The App (Patreon)

Here's this month's Community Story! The phrasing of the prompt, "Using the wrong match finding app and realizing a bit late that you’ve met a babysitter not a date," inspired me to try it in a style that I haven't done in quite a while, but hopefully it turned out all right!

"Whoa," you mutter, cheeks warming as you realize you'd spoken out loud.

"See?" your friend, Cassidy, smirks. "I'm telling you, it's the best app I've used."

You nod, doing your best not to squirm, not to show how much you agree. After months of having no luck with dating apps, you'd finally decided to ask Cassidy for advice. You hadn't even been sure if you'd heard the name of it right, since it seemed an odd fit, and there had been a lot of strange questions you'd had to fill out for the profile, and yet, as soon as you'd opened the app, you'd seen... her.

She wasn't even your type, or, at least, not what you'd say your type was. Gawking at her picture, however, seeing the way her ample cleavage strained against the almost too-low cut of her tight dress, you suspect that, deep down, she's everyone's type; the question is whether they're willing to admit it to themselves or not.

That does raise a problem, though, doesn't it? "She'd never choose me," you shake your head, ready to swipe away. You don't want the disappointment of being turned down immediately. That had happened plenty on every other app.

"Oh, come on," Cassidy teased. "Don't be a baby! You'll never know until you try!"

You shrug. "I guess," you say, shifting in your seat. You know you want to, that if, by some chance, she did say yes, you'd be thrilled... Then you recall one of the questions from the profile that had really struck you as weird, maybe a bit too transparent. 'How much are you willing to pay?' it had said, presumably to give an idea of what sort of date any potential matches could expect to be taken on. At this point, you'd prefer to let the other person choose to make sure they went somewhere they would like, since you'd had bad luck in the past when you made the decision, but the field had only allowed numbers.

The one you'd put had been fairly modest, though now you go back, jack it up. You don't want to assume this woman would be more attracted to someone who could take her out some place extra fancy, however... It can't hurt, right? You go back to her profile, search for the button that will alert her that someone matched with her. The closest you can find is one that reads, 'Check Availability.'

It's an unusual way to put it, definitely; was this whole app made in another country, translated awkwardly into English? You would be worried that it was some sort of scam if Cassidy hadn't vouched for it from firsthand experience.

"Why not?" you say, hitting the button. What's the worst that can happen?

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

You don't normally pay that much attention to clothes, despite some of your friends telling you that you should, yet now you've spent more time in front of your closet than you had in quite some time, thumbing through outfits, rejecting each one as not quite right, then going back to it after a couple more had been deemed insufficient, wondering if you'd been too harsh.

You had, finally, settled on something, though as you look at yourself in the mirror, you can't help feeling like it isn't good enough, that you should try again. It still blows your mind a little that it had worked, that she had accepted your match, and almost instantly at that, just after you'd finished hanging out with Cassidy.

That had led to another form to fill out in the app, and you'd wished your friend was still there so you could confirm what, exactly, it was. After a few moments, you'd decided it must be to determine when you were available to go on dates; if you were wrong, it could be something you could laugh about on the date, you'd supposed. You didn't want to bother Cassidy with it, and it really felt like bad form to start your new relationship by asking your date about it, so you'd winged it.

You wonder if you should have given yourself a bit more time after work to get ready, like you wonder if you should have been more conservative about the end time. You'd had to pick something, and you've heard stories of dates that had gone long into the night, just talking... That sounded nice, and romantic, and you didn't want to limit the chance at having that for yourself, but thinking about it now, a part of you hopes that doesn't mean you're going to be expected to stay up until the next morning. You'd given yourself enough time to prepare for work, though sleep would be nice to have, too.

That definitely wasn't the oddest question, however; that crown belonged to the bizarre, 'Nighttime protection?' drop-down box, with no clarification, only a 'Yes' or 'No' to choose from. That one you'd really almost messaged Cassidy about, but you didn't want to seem dumb for not getting it. Was it a covert way of asking about condoms? It was the best - and only - possibility you could think of, so you'd picked 'Yes.'

You flinch at the sound of your doorbell, taking one last glance at the mirror. It's too late to change your mind now, you think. This is just going to have to do... All you can do now is hope you don't screw this up somehow. With a deep breath, you step out of your bedroom and head for your front door, a sudden shyness washing over you as you reach it, along with a twinge of fear. What if this is a catfishing scenario? What if you open the door, and someone completely different is on the other side?

