Tiny Tinder Academy – The Resort: Sisterly Surprise

“Okay”, the waitress said as Caley finished unpacking one of her suitcases, “Here you go!”

“That’s great!”, Caley responded, shutting the dresser drawer. “Could you put it on that table on the balcony?”

She gestured with one hand, but the waitress was already moving toward the massive glass doors that led outside. Caley had spent some serious money getting this room, but she already knew it would be worth it. Before she’d even gotten to her room, she’d been pampered and given the best screwdriver she’d ever drank. The blonde had been slower than she liked unpacking, but she’d used her time wisely: finding her perfect tiny in the catalogue before someone else could rent him.

Caley lifted the suitcase and wheeled it into a closet the size of her bedroom at hom. At 5’0”, she felt small in the massive room, but knew something that would instantly make her feel large for the first time in her life. The waitress asked politely if she needed anything else, and Caley shook her head.

“Enjoy your stay, miss!”

Despite the object of her desire waiting on the balcony for her, Caley took the time to unpack the rest of her belongings. The rest of the vacation would be pure fun. She could spend five minutes to be more organized.

Finally, after some time, she sighed and took a sip of her screwdriver and looked out at the balcony and at her cup.

“Here we go”, she said, slipping her shorts and shirt off. The slender blonde felt heat between her legs at the thought of what she was about to do. A cool breeze from the ceiling fan flittered across her small breasts and her nipples immediately stood at attention.

Daintily, she walked onto the balcony and felt the summer heat against her naked chest. A glance around showed her dozens of other balconies that also overlooked the resort’s massive pool area, where dozens of people were lounging in various states of undress. At least two of the sunbathing women were openly masturbating not far from an already entangled couple, and it was obvious this was a place where everything went.

Caley felt herself relax as her balcony neighbor, an older brunette wearing a comically large hat and nothing else, waved to her. She waved back while a tiny man walked carefully along the balcony railing in front of the woman. Then she turned her attention to her prize.

Knowing it was probably useless, she leaned forward and peered through the hole on top of the golden container. It was too dark within to see, but she could hear excited yelling from within. Smirking, she picked up the cup and sat on the long beach chair.

Before she could stop herself, she wrapped her lips around the top of the container and tilted it back like a shot glass.

***

Zac yelled with excitement when the light above changed suddenly. Looking up, he saw a massive blue eye, but nothing that could tell him who his giantess was. It somehow seemed familiar, but most of his family had blue eyes, so he’d seen a lot of them in his life. In his excitement, he found it odd that he was thinking of family, so he shook his head and refocused.

Then the light vanished and he felt the cup moving. There was a flash of sunlight, then sudden darkness.

“What is--?“, he started to say before his world flipped upside down.

With a surprised scream, he fell onto something hot, wet, and soft. Instantly he was lifted upward and slammed against the roof of the giantess’ mouth. Another flash of light illuminated the world outside and he got a narrow view of the resort and the retreating golden cup before her lips sealed him away from the outside. Adrenaline exploded through his body and Zac pushed aside the urge to scream in fear as the giant predator’s mouth was suddenly darker than any night he could imagine.

Rough suction pulled at his body, making his ears pop as the tongue explored every inch of his body. Despite himself, Zac laughed and tried to yank his shorts off, but he was too slippery and his hands couldn’t get under the waistband in the confusion. His excitement and the sudden change in surroundings had him too disoriented to do more than let out gleeful shouts.

“Hey, gimme a minute!”, he yelled, laughing, knowing she probably couldn’t hear him.

Then he felt himself be moved sideways and his legs landed on something sharp. Vaguely familiar laughter sounded from all around, so loud he felt his bones vibrate.

Teeth?, he guessed, just as the top row of molars came crashing down on his legs. He shrieked in anticipation of the immediate amputation, but instead he simply felt a strange pressure as the massive pearly whites tried to cut him in half. They retreated, then returned, smashing onto his torso as the giantess did her best to make him a meal.

Finally, Zac guessed she’d had enough, and he had too. Terror had given him an incredible erection, but he was sure he’d had his fill of being chewed on. Before he could even realize she was done chewing, the massive lips opened and he felt himself tumbling through her open lips and back into the golden cup.

