Title: Games that Never Amount to More than They're Meant Will Play Themselves Out (or Five Times Jenny Humphrey Kisses Chuck Bass)
Character/Pairing: Chuck/Jenny
Summary: His mouth tastes like a promise and his tongue feels like an oath.
Rating: PG-13
Word Count: 2,200
Disclaimer: I own nothing. Title from Falling Slowly by Glen Hansard.


The first time Jenny kisses Chuck, it's more like he kisses her.

Jenny thinks it's kind of nice, a little sweet and soft. His lips pressed precariously against hers, his palm warm in her hand. And still, there's something dangerous about the entire thing. He's Chuck Bass; she's just Jenny. Her heart quickens and lumps itself in her throat. She concentrates on breathing steadily.

And then it's not so nice.

It's too much. His body leaning into hers is crushing and intimidating. His hands are rough and pushing and she tries to shove him off, to make him stop. She can't. She's too weak. Her lungs are gasping and her heart is in overdrive and she's trying to think of ways out of it. Trying to make any bargain she can.

When Dan comes and rescues her, she feels guilty.

Like she ruined his night.

Like she should have been stronger than that, instead of playing the damsel in distress who doesn't even get rescued by a prince, but by her brother. She should have been smarter, realized that he was Chuck Bass and she was just Jenny.

She thinks it's the biggest mistake she'll ever make.

(Later, she can't believe how wrong she is.)


The second time she kisses Chuck, it's more like they're kissing each other.

She can taste the alcohol on his lips, can decipher how it's the expensive kind and not some cheap scotch you pick up at the drugstore. It doesn't mean her standards have risen. She can sense how lost he is, the loneliness in the way his hand skims her arm, goosebumps rising in the wake of his fingertips.

She feels lost, too. Completely alone.

Maybe that's why she does it (maybe that's only part of the reason).

They stumble to his bedroom, hands roaming everywhere, except this time Jenny feels like his equal, like she has regained some of the power she gave up to him on the roof. They stop, step apart, stare at each other until their breathing is normal, until they feel calm.

It makes the decision seem rational. It's not.

When he strips off her shirt, she shivers. He sighs into her neck, his breath hot and dry. Jenny bites her lip, grinds her hips down into his. Sex is exactly how she expected it, and nothing like how she imagined it would be, too. A contradiction. He's cautious, careful, and slow with her. Chuck's eyes lock with hers every few minutes, asking her if she's okay, if she wants to keep going; they plead for her to say yes.

She does.

After it's over, she feels empty. She feels like a cliché.

But she doesn't regret it. Jenny knows guilt won't get her anywhere, won't change anything.

When Chuck offers her the chance to stay, she feels sick. He jokes that not everybody gets that offer, but it doesn't sound funny when the sound hits the air and travels to her eardrum, and Jenny knows he's not laughing either. She wonders if he feels the same way she does. She hopes he doesn't, for her sake.

She tries to pretend she was more than just a lonely fuck for him. Because he'll always be her first.

She knows she wasn't. She's expendable, always is.

Blair comes over; Chuck rushes to her. Jenny can make out their silhouettes through the glass, hears Chuck's lies. It hurts her more than she'll ever admit to anyone. She quickly and quietly makes her exit-the way she knows he'd want her to. He doesn't even notice.

She regrets it now, even though she tries not to.


The third time she kisses Chuck that's exactly what it is. She kisses him and he pulls back, staring at her with unusual amounts of concern pooling in his eyes.

"Jenny," he begins, sighing quietly and reaching for the scarf he discarded on the coffee table.

"Please, don't." Her voice cracks. She stands up and walks behind the couch, the soft click of her heels echoing like a clock ticking, counting down the moments until her inevitable destruction.

(She doesn't forget how she self-destructed years ago. It's a pattern that repeats; she can't stop it now matter how much she tries. She gives up.)

"Jenny," Chuck repeats, forgetting the scarf and walking over to her instead. His eyes are pitying, and she never thought the day would come when Chuck Bass would be pitying her this way. In her head, it was always the other way around. "You don't want this."

"What if I do." It's a challenge. One he started years ago on a roof and one she continued at a masquerade ball.

(He stopped playing long ago, but Jenny still moves her piece around the board, waiting for more. One of these days, she tells herself, she'll win. She's been deceived into thinking she has before. She hasn't.)

He reaches out and grabs her wrist, but lets go almost instantly, as though the touch burns him. His eyes aren't as dark as she remembers, but his voice is rougher, like he's been smoking Cuban cigars daily. "Trust me."

"Never." It's the one promise she's never broken since she left Manhattan.

(Jenny thinks that has to mean something-everything.)

Chuck leans over, allows his lips to brush her cheek, murmurs that she's better than this. He leaves, running his scarf through his fingers and shutting her door hard, the thud reverberating around her apartment and through her skull, like he's trying to send a message, plant an idea in her head and shake her out of it-whatever he thinks it is.

(And whatever it is, it's his fault.)

Instead she pours herself a glass of scotch, the same kind she drank that night (It's the only kind she drinks), and falls asleep on her couch, walking up with mascara stains running down her cheeks, pieces of blonde hair sticking to her sweaty forehead.

