The Loathing of Gwendolyn Winters
by Salacious_Ink
As soon as she had first met him, Gwendolyn Winters knew that she would hate Wallace Falt. The only thing she hadn’t truly understood was how quickly, and how deeply.
Gwendolyn was ambitious. She had recently earned a job working in a well known fashion brand on the strength of her resume. It might not have been an especially progressive workplace, but that even she, a trans woman, could find respect there spoke volumes about her worth ethic, of that she was absolutely assured.
But to properly work there since the commute had been horrendous, she had taken the risk to find some new accommodation. The house she’d eventually found a room to rent in belonged to a trans man, Wallace. He barely used the downstairs area of a lavish house he somehow happened to own and was renting it out as an apartment. Since he was also transgender, just in the opposite direction, Gwendolyn thought they might have something to talk about.
They didn’t.
It took Gwendolyn all of half an hour as she initially moved in to realise that Wallace Falt was a complete fucking loser. The anime figurines were … fine. She couldn’t really judge, anime was a popular medium these days. There were a lot of good shows worthy of respect. Though the fact that they were almost universally the more lurid kinds of figurines did irk her a little.
No. The worst of it was everything else about Wallace.
Seeing his floor of the house was a nightmare on its own. Any possible flat surface that wasn’t a display shelf for his oh-so-precious waifu dolls was stacked with every kind of crap imaginable. Used and unwashed dishes and crockery, newspapers and magazines she doubted he’d ever even read, random knick-knacks, game cards, and take away food containers. Not even to mention the ever-present and viscerally unpleasant corn smell he described as his “gamer funk” which somehow made it even worse upon hearing that. It wasn’t just that he never seemed to open a window, but it must have been from the dozens if not hundreds of empty bags of corn chips that were stuffed into the crevices of every part of the upstairs area.
And then there was Wallace himself.
Every time he opened his stupid goddamned mouth, Gwendolyn wanted to strangle him. First was that stupid nickname he’d immediately started using for her that made her skin crawl. His second offence was that he just wouldn’t stop throwing random Japanese words into conversation, as if that were ever a socially acceptable thing to do. Even remembering that she’d done the same thing during a particularly disappointing phase in early high school made her feel a deep emotional pain.
Cringe. That was the only word she could use to describe it. Pure cringe. As much as she hated to use a term coined by terminally online weirdos – the same kind of tribe Wallace surely belonged to – it really was the only one that her mind could conjure up.
If his words weren’t bad enough, his personality was worse. Gwendolyn didn’t like to describe people as lazy, but Wallace was fucking indolent. The fact that he never cleaned up after himself was plain as day to see, but the fact that he seemed to thrive off that fact was an absolute nightmare to her. She had worked her ass off for everything, only for this asshole to get lucky by buying into bitcoin early, cash out when the bubble was about to burst, and then survived off his savings before he could start living off her paycheck by renting out his stupid fucking house!
It wouldn’t be so bad if she didn’t have to look at his arrogant face every day. She could only access her level of the house through the stairwell right at the entryway through the front door to the house. The living room was almost directly in front of it, with Wallace typically playing a game or watching some garbage isekai brain rot at damn close to full volume. While she had to go to work, doing her absolute best for everything she had, it raked at her very soul knowing that Wallace would be sitting in the exact same posture by the time she got home.
More than once she’d even come home to see him masturbating to hentai, right in the middle of the god damned living room with the speakers on full blast.
The last time she’d started an argument about the condition he left his house in, Gwendolyn was screaming at him to take out his trash, and he’d blithely responded with “I mean if it bothers you so much, why don’t you take it out for me, Gwendy-chan?”
That particular phrasing had almost broken Gwendolyn. She felt every impulse in her body tending towards excessive bloody violence. But she acted like a mature adult about it. She turned on her heel, told him that if there wasn’t a change around the house she’d be out within the week, and went downstairs to melt her own fucking brains out.
Most likely because of her own Type-A personality, relaxation didn’t come easy to her. One of the few things that she found that helped her was trance. At first she’d tried meditation, yoga, all the conventional stuff. Trying cannabis was next, but in all honesty she couldn't stand the smell. But it was when she went searching on the internet she’d found a much wider bevy of options. The most cathartic one revealing itself to her in hypnosis.
