Trial of Five Ch. 04

Wyndi was surprised that she could remember everything when she came to. She remembered that she was undergoing her trials to become a knight, she remembered this was all to determine her order and caste, she remembered this was her fourth trial, and she remembered the other three that came before...

That last part made her blush. In fact, she was still coming down from that last one. Her thoughts still felt a bit syrupy and her pu- lady spot was still agonizingly achy and molten. Wyndi sighed, pushing the sensation towards the back of her mind and tried to catch her bearings... Or, well, she gave a very good attempt at doing so.

She found herself in a... city. It wasn't one she recognized, but that wasn't saying much, Wyndi effectively grew up behind the walls of Fort Dawnlight and hadn't ever really been to a city before. The closest thing she got was Brassbell, and that place barely even counted as a town.

So, naturally, Wyndi gawked a bit. Everything was so big! And the streets were made of actual stone instead of worn dirt! And the people! She'd never seen so many people in all her life in total and here there were more walking down a network of busy streets in a motley of colors, styles, and... genders...

Wyndi frowned at that last thought. She felt as if her mind was insisting upon it but it felt... uncomfortable. Jagged. Like a puzzle piece that only kind of worked being forced into an empty slot. The more she tried to focus on the people around her, the more she was sure they were all women and... and like she couldn't really comprehend their faces, that they just became a blur that her brain refused to register. She also couldn't shake that same sensation of awkward familiarity when she looked at them.

You're thinking about this too hard, the thought popped into Wyndi's head. It's a trial, weird things are gonna happen, Wyn.

Wyndi sighed and nodded to herself at the logic. The exact elements of the trial weren't important, just that she figured out what she was supposed to do in it... Not that her track record had been so good thus far. Besides, thinking about the actual mechanics of it all hurt her ditzy little brain. She wasn't meant to-

She growled and forced that line of thinking to puff into mist as she began to get a move on down the street. She would not fall into the habit of just accepting what the trials were doing to her. Sure, they had their effects and she recognized that, but that didn't mean she had to just take them lying down. And she could start by figuring out what the hell she was here for.

Wyndi came to a stop as she caught her reflection in a shop window. She was wearing a brown uniform with a buttoned shirt she had tied off just below her breasts and a pair of shorts that barely reached mid-thigh. Around her waist was a belt with rolled-up parchments, envelopes, letters, and other written items. The outfit was pretty cute, actually, and Wyndi couldn't help but lean into the reflective glass to get a better look as she re-adjusted her ponytail.

A courier, she realized. I'm dressed like a courier. So... she was meant to deliver things? That seemed easy enough. Wyndi grabbed at one of the parcels around her waist and looked at the address inscribed on it. She expected herself to be confused and have no idea where that was, but instead she was surprised to find that she knew exactly where it was in this city. Strange.

As Wyndi began heading that direction, she mused a bit more. Each trial had done plenty to mess with her head. They all gave her new memories and thoughts to grapple with, and this one clearly did that too. But why did it let her remember everything this time? That seemed... cou... count... counterin... Counterintuitive.

Her brain throbbed trying to force the right word into existence. It was like her very being was trying to force her to accept simple thoughts were better thoughts. That just made Wyndi grumble in annoyance and-

"Hey, you! Why don't you strut your way over here, babe?" said a purring, yet firm voice. As distracted as she was, Wyndi didn't realize she'd heedlessly listened and wandered over to the alleyway she'd heard the call without bothering to even look up. And when she did, her breath caught and her heartbeat quickened.

Standing before her, was a beautiful young woman with snow-white hair. For a moment, despite being able to register her gorgeous face and features, Wyndi once again felt that strange sense of almost-recognition, but that was quickly snuffed out as her eyes drifted lower and she saw the dress that the woman was wearing.

The neckline was low--plunging, in fact--with a corset that hugged her waist and accentuated her tits and ass. It was slitted along the sides from the hem to her hips, revealing long and milky bare legs. Wyndi found herself unable to look away as the woman ran a delicate hand along her stomach and up her chest. It was only then that Wyndi realized she'd been summoned over by a street whore. And she had listened.

"Um, hi," was all Wyndi could think to say.

