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Would You Rather: A Cautionary Tale

Summary:

Cautionary Tales is a series depicting the awful things that can happen to girls who are too naive or too trusting or too weak in a world full of men who are smarter and stronger than them. It is fictional, yet inspired by reality.

In this installment, Sophia Mugglesam — 15-year-old star of the Youtube channel of the same name — finally convinces her mother she's old enough and mature enough to handle the production of a video entirely on her own. Left to her own devices and alone in the house, Sophia decides to do a Would You Rather-style video with a randomly-picked fan from a post on Instagram...and accidentally picks a man twice her age, who has his own corrupt intentions for the video. Will Sophia be smart and mature enough to worm her way out of it? Or will she become just another cautionary tale?

(Not) filmed before a live studio audience!

Notes:

So, I finally had luck enough to dig up a bunch of my old story files, which included more information on the Sparkles Club, as well as this — the other Cautionary Tales story I wrote, but never posted because it simply wasn't relevant.

As with The New Ukulele, Would You Rather was written in 2018 when the star was 15 (she's 21 now), and is entirely fictional. Any resemblance to any persons living or dead is entirely coincidental.

(4/28/2024)

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It was the first time 15-year-old Sophia would be making a video with a fan, instead of her own sister...and the only time. The first time Sophia was trusted with handling the video all on her own...and the last time.

She was so excited and so proud of herself that she'd insisted her mom take Bella to a movie and leave Sophia to her work.

“It's okay, mom,” Sophia had said. “Take your time, really! I'm 15, I can handle this. You can trust me.”

Then, as soon as that door shut behind her mom and sister, Sophia's head began swirling. She was so grown-up now! So mature! Her mom trusted her for once, and all she had to do was be safe and smart about her next video and not let her mom down.

Little did her mom know that Sophia had already kept a few secrets from her. Her mom didn't know the video would be filmed with a fan being invited to the house, for instance. Her mom also didn't know about the contest Sophia had posted about on Instagram; “like this post before I delete it and I'll pick a random fan to film a video with me!”

A thousand likes, one deleted picture, and a shared address later, Sophia was about to meet with the lucky fan she'd picked. It was like she was on top of the world. Whoever it was hadn't had much on their Instagram – just some random pictures of plants, a guitar, a cat - but it couldn't be that bad, right? Everyone's nice on the internet, at least in Sophia's circles.

It was about 10 minutes after her mom's car drove away and left Sophia all alone that there was a knock at the door. Her heart leapt in her chest. It was time! She nearly tripped over herself and her own bare feet to get to the door, wondering who would be the lucky fan – and stopped in her tracks when she opened it.

There he stood in front of her. A few feet taller and twice as broad as Sophia was, dressed in dirty jeans and a band shirt. The scruff on his face told her he was nowhere near her age range, though some part of her actually thought he was kind of cute. He did look a little familiar, but Sophia couldn't really place his face from anywhere specific. She took a step back, her eyebrows frowning a little.

“Oh, hi,” she said. “Um, are you here for my mom? Because she just left.”

“Nope,” he said in a cheery, innocent voice. “I'm here for the video?”

Sophia quirked her head to the side. “Video?”

“Yeah, your Mugglesam video. You had a sneaky little contest on Instagram for it?”

“Oh! Oh, you're the lucky fan!” Sophia replied. “Okay...”

“Not what you were expecting?” he said with a light chuckle.

Sophia shrugged. “Well...”

“It's okay, I get that a lot. So...” He peered around her into the house. “Can I come in?”

“Yeah, of course! Follow me~” Sophia turned and led him inside the house.

Her head was so full of things - like wishing she'd set up her camera in the living room instead of in her bedroom - that she didn't even notice her nameless fan locking the door up tight behind him.

"Over there's the living room," she said, pointing as she passed it to the room with the fireplace where she'd filmed several of her songs and even a few videos with Bella. "But we'll be filming in my room, because I...already set up there. Oops."

"Oops?" His voice was like a baritone compared to her light, angelic one.

"It's no big deal," she said, trying to keep her hopes up. Then again, her hope was that it'd be another girl around her age. Not a boy. Not...a man. "You're already here anyway, let's have some fun!"

