fic: with the cruelest of intentions (gossip girl; 1/3)

with the cruelest of intentions
Blair, Serena, Dan, Jenny. Some others, multi-pairing.
Based on Cruel Intentions. R. 20k words.
W: nothing you don't see in the movie, but just in case: underage sex, consent shadiness, general terrible humans.


Summary: Incestuous stepsisters Blair and Serena set out to seduce poor, innocent Dan Humphrey.


Note: For sing_song_sung! This was intended to be your Christmas fic, but it ended up being your birthday fic, so not too bad? I hope you enjoy it!





Serena knew she was a goner when Blair touched her thigh under the table at their parents' wedding, hand high enough to sneak under the short skirt of Serena's modified bridesmaid dress but low enough to do little more than tease. There'd been girlish, abortive experimentation when they were younger but nothing like that, nothing so brazen. Blair's hand swept up and her knuckles brushed Serena's cunt, not yet wet but wanting to be.

"You're such a slut," Blair laughed, pulling her hand away. "I knew you weren't wearing panties."

Serena cleared her throat and smiled, trying to reveal nothing like Blair revealed nothing but probably failing. "We both have reputations to uphold," she joked.

But it wasn't really a joke, of course. Reputation never was.







Blair watches Jenny Humphrey while she talks with the girls, taking stock of the things that make her laugh or sigh, the things that make her uncomfortable. Blair watches with an impenetrable smile on her own face, the true workings of her mind concealed behind it.

"It was really nice of you to have me over," Jenny says earnestly. Because she's new, she gives too much: "I was really afraid of not having any friends at school."

"Oh Jenny," Blair says. "Of course. We wouldn't want you to feel left out at all."

Around her, the other girls smile and nod, Kati and Iz and Penelope and Hazel lying through their smiling teeth just as much as Blair is.

"It's important to fall in with the right sort of people," Blair adds while the girls continue to nod around her. "The people you surround yourself with really do reflect on you."

Jenny nods too, emphatically, like she's taking each and every word to heart.

"Especially coming from public school." The girls exchange sympathetic glances and Blair leans in to lay a hand gently on Jenny's folded ones. "I'm not trying to be mean, Little J, honestly; it's just that you have so much more to work against than everyone else." She pats Jenny's hands again before sitting back. "But I can tell you're very dedicated to trying."

"I am," Jenny says immediately, like she's on a job interview. "I am super dedicated."

Blair smiles. "Then I'm sure you'll do just wonderfully, especially with us to help you."

Jenny smiles too.

"You better listen," comes another voice from somewhere near the doorway, "Or else you might end up like me."

Blair rolls her eyes without even looking around, through everyone else does, their backs suddenly straight and eyes eager. Serena has a way of exciting attention even with a relatively low-key entrance like that one.

"Jenny," Blair says. "I don't think you've met my sister."

"Step-sister," Serena corrects. She ambles over to one of the chaises, sunglasses hiding sleepless eyes and an iced coffee in one hand. Her free hand reaches for Jenny's in a brisk handshake.

"No, not yet," Jenny says. She's practically vibrating with the thrill of meeting the Serena van der Woodsen, most scandalous of socialites. Blair could honestly puke.

"Girls, would you mind if we cut our little luncheon short?" Blair says. "Serena and I have some family matters to discuss."

The girls dissipate ever so obligingly but Jenny lingers, taking too long to say her goodbyes. Blair fixes her smile again and promises to call Jenny the next day, which seems to cheer her up.

"Nice flowers," Jenny remarks as she leaves, fingering the blossoms on the table in the foyer.

"They're hydrangeas," Blair says, ushering her towards the elevator. "Goodbye, Little J." As soon as Jenny is in the elevator and the doors have closed behind her, Blair turns with a completely changed expression, utterly contemptuous. "God, what a vapid little twit."

Serena laughs as she stretches out on the chaise, kicking her heels over the side. "Why are you bothering, then?" she asks. "How much money does her family have?"

"None, to add insult to injury."

Serena's interest is piqued. "So what's the deal?"

Blair's silver cigarette case clicks open and she brings a bright red cigarette to her lips, gold filter against wet ruby gloss. She likes to coordinate them with her outfits, and today it is the only spot of real color against the navy-and-white uniform she still wears. It might come off ridiculous and affected on anyone else but Blair somehow carries it with class. "The deal, dear sister, is that sweet little Jenny Humphrey has attracted some attention that I'd rather she not have."

"For you, that's probably any attention at all," Serena jokes.

Blair gives her a look that is entirely unimpressed. "Do you remember Marcus Beaton?"

"That pathological liar who dumped you at the White Party?"

Blair's mouth tightens. "Yes. Well, as you can imagine, after all the effort I went through for him, I was quite distraught to find out he was after somebody new."

Serena pushes her sunglasses up to stare at Blair and then starts laughing. "You don't mean…?"

Blair wrinkles her nose. "Yes, that's right. As you may or may not remember, he's rather…obsessed with purity." That had been the final nail in the coffin for Blair and Marcus, so to speak; after weeks of dodging her advances, he'd given in and then summarily dumped her for being, in his words, "a tart." Apparently girls who enjoyed sex were not the type he'd bring home to his mother. "And Jenny is certainly pure."

