Trial of Five Ch. 02

Wyndi woke up in bed feeling disorientated.

Sitting up, she rubbed her head and looked around to find herself... in her bedroom? Yeah, that was definitely right. But why did the room feel so unfamiliar? Something in the very back of her mind told her that this was off, but the more she tried to grab at it, the further away it got.

You just had a bad dream, Wyn. That's all, she thought. It helped.

With her affairs in order, Wyndi climbed out of and rummaged through her wardrobe until she found something worth putting on. She settled for a tight pair of black denim shorts and an equally dark top that cut off just above the naval. She blinked as she examined herself in the mirror. It was... awfully revealing. Since when did she wear things like that? And... since when did she like it?

Wyndi shrugged. It didn't matter. A little skin never hurt anyone, plus the attention it brought wouldn't be unwelcome. Maybe it was about time to try something new—and a daring, rebellious-looking outfit was just the way to go about it in Wyndi's estimate. Satisfied, Wyndi nodded to herself in the mirror and went out the door.

She found her roommate in the kitchen.

Wyndi stumbled for a moment. There it was, that disorientation again. She glanced at her roommate and frowned. She... knew this woman. The dark hair and mature features were different but the face was the same. Where had she seen her before?

She blinked.

Of course Wyndi knew her. They'd been living together for the past three years. Why in the world would she be confused about knowing who she was? Wyndi and... and... What was her name again? Wyndi furrowed her brow. She couldn't muster up her roommate's name for the life of her. Strange.

"Good morning, Wyndi!" her roommate sang upon noticing her standing there. "Sleep well?"

"Uh," Wyndi said, sitting down at the kitchen table. "I guess not? I feel weird this morning."

"Weird how?" the woman said. She placed a mug of hot tea down in front of Wyndi, briefly looking her up and down. The woman's expression slipped into a frown for a mere moment before snapping back into its usual state of chipper merriment. Wyndi felt a pang of self-consciousness but immediately dismissed it. Who cared if her roommate disapproved of her outfit? They were Wyndi's clothes and she'd decide what she wanted to wear.

"I don't know," Wyndi admitted, picking up the mug and taking a sip. "I just woke up and everything felt... off."

"Like deja vu?"

"No. It's different somehow."

"...Huh. Wanna talk about it?"

Wyndi waved a dismissive hand. "It's fine. I'm sure you've got a busy day."

"Nope! It's my day off, actually."

Wyndi raised an eyebrow, looking her roommate over. She was wearing tight pants and an even tighter blouse with too many buttons undone. Neither exactly felt like 'I'm just going to chill at home' garments.

Despite that, Wyndi shrugged and gestured to the chair across from her. "If you're sure."

Her roommate smiled and sat down, practically resting her massive chest down on the table as she leaned forehead with interest. Not that Wyndi was complaining or anything.

"Go ahead. I'm listening."

"Well, I guess I just felt like my head was real foggy when I woke up and there was this sense of... disconnect. Like reality wasn't fitting correctly." She winced. "If that makes any sense."

Her roommate nodded. "Maybe you were having an intense dream? I hear they can do things like that when you wake up from them suddenly."

Wyndi frowned in thought. "Maybe?"

"Focus and try to see what you remember. Drink your tea."

Wyndi did, closing her eyes. Yeah... she had been dreaming, hadn't she? It was about... about...

She blushed.

"Ope! Looks like someone remembered something!"

"N-no. It's... It's nothing."

"Come on now, tell Mommy," she said, her voice dipping into a husky drawl. Wyndi shivered. She couldn't deny that between that tone, her attractive figure, and the several years she had on her, Wyndi's roommate had a certain matronly quality to her that Wyndi couldn't help but find pretty dang hot. Her roommate abused it as often as she could.

"That has never once been funny," Wyndi said, glaring across the table.

Her roommate tittered to herself in amusement. "Oh come now, I'm sure it's not that bad. Tell me."

She sighed. "Fine. In the dream I... I was a maid and I served this woman. I was cleaning her study."

"Oh?" she raised an eyebrow then grinned. "Were you a sexy maid?"

Wyndi's flush deepened.

"You were! Oh that's just adorable!"

"N-no it's not!" Wyndi huffed, crossing her arms.

"I know, I know. I'm just teasing. Keep drinking your tea, it'll calm you down."

Wyndi begrudgingly complied.

"So what else happened?"

