#yandere Oswald cobblepot

[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.

[d3athmaskd1v1n3]

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?

[yandere-toons]

Yandere Oswald Cobblepot (Platonic & Romantic Headcanons)

Warnings: Mentions of Gore, Violence, Blood, Stalking, Alcohol Use, Use of Firearms, Mentions of Torture, Death, Undeath, Desecration of Corpses, Mention of Abduction, Incarceration, Psychological Manipulation.

Platonic:

From his days of spying and backstabbing as a human footstool for Fish Mooney, Oswald has understood that most relationships are transactional and devoid of real intimacy. Hence, he becomes so readily attached when someone goes out of their way to make his time on this earth a little easier.

In this person, whom he now wishes to have as a lifelong friend, Oswald sees a shining exception to human ugliness, for whose sake he is willing to break laws, spend vast sums of money, and take lives to keep with him. The late Gertrud Kapelput taught him that one must give everything to those dearest to one's heart, a lesson Oswald will honour for the rest of his life.

In addition to assassinating people on his friend's behalf, this devotion translates to buying out entire inventories of jewellery and clothes for them. He offers free drinks at his nightclub, guarantees protection if they operate a business, and provides super-secret special access to all his mother's recipes.

Being sentenced to Arkham or Blackgate is no matter when Mayor Cobblepot is eager to finagle the early release of an old friend. He will blackmail, intimidate, and coerce all the appropriate offices until the person he wants is back with him. Oswald becomes exceedingly irritable and anxious if separated from his friend for too long.

He relies on them to lend him an ear whenever he needs to castrate a rival verbally. Although he is not the most cooperative, Oswald is sensitive to any advice from his friend, a sensitivity that doubles if they tell him he is a good man.

As soon as they are more than a few hours late for a meeting and have not contacted him with an airtight explanation, Oswald is howling at his goons to find them and phoning the GCPD to babble about filing a missing persons report. He refuses to sleep or stop pursuing their alleged killer after his worried heart tells him they lie dead in an alley.

Oswald is drowning in grief and hysteria, attacking anyone who delivers bad news about the search when his friend returns to him alive. He collapses into their arms and rejoices that he can delay learning how it would feel to live without them a bit longer, at which point he begs them to clear their schedule in favour of accompanying him through his day.

If anyone dares make a laughingstock of this relationship and, by extension, him, Oswald paces up and down his home while guzzling wine and ranting about how he will roast these people's entrails like chestnuts over an open fire.

Practising emotional honesty for something other than anger takes every courage Oswald can summon. It is safer for him to live out his days half-satisfied and fantasizing than to put his hopes to the test and risk terrifying rejection, so while he is weighing the pros and cons of coming clean, Oswald awaits a sign that the attachment is reciprocal.

In his ideal world, he lives in his father's mansion and drinks tea with his mother and friend while everyone talks about how he proved the critics wrong and became a great man despite everything. This dream will never come true for various reasons that keep Oswald awake at night, so he persuades his friend to take one of the guest bedrooms and dispatches those who might threaten his monopoly on their attention.

He does much to sweeten the deal, which, when broken down to its most basic elements, is a request for his friend to devote themselves to him, as Gertrud did and as he says he did for them. A gourmet breakfast and dinner from Olga every day are a given, but the only item on which Oswald will not make concessions is permission to leave Gotham.

Suppose his friend chooses a life of crime. Oswald considers himself their proudest and most adamant supporter. If they are arrested, he will burst into the police station with an army of sycophants — if necessary, an angry mob of misguided citizens — and demand that all charges be dropped. If the GCPD resists, he will send Victor Zsasz to raid the precinct in a hail of bullets or turn the case into a political issue for the cameras and journalists to shame the police into submission.

A constant sense of danger looms over the friendship, like wolves over a sick deer. Oswald sees it every day in the crowds wishing him to suffer, in the way his heartbeat jumps and pushes him to lash out each time someone approaches his friend with a suspicious look. This hypervigilance may one day prove too stressful, and Oswald decides his best course of action is to fake his friend's death and sequester them in a safe house until he rules Gotham's underworld with absolute power.

