It Helps to Be Cute

Story by Picklessauce69 on SoFurry

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A commission for False_Princess


"Uh, what..." Sleep still hung in a heavy blanket over Argol as he tried to lift his eyes up under the glare of the sun above, not buffered by the usual protection of his room back home. A hand rubbed up to his eyes, trying to force the lingering grogginess to fade as he peered through partially opened lids to the grassy slope around him.

"W-what?" He blinked, waking up now as the confusion of his location began to settle in. He glanced down at himself, half expecting to see something terribly wrong with himself, but he still wore his drab brown pants, belt, tunic, and boots. He seemed unscrathed.

"Where am I?" He mumbled allowed, pushing his messy black hair from his face while sitting up to get a better look around. He could see the edge of a town meeting to this field which seemed to be populated with lazily grazing sheep. He squinted, not recognizing the skyline of this city. "I don't know where I am..."

But before his confusion could intensify, Argol heard a soft charm from a nearby bush before a scroll came rolling out from beneath the cover of the foliage. It unfurled itself and the words began to echo out around him.

"Welcome player! You're now Contestant Number Nine! Your reward for winning this game will be your life only, but shall you lose... you won't be returning home! Before the fun begins, you'll have a single day to find a Familiar in our land and garner magical abilities. You've been awarded starting funds-" A small sack of hefty coins appeared with a clunk by the scroll. "Shall you fail to gain some powers, you'll find yourself eliminated swiftly as the games begin. Good luck, Number Nine. Your day begins now."

Argol stared down at the writing on the scroll. The black inked words matched what had boomed out around him, but he still could barely believe it. "A game? A strange world? My death!?" He jumped to his feet realizing that strange or not, this game would have to be dealt with as though it was the most serious thing or not! If his life was on the line, he'd need to find a familiar!

Argol heaved himself onto his feet and headed towards the edge of the town, moving towards the closest building that appeared to be a small shop. The windows were full of wears, baskets and woven bags though in the midst of it all sat a pair of smooth, deep red flats that a simple, crisp band over the top that'd cradle the foot inside. He squinted for a split second at them, noticing how they didn't match the display before he moved on, "I've got to find useful supplies and find a familiar-" He started silently wondering where he could find someone with potent abilities. "Maybe the forest or the mountain..." He scanned the horizon, counting the hours he had to find someone.

"I'll need food, a sac..." He headed towards a store that read, GENERAL, on a withered sign above it. The door chimed as he entered and he began to pluck out some cheap, high calorie foods to fuel him for the day.

"A rope might come in handy," He mumbled, reaching onto the high shelf, blindly grabbing for the edge of the rope he glimpse from below, but as his hand searched instead it slipped over the smooth top of silk finished shoes.

"What?" He muttered, looking up to see the same pair of shiny, red flats. His head shook with annoyance. "Maybe the trend in town?" He grabbed the rope beside them and hurriedly checked out though as he left, a tiny voice in the back of his head wondered if they were a trend for a reason, they were a bit cute?

But the thought vanished quickly as he packed his fresh supplies into his pack and started across town, scanning through the shop windows for someone or something that looked interesting.

"A map, I'd love a map..." He thought to himself, finding his eyes roving through shop windows now on the opposite side of town. "I'm running out of options-" He rounded back, going back into the only shop that had any maps in their display.

He found one wrinkled, local map of the mountain ranges nearby but not before he spotted the shoes again gleaming in the sunshine of the shop. This time, at the sight of them, his boots suddenly felt heavier than ever. "Those would be so nice and light..." He mused to himself, feeling a fleeting urge to slip them on, but he grabbed his map and fled back onto the street.

"God, of all the familiars I could find, I'm being followed around by some cutesy, silk shoe wearing one!?" By now, he knew that the shoes couldn't be coincidence, but he didn't want the magic of some fluffy, girly caster. "I don't want to magically apply lipstick, I need to be able to protect myself!"

