#riddler imagines

You curled up on yourself, hugging your knees to your chest as you hunched uncomfortably, head ducked low. Despite the blanket bundled up around you, you were freezing and desperately wishing the radiator would kick on to heat the drafty room. It was dark, all the lights off, and you had been alone for far longer than you would have like to endure.

As if by fate, there came the sound of keys jingling in the door’s lock, and you craned you neck to look. The deadbolt shifted loudly, the door knob turned, and silhouetted against the light of the apartment hallway was a bulkily dressed man.

He strode in, locking the door behind him and tossing his apartment keys on the side table near the entrance. He didn’t bother to kick off his tactical boots, and they thudded against the dusty floorboard. He walked into the next room where you sat, a pitiful sight.

Your eyes lifted to meet the ones behind clear framed glasses, and you perked up slightly, attention completely on him. Edward.

He had the soft, round face of someone entirely unassuming, looking sweet even. Though, you knew first hand what sort of dark secrets and twisted intellect resided in that brain of his. Regardless, you felt a wave of relief as he entered, glancing to the corner of the room where your cage was, a small smile forming on his lips.

“Look at you,” he cooed. It would have been condescending if he didn’t look so pleased to see you. He approached, boots heavy with every footfall, and reached a hand between the bars of the cage to stroke your hair tenderly. “Are you happy I’m home, sweetheart?”

You nodded, eyes flitting to where his other hand clutched a plastic bag at his side. He followed your gaze, and withdrew his hand. “Just some supplies,” he explained, reading the question in your expression. “For next time.” You didn’t have to wonder what ‘next time’ meant—all you had to do was look on the news to know that everyone was clamoring about when and where the next Riddler attack would take place.

They called him a radical extremist, an urban terrorist preying over Gotham…but you knew him for who he really was: a visionary, serving justice and pointing a light at the corruption that plagued the city. And, more than that, he was your Edward—brilliant and soft-spoken, and utterly devoted to you.

Edward reached a hand down to unlock the latches of your cage, stepping back so you could crawl out and stretch the limbs that had been cramped for too long. “Sorry I’m home late,” Edward apologized. “There was a shooting at one of the downtown stops—it delayed the whole subway schedule.” He set his bag of goodies on the cluttered coffee table, before turning to walk towards his computer set up.

“We’ll have to eat dinner after the stream,” he hummed, contrite. “It’s scheduled for 8:00pm.” You rose to your feet slowly to follow after him, wanting to be close after being separated for so long. You kneeled down next to his chair so you could rest your head in his lap, and he lowered a hand to stroke you as his other clicked away.

After a few more minutes of clicking and typing, Edward had logged onto his secure, encrypted website. The whole process honestly confused the hell out of you, and it only made you respect him all the more for knowing the ins and outs of computer science and hacking. He really was a genius, and the reminder never ceased to make you swell with pride for being his and vice versa.

Edward rose from the chair, walking to the side of the room to dress into his infamous garb. You watched him don the mask so many dreaded and feared—the face behind the movement, which reaped violence against the rats of the city. All of it Edward had symbolically designed, meticulously orchestrated, and filmed for all to see.

As he strapped in and covered up all of his identifiable features, you saw his figure bulk up with the layered fabric and leather. More so, you saw the shift in him that never ceased to amaze you—Edward was set aside now, and the Riddler had come out to play.

He reached a glove towards you, and you stood still while his hands gently maneuvered a little black, lacey mask over your face. He felt it necessary to protect your identity as well, seeing as you were now an extension of him, his sweetheart. He would always take care of you; always make sure you were safe and looked after.

The Riddler patted your head, before stalking past you to sit back down at his computer chair. You laid nearby, languidly stretching your body along the couch, sighing contentedly as you watched him work. He set up the camera, clicked a few more buttons, and soon the red light had flickered on.

“Greetings, everyone,” his voice garbled out, the voice modulator making him sound deeper and more frightening than the man who usually spoke so softly to you. “I’ve got something real special for you tonight. Something they didn’t want you to see.”

You listened as the Riddler began his manic diatribes, informing his loyal followers of the latest updates. Eventually, growing bored, you tuned him out, deciding to leaf through the latest book he’d brought you: The Shock Doctrine by Naomi Klein.

