Alright, here's a Masky x Reader lemon~ In this one, your a servant of the creepypasta and Masky is your intended master. The two of you DO NOT get along- so, shit happens.

Anyways~ This was done as a request by someone here on Tumblr. I hope you enjoy it. (I know you wanted something rough but I just HAD to make it kinda soft towards the end XP )

Enjoy~ (Beware of smut, lemons, and some slight abuse)
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The sound of glass shattering woke her from her dreams, but she didn't bother to get up and find out what had done it- because she already knew. This wasn't exactly the first time it had happened. So, she just laid quietly in her bed and waited for it to be over and done with- just like the hundreds of other times before. Before long, she heard the telltale sounds of someone climbing through her bedroom window, and walking across her floor. She didn't move a muscle as the person who had broken into her home approached her bed- sometimes he just left her alone, and she hoped he would tonight. The feeling of cold air hitting her skin shattered her hopes as she soon came face to face with the person she didn't want to see or have around.

"Slenderman sent me here for the night, so make room." The somewhat irritated voice of none other than Masky said sternly as he eyed the woman lying calmly in her bed. In response, said woman shifted to give him enough room to lie in bed, but she made no move to complain or resist. She knew better than to resist by then- what was happening occurred on a weekly basis with her. That was the price she had to pay for being allowed to live. She'd discovered the hideout of the creepypasta by chance, and rather than kill her on the spot, Slenderman made her a deal. The deal was that she become a servant of the creepypasta- namely, Masky, who lacked a servant of his own. She agreed, but only because she had the will to live. Since then, she'd been in charge of getting the proxy his supplies, housing him when he needed a place to hide, getting him his pills, and etc. She hated every second of it- so did the others. Yes, others. Every creepypasta had at least ONE normal person acting as their servant- their link to the outside world. They all gathered for meetings and such from time to time, and the one thing they all had in common was a hatred for what they had to do. She shifted further way from him as he climbed into bed- she didn't want to have any physical contact with him. Why? Because he was mean. She'd learned the hard way that he was more than willing to smack her if she acted out of place- she'd had to go to college hiding her bruises on more than one occasion.

As soon as he settled into bed beside her, she reached for the blanket and pulled it back over her- he did likewise to keep from getting cold. Since she wasn't facing him, she couldn't tell if he was wearing his mask or not. Sometimes he did, sometimes he didn't- but, when he didn't, he typically tried to talk to her. That never went well. He'd ask her questions and eventually, she'd give an answer he didn't like- then he'd punish her. Usually he just smacked her, but sometimes, he took her to "Work" with him then made her clean up his mess when he was done. On those days, she'd return home to spend an entire night sitting in a tub of cold water. Those were the days when she most questioned why she was still alive in the first place.

"(Y/N), did you get me my pills?" Masky asked after a minute or so of lying in silence- great, that meant he didn't have his mask on. Meaning she was either going to get hit, or forced to clean up a bloodbath.

"Yes sir, I got them this morning." (Y/N) said through gritted teeth as she clenched her fists into the sheets. She really didn't want to talk to him. She didn't want him there- she wanted him to just leave her alone and let her live in peace. Sadly, she knew that wasn't going to happen. She felt him stir beside her- he had more than likely sat up. She could feel him giving her the evil eye.

"I don't like your tone of voice." Masky said in as calm a voice as he could muster, though she could clearly hear the anger radiating in his voice. Since she was pissed off herself, she couldn't prevent herself from snapping at him.

"Well, I don't like being your slave but I gotta fucking deal with it! Just go to sleep you-!" (Y/N) tried to speak only to be cut off when he slammed his fist against her side roughly. The next thing she knew, he was pressing her against the bed with his hand tightly grasping her throat. She tried to catch her breath, but was unable too because of his grip- if he didn't let her go soon, she'd pass out and probably wind up dead. To make matters worse, she couldn't struggle- he was sitting on her stomach and his knees were pinning down her arms. The most she could do was thrash her legs around in a vain attempt at throwing him off of her. Luckily for her, he loosened his grip to keep from strangling her- but, she'd still have a new bruise to hide in a few days. Then, he lent down so that his face was only an inch away from hers, and he growled.

