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Not Your Average Cinderella Story

Summary:

Bruce nods. “It makes the most sense. You haven’t been made, you’re the right age, and your face isn’t known in that circle. We’ll fabricate a profile and ID. You’ll go during lunch, find Everett’s bag, get the drive, and extract quietly.”

Tim just stares at him. “You want me to go undercover… as a girl?”

Steph claps her hands, grinning ear to ear. “Best day of my life.”

Notes:

Yes, this started as a joke. Yes, it got wildly out of hand. No, I’m not sorry.

Hope you enjoy!

Chapter 1: If the Wig Fits, Cry in It

Chapter Text

The giant monitors hum softly in the low light of the cave, casting cold blue across the polished floor like a frozen spotlight. Tim’s seated at the far end of the table, hunched in his chair like a sleep deprived corpse. He feels like a dishrag that’s been rung out and left to dry over a keyboard and for once he wants sleep more than answers.

Everyone’s already here.

Dick perches on the upper railing with the effortless balance of someone who grew up in the air, one leg casually swinging, posture loose but alert. Jason leans against the table, arms crossed, jaw set, giving off a very clear I was dragged here and I hate it energy. Damian sits perfectly straight in his chair, hands folded in his lap, looking like discipline carved into a person. Duke is spinning himself slowly in one of the chairs, sneakers squeaking every time he twists back the other way. Stephanie stands beside him, chewing on a granola bar, and Cassandra is near the back, still and quiet, eyes sharp and unreadable.

Then Bruce speaks. “We have a trafficking ring operating in Westbridge Institute.”

Just like that, the room snaps to attention. All motion stills. 

Duke halts mid-spin, one foot dragging lightly against the floor. Dick’s leg stills. Jason uncrosses his arms just enough to look up. Stephanie freezes with her granola bar halfway to her mouth. Damian’s posture somehow gets even straighter. Cassandra’s gaze lifts to the screen. And Tim, despite the stiffness in his spine protesting like fire, forces himself upright.

The screen flicks to an aerial image of a school, ornate stone buildings, long courtyards, tall fences with padlocks. It looks more like a well funded prison rather than a school.

Bruce continues, his tone flat but edged with something grim. “They’re targeting vulnerable students. Girls with unstable home lives. Neglected. Forgotten.” He clicks again, bringing up a timeline of disappearance dates, each one a red mark that feels like a bruise. “They watch them, track their routines, their weak points. They confirm no one will notice until it’s too late. Then the victims disappear out of state under the label of ‘mentorship programs’ that don’t exist. The paperwork is fully falsified, transfers routed through shell organizations to bury any trail.”

Tim feels his stomach sink, slow and sickening, a cold slide that settles somewhere low in his gut. He knows this pattern. Knows the fear, the confusion, the way the world tilts when adults decide you’re expendable. The girls must be terrified. Alone. Trapped.

His throat feels tight.

Another click.

The screen shifts to a grainy still image, a man in his forties standing beside a dumpster, handing something small to someone half-hidden behind a cargo truck.

“This is Levi Everett, history teacher at Westbridge. Last week, he was observed transferring a drive to an associate of the Ruiz cartel. According to our source, it contains names, schedules, and vulnerability assessments of potential victims.”

Jason exhales sharply through his nose, “So what, you want us to go shake him down? Grab the drive?”

Bruce doesn’t even blink. “Not directly. He carries the original during school hours in his bag. If we tip him off, he’ll disappear and take the entire operation with him.”

“So a stealth op,” Dick says, leaning forward with that bright, easy confidence that makes everything sound manageable. “Got it. Who’s going in?”

Bruce doesn’t answer verbally. He simply taps a command and the holo-table lights up with a class roster, names, headshots, and uniform portraits.  Another click and a forged email chain opens beside it. Fake transcripts, transfer approvals, a carefully curated digital paper trail. Each document is the kind of thorough that means Bruce has been planning this for days.

“Westbridge is an all-female institution.”

A beat of silence.

Tim’s eye twitches. “…Okay,” he says slowly, carefully. “So, Steph? Or Cass?”

“Not possible.” Bruce says flatly.

Stephanie swallows her bite. “I was recognized near there two weeks ago, remember? That last bust.”

Cassandra nods once. “I’m compromised too.”

Dick frowns. “That leaves…”

“One of us,” Tim finishes flatly, dread sinking like a stone.