Around an hour had passed as you went about your nightly routine, the deep sound of his voice lending a pleasant ambience to your reading. Then, startling you from your book, you heard that intimidating voice—comforting and familiar—call your name.

You glanced up quickly, looking at him. The red light was still on, the stream ongoing, and yet he had his chair turned to look at you. The blue glow of the monitors cast him in a rim light, though the lenses of his glasses seemed to glow as it reflected back. Raising a hand, he crooked his finger at you, silently beckoning you over.

You marked your page and set your book aside, obediently rising from the couch and walking over to him. As you approached, you could see the chat on the side of the screen receiving new messages, the viewers evidently delighted by your appearance.

Jus$tice_anycost: she’s finally back on stream! Thought the system got her lolz XD Eyeswideopen98: She looks so pretty in her new mask omg o///o WakeUpG0th@m: Yo, he’s got a girl?? I’m new /srs Eyeswideopen98: @ WakeUpG0th@m yea, she gets the mission, she’s chill Riddlemesaved: not the only thing she ‘gets’ ;) Rattrapsss: ngl, sometimes I like her voice more than his LOL Riddlemesaved: fuck, those tits always get me…

The Riddler turned his head to read, his hands absent-mindedly trailing your thighs and your ass. There never was a need for him to ask your permission. You were happy to service the one you loved whenever he desired your touch.

His eyes seemed to shine with delight as the waves of compliments rolled your way. He thought his devoted followers were so lucky to see your luminous beauty. “You’ve got fans,” he spoke lowly, the sound growling out of the modulator. His traveling hands dipped into your waist band, and he pulled your shorts down without much warning or fanfare. “C’mere.”

You let him pull you into his lap, your ass planted on one thigh as he helped hook your legs around the armrests. Spread open now for the blinking red camera light, you blushed a little, and gave the fans a bashful smile. His chest flush to your back, you heard his breath coming out heavy and hot through the holes in his mask.

Jus$tice_anycost: Damn look at that, her panties are already soaked… Riddlemesaved: @ Ju$tice_anycost, cause she’s always ready to be used xxx WakeUpG0th@m: Hooooly shit…

A small whine sounded in your throat as one of his hands wrapped around to rub against your clothed pussy. Two leather-covered fingers circled the wet fabric, a filthy sight. More messages flooded in, eager and lustful directed at the two of you.

“Isn’t she so beautiful?” came his throaty garbled voice behind you. “So good to me.”

Eyeswideopen98: She’s perfect for him… Rattrapsss: can we see??? <3

You sighed softly as he removed his hand from you, lifting the glove up to your face. He patted your cheek gently, before nudging the tip of the glove between your teeth. “Bite,” he ordered, and you obeyed. Slowly, you tugged the glove from his hand, revealing his fingers, thick and dexterous from all that typing. You opened your mouth, letting the glove fall limply to the floor.

His hand returned to your pussy, and gently it pulled the fabric of your panties aside to reveal your sex, bare and dripping with arousal. The Riddler glanced up to read the messages in the chat, before a throaty, dark chuckle vibrated against your back. “Guess we’ll be online for a little while longer,” he spoke, and then he pushed two digits into you knuckle-deep.

A soft, draw out moan left your lips as he gently fucked you with his fingers. You felt the leather of his mask press against your neck as he took in a deep, ragged breath. You could feel the firmness of his erection against your ass, poking you. You wiggled your ass against it slightly, feeling pent up and a little cheeky.

Your sweet Edward gasped at the feeling, and the sound made your heart flutter. But soon, the Riddler was placing a firm hand on your hip, the other fumbling with his belt as he struggled to undo the zipper and buttons there.

WakeUpG0th@m: fuck, this is so hot Eyeswideopen98: he’s the riddle, she’s the answer… Riddlemesaved: yesss, this is my favorite part…!

You felt his hot breath panting against the back of your neck as he freed his cock, and eagerly positioned himself up against you. With his back leaned against the chair, he lowered your hips down so he speared you onto him inch by inch. Your face screwed up with the intrusion, a small cry escaping you once he was fully hilted, the head of his cock nestled against your cervix.

His hand moved north to your chest, and he squeezed your breasts through your shirt. With a strangled groan, he began to move, rolling his hips up into you as he grinded against your ass. His cock was covered in your slick, the sight gleaming against the bright light of his set up.

