Iceberg's Jewel pt. 1
This is just another idea rattling around in my head! While this is still yandere Batfam, the premise is slightly different—here, they haven’t quite met you yet. The focus starts with Oswald Cobblepot and the Iceberg Lounge, but trust me, the Batfamily won’t be far behind. Timeline-wise, this would technically come first, even though in my other yandere Batfam fics, Tim and Jason have already had their moments with you. So yes, there will be a plot hole later where they’ve somehow already hooked up with you—just roll with it. Consider it canon-ish, but mostly just me playing around with ideas. tl;dr: This is a prequel of sorts to my other yandere Batfam fics, but I’m mostly here to have fun with the concept. Hope you enjoy! 💙 word count: 3201
Oswald Cobblepot prided himself on running a tight ship. The Iceberg Lounge was a beacon of opulence in Gotham, catering to a clientele that wanted their danger with a side of champagne. When he put out that little “Help Wanted” sign as a joke—an amusing way to signal to the people he was looking for that he was ready to onboard—he hadn’t expected someone like you to waltz in.
You were nervous but bright-eyed, clutching a copy of your résumé (how quaint) in one hand, wearing a Gotham University sweater that screamed student loans and part-time hustle. The smile you gave him when he walked into the lounge floor was disarming—too genuine for this city. You asked to speak to someone about the janitorial position, and Os had to bite back a laugh.
“A janitor? Here? Sweetheart, you might be too good for this place,” he muttered under his breath, too quietly for you to hear, before waving a hand dismissively at one of his goons. “Send her to my office.”
His office wasn’t where interviews were usually held—far too personal, far too… revealing. But for some reason, he wanted to gauge you himself. Maybe it was your naivete; maybe it was the way your gaze lingered on the crystal chandeliers and plush carpets like you’d never seen luxury this close before. You were looking at him as a normal boss, not a criminal mastermind, and he realized he might like that.
By the time you’d been seated in the chair across from his polished mahogany desk for only 15 minutes, he was already hooked. He asked simple questions at first—your availability, your experience—but quickly veered into territory that let him know more about you. Your classes at Gotham U were interesting, but you worked too much to fully appreciate them. You loved your psychology major but struggled with scheduling, hoping that the pay here was more than the measly pay you scrounged from your other two jobs. He listened with great interest as you spoke of your genuine excitement to be working in a "classy place like this."
He didn’t have the heart to tell you this place wasn’t really classy—just good at pretending.
Cobblepot tilted his head, the curiosity in his expression sharpening as he tapped a finger against the arm of his chair. “You’re not from here, are you?” he asked, a sly grin forming. “So, what do you think of our little city?”
“Oh, uh…” You laughed nervously, shifting in your seat. “It’s… something, that’s for sure. Gotham’s kinda like… I don’t know, a scrappy mutt? It bites, like, a lot, but you can’t help but wanna pet it anyway. It’s scrappy and loveable.”
Oswald chuckled, the sound low and genuine. “Lovable?” he repeated, shaking his head. “You’re a strange one. Most people run for the hills when it comes to Gotham.”
“Yeah, well…” You shrugged, the faintest smile tugging at your lips. “I’m already here, so I might as well figure it out, y’know? Plus, it’s not all bad. I mean, the people are tough, and the city’s got… personality. A weird, messed-up personality, but still.”
He found himself appreciating your honesty. It was a rare thing in his world—people who weren’t either trying to butter him up or wring him dry. And that smile… Hm. Something about it didn’t belong here.
Then, the door to his office slammed open. A goon stumbled in without so much as a knock, huffing like a dog chasing its own tail as he fumbled a thick stack of papers in his hands.
Oswald snapped to attention so fast it was animalistic. One second, he was relaxed, bemused by you—the next, his face contorted with fury, his lips curling back in a snarl that made the dim office feel suddenly suffocating.
“What?” Cobblepot snarled, his tone cutting like ice. The very air in the room seemed to turn electric, humming with the promise of violence.
