#yandere Oswald cobblepot

[myerssimp21]

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.

[yandere--stuck]

Is it possible to make a request headcanons for Yandere BTAS Oswald Cobblepot?(ﾉ´ヮ`)ﾉ*: ･ﾟ

🐧 Oswald Chesterfield Cobblepot is, above all things, a man with impeccable taste. It's only natural that he'd set his sights on you. A vision of pure enchantment. Divinity in human form. A marble sculpture made flesh, allowing unworthy, mortal eyes to bask in your grace. As a collector of fine art, Oswald knew he had to have you. In a room full of art, he'd only desire to steal you.

☂️ Using the wealth, power, and connections he's accrued over his criminal career, Oswald is easily able to gain information on you. He sends out some of his underlings to keep watch over you, keep track of your routine, and relay any and all findings on you back to him. Such knowledge is key to the courtship process, after all. What kind of suitor would he be if he knew nothing of his lovebird?

🐧 Oswald will likely incorporate a mixture of both his and your interests into future thefts in an attempt to catch your eye. If you have a favorite artist, news coverage will suddenly report that The Penguin has also developed an interest in plundering their work. You may or may not find your favorite prices suddenly displayed in your home. When he finally reveals himself to you, he aims to spoil you even more. The finest of garments, quality cooking, luxury furnishings… In fact, why stay anywhere else but his manor? You deserve nothing but the best, the perfect home, and… Well, Oswald has so many, big empty rooms…

☂️ Oswald also makes sure to inform his fellow Rogues that you are completely off-limits with regards to any crimes they may commit, even if only incidentally. He wants you safe and sound, and will not allow you to fall victim to criminal activity because of the life he's chosen.

🐧 Oswald is able to convince himself that any of your refutations on the nature of your relationship can be waved away as shyness or insecurity on your part. As such, he wants nothing more than to reassure you that you deserve all the love he has to offer. And, with him being rather affectionate, he typically uses touch to prove this to you. Being a gentleman, Oswald loves bestowing kisses upon your hand or cheek when in public. He'll also whisper sweet nothings into your ear in hopes of making you flustered. In a more private environment, he's especially fond of cuddling, and may even try to preen you if he gets caught up in the moment.

☂️ He's semi-lucid in terms of his awareness that you may not return his feelings. It's a constant creeping feeling at the back of his mind left behind by Ms. Vreeland and her cohorts. However, Oswald is able to quell these concerns with the excuse that you only act so hesitant to be with him due to concerns with the law. It makes sense, doesn't it? You wouldn't want to appear complicit in any of Oswald's criminal activities lest you also be punished by Gotham's joke of a justice system. In fact, Oswald wouldn't have it any other way. The only thing that matters to him is your safety and happiness. But, he doesn't dare ask if it truly is the case. He doesn't want to ruin this for himself, just in case. He doesn't want to shatter the illusion. He just wants to be happy and to make you happy and for you to love him as much as he does you. Just let him have this, please.

[cyanide-and-roses]

Yooo you write for TNBA Penguin? I need more yan headcanons of him ngl, can I pls have some more? 👀

More Yandere TNBA Oswald Cobblepot headcanons

Sorry it took me a while to get to this! Christmas time is pretty busy lol. Exams may be done but there's Christmas shopping and family gatherings. I'll still do my best to get to every request as soon as I can! (CW: manipulative behavior, stalking, unhealthy relationships.)

Oswald is used to keeping up a facade. It's how he avoids getting into trouble with the authorities. This means he's really good at ensuring you never catch on to his less than savoury actions.

He's hired some people who are savvier with cybersecurity than he is to hack into your online accounts to monitor your online activity, especially your online shopping, so that he knows what gifts to get for you.

He's hired some people who are stealthier than him to follow you throughout the day, just to learn what your schedule is, and to make sure nobody is giving his darling any trouble.

He hires other people to do the work for him, just so you'd never figure out it's him who's been watching you.