“A-Ah,” you gasped, your hands clinging onto the armrests for dear life as he picked up the pace, hips snapping against you.

“Damn, you’re so fucking tight. So perfect for me,” he gritted out, pumping into you with enthusiastic zeal. He used you freely, and you loved every second of it. You tried to read the onslaught of comments popping in the chat, but you couldn’t make out more than a few words—you were too drunk on the feeling of his cock pistoning into you.

“Oh my god,” you drew the words out in a breathless moan, and you felt his hands flex into the dips of your hips.

“Yes,” he growled out. “I am your god.” His hips punctuated each syllable harshly, and you gasped at each thrust.

“Fuck, fuck, fuck!” you sobbed out as he fell into a wild frenzy, fucking into you so hard you were certain you would be sore later. But he was too intoxicating, moaning so deliciously in your ear, that your pleasure was building at an alarming rate.

“W-Wait, I…mmm, I-I’m—” you babbled out nonsensically, but he didn’t ease up his brutal pace. Your eyes screwed shut and you bit down on your bottom lip. The sound of his balls slapping against you tipped you over the edge—the pleasure was all too much.

You came with a cry, clear liquid squirting from you as it hit the edge of the desk and wetted his keyboard. Edward’s hand flew to your clit, rubbing furiously to extend your orgasm, sending droplets this way and that, making an utter mess of the chair and computer.

Within seconds he was pulling out to shoot pearlescent ropes of cum all over your skin, his climax ripping through him violently as he choked out a strained, muffled sound. You leaned your head back against his shoulder as he gently slapped his cock against your folds, spreading his cum around so that it mixed with your own juices.

Jus$tice_anycost: annnnnd im saving this one to my desktop folder… :P Riddlemesaved: guys I just came so fucking hard I thought I died for a sec Eyeswideopen98: otp (˚ ˃̣̣̥⌓˂̣̣̥  )づ♡

You felt your lover shift beneath you, hugging you to his chest as he leaned forward. His hand moved for the mouse, and he read the comments. His eyes crinkled slightly in what must have been a satisfied smile. “Thanks everyone for attending tonight’s meeting,” he spoke, his altered voice deep and content. “That’s all for now, so be sure to tune in next time for more info on our next rally.”

One night while you were working late with Lee, she ran to get coffee. Alone in the office, you turned on your radio and let your hair down for a bit. You were an assistant to Lee an tonight was inventory night. The both of you would be pulling an all-nighter to document every scalpel and pill, re-file cases as cold and so on. 

With a night full of administrative duties, you were both fading fast. So you forked over the cash and Lee went on the coffee run. 

Pushing at the window which had been painted shut a long time ago, it opened outward just enough for you to look below at the city streets. The radio hummed in the background, the offices of the precinct silent for the night. As you looked down and out the window, you saw taxis driving by, honking their horns relentlessly. People were shouting from far away and the lights were still bright against the late night sky. 

Walking across the room, you pulled a cigarette from the pocket of your jacket. Swaying your head to the music, you hummed along to the melody as you lit your bog and turned up the music. 

Embracing your few moments of freedom, you swayed and hummed to the music as you subconsciously dragged on your cigarette, listening to the notes of the music dripping like honey over the distant city noises. 

Edward stood and watched you all those nights ago. He watched your lips exhale the smoke and your lips purse, he focused on how your hair fell over your shoulders and back again as you move your body to the beats. Your long skirt swayed effortlessly between your legs and around your graceful feet. 

From that night on, he was captivated by you-everything about you. 

Every three or four days a letter awaited you at your desk outside the coroner’s office. It had been happening for about three weeks but you hadn’t told anyone-well, except Lee. She saw them every morning, she always got to work early.

They weren’t long, just a simple quote or a picture of a famous painting. It was always something of simple intrigue that made your day. Small notes tucked away in mini envelopes. Occasionally a heart adorned them, sometimes a dove an then sometimes nothing.

You still didn’t know who was sending them but that didn’t mean you wouldn’t keep looking.

You had suspected either Gordon or Nygma but eventually concluded it was neither. 

You were friendly and men tended to take that the wrong way. Always making the assumption you were a flirt, many of the men in blue had made advances. But you weren’t flirting. You were just being nice, making conversation. Gordon was the only officer you assumed capable of such a subtle and sweet act, but after much deliberation you decided you were incorrect.