"Remember your place woman, I could kill you in an instant and no one would do so much as shed a tear over you! They'd just say you should have behaved, then they'd get on with their lives!" Masky spat angrily, before he removed his hand from her throat to let her breathe properly. She gasped, panted, and wheezed for a few minutes- he continued to sit on top of her to ensue she didn't try to throw a punch at him. He didn't quiet expected, but she had smacked him back once- and he'd made sure to really lay into her after she did. However, what he saw next startled him. Tears were welling in her eyes, and a pain radiated from her expression that he had never witnessed before- she'd never let him see by expression that she was in pain. For a split second, he froze in shock- and that gave her the chance to vent her frustrations at him.

"Well if I've got so little to live for then why don't you just kill me?! Why not do it and get it over with so I don't have to deal with all this bullshit anymore?!" (Y/N) half screamed as she glared up at him through crying eyes. Her little outburst startled him so much that he couldn't even think of a response- so she just kept going.
"You think I wanted this?! That I wanted to find you fucking murderers and become your godforsaken slave?! No! I just wanted to go for a walk in the woods to clear my head after I'd lost my entire fucking family to a fire!… Then you and your dumbass partner just happened to be in the goddamned woods carrying around a bunch of duffle bags and I followed you because I thought you were going camping!.. I thought that maybe you knew about some beautiful lake hidden in the middle of the woods and I was so upset over loosing my family that I blindly followed you hoping that maybe some stunning lake might help me get my act together!… But no. All I found was an ugly old mansion filled with monsters and serial killers- monsters and serial killers that forced me to become a servant to a fucking sadist in exchange for letting me live!… So go ahead, kill me… Its obvious you'd be doing me a favor…" She screamed at first, only to fall into a pathetic whisper as he turned her head to the side to let her tears fall freely. She fell silent and stared at the wall sadly- she made no move to sit up or roll over when he climbed off of her stomach to sit on the bed. Nor did she make a move to resist when his hands fell around her throat once more. She just closed her eyes, and waited patiently for the black out- which soon sent her plummeting into nothingness…

Sometime later, she woke to find herself with her arms bound to the headboard of a bed. She didn't know how long she had been there, or who had put her there- but she knew that she was naked. She could feel her bare skin rubbing against the smooth fabric of the sheets as she squirmed in an attempt at freeing herself. She soon gave up on getting free, and found herself feeling slight gratitude that whoever had done this to her had had the decency to cover her bare body with a blanket so she wouldn't be as exposed. Or, maybe that was just to prevent her from getting to cold. Either way, she had a blanket covering her and she was warm, so, she could be somewhat grateful for that. She was surprised though- not about being tied up, but about being alive. She was sure that Masky would have done off with her. Hell, for all she knew the bastard was going to give her to Eyeless Jack as a fresh food supply- or, maybe Slenderman was going to eat her. In all honestly, she didn't know- but, she believed she was going to die, one way or another. Part of her hoped it would be Laughing Jack, or even Jeff the killer that came and did her off. Why? Well, for one- Jeff wasn't exactly known for torturing his victims physically. He gave em a mental scare, then killed them with a quick blow- so, she wouldn't suffer much at his hands. As for Laughing Jack- she'd been told be many of the other servants that he was the best way out if you wanted death. Apparently dozens of the other servants had gone to him in the past, and according to the others, you were always buried with a pleasant smile on your face. Somehow, the clown killed you with joy- some people said he used illusions to make you remember only happy things while he proceeded to rip your entrails out. Sure, the death would probably be more gruesome- but, it would be worth being happy come death.

