Summary: You find yourself being kidnapped by the Riddler. Things turn from deadly to sexual.

(Warnings: This is smut so there will be mentions of abuse, implied rape, degradation,dacryphilia, overstimulation, choking,etc. Here's for all of your thirsting for the Riddler but haven't found a single smut one shot yet, you are all welcome!!)

I had been knocked out. The last thing I remember was walking down the Gotham streets leaving the iceberg lounge. It's wasn't a great place for a lonely woman to be but I had be there, work is work no matter how dangerous things may get. I absolutely despise working there for Falcone and Cobblepot, but I have bills to pay, not only that but I am planning to leave this city for good.

There's been enough damage done so the best thing I can do is leave this awful destroyed many of us have called home.

But now here I am tied up to a chair with tape over my mouth and with no place to escape. I tried moving my hands but they were too tied up, I had a knife with me for self defense but that wasn't on me anymore.

"You're awake." A deep male voice spoke throughout the room I was in.

The room was dark and i found many torture devices on either a wall or placed on a table nearby. I looked around and began to get scared at the things, my palms began to get sweaty and my legs were shaking.

"Looking for this?" The man evilly chuckled clearly showing a psychotic side. He held my small pocket knife in his hands when he came around me and took the tape off me.

This man is The Riddler. I recognized his mask and attire due to the many live streams he's been uploading, needless to say there's already a huge group supporting his beliefs.

I scoffed and began to laugh at him. "Do you really think you can scare me? Are you going to ask me one of your little riddles and let me go?"

Truth be told I was extremely scared, I believed in Gotham for years and never once had I faced the killer before me. Worst thing is this guy isn't fooling around, he's the one who killed the mayor and two policemen.

A hard slap landed on my cheek making me feel a stinging pain. I've received harsher treatments, I shouldn't let this knock me down. "How does it feel being the one tied down."

I ignored his words and looked back at him. "What do you want from me. Money?"

Riddler grabbed my hair and held me tight in his grip. "I want you to suffer the same way I did. No one is saving you this time." He ended with another laughter.

He really is a psychotic man. I tried pushing him away from me but that clearly failed. "I have no idea what you're talking about."

"You're going to die soon so I might as well just refresh your memory."

Riddler softly spoke and showed made me turn my head to the left, on the wall many pictures were plastered, want to come my attention one with the little boy with glasses in the choir. That's one of the orphan kids back then at Wayne orphanage.

The quiet boy who barely spoke to anyone, fascinated with riddles and puzzles. It all made sense now, "Edward Nashton.. you're that little boy."

"Who's not so little anymore." He sang and laughed right after. "Don't you just love living the past? All the fond childhood memories we all shared."

Him kidnapping me now makes sense. I wasn't orphan I felt lonely growing up, so the only way I felt satisfaction with myself was taking advantage and bullying those weaker than me. A group and I back then at the orphanage used to bully Edward.

We didn't have much going on back then so we did whatever we could not bore ourselves. What we did back then was horrible.

I looked over at Edward and deeply regretted harming him the way I did back then. "Words can't describe what I did to you, Ed."

"You don't have the right to call me that not after what you all did!" He snapped and began taking off his mask.

"I had many countless nights because of you. I dreamed of the day where you would be the one getting punished instead of me. And now it's all going according as planned." He giggled and had a sadistic smile on his face.

"What I'm about to do to use worse than what those fools had to go through. I remember over hearing that there's one thing you were afraid to lose."

One thing afraid to lose? My blood ran cold, but no he wouldn't do that now would he??

Edward made his way back to me and held my chin. "How does the saying go? You always harm the ones you love. You used to bully me every day, which must've meant that you liked me." He sang the last part.

"And I know you are secretly enjoying this, being all tied up and helpless." I pressed my legs together and felt ashamed because he was right. I did like Edward back then but I was a bitch to everyone.

"No more lies, (Y/N), or you'll end up like the mayor." I had chills imagining the horror the mayor must've felt..but I was also feeling excited...

"Stand up!" He loudly said making me stand up right when he untied my legs. I flinched when I felt his gloved hand across my stomach, he held the pocket I had and started to cut off my clothes soon leaving me all bare, I felt a rush of embarrassment and excitement.

He began dragging me further in the apartment until we made it to a room until he ordered me to sit

I did as he said, and sat on the edge of the bed, waiting obediently. "Lie back, hands above your head." A shiver went through my spine at his dominance and proceeded to lie on my back.

Edward stood above me another wicked smirk across his lips. "Look at you. Such a little whore all tied up for me. Not even a fight. You just let me do whatever I want."

I felt my cheeks heating up, I should be embarrassed at myself for enjoying being taken advantage of. "You really think I'm enjoying this?" I made it seem like I wasn't interested, that i wanted this to be over

Placing a knee between my legs, he leaned back and harshly grabbed my the face, "You'll see."