If they do die, Oswald embraces their corpse and wails like a lost child until he has to retreat to survive or gets a chance to mangle the one he thinks is to blame. Afterwards, he is subject to fits of rage and melancholy when reminded of his departed friend and enlists Hugo Strange to revive them.

Operating under a fat paycheck and the threat of torture if he fails, Strange is cleared to sacrifice as many people and make as many monstrous modifications as necessary to succeed. Driven mad by loss compounded, Oswald finds scarcely a price not worth paying if it allows him to have back one of the few bright spots in his life.

Romantic:

In terms of relationship security, Oswald experiences some cognitive dissonance. He wants to believe that his partner will never abandon him, but at the same time, he fears losing them to anyone with a pulse.

Oswald, pathologically insecure, suspects his partner of finding a replacement for him after one ill-timed joke, one misunderstood smile, or one rejection of another's flirtation that he does not feel was direct enough. He flies into a tirade about how they lead him on and play with his emotions to leech off his wealth and influence.

This explosive tantrum sends his every minion scurrying far away, for whichever lackey is standing closest to him at that moment will be stabbed in the neck with a broken bottle or beaten senseless with a fire poker, depending on the setting. Even though the physical aspects of his rage never touch his partner, the threat of what he could do to them is present evermore.

Throughout his life, the only people who have invariably been kind to him without ulterior motives are his parents, especially his mother. Therefore, a genuine compliment from his partner overwhelms him with the feeling of being wanted and makes him grossly overestimate his importance to them.

If someone claims that his partner has been disloyal to him, Oswald disregards any evidence as forged and maims the messenger for, in his eyes, being a filthy liar. The only way he would believe such a thing is if he uncovers the evidence himself, in which Oswald would rather blame a third party for forcing his partner's hand than let go of the comforting delusion that this relationship is meant to be.

As his rise to power destabilizes him mentally and puts a glaring target on his back, Oswald fears leaving his partner alone, even for a minute. His paranoia spirals out of control until he becomes obsessed with the possibility that enemies he knows too well and those he has yet to discover will come to murder or kidnap and torture the last good thing in his miserable existence.

Oswald assigns Victor Zsasz to keep vigil over his partner day and night for the foreseeable future, giving Victor — who in turn gives his henchwomen — strict shoot-on-sight orders for any visitors not on his list. The list is shorter than a pig's tail and consists of Oswald himself, Victor and crew, and as an on-again, off-again member, Edward Nygma.

In his deranged mind, not even Jim Gordan has business speaking to his partner without him there to monitor the interaction. Suppose Oswald gets the impression that someone is trying to wheedle information out of his partner or bully them into betraying his trust. In that case, this interloper is slain with extreme prejudice at the earliest opportunity.

Suppose a friend or family member decides to come over unannounced and receives a bullet to the brain, que será, será. Oswald has convinced himself that all the others in his partner's life are traitors waiting to happen, or, if not traitors, vulnerabilities that his enemies will use to lure his partner away from the safety of his watchful eye.

Acts of disrespect towards those he cares about make Oswald apoplectic, so if he hears anything about anyone accosting or assaulting his partner, someone is getting an umbrella crammed down their throat.

Whether he beats the culprit to death with a baseball bat, lets Victor have fun with them, or mounts their severed head on one of his end tables and calls it a decoration depends on the severity of his partner's distress. If tears are shed, and blood is bled, whoever caused them this pain is hunted like an animal and reduced to meat paste.

Through mass execution and permanent disfigurement, Oswald makes it clear that his partner is off-limits to Gotham's underworld, even to those members who have been licensed to do wrong by the Pax Penguina. Anyone still holding them at gunpoint loses an arm and then a life, and Oswald insists that he take that life himself because everything that threatens his partner threatens him, too.

If in Arkham together, Oswald deems himself far more honest than the rest of these ruffians and thus makes a promise. Any violence against his partner will be inflicted tenfold on the perpetrators, whom he adds to his big book of names to disappear once he regains his status as King of Gotham.

Locked alone in the asylum, Oswald worries that his partner will leave and forget about him. Once free, he tracks their current address by any means necessary and seeks confirmation that they have not forsaken him. This absence has so reinforced his inability to separate that the appearance of a new person or a request to distance himself from them is perceived as a betrayal.