Worst case scenario- BEN would be the one to kill her. Everyone warned that if you wanted to die, make sure it was by the hands of anyone other than him. He had a reputation for killing with fear- he'd get inside your head and show you things so horrific that you had a heart attack, or a stroke, and die. Typically, it took him a few days to do it too. The sound of a door creaking open sent a shiver coursing through her body as she prepared herself mentally for whatever death was about to befall her. The other scenarios passed through her mind as she clenched her eyes shut to keep from seeing it coming. Eyeless Jack harvested your organs, Slenderman ate you alive, Ticci Toby chopped you to pieces, Hoodie carved the slender symbol into your skin then slit your throat, ripped your throat out. ZALGO ripped your heart out, Sally stabbed you with colored pencils, Shadowlurker sucked out your soul, Masky… She didn't know. No one ever went to Masky for it, so, no one knew how he did it. She clenched her eyes shut tighter when she felt a hand press against the side of her face- she immediately began to narrow down the possibilities of who was going to kill her just from the feel of it. Whoever was touching her, they were human- so ZALGO, Shadowlurker, Slenderman, - they were all out of the question. She pressed herself closer to the bed when she felt the blanket covering her body get pulled off of her- the rush of cold that hit er made goosebumps form atop her skin. Not long after, she felt a hand run along the surface of her abdomen.

"Open your eyes and look at me (Y/N)." The stern voice of Masky sounded off out of seemingly nowhere, causing (Y/N) to snap her (E/C) eyes wide open to stare at him. To her surprise, he wasn't wearing his make- nor was he wearing a jacket or a shirt. The only thing he seemed to be wearing was a pair of pants. She swallowed the lump that had formed in her throat upon seeing the expression on his face. He looked angry- and when he was angry, he hurt her. The fact that he was angry and that he was only wearing pants made her believe that his killing method was going to be messy. So, imagine her surprise when he put his hand on the back of her head to hold her in place while he lent down to force a rough kiss against her lips. Her immediate response was to bite his lower lip and jerk her head to the side at the same time- somehow, she was surprised at the taste of his blood in her mouth. She was even more surprised by the sound of the feral growl that left his lips after he'd recovered from the temporary shock of what she'd just done. Mercy, what had she gotten herself into? The next thing she knew, she was forced onto her knees. He made her hold on to the headboard of the bed if she didn't want the ropes to dig into her skin. Then, before she could utter a word of protest, she felt the sharp sting of his open palm slapping against her backside. The small jolt of pain made her let out a pathetic cry as she tightened her hold on the headboard. She was absolutely positive that that one swat had left her cheek bright red.
"If you know what's good for you, you'll behave yourself (Y/N). I'll be more than happy to make this hell for you- but if you do as I say like a good little girl, I wont hurt you. Much." The proxy said in a dark tone as he began to gently rub the sore spot he'd left on her arse with the palm of his hand. The soft action paired with his sinister tone of voice was more than enough to send a violent tremble coursing through her body. All at once, she realized what his plan was.

"D-don't you fucking dare Masky!" (Y/N) said with a pathetic excuse for an angry tone as she felt him shifting around behind her. She turned her head to the side to glare at him, only to watch as he undid his pants and pulled them down to reveal his semi-erect length. A frightened blush appeared on her face at the sight of it, and another tremble rushed through her body at the thought of what he was going to do with it. To make matters worse, he flashed her a smirk when he noticed her reaction to the sight of his bare body.

"Like what you see~?" Masky asked in a mocking tone as he wrapped a hand around his length to get it ready for what he was planning on doing. The action, paired with his question, only flustered (Y/N) further- which made her pull at her restraints.

"N-no I don't fucking like it! Let me go you bastard- and get away from m-!" (Y/N) practically screamed, only to have her voice cut itself off when she felt Masky put his hands on her backside to spread her sex. Her blush only darkened when she felt his gaze on her most private parts.