Whore's lips curved up into a mischievous smile. "Hello there. You seem... a bit frazzled."

Wyndi gulped. "Um, yes- I-I mean, yeah. Busy and all." She felt stupid with all her stuttering and stumbling. It was just a woman. A really, really, hot woman whose pillowy tits jiggled ever-so-lightly and prettily and she coquettishly laughed at Wyndi's response.

"And maybe a bit stressed too?" Wyndi nodded. "Well, I'm quite good at alleviating those things with my services."

It was then that Wyndi came back to herself and she remembered what she was actually supposed to be doing. "Um, actually... I'm sorry, but I really need to go deliver these messages. Couriers never rest and all." She tried a weak laugh. Whore just tilted her head.

"Oh? Then why did you come over?"

"Well... you called me over."

"And why did you listen?" She smiled as began to run a flirty hand of Wyndi's bare stomach, playing with her belly-button. Wyndi reached up to brush her away, but hesitated. It felt nice and she was about to leave anyway, so what was the harm?

"Surely you busy, busy couriers can spare a few minutes to enjoy yourselves?" Whore fluttered her eyelashes and Wyndi couldn't help but blush and look away.

"Um..." she said, then let out a slight squeak as the hand on her stomach lowered, hooked itself around her belt and pulled her in closer.

"Oh, you're an adorable one, and soooo pretty too~"

Wyndi nodded in uncertainty. "U-um, thanks, but I really need to get going."

"Just relax, babes. Those letters aren't going anywhere. Enjoy yourself for a bit, hm?"

Wyndi breathed heavily. Whore smelt sweet. Very sweet. That perfume was... Wyndi couldn't put a finger on it. All she could focus on was the pretty woman standing uncomfortably, wonderfully close to her and the insistent throbbing in her loins that had yet to lessen since her first trial. She could stay for a little bit, right? Just enough to take the edge off.

No, she forced herself to think. She had a duty to do and Wyndi wasn't going to let any distracts keep her from doing this trial right.

"I'm really sorry, but I have to go," she said firmly.

Whore gave a sad smile that almost made Wyndi change her mind. "Of course, darling, of course. Oh, and I just love your little uniform, by the way."

Wyndi couldn't help but smile. "Thank you! But I see what you're d-"

Before she could finish the sentence, Whore leaned in and drowned Wyndi in a passionate, wet kiss. She gasped but couldn't find the will to pull away as their lips began smacking against one another. She sighed and felt everything begin to get fuzzy and spinny.

When Whore finally pulled away, her hands were firmly wrapped around Wyndi's waist, the fingers pressed against the flesh in such a way that it sent a shiver down Wyndi's spine. "There, didn't that feel good?" Wyndi nodded. "And it feels good to feel good, right?" She nodded again. "So, why not enjoy yourself for a while?" She began pulling Wyndi further down the alleyway.

"But..." Wyndi began. "My job..."

"Will still be there when we're done," Whore said reassuringly. "Besides, it's just so much work isn't it?"

Wyndi tilted her head in confusion.

"All that running back and forth. Messages here, letters there. It's a lot. Tiring, isn't it?"

Wyndi sighed and nodded again as Whore nuzzled her neck and planted a kiss on the crook between her throat and shoulder.

"And it doesn't feel good to be so tired and physically worked up. It feels good to relax. To do things that make you happy."

Her hand found its way to Wyndi's crotch and began rubbing at it through her pants. Wyndi, in turn, found herself grinding into the touch.

"And would fucking me making you happy, Wyndi?"

Wyndi whimpered. It would. Oh gods, it would. She was just so worked up and needy. She needed release finally. And the thought of walking all across the city all day suddenly seemed so exhausting.

"Y-yes."

"And would it make you feel good?" Whore whispered, nibbling on Wyndi's earlobe.

"Uh-huh..."

"You should do things that make you feel good, dear."

"I... I want to..."

"And does sex make you feel good?" Whore's other hand began to unbutton Wyndi's shirt.

"Yes."

"Say it," Whore said firmly, driving her thumb along Wyndi's clit through the fabric.

"S-sex makes me feel good!"