Although Oswald will always forgive his partner, he will not quit plotting revenge against those who gave them these terrible ideas. The day of reckoning for these pond scum will come when and how he pleases. In the meantime, he would like to share a ribeye steak with his partner while everyone else in Gotham starves.

[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.

[lonleywriters-blog]

Hello! I’ve been following you for a while and never sent I’m any requests but I think nows my time! How about Yandere Gotham Villains with an s/o who is having extreme gender dysphoria? Preferably FTM. Thank you and love your writing!! :]

oh of course darling

Yan. Gotham villains with an FTM s/o having gender dysphoria

Jerome doesn’t quite get dysphoria, but he will try his best to help you.

 He will sit next to you and rub your back.

“Darling you look perfect.” 

He doesn’t understand of course you are a man. 

“Babe I love you so much, of course you are a man” 

He tries his best to help in anyway he can. 

timidly hugs you and gives you a kiss. 

He cant stand seeing you sad

You are his world and shall someone hurt you they die

He doesn’t know what to do in this situation

He will hug you and tell you how handsome you are

Tries his best to make you comfortable 

He will lay down in bed with you until you fall asleep 

Edward understands dysphoria 

He will have a long talk with you to understand what you are feeling and why

He brings you a big sweatshirt and pants

reassures you anyway he can

distracts you with silly riddles 

He is not the best at comfort 

He hugs you and showers you with affection 

“You are the sweetest man I have ever met” 

He will google what to do 

“do you want me to do anything”

She is confused

Tries to help you to the best of her ability 

Will ask you why you feel the way you do

She will talk you through it and will have a cute date to distract you 

He understands how you feel

He will hug you and comfort you

rubs your back and praises you

He will kill however made you feel that way

If its no ones fault he will just cuddle you and watch movies with you 

[yandereforme]

Yandere Batfam x Single Mother! Martha Lookalike! Singer! Reader

Part 6: Familiar strangers and odd behavior

So, normally, you and your kids don’t spend most of the day together during the weekend, since that was when you worked most. However, since your boss, Mr. Cobblepot, was apparently hosting a family friendly function at the Iceberg Lounge, and had even told you specifically you could bring your kids, you were now wearing a pretty black dress and heels, nervously fiddling with your kid’s little suits.

Thankfully, Jason was also invited and attending.(He had insisted on helping finance your dress, while Damian, who apparently was invited but couldn’t attend due to a ‘prior engagement’ dressed the twins. Celeste was now wearing a pretty light blue dress while Perseus was wearing a bite sized navy tux.) Jason had even chosen to match Perseus’s outfit, joking that since he was Perseus’s uncle, he should match.

(This comment was due to how sometimes when you’re in public and people noticed how good he was with the kids, they assumed he was at your brother or your husband fuck you and Jason bit disgusted at the husband remarks, but pretending to siblings was easier)(Jason always seemed so happy when that happened.)

After arriving, Mr. Cobblepot welcomes you with open arms, and you smile. While he can occasionally be grumpy or cold, he’s always been a kind boss, and appreciates your music. He trusts you to choose appropriate music, a rarity as you have seen with your other singing colleagues.

(You don’t know, but Cobblepot is extremely fond of you, seeing you as almost a daughter to him. He has already nicknamed you Nightingale, and adores every one of your shifts. He pays you much more, claiming it’s due to your music bringing customers in, but everyone knows you are his favorite employee, except for you, of course)

You spend most of the night dancing with your kids and Jason. You even see Tim and chat with him for a bit before Cobblepot calls you over to introduce you to some of his colleagues.(You try to ignore the tension between your boss and your friend. As long as they don’t start brawling, you refuse to let this ruin your night.)

Then, after Jason and Cobblepot take aside a man who was harassing you, you take a small break, and Celeste starts fussing. Now, you were just trying to calm her down before she set Percy off, but then a stranger managed to distract and entertain your children by doing a somersault as he approached.

