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#Riddler
jackmustcry · 2 days
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a 2025 riddler (please do not feel the need to tell me you do not think he looks like Paul Dano)
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ridstler · 2 days
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snazzy
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lasagnebats · 1 day
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found out The Riddler was first introduced in 1948, so i thought it would be fun to draw him in fashion inspired from that era. he probably says "dapper" and "chap" a lot
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nahla-art · 3 days
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Suddenly, Oswald felt a sharp sting on his bottom lip, and Edward pulled away immediately. In the mess of the moment, Edward had bit him, and his bottom lip bled. 
“ I’m— I'm sorry, I uh,” Edward panicked and awkwardly used his thumb to wipe off the blood, “ I’m so so sorry.” 
“ Do that again.” 
“ What?” 
Oswald held the back of his neck, pulling him close, “ Again, please .” 
Edward nervously tapped over Oswald’s thigh before boldly, hungrily, closing the distance between. Edward did make a small hole in the lining of his pants, over his inner thigh. Oswald dug his thumb through it and pressed onto the warm skin underneath, widening the hole. As a result, Edward moaned deeply, and Oswald took the chance to lick into his mouth. 
( The Penguin and The Peacock, chapter 8 )
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finzphoenix · 2 days
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A certain scene from the fanfiction Cat & Mouse, written by the lovely @caesariawritesstuff who also happens to be the one who commissioned this wee thingy. If Riddler/reader is your cup of tea, do check out their fic, it makes for an fantastic read! 🖤🤍
OC (c) caesariawritesstuff
Art (c) Finzphoenix
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finniestoncrane · 3 days
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Almost There
Capullo!Riddler x Fem!Reader, word count: 4k commission: eddie desperately trying to get someone to like him, but failing a bit miserably before he starts succeeding, as he was always bound to 💚 commission me here! request info • prompt list • send me a request • kofi • masterlist minors DNI!! 🔞 cw: whiny/desperate eddie, teensy bit of angst
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With a sigh of resignation, Eddie looked out of his window on to the streets of Gotham below. People, like ants, below the feet of a God they didn’t even know they worshipped yet. But he could take very little joy in that usually comforting fact, as he knew there was one ant of great subordination who refused to bend to his will. And that was despite knowing everything he could offer them in exchange for their undying and unquestioning devotion.
No amount of anything he had would fix this situation. This was him now. He was stuck. Edward Nygma. Stuck. Stuck on a puzzle, on a question, on a task, for which there seemed to be no possible outcome for. Or at least, not one that he deemed reasonable, not one that he would be happy with. Which, after all, in the mind of the Riddler, was not the correct answer at all.
The phone he clutched in his hand was quickly tossed onto the nearest surface. It was just a hopeless distraction at this point. A symbol of futility. Of his seeming failure.
Eddie’s fingers were getting tangled in his fringe. The greasy strands of his usually neatly swept back shock of red hair were getting caught as he twisted and pulled at them. Teasing at them nervously, he paced around his pre-furnished, and entirely impersonal, apartment. Looking at the extravagant wall clock he sighed and groaned, letting it form a soft growl as he ripped a few extra strands of his hair out in his closed and trembling fists. He was thankful for the thick, soundproof walls in this building. It meant he could talk, or groan, or yell, to himself as loudly as he wanted without fear of anyone hearing his plans. Or his pathetic whining.
“How long does it take someone to answer a text? Is she really that stupid? And if she’s that dull and so incapable of typing a message out, do I really want to be associated with her?”
His self-serving insults regarding your intelligence only helped to make him feel worse about himself. You were perfect. Beautiful, but in a way he’d never really seen before. Interesting, more so than any other woman he’d bothered giving the time of day or willingly chose to get to know. And you weren’t stupid. In fact, you seemed scarily competent and able to hold your own against him. Which he hated.
Another thirty seconds of anxious pacing, as he wondered what could possibly keep someone busy for this long. It wasn’t as if you could have anything important to do. Or anything more important than responding to his message. You weren’t him, after all. He was the busy one, the important one, the mastermind genius that had barely had time to focus on anything but himself. What could possibly be distracting you?
With a finger raised almost comically in the air, one floating light bulb short of looking like a caricature, Eddie shouted out.