The goon froze mid-step, eyes darting between you and his boss. He looked like he’d just walked into an execution chamber by mistake.
Oswald’s teeth clenched so tight a vein throbbed visibly in his temple. “You knock before coming into my office,” he seethed, voice dropping to something far more dangerous than the initial explosion. Cold. Calculating. A blade slipping between ribs. “You wait. You don’t—”
Then, out of the corner of his eye, he saw you.
Frozen.
Wide-eyed.
And just like that, the change was immediate.
His snarl vanished. The storm passed in an instant, like flicking off a switch. The barely-contained rabid rage that had been twisting his face smoothed into something almost… embarrassed. Guiltily casual.
Cobblepot glanced back at you, then at the goon, then back at you. For a brief, telling second, he looked—not regretful, but calculating. Then he sighed through his nose, rolling his shoulders like he was shaking off an unpleasant thought.
"Handle it later," he ordered, voice abruptly warm. Silk-soft. As if he hadn’t just been inches from taking a man’s head off. His hand flicked lazily toward the door, a dismissive gesture. “Can’t you see I’m with someone?”
The goon scuttled out of the room like a kicked dog, the papers in his hands rustling violently as he clutched them to his chest.
The moment the door shut, Oswald let out a measured breath, as if centering himself. Then, in a whiplash-inducing shift, he turned back to you with an awkward, almost sheepish smile.
"Sorry about that,” he said, voice dripping with artificial sweetness, as if his outburst had never happened. He waved a hand, dismissing it entirely, his gaze keenly watching your expression for any lasting tension. “Some of my employees just don’t have any manners.”
You offered a polite, thin smile, still shaken, but brushed it off with a shrug. You had already figured this place wasn’t exactly warm and welcoming, but the speed at which his fury had vanished was... unsettling.
Oswald noticed.
He noticed everything.
And for the first time in a long, long while… he wasn’t sure if he liked the way your smile still had a hint of nerves clinging to it.
The Batcave was unusually quiet, save for the faint tapping of Tim’s keyboard and the low hum of the monitors. Bruce sat at the console, watching the live feed from Oswald Cobblepot’s office. You were seated across from the Penguin, a mixture of nerves and polite excitement etched on your face. The Iceberg Lounge’s chandelier lights reflected in your wide eyes as you gestured animatedly, your Gotham University sweater and résumé betraying your earnestness in a city that thrived on deception.
“Can’t decide if she’s brave or just clueless,” Tim remarked, leaning back slightly as he toggled between camera feeds. “She walked into Cobblepot’s lair with a résumé. A résumé, Bruce.”
“She’s a student trying to make ends meet. That’s not bravery—it’s necessity.”
Damian’s voice crackled through the comms. “She really responded to a ‘help wanted’ ad? Tt. Typical. Of course that bloated bird would choose a naive one. She’ll probably end up scrubbing vomit out of his VIP lounge carpets.”
Tim tutted thoughtfully at Damian’s comment. “I mean…..he’s probably aiming higher than janitorial work for her. Did you hear the way he sweetened his voice?”
Damian scoffed but didn't reply.
A new voice broke in over the comms—Dick, speaking from his position on patrol. “You think she knows what she’s getting into? Working there isn’t exactly safe.”
“She doesn’t,” Bruce answered simply, “But that doesn’t make her unique. Plenty of people stumble into Gotham’s underworld without realizing it. We can’t save everyone.”
Tim muttered, “Still doesn’t mean we should ignore it. If Penguin’s targeting her for something, we’ll want to know why.”
Damian chimed in again, his tone slightly mocking. “We already know why, Drake. He likes his toys naïve, optimistic, and disposable. She won’t last a week before she gets a reality check—or worse.”
Bruce’s eyes flicked toward the feed as Cobblepot stood, offering you a hand and gesturing toward the door. “They’re moving,” Bruce said. “Tim, keep the office feed rolling, and find another camera angle.”