"Good girl. You know, I want to feel good too..." She kissed Wyndi on the cheek and pulled away from her. Wyndi blinked at her in confusion. "This deal doesn't just go one way. If you want the pleasure you crave oh-so badly, I need some first." She pulled the bottom of her dress to the side, revealing her own glistening pussy. "Eat me out, pet. If you want what makes you feel good, that is."

She said it so simply that Wyndi almost didn't question it. Almost. "But... you're the whore. You eat me..." She trailed off as Whore raised an eyebrow, her expression growing cool.

"So? I should get something out of this too, shouldn't I? How is it fair that you get to cum and I don't? Do I not deserve to for my hard work?"

"N-no, I didn't say th-"

"Then eat. Me. Out." Whore said each word with a breathy tone and a sense of finality. It was further accentuated as, with each pause, she squeezed one of her own breasts, causing Wyndi's mind to just about short-circuit.

Her thoughts were ditzy and simple again. She wanted to figure out why this all felt off, but couldn't manage to and instead, slowly, stepped up to Whore and lowered herself to her knees. Wyndi looked up with large, helpless eyes and Whore nodded encouragingly as a hand on the back of Wyndi's head guided her towards the cunt right in front of her.

Just get it over with so you can get yours and finally think straight, Wyndi thought as she closed her eyes and began to lick and suck.

A satisfied coo came from above her, as well as a little laugh. "Gosh, it was that easy, huh? You're such a people pleaser, little courier."

"Mph," Wyndi said as she continued. Whore tasted divine and she quickly found herself getting into the activity, trying to make the woman above her feel good. A gasp and moan told her she was doing well.

As Wyndi continued her cunnilingus, the hand on her head gripped harder and pushed her face deeper. Her voice grew more faltering and husky. "O-oh, yes! Just like that, girlie. Mmm... You're good at this. Do you like making me feel good?"

Wyndi nodded as her mouth worked.

"It feels good to make me feel good?"

She nodded.

"You should feel satisfied for doing such a good job. Are you satisfied, Wyndi?"

She nodded again.

"Mph! A.. aah. Y-yes! Soooo good, so so good. Too good. H-how are you this good?"

Wyndi responded by running her tongue over Whore's clit.

"Oooooh! I think I know. You just love sex."

Wyndi nodded absently. She heard what Whore was saying, but didn't bother thinking too much about the words as she continued her task.

"Obsessed with it, aren't you? Y-you need it. Everyday. And... and when you're n-not doing it, you're thinking about... about it. C-can't get it out of your head."

Wyndi just kept nodding. Her mind was blank, better to not upset Whore and let her think she was paying attention.

"Imagine if... if you got to d-doooo it all the t-time!" Whore was reaching the edge, Wyndi could tell. "Just sex non-nonstop! N-nothing but f-feeling good and... and m-m-making others f- Ooooh, fuck... Feel good."

Wyndi slipped her fingers into Whore's slick hole and began pistoning them in and out.

"Shit! W-would you like that, b-babe? Would that be... be nice?"

"Mhm!" Wyndi said enthusiastically, though she hadn't processed what had been said. A moment later Whore exploded in Wyndi's mouth alongside a howling moan of ecstasy. Pride swelled within Wyndi and she beamed.

Whore took several deep breaths, then giggled. "Then you definitely chose the right profession!" She pulled away and Wyndi opened her eyes. When she did, everything was different.

Whore wasn't wearing her dress anymore. Instead she wore a courier's uniform. A respectable one, not the revealing excuse that Wyndi was wearing. She looked down to readjust it, only she wasn't wearing the uniform anymore. Instead, it was a slutty, revealing dress that only a common street harlot would wear. But... that wasn't... Whore was-

Her mind fuzzed. For a moment, everything felt strange and incomprehensible. Nothing made sense and Wyndi felt as if her entire being was in flux. Then, the moment was gone and Wyndi remembered everything. She was a whore. She'd always been a whore, ever since she came of age. It only made sense with how often she fucked. Sex was an eternal companion in her mind and she was, admittedly, quite the people pleaser. If she could do something to make someone feel better, she did it, no questions asked, no matter what it was.

Whore- No, Courier finished buttoning her pants up and reapplying her belt. "Thanks, skank. Needed that." She fished out a coin and flicked it at Wyndi. She caught it gratefully, but looked at Courier in confusion.