“Unless! Unless… she’s really not as stupid as I thought. And… all this… is a clever ploy! Oh! Oh-ho-ho! That is… well, that’s frankly almost brilliant. I hate to admit it, but credit where credit is due, I suppose.”
He picked up his phone from where he had tossed it, laying on the polished marble surface of the sideboard he hated so much but refused to give up, as he’d been assured by the realtor that it was something a woman would appreciate. And of course “a handsome bachelor such as himself would definitely be looking to entice a woman”. He was glad that realtor was dead.
Gripping the soft velvet on the back of the sofa, he leapt over it, landing with a thud with his legs up on the cushions, head leaning back on the soft pillows as his red hair spread messily behind him. And he held his phone steadily in his hands, trying hard to exude confidence, even falsified, just to give himself something to cling to.
Behind him, the large, floor to ceiling windows gave view of the sunset, which was slowly stealing the remaining light from Gotham and sinking it once again into complete, dangerous darkness. And as that beautiful sight disappeared, wasted entirely on Eddie, he typed a quick message out, one that he felt sounded casual, despite it being agonised over in his hyperactive mind.
“Hey, you get my text? Maybe you missed it. Maybe you missed it on purpose. I’m on to you, baby ;)”
He paused for a moment, reading over the words on the screen with a twisted expression of disgust.
“Hm… maybe not baby… at least not yet.”
Deleting the final word, he read the text again. And then again. And then once more, before he decided to delete the whole thing. Throwing his phone to the floor with an exasperated grunt, he realised that you might have been watching his little ellipses, the telling dots that screamed “HERE COMES EDDIE! TYPING ANOTHER MESSAGE! LOOK HOW DESPERATE HE IS!”
Up until recently, everything had been going exactly his way. He’d scammed his bosses, embezzled expertly from the company that owed him everything and had until that point given him nothing, and bought himself a luxurious and ridiculous apartment that he had wild dreams of turning into a bachelor pad, with endless parties that revitalised every night with new guests and new drinks and new experiences. Money hadn’t quite been enough to buy him the necessary friends or women, however. Although, when he thought about it, technically his money had bought him the company of several pleasant enough women. But it felt like an offence to him that he had to pay for their services, to beg, essentially, for their affections, and then had to add on an extra few if he wanted to have them pretend to listen to him as he talked to them. By his calculations, women should have been falling for him. They should have been paying him for the opportunity to be talked at. He was Edward Nygma! He was intelligent, he was handsome, and now, he was wealthy.
Realistically, there was an obvious solution here. And an easy one at that. He could go out, flash some cash, and find the first suitably pretty girl who reacted positively to his shtick or his flaunted wealth and take her home. But that routine had gotten old, it felt like those cheap sudoku puzzle books you could buy at the corner store. Easy, too easy. Though he might be loathe to admit that to anyone, given that he felt it was part of his reputation, his lore, his borderline misogynistic use of woman as a status symbol as an essential aspect of his character by this point. In his illusions of grandeur, and his misinformed concept that everyone knew who he was, he felt like everyone knew that about him, this staple of his personality, especially the girls at the clubs he frequented when his loneliness became intolerable. What Eddie wanted in a woman reflected his desires for the entirety of Gotham, and eventually the world. He wanted immediate adoration with nothing in return. An endless willingness to please him. And key, above all: subservience. Complete and utter subservience.
So why was he all of the sudden chasing someone who refused to give him the time of day? Who couldn’t even reply to a text with due diligence? He mused out loud, pondering this interesting conundrum, before he spoke his assumed answer.
“The… challenge? Maybe?”
As he spoke the answer to his empty apartment, he realised the confusion within him. One part of him knew the answer, the other too stubborn to learn it or accept it. He supposed it was the right answer though. It made sense, after all. Everything had been too easy lately. Very little ever posed a threat or a challenge to him anymore. And life had, unfortunately, become boring. Perhaps the fact that his plans and dreams were falling into his lap made him question whether or not he was actually achieving anything. This one act, going against the grain, against everything that he was, and wanted, to his core, felt like the first time he had actually engage his brain in something. And that was good practice, because sure enough, when his greater plans were in motion, he would have to be well-versed in thinking on his feet. Especially if he wanted to outwit the GCPD and his future, pointy-eared nemesis.