"I... I don't really want to talk about that."

"Wyndi," the woman said sternly, moving over to sit next to Wyndi, putting a comforting hand on her shoulder. "You know you can trust me, right?"

"Yeah, I guess."

"Then you know you can tell me what happened and I won't judge you, right?"

Wyndi nodded.

"Then please continue."

Wyndi gave a shaky sigh, drumming her fingers on the edge of the table, but nodded. "She was... staring at me, so I decided to, um, make it more appealing for her."

"Did you like it?"

"What?"

"I said, did you like it?"

"I... I heard you, I just-"

"I think you need some more tea." Wyndi's roommate just about picked up the mug for her and forced its contents into her mouth, prompting her to swallow, smiling fondly all the while. Wyndi didn't mind too much. It was helping her relax a bit. Plus, her roommate's pillowy tits were pressed right up against Wyndi's arm and she certainly wasn't going to complain about that.

"You were saying?"

"O-oh, right!" Wyndi stammered. "Yeah, I guess I did like it. Just a bit."

"Of course," her roommate smiled, tucking a lock of hair behind Wyndi's ear, causing a shiver to run down her spine. "That wasn't so hard, was it?"

"No," she admitted.

"There you go. It's easy to do what you're told."

"Righ- Wait, huh?"

"Drink your tea, honey. It's getting cold."

"Oh! Sorry!" She picked up the mug and took another gulp. Wyndi blinked. She was beginning to feel a bit weird, like her brain was... swimming. Or something. She could still think just fine, but figuring out what to do was getting hard.

"Um... uh..."

"So what happened next?" Wyndi's roommate asked. She was resting the side of her head on her palm while she affectionately ran a finger up and down Wyndi's arm with her other hand. It felt wonderful.

"I dropped the feather duster. On purpose," Wyndi said, perking up at the other woman's direction. The memories were coming to her much faster now. "And when I picked it up to tease my mistress, she grabbed me."

"Good girl~" Mo- Wyndi's roommate cooed. "Grabbed you how?"

"Around the waist. And... And by one of my breasts."

"Oooh, kinky."

Wyndi nodded. When had it suddenly gotten so hot in here?

"Go ahead and finish your tea, girlie."

"Yes ma'am!" She swallowed the remaining dregs of her drink and even licked around the edge to ensure she got every drop. Wyndi didn't want to disappoint her... her roommate. Wait, why would she care about that? They both paid to live here. Wyndi could do whatever she wanted.

"What did your Mistress do after she grabbed you?"

"S-she started to... to s-squeeze me and s-say dirty things about me and... and... ooh." Wyndi let out a slight whimper at the end as she remembered all the embarrassing details.

"Gosh, this seems to be really turning you on. Are you turned on, Wyndi?"

"N-no..."

"You know how I feel when you lie to me, Wyndillyn," her roommate said, voice suddenly stern. It made Wyndi cringe and wither for some unknown reason. Hearing the other woman disappointed in her, it was like a punch to the gut.

"I-I'm sorry!" Wyndi blurted. "Y-yes! It's turning me on!"

"That's a good dear," she said, kissing her on the cheek, which just made Wyndi melt. Why was she suddenly feeling like this? She was so confident and self-assured early. Now it was like she was some kind of shy mess with gratification issues. Wyndi decided she didn't care as her roommate gently pulled her in close and had her rest her head on a nice, soft pair of mammaries.

"You just love being an obedient little sub, don't you?"

Wyndi shook her head. "Uh-uh."

"Don't talk back to Mommy, darling. It's not polite. Haven't you noticed you've been doing everything I told you to since you've sat down?"

Wyndi nodded.

"And haven't you noticed you've been getting increasingly hotter and more turned on since you sat down, as well?"

Wyndi hesitated, then shook her head.

"Oh you haven't?" her roommate said. She sounded amused for some reason. "Well, let's find that out for certain."

Wyndi frowned in confusion. What was that- She gasped as she felt a hand reach down the front of her shorts and began feeling around her folds. "Let's see here..."

"Ah! I... S-sto- Ooh~!"

"Looks like someone's sensitive. That doesn't bode well for your claim, you know." The hand withdrew, then appeared in front of Wyndi's face. Enraptured, she watched as two of the fingers spread apart.

And a line of moisture, connected at either fingertip, dripped from between them.

"Seems like someone lied again."