You talk for a while with him. His name was Dick, though it takes a long five minute conversation before you understand that he was actually called that. You were a bit suspicious about him approaching you, especially since he seemed captivated by your kids, but after hearing him gush about his siblings and chat amicably with you for almost twenty minutes, you were pretty sure he was just a decent guy before Jason came over.

Jason and Dick seemed to almost have an aggressive joke going on during the introductions. You notice the odd behavior, and the blood on Jason’s knuckles that he was trying to hide, but it was a long night, and you were tired.

Then, the power went out and you only have a minute of confusion before everyone starts freaking out. You quickly hand Jason Celeste and Perseus, knowing he is the least likely to get bowled over in the chaos. You get swept up in the crowd almost immediately, swept away. You barely manage to get out of the Iceberg Lounge when the gunshots start.

You were just standing in the Alley, catching your breath, when Batman arrived to take care of the matter, Robin at his side. You just stay in the alley away from the crowd, trying to avoid being swept away while you look through the crowd, hoping to find Jason with your kids. Instead, you lock eyes with Batman, who almost seemed to pale when he looked at you.

The staring is so intense yet…. The eyes seem almost familiar in some way. You unconsciously take a step forward, almost feeling a pull towards him, but the crowd sweeps you up quickly.

It takes five more minutes for you to find Dick, who thankfully has his phone on him. It only takes him five minutes to get Jason to answer and come over with your, thankfully fine, kids. By the time Jason is at your side, worryingly checking you for injuries you don’t have, you have made a new friend and exchanged phone numbers.

The night ends with Jason staying the night and you falling asleep with your kids in your arms. Unbeknownst to you, the night also ends with another man obsessed with you, Jason swearing he will protect you better(he can’t stop thinking about those twenty five minutes where he didn’t know where you were as shots rang out and he had to pray to a god he hadn’t believed in since he was fourteen that you were okay) and a man who spends the night recovering from “hallucinating” his mother in the mouth of an alley during a fight. Meanwhile, a man you hoped never to hear from again crosses into Gotham to find the children he never wanted and the girlfriend he never cared about.

Edit: I think I should clarify the timeline

We start with you moving to Gotham, and the babies are only a month old.

1 month in: You sing to Red Hood

1 month, 1 week in: You meet Jason

2 months, 2 weeks in: You save Robin/Jason becomes full on yandere

4 months 1 week in: You meet Damian

6 months 2 weeks in: You meet Alfred

7 months: You sing to Tim/he becomes yandere

8 months 1 week: The Icerberg Lounge is attacked

Yan Batfam x Singer! Single mom! Martha lookalike! Reader

( I know it’s a lot but they are all important to the plot)

Part 1:Beginnings and first encounters

You are Bruce’s bio daughter. Your mom, who didn’t know who the father of her kid was, gave you up to your aunt to be raised by them, but you didn’t know until your adoptive parent’s funeral that you weren’t their biological daughter. You had twins recently with a shitty ex of yours who you broke up with not long before the funeral after he tried to hurt your daughter for crying.

After the funeral, where you learn that your bio mom wasn’t sure who your bio dad was, but that she knew he lived in Gotham, you decide to move to Gotham. In part due to your biological father, in part due to avoiding your ex(who had refused to be listed on the birth certificate since you gave birth during a break in your relationship), and in part due to the basically free house your bio mom had owned in Gotham. So, you moved with the twins to an abandoned, slightly dilapidated house just outside of Crime Alley, and got yourself to work.

You got a job at the Ice berg Lounge, in part due to there being an opening, and in part due to you helping two women who worked there who apparently worked right under Mr. Cobblepot?

You quickly got a reputation as a singer with a knack for knowing just what song fit a customer. It was a bit of a game between you and the other workers, where they would point out a person and you would sing a song based on their vibes. You always managed your hit home with your songs, leading to you becoming one of the most popular performers at the Iceberg Lounge.

That’s what leads to Red Hood coming in one night. He had heard about you from a few of his men, and wanted to know what all the hype was about.(This take place during the Red Hood arc, where he has already been established as a crime boss but the Batfamily doesn’t know his identity)

Cobblepot asked you to sing a song for Red, and pointed him out to you. You knew who he was, you were just outside his area, and honestly you kind of liked what he was doing for the community, so you were willing to preform, even offering to sing two songs about him(something you had only done a few times with regulars who you really liked.