If you get an inkling of a feeling that something fishy is going on, then he's immediately going to start love bombing you. Expensive gifts, expensive dinner dates, he'll start throwing money around if it means it will distract you.

If that doesn't work, then it's gaslighting time! He's scarily good at it. Instead of just straight out calling you crazy, he'll act concerned.

He's willing to make you question your own sanity if it means keeping you in the dark about his criminal activity and how possessive he is about you. He'd rather make you think you're insane if it means you won't leave him. He wants to figuratively keep you in a little cage, like one of his birds. He can't have you flying free, now can he?

[helpfandom]

May I request BTAS Oswald Cobblepot with a platonic darling who’s form of affection is gift giving and physical affection. Sometimes they’d give him little gifts and trinkets they’d find and occasionally give him hugs and cuddles

Broski. Let the anons have a turn. This is your 5th request. [That I am aware of]. /j

Not much changes from his actual Yandere personality.

Most of what changes is that he becomes so much more quicker to kidnap for a Darling that does 'pebbling' [something that Penguins do].

For such an affectionate Darling, it is reasonable to assume that that is also the type of Darling that is willing and okay for him to assume a role as a father.

He would enjoy any and all things that you give him, cherishing them. Even if they were worth a lot of money, he would never sell or get rid of the things that his kid gave him, especially from such a willing kiddo.

[stabby-apologist]

The Penguin and the Riddler run the Underworld as business and romantic partners. During their reign of Gotham, they've "yandered" a masochistic sub who will do anything they ask, as long as they keep her "urges" in check. Considering how the city has went through catastrophe after catastrophe in the last 5 years, they can agree on one thing: "A party is not a party without entertainment, and the party never has to end if the entertainment never leaves."

[yanderemystic]

⋆˚࿔ৎ⪩ Yandere Oswald Cobb Headcanons

— Oswalds traits: Manipulative, clingy, impulsive.

Oswald is pretty clear with his intentions. If he wants it, regardless of the so-called value, he’s going to get it somehow and someway. That comes with the same price as you.

Impression is always his go-to. With that and his high interest, these two combined can become quite a mess. He tries greatly to reel you in with his wooing—using every romantic strategy he knows from his heart to get your attention. He goes all the way to town, like gifting you very expensive items to hint that he can care for you. Giving you a few thousand when dropping you off at your apartment, or even offering to pay for it.

His favorite thing is taking you out to nice restaurants in Gotham, showing you off with your gleaming outfits that he’s gifted you himself. He’s a known gentleman, always putting your necklaces or rings on–even earrings if you want him to. Everything you could want is gifted from him.

Apologetically pushy. From the moment he’s met you, he's always wanted to be in your personal space. Calling you constantly. Always finding excuses to visit your apartment, even at late nights, showing up with takeout and shoving himself through the door before you can fully open it; that glimmering smirk of his, as he rambles and calls you his sweet doll.

Oz doesn’t mean too, truly, but he’s gotta know every detail in your life—admiring those picture frames you have, to the specific color you use, maybe makeup or even your own bedroom which you have decorated to express what you like. Maybe, if he finds a diary, if he is lucky enough, he knows damn well it’s coming with him. He can always say he found it. Pretended to never read it, right?

Your parents will most definitely approve of him. It’s a dream come true, a gentleman in this century? What a lucky dream. Though, if your relationship isn’t as strong as between him and his ma, he’s always willing to share her with you. Share sweet memories, even.

With each piece of newfound information with you, he really begins to get nosy with you. He doesn’t mean to press his nose into where it doesn’t belong, but he has to know what you are doing. To know what restaurant you are at with some friends, what times you get home, who you were hanging out with, and when you left. If you hide something from him, he will know about it.

A worry freak. If you don’t message him back within a few hours, he begins to panic. Watches your conversations like a hawk, waiting for the bubble to rise. If he doesn’t see it, he rushes to your apartment like a mad man. When all is good, and you are fine, he gets irritated—why can’t you just message him back with ‘i love you too’?