"That's a lie (Y/N), I can see you getting wetter by the second~" Masky teased, before he suddenly lent down and flicked his tongue against her sex in teasing manner. Nothing in the would would have been able to hold back the moan that fled her lips when he licked her- there was no denying how utterly aroused the situation had made her. God, she hated every moment of it. Before she could do so much as think of a plea for mercy, she felt his tongue against her again- and this time, he made sure he didn't break contact. He pressed his open mouth against her sex and licked her roughly- not once did his tongue leave her slickened opening. He dragged his tongue up and down her folds, before he all out shoved it inside her and proceeded to fuck her with his tongue. To her shame, she couldn't help but rock her hips against him as he ate her out. She couldn't stop herself- it felt so good, but she wanted to kick herself in the stomach for it. Masky was merciless with his assault. He kept her lower lips spread and he made sure to shift his body every time she squirmed to try and get away from him. He refused to break contact with her body- and he refused to back off when she began to struggle as her orgasm approached. If anything, he licked her harder when she began to whine and thrash- he wanted her to cum because of his tongue, and he knew if she did it he'd shatter another part of her will to fight him. In the end, she came hard against his tongue- and he lapped at her nectar greedily as she trembled in his hold. When he finished, he pulled back and watched as she continued to tremble from the aftermath of her orgasm, and he smirked deviously at her.
"Heh, looks like all I really needed to do to make you listen was give you a good fuck~ Look at you, your not even fighting back~!" He said with a chuckle as he shifted a bit behind her- it was about time he gave himself some sexual satisfaction. First though, he wanted see how much of a fighting spirit she had left. So, he ground himself against her to see how she'd react.

"G-get the f-f-fuck away from m-me!… B-bastard.." (Y/N) panted as she felt the masked proxy press his length against her- though it was obvious by the tone on her voice that she wanted him as badly as he wanted her. She just had to much pride to admit that she was in need of a good pounding. Considering it had been nearly four and a half years since she'd last had sex, it was no surprise that she craved the contact. Yes- she had been servant to the proxy for four, grueling years. Thanks to their rules, she had to break up with her boyfriend otherwise watch him die at the hands of the creepypasta. She wasn't allowed to date without their say so- naturally, that meant she couldn't do the things that came with dating either. Masky chuckled in response to her attempt at sounding tough, and instead of giving her what he knew she wanted, he gave her arse a firm swat with the palm of his hand. He wasn't surprised to hear the strangled gasp that she released when he did.

"Cut the crap (Y/N), I know you want it~ You want me in you as badly as I want to bend you over and fuck you senseless! So, drop the tough girl act and tell me that you want it~ Say you want my cock and I'll give it to you~" Masky chimed with a mocking tone as he massaged the sore spot on her rear again. In response, (Y/N) groaned and tried to pull away from him- but he held her firmly in place by her hips.
"Say it." He said sternly as he gave her a mix between a glare and a smirk. She groaned and continued to try and pull away from him.

"No!" (Y/N) panted as she struggled, only to make a pained sound when she felt his spank her sore backside again. She clenched her jaws and eyes tightly in response and tugged at her restraints.

"Say it!" Masky ordered once again- his hand was raised and ready for another swat if she refused.

"No!" (Y/N) shouted- and she felt the sting of a slap once more.

"Say it!" He ordered.

"No!" She received another slap. This continued on for what felt like hours to the two of them. He would order her to beg for him, then he would spank her when she told him "No". The process went on until the cheek he'd been slapping grew so red it looked as if it might bleed- and his hand suffered a similar injury. Honestly, he was surprised at how much of a fighter she was- even as tears began to roll down her cheeks from the pain, she continued to deny it. She must have hated him more than he thought- but he wasn't about to let up. He'd make her beg for him to fuck her even if it cost him his hand- which was slowly but surely becoming a real possibility. After well over two hours of spanking her raw, she finally submitted.
"Enough!… Enough… I-I want it…" She said between sniffles as she bowed her head in submission. He sighed in response and set his sore hand atop her raw cheek to rub it gently, then me moved to hover over her. He pressed against her backside and flattened his chest atop her back. He rested his chin atop her shoulder so that his mouth was next to her ear.

