#Gotham!Oswald cobblepot x you

[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

[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 •‿• !!

[mysticalarmand]

How did his scrawny ass

Pull two of the most dangerous people in Gotham

[knoepfl]

DC Masterlist

Here is the DC Masterlist! Here I will post everything about DC! So if your a fan be sure to keep checking this Masterlist. I will show updates as soon as possible!

Last Updated: 03.01 25

Main Masterlist

Characters: Arthur Fleck, Heath Ledger, Jeremiah Valeska, Jerome Valeska, Jervis Tetch, Jonathan Crane, Oswald Cobblepot, Edward Nygma, Viktor Zsasz

✧ The Joker

✧ Arthur Fleck

A Warm Embrace

Beyond the Mask

A Night of Firsts

Bang Bang

A Cozy Christmas

A Fleeting Fantasy

Part 1

Part 2

A Christmas Dance with Arthur

Christmas Feelings Christmas Special 7/24

✧ Gotham Series

✧ Edward Nygma

The Riddle of Us

✧ Jeremiah Valeska

Pain and Pleasure

✧ Jerome Valeska

Laugh Until It Hurts

Guess Who's Back!

✧ Jervis Tetch

Down the Rabbit Hole

Madness in Mourning

Trapped in Wonderland

Mad as Love

Madly Festive Christmas Special 4/24

✧ Oswald Cobblepot

A Kid For Christmas Christmas Special 14/24

✧ Viktor Zsasz

Stolen Shot

✧ The Dark Knight

✧ Heath Ledger

Unraveled Dreams, Twisted Love

✧ Batman: The Animated Series

✧Jervis Tetch

Tea for Two

A Very Merry Unbirthday Christmas Christmas Special 12/24

A Wonderland of Our Own Christmas Special 18/24

✧ Jonathan Crane

Shadows of Fear

✧ Arkham Games

✧ Edward Nygma

Mind Games

The Riddler's Reward

✧ Jervis Tetch

Through the Looking Glass

Down the Rabbit Hole

Tea Time Consolation

[elericelery]

joint comic by me and Cidney. I drew Oswald first and then Cidney drew the Riddler completing the story. We left space for text but decided we didn’t need it for this story Enjoy

[acapelladitty]

Oswald Cobblepot/Reader - Teasing 💖🐧

Summary: A commission for the absolutely lovely @nygmanotnashton in which Oswald Cobblepot finds himself on the receiving end of some fun teasing.

A surprisingly warm late afternoon had forced a full retreat to Ozzie's office as it was one of the few areas within the Iceberg Lounge to possess enough tasteful luxuries to make the suspicious heat seem bearable.

As always, Ozzie had immediately taken up residence in his favourite chair, more of a throne really, while you settled yourself comfortably against the solid oak desk, perched with your legs hanging off the side to block the stack of drawers which were built-in to the furniture.

Ozzie's thick fingers move with surprising dexterity as he taps away on his phone with a casual pace. A soft silence hangs in the air as you split your attention between your hanging legs, bouncing off the small brass handles of each drawer, and the uncomfortable way in which your shirt is clinging to your sweat-slicked back. The evening plans were long set and a gentle rumble in your stomach sparked a fresh excitement for the restaurant which Ozzie had booked for you both.

An Italian with a four month advance in bookings.

Well, four months to anyone who wasn’t Oswald Cobblepot and his plus one.

"You're quiet." Ozzie mutters, catching your attention with a quick nudge of your leg.

Looking up, you met his gaze and the questioning look there forces a small smile to tug at your lips as you pick up on his unspoken concern.

"I'm just thinking, Oz." You answer, tapping the heel of your foot against the wood. "Nothing too fun or exciting."

"What would it take to make my pretty bird sing then?" He hummed in response, running his finger along your clothed knee until his palm enclosed the joint to rub at it gently. "A new foreign car? Some expensive trinkets? Or should I say, more expensive trinkets? How about a full inch?"

"Only an inch?" You cut in quickly while your body shifts, ghosting your shoe along the bulge in his slacks as you tease him with a sudden playfulness. "Now i’m worried. What happened to the rest of it?"

Ozzie’s laughter is easy and open, his large chest shaking with the effort as he fixes you with a heated glance.

"Keep your foot there and you'll be seeing it sooner than you think, dear."

He leans forward and makes to reach for the drawers which are hidden behind your legs. Sensing another opportunity for some fun, you spread your legs for him to reach between, rather than moving them off to the side. A salacious move which nets you another small chuckle as he presses his knuckles to the inside of your thigh before pulling free the middle drawer.