The doorbell rings again, making you jump. There's only one way to find out, you tell yourself. And all you have to do is reach out, turn the doorknob, and see...

Your eyes widen as you slowly open the door, your heart racing as you reveal more and more of the woman standing on the other side, waiting patiently, trying your hardest not to stare. It is, indeed, her, and she looks even hotter in real life, somehow, than she had in her pictures. The difference in your height hadn't seemed so dramatic, seeing it in numbers, but she towers over you, even in the tennis shoes she's wearing, making you grateful she'd forgone heels. She's in a small, white dress, too, the top of it held in place with a bit of knotted fabric that seems ready to come undone at any moment, and, as much as you do your best to keep your eyes away, they are immediately drawn to her breasts in it.

"H-Hi," you squeak, feeling very tiny, very inadequate, in comparison to her.

"Hello, there!" she smiles, bending forward, emphasizing her cleavage that much more. "Don't you look cute?"

You're not sure if she meant that to be an insult or not. It doesn't feel that way, and yet the tone she'd used sounds like she's making fun of you, talking to you like she might to a little kid. Considering that was how you felt already, standing next to her, it bruises your ego a bit. "I-I was going to go change," you lie, shuffling backwards.

"Oh, no, there's no need for that!" she shakes her head. "Not yet, sweetie!" She doesn't wait for an invitation, using the bit of space you'd just given her to step inside. "Isn't this lovely?"

"Th-Thanks," you say, trying to shake it off, to regain some dignity.

Her chuckle in response leeches that back away. "So, is it just us?" she asks.

You frown. What does she mean? Is she asking if you have a roommate? "Y-Yeah," you reply uncertainly.

"All right!" she nods. "Have you eaten?"

"Huh?" You're really confused now. "N-No, I thought..."

"Now, now," she coos, patting you on the head. "No need to get fussy. We'll get that taken care of in no time!"

Without a word, she brushes past you, looking around and making a bee-line for the kitchen. You scurry after her, baffled, and even more-so once she starts opening up the cabinets, pulling out pots and pans. "Wait," you tell her. "I-I thought we were going out..."

She laughs again, the sound once more making you feel so very tiny, so silly. "I think you're a little mixed up, cutie. Do you think you could set the table for me?"

"I-I could," you say. "But..."

"Then would you?" she asks. "That would be such a big help!"

You stand there for a moment, wanting to say something as you watch your fantasies of going out to a fancy dinner dissolve as she opens up a box of macaroni and cheese and start to prepare it. This might be better, in a way, you try to convince yourself, though you know you have better food than that... And you know you should do more than set the table in your own kitchen. "I can help!" you offer.

"Setting the table is going to be such a big help!" she repeats condescendingly. "I couldn't ask for anything more!"

She could have, you think as she comes out and fills the plates with mac and cheese, hot dogs, and peas, bending over one of them and cutting up the hot dog into small pieces as you catch yourself gawking at her again, barely shaking yourself out of it in time for her to pull the chair out and declare, "There you go!"

"Huh?" you furrow your brow. "Isn't that...?" You'd assumed that was her seat, even if you weren't sure why she wasn't sitting to get her food ready.

"No arguing," she scolds. "We don't want to be at this all night! Sit down and eat!"

Her voice is so stern, you find yourself starting to obey almost without realizing it, hurrying over to the chair. Only when you're sitting do you notice she'd taken the knife with her, but there's no point in complaining when your hot dog is already sliced up and you don't need it for anything else. It is, you have to admit, tasty, somehow better than you making it on your own would have been.

"Good job cleaning your plate," she praises you when you're finished, getting up and taking it away. "Now, I was hoping we'd have time for a game or two, but we're already running late."

"We are?" What could you be running late for, now that you've eaten your supper here?

"Oh, don't play coy with me," she teases. "Why don't you show me to your bedroom?"

You squirm, palms beginning to sweat. "A-Already?" you gulp.

"Come on," she shakes her head. "You know it's far past time! I just wanted to make sure you'd had your supper! Now, up you go!" She helps you out of your chair, pushes you gently away from the table. You can't deny that you're excited at the prospect, and at how eager she seems to be, but it's all moving so fast...

She looks around your room when you arrive, as you hurry to pick up discarded alternate outfits and hang them back up in the closet. "Neater than I expected," she says, despite that, and, before you can say thanks, or decide if you should be offended she'd assumed your room was messy, she opens up the top drawer of your dresser without a moment's hesitation.