"So what is it then?" Serena asks. "Friends close and enemies closer?"

"Something like that." She leans past Serena to drop ash into the ashtray, bringing them into very close proximity. Blair's voice lowers. "But I thought maybe you could help me. When I'm done with Jenny, I want her to be the premier tramp of the New York area. I want Marcus' little princess to be damaged goods."

Serena's gaze falls to Blair's mouth briefly. "What would that have to do with me?"

"Introduce her to your world of sex, drugs, and…what else do you do?"

Serena rolls her eyes, pushing Blair away and taking a sip of coffee. "Boring," she says. "She's such a try-hard, she'll be diving in before she even thinks any of it through. Do it yourself. Or better yet, just screw over Marcus; Jenny seemed nice."

"An indirect hit is always the most fatal. And you know I don't like things to be traced back to me," Blair says. "Everybody loves me and I intend to keep it that way."

"Any of the girls'll do it for you," Serena says, waving the whole thing off. "I have something else going on, anyway."

Blair sits back, pouting a little in an effort to guilt Serena, who has reached down to rifle through her purse until she pulls out a rolled-up copy of The New Yorker. "Page sixteen, please," Serena says, thrusting it out.

Blair accepts the magazine with a sigh, turning to the appropriate page. A quarter of it is dominated by a black and white photograph of a boy – dark hair, dark eyes, pursing lips. Clearly going for a moody, artistic thing. "'A Conversation with Rising Young Writer Dan Humphrey,'" Blair reads. "What is this?"

Serena leans in to point at a question towards the end of the page. "There."

The interviewer is asking something about a short story Dan Humphrey wrote, which leads into a question about sex. Blair arches an eyebrow. "'I'm choosing to wait,'" she reads. "'Sex is meaningful, like art, and you don't rush art.'" She drops the magazine and looks at Serena. "Are you fucking kidding me."

"Look at the picture, isn't he hot?" Serena says, scooping the magazine back up. "He's starting at our school soon."

"What he looks like is hardly the point," Blair says. "He sounds like a puritan and a virgin, which means he'll probably give it up like blinking and it'll take three seconds."

Serena laughs at that. "You were a puritan and a virgin too once upon a time," she teases. "He's sexy. And he's new. All of these other boys – they've known me forever." She looks down at the picture again with fondness, exasperating Blair. Everything's going to be ruined, and all because Serena has some stupid crush.

"He says he has a girlfriend," she remarks.

"Half the fun," Serena says.

Blair puts her cigarette out and leans back thoughtfully, fingers quickly loosening the bow at her throat and the first few buttons of her shirt. She feels Serena's gaze leave the pages and settle on her. "Jenny's last name is Humphrey; they must be siblings. Why not make a packaged deal of it?" Blair suggests. "Both Humphreys. Play them against each other. That'll be fun. Remember when you went out with those twins?"

"Not interested," Serena says.

"Are you really so set on him?" Blair says. "You don't seem like his type. I'd hate to see you get rejected."

Serena gives her a look. "You said he'd give it up like blinking."

"I was being facetious for effect," Blair says, well aware that Serena probably doesn't even know that word. "An intellectual hipster like this boy? They don't exactly go for the flighty socialite type. He'll want someone educated, knowledgeable, sophisticated; an equal, someone to challenge him. I mean, did you even read this?" She snatches the article back. "Look at all the namedropping. This boy wears his intellect like a shield. You'd never penetrate it."

Serena's eyes narrow. "You always underestimate me."

Blair smiles. "Hardly, sister dear. I'm just being realistic. He's a snob; that's his fault, not yours." She shrugs a little, reaching out to pat Serena's leg before she stands. "You don't stand a chance."

Serena is fully frowning now. "You wanna bet?"

Blair's smile widens playfully. "That could be fun," she allows, stalking towards the stairs. She hears Serena rise and follow her. "I do love a bet."

Serena bounds up the stairs ahead of her, turning to face Blair once she reaches the top. "Terms?"

"Hm…" Blair brushes past her and into her room, fingers already working at the rest of the buttons of her blouse. "If I win…" She turns suddenly to grin at Serena, who lingers in the doorway. "If I win, which I will, then you have to be clean, sober, and celibate." She pauses to relish that moment. "For the rest of the school year."

Serena makes a distasteful face as she steps into the room. She stretches out across the bed on her stomach, neckline of her dress pulling dangerously low. "And if I win?"

Blair gets on the bed beside Serena, lying on her back. She trails a light touch over her collarbone, down the center of her chest, over her stomach. "I'll give you something you've been obsessing about ever since our parents got married."

Serena raises her eyebrows even as her eyes follow the path of Blair's fingers. "I thought you didn't fuck girls."

Blair bites her lower lip, pushing the waist of her skirt a little lower as she turns toward Serena. "I might be convinced." Then she rises abruptly, hopping off the bed. "Providing, of course, that you can get the little hipster into bed."

"Don't worry," Serena says, watching as Blair continues to change, shrugging out of her shirt and into a silky, concealing robe almost immediately after. "It'll be easy as pie."







Serena tracks Dan Humphrey down to a poetry reading in a used bookstore in Brooklyn. She hits a couple of bars first so she'll be able to stand it, but even buzzed it's rough going; she's never been so bored in her life, not even during junior year American History. She fools around with a guy in the bathroom at one point just to pass the time but it's not even satisfying.