Unable to see what he's doing, you instead allow your eyes to wander past him to the extravagant fish tank which sits behind his desk. Fish of many colours and sizes flutter around the water with the casualness of creatures that know they're well fed and taken care of.

A feeling you know well, and one which makes a goofy smile tug at your mouth as you drop your eyes to Ozzie once more and lean forward enough to run a gentle finger along the back of his exposed neck.

"You're trying to kill me today." He growls, shuddering at the soft touch. His neck had always been particularly sensitive, and you exploited that fact with unrivalled joy.

Leaning back, his thick body filling his chair like the king he were, thick fingers produced a stack of crisp, neat bills which were wrapped together by a straining rubber band; the heft of the bills easily sitting at over an inch wide as he quickly thumbed through the money to ensure it was all there.

"Would this be enough?" A teasing smile touched at Ozzie's thin lips, the edges curling upwards as he held the stack of money out.

"Hmm," you pretend to think it over for dramatic effect, "I could probably buy something nice to wear out for dinner and then something even nicer for you to rip off after."

Reaching for the money, you find it snatched away in an instant.

"Hey-"

"Nothing for nothing, my darling."

"Ozzie, please. You don't have to-"

"Nothing for nothing." He repeats, the words gruff yet bordering on a sing-song quality as he reclines in his chair even further.

Grumbling playfully as you were forced from your comfortable perch, you join him on his chair - carefully placing your knees on either side of his bulging frame as you lean gently against his expansive chest.

Catching his lips in your own, he tastes of red wine and you groan into his mouth as he reacts to you immediately; wrapping an arm around your waist to hold you in place as he enjoys the messy kiss. His presence envelops you and you bite at his lower lip until you pull away to catch your breath a little.

"Maybe I should treat you to something nice. I think the King of Gotham deserves a little something for being so kind and generous to a poor little waif like me."

"Poor little waif." He repeats with a squawking guffaw. "You're too cruel for such a title. Besides, don't waste my money on me. Treat yourself and show the world that Oswald Cobbelpot knows how to keep his little bird sweet."

Dropping your hand to his crotch, you roughly cup at the heft of his bulge through his slacks.

"I wasn't talking about money." You growl into his ear and a satisfying delight washes through your overheated body as he visibly shivers in response to your unspoken promise of a much more physical treat later in the evening

[humanplaypretend]

have some more of these bc it's all I can do lately

[manny-hughez]

Nygmobblepot from TWO FUCKING YEARS AGO. Where is this energy now… 2022 me where did you go. 😭😭😭

[philosopherking1887]

Rating: M

Ships: Oswald Cobblepot/Edward Nygma (endgame); Oswald Cobblepot/Jim Gordon (temporary but substantial)

Fic summary: Jim and Oswald agree that the relationship between Edward Nygma and Lee Thompkins is a disaster waiting to happen, so they come up with a desperate plan: plant evidence that they're having a secret affair to spark jealousy in Ed and Lee and draw them away from each other. Their plan is both complicated and helped along by simultaneous crises involving the brothers Valeska…

Chapter summary: Having drawn a confession from Oswald, Edward makes a confession of his own about the significance of a particular song, and they go to bed together.

Here it is: Sex Chapter Part II, a.k.a. Ed finally gets off (after some more delays for conversation).

And now all that's left is an epilogue. Seriously, that's it. No more increases to the chapter count.

[keffirinne]

Masterlist

Series:

🔥 Better call Saul:

Let's have some fun / Lalo Salamanca x Reader / WIP, smut

1 | 2 | 3 | 4 | 5 | 6 | 7 | 8

💎 Birds of Prey:

Please not him / Roman Sionis x Reader / smut, completed

1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 |

You would look good in red / Victor Zsasz x OC / WIP, smut, angst

1 | 2 | 3 | 4 | 5 | 6 |

🐧 Gotham:

Don't lose control / Oswald Cobblepot x Reader / smut, on hold

1 | 2 | 3 |

Oneshots/Requests:

Learn some patience, Sionis / Roman Sionis x YN

Bad dream / Roman Sionis x YN

Overprotective!Roman Sionis / Roman Sionis x YN

Feel free to ask me anything! Always happy to talk to you guys 🌸

[ccalhoun]

hey can you do relationship hc for oswald cobblepot (sfw/nsfw) with a male or gn reader

thanks!