“We won’t have audio and depending on where he’s taking her, I’m not sure we’ll have visuals either.”
There was a moment of silence, the kind that spoke volumes in the Batcave.
Dick broke it. “She’s smart enough to know what Cobblepot is, right? I mean, who walks into the Iceberg Lounge thinking it’s just a nightclub?”
“People who don’t know Gotham,” Tim replied, scrolling through files, soaking in what he can on you. “..She’s a psych major at Gotham U, full-time. She’s been juggling two jobs already, so she’s probably just desperate for the paycheck.”
Damian’s tone turned sharper. “Desperation or not, she’s still a fool. You don’t wear a sweater with your university’s name on it when you waltz into the lion’s den.”
Tim smirked. “Guess she didn’t take Gotham’s prerequisite: Street Smarts 101.”
The screen now displayed the empty office, Cobblepot’s desk abandoned. You were out of their sight, and for the moment, out of their reach. But the Batfamily wasn’t about to let you disappear into the darkness of Gotham without a trace. Tim was scrambling to find a feed that would give them info as to where Cobblepot’s taking you, but at the very least, they have relevant info on you.
Dick’s voice again. “Did you hear her in that interview? ‘Lovable but scrappy.’” He smiled faintly at the words. “She actually likes Gotham. We should keep it that way.”
Tim again, confirming some details. “Transferred to Gotham U from out of state. No criminal record, no red flags.”
Damian’s voice cut in, sharp and dry. “Other than walking into the Iceberg Lounge with a résumé. That’s a red flag for stupidity.”
Dick countered, his tone softer now. “She doesn’t know any better. Give her a break.”
Jason laughed, his voice snarky over the comms line from his own patrol. “Oh, sure, Grayson. Let’s all gather around and shield her from the big bad city. What’s next, care packages?”
Dick sighed audibly, “Don’t you have a crime boss to scare right now?”
Jason chuckled, the sound low and warm. “Already done. You should’ve seen the look on his face. Priceless.” Another faint noise came through, likely the reloading of a gun.
Bruce’s voice cut through before Dick could respond. “Enough. Focus, Jason.”
“Whatever you say, B,” Jason replied breezily, though the teasing lilt was still in his voice. “I’ll keep an eye out, too, just in case our scrappy little friend stirs up any trouble at the Iceberg.”
Damian snorted. “I’ll enjoy seeing Cobblepot’s face when she quits.”
Bruce didn’t respond right away. His eyes lingered on your face, captured mid-smile on the monitor. Quietly, he murmured, “She’ll need another job. A safe one. I’m sure Wayne Enterprises will have something available for her.”
“Keep me updated,” Batman ordered as he stood, his cape swishing as he headed toward the Batmobile. “If she gets in over her head, we’re pulling her out. No debates.”
Damian’s voice came back, quieter this time, reluctant. “She’s already in over her head.”
Little did they know, Oswald Cobblepot’s schemes for you were the furthest thing from exploitative labor. In his mind, the idea of you actually toiling away with a mop and bucket was quickly becoming unthinkable—borderline offensive, even.
The moment he saw the way your eyes sparkled with hope and determination, and saw the way you'd listed your good grades on your resume in a hopeful attempt at impressing him and proving your aptitudes, he’d decided he’d let you sleep on the job if you wanted to. Hell, he’d set up a whole suite in the back of the Lounge if it kept you close and content. You could waste time dusting the empty liquor shelves or filing nonexistent paperwork all day if it made you feel productive. What mattered to him wasn’t what you did—it was that you were here, where he could keep an eye on you.
But of course, Cobblepot wouldn't admit that to himself. Not yet, at least. No, this was just “good business,” he rationalized. You were a valuable asset—your charm and friendliness were enough to lighten up even the Iceberg’s darkest corners. You had a way of making the whole place feel... welcoming and warm, like you were untouched by Gotham’s grime and crime. Plus you wanted to be productive. He scoffed under his breath, amused. Of course one of the first fresh faces ready to work at the Lounge was also someone who he didn’t dream of involving in his actual operations. Just his luck.