The room goes quiet, the boys exchanging wary glances like they’re silently playing an intense game of Not It.

Jason is the first to break. He lifts both hands, eyebrows raised. “Don’t look at me. I’m tattooed, I’ve been arrested, and unless that school’s running an extremely inclusive admissions policy, it’s not happening.”

Stephanie snorts. “Also, you walk like a brick in heels.”

“Thanks, Blondie.”

“Anytime.”

Dick shifts in his seat, shoulders squaring like he’s actually considering it. He lifts a tentative hand. “I mean, technically, I could maybe—”

“You’re six feet tall and built like a quarterback.” Tim cuts in, deadpan. “What, you gonna slouch into a junior class photo?”

Dick gives a helpless shrug. “I could try.”

Tim stares at him, flat and unimpressed. “You’re six foot.”

“Okay, fair,” Dick mutters, sitting back.

Duke raises a hand. “Okay, but seriously, do we have to send a girl? Couldn’t we fake a male staff member or something? Like a TA?”

Bruce shakes his head before he even finishes. “The school doesn’t hire male faculty under twenty-five. Strict policy. And they don’t accept male students at all. It has to be a girl.”

Another heavy pause.

Damian lifts his chin. “It will not be me.”

“God, no,” Dick says immediately. “You’re thirteen, Damian.”

Jason snorts, leaning back in his chair with a wicked grin. “What about B? I’d pay good money to see Bruce in a wig.”

Bruce doesn’t even bother looking up from the console. “No.”

“Coward.”

Then, slowly, all eyes swivel to Tim.

He blinks. “No.”

Stephanie’s eyes are already lighting up like she just unwrapped a brand-new grappling hook for Christmas. “Come on. You’re the perfect height.”

“Soft features.” Cassandra adds calmly.

“You already look like a haunted Victorian orphan,” Duke adds, grinning like he’s helping.

Tim turns toward him, incredulous. “That’s not even a compliment.”

“Sure it is,” Dick says cheerfully, clapping him on the shoulder. “You blend in like a pro. Quiet, observant, weird in social settings. Total high school girl material.”

Tim stares at him, jaw tight. “Wow. Thanks.”

Bruce nods. “It makes the most sense. You haven’t been made, you’re the right age, and your face isn’t known in that circle. We’ll fabricate a profile and ID. You’ll go during lunch, find Everett’s bag, get the drive, and extract quietly.”

Tim just stares at him. “You want me to go undercover… as a girl?”

Stephanie claps her hands, grinning ear to ear. “Best day of my life.”

Bruce continues on like this is a perfectly reasonable Tuesday. “Cass and Steph will handle your cover identity. Dick will be the distraction. Jason is back up and evac. Barbara will run surveillance. Damian and Duke stay in the cave on comms.”

Jason perks up, smirk spreading like a bad idea taking root. “Can I pick the outfit?”

“Absolutely not.” Tim snaps.

Stephanie is already swiping across her tablet like she’s designing a superhero suit. “You’ll be Morgan Clarke.” she announces with terrifying enthusiasm. “Your dad’s an international businessman. Your mom’s in Milan designing handbags. You just transferred from a French boarding school.”

Tim squints at her. “Why France–?”

“Because it’s classy, plus you can speak French,” she says with a grin. “Now shut up and let me figure out your wig size.”

Tim drops his face into his hands with a low, muffled groan.

Cassandra leans over to peer at him, her expression soft, which from Cass is practically a motivational speech. “You’ll be pretty,” she says gently, giving his shoulder a small pat.

Tim lifts his head just enough to stare despairingly at the floor. “I hate this mission.”

Damian folds his arms, voice dry as sandpaper. “Try not to embarrass the family name, Drake.”

Tim exhales a long resigned breath, the kind that says he’s accepted his fate but will complain about it every step of the way. He’s absolutely going to regret this.

__________________

The next morning is, without exaggeration, hell.

Tim got maybe three hours of sleep, and that’s being generous. Two of those were spent half-heartedly pacing his room, trying to walk in a straight line without looking like a malfunctioning Roomba, and trying to figure out how to pitch his voice higher to mimic a teenage girl’s. 

And now he’s awake at 5 A.M. in Stephanie’s room, seated stiffly in a chair that smells vaguely of nail polish remover and vanilla body spray, while she yanks his soul out through his scalp.