He makes it clear that he is obsessed with you—his hands keep near you like second skin. If you decide to go with him to the club, or to a nice place where there are a lot of people, he’d love for you to sit on his lap. A hand on your waist, squeezing every once a while. His pinky accidentally swiping over your thigh. His lips chasing down your shoulders, kissing your revealed skin.

I had such fun writing this. Please enjoy it as much as I did! Requests are open so please come and send em in •‿• !!

[yandere-wishes]

I'm currently obsessed with Gotham, everyone is so hot and broken, literally my type. Would you guys like some general HC for the characters? I'll probably write it when

[lonleywriters-blog]

How would Yandere Gotham villains react to their darling trying to run away?

Ofc darling

Yan. Gotham villains react to escape attempt

Delusional all the way

You are just running around like the white rabbit

You are just exploring

You love him

You would never leave

He just hugs you and drags you back home

He will lay down and cuddle for a while

Maybe have some tea

You never get punished

Laughs hysterically

He makes a big joke with gestures

He will then stare you down

He will be pissy

But he is petty

He will drag you back

Silent treatment

Doesn't feed you or give you attention

Caves in after a week or so

Very sturn

He will command you to come to him

Drags you back and lectures you

Locks you in your room for the rest of the day/night

Makes you say sorry

Has a bonding day with you

Sturn but gentle lectures

He is angry, devastated, and giddy at the same time

How dare you leave him

What did he do wrong, he's sorry

Ohhh you are so in for it

He will pick you up and carry you home

Locks you up with no bed arms chained and no food

He may inflict pain if you pushed it far

Let's you out after three days

Gentle loving aftercare

It hurts him

He is a bit sadistic though

He will cry to you

He will tie you up to a chair

He will lecture you

Then he will play a riddle game

If you get one wrong he hits you with a ruler

If you get them all right he will be all lovey dovey

He's gentle after

She is so bitchy

She will be dramatic and mock you

Pull you by the hair

She will lock you in her bedroom

Brushes your hair kinda rough

Gives you tough love

Threatens you

Passive aggressive

Very clingy

So spoiled

She will gently pick you up to restrain you

She strokes your hair

Blames it on her not giving you enough attention

Spends so much time with you

Gives you skin care and a makeover

Starts spoiling you more

Buys you more things

[gothamitelove]

Oooh, you are taking requests? May I request BTAS Oswald Cobblepot yandere headcanons if you haven't done something similar already? Thank you!

YES PENGUIN LOVERS FTW

yandere!btas!oswald cobblepot headcanons

one thing i love about this oswald is that he is NOT a shy dude. he's forward, he's blunt, and he goes after what he wants. damn the consequences.

you are no exception to this rule. he sees you and it clicks immediately. he's not a big believer in god or fate, but he knows somehow that this is a meant to be thing.

his first move's gonna be charming your fuckin socks off. he's buying you dinner, he's complimenting you- he wants to give you everything you want

he is also going to watch you like a hawk.

do not be surprised if you have bodyguards. don't be surprised if you find cameras in your apartment. don't be surprised if oswald name-drops someone in your life that you haven't told him about. he already knows.

in all honesty he probably has a file on you, or something equally crazy

he wants to know everything about the people in your life. when you bring someone up, he's got questions- who are they? where'd you meet them? how'd you meet them?

and then he does his own independent research, because they could be manipulating you! and what kind of partner would he be if he knowingly let you open yourself up to people who would hurt you?

his need to keep tabs on you doesn't stem from insecurity, it stems from protectiveness

if someone tries to make a move on you, they probably won't be seen again. oswald's got people to break legs for that

[yanderejustforyou]

Other Plans

Summary:

“You think you can just walk away, don’t you?” Oswald whispered, his lips brushing tantalizingly close to Victor’s cheek, as if sharing a secret meant only for the two of them.   I do request!!!