She takes her seat again just as Dan is getting up to the microphone, looking the part in a button down and open vest. He's obviously uncomfortable, but charmingly so – he's all wry smiles, downcast eyes. Serena likes his hands holding his small notebook. Nice hands, poetic hands, ink-stained hands. She doesn't pay attention to anything he's saying, too busy taking him in. She never had much patience for poetry anyway.

Afterwards as everyone is milling around, Serena sidles up next to him. "I saw you in The New Yorker," she says. "Your interview."

He blinks, seeming surprised that she's talking to him. He even looks side to side like it's somebody else she's after. "Uh, thanks?"

"I didn't say I liked it," Serena points out. She leans back against the table in front of him, shaking her hair back off her shoulders. "I mean, you're obviously talented, your short story was great, but the interview?" She shakes her head. "Awful."

"Awful?" he repeats blankly. "Uh, that's…that's one I haven't heard. Awful how?"

"All that stuff about sex," Serena says. "I mean, who are you to criticize something you've never experienced?"

Dan is quick to defend himself. "I'm not criticizing anything – I just think that it's a big deal and everyone pretends like it isn't. People should treat sex with the magnitude it deserves. You shouldn't experience the act of love until you're in love and kids our age aren't mature enough to feel those kinds of emotions." The abrupt flow of words ended, he looks awkward once again. Serena wonders if she could put an end to all this right now by just dragging him into the bathroom.

She laughs. "So God forbid I enjoy sex on its own merits then."

"I'm not trying to pass judgment," he says. "It's just my opinion. I'm not interested in your kind of lifestyle."

Serena looks at him for a beat, honestly a little offended, and says, "My kind of lifestyle?"

"You know," he says, "Blowing money on bullshit, drugs, partying, not cultivating any real connections or talents. It just seems really empty to me. I'm not interested. But if it's your thing, whatever, have at it."

Her brow furrows. "Wait, you know who I am?"

"Serena van der Woodsen," he says with a slight nod. The look on her face must be amusing, because he laughs a little. "Sorry, was it a secret? You're kind of all over the internet."

"I didn't think you read gossip sites," she says.

"I don't," he agrees. "Someone showed it to me. I figured I should read up about my future classmates." He touches her arm briefly in goodbye. "I gotta go. I'll see you in September, I guess."

"See you," Serena echoes, though she knows they'll be seeing each other again long before that. She just can't believe her whole approach has already gone up in smoke.

She's going to find out who showed him Gossip Girl and then she's going to sic Blair on them.







Blair arrives at the designated spot in the park roughly ten minutes early, Dorota struggling behind her with a picnic basket. Blair is usually early to things, either to scope out the situation or to happen upon someone doing something they shouldn't. Today is the latter.

Jenny is already there, her blonde hair falling out of its messy ponytail and into her face as she laughs, dodging a soccer ball kicked to her by none other than Nate Archibald. That gives Blair pause, her throat doing a funny, strangling thing like someone's got a hand on her neck. But then she smiles and moves forward, calling out, "Little J, did you forget about me?"

Jenny turns with comical abruptness, losing her footing and bashing into Nate, who catches her with an easy smile. "Jenny wants to try out for the girls' team," he informs Blair. "I'm helping her out."

"That's so nice of you," Blair says sweetly. She snaps for Dorota to set down the blanket and basket. "Mentoring the underclassman will look so good on your résumé – and you're so suited to it. Just like a big brother."

Both Jenny and Nate frown a little at that, faces mirroring discontentment.

"But unfortunately, Nate, I'm going to have to dismiss you," Blair says, still smiling. "Little J and I have a date."

Jenny watches Nate go with clear, distinct longing before she flops onto the blanket with a sigh, her fingers twisting in her lap. "I saw him when I was at school for orientation," Jenny says. Something about the wistful way she says it, I saw him, reminds Blair of herself.

Blair starts pulling food out of the basket, food she has no interest in or plans to eat. But still, for some reason, she snatches one of the wrapped-up lemon bars and takes a big bite. "Nate and I used to go out, did you know?"

Jenny's eyes go very wide, very fearful. "Um," she says.

"You probably didn't hear about it because it was so long ago," Blair says. "Before Gossip Girl, even. We were so young." Her smile widens and she laughs. "You don't have to look so nervous, Little J; Nate and I are just friends now. We were totally unsuited to each other."

"Oh," Jenny says with a nod, but she hardly seems to relax. Blair's eyes focus on her unwaveringly.

"You're going to be so popular at Constance, I can tell," she says. "I heard Marcus Beaton has been asking about you too."

"Oh," again, but this time with a laugh, Jenny dropping her gaze. "We went out once. It was kind of weird. He kept talking about this bulimic headcase he dumped at some party."

Blair's kind, open expression does not falter and she picks up a large chocolate chip cookie, breaking off a piece to pop in her mouth. "Bulimic headcase," she repeats. "Really."

"Yeah, he said she was crazy," Jenny says with another laugh. "Anyway. He invited me to a party at his Hamptons house for Labor Day weekend." Then she hesitates.

