because I want my first time to be special."
"And it would be special with me?"
"Well… yeah."
He folded his arms behind his head and leaned against the headboard of his bed. "I've never heard that before."
"I just, I feel like I'm never going to lose my virginity, you know?" she rolled onto her back and let her torso slip off the bed until she was upside down, staring at the window. "Nate was, like, my safety net and now he's just screwing Serena left and right. Which is fine cause I dumped him, but, whatever."
Chuck frowned. "I thought you had a gaggle of potential suitors salivating at the chance of boning you. Go ask one of them."
"Ew, no, they're so grimy. Do you not want me or something?"
"No, I don't."
She sat up. "Are you serious?"
"I don't want to be just your back up fuck, Blair. Sorry, but no."
"I mean, you're not just my back up fuck. You're Chuck."
"Exactly. I'm Chuck," he sneered. "Is that how you see me? As your ex-boyfriend's sex machine best friend? Is that all I am?"
She rolled her eyes and threw a pillow at him. "Shut up, you know you're my best friend."
"How the fuck am I supposed to know that?"
"You're the first person I call when I wake up and the last person I text before I go to sleep. I tell you more crap than I tell Serena. I trust you way more than Serena. You're my best friend." She shrugged nonchalantly. "And I know I'm your best friend too because Nate doesn't get you or your issues with Bart, but I do. I get you, Bass."
Silence.
"I see you as more than my 'ex-boyfriend's sex machine best friend,' that's such a stupid thing to think."
"But I'm just guy Serena."
"No, you're way more than that. What are you getting at?"
He looked away.
"Chuck, seriously. You can tell me anything."
"Do you ever feel… butterflies?"
"What?"
"When I'm around you…" he trailed off, searching for the words. "I feel… like my stomach is fluttering and I can hear my heart beating and I just want to kiss you all the fucking time."
"I-"
"-Let me finish. I've never, well, I don't think anyone's ever loved me, so I'm not really sure what love is. But I'm pretty sure that I'm in love with you. So, I can't be your last resort fuck because I want to be more than that."
She crawled off the bed. He thought he was going to throw up.
"God, fuck, I take it back, I didn't say any of that. Pretend that didn't happen."
"No! No. Don't you dare take it back." She grinned and retrieved his scarf from the chair in the corner. "I can't believe you haven't noticed this yet."
Beneath the tag was her glittering gold heart pin.
"Is that…?"
"Yeah."
"Does that mean-"
"-Yeah."
He pulled her into his lap. "Am I your new Nate?"
"No, you're my Chuck."
"What does that mean?"
"It means that, as your girlfriend, I officially claim your scarf as mine. And I will flaunt it in the face of any old conquests who dare to flirt with you again. Or anyone who dares to flirt with you ever. Except for Nate, since you guys are in some weird bromance. Oh, and other than myself, because I'm your girlfriend and that's my right."
He smirked. "You're chatty."
"I ramble when I'm sublimely happy."
She pecked him on the lips.
"You know I'm gonna be a shitty boyfriend, right? I have no fucking idea what I'm supposed to do."
"Zip it, you'll be amazing. I'll teach you."
He rolled them over, pressing his body into hers. "And I'll teach you some things about sex, starting with the most effective places to rip a dress."
"No!" She flailed against him. "I like this dress. Seriously, I'll castrate you. Don't. Your balls are your best asset."
Blair left his house the next morning in baggy jeans and a men's dress shirt, no longer a virgin, practically skipping down the sidewalk.
Everything continues as in A.