The Iceberg Lounge was bathed in low, flickering candlelight, casting long shadows that danced across the opulent room. Rich mahogany furniture gleamed against the muted hues of the walls, and the bar was lined with an impressive array of spirits, tempting anyone who dared to venture closer. Oswald Cobblepot stood near the bar, his fingers gracefully tracing the rim of a crystal glass filled with a deep amber liquid as he surveyed the empty room, a flicker of something unreadable in his dark gaze. It was late—late enough that the usual patrons had long since retreated into the night, leaving only the echoes of their raucous laughter and flirtatious whispers to linger in the air like a distant memory.

But it wasn’t the quiet that held Oswald’s attention captive. No, it was Victor.

Victor Aguilar had been distant lately, a silent defiance quietly brooding in the depths of the younger man’s eyes each time their gazes intersected. It was in the subtle, almost imperceptible way he sidestepped Oswald’s once-unchallenged commands, the air of rebellion that enveloped him like a shroud, making Oswald’s blood simmer with a mix of irritation and disbelief. Victor had always been obedient—at least that was the narrative Oswald had rehearsed in his mind. But now, it felt as if Victor was slipping through his fingers, like grains of sand in an hourglass, and Oswald could hardly bear the thought of losing his grasp.

And he couldn’t allow that to happen. He turned sharply at the faint sound of footsteps approaching, his body tense with anticipation. Victor materialized at the doorway, his expression a carefully crafted mask of neutrality, but Oswald's keen eyes caught the flicker of uncertainty shining in those dark irises. The younger man had not braved this confrontation willingly; rather, the palpable tension between them crackled like electricity, a storm brewing on the horizon of their fraught relationship.

Victor had been evading him for days, perhaps even longer, darting around their usual encounters like a moth evading a flame.

“You’re late,” Oswald remarked smoothly, his voice laced with a quiet venom that only Victor could discern. “I wasn’t aware I was on a schedule,” Victor replied coldly, a hint of defiance coloring his tone, and the dismissive flicker of his gaze told Oswald all he needed to know about Victor’s restless spirit.

Oswald’s lips curled into a knowing smile, one that barely reached his dispassionate eyes. He took a slow, deliberate sip from his glass, savoring the flavor and the moment, before setting it down on the bar with a soft click. His dark gaze remained fixated on Victor as he began to circle around the room with an air of predatory grace. There was a hunger within him, a need to reclaim what he felt was being taken away.

“I’ve let you get away with a lot, Victor,” Oswald said softly, his voice draped in an almost seductive gentleness. “But you seem to forget your place sometimes. You think you can walk away from me? Think you can slip from under my control?”

Victor’s lips parted to retort, but Oswald was faster, his instincts honed from years of navigating the treacherous waters of Gotham. Before Victor could respond, Oswald closed the distance between them, his movements fluid and deliberate.

“You can’t get rid of me that easily,” Oswald said, his tone mingling amusement with something darker, something foreboding. His hand lifted, fingertip grazing Victor’s chin, tilting it gently yet insistently, forcing the younger man to meet his unwavering gaze.

Victor’s heart skipped a beat as he found himself ensnared in the depth of Oswald’s gaze, something profound and powerful coiling in the air between them. There was no escaping the grip Oswald had on him—physically, emotionally, psychologically—like a spider weaving its web. He had tried to break free; he had tried to resist. But Oswald was always there, a constant shadow lurking in the corners of his mind.

Victor’s breath hitched as he pulled back slightly, feeling nerves and frustration race through him in equal measures. “I’m not trying to get rid of you,” he managed to reply, though his voice lacked the confidence he intended to project.

Oswald smirked, the low, sultry chuckle that followed sending shivers down Victor's spine. “Oh, but I’m not trying to get rid of you either, Victor. Not at all.” As the cool touch of Oswald’s fingers brushed against Victor’s skin, an involuntary shiver ran through him, igniting a spark deep within. Oswald leaned in closer, his lips mere inches from Victor’s ear, the warmth of his breath sending a jolt through Victor’s frazzled senses. “I have other plans for you,” Oswald murmured, his voice low and possessive—a promise laden with implications. “Plans you won’t be able to escape. Not this time.” Victor’s chest tightened as dread and anticipation collided violently within him, each pulse of his heart reminding him of the conflict raging inside. He had fought relentlessly to distance himself from the looming specter of Oswald’s power, but it was becoming painfully clear that the harder he struggled, the deeper he sank into the intricate web the Penguin had spun around him. “I told you,” Oswald continued, his voice dropping even lower, each word dripping with silken menace. “You belong to me. And you will always belong to me. Don’t ever forget that.”