Blair seizes on that pause. "But?"

"I guess I'm nervous?" Jenny fidgets a little. "I mean, he's older…so sophisticated. I heard his mom is, like, a duchess or something."

"Or something," Blair mutters.

"And I've never had a boyfriend," Jenny continues awkwardly. "Or…anything."

Blair watches her, curiosity poorly disguised. "Jenny," she says, "Have you ever even kissed anyone?"

Jenny's cheeks go delicately pink and Blair is slightly envious, because she's never managed blushing on command. "No."

"Haven't you ever practiced with one of your girlfriends?"

"I never really had any girlfriends," Jenny says. "Also, ew."

Blair laughs softly. "How else do you think girls learn?" She sits up a little and takes off her sunglasses. "Alright, come here. I'll help you out."

Jenny seems a little reluctant as she shuffles forward on her knees, brushing strands of hair out of her face as she does so.

"Don't be scared," Blair teases. "I don't bite."

She tips Jenny's face up with a finger, holding back a scoff when Jenny's eyes fall shut with obedient immediacy. Blair keeps her own open, bored, as she presses her mouth to little Jenny Humphrey's. It's just too easy, and Blair abhors easy, as much as she'd been annoyed with Serena for feeling the same way. Jenny is too quick to please, too quick to give herself up; she pushes back into the kiss, a little noise catching in her throat.

Blair will have to barter with Gossip Girl to keep any pictures of this off the site; the incriminating sexts Penelope sent to her dad's junior partner should do nicely as a bargaining chip.

Blair pulls back impatiently. "See? That wasn't so bad."

Jenny's eyes open slowly, dreamily. "That was cool."

Blair is poking through the remaining desserts for something that isn't messy. Light and casual, she says, "You should try it on Nate sometime."

At that, Jenny's eyes snap wide. "What?"

Blair glances at her, laughing. "What do you mean what? He's so obviously into you. Trust me, I would know."

Jenny bites her lip, hesitation clear as she offers, "He did send me…kind of a love letter."

"A love letter?" Blair repeats, spine turning to steel. "That's so romantic. Did you write back?"

Jenny shakes her head.

"Well, don't you like him too?"

"I – I don't know," Jenny says.

"Little J. I thought we were friends."

Jenny's fingers start twisting in her lap again, a nervous habit. "Okay," she says, soft. "Okay. I do – I – I really do like him, I like him a lot, I can't stop thinking about him."

Perhaps too intent, Blair says, "So what's the problem?"

"I don't know," Jenny says with sudden teenage agony, arms going around herself. "My parents said I'm not allowed to date yet but I don't see why not, just because my brother was too much of a hermit to date when he was my age – and Dan, that's my brother, he thinks it's weird that all these older guys are interested in me, but Marcus is only three years older and Nate is only two, so I don't think it's that bad… And it's like, at my old school no boys were ever interested in me and I haven't even started Constance yet and now there are two."

Blair reaches out to rub Jenny's arm in an approximation of comfort. "Don't worry, alright? I told you I'd be here to help you with all of this. Bring me Nate's letters and I'll help you write the absolute perfect response ¬– he'll be eating out of the palm of your hand. Just don't tell your family and there'll be no problem." She smiles kindly. "Maybe we can even arrange a little get-together for you two at my place."

Jenny looks at her with complete, implicit trust. "Really? You'd do that for me?"

"I said we were friends, didn't I?"

"Best friends," Jenny says, and then she throws her arms around Blair in an impulsive hug. Blair frowns, patting Jenny's back lightly.

Blair wouldn't be Blair if she couldn't spin a situation her way.







Serena doesn't have any interest in being a stalker, but Dan Humphrey isn't giving her a lot of options. One tip to Gossip Girl to be on the lookout for him seems to do the trick. He's particularly insular, not socializing much outside of those eternal poetry readings and the occasional outing with his sister; Serena thinks he doesn't have any friends, and she wonders about that alleged girlfriend. She does find out that he was on the swim team at his old school, and he likes to go swimming late at night on weekends. She's giving up some prime parties, but Serena puts a bikini on under her mini-dress and hauls ass to Brooklyn once more.

The skeezy-looking guy at the front desk of the public pool informs her that they're closing in an hour, but Serena's done better work in less time. Some key flirtation gets him to promise that he won't let anyone else in. He informs her that there's only one guy here this late, anyway.

Serena steps into the big shadowy room, water reflecting on the walls and everything reeking of chlorine. Dan looks good in the water, a pale streak with good form slicing through dull blue water. Serena catcalls him, the sound echoing and echoing.

Dan pokes his head out, seeming startled until his gaze focuses on her. Then a sardonic sort of look settles over his expression and he swims slowly back towards her.

"Did the great Serena van der Woodsen actually step foot in a public pool in Brooklyn?" he says. "Or did your cab just break down out front by accident?"

"Ha ha," Serena says. If he's as well-versed in her bad behavior as he claimed, then he should know she's been in worse places than this. "I don't know about you, but I'm here to take a dip." She shimmies her dress up and over her head and then bends down gracefully to unlatch the clasps on either side of her strappy heels. "It's so hot out, isn't it?"

"Uh-huh…" Dan says, tone expressing extreme doubt but eyes undeniably trailing over her body. "Is this your move then?"