Before he could forget, he yanked off his shorts. Quickly he started rubbing himself, then forced himself to hold back. He wanted his first orgasm here to be inside his giantess, not inside a cup.

The next several minutes were electric with anticipation; he felt his container be moved and shook gently, but nothing involving him had happened yet. In the distance, he could hear some moaning and gasping, and he could only guess what it meant. And hope it meant his action would be starting soon.

Then he was knocked off his feet when his container was grabbed suddenly and yanked upward.

“Whoa!”, he shouted, not expecting the sudden movement.

The giantess clearly didn’t care and he found himself, almost impossibly, getting even harder from her lack of consideration. Through the opening up top, he saw a flash of blonde hair and pale skin before the container was tilted sideways, but not quite enough to dump him out. A belly button flew by, a mile of smooth skin, and then he saw it.

“Yes!”, he screamed, unable to restrain himself.

She had positioned him perfectly at her entrance; a massive pair of hairless, glistening lips awaited. It was now obvious she’d been playing with herself in anticipation. Zac found himself grinning like an idiot, eager to slide inside this giant woman. Then he had a realization: his container was shaped like it was for a reason.

***

Satisfied that she was sufficiently ready, Caley aimed the container right at her pussy. She hadn’t been sure how she wanted to see her toy the very first time, so she’d elected to use him before he even knew who she was. The golden funnel at the top of the cup would serve her purposes perfectly.

The diminutive blonde moaned with pleasure as the narrow top slid into her, and she pushed it as far in as she could comfortably. It wouldn’t work very well as a dildo, but she didn’t need it to. Before she could think any more, she tilted her hips backward and lifted her feet to her ears. This had the result of turning the cup upside down completely and she felt, with great delight, something small fall out of it and into the deepest parts of her sex.

Instantly, she felt her body spasm in reaction, and the shudder of a small orgasm ran through her as she gently pushed the golden object free. It fell to the floor with a silent thud as her fingers sought out her clit. A silent cry of pleasure escaped her lips as her sensitive bud leapt to life when she finally gave it the attention she’d craved. And the meal her pussy had been yearning for ever since she’d had her most perverted idea ever.

Zac fell with a happy shout, bouncing off one soft, wet wall and landing hard on what he knew had to be the giantess’ cervix. Instantly, he was overwhelmed with her scent, and he tried to stand only to fall forward as her hips shook. His hands pushed on smooth hot flesh and he looked up at a sudden flash of light. For a moment, he could see the entirety of her tunnel, pulsating and glistening, as his container was pulled free. Then the path to the outside world slammed shut, leaving him in humid darkness.

The walls of her pussy closed in on him and Zac felt instinct take over. He knew that he didn’t need to breathe, but his lungs were telling him he would run out of air momentarily. He knew that she couldn’t crush or harm him; but being surrounded by pulsating, gripping flesh struck fear deep into his heart.

Despite all that knowledge, claustrophobia struck.

Before Zac knew what he was doing, he found himself pushing toward her opening in a frenzy. She was incredibly slippery and he couldn’t tell if he was making progress, but the walls around him quaked and gripped and squeezed constantly; even if he wasn’t moving forward, he knew his giantess was loving it. For his own part, he wasn’t quite sure if his love of the situation and finally fulfilling his fantasy was going to outweigh his instinctive, overwhelming fear of being buried alive.

Caley barely kept herself from crying out in ecstasy as her toy moved within her. With a focused thought, she made him slightly smaller to keep the fun lasting longer, but as her finger flew across her clit, she knew her orgasm wasn’t far away. The feeling of a tiny man struggling inside her was incredible; she’d used vibrating eggs before, but they had nothing on this. Reflexively, she clamped her muscles around her little toy and felt him push even harder against her.

With a silent gasp she came, feeling herself squeeze down even harder on the tiny man. While she writhed on the tanning chair, she felt him surge forward, using the sudden tightness of her walls for traction. She let him push his way to her opening and widened her legs just as the peak of her orgasm passed. At the perfect time, she looked down to marvel at the suddenly appearing hands and arms; she came again from the view of a tiny man pushing his way out of her snatch and leaned backward to moan in pleasure s the rest of his body slid out of her and dropped to the chair.