And of course, besides all of that, he was Edward Nygma. There wasn’t a puzzle he couldn’t solve, no challenge he couldn’t eventually meet. The last thing he was going to do was let some ungrateful woman get him down. No way. Even if it took all of his determination and might, and every ounce of his brain power, which as previously concluded was not really up to much else at the moment, he would have you.
With a renewed, and somewhat misplaced, sense of confidence in his abilities, something he found hard to admit had even been diminished in the first place by your ridiculous behaviour, Eddie typed a simple message. Admiring it before sending it as though it were a piece of minimalistic art. A masterpiece. One to be looked on by the ages.
“Hey.”
That was enough. And quite frankly, it was all you deserved right now after your negligence and rude behaviour. He would let you come running to him. Let you get intrigued by his casual interest. You could – no­ – you would come to him. As he sat, grinning smugly at his self-congratulatory pride, his phone pinged. The small chime was enough to make him jump, his heart thumping as it missed a beat, a strange sense of arousal that surged through him at the mere suggestion of you paying a tiny iota of attention to him. And as he picked up his phone, he muttered to himself.
“A response already! See, Nygma, you know what you’re doing.”
Looking at the screen of his phone, his grin was immediately forced down by the immense emotional gravity into a large, comical frown, his brows scowling as he read the brief message you had decided to grace him with.
“What do you want?”
Seething, and through gritted teeth, Edward hissed into the empty apartment.
“Oh, you little…”
He managed o stop himself before he said something even he might have regretted. But still, enraged by your lack of interesting and your crude wording, Eddie felt his fingers tense around his phone painfully. Any more pressure, or strength in his slender body, and he may have cracked the device in half. Relaxing his digits, he typed a quick message in response, pleased with himself, but still deeply upset with yours. If that’s how you wanted to play it, then you could get ready to be met with a formidable opponent.
“Sorry, might be the wrong number. I have two girls’ numbers in my phone right now without names yet… which one are you?”
That would show you. False competition for his attention might engage you better. If you thought there was even the most slender, most remote chance, that you might not get to be with him, then it might encourage you to a little bit more receptive. Or at least, slightly more polite. But your response, coming incredibly quick, only served to snuff out that idea.
“I’m the one you should delete and block.”
“Fuck!”
Eddie tossed the phone once more, letting it land with a thud on the soft carpet on the floor as he rolled over on the sofa, burying his head in the cushions and letting out a variety of grunts and groans, though mostly mewling and pathetic whimpers. After a suitable amount of time spent feeling sorry for himself, and trying to convince his own ego that the backfiring of that particular approach was down to your difficult personality, he rolled back over. Staring blankly at the ceiling, he tugged nervously at his hair again as he tried to reason with the silence.
“Come on, Nygma. Solve the puzzle. She’s a Rubik’s cube, and you need to get your fingers all over her, twist her the right way until she makes sense.”
With an exasperated sigh, he reached to the floor and picked up his phone. There was a chance, he thought, that being himself might, for the first time ever, work when dealing with a woman. After all, it was foolish to keep trying the same methods and approaches, madness to think it might yield different results. Something completely different, something out of left field. A shock factor. It might just be the thing to loosen you up.
“Perhaps…”
Delighting in the idea that perhaps he was the solution to the puzzle after all, he typed out a new message. Very flirty, very cheeky, and typically Eddie all over.
“Oh!  It’s you. I’d recognise that attitude anywhere. Spicy. Off-putting. I won’t be deleting you, so what do you want your name to be in my contacts? Would ‘babe’ do?”
You were typing already. Hook, line and sinker. He had you, and even if you were only replying in order to tell him off, at least you were communicating with him. It was better than nothing. And it meant he might have another chance before you decided to block him.
“Absolutely not.”
“Ok then. What about ‘cutie’?”
“If you think ‘cutie’ suits me, then I think you still have my identity mistake.”
“Ok, fine then. If we’re going for descriptive accuracy, how would ‘Stone Cold Bitch From Hell’ suit you?”
The back and forth stopped. There was no immediate response from you, and panic began to settle in Eddie’s chest. If this backfired, it would take a lot to come back from it, effort he wasn’t sure he was ready to put into even a committed relationship let alone a hook-up with someone he barely knew. Even he might not be able to rescue this situation from the hole he had dug for it. Maybe, he should have clarified it was a joke. Text you back immediately with a smile and a laughing emoji. After all, not everyone was as intelligent as he was, and the nuances of his humour did often go unrecognised or misconstrued, through no fault of his own obviously.