"Hey!" you protest.

"Where's your protection, sweetie?" she asks, rifling through your underwear, your face glowing brighter and brighter red as you watch her hands brushing over them.

"O-Oh," you blink, recalling that question. "I-I..."

"Never mind," she shakes her head. "I'm always prepared!"

Without another word, she steps out of the room, back down the hall. You follow, stomach dropping as she goes back out the front door, wondering if she's going to return... And then, when she does, almost wishing she hadn't. You whimper, hardly able to believe it; this has to be a joke, right?!

"Wh-What...?!" you stammer, shaking your head, finally having something other than her breasts to stare at, to fixate on.

"They might not be your usual brand," she tells you, "but don't try to pretend you don't know what they are, silly. I know you need them." She carries them into the living room, sitting down, the full, bulging package of them beside her in the chair. "I promise, these are going to do the trick, okay? So, unless you can tell me where your Mommy and Daddy put your nighttime diapers, we're going to have to use these."

All you can say, still, is another, even higher pitched, "Wh-What?!" What does she mean diapers?! Mommy and Daddy?! Slowly, it all begins to fall into place, all the weird questions on the profile, the unusual name of the app itself, the way she's been behaving... You don't have a date tonight after all, you realize, to your horror. You have a babysitter. "N-No, there's been a mistake!"

"No, I don't think so," she smirks. "Your parents sent me your picture, sweetie, and they told me you need some protection at night... And that you should be in bed already."

"No, I shouldn't!" you protest, stomping your foot. "The sun is barely setting! A-And I definitely don't need..!" You can't bring yourself to say the word, to accept what is going on. Diapers?! You're an adult! You don't wear diapers!

As if she's reading your mind, she kneels down on the floor, ripping open the package. Maybe it's your imagination, but you feel like the scent of baby powder instantly permeates your living room while you stand there, tears of humiliation welling up in your eyes. This can't be happening! She unfolds the diaper, laying it out, giving it a pat, your head spinning as you hear the gentle crinkling of plastic. "We're had so much fun, little one," she urges. "Don't make me ruin it with a spanking!"

You can tell she isn't joking, that she'd be more than willing to do it, to take you over her knee. You know you should probably do something, should probably resist, make her see that you're a grown-up... But you can feel yourself start to undress, too scared to cross her, even if it means accepting...

You let out a tiny squeak as you sit down on the waiting diaper, the padding so much softer and cozier under your backside than you could have dreamed. She beams at you, so proud, leaning forward over you. "That's a good sweetie," she says, pulling the front of the diaper up, between your legs, taping it snugly into place, sealing you into your infantile undergarments before you can form another coherent thought, much less word.

It's so thick and bulky between your legs, you almost feel like you need her hand as she leads you, waddling, back to your bedroom. Luckily, she'd taken yours when she helped you stand, letting go only after sitting you down on your bed, going to grab your pajamas from your dresser. The shorts barely fit over the diaper, and you feel a spark of hope that, perhaps, that will help her see that you don't wear diapers after all.

If she notices the shorts don't quite go all the way, that they leave the plastic waistband of your diaper peeking out, she doesn't say anything, doesn't see the significance, simply smiles and declares the whole ensemble, and you in it, "Adorable." Considering the way you'd thought this night was going to end up, that's not the word you'd hoped she'd used to describe you, but a tentative glance into your mirror confirms that she's right. Especially next to her, that's the most accurate description of you, in your PJs and diaper, ready to be tucked into bed while it's still light outside.

But not yet, apparently, as she sits down at the edge of your bed first, grabbing you by the hands, pulling you to her lap. You sit, diaper crackling beneath you, staring up at her. "Now," she strokes your hair, "since you were such a good little one while I got your diaper on you, I think you deserve a treat before bed. What do you think?"

You don't know what to say, what she could mean; it doesn't matter, as she reaches up, starts to untie the front of her dress. You blush as you hear an involuntary gasp escape your mouth, as your diaper begins to grow warm. "I've seen you staring at them all night," she tells you, wrapping her arms around you, pushing you in, closer and closer to her exposed chest. "Go on... Some nice, fresh milk always helps babies like you get a good night's sleep..."

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

"Wake up, sleepyhead!"