With her breasts heaving, she caught her breath as the sunlight shone down on her. The day was too far along for the sun to be shining in her eyes, and she found herself staring at the blue sky as her heart slowed it’s racing. There was a faint tickling as the tiny brushed against her legs, surely hoping to catch a glimpse and actually meet the giantess who now owned him for the foreseeable future. With a sigh, she realized she could put this off no long: the only part of her vacation that made her slightly nervous.

And excited.

No matter how it went, she’d still have her fun, of course. But this was the only event that she knew she wasn’t completely in control of, and that irked her. Whether on stage dancing or in a relationship, Caley liked to be in control

Zac jumped and yelled again, entranced by the view of the gargantuan vagina that he’d just pushed his way out of. Now that he was free and unharmed, as promised, part of him wanted to climb back inside and bring this incredible woman to pleasure again. But he knew he had to meet her. If she was effectively going to own him for the next couple weeks, he had to at least know her name, even if she was one of those giantesses that enjoyed ‘permanent’ insertion.

Which he had technically put on his list of interests. Along with pretty much everything else, no matter how unlikely it was to actually occur.

Then she sat up, a mountain of pale, beautiful flesh. Her toned stomach came into view first, and he could tell she was fit, petite even, but had admirable abs. Then her breasts, small but proportionally larger to the rest of her body, then finally he saw her face. Long blond hair draped over her back, blue eyes adorned her face, and –

“What?!”, Zac yelled out, recognizing his sister. His erection died instantly as he yelled, and she giggled at his obvious discomfort. He felt the faux wood under his feet shift as he grew slightly, until he could see over each of her toned thighs. A careful step took him further away from her glistening pussy and he suddenly realized he was covered in her juices. The scent that had intoxicated him minutes ago suddenly filled his nostrils and caused him to shudder with disgust.

“Caley!”, he screamed in frustration, furious that she was here, on what was supposed to be his vacation. Something he’d spent years planning and saving for. And now, at the ultimate completion of his wildest dream, the giantess who’d rented him for his entire vacation was none other than his older sister. Not a supermodel. Not a rich girl taking her twelfth vacation this year. Not a housewife looking for a toy to abuse while she hid from her family.

His sister.

“What the hell are you doing?!”

“Well”, she said with an infuriating laugh, “I’m playing with my new toy, of course!”

Zac yelled wordlessly, furious and ashamed at the same time. How could she do this to him?

“But really”, she explained, putting on a face of fake contrition, “I was snooping through your room like a terrible sister and found your tickets. And since I’m doing so well, I thought, I could use a little vacation!”

“No! This was my vaca-“, Zac yelled, but Caley’s voice easily overrode his. His earlier fascination with being disregarded vanished as she effortlessly shut down his complaint.

“I really think this is gonna be great for me”, she continued with a smile, “I needed a break.”

One hand wrapped around Zac and he realized he was now almost seven inches tall. He was abruptly lifted upward and Caley leapt from her chair. She waved to a woman, sitting alone on her balcony and patting her mouth with a napkin, before she skipped into her room. If Zac hadn’t been so enraged, he would have appreciated how luxurious of a room she’d rented.

Instead, he found himself angrier with every pure white pillow and spotless mirror that he saw, and he drew in a breath to –

With a laugh, Caley fell onto her back on the bed and scooted upward until her head was supported by the pillows. Her hand lowered until Zac’s squirming form was inches from her pussy again. Caley bit her lip as she anticipated how good this was going to feel.

“Let’s face it bro”, she said with an innocent look on her face, “We’ve both got this tiny fetish, the extra kink with my toy being you is just icing on the cake. And you can enjoy it or fight it, but either way, I’m gonna enjoy myself.”

The massive blond gently bit her lower lip, and before he could respond, she pushed him face-first into her cunt. He pushed against her tender skin and swung his arms to avoid pushing his face into her, inadvertently striking her clit and causing her to gasp at the shock. Gently pushing his now-larger body into herself, she adjusted her grip around his waist and moaned at the vibrations and sensations his swinging arms were giving her.

Deeper and deeper he slid until finally, Caley only had a grip on his ankles and she could feel the gentle thumping inside that had to mean he was pushed up against her cervix and hitting it furiously. His pulsing fight sent shivers through her entire body in a way that no normal size man could ever compete with.