"I can't wait," he said, and meant it.

Then they came to Sophia's bedroom. Light purple like a lilac, her favorite color, bathed the walls and even some of the furniture. In between her bed and her desk, right against empty wall, was where she'd set up her 'studio'. A few lights, her digital camera, a special microphone, two chairs, and a table to set things on.

"Your room's pretty cute," he said as he followed her into it. "Way cuter when it's not on a little screen."

"Thanks." Despite herself, Sophia's cheeks went pink and she had to pretend she was fiddling with the chairs until it went away. "Um, what's your name, by the way?"

"I'm James," he said simply.

She turned to him and stuck her hand out. "Nice to meet you, James!"

He shook it, and held it a few seconds longer than he should've. But her skin was so soft and so warm. How could he not hold on for as long as he could?

Sophia pulled it back and used the same hand to gesture to the 'studio'. "So this is where we're gonna be filming. How do you feel about doing a Would You Rather video with me? You'll get to ask the questions and I have to answer them!"

James smiled at her. "I think that's a fantastic idea, Sophia."

"Awesome!" She settled into her chair and gestured for him to do the same. "Shall we get started?"

"We shall," he said with a quirk of his head.

Sophia turned on the camera with the flick of a little remote control, and waved to it. The same way she'd started so many of her videos. All of James's favorites, anyway.

"Hi, it's me, Sophia!" she said with a bright smile. "And this is..."

"Uh, James," he said with an awkward little wave.

"And today, we're gonna be playing a special version of Would You Rather with my lucky guest! But instead of reading questions, he'll be asking me questions and I have to answer them, okay, guys?"

"I've already got some good ideas," James chimed in. "And to make it a real challenge, let's say that, on some questions, I'll give you a choice between two things to do and you'll have to do one of them. Not just say what you would do. How about that?"

"Ooooh, like a dare!"

"Yeah, exactly. It'll be tough, but we can get through this."

"Okay, guys, let's do this!"

"So, my first question...would you rather..." He acted like he was deep in thought. "Would you rather be locked in a room that's constantly dark for a week, or a room that's constantly bright for a week?"

"Oh gosh!" Sophia pulled an intimidated face. "Ummm...I think constantly bright for a week? 'Cause then I could see whatever's around me, but if I was in a dark room, then I couldn't see anything! I'd be sooo scared."

"Good answer," James said with a smile. "I'll keep that in mind. Okay, next one. Would you rather...always wear shirts that are two sizes too big, or one size too small?"

"Two sizes too big, right?" She didn't even have to think about that one. "It'd be waaay more comfortable. Too small would be like skintight and just blech! Like when Bella and I switched clothes for a day. Bad idea, guys, okay? Bad idea."

While she was talking, James made a pointed look at Sophia's chest, just imagining how she must look in a shirt that's a size too small for her. Sophia didn't seem to notice the look.

"Okay, good," James said. "Hey, speaking of shirts, that gives me a good idea for your first dare question. Ready?"

"Yeah!" she said, wondering how it could be related to the previous question. She glanced at the camera. "This'll be fun, guys!"

"Okay." His next question was a big leap toward getting what he wanted from her. He felt butterflies in his stomach just thinking about it! "Would you rather...do the rest of this video with no pants on, or no shirt on?"

Sophia's face looked both confused and shocked at the same time. "Ummm, gosh...I wanna do it with both on?"

"No, you have to do one or the other," he said in a subtly firm voice. "Which is it, Sophia?"

Her eyebrows frowned. "Um...pants, I guess. 'Cause then I could just sit real low and no one would even know!"

"Okay, pants it is." And he sat back, crossed his arms, and looked expectantly at her.

The camera recorded dead air between them.

"So...next question?" Sophia asked.

James shook his head. "There's still something you have to do before we move on."

Sophia's smile vanished. "You know, my mom's gonna be back soon...we should wrap this up." She held up the remote control toward the camera.

"Done so soon?" James said, staring at her. "You don't even have a video to post yet. What's your mom gonna think when she comes home and finds you did nothing all day, instead of the video you begged her to let you make?"

"Yeah, you're right..." She did want to prove to her mother that she could actually do a video. Maybe backing out of it wasn't the best idea.