So, if you decided you needed an afternoon nap in the dusty janitorial closet? He’d send a goon to bring you a pillow. If you scoured the cleaning supply catalog for hours without actually ordering anything? He’d find it endearing. As long as you were happy and oblivious to the underworld swirling just beneath the Lounge’s polished surface, you could do whatever you wanted.
Unbeknownst to them all, while they debated your safety, Oswald was sitting back in his office, already plotting ways to make your life easier. Sure, he’d keep up the charade of being your boss for now—keep you busy with harmless tasks so you didn’t get suspicious. But he wasn’t about to let you work too hard. Not his sweet, naive new hire.
You didn’t belong in Gotham’s shadows. And as far as Oswald Cobblepot was concerned, he’d make sure you never had to find out just how dark they could get. Or at least, he’d try.
By the time Oswald walked you to the janitorial closet—a tiny, forgotten room in the back of the lounge—he was already plotting how to keep you close. The closet was practically empty, a detail that normally wouldn’t bother him, but the way your face fell at the sight made him want to slap whoever was supposed to manage the damn place.
"Um… is this where I’m supposed to… work?" you asked softly, your voice unsure as you peeked into the empty closet. Your eyes darted around, taking in the barren shelves and dusty floor, as though you’d missed some hidden stash of supplies. "It just… doesn’t look ready yet?"
"Ah… this won’t do," he said quickly, covering his irritation with a smooth smile. "Looks like someone’s dropped the ball here. Don’t you worry about this, darlin’. I’ll get one of my guys on it—someone reliable. You’ll have everything you need to get started."
His tone was honeyed, and though he aimed for casual reassurance, his sharp eyes flickered to the shelves like he wanted to set the whole closet ablaze for offending you. For fuck’s sake.
“No, no, this won’t do at all,” Oswald said again, shaking his head and clucking his tongue like he was personally offended by the state of the janitorial closet. “You deserve better than this mess, darlin’. I’ll have it sorted by tomorrow, you have my word.”
You blinked at him, “If you want me on the job today, I can make something work,” you offered tentatively, gesturing toward the dusty shelves. “I’ve been in worse spots before.” You gave him a sheepish smile, trying to seem accommodating.
Cobblepot scoffed softly, waving a dismissive hand. “No, no, absolutely not. I won’t have my new employee starting off in such... subpar conditions. It’s a poor reflection on me, and I can’t have that, now can I?” He straightened his tie with an air of exaggerated importance before leaning on his cane. “Here’s what we’ll do instead. You take the night to get familiar with the Lounge—on the house, of course. Have some drinks, relax, mingle a bit. Consider it my way of welcoming you to the team.”
You blinked again, even more confused. “Oh, um, that’s really generous, but shouldn’t I, like… fill out some paperwork first? Or sign something?”
Oswald chuckled, a warm, low sound that almost made you feel silly for asking. “Paperwork? We’ll handle all that boring nonsense tomorrow. No need to rush into the dull parts of the job, eh?” He gestured toward the door, ushering you back into the main lounge. “For tonight, enjoy yourself. Swing by the bar, meet some of the staff, maybe say hello to the security team. It’s important to me that you feel comfortable at the Iceberg.”
You hesitated for a moment, unsure if this was some sort of test, but his expression was disarmingly sincere. “Well… if you’re sure…”
“Positive,” he interrupted, clapping a hand on your shoulder with surprising gentleness. “Now, off you go. The night’s young, and the Lounge is at your disposal.”
As you stepped out of the closet and back into the opulent main floor, you glanced over your shoulder to see him watching you with a smile that seemed too genuine for someone of his reputation. You didn’t know him, but you’d heard some things.
Unbeknownst to you, Cobblepot wasn’t just offering you free alcohol or a night to relax—he was staking his claim. He wanted you to feel at home, to see the Lounge as a safe haven, a place you’d always want to return to. Sure, there’d be paperwork eventually, but for now, the only thing that mattered was keeping you here, comfortable and unaware of the darker dealings hidden beneath the glamour.