"What do you want?" Masky whispered against her ear as he lightly rocked his hips to grind his length against her, provoking a shudder from her sensitive body. She whimpered as his unusually soft tone of voice, and remained submissive- he'd broken her, if only for the night.

"Y-your cock… I want your cock, inside me… Please…" (Y/N) said quietly as she attempted to look away from Masky, who moved one of his hands to force her face to the side so she'd have to look at him. He saw it in her eyes- she was completely and utterly humiliated. However, he could also see that her statement was far from a lie. She wanted him, bad- and the pain he'd put her through only made her more desperate for the pleasure. He offered a soft smile- one which she had never seen before- before he moved their faces closer together.

"Good girl~" Masky said gently, before he pulled her into a soft kiss. As he did that, he steadied her hips with his other hand and he pushed inside her. They both moaned loudly into their kiss. As he began to move, he shifted his hand from her hip. He move it to her abdomen, then slid it downwards until he felt her clitoris- he rubbed it carefully in time with his thrusts. She moaned and pressed against him as he moved, and he eventually moved his hand away from her face to let her kiss him as she pleased. She rocked her hips in time with his as he moved- had she known he'd of been this gentle when he told her to bed, she'd of probably done so a lot earlier. Had he known how well she responded to being treated like a woman, he'd of probably never had to deal with her attitude. Granted- had either of them known what they knew now, they wouldn't be doing what they were doing in the first place. Somewhere along the lines, he broke their kiss to trail his lips down her neck- he bit down on the junction between her shoulder and her neck gently as he moved against her. Whether he seemed the type or not, he preferred soft sex to violent humping- though he was typically a bit rougher than this. The only reason he was being so soft now, was because he could feel the heat radiating off of her sore cheek. He'd smacked her so many times he may as well have taken a hot pan and pressed it against her arse- because he knew for a fact she wouldn't be sitting for a couple of weeks. Besides- he liked her better like this. She wasn't giving him an attitude or trying to pick a fight- and that's all he really wanted from her to begin with. He moved his mouth to bite the back of her neck gently as he began to pick up the pace- he'd need to go a bit faster if he wanted either of them to reach their sweet release for the night.

Her blush darkened and she moaned more as she felt the fingers he had teasing her clitoris pick up the pace along with his hips, and she arched her back a bit to press more against his mouth. She'd forgotten how nice it felt to be with a man. She's certainly never expected to be doing this with Masky, of all people. If anything, she'd assumed Jeff or Laughing Jack would've been more likely to do it, considering their habits. She let out a sudden gasp when he bit a little harder on the back of her neck, and she turned her head to try and face him on impulse. He wanted to bite- and she had a spot that just drove her mad that she had to tell him about.

"Ma-Masky, will you b-bite my ear- mm~ P-please~?" (Y/N) moaned gently, only to bite her lip to prevent from calling out in pleasure when the proxy immediately accepted her request and latched on to her ear with his mouth. He nibbled and tugged lightly as his thrusts hit his preferred speed, and they both moaned loudly in response to the pleasure they were feeling. Honestly, he was glad she told him to bite her ear- as soon as he did, he felt her insides clench around him. Every time he nibbled or tugged, she spasmed a bit. That was what eventually threw him over the edge- the more she clenched around him, the harder it became for him to hold on to the pleasure. She came at the same time as him thanks to the hand he had working her clitoris- her insides constricted with orgasm just as he tensed to shoot his load inside her. After that, he just wrapped his arms around her torso and lied the side of his face on her back as he waited to come back down from his high. She'd of probably done the same had she not been tied to the headboard- but, somehow he managed to untie her wrists as he settled back down. As soon as she was loose she collapsed on top of the bed with him still clinging to her. He lied on top of her and they both panted quietly as they recollected their senses. Thanks to the wonders of euphoria, neither of them had been aware of how sweaty they'd gotten during- but boy did they become aware once they started cooling off. Not because of a smell though- the scent of sex was to heavy in the air for them to notice the smell of sweat. What bothered them was how sticky the felt. In the end it bothered them so badly that they went straight for the shower as soon as they could stand.

