being whimsy

Ah, yes, the Housewarden of Heartslabyul, himself. The one who lived so strictly abiding by the rules of the Queen of Hearts. Riddle was always so strict on himself and his peers, and he continued to enforce these rules even after his overblot. Of course, he was more lenient, now.

You always wondered what it'd take to get him to act out. It was unlike Riddle to completely go off the rails and do something insane. You could never picture him cheating on a test or sneaking off campus after hours or roughhousing. Being an overly curious person, you wanted to see him do something completely out of character. Something that no one else would believe unless they saw it.

Honestly, you don't even remember how it all started. You don't really care to remember at this point.

All you cared about was that the former tyrant of the Heartslabyul dorm, the boy that was so hell-bent on following the rules and setting an example, was on his way to being your personal little plaything.

_

"You're so cute, Riddle," You cooed affectionately, your soft hand gently caressing the top of his head, fingers entwined in his red locks as his tongue was buried as deep as it could possibly go inside of your pussy. His eyes were glazed over with lust, and they would either stare up at you affectionately or roll to the back of his head. "Such a good boy for me." The redhead whined at your praise, thrusting and swirling his tongue along your walls before pulling it out and dragging it along your clit.

He was so much better at this, now.

The first time he ate you out, you had to coach him through every little thing. Being a fairly fast learner, Riddle picked up the best ways to make you feel good. You pulled his head back, his saliva clinging to your pussy in such a deliciously devious way. "Look at you," You murmured, his glazed over eyes staring up at you. "Getting all messy just to make me feel good... I wonder what everyone else would think." You shoved his face into your pussy again, Riddle immediately gripping your thighs like a vice as he aggressively ate you out, dick twitching in his pants. "Mmnhh! H-How would your dormmates r-react, hmm? Seeing their leader so... S-So..." You let out a soft moan as his tongue pressed against an especially sensitive spot. "So submissive and good for me... So quick to get on your knees and pleasure me..." He moaned into your cunt at your words, thrusting his hips against the air as he swirled his tongue around your clit. "P-Please," He whimpered. "W-Wanna... Be in you... Please l-let me..." Riddle's voice was so soft when he begged. So adorable.

You licked your lips and tapped on your inner thigh. "You know the answer to that already, Riddle. Make me cum first, unless you want a punishment for not following my rules."

"P-Punishment...?" Riddle's heart skipped a beat at the sound of it, cock dripping with precum at the thought of being disciplined by you. "You want to be my good boy, don't you?" His hips bucked instinctively as he heard you call him that again, bottom lip quivering as those doe eyes of his stared directly into yours. Slowly, he leaned forward and dragged his tongue over your slit again, making you shudder. "I'll... I'll be a good boy," He murmured out softly, hooking his hands on the underside of your thighs while his thumbs spread the lips of your pussy for easier access to your cunt.

With little hesitation, he shoved his tongue into your hole, eating you a little more aggressively this time. You leaned back a bit, biting your lip to muffle a moan as you reached up to squeeze your own breast. The attention he gave to both your hole and your clit was just so perfect. Then again, he was a fast learner and a perfectionist. Your walls squeezed around his tongue as your body twitched, signalling that an orgasm was near.

"I-I'm gonna- hhnNGHH!" You're cut off by the slurping sound he made as his tongue moved faster, his hand joining his mouth in pleasing you. His thumb started rubbing quick circles over your clit as he thrusted his tongue into your pussy, making you arch your back and cry out as your orgasm washed over you like a tidal wave. Your juices poured out of you as your body spasmed, walls clenching and unclenching so rapidly around his tongue as you made a mess of his face and the bed beneath you.

Riddle pulled away momentarily, slowing his motions on your clit before doing so to allow you to ride out your orgasm.

Your chest heaved as you tried to catch your breath, eyes slowly meeting the clock hanging on a wall in his room. "Oh..." You murmured. "Just... In time..." You took in a deep breath as the fog in your brain slowly went away. "Class is about to sta-" You started to sit up, only to be pushed down by a desperate-looking Riddle who's unbuckling his belt. "I want my reward, MC."

Your eyes could barely take in his disheveled look. Your cum was dripping from his mouth and all over his chin, his uniform was wrinkled, his tie was off, and his pants were down. His throbbing, angry cock was sliding against your cunt as he held your legs in the air, his eyes never leaving yours. "B-But class, Riddle-" You hissed as the tip breached your entrance.

He couldn't stop himself from bottoming out, letting out a pathetic mewl as he felt your walls squeeze around his cock. Only a couple of seconds were given for you to adjust before he whimpered out an apology and started desperately thrusting into you.

Riddle's pace, unlike his disposition, was erratic and uneven, his balls slapped against your ass as his cock dove deeper into your hole with each thrust. His eyes rolled back and a twisted grin formed on his face. Slowly, his stormy gaze met your teary-eyed as he shushed you, your moans having gotten momentarily louder than his own.

"I don't want to go to class, MC... I want you."

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