Jason accepted. You started off with You’re Gonna Go Far, Kid by The Offspring. You didn’t usually do a lot of rock songs, but that song resonated with you when you looked at him.(Jason loved the song. It was angry but fighting music, and your voice was really good. He understood why so many of his men praised your music(he just couldn’t understand why you looked so familiar))

The next song was different. You didn’t usually sing two songs, and the few times you did, people tended to vary reactions, from shock to anger to accidentally setting off a break down. But you had promised. You just hoped Red Hood wouldn’t hate you for the next song(you didn’t understand why it felt so right to sing the next song, when it didn’t seem like a Red Hood song, but you didn’t want to question it now.)

Then, you sang Good for you by Olivia Rodrigo, and everyone froze. (Jason didn’t know how you knew this anger of his. How did you know how he felt about Bruce replacing him? How did you know?) No one understood the song, especially when the recipient was a murderous crime boss, but they didn’t interrupt.

After you finished the song, you looked at Red Hood. He was sitting ramrod straight. You couldn’t see his face, but his posture was very tense. Slowly, he stood up, and walked to the stage. You didn’t know what you expected, but it wasn’t for him to drop $200 in your tip jar, and leave without a word.(Jason’s head was spinning. The green wasn’t invading, but it surrounded the edges of his vision. He needed to leave. He had to come back again, probably as a civilian, but for now, he needed to leave.)

After that, you got even more visitors, and a raise in your salary. You even made a new friend, Jason, and you were even starting to consider sending your kids to daycare instead of a baby sitter(you wouldn’t do that. You liked your arrangement with the street kids, where you would pay them in food and cash to watch your kids during the day. You liked taking care of them, but they needed to feel like they were doing stuff for you, so you didn’t make a fuss.)

Then, the Joker got out of Arkham.

Edit: I hope you guys enjoy this. This will probably be a series. I’ve had this idea for ages but never got around to it before now. This isn’t related to my Bruce or Jason series, which I will do, but I just wanted to finally put the on here. Please comment any suggestions for the kids names, or what you want to see next!

[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 •‿• !!

[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!

[writers-wrongs]

I'm begging please yandere gotham oswald cobblepot with a male readers hc

For a queer character there is surprising lack of male reader stuff with him

i think thats bc you can just pretend youre eddie for the experience lmao. but yeah, we need more ozzie content. btw, this is only gonna cover season oneish, mostly bc this man goes through so much and i cant possibly cover it all in one post

yandere!gotham!penguin x male!reader

-you work at fish's club as a waiter, so hes known you for a while. youre one of the only people who treats him with any kindness, the only others being his mother and (sometimes) fish, so he spends most of his free time with you

-he falls for you hard and fast, but he takes a while to recognize it as love. hes been bullied all his life, so he assumes that his feelings for you are just friendship. of course, his mother recognizes her son is in love and gives him a little talk (she assumes its a woman, but her hearts in the right place). once he knows hes in love, he does absolutely nothing with that knowledge

-dont get me wrong, he utterly adores you. youre on his mind constantly. he just doesnt feel like hes important enough to have you yet. why would you ever want a pathetic little umbrella boy? so he stays friends with you, and he starts planning. if he doesnt deserve you now, he'll have to work to earn you

-then the whole "fish tries to have him killed for betraying her" thing happens. and up until he takes over her club, theres not much he can do about you. hes moreso focused on survival at the moment. but when he takes the club, he keeps you around and promotes you to co-owner

-this man spoils you constantly. you want a new suit? he gets you a personal tailor. you say you like a color? the club is covered in it within the week. you say you dont like someone? theyre found dead the next day, and zsasz has a new tally on his arm. anything you want, he takes to the extreme

-aaand now hes fighting for his life again. my poor boy, hes suffered more than jesus and weve only just finished season one. hes now the self-proclaimed king of gotham, and his ego is through the roof. his first act as king? shows up at your doorstep with a bouquet of purple roses and begs you to be his