Tim leaned back in his chair, toggling between the camera feeds inside the Iceberg Lounge. He was alone in the Batcave now, the others out on patrol in the city. “Well, there she is,” he muttered, zeroing in on his view of you at the bar. You were perched on a sleek barstool, your Gotham University sweater a stark contrast to the high-end fashion of the Lounge’s usual clientele. “She’s… drinking. A lot.”
Jason, freshly back from patrol—or what little of it he actually bothered to finish—sauntered into the Batcave, pulling off his helmet and setting it down with a thud. “That’s her?” he asked, nodding toward the screen.
“Yeah,” Tim replied without looking away. “You decided to show up?” His eyes flickered to the time down at the bottom of his monitor. "Thirty minutes early? B's not gonna be thrilled."
Jason ignored the jab, stepping closer to get a better look. “Huh,” he muttered, crossing his arms as his sharp eyes drank you in. You were laughing at something the bartender said, your cheeks flushed. You gestured animatedly with your glass while saying something they couldn't hear. “She doesn’t look like much.”
Tim raised an eyebrow, glancing up at Jason. “That’s what you cut patrol short for? To see her in person?”
Jason shrugged, his gaze fixed on you. “I was curious. Heard you and Damian going back and forth about her. Figured I’d check it out for myself.” His lips quirked into a faint smirk. “Didn’t expect her to be… this.”
Tim tilted his head. “This what?”
Jason gestured vaguely at the screen. “This… normal. Sweater, messy hair, drinking like she’s celebrating her midterms being over. Doesn’t scream ‘Iceberg Lounge material,’ y’know?”
Tim chuckled, toggling to another camera feed for a better angle. “That’s kind of the point. She thought she was interviewing for a janitorial position, Jason. Janitorial.”
Jason blinked, then snorted. “You’re kidding.”
“Wish I was,” Tim said, leaning back in his chair. “She walked in there with a résumé—an actual paper résumé—and asked about cleaning floors or whatever. Cobblepot probably laughed his ass off before offering her a drink.”
“He’s footing the bill by the way,” Tim added, toggling to a feed that showed the Penguin subtly watching you from across the room as he conversed with some guests. “She hasn’t reached for her wallet once. He’s just… letting her.”
Jason’s eyes narrowed as he studied the Penguin’s expression. There was no malice there yet, no obvious scheme in motion. Instead, Cobblepot looked almost… satisfied, like he was pleased with what he was seeing. “The hell’s his angle?” Jason muttered, his top lip curling in disgust at the possibilities.
“No idea,” Tim replied. “But if I had to guess? He’s trying to butter her up. Make her think the Lounge is a safe place, keep her happy and oblivious while he decides what to do with her.”
Jason scoffed, leaning back against the console.”She won’t last a week.”
Tim smirked. “You’re awfully invested for someone who just met her. Maybe you should prep a care package.”
“I didn’t meet her,” Jason shot back, though his eyes flicked back to the screen almost involuntarily. “I’m just saying, someone needs to give her a reality check before she gets eaten alive.”
“Maybe,” Tim said, watching as you swayed slightly to the music, chatting with another patron who’d joined you at the bar. “But she doesn’t look like she’s in danger. Yet.”
Jason grunted, pushing off the console and grabbing his helmet. “Yeah, well, I’m keeping an eye on this one. If Penguin tries anything, I’m ending it.”
Tim raised an eyebrow. “Oh, so now you’re helping? Didn’t you just skip the last half of your patrol?”
Jason smirked as he turned toward the exit. “Hey, monitoring Gotham’s underworld is part of the job, isn’t it? I’m just doing my part.”
Tim shook his head with a laugh as Jason disappeared up the stairs. “Sure you are.”
Back on the screen, you were oblivious to the scrutiny, to the way the curiosities of Gotham's vigilantes were beginning to blossom into something more.