Victor’s heart hammered against his ribs as Oswald’s grip tightened on his chin, forcing him to look up and confront the unwavering intensity of the older man's gaze. There was no escape, no turning back now. Oswald had expertly cornered him, ensnaring him right where he wanted him. And despite the hate that simmered within him for allowing such power over his life, a part of Victor yearned for it—a dizzying need that drove him mad. “You think you can just walk away, don’t you?” Oswald whispered, his lips brushing tantalizingly close to Victor’s cheek, as if sharing a secret meant only for the two of them. “But no, you’re mine, Victor. You’re never going anywhere. And if you try? I’ll make sure you stay exactly where I want you.”

Victor swallowed hard, the weight of Oswald’s promises sinking deep into the recesses of his mind. Each syllable wrapped around him like chains forged of desire and fear, solidifying the walls he had tried to fortify. He had attempted to distance himself, to build barriers, but Oswald’s power, his control—it was an unrelenting force. Oswald was an overwhelming tide, indifferent to Victor's attempts to retreat.

Oswald’s fingers trailed down Victor’s jawline, ghosting across his skin with a sensitivity that made Victor shudder, his mind racing with conflicting thoughts. The Penguin’s smirk deepened, an intoxicating cocktail of confidence and satisfaction as he reveled in the effects he had on Victor.

“I can see it in your eyes, Victor,” Oswald declared, his smile knowing and smug. “You crave this, don’t you? You crave my control. And you’ll never escape me.” Victor’s lips parted, but no words came forth. His body betrayed him, the tension that enveloped them thick and electric, making it hard to breathe. Oswald was right. While a part of him fought against the rising tide, there was an undeniable allure in surrender, a tantalizing draw that whispered of submission and loyalty. He was already caught in Oswald’s web, woven with complex threads of affection and fear. There was no escape—and even more confounding, he realized he didn’t want one. “Good,” Oswald whispered, his voice rich with satisfaction. “Because you’re mine. And you always will be.”

Victor closed his eyes, the overwhelming weight of Oswald’s words cascading over him. He had tried to break free, to walk away. But Oswald had always been one step ahead, and now, there was no turning back.

Notes:

Thank you for reading! If you enjoyed this story, feel free to leave a comment or share your thoughts. I’m always open to taking requests for any ship or prompt, so don’t hesitate to reach out with your ideas. I love creating more dark, twisted, and romantic tales for you all!

[cyanide-and-roses]

Who would you guys prefer a drabble on?

[yandere-writer-momo]

I had a dream about a terrifying, yandere Oswald Cobblepot. Everyone, you know the drill

[envihellbender]

Oswald being extremely yanderey to the point of beating the shit out of Victor

Characters: Victor Zsasz, Oswald Cobblepot (Gotham)

Content: physical violence, yandere, MDNI 18+

Victor didn’t usually get driven home by Oswald’s driver, however from the moment he’d been scowled at and told they were leaving the Iceberg he knew precisely why. Victor had sighed, rolled his eyes, and said coming Boss, prying himself away from the pretty redhead he’d caught the eye of. Oswald’s jaw was clenched and he hadn’t said another word the entire journey home. Victor whistled and tapped his foot, sighed, and fidgeted trying to pass away the awkward silence. After what felt like an eternity they finally arrived back home. Oswald hurried through the front door, as far as he could with his cane and a good few glasses of wine in his belly. Victor dragged his feet and took things a little slower, when he finally shut the door behind him he was unsurprised to see Oswald stood there in the entrance having placed his walking stick to the side and a vicious glare in his hazel eyes.