"Come on, Sophia," James urged. "I'll take mine off too, if that'll help you be comfortable with it."

"No, it's okay." She got up off the chair and turned. "I'll be right back!"

"Where are you going?"

"To take my pants off?"

"Do it here," James commanded.

"In front of you?"

"I'll see you with your pants off either way. Why not?"

Sophia took a big, big breath, then nodded. "Okay." She looked at the camera again. "Okay, guys, here I go."

Her fingers touched the button on her jeans and slowly undid it, along with the zipper. She had to bend down to help push her jeans down her legs as far as she could get them. They fell to the floor and she stepped out of them, leaving her skin bare and exposed from her thighs down.

James was pleased to see her legs bore that slightly-tan skintone just like the rest of her body, although her legs were a little more pale. Clearly, Sophia's legs rarely saw the sun. His eyes tracked up and down her naked legs, taking in as much of the gorgeous sight as they could.

A quiet moan vibrated his throat as his eyes got to the hem of her light blue shirt. It was just long enough to cover her hips and most of her groin, but just short enough to give the slightest little tease of her panties. They looked to be his favorite color for a girl's panties, judging by the light pink stretch of fabric nestled right in between Sophia's thighs.

If Sophia had been watching her camera's feed, she might have noticed the bulge growing underneath James's pants. Instead, she just kicked her jeans aside and settled back into her chair, trying to keep her legs off camera and her shirt pulled down over them. Not even Bella typically saw her with no pants on, and now this man (as cute as she thought he was) couldn't keep his eyes off of her.

"There," James said. "That wasn't so hard, was it? Fun dare, right?"

"Yeah," Sophia said with a shrug. "Next question?"

"Okay. Just so you know, every question is going to be a dare question from here on out. Okay?"

Her lips parted. "Every question?"

"It wouldn't be a challenge if it wasn't...you know, a challenge, right?"

Sophia took another breath. "Yeah, I guess so."

"Good girl," James said. "Okay, next dare. Would you rather...take your shirt off while facing the camera, or take it off while facing me?"

"You want my shirt off too?"

"Yup. No way around that, sorry." He wasn't.

"Umm...what do you think I should do, guys? I guess...facing you? 'Cause then..." She trailed off, her cheeks suddenly showing a blush of pink.

"Then what, Sophia?"

She avoided the unblinking gaze of the camera. "Then you'll see but they won't."

"See what?"

"Um...my chest?"

"That's fair," James said. "Now hurry, your mom will be back soon!"

She stood up again and faced him. The camera saw only her brown hair cascading down over her sky blue shirt, and a small triangle of pink peeking out from just under her shirt's hem. James, however, had a front row seat to a show he had been dreaming of for years.

Sophia's hands shook as her fingers wrapped around the hem of her shirt on either side of her hips. She pulled it up so slowly that it felt, to James, like a million years was passing between each second. To her, though, it was more like everything was happening in the blink of an eye. Only a few minutes ago, she had been trying to play an innocent game. Now she was revealing her stomach, her hips, almost her whole body to this man?

Then there came an audible gasp from James as he saw one reason why Sophia had been so embarrassed. As the rising hem of her shirt revealed her gorgeous midriff and her ribcage poking out from underneath her skin, he began to realize that her shirt had been the only thing she was wearing on her torso. She rose her shirt up to her shoulders and up over her head, and the whole world faded away for James as Sophia's naked, braless chest was shown off to him for the first time.

As soon as her arms fell to her sides and dropped the shirt, James's hand shot to his bulge. Finally, after so long, he was allowed to see his angel from the internet without a pesky shirt or any other bit of fabric in the way, and he was simply amazed. Like her legs, her entire torso was more pale than her arms and face but still subtly tan - but he barely noticed any of that, with his eyes as glued to her breasts as they were.

Sophia's breasts were exactly as he'd imagined them. They were the size of baseballs on her chest; perfectly round, perfectly perky, perfectly everything. Even the cute pink bumps of her nipples were perfect in James's eyes. All he wanted to do was reach out and grab them and feel those firm breasts under his palms.

Now that his perfect angel was standing in front of him and the camera, wearing only a pair of innocent pink panties, James could no longer hide his bulge. His hand moved to it and groped himself as he looked over her body.