Granted- Masky had to help (Y/N) walk. Her legs had pretty much gone numb from the sex, and she limped on the leg connected to the sore side of her arse. He actually had to help her with everything because of how worn out and weak he'd made her. The wound up sitting in the bathtub with the shower on because they didn't have the energy to stand and clean themselves at the same time. She sat in his lap facing him and they washed each-others bodies. By the end of the shower Masky had more or less recovered from the ordeal, but (Y/N) was going to be pretty worn down for a day or two. Probably because he'd made her cum twice after four and a half years of no sexual satisfaction- having an orgasm after that long would drain anyone for a little while. Once they were out of the shower he helped her back to bed, then retrieved a tube of aloe from the bathroom to fix up her sore bottom. He applied it using the hand he'd spanked her with so he could kill two birds with one stone. As soon as that was taken care of, he climbed into bed with her and pulled the blankets over them to keep their bare bodies from getting cold- neither of them cared enough to bother with getting dressed. After that, they lied in bed for a few hours in complete silence, before (Y/N) decided to speak up.

"Why didn't you kill me?" (Y/N) asked quietly as she stared at Masky, who looked at her and shrugged.

"I never wanted you dead." Masky said calmly. The woman sighed and watched him tiredly.

"Why did you have sex with me?" (Y/N) asked- her voice was tired, but very calm. She'd already accepted what happened and didn't seem to regret it.

"I thought it might make you hate me less. Its how Hoodie got (F/N) to stop fighting with him. That's why she doesn't bother to complain anymore." Masky said honestly. There wasn't any point in trying to lie- besides, he saw no issue with what he said. She sighed.

"Do you know why I hate you in the first place?" (Y/N) asked calmly. The person in question shook his head no in response, so she opted to tell him.
"I don't like how you make me feel. You treat me like I'm less than a human being. I do all your errands and not once do I hear a thank you or a nice job. I can't say how I feel without you getting pissed off and hitting me- and honestly I think so poorly of you that I expect you to punch me in the face for saying this…" She said weakly- she curled into the fetal position as she spoke without realizing it, but it proved how honest she was being about thinking he was going to hit her. Instead, the proxy wrapped his arms around her to pull her closer to him.

"I treated you like that because you never showed me any respect. Your attitude pissed me off and I thought a little discipline might make you act a little better." Masky said calmly as he put his chin on the top of her head. He had a feeling that holding eyes might her might set something off- though he didn't know why.

"I never respected you because I didn't think you deserved my respect. You never gave me a reason to respect you… So, I guess we're both at fault, huh?" (Y/N) asked quietly as she shifted a bit closer to Masky. Honestly, she'd gotten so used to sleeping next to him that she slept easier with him by her side- so it was pretty normal for her to be comfortable next to him as long as he wasn't mad. When he got mad, she got mad and then things just went downhill from there.

"Yeah…" Masky said quietly as he began to rub her back a bit. He enjoyed the feel of her skin against his fingertips for some reason. After a moment, he sighed and sat up a bit to look down at her.
"Tell you what. I'll start treating you a little nicer, and not hit you, as long as you'll start being more respectful. Deal?" He asked calmly. She looked up at him after a moment.

"Are we going to keep having sex, or was this a one time thing?" (Y/N) asked quietly- a slight blush painted her cheeks. He sighed.

"No way in hell was this a one night stand." Masky said calmly, though there was a slight note of irritation in his voice- it actually made him sound kind of cute.

"Promise to be that gentle every time we do it? Unless I want it rough…" (Y/N) asked. The male in question nodded and lied back down to get comfortable.
"Then deal." She said with a bit of a smile, before she fell asleep in his arms.

They both kept their ends of the bargain.
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I hope everyone liked this~ Next on my list is a Masky x Hoodie lemon requested by a friend. Her birthday is coming up.

No promises on it being done by your B-Day Nixie, but, I'll get it up as soon as I can.