“You know, I’m really starting to think something’s bothering you,” Victor joked. Oswald stepped forward, his hands shaking with anger. He grabbed Victor’s collar with his small hand, and spun him to the right, finally slamming him against the wall of his estate. His pale fingers working their way up to Victor’s throat and squeezing.

“What’s got you all worked up, Boss?” Victor gasped, unable to hide the smirk on his lips. He squirmed as he felt his clit twitch and cunt heat up.

“You. Acting like a stupid, fucking whore,” Oswald yelled, his voice cracking as he did. Testosterone was causing it to break, and given his voice got higher when he was angrier it made him sound a little more deranged. That did not help Victor’s arousal, and made Oswald even angrier.

“Okay I always like a whore but I’m definitely not stupid.” Victor licked his lips after he spoke, letting out a whining sigh as Oswald gripped Victor’s neck tighter until he spluttered. “Unless you want me to be, daddy,” he added jokingly. His voice mockingly whiny. Oswald growled and pulled Victor forwards then slammed him back against the wall, causing a sickening crack as his head bounced. Victor blinked rapidly, swaying slightly as he grew dizzy.

“Why do you have to fucking make them drool all over you? The fucking girls at the club. You know I- fuck!” Oswald let go of Victor’s neck, letting him stand their unsteadily and then Oswald clumsily lifted up one hand and punched him in the jaw. “I hate it. Hate it hate it hate it.” He was rambling, his words slurring slightly as he grew more aggravated.

“Come on, Boss. You know I’m yours,” Victor said, still smiling despite his bruised face and probably concussion. “All yours. None of those bitches matter. All they are is a pussy to fuck and a sweet, sweet scar.” Oswald sighed and stared at Victor, a sulking anger still in his face.

“She was drooling all over you.” Oswald swallowed and his cheeks reddened. “That stupid fucking chorus girl. She was thirty seconds away from shoving your hand up her skirt.”

“Yeah. Probably,” Victor agreed. Oswald let out a whining hiss and grabbed Victor’s shirt. He pulled him forward before shoving him onto the floor. Victor stumbled and fell backwards, looking up at Oswald with darkened eyes as his breathing grew heavier. Oswald kicked Victor in the stomach again, and again, and again. If Oswald had stopped to think for a moment, he would have known Victor could’ve broken his wrist from the first strike. He knew full well Victor was letting him hurt him. It was obvious in everything from Victor’s small smile and his squirming, deep breathing arousal. That didn’t stop Oswald from kicking him until he was panting over Victor, before straddling his waist and cupping his jaw in one hand. He stroked his cheekbone with his thumb as he tried to catch his breath, feeling calmed by how beautiful Victor was bruised and beaten beneath him.

[yanderequeensmackdown]

Redemption Round 2, Bottom

[yandere-wishes]

So based on your what vision the Gotham boys would have I got ideas (I’m still new to the Gotham boys so this would be very out of character)

Dick and Jason would have anemo

Tim would have dendro

Damien would have pyro

I don’t know much about duke but maybe electro

I'm actually so surprised anyone noticed that 💞💞 okay so here is my full analysis on DC (batman centric) x Genshin Impact cross-over. Yes, I went super overboard w/ this lol.

💝 Batboys

We're on the same page about Dick,Tim,Duke, and Damian. It's just Jason that I think would differ

Bruce Wayne - Cyro, Claymore

Dick Grayson- Ameno, Polyarm

Jason Todd - Pyro, Claymore (Red Hood)

Jason Todd - Cyro, Claymore (Arkham Knight) my logic here is that despite hating Bruce, he ends up being so similar to him on a spiritual and fundamental level.

Tim Drake - Dendro, Polyarm

Damian Wayne - Pyro, Sword

Duke Thomas- Electro, Bow

Barbra Gorden - Electro, Catalyst

Kate Kane - Hydro, Polyarm

💝 Rogues

Obviously, I went too deep with Harvey's. He'd definitely have two visions, one for either side. I can fully image him having a vision before becoming Two-Face. However, sometime after the incident, while he's climbing up in Gotham's underworld, his Harv personality also ends up getting a vision. Also, he's totally a Sword user cause lady justice and all that.