≻ ┄┄ ♡ ┄┄ ≺

oswald cobblepot/the penguin x m!reader headcanons!

warnings: amab/male reader, switch reader, switch oswald, russian oswald, penetration, praise kink, blowjobs/handjobs, short sorry

wc: 600+

note: erm ignore how this took almost a year bye

cut for length!

sfw;

☆ - knows he can be snappy at times so he makes up for it by lots of apologizing if gets mad at you, as well as flowers and an expensive dinner <3 

☆ - various petnames, some in english some in russian. he loves his native language and thinks calling you russian petnames is the best thing in the world. his favorites are лапушечка (darling), умняшка* (clever/smart), солнышко (sun/sunshine)

☆ - he adores how smart you are. it doesn't matter if you're not a genius and just know common knowledge, he's in love you and your mind and could listen to you talk about anything for hours

☆ - secretly a cuddlebug. he always want to be touching you even if small ways, in public he'll always want to be sitting next to you. and in private, he'll always wants hugs. if you two move in (which he heavily wants), cuddles, every night. he doesn't mind any cuddling position, i really dont think he has a preference. he just wants to be close to you.

☆ - can and will show up to your house uninvited just to say hi

☆ - wants you to move in with him or buy a house for the two of you to live in. he has the money, he doesn't get why you won't let him. if you do cave and say yes, he'll look at every house available and show you all of them, requesting a walk through for the two of you and everything. he wants the house to be perfect for the both of you, and he won't accept anything but perfect.

☆ - very protective of you, would do anything you asked him. he doesn't want anyone to be rude to you, so what if your coworker who was yelling at you was found dead within a few days? it couldve been anything...

☆ - loves kissing you. forehead kisses, cheek kisses, normal kisses, he just wants to kiss you :(

☆ - kind of very clingy. just always wants to be around you. it doesn't matter what you're doing, he'll try his hardest to find a way to go with you. you have to do paperwork? he'll sit in your office with you. you have to cook? he doesn't mind waiting. you have to clean your house and do chores? he'll help! there's really no way to avoid him.

nsfw;

☆ - a switch, obviously.

☆ - doesn't mind being a dom or sub, but it would definitely take awhile for him to warm up to the idea of penetration either ways.

☆ - i hc that he's a virgin when you start dating LOL. u can not tell me that man fucks

☆ - loves hand stuff and oral! horrified of going all the way.

☆ - i think he would probably have to be really close to you and have to wear/make you wear protection for penetration. he's a bit of a germaphobe and just doesn't think its very cleanly.

☆ - after awhile and he's more comfortable with it though, it's over for you. he can go hard either way, one day he wants to be completely under your control and the next day maybe he wants to boss you around and take control over you, it really just depends on how he's feeling!

☆ - i also heavily hc that he has a praise kink, he wants to be praised and he wants to praise you. he turns into putty and basically gets hearts in his eyes whenever you tell him he's doing a good job or he's being a good boy. but on the other side of things, he also wants you to know how much he loves you. like i said before he really likes complimenting how smart you are, so expect him to praise you over every little thing you do!!!

☆ - probably wants to hold your hand while fucking lol, will basically beg to hold your hand if he has to.

≻ ┄┄ ♡ ┄┄ ≺

[adalwolfgang]

ADAL!!! saw your requests/inbox is open…and i had to send in a little something something!!!

heard you do “i ship you with…” so i was wondering what gotham character you might ship me with!!!

As far as physical appearance goes, I’m a 4’11 cis female with long brown hair and brown eyes, tan skin, hispanic, and wear a lot of black and red :> (and wearing glasses when im not in my contacts sksksk)

As far as personality goes, I’m a little eccentric, lots of jokes teehee, my MBTI is INTP, aquarius zodiac sign, and I love a possessive jealous protective man 🤞 I’m bisexual with a preference for men, and my ideal date idea is a movie at home !! or a grocery store date (i love shopping!!)

tysm adal ^_^ u dont have to if you dont want too, or if you dont do these anymore!! Just thought it might be fun !!

A/N: AHHH YES!! I wont ever stop doing these so you're good! Also sorry for the wait! Im trying to get through asks today because the numbers are starting to stack up and I don't want to keep holding it off anymore! But my inbox will always be open!

I ship you with...

Oswald Cobblepot!

Let's start with the height difference.

He loves it.

A lot.

Almost everyone he's ever encountered is always taller than him, or his height is used against him.

Definitely has a sort of power kink toward it if yk what I mean.

Now onto your color scheme.