"Okay, we should be almost done with this video," James said, his eyes moving back up to Sophia's blushing face. "Next dare. Would you rather spend the rest of this video standing up or on your knees?"

"Ummm..." She looked away from him, her pretty blue eyes glancing at the floor. "I...guess on my knees?"

"Why is that?"

"So I can...can kind of hide? Is that okay?" Sophia looked back at James, searching for his approval.

"Well, I don't want you to hide from me. But you made the right choice. Get on your knees."

And Sophia knelt for him, her bare knees reluctant to touch the cold, hard wood on the floor. As Sophia got herself all comfy there, James was busy with the zipper on his pants, working to release his bulge from its captivity. When Sophia glanced back up from the floor to James, her eyes were greeted not with his face but with the sight of his hard manhood, sticking straight up mere inches from her.

Sophia gasped at the sudden, shocking sight of it. "What...what are you..."

"What's wrong? Haven't you seen one before?"

"Yeah, in books! Why?" She could hardly think of any other words to say than that.

"It's for your next dare, silly," he said, as though it should've been obvious to the 15-year-old. "Would you rather...suck my cock? Or lose your virginity to it?"

Sophia's eyebrows furrowed and her glossed lips pouted. "This isn't fun anymore. Can we stop? Please?"

"You haven't finished your video yet, Sophia. You have to play the whole game."

"I...I guess the first one...if I have to."

"Say it."

"I'd rather suck your...you know."

James looked at her without saying a thing.

"Your cock." The word was awkward and rough in Sophia's mouth. Her nearly naked body shifted as she said it, uncomfortable for more than one reason. "I'd rather suck your cock." Which was a lie. She didn't want to do any of it, especially with how gigantic this thing looked to her inexperienced eyes.

"Good girl." He pointed his cock at her, expecting her to get started right then and there, though he knew it would take her a little while to open up to it.

Sophia wasn't at the point of tearing up yet, but it looked like she was almost there. She took a deep breath as she reached up a hand to help her aim it, and leaned her body in. She started with a kiss on his head, trying to feel if it felt any different from any other part of his skin. It didn't, so she snaked her tongue out to give it a lick. It surprised her how soft it felt on her tongue, when she had been expecting something so big and stiff and angry-looking to feel more like a rock or a piece of steel.

Another deep breath, then she parted her lips and wrapped them around his head, eliciting a groan from James that sounded like the biggest load of his life had just been lifted from his shoulders. For Sophia, it was a weird new sensation, having this thing in her mouth; it was warm, like delicious warm food...but soft and squishy like a plush toy...but hard and stiff like a wooden board. For James, it was the start of the single most important and satisfying blowjob of his life.

She was, to put it bluntly, bad at it. He expected that. She couldn't get her mouth quite wide enough and had trouble keeping her teeth from touching his cock as she took more of it in. She couldn't get very much of it in her mouth at a time either, gagging every time his head touched against the very back of her throat and threatened to push further. Every time she did, she had to pull her mouth away, gasp in a heaving, choking breath, and start all over again from scratch. Needless to say, she couldn't get but about an inch and a half of his cock in her mouth at a time.

Still, despite her youthful, inexperienced awkwardness, James loved every second of it. Sophia's glossy lips felt so warm around his shaft. That was nothing compared to the heavenly feeling of her tongue curling against his head. She was bad at sucking his cock, yes, but that didn't change how perfect her mouth felt around him.

He looked down at Sophia - his little angel, with her mouth stuffed full of his cock - and took in the sight. Her eyebrows were still furrowed in a pout. Her cheeks were blushing and flushing in all shades of pink. Her chest heaved as she tried to figure out how to breathe with a cock filling up her mouth. Though it was one of the most uncomfortable experiences of Sophia's entire life, James thought she had never looked more beautiful, not once in any of her videos or Instagram posts.

He placed a hand on her head, her light brown hair so soft under his fingers. The touch made her eyes glance up at him, giving her a reminder of exactly what she was doing and how much older than her this man was. Where she felt humiliation and discomfort she didn't have the words to describe quite yet, he felt nothing but deep satisfaction.