"My move?" Serena steps to the edge of the pool and slowly eases herself in.

"Though I guess just taking off your clothes isn't really a move, per se," he muses, drifting backwards. "Probably works as well as anything else."

"You know the pool at Constance is much nicer than this," she says. "I could show it to you sometime." Temptingly, "I have a key and everything, so we could have the whole place to ourselves."

"We have this whole place to ourselves," Dan points out. "How did you end up with a key?"

Serena smiles at him, playful and secretive. "Guess."

"Slept with the captain of the swim team?" he says pointedly. "I forgot ¬– that was on Gossip Girl too."

A little taken aback, Serena says, "You know, it isn't fair for you to not tell me who showed you that."

"I think it's pretty fair," Dan says, still drifting away from her. "The site's not a secret or anything."

Serena purses her lips a little. It was probably some jealous girl, maybe even one of Blair's friends; they sucked up to her face, but they were all backstabbers at heart. "Still. I'd like to know."

"Then I'm sorry to say you're going to be disappointed," he says.

Serena treads water, her long hair trailing on its surface. She hopes it doesn't turn her ends green or anything. "Why don't you like me?"

"I don't know you," Dan says.

"You sure act like you do," Serena points out. "Bringing up rumors and gossip – judging me on things I did in the past –"

He's looking at her with evident amusement. "It's amazing that someone as charming as you could be so manipulative," he says. "Look, I can tell you're coming on really strong for some reason, even if I don't get why. And I have a girlfriend. So. Pretty as you are…no thanks."

Momentarily put off by that – Blair is the manipulative one, not her– Serena nevertheless seizes an opportunity where she sees it. "Is it that crazy to think someone like me might be interested in someone like you?"

"Yes," he says bluntly. "You don't know anything about me."

Serena glides closer to him, dipping in and out of the water once so her hair streams out long and wet behind her. "I know your morals and values are important to you," she says. "And I envy that. I really do. It's a rare thing with the people I know. You're smart and cute and determined – basically everything a girl could ask for in a boyfriend."

"Determined?" he repeats, laughing. "Okay, that's one I've never heard."

Being laughed at bothers Serena; she's not used to uneven footing in situations like these. "I'll admit I'm not proud of everything I've done," she says, gaining speed with irritation, "but at least I own it. You're too busy being judgmental to even try and see me for who I am."

Actually seeming slightly chastised, Dan drops his gaze for a moment before looking back to her. "I'm really not trying to do that," he says, more gently. "We can be friends. That would be great. But I have a girlfriend."

Serena is close to him now, close enough that she could reach out and touch if she wanted. But she doesn't – not yet. "Are you sure?" she murmurs. "I've never seen her."

Dan's mouth opens and closes and then he says, "You're just not my type."

That had been almost exactly what Blair said, and it sets Serena's teeth on edge. We'll just see about that, she thinks. Serena is everybody's type. "Friends it is," she says easily. "I gotta go, but I'll see you soon, okay?"

He nods, appearing relieved. Serena swims back to the other side and hoists herself out, squeezing the water from her hair. She uses the towel – his towel – to pat her skin and ruffle her hair, and then she unties her bikini, letting both pieces hit the damp tile. She hears a rough cough behind her and smiles, glancing over her shoulder. "I just hate wet clothes, you know?"

She wiggles back into her dress and saunters out, leaving the bathing suit behind. It wasn't a total loss, she decides, but there's an uncertainty in the pit of her stomach that she's never felt before.

She doesn't know what to do with someone who doesn't want her.







It's early morning when Serena crawls into Blair's bed still in her party dress, hair coarse and messy from a combination of chlorine and sweat. "B," she says, drawing out the single syllable. She lifts Blair's face mask and lets it snap back against her skin. Blair bats her away. "B, I think Dan Humphrey's gay."

"If he is, he's not going to realize it until his sophomore year of college," Blair mumbles sleepily. "You still have time."

Serena gives an exasperated laugh. "That's not helpful."

"I wasn't trying to be helpful."

Serena cuddles closer, pouting a little, her hand slipping under Blair's pajama top to coast over her sleep-warm skin.

"Uh-uh," Blair laughs, just as Serena's fingertips brush the underside of her breast. She sits up, probably more awake than she'd been letting on, and takes her mask off. "You don’t get to admit defeat and still collect a prize."

"I'm not admitting defeat," Serena says. "I'm admitting…obstacles. He's so caught up in all this Gossip Girl stuff; totally ruined my element of surprise thing."

Blair slips out of bed and flounces over to her vanity to sit. She picks up her hairbrush and then glances back over her shoulder at Serena, looking too bright and too pretty for someone who'd just woken up. "I have a secret for you," she says. "What'll you give me for it?"

"That Marc Jacobs I just got," Serena says without missing a beat.

"I'd have to have it taken in so much I could probably make another dress with the extra fabric," Blair says, turning back to the mirror. "Next."

Serena rolls her eyes. "That satchel your mom got me from Bendel's?"

"There you go," Blair says, pleased. "Alright, I'll tell you, even though I crossed my heart, hoped to die that I wouldn't say a word." It's with positive glee that she slides another look Serena's way. "You've been wondering who showed him the website."