“Sit still or I’m using zip ties.” Stephanie warns, voice chipper and evil as she tightens the wig straps at the nape of his neck.

Tim winces. “That’s not an idle threat, is it?”

“Not even a little.” She twists a section of black hair that’s shiny and unnaturally soft, curled at the ends like something from a shampoo commercial, before stabbing it in place with a bobby pin.

Tim glares into the mirror, watching in real time as his reflection transitions from sleep-deprived cryptid to transfer student from France whose parents own an art gallery.

Stephanie leans in, squinting one eye like an artist lining up a stroke. “You squirm more than Jason during an ethics lecture,” she mutters, tucking another coil of hair neatly behind his ear.

“That’s because you’re stabbing my brainstem.” Tim complains, gripping the chair arms. “I’m gonna have permanent nerve damage from this.”

Cassandra, perched silently on the dresser, rummages through Stephanie’s makeup bag, sifting through dozens of brushes and palettes. She lifts one out, holding it between two fingers. “Mascara or lashes?” she asks calmly.

“Neither,” Tim groans. “Isn’t the wig and the uniform enough?”

“You’re infiltrating an all-girls school,” Stephanie says without looking up. “You’ll stand out more if you don’t wear makeup. Besides, your bone structure is cheating. I barely have to contour.”

Tim scowls at his reflection. The worst part is they’re right. His face looks… passable. Soft angles. Big eyes. High cheekbones. It's unsettling how little effort it takes.

“I look like I should be writing poetry in a café about how no one understands me.”

Stephanie snorts, securing another bobby pin. “Honestly? You kinda do.”

Jason walks by the open door and immediately doubles back, eyes wide. “Oh my god. Is that Tim?”

Tim points at him without breaking eye contact through the mirror. “Out.”

Jason leans on the doorframe, arms crossed, grinning like a hyena. “You look like you’re about to start a Gossip Girl reboot.”

“Leave,” Tim says flatly. “Before I add fratricide to my to-do list.”

Cassandra tilts Tim’s chin upward, unfazed. “Lip tint.”

“I swear to God,” Tim mutters. But he stays still. Mostly. She taps on a subtle cherry shade, almost delicate. Almost pretty.

Dick’s laugh echoes faintly from down the hall.

“Was that—was that Dick?” Tim demands, twisting in his chair.

Stephanie spins him back around with both hands. “Focus, Morgan.”

Tim groans and drops his head into his hands. His nail polish is light pink. When did they do that?

An hour later, he stands in front of the full-length mirror in Stephanie’s room, arms limp at his sides. The outfit is… thorough.

The plaid skirt hits just above the knee, crisp pleats swaying every time he shifts. The white blouse is tucked in with military precision, its collar brushing lightly against his neck like it’s mocking him. The navy cardigan is buttoned only halfway, because Stephanie said it made him look “effortlessly studious.”

The knee-high socks cling to him a little too comfortably, shiny black loafers squeaking faintly when he shifts his weight, because of course they do. The wig falls in soft waves past his shoulders, the fibers expensive and unnervingly realistic, brushing against his jaw every time he turns.

The glasses sit delicately on his nose, non-prescription, but fitted with a miniature. His skin looks even. Actually even. No dark circles haunting his eyes or stress lines around his brows. His lips are lightly tinted pink, lashes curled in gentle swoops. His face looks… soft.

He stares at himself like he’s trying to recognize a stranger in his own face.

The silence stretches long.

“This is hell,” is all Tim can say.

Stephanie grins behind him. “You say that now.”

“No,” Tim says hollowly, turning just enough to see her over his shoulder. “I mean it. Actual hell. Dante missed a circle and it’s this.”

Behind him, Duke makes an awful strangled sound, half cough, half suppressed laughter. “No, no, it’s… it’s nice. You look great. Really.” He’s trying to be supportive, but his eyes have that glassy, I can’t believe what I’m seeing shine.

Tim doesn’t even blink. “I’m so glad my suffering is visually pleasing for everyone.”

He tugs awkwardly at the edge of the skirt again, as if a few more centimeters of fabric will save him. The mirror doesn’t budge. He still looks like the sleep-deprived ghost of a private school honor student with unresolved trauma and perfect mascara.

Jason laughs, short and loud. “I can’t believe this is real. You look good, Timmy.”