Harvey Dent - Hydro/Pyro, Sword

Roman Sionis - Ameno, Bow

Oswald Cobblepot (Gotham) Cyro, Catalyst

Jonathan Crane - (Pyro/Dendro/Ameno), Polyarm : Now, onto Jonathan Crane idk if he'd be a dendro, Pyro or Ameno user cause all three fit his MO so well.

Edward Nygma- Dendro, Catalyst/Polyarm

Poison Ivy - Dendro, Catalyst

Selina Kyle - Electro, Sword

Victor zsasz (Gotham) - Electro, Bow

Victor zsasz (BOP) - Ameno, Sword

Dr Phosphorus - Pyro, Catalyst

Joker (general) - dendro, Sword

Harley Quinn - Pyro, Polyarm

Alexis Kaye - Electro, Catalyst

Jerome Valeska - Geo, Bow

Jeremiah Valeska - Hydro, Catalyst

Slade Wilson - Geo, Claymore

Respawn - Geo, Sword

Talia Al Ghoul - pyro, Polyarm

Ras al ghoul - Dendro, Claymore

💝 Other DC Heroes

Clark Kent - Ameno, Claymore

Jon-El Kent - Ameno, Catalyst

Conner Kent - Pyro, Catalyst

Hal Jordan - Dendro, Catalyst

Kyle Rayner - dendro, Sword

Oliver Queen - Dendro, Bow

Roy Harper - Pyro, Bow

Conner Hawke - Electro, Bow

Berry Allen - Electro, Catalyst

Wally West - Geo, Catalyst

Bart Allen - Ameno/Electro, Catalyst

Arthur Curry - Hydro, Polyarm

Garth - Hydro Sword

Jackson Hyde - Geo, Polyarm

Minhkhoa Khan - Ameno, Sword

Phantom-one - Hydro, Sword

Angel Breaker - Pyro, Sword

Diana Prince - Ameno/Hydro/Electro, Sword

Low-key really want to write a Genshin Impact DC AU. With reader as the traveler. Tyvat is still Tyvat, but the nation's are...

Gotham (Cyro)

Metropolis (Ameno)

Star City (Dendro)

Central city (Electro)

Coast City (Geo)

Atlantis (Hydro)

Blüdhaven (Pyro)

Themyscira (events only like the summer event)

I'm not quite sure what exactly would happen in the AU other than reader trying to find their sibling. Lord knows my Traveler would just be chasing down Harvey and Roman and doing their character quests. Just need to find out how to make it all yandere

Also, I forgot about the star system. Who do you think would be 4 starts, and who would be 5 starts??🤔🤔

[lonleywriters-blog]

What would Oswald Cobblepot do if when he brings his Darling out of the house for the first time, she does try to run away like he thought she would? She clings to him instead

Ofc my darling

Yan. Oswald with clingy newly taken darling

He is very shocked at first, going stiff for a moment. It's doesn't take long before his arms are wrapped back around you tightly. He would question it, but it's far too good to ruin. He just thanks whatever is out there for this gift as you hug his waist tightly. You almost seem like a kid when a mom drops them off for school with how desperately you cling to him. He brings a large, warm hand up to stroke the back of your head gently. He can't fight the small grin that breaks onto his face as he sways you both side to side gently.

"Thank you darling." He says quietly, close to your ear.

You can't do anything but nod before pulling beck to rest your chin on his chest. Looking up at him with wide eyes, eyes that made him weak. You admire the man you had already fallen in love with for few seconds before smiling and nuzzling his chest. He chuckles as he walks with you slightly lifted off the ground, still laying your head on his chest. He walks to the couch and plops down before putting you on his lap.

"Do you want pizza or Chinese food for dinner my love?" He asks with a sweet smile, and like that the start of your new life begun.