He marched off towards the mountains in the distance, carrying his map. As he reached the trees and consulted the page for the first time, the shoes appeared on a smooth topped rock just as he took a seat on it. He shook his head, letting out a puff of irritation from his lips, but the sun was shining atop the shoes and they gleamed with perfection. For a moment, his fingers twitched on the map, fighting the urge to just stroke over the smooth top of the flats. "I bet the insides are so smooth..." But he focused on the map, plucking out of a cave to explore before he leapt back onto his feet and headed off.

But as the early sun began to dip towards evening and he still hadn't found anything that hinted towards a hiding magical power, he found himself rounding back towards town, grumbling with growing frustration for his situation.

"I can't find a single familiar besides some cutesy shit?" Argol thought to himself, stamping his boots hard to the dusty ground with every step. "I bet those shoes wouldn't be so heavy!" He thought just as they flickered onto the spot just ahead in a clearing of trees, resting atop an old stump.

Argol groaned, looking up to the sun, for now still high in the sky, "I can find a better familiar!" He thought with firm determination. Though his boots were aching on his feet. He longed to take them off and swap them for the smooth, soft insides of the dainty shoes there in the opening of the trees.

"No!" He told himself, walking past the shoes with his eyes set forward. "I've still got time! I still have daylight!"

He headed back to the edge of town, this time heading into a salon in the hopes of picking up some gossip about a magic caster or someone that could point him towards a familiar. Surely, someone might know something in this town. He plucked up frothy ale, listened into the conversations around, and waited for information to reveal itself.

But as the ale turned warm and the sun dipped more, Argol hadn't learned anything besides which men in town frequented the naughtier clubs in the evenings and had gambling debts. "This is hopeless!" He thought, walking into the street only to see the shoes waiting on a bench for him, as if knowing his frustration was growing.

He scoffed, pushing the urge to slip them on out of his mind as he strode past though he could see them perfectly in his mind now. The sheen of the smooth red silk, the soft padded look of the inner sole, the dainty strap over the center of the foot. They were simplistic, elegant, and cute.

He looked down at his boots, heavy and coated in dust, and suddenly didn't like them so much.

Mere hours of daylight returned and Argol didn't have a direction to search in anymore. He was tired, but he trudged towards an old worn down building at the edge of town, hoping for a classical witch to hobble out and grant him powers, but the building was just abandoned and empty when he arrived, save for a the pair of smooth red shoes, now glinting in the falling moonlight that told him his time was running out if he was going to have any familiar at all.

"Fine!" He snatched up the shoes, finding the silken surface was soft as butter beneath his fingers. "Show yourself! I know you're a familiar and you've been following me! Show yourself! Owner of these shoes, show yourself to me!"

A second passed before a soft, pink puff of smoke filled up the edges of the cabin and then the space in front of Argol no longer sat empty. The girl that appeared stood maybe five foot, but certainly nothing more. She had bright blonde hair pulled up into two twin pigtails on either side of her head, tied up with pink ribbons and white ruffled stockings that decorated her ankles before a matching pair of the red shoes covered her small feet, but otherwise not a shred of clothing covered her body.

Her petite frame was marked with small, perky breasts on top with her nipples a brilliant rosy hue in the chill of the night and a smooth, plump lower pair of lips beneath her smooth, subtle curves. "Argol! You've resist my charms all day long!" She gave a little clap with faintly jostled her tits. "You've really proven yourself to be worthwhile for a companion of mine! You'll get to have your very own pair of shoes for your steadfast nature with none of the negative effects, but first... you have to seal our pact!"

She took a step closer to him with a click of her little shoes on the old wood before she rubbed the smooth sole up the length of his calf. It tickled faintly across his skin, but the silk was slightly warm from her feet inside and it sent a zip up his spine.

"I want you to prove yourself willing to join this pact." She gave a firm nudge to his shoulder, forcing him onto the ground. Argol didn't resist, knowing this was his only chance to gain some protection for whatever came after this in this frightening game! His knees just settled onto the wood and his eyes tipped forward to where the red shoes were, resting on her feet.

She slid her shoe up the length of his chest, nudging the smooth silk over the lump of his cock in his pants which was inexplicably growing harder and harder at the touch of her shoes. He told himself it was merely her nudity, but his eyes were watching the gleam of the red silk, not her pale naked form.