Far too soon, James felt that satisfaction threatening to boil over. He grabbed her hair in his fingers, trying to encourage her to take more of him, even if it made her pretty little throat gag. This would quickly become a fleeting moment and he wanted to get the most out of it that he could. She tried to pull back against his hand and push his body away from her, but none of it worked as James more or less grabbed her head and took control of her blowjob.

Only seconds later - a humiliating lifetime for Sophia, an all-too-quick instant for James - his balls tightened against his body and he gave one final thrust into her mouth, forcing his head just a little further than she could handle. With a series of lewd groans and grunts, James shot straight down her throat, dumping his precious cum down into her stomach. He stayed there in her gagging mouth until he had shot as much as he was going to, and until he was fully satisfied and ready to leave her mouth, before finally and reluctantly pulling out.

James's softening cock left a trail of wetness across her lips and down her chin as it flopped out of her mouth. Sophia coughed and choked the gagging away, trying to recuperate from his invasion of her throat. Though very little of his cum touched her tongue, it was still like a gross aftertaste in her mouth that made her throat feel dry and thirsty. She collapsed into a cross-legged pose as James sat back with a smile on his face.

"Good job, Sophia!" James said. "I think you might've won this game! Have you ever won Would You Rather before?"

"No...we don't have winners..." Her voice was quiet and a little ragged. She was so thirsty.

"Well, you should. And you do now." Though he wanted to stay with her there for hours and hours, he believed that her mom really would be home soon, and so was already stuffing his happy cock back into his pants. "Well, this was fantastic and I think it would make for a video a lot of people will love. It's just a shame I can't let you post it to Youtube."

"Wh-what?" She glanced up at him with a confused look, and he noticed how the gloss on her lips had become sloppy and messed-up.

His pants all zipped up, James stood and reached for the still-filming camera. He turned it off, removed the video card, and waved it at her. "Your video. I can't let you post this on Youtube, can I? I'll get in so much trouble. Well, we both will; I'll get in trouble for getting a blowjob from you and you'll get in trouble with your mom for letting a strange older man into your house. Who knows what I could've done to you?"

"But you were a fan, you seemed so nice."

"That was the idea, Sophia," he replied. "And hey, I am nice. You just have to get to know me."

James reached down to help Sophia stand up, encouraging her toward sitting down in the chair instead. He only did it so he could get one last look at her almost naked body before he left her, his eyes glancing over everything from her bare shoulders to her flat stomach to her cute, perky breasts. Of course, there was one part of her body he still hadn't seen, still covered up as it was by those pink panties...but he wasn't planning on leaving forever.

"Well, I should be going and you should get dressed. Your mom will be back soon, after all." James smiled down at her. "But hey. I had so much fun today that this definitely won't be the last video we make together. I hope you'll be as good a girl next time as you were today. Just remember, I still have this video of you and you...well, you don't."

James turned and headed for the door, leaving his little angel behind him. As he stepped into the hallway, he said one last thing over his shoulder. "Make sure you drink some water, okay? I love you, Sophia!"

She heard the door shut a few minutes later, but didn't really register it. Her eyes were finally tearing up, now that she was alone with her thoughts. That had been the most uncomfortable experience of her entire life and it hadn't even lasted an hour. She couldn't tell anyone about it even if she wanted to, since he had taken the only copy of that video with him. But what was he going to do with it? He could do anything with it. He could post it online himself and then everyone she had ever known could see her doing...that to him - and that was why she didn't want to tell anyone in the first place! It was such a humiliating thing to have to talk about that she didn't want anyone to know about it, ever!

Sophia was so lost in her thoughts that she didn't even get herself dressed until the moment she heard her mom and Bella coming home. Then, in a panic, she rushed to the bathroom with her clothes and got dressed as quick as she could. She had no idea how to explain the lost video card or the fact that she had no video to show for an entire day alone in the house. Today was her little secret and she had to keep it as quiet as she could, no matter how uncomfortable the whole thing had made her.

That night, once she got nestled into her bed and finally pushed away the discomfort enough to sleep, she had a dream about James. It wasn't a bad dream, strangely enough. No, it was a dream of her kissing him the next time he might visit her. She woke up with a deep sense of worried uneasiness...and her stomach full of butterflies.

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