When his phone finally pinged, Eddie held his breath as he looked at the screen, his skin dimpling and his hairs standing on edge as he waited for the disastrous consequences of his actions to rear their ugly head.
“Actually, that one kind of suits me. Maybe you’re a bit more perceptive than I thought you were. And don’t get excited, because that really isn’t saying a lot.”
With a smug grin washing over his face, Eddie elected not to respond any further than sending you one solitary winking face. That would do, for now. He had to take it slowly, even still. Weeks of pandering to you, of trying to be someone else. And now, finally, he found out that you were one of the rare few who responded positively to his true self. A woman of refined taste, it seemed. But he was still wary, cautious.
As he got himself ready for bed, he thought back on how much time he had wasted so far on you, trying to convince you that he was perfect for you from behind a façade that you clearly had no interest in. He’d learnt the lesson, yet again, the hard way. Be himself.
“Be yourself, Eddie. That’s how you’ve won everything you have so far in life. Who can resist your charms? I mean, come on!”
He grinned wide into the mirror above the sink, shooting himself a quick wink, sly smile spreading further. He brushed his teeth quickly, spitting into the basin before focusing his attentions back on his reflection, picking at his teeth and combing back his hair before stopping to pose in front of the mirror. He flexed his almost non-existent muscles, self-obsession and illusions of grandeur once again assuring him he had the body of an Adonis, and then he laughed.
“I am genuinely almost jealous of her. She gets to be with this! Hoe wonderful for her. I truly am a gift.”
Thoroughly enamoured with himself, he took his self-satisfaction and headed to his bed to celebrate it in the disgustingly lewd way only he could. And, surprisingly, beyond the thoughts of how wonderful he was, he was thinking of you as he congratulated himself over, and over again.
And he was still thinking of you in the morning when he woke up. It had been a long time, concerningly so, since someone other than himself, or that ridiculous vigilante with his tight-fitting costume and penchant for leather, had been able to steal the focus of his attention. The excitement at the novelty of the situation had him giddy as he got out of bed. Purposefully ignoring the pull of desire to check his phone for any notifications, he opted to primp and preen first. The longer he held off checking, the longer he could live in ignorant bliss of the true, and potentially heartbreaking, outcome.
“Schrödinger’s booty call…”
He winced at his own joke, the thought of it distressing him. What if that’s all he could get out of you, in the end, after all of this?
“OK, but do I really want more?”
Yes was the answer to that, although his empty apartment could hardly scream that back at him. This was beyond a quickie, a one-night stand with someone he found physically enticing. He had deeper feelings for you, maybe only slightly underneath his callous and crude surface. But they were definitely there. What they might amount to in the future even he couldn’t be sure of yet. But all he knew was that once with you would not be enough. Not for the trouble he considered himself having gone through for you.
Finally dressed and smothered in his obnoxious cologne, Eddie turned his attentions back to his bedroom as he left the ensuite to find out whether he had a reason to live this morning. And if you hadn’t replied, his plans to destroy Gotham would be enacted far sooner, spurred on by your cruelty.
Luckily, however, for the citizens of Gotham and Eddies own ego, given that with so little preparation he was sure to fall flat on his face if he commenced his grand scheme so early, he had one message and it was from you.
“Nygma. That’s right, consider yourself lucky that I remembered your name. You’re good with computers, yes? I seem to recall you bragging about it.”
“Ha ha! I’ve got you now!”
A typical ploy! How many times had he asked for help from someone, which he never needed given he was the smartest and most competent person who had ever lived, just to get closer to them or to spend time with them? Far too many for him to count. He was very aware of what you were trying to do. And he was more than happy to play ignorant, to play along and give you what you so clearly wanted.
On the edge of his seat, quite literally he realised as he shuffled back into the centre of his bed, his fingers tapped quickly, furiously, as he replied to your message.
“Obviously, of course I am. It’s kind of my thing. Although, you obviously knew that.”
Was he too smug? Maybe… But you clearly liked him. It was impossible for you to deny it now. It was only a matter of time before he lured you into his web and kept you there… willingly of course… unless…
Eddie’s more villainous daydream was cut short, thankfully, by the slight vibration of his phone against his palm, a tingle sent through him like an electric shock as he took a breath and looked to his screen, or looked to his future.