A universe of worlds beyond anything she’d imagined. Limitless potential to transform, to relax, to be destroyed and remade, to feel utter peace or deepest fear or anything in between. And … the orgasms. By god the way fucking herself made her feel during and after a good hypnotic file were like no partner she’d ever brought to bed; the few that she ever felt were worth her time, at least.
She needed an escape, and something drew her to a new file she hadn’t yet touched. A hypnotic maid transformation. Gwendolyn bit her bottom lip. An evil thought curled up from her mind. Maybe, just maybe, this file might help her feel a little better about the fact that there was so much trash upstairs. Wallace included.
Her own section of the house was perfectly ordered after all. Logically, the way Wallace lived his life shouldn’t bother her if she didn’t even rely on any part of the upstairs area. She’d bought her own essentials – bedframe and mattress, cupboards and chests of drawers, a bookshelf – and immediately after seeing the state of the kitchen she’d bought her own minifridge and electric hotplate to keep inside her half of the house. But even if she could be self sufficient in the basement, that didn’t change the fact that they lived together. And since Gwendolyn knew what the upstairs looked like in comparison to her basement, the knowledge that the kitchen likely had families of cockroaches whose lineages dated back through a complex cockroach geneology made her soul ache.
Cringe. No other word for it. But she needn’t concern herself with that now. As she downloaded the new file, her thoughts only fantasised about what a pretty and good maid she’d be, for a beautiful old manor house somewhere, where all she would have to worry about was keeping everything neat and tidy and orderly.
The soft voice spoke through her noise-cancelling headphones as she lay down in bed after stripping her clothes off, a soft dildo already in her hands in preparation. The delicate feminine voice slithered forth from the audio file, gently guiding her into a dreamscape of stories. Gwendolyn sighed dreamily as the trance took hold. No need to think anymore. For now, she could relax.
Now that it was the weekend, Gwendolyn Winters was hoping to take the opportunity to relax.
There was a new movie showing at a local theatre, thankfully not another disposable cookie-cutter superhero movie. With all her careful planning of her finances, she’d decided that maybe a little splurging was acceptable. Even if her heart wasn't truly invested into the movie, she could use the excuse to get out of the house.
It was only as she was about to leave that her hand tightened into a fist at the sound of a familiar voice.
‘Hey Gwendy-chan, you got a minute?’
Gwendolyn sighed. God, she hated that nickname.
‘What’s up?’ she called back, still mentally preparing to leave.
Then she heard it. The sound of a glass hand-bell, ringing so clearly through the house.
‘Come here, Gwendy-chan. I won’t ask again.’
That bell. She recognised the sound. It was tied to a suggestion from the maid files she loved, one that made her feel compelled to obey any order given to her following the sound.
She stormed into the house, fingernails digging into her palms as she tightened her fists. What the fuck was Wallace playing at?!
The bastard was sitting where he usually was, dressed in a t-shirt bearing a graphic depiction of an ahegao face he’d worn for three days straight and canvas cargo shorts for almost twice as long. He kept himself propped up in a comfortable slouch against the couch by a particularly lewd body pillow. And his expression, holding a delicate glass bell, was one of absolute smugness.
Gwendolyn spoke first.
‘What the fuck is that,’ she demanded.
‘Just a little thing I picked up,’ he snickered, ‘I’ve been thinkin’ about what you said a week ago and you know what, you’re totally right. Some things do need to change. And I was just thinkin’ maybe we can start by giving you an attitude adjustment. And those little files you seem to like gave me an idea.’
Gwendolyn gawked at Wallace.
‘You fucking…’ she began, almost too angry to speak, ‘You looked at my browser history?! That’s a huge invasion of my privacy!’
‘So’s letting you into my house, Gwendy-chan,’ Wallace snorted, ‘And despite my hospitality you’ve done nothing but insult me and my humble abode.’