Serena sits up. "Who was it?"

Blair smiles. "None other than little Jenny Humphrey herself." A dismissive wave of the hand. "Not that she knew what she was doing. She's addicted to the site, couldn't help showing him all the most scandalous posts."

Serena purses her lips, feeling a little less vindictive but just as annoyed. "Great," she says. "Just great."

"Don't sound so put out," Blair says, something of a purr in her voice. She rises, making her way back to Serena. "If you think about it, it's quite perfect."

"How's that?" Serena asks, eyebrow raising.

"Well…you scratch my back…" Blair says, trailing off. "That dress makes you look like a streetwalker. No wonder you're scaring him off."

"You're such a bitch."

Blair traces the line of Serena's throat before her hand settles at its base, thumb pressing gently against the hollow. "Lucky you love me anyway."

Pushing back against Blair's hand slightly, Serena murmurs, "Yeah, lucky."

"I like to work alone, but we were always better as a team," Blair says. "I've been trying to get Jenny and Nate to act on their desires but they're taking too long. I need somebody to take care of Jenny before Labor Day."

"So I fuck with the freshman for you; what do I get out of the deal?"

Blair's hand moves over Serena's collarbone, the slope of her chest. Jenny's a sophomore, but Blair doesn't bother to correct her. "Dan Humphrey has expressed a desire in both the honor society and student government; as reigning class president, it's my job to meet with him." Her fingertips catch on the fabric of Serena's dress before closing on the tab of her zipper. "I can explain that he's got the wrong idea about my lovely sister, even though it isn't the wrong idea at all."

Serena wets her lips as she feels her dress begin to split at the side. "And then?"

"And then you get what you really want," Blair murmurs, leaning in, "Me. Do you accept?"

Their lips have barely brushed when Serena breathes, "Yes," and Blair pulls back, all business.

"Good," she says, smiling. "I'm going down for breakfast. You really ought to take a shower; you reek."

She wiggles her fingers at Serena in a wave before she exits the room and Serena just sits there in a disbelieving lump, though she can't say she's entirely surprised. Blair practically invented the word tease, after all.

Instead of getting up Serena gets off, nestled amongst the bedding with her hand between her legs.







Blair watches Dan from across the courtyard like prey, cataloguing anything that might prove useful later. He's talking animatedly to some teachers, utterly focused and too eager even from a distance. His enthusiasm is so genuine as to be off-putting, a puppy tripping over its own legs. Loser.

Still, she can't remember ever seeing the faculty here put so much effort into courting a scholarship student before. Usually the honors luncheons are only for currently matriculating students but she knows for a fact he was summoned by personal invitation. That means he must be smart. Very smart. Almost as smart as Blair, perhaps.

He's better looking in person, she notices.

Headmistress Queller introduces them before departing to cozy up to a benefactor. She'd attempted to facilitate some small talk, giving quite the list of Blair's accomplishments and accolades. Blair couldn't help preening a little under the attention; she always likes hearing things like that announced aloud. Dan's expression is unreadable, however, neither intimidated nor impressed but simply neutral.

"They keep you busy at this place, huh," he says, lifting his glass of punch for a sip. Blair bets he didn't even spike it. Her own drink is mostly champagne with a splash of fruit juice.

"It's a highly competitive environment," Blair says, then recites the words on every Constance-St. Jude's pamphlet, "Encouraging healthy competition is the first step towards success."

Dan gives her an odd, curious look. "Maybe that's why you guys have to let off so much steam."

"Don’t be so uptight, Dan Humphrey," she says. Her smile is pleasant, nonthreatening. "We like to have our fun, it's true, but we work harder than we play. I'm afraid you have the wrong idea about us Constance girls."

"Oh?"

She leans in a touch conspiratorially. "She'd kill me, but I can't help saying it – my sister, Serena, she has this massive thing for you. Ever since she saw your picture in that magazine she's been – oh, all a-flutter." Blair punctuates the sentence with a flutter of her own lashes, hand posed elegantly over her heart. "It's just driving her crazy that you won't give her a second look. Most guys aren't like that with Serena."

"I know," Dan says. "I read all about it."

"How would you like it if people made snap judgments on you based on what they'd read, hm?" Blair says. "I know I have a bias, but Serena's the best person I know. Her rep is mostly bullshit. I mean, you know how jealous people can be."

He shrugs, and then remarks, "I don't remember seeing much about you."

It stings a little in the way it always does when she's actively reminded of the amount of attention Serena receives just for tossing her hair, but Blair has spent the last three years crafting a specific persona that she'd take any day over Serena's transient, candle-flame success. Or so she tells herself. Blair is a girl who believes in long cons.

"I'm not much of a partier, true," she says. "As you said, I'm very busy."

His concentration is waning, gaze slipping away. God, this boy would actually rather talk to teachers than her.

"I'm just doing my familial duty," Blair adds. "I'd be remiss if I didn't. I hate to see Serena upset."

With some amusement, Dan's eyes find hers again, his just as dark but a good deal warmer. "She doesn't have a crush on me," he says flatly. "I don't know what rich kid bullshit is going on behind the scenes here, but I do know that the Serena van der Woodsens of the world do not have crushes on nobody writers from Brooklyn who they only met twice."

