Yandere Grell x Male!Reader

Another late night disturbance

Warning: DICKS.

You made sure to take your time on all your chores, not quite wanting to get to her "alone time" as she had planned. Even though you two were always alone so there's not really much reason for that comment anyway. Either way, you were actually somewhat exhausted from the work she made you do today. You did the dishes, dusted, cleaned bathrooms, cleaned the floors, cleaned the prison cell room, organized and cleaned the bedroom and master bathrooms... there was probably more that you're forgetting but whatever. Thankfully throughout the day, you only suffered 4 lashes including the one from this morning, a far less amount than usual. You of course had to give her a bath, listening to her talk about makeup and her nails and all that shit; supplementing your usual "yes, mistress" and an occasional compliment whenever necessary. Her face lit up each time you complimented her, showering you in kisses. You still, even after all this time being near her, never understood how there could be such a sharp contrast in her moods and actions. On one end she was sweet; showering you in kisses and buying you things, giving you all the (unwanted) affection in the world. On the other she chained you up, tortured you, and humiliated you to no end. Currently, you sat on the bed as Grell had ordered while she dressed herself from her bath, more than likely retrieving your lounge clothes. She came back out in silky red pajamas, walking over to you and undressing you, leaving the collar and leash, plus the thigh-highs on while she did so. She dressed you in a clean set of pajamas- wait were these new? When the hell did she get you these? Either way, they were extremely soft, feeling nice even when rubbed against where she whipped you. She yawned as she pulled up your pants, planting a kiss on your forehead before curling her body around yours and forcing you into a cuddle as she played with your leash. "You must be so exhausted, my dear, why don't we both rest for the night? You've certainly earned it~" she yawned again, leaving kisses all over your neck until she eventually laid her head down, feeling her slowly fall asleep behind you. You felt odd and displaced, how the hell was she that tired?! You were the one doing all the work! It wouldn't hurt to get some rest anyway. It's not like you could escape or do anything, even while she slept she kept hold of your body and a tight grip on your leash. Slowly, you shut your eyes and tried to clear your mind, focusing on nothing but sleep...