Wyndi squeezed her eyes shut, stifling a sob. "I'm sorry! I'm so so sorry!"

"It's alright, dear. Mommy understands. Just make sure it doesn't happen again."

Wyndi nodded fervently.

"You know what this means though, right?"

"W-what?"

"It means if you've been getting horny at the same time as you've been following all my instructions, then doing as you're told turns you on!" She said it so cheerily that Wyndi almost didn't question it.

"Huh?"

"You're a little obedience slut for your Mommy, cutie."

What? No, that couldn't be right! Wyndi was cool, calm, collected, confident, and... and other 'c' words! She made her own decisions! She-

Her thoughts scattered as the hand returned down below and began circling around her clit, the fingers dancing across her pussy lips. Unconsciously, Wyndi began to buck up against the hand.

"There, there," a voice above her said. It... It was getting so hard to concentrate. "You're just confused, precious."

She was... confused? Yeah, that made sense. She'd been confused since she woke up. That's why she'd started talking with her roommate in the first place. Right.

"Mommy will help make everything clear." A pair of sticky fingers slipped past Wyndi's mouth. She began suckling like a good girl. "Obedience makes you feel good. You love feeling good, who doesn't?"

Wyndi nodded. The fingers slipped out her mouth and she began feeling a hand caressing her hair in substitute.

"It's so hard for you to make your own decisions, because they don't make you feel good. At least, not in the same way. Isn't that right?"

"Yes, ma'am!" Wyndi said eagerly. She wasn't quite sure what she was agreeing to, but it was hard to focus over the positively divine hand that was playing between her legs.

"Good girl~" Wyndi felt a spark in her loins at those words that only made the sensations there all the better. "And doing everything your Mommy says makes you feel extra good, doesn't it?"

"Mhmm mhmm!" Wyndi half-said, half-moaned. She was now wildly humping those fingers, but each time she thrusted forward, they pulled back. It was heartbreaking.

"Good girl. You look at you, so helpless. You can't make any choices without your Mommy, can you?"

"No, Mommy!" Wyndi squeezed her eyes tight, tears escaping. She was right on the edge, but those damn fingers wouldn't let her climax!

"You want Mommy to decide everything for you. What you do, what you eat, what you wear, when you cum~"

"Yes! Yesyesyes!" Wyndi said, more to the stimulation she was finally able to feel from those soft fingertips. But just as quickly as they appeared, they vanished. She cried out in anguish.

"Oh no, what's wrong baby?" Mommy said, her tone patronizing.

Wyndi's lip wobbled as she held back the urge to cry. "Mommy, I c-can't cum!" She looked up into the face of her Mommy, her eyes pleading desperately to the one person who always knew what to do.

"Oh my poor, slut," she said, cupping Wyndi's face in her hands. "That's because I haven't let you yet. Only Mommy gets to touch your special little flower, and only she decides when it gets to feel good. Understand?"

Wyndi nodded despite the dejection it caused her. She always listened to Mommy. "Yes, ma'am."

"Good girl. Now dry those eyes and smile for me. Mommy loves her little girl's smile."

Wyndi sniffled, but rubbed the backs of her hands over her cheeks and did as she was told. It made her feel wonderful when Mommy smiled down at her in joy.

"There's my sweet little thing. Now come on, there's a special surprise in your room."

Wyndi blinked, but quickly grew excited. A surprise from Mommy? For her? She practically beamed as she hopped off the older woman's lap and grabbed her hand like an eager child on Merrifest Evening, pulling her towards Wyndi's room.

"Well someone's a little impatient," Mommy laughed as they entered through the doorway.

Wyndi blinked. Had... had her room been so pastel before? She didn't have time to consider as Mommy stepped up to the wardrobe and pulled something out. "Tadah!"

It was a sickeningly pink dress. The skirt was cut incredibly short to the point that Wyndi was sure that her ass would peek out from below, and the neckline and bodice seemed engineered to push her tits up and together.

"Don't you just love it? Now you can finally get rid of that horrid punk outfit. It just doesn't suit you, you know?"

Wyndi felt a moment of deja vu. A real one this time. She once again felt herself on that ledge, feeling as if her next decision would dictate something important. Something critical. Besides, she liked her broody dark clothes, didn't she? They made her feel... confident... self... assured.

When had she ever been either of those things?

"It's amazing, Mommy! i love it, i love it, i love it!" Wyndi said, hopping in elation, clapping her hands together.