“Please shut up.” Tim groans, deadpan.

“No, seriously,” Jason continues, still grinning like he’s watching the best sitcom of his life. “If this weren’t an all-girls school, some poor kid would’ve written a love poem about you by fourth period and passed out trying to confess.”

“Yeah. Super glad,” Tim mutters. “Truly. Peak life moment.”

Dick claps once, too cheerful. “Alright, walk test.”

Tim sighs and takes a few hesitant steps, wobbling slightly in the flats.

“I hate heels.” Tim mumbles, wobbling forward.

“They’re not heels, they’re flats.” Stephanie corrects, arms crossed.

“They feel like heels.”

Cassandra watches him walk, arms folded like a drill sergeant mid-assessment. “Loosen your arms. Smaller steps.”

Tim tries again, shoulders back, chin up, like he practiced last night while rethinking every life choice that led to this moment.

“Now smile,” Dick says, nodding encouragingly. “You’re the new kid. Try to look approachable, maybe even not like you’ve been trapped in a costume drama nightmare.”

Tim tries. The smile in the mirror looks like something a cashier gives when they’re about to quit.

“You look stiff,” Damian pipes up from the corner.

“Yeah, I can tell believe it or not.”

“Whatever,” Stephanie waves him off. “It’s passable. Voice test now. Let’s hear your ‘Morgan.’”

Tim exhales like he’s deflating. He clears his throat, shifts gears, and speaks, soft and careful, pitching slightly higher than normal but not exaggerated, “Hi, I’m Morgan Clarke. I just transferred in. Could you point me to the main office?”

Silence.

Stephanie blinks, eyes wide. “Oh my god.”

Duke tilts slightly in his chair, arms crossed over his chest. “Okay… that was… kind of scary.”

Jason stares at him like he just turned into a ghost. “Jesus. Talk about freaky.”

Cassandra nods thoughtfully. “You’ll blend.”

Tim’s face flattens, deadpan. “Awesome. Now can we please stop looking at me like I’m a lab experiment?”

“Sorry,” Stephanie says, “You’re just… aggressively passable. It’s actually unsettling.”

Tim drops his head into his hands again. “Is that a bad thing?”

“Not really,” Jason says, still squinting at him. “It’s just weird knowing the person behind that wig and lip gloss once drank six Red Bulls in one setting and hacked the Pentagon just to see if he could.”

Tim groans. “Can we please return to the part where this is a trafficking ring op and not an episode of America’s Next Top Tim?”

“Not until we get pictures,” Jason lifts his phone. “Okay, say cheese–”

“If you take one photo,” Tim says without looking up, “I will break your phone and your kneecaps in the same throw.”

Jason raises his hands. “Jesus. You sound like the demon brat.”

“I will pretend you didn’t say that, Todd.”

A throat clears from the doorway.

Bruce enters the room, calm and composed like this is any other Tuesday briefing. “Everyone. Focus. Tim, your cover is solid. ID and school records are in your bag. I’m sure you’ve memorized your schedule, but there’s a printout just in case. Blend in. Observe. Make contact at lunch. If anything feels off—”

“I run. Yeah. Got it.”

Stephanie pulls him gently aside, all snark fading from her face. “Hey,” she says quietly. “You’re gonna be okay. Just one day. In and out and we’ll be on the comms the entire time. You’ve got this.”

Tim nods once, stiffly. His reflection still stares back, foreign and unblinking. Cassandra steps closer, straightening the collar of his cardigan, then presses something small into his hand. It’s a tiny, matte-black keychain canister. He doesn’t need to ask.

“In case anyone gets… weird,” she says, just loud enough for him to hear.

Tim closes his fingers around it. The weight is small but grounding. “Thanks.”

It’s the only weapon he’s allowed to carry, anything more could blow his cover. But having something is enough.

Cass nods. “You’ll be fine.”

He nods back, then exhales through his nose. Pulls himself up. Shoulders straight, smile soft. Approachable. Friendly. Fake.

“Alright,” Bruce says from behind them. “Alfred will take you to Westbridge. Class begins at 8:30.”

Tim glances one last time at the mirror. He’s Morgan Clarke now, a high school girl who transferred from France. He turns, grabs his bag, and walks out.

“Knock ’em dead, Timbo.” Jason calls behind him.

Tim flips him off without looking.