-if you accept his love, you rule gotham by his side. directly by his side. you two share the throne in the most physical interpretation of the phrase, this man is so clingy. youre never out of his sight for more than an hour, and if you are, all of his men start searching the city for you. oswald practically worships you. to the gotham underworld, youre known as his better half. if someone can convince you to let them live, oswald will listen because thats what his lovebird wants, and what his lovebird wants, he gets

-if you dont, he does his best not to cry. in front of you, that is. he rushes to his mom and sobs for hours. once he calms down, gotham becomes a dark place. no mercy is shown to anyone who messes up, infighting is almost encouraged, and the only rule of the penguin is that youre not to be hurt. people are allowed to affect your life, though. any partners of yours tragically die, youre constantly put into (controlled) danger, your apartment even gets broken into so you dont feel safe at home. if youre not going to embrace oswald willingly, he'll just frighten you into running into his arms

[d3athmaskd1v1n3]

Hey, I was wondering if you could write yandere TNBA Oswald Cobblepot with a reader who’s a singer

TNBA Oswald Cobblepot with a reader who's a singer headcanons

Thank you for the request! I'll try to come up with something good for you! I have to say, I love the concept. (CW: Possessiveness, manipulation, unhealthy relationships, murder)

You were working as a longue singer in some seedy bar downtown when Oswald found you. He immediately was taken with your talent as well as your image.

He offered you a job at the Iceberg Longue with more than twice the pay that your current job gave you. You accepted, of course.

Oswald always makes sure to keep an eye on you. He's hired a few bodyguards to stay with you when you aren't working. If you have any complaints about it, he'll just brush them off. He says it's to keep obsessive fans away from you. After all, somebody as talented and beautiful as you is bound to attract a few crazies!

If he gets the feeling you might want to quit, he'll shower you with gifts. Very expensive gifts. He's not even subtle with the love bombing.

Anyone ogling you when you're performing is swiftly dealt with. Oswald tries to be discreet about it, but it isn't hard to figure out he's pulling these people aside and bringing them to a backroom to kill them.

At this point you may be too scared to say anything about it. You want to keep your job. Oswald has the influence required to get you blacklisted if you decide to step out of line, making it impossible to get a job elsewhere.

So you keep your head down, and just put on a happy face as you go back on stage.

[yandereworlds]

More new bots!

Hey there! It’s been a while, but after seeing the amount of positive feedback I got from you guys for my previous yandere bots, I decided to make a fresh batch, but these ones will be canon characters! Please, let me know what you guys think of them and send me any thoughts or any form of feedback, I’d be happy to read all of them! Here’s the new bots. //Mun Kiki

Oswald Cobblepot [Yandere]

https://beta.character.ai/chat?char=EzXt6429t4aDe9XCxPenmMKsICq_684OSvo2mQrvb5c

Homelander [Yandere]

https://beta.character.ai/chat?char=w5C7nqhcOhQjsN62sOE5iMtKLa7b2lfN4KMSBe1ytIc

Overhaul [Yandere]

https://beta.character.ai/chat?char=MhaTYwtl5ud7rmDbSwRx6ZHwY2qN5X8Kx0uq0_b6Wyw

[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.

[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

[yanderequeensmackdown]

Redemption Round 2, Bottom

[stab-me-mommy]

we all need a yandere dommy mommy sometimes, don't we?

i'm nosferatu. 21, any pronouns. and i really fucking like yanderes.

this means that on this blog, you get to see your favorite characters as a yandere. well, my favorite character, but that's just details.

i write yandere stuff on my other blogs, so i'll just list off fandoms i don't have blogs for.

slashers:

Jason Voorhees (Friday 13th series)

Pamela Voorhees (Friday 13th series)

Freddy Krueger (Nightmare on Elm Street series)

Tiffany Valentine (Child's Play series)

Charles Lee Ray (Child's Play series)

Billy Loomis (Scream)

Stu Macher (Scream)

Pearl (Pearl movie)

Hannibal Lecter (Silence of the Lambs; book/sir Anthony Hopkins version)

Bubba Sawyer (Texas Chainsaw Massacre movies and game)

Drayton Sawyer (Texas Chainsaw Massacre movies and game)

Nubbins Sawyer (Texas Chainsaw Massacre movies and game)