It's logic that would be difficult to argue with if she were anyone else. "No one can win with you, can they, Humphrey? You're so set in your ways."

"It's not about winning," he says.

Everything's about winning, Blair thinks, but what she says is, "It wouldn't kill you to go on a date with a pretty girl. You should lighten up."

"Back at you, il presidente," he says. He salutes her before moving off, leaving Blair standing there holding her drink, making calculations.

She is just light enough, thank you very much.







Jenny takes in the club with wide eyes, lips closed around the straw of her drink, seeming impossibly innocent beneath the flashing lights. She'd actually asked for a diet Coke, though Serena got her one spiced up with rum.

"This is really nice of you," Jenny says loudly over the music, ever so polite. "Everyone's been so nice to me!"

It'd be enough to break Serena's heart if she wasn't already so far gone herself, feeling hazy and blunted by whatever it was Carter Baizen gave her before she got here. This is Serena's second club of the night and it certainly won't be her last; she knows she should be playing the good girl because of the whole Dan scheme but it's hard to keep away. Too hard. She'd been glad for the excuse to dive back in totally, so she overindulged a little and now the inside of her head is blurry, golden, and she finds it hard to care about Jenny Humphrey's feelings.

"No problem," Serena answers. Her smile is wide and deceptively happy. She knows the lines she's supposed to say without really having to think about them. "You're just such a sweetheart!"

Jenny is pleased, her cheeks pink with the heat and her own excitement, the booze starting to circulate in her body. She looks how Serena probably looked once upon a time: lanky but beautiful, very young and carefree, powerful without realizing how just yet. She just looks like she's having fun. Serena was already a legendary party girl by the time she was Jenny's age.

Two more clubs and Jenny becomes warmly familiar, leaning unsteadily into Serena's side as she laughs. She was coaxed into a few more drinks and her limbs are infused with a buzzing easiness that makes her ungainly on her cheap heels. Serena should probably be unconscious at this point with all the things she's put into her body but, well, she's always had a high tolerance.

"I told my parents I was sleeping over at a friend's house," Jenny says, arm slung around Serena's neck and sweet little heart-shaped face upturned. "I hope you don't mind?"

"Not at all." Serena tucks some of Jenny's hair back behind her ear, touches her pink cheek. "Not at all."

Laughing and shushing each other, they fall out of the elevator into Serena's place, though the only person likely to be home is Blair and she'd never interrupt; the parents are always away on business or pleasure. The dark apartment feels large and echo-y. Serena takes off her heels before going upstairs, leaving them strewn casually at the foot of the steps, and Jenny does the same, though she keeps hers with her, held protectively in the crook of her arm.

"You know," Serena says once the door to her bedroom has closed on them, "Blair told me about your crush on Nate." Her voice is the voice of a thousand girlish sleepovers, conspiratorial and persuasive. "Don't be mad. She just thought maybe I could help."

Jenny is probably too drunk to be really mad, but she is nevertheless put out, her lips pursing and brow furrowing. Then, "Help how?"

"I have lots of experience with boys," Serena says, laughing. She gives Jenny a gentle push and the other girl goes sprawling over the bedspread, also giggling. "That's how."

"Okay," Jenny says. "What should I do?" She stretches a little, wriggles, getting comfortable. The strap of her dress falls off one shoulder.

Serena crawls up beside her. "What does he say in his letters?"

Jenny glances at her before bursting into a fresh fit of giggles. Her hands come up to cover her face. "I don't know," she says in the tone of someone who definitely does. "Um. That he cares about me. And he can't hide the way he feels. He said –" Her hands slide down enough to reveal luminous blue eyes, but her mouth remains muffled. "He said what he feels is too serious to pretend it doesn't exist."

Serena finds herself swallowing surprisingly hard and then she blinks and it's gone. "Can I tell you a secret?" she says softly, moving close. "Something not even Blair knows?"

Jenny's eyes widen and she nods, thrilled.

"Nate and I fooled around a couple of times… Forever ago. He's a really good guy, you know." That's all it was at the end of the day, fooling around a couple of times when they were both too young to know any better. Not that Serena would ever know better. "You like him a lot, huh?"

Jenny nods again.

"Let's write a letter back," Serena suggests.

They tear some notepaper from one of Serena's unused schoolbooks and Jenny flops on her stomach, poised with a bright blue pen in hand.

"You have to decide if you want it to be romantic or sexy," Serena tells her.

"I'm not good at sexy," Jenny says uncertainly.

"Only because you're a virgin." More teasingly, tucked close against Jenny's side, she says, "Tell him he makes you wet."

Jenny drops her forehead onto the paper, embarrassed laughter filling the air once more. "Oh my god, I cannot say that."

"Why, isn't it true?" Serena says, still teasing. Her fingers dance over Jenny's side, tickling her to get more of that laughter, and then unexpectedly they dive under Jenny's skirt, slide between her thighs. "Ha. See, I knew it."

Jenny gives a little surprised gasp, but the giggles are still on her lips.

"He's really hot," Serena says, almost conversational. Her hand slips past lace panties to find waiting heat, Jenny's clit hard and ready against her fingertips. Jenny's breath catches. "Don't you think so? Really great hands. And his shoulders, god."