We've all seen his many outfits throughout episodes and how fashionable he is.

He'll spoil you to your hearts content on whatever you want.

Including clothes.

There's a black and red outfit you've been wanting from a store down the street?

It's sitting on your bed by the next hour or so with a little love note attached to it.

If he's feeling it, you'll both be matching that day, wearing the similar black and red that you love so much.

He'll also make sure you always have a spare set of glasses or contacts on hand.

Just incase yk?

If anyone dares to even tease you about your clothes, glasses, looks in general?

Dead.

I can't stress the 'anyone' enough.

He knows what it's like being talked down to and mocked so he isn't having non of that when it comes to you.

He doesn't want his darling going through the same shit he went through.

He's gonna do whatever it takes to make you live the best.

As a queen.

His queen.

He's not the best at telling jokes but he does have a certain sense of humor.

Like laughing at the people, who've hurt either him or you, who are on the ground screaming in pain.

Again, a certain sense of humor.

Lets say you try a harmless prank on him, and end up scaring the shit out of him.

He'll scold you but is smiling by the end of it.

If you tell him a joke, he'll laugh at it.

While also staring at you with a loving gaze.

Back to him loving to spoil you, he much prefers taking you out to extravagant places for a ideal date like a fancy restaurant but won't mind just chilling at his mansion and snuggling up on the couch with you.

He doesn't get the whole shopping dates you mention though.

Why do something like that when he can just make others do it for you?

If you beg for it enough, he'll agree.

But he makes sure zsasz and a couple other of his men come along.

Again just in case.

He'll tell them to spread out and not stick so close to you both so it can feel like it's just you and him having a nice bonding moment.

Don't expect him to carry anything though.

Poor Zsasz we'll probably get stuck acting as some pack mule.

[too-much-heaven-on-his-mind]

I wanna cry, how do I explain that I ship Oswald and The Riddler MORE than I ship Oswald and Edward 😭

LIKE, I'm gonna have to write a fanfic just to make my point because AO3 doesn't understand me when I try to look for a Oswald/Riddler with Jealous Ed on the background fic 😭😭😭😭😭😭😭

PLEASE IF ANYONE KNOWS ABOUT A FIC LIKE THAT PLEEEEEASEEE SEND THE LINK, I CANT- I CAN'T FIND ANY AND I'M CRYING RIGHT NOW I NEED IT 😭😭😭😭 I'M STARVING PLEASE

[mysticalarmand]

Barbara: Ed likes being pegged, prove me wrong

Oswald: I can confirm

Isabella: Can confirm

Lee: Can confirm

Kristen: Can confirm

Barbara: I'm not surprised he takes the strap

[it-happened-once-in-a-meme]

"Would You Still Love Me If I Was a Worm?" Questions Gotham Couples/Friends Ask Each Other

(In honor of Valentine's Day 🥰💞)

Oswald to Ed: Would you still love me if I was a worm?

Jim to Harvey: Would you eat me if I was turned into a donut for forever? 😂🍩

Selina to Bruce: Would you still be interested in me if I had no cool stuff to teach you?

Tabitha to Butch: Would you...be so kind as to let Barbara stay with us?

[philosopherking1887]

Rating: M

Ships: Oswald Cobblepot/Edward Nygma (endgame); Oswald Cobblepot/Jim Gordon (temporary but substantial)

Fic summary: Jim and Oswald agree that the relationship between Edward Nygma and Lee Thompkins is a disaster waiting to happen, so they come up with a desperate plan: plant evidence that they're having a secret affair to spark jealousy in Ed and Lee and draw them away from each other. Their plan is both complicated and helped along by simultaneous crises involving the brothers Valeska…

Chapter 23 (of 24): No Man's Land. Gotham has been cut off from the mainland and descended into near-anarchy, save for a few pockets of order and relative safety -- most importantly, the Green Zone, where Jim Gordon leads the ragged remnants of the GCPD in protecting a few hundred stranded civilians; and the territory that Penguin rules from his fortified citadel in City Hall and protects by controlling the city's ammunition supply. Running out of ammunition and food, and losing his tenuous hold on order in the Green Zone, Jim takes a desperate risk and goes to Penguin to propose an alliance.

LOL, did I say "no more increases to the chapter count" when I posted the last chapter? Well, I lied. Again. Because what was supposed to be a short epilogue turned out not to be that. And it was getting so long that I decided it would make sense to split it into two chapters (and there was actually a decent place to do that, fortunately). So here's Epilogue-ish-thing Part I.