‘I pay you, motherfucker,’ Gwendolyn was screaming now, ‘And besides, that’s kind of what renting is! And what fucking hospitality?! You never take out your trash any further than leaving the bags next to the door, and I can’t even use the kitchen with how much of a mess it is!’
‘And I let you use my wifi. So really, you shouldn’t be surprised that I know when I can see your whole download history, Gwendy-chan,’ he smirked, relishing the enunciation of that insufferable name.
Gwendolyn gritted her teeth, ‘You unbelievable son of a-’
‘Good maids only speak when spoken to, Gwendy-chan,’ Wallace suddenly interrupted, ringing the bell for good measure.
A hot flash of shame overtook Gwendolyn’s emotions, as she flinched and looked down at the floor.
Fuck. No, no, no, no! This couldn’t be happening! She couldn’t let this smug, useless fucking loser take advantage of her!
She wanted to scream at him more. She wanted to verbally and physically beat the shit out of him. But the words would not come. Her body would not move.
‘Tsk tsk, Gwendy-chan. I mean come on, you really think I didn’t notice? How every time after you yelled at me for something dumb only you cared about, I could hear you cumming your brains out in your bedroom ten minutes later?’ Wallace giggled maliciously before making that horrible sucking gut laugh that made her skin crawl, ‘You're such a baka! I know you’d never admit it, but you wanted me to mess with you for so long, didn’t you? Why else would you make it this easy?’
She wanted to tear her own skin off as she could only grit her teeth harder.
‘But, ah, yare yare, we can’t have you cleaning up dressed like that,’ Wallace continued his stupid fucking monologue before ringing the glass bell, ‘Get naked, Gwendy-chan.’
The fire inside cooled to cold, bitter shock. He was serious. Holy shit. This wasn’t … he couldn’t … she shouldn’t…
She tried to keep her hands from moving as they started to drift to the hem of her sensible cardigan. Tried.
The fact that she was even moving, the fact that she was blushing, that was all humiliating enough. If it were anyone else, it would have been so hot that her conditioning had sunk so deep. But not him. Anyone but him.
Wallace made another of his horrible laughs, ‘You’re such a tsundere, Gwendy-chan. Fufufufu~’
Gwendolyn would have done anything to make him shut up. But right now, she was struggling to stop herself from unbuttoning her own blouse.
‘But hey, I’m not gonna make you clean naked yet,’ Wallace leered, ‘In fact, I bought you a super kawaii outfit to wear! I’ll go get it now.’
Wallace stood up and left the living room – likely the most physical exercise he’d get today – leaving Gwendolyn to strip on her own. Why? Why was she still doing this? She hated what she was doing and yet…
She could ignore these suggestions if she really tried. She knew she could. All the safeties in the files made sure she could. Why wasn’t she using them?! She pushed another button through its hole, her face growing redder and hotter.
Gwendolyn wanted to stop. She already wanted to find a new apartment, but…
Gwendolyn's train of thought was interrupted by Wallace slamming into her back, his greasy hands feeling up her breasts.
'Oh man, these are just so soft! You're really lucky to have such nice tits, huh Gwendy-chan?'
She couldn't contain it any more. It took all her willpower, but she turned and shoved Wallace away, causing him to stumble backwards away from her.
'Shut up! Just shut the fuck up!'
She was already feeling excessively humiliated. This was beyond too far. Technically Wallace had just assaulted her. Gwendolyn's breathing was hard, her neatly braided hair already out of place from her barely restrained rage.
Wallace looked up at her, his own expression a dark anger.
'You shouldn't have done that, Gwendy-chan.'
Too late, Gwendolyn saw the bell in his hand. She tried to put her hands over her ears to block out the noise, but the ringing compelled her.
'Kneel.'
As her body obeyed, her brain roiled with the urge to fight back. Why was she allowing this to happen?! Why was she doing this?!
Wallace just strutted closer to her before ripping off her bra.
'I knew from the start you wanted me to fuck you. When you started yelling at me after I was watching Shōjotengoku Keimusho, you looked so desperate to fuck it made you look stupid. You're so whiny,' a pathetic but throaty growl escaped from Wallace, 'But I'm kinda into that.'