“Great. Is this guy any good? I need someone to fix my laptop and he looks competent.”
Attached to your words was a screenshot of some less man, the Computer King he was calling himself, who was offering extortionate prices for no doubt shoddy, subpar work, regardless of what it was that you needed.
Were you joking? He couldn’t be sure. It could be an effort to make him jealous, retaliation for his own efforts the night before. It felt as though you were goading him into offering himself up on a platter, detailing his skills and positive attributes like you were interviewing him for the job of “gracious boyfriend”. And that just wouldn’t stand, not even…
“It would stand though. Only for her. But still, irritatingly so…”
Laying back in his bed with a soft thump, he clutched the phone to his chest, reminiscent of how he had been the night before, and so many other moments leading up to this one. You were in his head, and he could feel you slipping into every other facet of his being. But still, he was slightly pissed off with your constant back and forth, your cold attitude, flaunting the concept of communication in front of him and then snatching it away cruelly with the suggestion that you’d be giving it to some other, lesser, man.
Fed up, and already annoyed at this early hour, he typed a droll message.
“Yep. He’d be good enough for you, anyway.”
With a falsified grin that faded into a genuinely emotional frown, he placed his phone down and went to the kitchen to grab some coffee. He managed to convince himself he’d done the right thing. Pretending to be proud of himself, he sipped slowly, a dramatic “ah” at the end of each slurp as he continued the farce. Who he was performing to, he wasn’t even sure himself. But given that he spent most of his time in solitary isolation, self-congratulatory arrogance with the aim of tricking himself into feeling comfortable was the least strange thing he did alone.
When he realised he hadn’t heard his phone chime, though, he began to feel tense and nervous. He was fidgeting, tapping the edge of his coffee mug with his fingers, shaking his leg, his foot bouncing on the ledge of the breakfast bar. One moment of, albeit in his mind rightfully placed, anger, and he’d undone his weeks of hard work.
“Idiot, idiot, idiot.”
In a rare moment of self-reflection that bordered on a breakthrough, Eddie considered his life as a whole, and how many things had actually gone right for him. The years of slaving away at a job that didn’t respect or value him, his tortuous formative years filled with bullying and excommunication from every social group he had tried to enter, his lack of luck in social situations with anyone he dared to interact with, his formidable and deeply unloving parents. The possible, but likely inevitable, end to his great schemes when the vigilante of Gotham decided to crack down on him. Surely, all of these amounted to an understanding that Eddie might just not be lucky, or made for good fortune. Or, could it be that Eddie was the problem? That he was the common denominator in all of the unfortunate things in his life?
It was a self-hating thread that he rarely pulled, for fear that his entire existence would become unravelled. But then, a glimmer of hope as he heard the chime, finally.
Tripping over himself in a bid to reach the phone as quickly as possible, he read the message wide-eyed and hopefully.
“I don’t want to regret this, Eddie. You seem to not understand. If I get another guy to look at my laptop for me, then I can meet you for a coffee while he works on it. You seem like you might be adequate entertainment for an hour. And besides, I feel like hating myself today. So?”
Eddie’s wide smirk pressed into his cheeks as he sighed dreamily. With any luck, you’d be willing to commit to hating yourself every day if he could just make sure this date went well. And since he had already managed to get this far with you, he assumed his natural charms would see him the rest of the way.
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oxygen-stealer · 9 hours
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Guess what fixation has come back and hit me like a truck
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carduelism · 2 days
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riddletoxin · 2 days
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Again, apologies for the delay. This is the city setup for chapter thirteen on. (https://archiveofourown.org/works/53119303) The reason for using this map is simply because it's the one I'm most accustomed to (Arkham Games !!).
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unknown-art-room1 · 3 days
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When you get your hair dyed green and purple, only for it to start turning blue a little over a week later. When in Gotham, the only person who has the same shade of blue is to blame... Nightwing.
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jackmustcry · 2 days
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some bigger riddlebat art
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ridstler · 13 hours
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shootthfckp · 16 hours
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best, you've got to be the best
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thesuperheroesnetwork · 7 months
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Texts From Superheroes
Facebook | Twitter | Patreon | Instagram
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mylifeingotham · 4 months
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