She pivoted, raising her toes higher in their soft shoes and rubbing the front end along his cheek, nudging them to his puckered lips before she pushed her way inside. "Kiss them, prove to me that you're not just picking me out of desperation. You have to earn these shoes, truly want them..."

She gave a little giggle, watching as his lips pushed out into a kiss, speckling the smooth silk with small pecks of his mouth. The silk was smooth underneath his kisses, almost slick. He tried running his tongue lightly over the smooth silk, wondering how it'd feel entirely in his mouth. She pushed his lips apart, giving him his wish as he suckled at the toe-end of the smooth shoes before she pulled back, giving him the sole for his soft kisses. The rougher bottoms of the shoes still intrigued him.

"Come on, Argol. Prove it to me-" She gave a small spin, settling down onto a wooden seat behind her and propped her feet up onto an aged ottoman as her full, round eyes watched him. "Worship them, the source of your potential power. Show me that you deserve them, that you want them-"

Argol's cheeks were growing hotter and pinker now, hoping no one could see as he crawled over towards the shoes. His lips continued to kiss up the side of the smooth silk as he nuzzled his cheeks into her sole. "Mmm-" Another little giggle escaped her upturned lips. "Now take them off me, fuck them, and seal the pact between us."

"F-fuck them?" Argol mumbled, a little squeak of surprise leaving his lips, but he knew he needed this familiar, plus his cock was aching inside his trousers. Did it really seem so much trouble to feel the soft inner soles of the shoes? Surely not.

He gingerly cupped his hands around her heel, sliding the shoes off from her small feet, feeling her warmth still radiating out from the inner padding. Then, he yanked at the ties of his pants, grabbing for his throbbing cock before he forced it eagerly, almost hurriedly into the opening where her foot would sit and slamming himself up into the warm, closed space for the toes.

"Oooh-" A soft whine left his lips, almost un-summoned. He felt a rush of heat tickle down his body at the caress of the soft, worn inside of the smooth flats. The girl watched with glittering eyes, leaning back into her seat with a playful grin playing on her lips. Argol, without her prompting, slipped his fingers into the other shoe and started to stroke the top, exposed length of his dick with the bottom sole of the shoe, alternating between the soft silk of the side and the rougher bottom of the shoe. His cock was pulsating, throbbing with every thrust up into the warmth of the toes. He could feel the indents where the castor's toes had sat and the warmth there was the strongest, he shoved his tip into the smooth dip, fucking harder into the sole of the shoe.

His fingers inside the other shoe curled, making the toe-end firm as he started to stroke himself from the base with the shoe, loving how the rough base felt before the smooth reprieve of the silk. He bit at his lip, fighting his own impatience now.

Then, with no more warning that a catch in his throat, he thrust once more and a spurt of cum shot into the end of the toes. The cum smeared into the soft insides of the shoe and began to soak in quickly. Another pump emptied him completely into the heel section before he finished, panting, and looked up at the cutesy girl.

"You've done very well, Argol." She clapped, waving her hands and returning a pair of shoes onto her feet, though the warm, cum-soaked pair remained on Argol's crotch and hand. "Now, those are yours-" She chuckled, smiling. "All broken in!"

"Now, you'll be able to share my powers, level by level." She waved her hands, brightening the small cabin as night fell with a glow of pink around them. "First, you'll gain two passive abilities, Cute Clothes! And Swap Trap!"

She stood up, giving a little courtesy before her nudity was sudden covered by a full skirted gown in layers of pink and brilliant, snowy white. "The caster is always adorned in cute, girly clothing. If ever, heaven forbid, you're forced into something else, the clothing will change over time and negative effect will be shed."

She stepped towards him, running her fingers down his rough, dusty tunic before she gently cupped his cheek, "And Swap Trap! When the caster and target are in an intimate situation, the caster can swap clothing with the target-" She leaned in, pressing her warm, pink lips to his with a sudden rush of heat before she pulled back, now wearing his tunic down her body, drowning her in the fabric while Argol was hugged into the bodice of her gown with the shoes from his hands and groin suddenly on his stocking'd feet. "Just like that!" She giggled, quickly transforming his old clothes back into a form of cute and layered gown of rusty red and pink.