Eventually, this worked as you finally felt mildly at peace within your sleep, only to be disturbed by shuffling from behind you. Your eyes peeked open, revealing nothing but darkness as you assumed it was nothing, trying to get comfortable again and- what the hell?! You heard the shuffling again, but this time it was accompanied by a feeling of fabric sliding against you. Your eyes now wide open, trying to adjust to the darkness as you looked around, you tried to look at Grell to get a hint of what the fuck was going on, only for her to be conveniently behind you and- oh god. You heard a small whimper from behind you, followed by her body twitching and another, more forceful feeling of her hips being dragged along your ass; you could unfortunately feel her hardened member against you, too. Was she- was she seriously grinding against you in her sleep?! That answer turned into a quick yes as you felt her member being rubbed against you forcefully, almost moaning in her sleep. As nice as you would admit that it felt, you had to put a stop to her actions for the sake of getting some goddamn sleep. You tugged on the arm that held your leash, speaking in a harsh tone, almost commanding her; "Grell. Wake up." You could tell she woke up immediately due the sudden stop of her movements, yawning and kissing the top of your head. "What is it, my dear? Why must you wake me from such a lovely dream-" Slightly angered, you cut her off. "That's exactly what I was going to ask about. Why were you just.. grinding against me in your sleep?" You regretted that question as soon as you heard a deep chuckle from behind you, a less intense version of her grinding picking up. "Oh, that? Well, if you truly are that desperate to know. Asking a woman of her fantasies is quite bold you know~ If you were anyone just about anyone else I'd slap your face of. But since it's just us.. perhaps you'd like to experience it first-hand~" As soon as she said that, you attempted to dart away, forgetting she still had her arms keeping you in place. She picked you up easily and placed you next to the bed, her legs hanging off it and spread open- oh hell, you knew exactly what was about to happen, as you had been in this position before; below her with that God-awful look in her eye, this time clutching your leash tightly and pulling it, urging you forward as she pulled down her pants with the other hand. "Well, what are you waiting for? Don't even think about resisting this time, I'm in no mood for that. Don't test me, I will get the death scythe-" your eyes widened at such a threat so soon, you didn't even do anything yet! You stammered out a small, unsteady "yes, mistress" and pulled down her panties for her; her excited member springing up in your face. Reluctantly, you slid her member into your mouth, partially guided by Grell pulling your leash. You could hear her gasp above you, not even attempting to hide her excitement from you as you slowly moved your head back and forth. You steadily increased your pace, trying to make her release faster to get this over with, occasionally glancing up at her to see her expressions and try to gauge how close she was. As you continued, you slowly felt yourself pulled closer to her by your leash, forcing more of her member in your mouth as she gently thrusted it in your mouth while you worked. Regardless of how much internal conflict you had, you shakily reached your hand up and began softly squeezing her balls, looking up at her to see her overwhelmed with pleasure; letting out loud moans as she thrusted her hips harder against your face. You squeezed a bit harder, trying desperately to get her to release. Within an instant, you felt a sharp tug on your leash, forcing your face right up against your skin as she let out a loud moan unlike the others, convulsing as you felt a warm liquid drip down your throat. "Swallow it, love." Her voice was unusually shaky, giving some slack in your leash to give you room to back away from her as you swallowed her semen. "Good boy. Now get up on the bed, we're not finished yet~" You followed her orders as she pulled the lube out of the nightstand drawer, your stomach beginning to churn for a moment at the thought of what she was going to do- or, thought she was going to do. She pulled her panties all the way off, spreading her legs, then pulling you forward by your leash, followed by pulling down your pants. This was the complete opposite of the position you both normally took, Grell quickly reading your expression and cutting off your train of thought to answer your questions. "I've been wondering how this felt for quite a while, you know what to do. Just, do what I did the first time, and if you can help it please be gentle-" Ok, now you're really confused. Her begging you?! That was a first. But, as another way to look at it, this could be a small way to get revenge. "Yes, mistress." You replied, then began to mimic her movements with you as you spread the lube on your member, being quite generous with it before putting some on your middle and pointer fingers, spreading the oil around her hole as she let out soft noises at the sensation. You tried to push your fingers into her, but it was shockingly hard to do, she was really tight. There was no way she hasn't- well, maybe she really hasn't done this before. She moaned loudly as you pushed your fingers in, and she was extremely tight, unable to contain herself as you thrusted them back and forth. You then took your fingers out, positioning yourself before pushing yourself into her, feeling a sensation of pleasure ripple throughout your body, unable to control your noises as you watched her share a similar experience. You pulled back, giving her a moment to adjust before thrusting into her again, going gentle as she had asked at first. You actually found it quite hard to contain yourself after you first thrusted into her, your member throbbing for more at your gentle pace while you felt the odd feeling of pleasure spread throughout your thighs and knot in your stomach. You steadily began working up your pace as you watched Grell beneath you, her body twitching occasionally due to the overstimulation, fighting herself not to squirm around as she clutched your leash in one hand, the other clutching the covers. You began working up your pace to eventually match hers, steadily thrusting faster and harder against her and watching as she seemed to be getting close to her high. You continued to thrust harder, hardly containing your own noises as she suddenly let out a loud whimper, followed by her begging you through her moans to not stop. You took it you found her spot, and thrusted harder in the same spot. You saw this as your chance to get back at her, now ramming yourself into her hard enough to bruise her, but it wasn't as much of a satisfying feeling as you thought it would bring to you. It was of course extremely pleasurable as you felt your own high fast approaching, but she seemed to enjoy the rough pace rather than fight it, which was much to your disappointment. You felt yourself begin to tense up, your high fast approaching, fortunately being triggered by Grell's release; convulsing around you and coming onto her own stomach as you came inside her, more exhausted than you were before. You gave her time to ride out her high as her body continued to twitch before pulling out, watching as she slowly, without a word, fell asleep. Well shit, with her asleep, despite your exhaustion perhaps you could use this opportunity as you aren't in her arms anymore, and her grip on your leash was nonexistent. You carefully pulled your pants up, sliding your leash out of her hand, then shuffling off the bed carefully; not taking your eyes off her for a second to ensure she didn't wake up. With her apparently in a deep sleep, and you now free of her grasp, you could use this time as your only opportunity to explore the house. If you were careful enough.