"Y-yeah," Jenny says, eyes falling half-closed as she shifts against Serena's hand.

The first time with Blair had gone something like this. They'd been drunk, the first time Blair had ever gotten really drunk; it was before they were sisters, during the last of Blair's annual sleepovers, at the exact age when the whole idea was beginning to feel silly and passé. Blair and Serena shared a sleeping bag because they always did before but they were probably too old for it. All the other girls were asleep or pretending to be and Blair was easy and happy like Jenny, bubbly with booze. So Serena snaked her hand between Blair's pressed-together thighs, rubbing inexpertly through her panties until Serena felt Blair clench, heard Blair's breathing stutter. That first time Blair had even returned the favor.

Serena doesn't expect as much from Jenny, though. It's enough to get the other girl out of her off-the-rack dress, polyester panties and plaid-patterned bra, to hold her legs apart and give her the most confusing orgasm of her young life, and possibly the first too. "Don't tell your brother, okay," Serena says before her mouth dips back between Jenny's legs, hand sliding up to cup Jenny's breast. Serena thinks about how sweet it'll be to have Dan in bed, how maybe he'll press a hand over his face and tug at his own hair like Jenny does; maybe after he'll look just as dazed and distantly pleased, but he'll reach for Serena too, he'll want more, want everything.







Blair is enjoying breakfast in bed (parfait, black coffee, whole wheat toast no butter) when the bathroom door crashes open, framing tousle-haired Jenny wrapped up in a comforter with last night's eyeliner smeared beneath her eyes.

Blair lifts her cup. "Ever hear of knocking, Little J?"

Jenny seems not to hear her as she lands on the foot of Blair's bed, jostling her breakfast tray. Blair tries not to show visible annoyance.

"Something happened," Jenny says.

Blair arches an eyebrow, taking her in. "I can tell." But then she shakes her head slightly, reminding herself that Jenny requires a softer approach – it's difficult to be on her game so early in the morning. Blair schools her expression into something much more open and sets her tray aside so she can lean forward, ready to listen. "Tell me what happened, Jenny."

Jenny's brows draw together and she sinks deeper into the comforter, pulling it up around her ears. "It's…" She bites her lower lip. "It's Serena."

"You went out with her last night, right?" Blair asks carefully. "Did something happen then?"

"No, that was okay," Jenny murmurs. "It was after."

Blair waits but when nothing is forthcoming she needles a little. "Well?"

Jenny takes another long moment to chew her lower lip before launching forward and murmuring in Blair's ear. Blair tries not to laugh.

"She went down on you," Blair says. Jenny nods tremulously and then collapses in a blanketed heap, completely submerged. With slight impatience, Blair peels the comforter back until Jenny's troubled face is revealed again. "Well, didn't you like it?"

Going very red, Jenny shrugs. "I'm not…that way."

"Of course you're not." Blair hops up off the bed, reaching for her robe, gauzy and white. "You're practicing." At Jenny's slightly confused look, Blair explains, "Remember when I kissed you at the park? It was practice. This is what friends do, help each other." She fingers the dress Dorota has set out for her today, a royal blue construction of her mother's. "Consider Serena a tutor. A guide. I can help you with everything at school, and Serena can help you with this." Musingly, "As long as you don't enjoy it too much – that makes you a lez."

Jenny appears dubious. "What, like a sex tutor?"

Blair laughs. "Something like that. You want to please Nate when the time is right, don't you? And practice makes perfect." Perhaps putting too fine a point on it, she adds, "You should practice with as many people as possible."

Jenny opens her mouth, shuts it. Then, with the air of someone asking a dumb question, she ventures, "But I only love Nate?"

Blair has to bite her tongue sharply. She turns away, shedding her pajamas and slipping into today's lingerie, careless of Jenny seeing her. "Which is why you want to make him happy." She snatches the dress from its hanger and steps into it. "Zip me."

Jenny rises but doesn't reach for the zipper immediately. Over Blair's shoulder, their eyes meet in the mirror. "Isn't this…kind of slutty?"

"Everybody does it, Little J." Blair suppresses a sigh and turns to take Jenny's hands in hers. "Just remember that whatever you do, you're doing it for Nate."

Jenny looks at Blair with such impossible trust. "What if people…say things about me?"

"You're one of us now, Jenny. If you want to be part of this world, people are going to talk whether you actually do anything or not. You're going to need to decide if all this is worth it." A half-smile curls Blair's mouth. "And honestly, you might as well have some fun along the way."

Jenny seems to be taking this in with great concentration, but all she says is, "You look beautiful."

Blair rolls her eyes, releasing Jenny's hands so she can shrug out of the dress, letting it fall to the floor. "It's average. The color is last season and Stella McCartney has a much better version at Bergdorf's."

"Right…" Jenny says. "Bergdorf's." She dips to pick the dress up, gazing down at the fabric. Blair watches, as always.

"You know," Blair says, "If you like that dress, you can have it." Taken aback, Jenny looks at her. "I'm sure you'll find some way to repay me."

Jenny returns her attention to the dress for a brief minute before meeting Blair's eyes again. "Everybody does it?" she says. At Blair's solemn nod, she asks, "And it'll really help me with Nate?"

"Oh, Little J," Blair says, "Would I lie to you?"



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