“Damn Zac!”, she said, rocking her hips unconsciously as she held him deep, “If you’d have told me you were into this, we could’ve found a way to make it happen years ago!”

“No!”, he cried out, only hearing her heartbeat as he pushed against her cervix. Furiously, he struggled to keep his face clear of her secretions, but he knew it was a losing fight. Her fingers were wrapped around his ankles and her pussy clung to every inch of his body. It was everything he’d wished for and more. Except for one thing.

“Caley! Let me go!”

Unhearing and uncaring, Caley started to pump her toy in and out of her pussy. With each thrust, a new sensitive spot was brushed and she felt more powerful than she had ever imagined. Her brother’s entire life had lad him to this moment: to be so powerless against her she could treat him like a literal dildo. Driven as deep as she could push, Zac wiggled in ways that no vibrator could ever match and Caley knew, without a doubt, that this would be the greatest vacation ever.

Two hours later, Caley finally released her hold on her brother’s legs. She’d changed positions multiple times, sized him up to uncomfortably large twice, and felt like her heart was ready to explode. Twice shed’ made him so small she could feel him slip all the way to the back of her love tunnel, only to slowly grow him and writhe in pleasure as he filled her walls from within like a living, vibrating egg.

She wanted to continue; the sensations he gave her were addictive in the best way. But she was exhausted. Each new orgasm was almost too much for her and she realized that she’d been staring at the ceiling twitching in a constant state of bliss for the last ten minutes. Using all her willpower, she decided that she was finished.

For the moment.

With a groan and a flick of her hand, Caley slipped her toy out of her exhausted vagina and dropped it to the bed spread.

Thoroughly beaten and used, Zac tried to crawl away from his sister. He’d been pounded and crushed and squeezed for what seemed like an eternity; his sister’s pussy had been his entire world and it seemed as though he’d been forced to explore every inch of it. Unharmed but exhausted, a testament to the shrinking toughness process, he stumbled to his feet and tried to run on the crumpled sheets.

Instead, her hand wrapped around him once more. He screamed, but her thumb covered his face and he felt the sensation of movement. His body was swinging wildly as she walked, his feet kicking on open air. When the thumb vanished, he had to cover his eyes from the setting sun reflecting from a higher window, and she placed him on the railing of her balcony. Instantly, he dropped to his knees and grabbed the railing; his fear of heights had kicked in and the thought of dropping miles into that pool below was horrifying.

“So, listen Zac”, Caley begun, her voice hoarse from moaning, “I wasn’t kidding when I said you should enjoy yourself.”

He turned and looked at her, and despite himself, he could appreciate how attractive she was. She was a stunning petite blonde with a body that spoke of hard work, not simply skipping meals. If she was literally anyone else, he would have been thrilled that she was the giantess who wanted him.

Caley felt so satisfied that she didn’t care at all that she was outside naked; it had made her nervous earlier, but now now. And especially not since she could see several couples hooking up on their own balconies. Far below, next to the pool, most of the clientele were as naked as she was, though most of them were simply content to tan without tan lines.

“So I really hope you can relax a bit and make this good for you”, she continued. Idly, she started braiding her hair, her fingers flying in rapid movement as Zac tried to creep away from the edge of the railing. “You got the good package, after all. Everything I can think of, we’re gonna do and that’s that.”

Zac held still as she picked him up again, feeling himself shrink in her palm.

“Caley! Just give me back so someone else can rent meeee…!”, he yelled as she tossed him up in the air. With a scream, he fell back down and she caught him with her open mouth, careful to stop his body on her tongue and not swallow him - no matter how much she wanted to.

Humming to herself, she went back into her room to change and Caley couldn’t help but smile. With her brother tucked into her cheek, she picked out her tightest yellow bikini and slipped it on. The one rule she knew she wanted to follow here, at least for a little while, was thus: If you were naked, you were fair game to anyone who wanted a piece. If you were wearing clothing, there had to at least be some form of consent.

And for the first night, at least, the only guy getting up in her business was going to be her tiny brother.

Though as she lounged at the pool among the rest of the guests, she knew she’d have as many men as she wanted in her business.

***