"You'll also, at this level, have a few castable powers: Conjure, Charming Shoes! Charming Knuckles! And Charm!" She walked around him, surveying the way the gown hugged and fit to his body perfectly with a grin on her lips. "You'll be able to conjure any cute shoes, heels included and charm non-hostile creatures with them, into wearing them, anyone wearing them will become a friend! In the same vein, Charm will allow you to make a target more agreeable and friendly the cuter and sweeter you are to them!"

Argol was starring, trying to absorb this list. "And Charming Knuckles?"

"That ones fun! If you're wearing charming shoes on your hands, they'll be potent weapons for your protection!" She clapped, glancing at the high moon. "Now, your first day is nearly finished, but before the true challenges begin, I think we need a little tutorial, huh?" She giggled, clicking her heels together.

With a sudden flash, they were back in town in the fading evening light. People bustled to and fro, but for now no one really noticed the pair of them in their frilly garb. "Now, see that woman-" She gestured to a woman leaving the business center. She wore a tight fitted pencil skirt that fell just below her knees and stockings that rose to meet the skirt, plus smooth, leather pumps that were simplistic, but subtle cute. "We need to turn her to the fold, so to speak-" She gave Argol a little pat, "This will be your training, go turn her to our charming ways, huh? Shouldn't be too hard, she is terribly pent up after a day in the office, oof!" With that, and a final giggle, the caster faded away leaving Argol alone in his gown staring at his assigned target.

He felt a fresh tightness in his chest where the bodice of the gown hugged in around him, but if felt somehow safe to be hugged in such a way. He surely couldn't explain it, but the space of the skirt made his cock feel free and the tightness on his chest made him feel safe. "Now, I have to somehow turn this business woman?" He glanced around, noticing how many people were truly in this square. "I'll have to be... cute!" He leapt forward, stumbling a little bit on his smooth bottomed shoes. His cheeks were already taking on a cutesy pink glow while he made his way towards her.

"H-hello, Miss!" Argol gave a low curtsy in front of her, tilting his head with a cute blush blooming over his cheeks. He grabbed onto the edges of his skirt, trying to grab them in a little curtsy to act all the cuter.

Now he could feel eyes onto his back as the woman looked at him with shock. "W-what do you want?" She demanded. Argol gulped unsure of what to do before he remembered all the spells at his disposal, suddenly holding up his palms as a pair of smooth, pink pumps materialized on top of them. "I thought you might want these?" He stammered out, trying to maintain a cute, lilting tone as he offered up the Charming Shoes, but she just shook her head. "No, certainly not."

"Charming Failed!' Argol thought, thinking back to what the caster had told him, the woman was very pent up! Argol looked up at her, this time looking through a veil of his own thick eyelashes as he bowed his knees slightly, trying to look as cute as he could manage. "I couldn't help but notice that you must be leaving work, any interest in blowing off some steam with me?" He looked up, biting one of his plump lips before he leaned in towards her, hesitating a beat before his lips impacted to hers and his passive Swap Trap took action!

Suddenly, the woman was no longer squeezed inside her pencil skirt, Argol was! He felt his ass clenched inside the tight fabric while the woman was covered in the frills of his heavy skirts. A blush now colored her cheeks. "It's working!" He told himself gleefully, letting out a cutesy giggle on instinct.

"You're very forward-" She mumbled, but no longer with such hostility in her voice. Instead, she seemed softened to his charms now as she stepped a bit closer. The crowds passing them all glanced over, taking a beat to notice the grown woman, with wisps of pre-greying hairs from the stress of her job, wearing the lolita style gown of a little girl leaning into the chest of a young man wearing a tight fitting business uniform.

"How odd-" Someone muttered, skittering off towards their evening plans with passing judgement.

Argol had a mission though, he had to complete his charms of this woman and practice all his new abilities in preparation for the day ahead when the game truly began. "Are you sure you wouldn't love these shoes?" Argol raised the pink pumps again. "They'd really match?"

Now the nagging urge to wear the charming heels caught the woman. She couldn't resist. She slipped out of the smooth flats that Argol had swapped her into and held up a stocking'd foot. Argol smiled, sliding the shoe onto her smooth feet. One after another she slid into the pair and then a bright gleam tickled over her lips. Now she was surely under his spell, charmed by him and the shoes on her feet.