Gordon was too smart to mistake your kindness, besides, you were close with Lee. Jim could be obtuse, but never on purpose. He wasn’t a deliberate fire starter.

You had hoped maybe Edward was behind it but eventually decided against it. 

When you started at the GCPD, you had instantly clicked with Ed. Seeing as you both worked closely on cases, a lot of time was spent in each other’s vicinity. You bantered back and forth, exchanging jokes and riddles. You loved spending time with him but he never made any kind of move or reference to the notes you were receiving anonymously. 

So, despite your hopes, you moved on with your little investigation and remained by Ed’s side as a loyal friend.

What you didn’t know was that every single day Edward was falling deeper and deeper in love with you.

He saw how all of the men looked at you. They admired you and could woo you, they could literally sweep you off your feet-him, not so much. He saw how you spoke with them, paying them attention and laughing at their jokes. Your smile was so relaxing and appeared with such ease.

The relationship between you both was effortless and he wouldn’t do anything to risk you. You’d complained about men and their unwanted advances before-he didn’t want to become another creep on that list. 

Everyday he worked with you he wanted to tell you how he felt, he wanted to scream it from the roof tops. But he felt he couldn’t compare. So he grinned and bared it, expressing his compassions anonymously and remaining by your side as a loyal companion. 

That loyalty was eventually tested.

After working late one night and locking up after Lee, you stumbled upon Edward Nygma, drenched in blood, pushing a body into his trunk.

You parked across the street from the precinct in order to avoid any awkward run-ins with flirty policemen. Crossing an alley you of course recognized Ed, but only by his appearance.

Already nervous, upon seeing you he became manic.

He didn't approach you instead try to convince you not to run, but never once inching closer to you.

You knew Ed. You trusted him. So you waited.

When you didn't argue he stammered on in your silence explaining how this was a dirty officer. He found him stalking women, five including you.

He had hurt one of them and Ed confronted him but all he did was try and hurt Edward.

So Edward killed him.

No, not the most rational thing. But this was Ed.

So you helped him in a haze.

“I-Is your place safe?” Your words were coming out quick, you weren’t even processing what you were saying. “We can go back to my place but people could see us-and oh God the blood, what if-”

“We can go to my apartment.” He gently silenced your rambling with his suggestion. “No one will see us, I’ll make sure.” His words were confident, his tone soft. He was scared for you. He couldn’t tell what you were thinking, of him, of yourself, your job or the law. He was in the dark as you silently rode back to his abode next to him. 

As he drove, you remained silent, processing everything you had just witnessed and taken a part in. As you stared out the windshield, the lights passing in gleams, a small note on the dashboard stood out to you. 

Tucked between the dashboard and the air vent, a small white envelope was crumpled slightly, caught on a jagged comer of the beat up car frame. A minuscule read heart adorned the sealed note and you leaned forward to pull it out of its hiding spot.

Edward watched you carefully, only peeking at the road. He couldn’t see what you were looking at but he could tell that it had you captivated. He swallowed hard and his eyes shot forward as you sat back in your seat with the letter in hand. 

“Were they... from you?” Your voice was quiet as your stomach flipped and a small smile ghosted over your features. 

“Y-Y-Yes.” He stammered quietly, knowing there was no point in denying it from here. His gloved hands fiddled with the steering wheel as he kept his gaze forward.

“These have made the mornings very exciting for the passed few weeks.” You giggled as you thumbed the note between your fingers. 

"Y-You're not bothered by them?" His surprise wasn't masked. "O-Or that they're from me?"

"No, of course not." Your voice was low but it was steady.

Ed slowly came to a stop, pulling his car to the side of the road. Slowly turning to you, he cautiously took your hand in his own.

" I am so sorry for getting you involved in this. I understand if you want to turn me in. All I ask is that you give me enough time to get away." His voice was strained and quiet but his words were sure. He did not look you in the eyes but rather at the hand of yours he was still holding carefully.

"Just promise me your life was in danger." You said as you held his hand tighter.

"It was." And he looked you in the eye.

And that was the truth-about tonight at least.

"Then just take me home and stay with me tonight, don't leave me alone." You whispered.

"Okay. Well be safe at my place." He smiled as he uncertainly pressed a kiss to your cheek.