Chop-Top/Robert Sawyer (Texas Chainsaw Massacre movies)

Sissy Sawyer (Texas Chainsaw Massacre game)

Johnny Slaughter (Texas Chainsaw Massacre game)

Ji-woon Hak/The Trickster (Dead by Daylight)

Jason the Toymaker (Creepypasta)

Laughing Jack (Creepypasta)

games:

Karl Heisenberg (Resident Evil: Village)

Allied Mastercomputer (I Have No Mouth And I Must Scream - game version)

Narrator (The Stanley Parable)

Fate (Death and Taxes)

Bigby Wolf (The Wolf Among Us)

Bluebeard (The Wolf Among Us)

Tanner Grayton (Scrutinized)

Ascended Astarion (Baldur's Gate 3)

Cazador Szarr (Baldur's Gate 3)

Raphael (Baldur's Gate 3)

Haarlep (Baldur's Gate 3)

Genji Shimada (Overwatch/Overwatch 2)

Reaper/Gabriel Reyes (Overwatch/Overwatch 2)

Alduin (The Elder Scrolls V: Skyrim)

Molag Bal (The Elder Scrolls series)

Mehrunes Dagon (The Elder Scrolls series)

Hermaeus Mora (The Elder Scrolls series)

Hircine (The Elder Scrolls series)

Sanguine (The Elder Scrolls series)

V/Jihyun Kim (Mystic Messenger)

Jumin Han (Mystic Messenger)

707/Saeyoung Kim/Luciel Kim (Mystic Messenger)

Unknown/Ray/Saeran Kim (Mystic Messenger)

Two-Face/Harvey Dent (Batman: Arkham Series)

Il Dottore (Genshin Impact)

anime/manga:

Shuu Tsukiyama (Tokyo Ghoul)

Dio Brando/DIO (JoJo's Bizarre Adventure: Phantom Blood and Stardust Crusaders)

Kars (JoJo's Bizarre Adventure: Battle Tendency)

Light Yagami (Death Note)

L Lawliet (Death Note)

Misa Amane (Death Note)

M/Mihael Keehl (Death Note)

Yato (Noragami)

Asura Kishin (Soul Eater)

Arachne Gorgon (Soul Eater)

Medusa Gorgon (Soul Eater)

Giriko (Soul Eater)

Justin Law (Soul Eater - manga version)

Noah - Greed (Soul Eater)

Noah - Wrath (Soul Eater)

Franken Stein (Soul Eater)

Elf (NANBAKA - version)

animated series/movies/cartoons:

Seraphim (Blood of Zeus)

Zeus (Blood of Zeus)

Hera (Blood of Zeus)

Apollo (Blood of Zeus)

Hades (Justice League Animated)

Asmodeus (Helluva Boss)

Mammon (Helluva Boss)

Valentino (Hazbin Hotel)

Vox (Hazbin Hotel)

Adam (Hazbin Hotel)

Bill Cipher (Gravity Falls)

live series/movies:

Merle Dixon (The Walking Dead)

Daryl Dixon (The Walking Dead, early seasons)

Lucifer Morningstar (Lucifer)

Edward Scissorhands (Edward Scissorhands)

Willy Wonka (Willy Wonka and the Chocolate Factory)

Jerome Valeska (Gotham)

Jeremiah Valeska (Gotham)

Scarecrow/Jonathan Crane (Gotham)

The Mad Hatter/Jervis Tetch (Gotham)

Penguin/Oswald Cobblepot (Gotham)

The Riddler/Edward Nygma (Gotham)

Victor Zsasz (Gotham)

Barbara Kean (Gotham)

Loki Laufeyson (Avengers 2012)

comics:

The Batman Who Laughs/Bruce Wayne (general concept)

The Grim Knight/Bruce Wayne (general concept)

Batman/Bruce Wayne (general concept)

Owlman/Thomas Wayne Jr. (general concept)

The Joker (general concept)

Harley Quinn/Harleen Quinzel (general concept)

The Hulk/Bruce Banner (general concept)

Superman/Clark Kent (general concept)

Ironman/Tony Stark (general concept)

Deathstroke/Slade Wilson (general concept)

the list most likely will get updated.