"But... What about me?"

Courier raised an eyebrow. "What do you mean?"

"Aren't you going to go down on me now?"

Courier tilted her head back and let out a laugh. "You? Why would I do that? You're a whore, slut. Your job is to give pleasure, not receive it." She smiled and gave Wyndi a patronizing pat on the head. Courier's pussy juices were still dripping down her chin.

"Oh... right," Wyndi said, looking down as her cheeks burned in shame.

Courier giggled to herself again. "So sex-obsessed that you forgot the main role of your job. Oh, that's just the cutest thing I've ever seen." She pinched Wyndi's cheek, which only made her blush harder.

Courier smirked, then lowered herself down to Wyndi's level and whispered in her ear, "Don't be down like that, skank. You chose sex over duty, now you have to deal with the consequences."

Wyndi frowned, not knowing what that meant. So, in response, she just whimpered, rubbed her legs together to try and ease some of the passion between them, and looked up at Courier with begging eyes.

The woman just laughed. "Sorry, slut. Got a job to do, can't waste any more time." And, with that, she left Wyndi alone in the alley, whistling as she walked away.

Wyndi sat there for a while, her thoughts slowly growing more and more tinged with arousal and fucking until that's all she could think about. She tugged and pinched at her nipples, but that only made things worse.

You chose sex over duty, now you have to deal with the consequences.

Why did that line keep echoing in Wyndi's slutty mind? For a moment, she felt a familiar sensation. She felt like she was standing on a wall in the storm. The wind and rain threatened to push her off into the abyss and she felt like she had two choices: Fall deeper or latch on to something.

Her crying pussy made the decision for her.

Wyndi the whore stumbled out of the alleyway and flagged down the first woman she saw. It didn't take much encouragement to get her to follow Wyndi back into seclusion. In moments, she was furiously kissing the woman as she groped and kneaded Wyndi's breast. All the while, Wyndi moaned like a bitch in heat.

"Wow, it feels like you need this more than I do," the woman said.

Wyndi nodded desperately. "I do! I really, really, realllllly do!"

The woman chuckled and began guiding Wyndi's hand beneath her skirt. At the same time, her fingers found Wyndi's pussy and began to pump.

Wyndi gasped and saw stars. She began working her own fingers with a fervor born out of sheer gratitude.

"Oh yeah, just like that bitch."

Wyndi wept in joy as she trembled and rested her hand on the woman's shoulder, her free hand still massaging Wyndi's tits.

"You like that, do you?"

Wyndi couldn't muster words anymore, so she just nodded and mewled.

"Then I'll give it to you. Again. And again. And again. And again. Over and over until my little sex kitten is satisfied."

Wyndi gave a petulant whine at the phase, but couldn't bring herself to care as the fingers within her worked in and out, in and out, in and out, and oooooh.

She bit her lip and continued to weep. Finally. After so long, she was going to cum. She could feel herself rising to the edge. It would finally all be over. All the frustration and struggling and not having sex. She didn't need to worry anymore. She didn't have to fuss about her stupid trials...

The trials.

Wyndi sighed. She wanted to scream, both in anger and pleasure as those wonderful fingers brought her mere millimeters over the edge. She could have let them. Could finally get her satisfaction. Instead, she grabbed the woman's wrist and pulled the hand away.

"I've come this far. I can't stop when there's just one trial left." She smiled sadly to herself and looked up at the woman, who was now Courier once again. "I'm choosing duty."

Courier gave her own smile and gave Wyndi a pat on the cheek. Her demeanor was far gentler now, though Wyndi wasn't sure why. "I'm afraid you already made your choice in this trial. But, that doesn't bar you from undergoing the next one."

"Wait, what?"

A million questions flooded Wyndi's mind. Looking into Courier's eyes, she now saw something ancient and ethereal. There were answers there, tools to help guide her in her final trial.

Courier must've seen this in Wyndi's expression, as her smile deepened and she cocked her head. "Maybe... Maybe it will be you."

"What do you me-?" But before Wyndi could finish her sentence, the wall behind her turned into a white void and Courier pushed Wyndi into it.