Wallace stuck a thumb down the front of his cargo shorts and pulled them and his underwear – possibly the only clothes he was wearing that were actually washed ... hopefully – to show his unshaved cunt.
Gwendolyn shivered in disgust and anger.
'I might let you pleasure me, little Gwendy-chan, if you're a good girl,' he continued to posture, 'But we need to fix some itty bitty widdle pwobwems wif youw bwainy-wainy.'
Fear once again bubbled out from the simmering cauldron of Gwendolyn's indignity as Wallace pulled his cargo shorts back up. She had to fight this. She had to-
The glass bell rang clear through her ears once more, and compelled her to obey.
'Good maids always call me Master-san. In fact, they don't just call me that, they think it too.'
Gwendolyn had to fight it. She refused to call him that, with every fibre of her being. She wasn't going to. She didn't want to stay another second here. All she wanted to do was pack her stuff and move far away, somewhere that Master-san could never-
A strangling sensation filled her throat. That likely wasn't even how Japanese honorifics worked! She hated this unrepentant, insufferable, useless goddamn weeb!
'In fact,' Wallace rang the bell again, 'You should only think of yourself as Gwendy-chan from now on. I guess you can still pretend to use your other name for your job or whatever, but we both know what you really are.'
It was as if Gwendy-chan could feel herself melting out of sheer humiliation. No, god, please no! She didn't want this! Anything but this!
'Finish taking off your clothes, slutty little baka,' Wallace snickered, 'I've still gotta get your pretty outfit.'
Once Master-san had left the room again, Gwendy-chan let out a choked sob. This had to be a nightmare. Some terrible result of falling asleep during a hypnotic induction. But she felt compelled. She removed her skirt, her tights, and her panties and...
To Gwendy-chan's horror, she was hard.
That had to be the worst part of it. Her own humiliation from Master-san was bad enough but this?! She didn't want to enjoy this! If Master-san saw her erection he would...
Gwendy-chan gulped hard. She didn't want to know what he'd do to her. But that was an inevitability now.
Master-san sauntered back into the room, holding a clotheshanger with possibly the gaudiest outfit Gwendy-chan had ever laid eyes on. It was a hot pink maid outfit, made out of some awful semi-reflective PVC material the black ruffles at its edges yet cutesey studded collar with attached bell around the neck giving it this horribly fetishistic look. And of course it had black cat ears. Of course it had fucking cat ears poking out of the maid headband. A pair of matching long socks were pink and black striped and of the same material, but Master-san had seemingly been too cheap to pair the ludicrous outfit with any kind of footwear. But that wasn't what held his attention at the moment.
Right now he was staring lecherously at the one thing Gwendy-chan hoped he'd overlook.
'I knew I was right, but it's so nice to feel validated by your body,' he said, stepping closer and raising one of his bare feet, gripping the head of Gwendy-chan's cock in his toes.
She couldn't conceal her expression. Gwendy-chan's face morphed into pained disgust, feeling Master-san's dirty fucking feet touching her in the most vulnerable, sensitive, and exposed part of her body. He squeezed it with flexes of his toes and the intensity of her displeasure only grew.
'It's so cute how angry you look,' Master-san grinned, 'So maybe I'll let you keep hating me. Not like you can do anything about it.'
His toes squeezed harder on the head of her cock, and Gwendy-chan let out a gasp of pain. He laughed like he was struggling to breathe, and let go before swiftly putting the cat ear headband over her head.
'There you go, Gwendy-chan! Now put on the maid outfit like a good little tsundere.'
She squeezed her thighs together as she hesitantly took the uniform from Master-san. The material felt cheap and flimsy, like it would rip itself apart just from her wearing it for a few weeks. She slid it on over her head, her skin prickling with displeasure at the act as the stretchy material contorted into the shape of her body. She wanted to wake up. She wanted to wake up and escape from this. Anything to forget this ever happened.
When she passed her head through the neck hole, Master-san had something else in his hand. Something Gwendy-chan didn't want to see.
A fucking tail plug.
'Why do you look so surprised? All good neko maids have tails, silly Gwendy-chan,' Master-san cooed.