Edward crawled his way up and placed his lips over mine, his tongue wasting no time exploring my mouth. He straddled me and I felt him running his hands up and down my torso, his calloused fingertips rough against my soft skin. 

His lips soon left mine and his teeth raked along down my neck, biting every so often. "Fuck." I breathed out, getting lost in his touch. He hasn't done anything yet, yet I am already losing.

He leaned back onto his knees, my legs trapped beneath him. Unexpectedly, his hand came down to strike one of my breast, "Shit!" I hissed and felt a rush of excitement down my legs.

I winced and tried to move away when another smack came upon the other breast, before he reached down with both hands and cupped your breasts in palms, rubbing them, "You look so beautiful. All tied up, helpless, completely at my mercy like I wanted." Edward whispered in my ear, "Your make me so fucking hard." 

Slowly Edward crawled his way back down and threw one of my legs over his shoulder, "My, my, look at you, you're dripping and I've barely started anything."

Edward hooked his arm around my leg and used it to gain better access to my core. I looked and bit my lip. This is really happening.

"Oh my God." I bit my lips hard when he used a thumb to tease my clit, my eyes then shut tight when I felt him licking a long stripe up my slit. I gripped onto the covers below and moaned out loud he only started getting rougher.

I noticed a small grin plastered on his face. Both my hands gripped his hair tightly when I felt myself getting closer. He flicked and sucked, his tongue flattened as he licked a wet stripe from my clit to my opening, pushing his tongue inside of me.

My head fell back and I began to pant hard. The sounds coming from Ed as he sucked me were dirty, the moans and slurps began to drive me closer to the edge.

"I'm close!" I cried out and squeezed my legs when I arched, slowly, he entered a single finger inside my entrance and moved it just barely, teasing you as he continued assaulting my clit. 

Before I could come Edward removed himself from me I glared up at him and felt my punching him for leaving me like this. "You can't leave me like this you bastard." I shut my mouth when Ed wrapped a hand on my neck.

"Someone sure sounds ungrateful."

"I'm sorry..sir." I blushed hard when I said those three letters.

Edward suddenly added another finger and started ramming them into me. The familiar sensation returned getting tighter."Fuck, fuck, I'm gonna cum!" I cried out, wrists raw from pulling on the tight rope I still had on. I cried out loudly when he continued fingering me until I came over his face, his glasses becoming wet.

This didn't stop him though, Edward flipped me onto my stomach and crawled up on the bed. I caught myself onto the headboard, hands gripping the wood tightly when I felt Edward behind me, surely he got himself rid of his clothes. He grabbed my waist and rubbed the head of his cock against my folds. He entered me slowly, feeling my walls stretch around him as he did. "You feel so fucking good."

Ed grabbed my hips roughly and pulled them back to meet his hips as he slammed into me. "Fuck, Ed!" my head fell forward, knuckles turning white as my grip tightened. 

His hand struck my ass, a red mark forming immediately on it, he reached his other hand around my front and gripped your throat, using it as leverage to pull me back against his chest. His fingers tightened around my throat as he thrusted hard into me.  

"You feel so good sir." I moaned and tears began forming in my eyes. My legs began to shake as he reached down and rubbed fast circles on my clit. "Oh my god!"

Edward laughed behind me crazily and leaned close to my ear. "You wanna cum?" He asked, his cock twitching inside of me. My makeup was already ruined and running down your my cheeks.

Even though he knew I was on the edge, Ed continued to rub my clit faster this time applying more pressure, falling over the edge as he felt my walls clench around him in a desperate attempt to keep from cumming. He kept going hard and fast, his seed filling me and dripping out every time he pulled out. 

I squeezed my eyes shut and finally came around him. Without a word, Edward pulled out and flipped me over, ruining my orgasm for a moment until his fingers re-entered me. He thrusted them upward into my g-spot as fast as he could. The assault on the most sensitive spot quickly became too much and I tried to writhe away from him, "Agh! Okay stop!" I cried out, trying to wiggle his hands out of me.

Edward smiled to himself snd shook his head, "You said you wanted to continue cumming." 

His fingers moved faster and his other hand came to press down on my lower stomach, intensifying the mixture of pleasure and pain. His thumb came down to rub my clit hard making me scream, the pleasure transitioning to pain, "Shit, shit!" 

I felt another sharp slap on my cheek and saw he wasn't satisfied. "We're not stopping until you cum again." My breathing was shaky when I came down from your intense high once again.

I continued to pant and try to regain my birthing back. I winced when I felt Edward started to untie me, my wrists were red and bleeding a bit. Edward adjusted his glasses from falling down until I wrapped my arms around him and brought him down to kiss my lips

"You aren't escaping from me again this time." He said with another sadistic smile.