She decides she hates him.


The fourth time Jenny kisses Chuck, she doesn't really kiss him.

She's in some club, the air stale and bodies knocking into her, threatening to knock her over. Some disgusting man squeezes her ass and she flicks him off. The sense of power it gives her is small, nothing like it used to be. Rebellion isn't a rush, but a lifestyle.

(It breeds pain and emptiness, but Jenny doesn't dwell on that, can't dwell on that.)

When she sits down on a bar stool, she isn't surprised to see Chuck already there. He does own the place. His eyes are empty, pupils wide and unfocused. She read about Blair marrying the Count of something or other on page six a few months back. She feels a little bad for him, but it's a form of revenge, too. (A kind she hadn't even thought up in the days when a voodoo doll seemed like a viable option.)

He gets to hurt in the same way he hurt her.

(She let him hurt her. But that doesn't factor into the equation. He should have known better.)

"Hello, stranger." The words sound more confident than she feels.

His head turns languidly, hair falling over his forehead and into his eyes. Chuck blinks at her a few times, as if trying to discern if she's real or not-or perhaps she's simply blurry. "Humphrey," he finally slurs.

A perverse pleasure tickles up her spine and she smiles, red lips cracking. "Bass."

"What're you doing here?" he asks, turning back to his empty shot glass and running his finger around the rim. There's something so pathetic about him in this moment that makes her understand him, just like before. They're cut from the same cloth: failures.

"Giving you business." It's a joke, so he laughs deprecatingly because he's drunk. Jenny feels something inside her shift. She's not angry anymore, but the bruise is still there, painful and dark.

(She can't help but blame him, still. But she knows it's her fault, too. Her life is her doing, and his life is his.)

"Let's get out of here," he whispers, looking into her eyes. She's surprised by the sincerity in his irises, the slight tilt of his chin.

She wraps her fingers around his bicep, helps him up off his stool and drags him out of the smoke and the heat. It'd be too easy, she knows. There's a reluctance in the creases on his forehead, but he'd give into her if she asked. If she leaned against the brick wall and ran her fingers through his hair, he'd respond, he'd whisper pretty lies into her ear.

She's wanted that for so long from somebody, from anybody (but really, from him. Because he was her first, and no matter how much she tries to deny it, that means everything to her, even if it means nothing to him). But suddenly she doesn't want that at all.

Jenny takes him back to her apartment, lays him on his side and carefully removes his designer shoes, laying them at the edge of the bed. She pulls the covers up and climbs in next to him, his body heat hitting her in waves, his smell pungent, almost revolting.

Chuck runs his hand over her cheek. "I'm sorry," he murmurs, eyes halfway closed.

"For what?" She holds her breath.

"You were different." His eyes drift shut and his hand falls from her face. "I'm sorry," he whispers.

Jenny leans over, presses her lips softly to his forehead. Tears pour from her eyes as she watches him sleep, his chest rising and falling steadily. She thinks about how she should have been able to watch him sleep that night years ago. How instead she cried by herself and heard she meant nothing, his words to Blair echoing over and over in her skull until they broke into blurry syllables.

She left hoping to find a different kind of life, one with a clean slate. A guy who was better, who could erase the cracks in her heart.

(Prince Charming isn't supposed to be this way, she thinks.)


The fifth time she kisses Chuck, he buys her dinner first.

He's a perfect gentleman, well, not perfect, but close. He opens the limo door for her and tells her she's beautiful and smiles gently. He doesn't mention past mistakes and past regrets; they feel a lifetime away, but like if she turns around too quickly, they'll creep up on her and she'll be back where she started. Broken and fragile.

Inviting him inside is something she planned when he first called her, inviting her to dinner. She played the scenario in her head: rejection, acceptance, push and pull. It's not until he closes the door and she's poured the scotch that Jenny realizes she doesn't know what comes next.

She takes a small sip of her drink and settles down on the couch, glancing sideways at him. It's suddenly all too familiar. Her heart beats achingly against her ribs. Maybe, Jenny thinks, this her chance to right a wrong.

"Why are you doing this?" she asks, tucking a piece of hair behind her ear.

Chuck pauses, sets his glass down and exhales slowly, shifting to look at her. The silence is eating at Jenny, she wants to fill it, but she holds back, knowing it's the only way she'll get her answer. "I need you."

Her eyebrows shoot up. A smile pricks at her lips despite herself. "What are you talking about?"

"Jenny," he repeats her name like a prayer.

"Chuck." She shifts closer, placing her own glass next to his, eyes unblinking. All the differences of this moment wash over her, and it's okay. It's more than okay.

When his lips crash into hers it doesn't feel wrong like it always has before. They don't speak of loneliness or lost love or struggling to gain control, to be people besides themselves.

His mouth tastes like a promise and his tongue feels like an oath. She stopped wanting a long time ago; she needs this.

Her head spins and past stories are rewritten. Tailored to suit the here and the now, the way Chuck presses lightly on her pulse, the blood pounding through her wrist.

It's a night she won't regret; the beginning of something she forgot existed when she was sixteen.

(She finds her own version of Prince Charming—twisted as it is.)

( Jenny forgives herself.)