Gwendy-chan sat back as she slowly pulled on the garish PVC kneesocks. She wanted to spend as long as she could without that thing in her ass. But once she'd put the second sock on and brought it over her knee, Master-san planted a foot to her chest and pushed her over, exposing her tight hole.
She heard the bell again.
'Be a good neko maid, Gwendy-chan, and relax for me. Neko maids can't feel right without their tail.'
Against all impulse, she felt her body obey Master-san's words rather than her own brain. Master-san knelt, pressing the lubricated plug against her. Gwendy-chan was shocked at how easily it slid inside her little neko hole and-
No! She didn't think that! She didn't-
Gwendy-chan gasped in pleasure as the tail went inside all the way, seating inside her comfortably. She mewled needfully, pathetically, hopelessly as she saw Master-san about to ring the bell again.
'You'll end all your sentences with a cute little "nya" from now on, won't you sweet little Gwendy-chan?'
She desperately wanted to hold her words back. She wanted to stop, she wanted to do anything but what she was about to do. Instead, her mouth eeked open and she said in a faltering whimper; 'Yes Master-san, nya~'
Master-san all but squealed in delight, 'Ah, so kawaii! So dere!'
Gwendy-chan balled her hands up into fists. The sound of the bell rung through her head again.
'Time to get up Gwendy-chan, if you do a good job cleaning I might let you eat me out.'
Her indignity burning with incandescent brightness, Gwendy-chan pushed herself to her feet. He didn't even care about how clean his place was, the asshole!
Gwendy-chan needed to clean. She had to clean now. Master-san wanted her to clean. That was her job as a neko maid.
Master-san chuckled in satisfaction as he watched her getting up.
'You know, I think you should be like this every day when you come home from work. You really like working, so this works out for both of us, doesn't it Gwendy-chan?'
She couldn't keep her words out of her mouth.
'Yes Master-san, nya~'
'I always knew you'd like this,' he said, slapping her ass as she passed on the way to the kitchen, laughing at her yelp and stumble.
Gwendy-chan was overwhelmed by feeling. Rage. Indignity. Desire. Need. Hate.
She stared into the kitchen. It was like staring into an abyss.
The smell hit her first. Rot from who-knew how many different plates and bowls and containers, fast food bags soaked through with rancid oil, droppings from animals and insects, and she shuddered to think what else. A weeks-old plastic cup of bubble tea had turned utterly curdled and mouldy, sitting perilously on the edge of the countertop.
From the living room, Gwendy-chan heard the TV turn on and some kind of obscenely loud and obscenely kinky hentai start playing, Master-san shouting to her to be heard over it.
'Gwendy-chan, we're out of garbage bags! You should go to the store and get more.'
Hours later after she had finished cleaning, Gwendy-chan was back in her basement, where Master-san said she belonged when he wasn't using her body or giving her chores, still dressed in her pretty maid outfit, on her knees next to her bed facing the wall, her head bobbing back and forth against the dildo Master-san told her to worship until he wanted her.
Her thoughts were a stew of violence and lust as she gagged against it, feeling the silicone shaft sliding in and out of her throat, each self-inflicted thrust emphasising each of her thoughts.
Fucking! Lazy! Asshole! Stupid! Fucking! Smug! Garbage! Loser! Idiot! Useless! Cunt!
She’d been told not to touch herself. Master-san’s word was law. But she felt like she was so hard, she would melt if she could. She wanted to cum so bad, but she could only do that if Master-san said she could.
And there was no fucking way she going to beg that goddamn loser idiot for permission to cum.
Gwendy-chan forced the dildo to the hilt down her throat, a few small tears squeezing out of her eyes as another bead of precum dribbled into her soaked panties. Master-san said he wanted to sniff her panties while he went to bed, so she should make them nice and fragrant for him.
The mere thought of it made her feel like she could cringe herself out of existence.
That is some very silly fun. Really enjoyed reading it. I have a soft spot for stories about Doms that aren’t cunning and domineering, but idiots, stumbling into a great situation for them, that they don’t deserve. Looking forward to more from you.