"Mmm, you know what-" She whispered, licking over her lips that were growing ever pinker to match her shoes. "I do think I want to blow off some steam with you, little boy." Argol felt color flooding to his cheeks as one of her hands found the front of his skirt, grabbing the bulge of his cock beneath the tight fabric with a practiced squeeze. "I want to suck this cock of yours, right here."

Argol felt his cheeks growing hotter, but how could he resist? Would he fail his initiation then? Instead, he just leaned into her touch, trying to disguise it from the passing people within a hug. "I want you to cum right into my mouth and let me swallow it down-" She started to slid down his body, stroke over the black vest of his outfit before her lips began to kiss over the smooth top of his navy business skirt. Her fingers caressed up the black stockings he wore to match as he cock grew ever harder beneath the skirt, tenting the tight front of the pencil shape.

She dropped to her knees on the cobblestone, oblivious to the passing people. Argol tried to shuffle them closer to a bundle of foliage in the dimmest part of the street light's coverage, but a second glance would expose them in the public street. The business woman didn't't seem to care at all. Her head was bent in focus in front of Argol's skirt. He could see only the glossy black of her hair and the wisps of fading color atop her scalp.

She lowered onto her heels, with her heels sticking up behind her under the curve of her ass in the skirt. Her fingers slid down Argol's front, balancing herself as she slipped her head down the edge of his skirt, wriggling it right beneath the hem of the pencil skirt. Argol's eyes went wide, suddenly feel the warm and tickle of her hair against his bare thighs before her lips found the tip of his cock, spreading wide with hesitation and grabbing onto him with a warm clench of his mouth.

To people passing, a quick glance would miss the bulge in the front of Argol's skirt of the business woman's head bobbing there. He tried to look elsewhere and not grab onto the lump of her head as she slurped up and down the length of his cock, but he struggled to focus on any mission as she gulped and slurped up the length of his shaft.

"What happens if someone really noticed?" He asked himself, knowing that there was glances over their way, noticing something amiss with the young man in the business garb with his skirt bulging with the head of a grown woman in frilly lolita wear, but no one had said anything to him, thankfully.

The woman just kept sucking. He could hear the catch of her breath under his skirt, but she was focused solely on suckling the flared tip of his cock. Her ass was bouncing and writhing under the lolita, frilly skirt as she worked and the upturned bottoms of her heels were wriggling as she moved. Argol watched the bulge of her head work, slurping up and down his length, over and over again. She kissed her lips right up the base of his cock, letting his thrust down into the curve of her throat before she pulled back and gulped the length of his cock down again.

Argol struggled to keep some composure, to not draw anymore attention, but he was fighting a winning battle. The woman was sucking him with such excitement and strength and the whisper of the wind on his back only reminded him that they were just in the public street. Anyone could see him now as the woman sucked him to his base, working to milk him of every drop. "Does it matter?" He asked himself, "if this is just a distant world for some game? Surely not!"

He couldn't resist, his hips started to buck into the heat of her mouth, pushing the bulge of her head in his skirt harder. He almost wondered how the fabric could handle so much motion pushing it back and forth. He reached down as she sucked, grabbing for the skirts of the lolita dress she wore and lifting it up, capturing a glimpse now of her bare ass before the sight of her upturned heels bobbing with every suck of his cock.

Her throat tightened around him, gulping around his tip as Argol fought the throbbing and pulsing of every heartbeat. Her lips were suckling so tightly atop his head, slurping him in atop her tongue with unwavering interest until he just couldn't hold back any longer.

His balls were churning, pulled tight to his body as the first explosion shot from his tip. Cum burst against the business woman's throat, spraying right down her gullet. Then, she pulled back, letting him shoot onto her tongue and coat the insides of her cheeks. She gulped down every drop, slurping at little as she cleaned up the tip of his cock before she pulled back, emerging from his skirt with her hair in a mused birds nest. She just smiled, giggling a little before she gave a small nod and headed off down the street with her heels clicking as she went.