"Oh, I'm just so glad," Mommy said with a smirk. "Here, let me help you put it on."

And so Mommy did. She undressed and dressed Wyndi like her own personal doll, making sure to be as handsy as possible during the process. Once finished, she took a step back and admired the final result. "Oh you look just gorgeous, dear. Give me a twirl."

Wyndi did. The skirt immediately flared out, giving a full view of her ass and pussy. Wyndi didn't mind. She loved showing off. Especially to Mommy!

"Well, I'd say you're just the most delicious looking thing in the world."

Wyndi blushed and giggled. "Thank you. i... i don't know how to repay you for this."

Mommy's grin became downright wolfish. "Oh, I have an idea." She stepped over to one of the chairs in the corner of the room, then proceeded to unzip and lower her pants as she sat. "Eat me out, slut."

Wyndi obeyed without second thought. She dashed forward, dropping to her knees and burying her face between her Mommy's legs. She licked and sucked and nuzzled with her whole body and soul. It only took moments before she could hear Mommy beginning to pant from above.

"O... Oh, fuck. Th-that's good. That's a good girl."

Wyndi felt a fluttering in her pussy at the praise, but didn't let the ache below distract her. Maybe someone dominant and confident would take advantage of this situation to get some pleasure of their own, but Wyndi was neither of those things. She couldn't even dress by herself for crying out loud. So she did nothing but what she was told to as a hand grabbed the back of her head and pushed her deeper, smothering her in the most beautiful pussy she'd ever had the pleasure to lick.

Minutes later, Wyndi's face was coated in juices and she was commanded to stop as Mommy caught her breath. As she did, she looked down at her good girl, smiling in adoration.

"M-mommy?" Wyndi worked up the courage to ask.

"Yes, precious?"

"Can... Can i cum now?"

Mommy laughed. Someone else may have thought it sounded cruel, but Wyndi didn't. Mommy would never be cruel. She took care of hopeless, helpless Wyndi. Cruel people didn't do that.

"No, dear, you can't. Good girls aren't allowed to cum."

"Oh..." she deflated.

"But," Mommy said. "I can edge you for as long as you want."

Wyndi immediately perked up. "Really?!"

Mommy smirked and patted her lap. Wyndi climbed on immediately and squealed in delight as she felt a hand snake up her dress and begin torturing her pussy with soft, delicate strokes, her thumb barely even grazing the clit. Wyndi was a shivering mess in seconds.

"That's a good girl," Mommy whispered, kissing Wyndi on the forehead. Wyndi stared up at those deep dominant eyes and felt just so frustrated. But frustration was good! That meant she was being a good girl! And good girls obeyed! Wyndi loved obeying. "You would do anything I told you, wouldn't you?"

"O-o-of course i would, Mommy!" She nuzzled Mommy's bosom, twitching as she almost reached orgasm again only to have it denied.

"I'm just so glad to hear that. You can just be my perfect little doll. Shackled by obedience and denied release for forever and ever.

Wyndi sighed. Forever... That was a looooong time. Wyndi loved the sound of that. Even if she... she...

She missed her next trial.

She bit her lip. Oh right. That. Surely it wasn't that important, right? It was just some stupid knight ceremony that... that'd define the entire future of her career and duty.

Wyndi whimpered. Shit. That was important, but the hand between her legs just felt so. Dang. Good .

"M-mommy?" Wyndi forced herself to stammer.

"Yes, sweetheart?"

"Can... Can I g-go to my next trial?" Wyndi pleaded, she widened her eyes and pouted, hoping that would be more convincing. She'd never demand anything from Mommy. She was a good girl. But... she could still ask for things.

Mommy's ministrations slowed to a crawl as she seemed to be considering the notion. Wyndi's heart thundered in her chest out of fear she'd say no.

"Well, I suppose," Mommy sighed. "But promise me one thing, dear."

"Anything Mommy! Anything!"

"Promise me," she leaned down, tapping Wyndi on the nose. "That you'll always remember that good knights follow commands and always listen to their betters."

"Yes, Mommy! Of course!"

"Then run along, pretty girl." She kissed Wyndi on the top of her head then gestured towards the door.

Giddy, Wyndi climbed off the sinfully comfortable cushion of Mommy's thighs and scampered toward the door. Without a second thought, she flung it open and ran through the doorway.

Then promptly fell into a white void.