You blink, squirm, yawn, sure all that had to have been a dream, one that you aren't sure if you should classify as a nightmare or not... But there definitely is a weird bulk between your legs, and a clammy squishiness to it... And as soon as you open your eyes, you're greeted by the sight of your babysitter, wearing a silky nightie and robe, neither of which does much to hide her chest, your face burning immediately, head swimming as you're reminded that you had, indeed, been breastfed by her mere hours ago, had greedily slurped away, filling your tummy with warm, sweet milk, the closest thing to 'action' that you were going to get on this 'date.'

The results of that are in your diaper now, you think, blushing even harder. You'd woken up in the middle of the night, tossed and turned for a while, then finally worked up the courage to get out of bed, to toddle your way towards the bathroom, only for her to appear out of the guestroom, dressed in the same nightie and robe. "What are you doing up?" she'd asked. "Come on, sweetie, back to bed."

"N-No," you'd whined, shaking your head. "I-I need..."

She'd chuckled. "Uh-huh, I'm sure... I've heard it all, little one. They always need something in the middle of the night... Well, I'm the grown-up here, and I know that all you need is to go back to bed."

She'd tucked you back in, ignoring your every protest. You'd waited as long as you could, until your bladder was nearly bursting, before trying again. This time, she was right outside your door, making you wonder how long it had actually been, assume the answer was 'not very.' This tucking in came with a threat.

"I don't want to have to do it," she'd said, "but I need you to stay in bed, so if I catch you up one more time, you're getting that spanking after all."

You hadn't dared risk that, not least of all because, by then, it was too late anyway. Already, your bladder had given it, started to trickle its contents into your waiting padding, rendering you mute as you laid there, staring up at your babysitter, mortified at what you were doing, at the possibility that she would find out you were in the middle of peeing your pants under her nose... Or that, with all her experience, she already knew.

It had been difficult to fall back asleep after that, soggy diaper squishing around your bottom. That must be why you'd slept so late, despite the early bedtime, why she'd had to wake you up, pull you back to your humiliating reality. "Did you have a good night?" she asks, whisking aside your covers. You wriggle, pressing your legs together, trying to find a way to hide what you'd done from her, but her hand goes straight for the bulk of your diaper and gives it a squeeze.

"Wow," she giggles. "You really drenched it, didn't you?"

You can't bring yourself to answer as she slides your PJ shorts down, exposing your diaper, not until she untapes it, then, to your surprise, grabs a fresh one to slide under you. "N-No!" you pout.

"Yes!" she counters, pulling the old one out, holding it up, showing it off to you. "Just look at how wet and heavy you made this one, little one! I can't trust anyone who did this to their nighttime diapers to keep their pants dry without a bit of help!"

In no time, she has you cleaned up and taped into your new diaper, then changed into a pair of shorts and a t-shirt that didn't fare any better against the padding than your PJs had. She leads you out to the dining room for breakfast, watching the clock as you eat your cereal, waiting for you to finish before saying, "I was hoping your Mommy or Daddy would be back by now, but this was all the longer they hired me for. I don't suppose they left my fee with you, did they?"

You stare up at her, realizing that, of course, as a babysitter, she expected to get paid for all this, for everything she'd done to you. You could tell her about the mistake, but now... You blush, shaking your head. No, it's better to let it go, try to forget about all this. "Y-Yeah, they did," you say, hopping out of your chair, waddling to grab some cash, the same amount you'd told the app you were willing to pay, returning to her to hand it over.

"You sure you'll be al right here on your own?" she frowns as she takes it. "I could wait for your Mommy or Daddy to get here, or help you get onto the bus, or..."

"N-No!" you shake your head. "I-I'm fine, I promise! Th-Thank you!"

~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~

You thought that was the end of it. You deleted the app, went back and found the one Cassidy had actually meant, just one letter off from the one you'd found. It worked as well as promised, getting you a date that night, one that you were certain would wash away the memory of yesterday.

The doorbell rings, and you rush to answer it, opening it up... And finding the babysitter standing there, arms full of diapers. You gasp, whimpering as you feel an instinctive dribble of pee escape into your pants. "Wh-What are you doing here?!" you squeal.

"Don't be silly," she catches the door as you try to close it, pushing it open, stepping in, towering above you. "I'm your babysitter, little one! And tonight, I'm going to get you into bed on time! I could tell you didn't like the diapers from yesterday, so I brought you all these to choose from! I'm sure one of those will be..."

"No!" you whine, stomping your foot. "No, I don't need diapers! I'm not a baby! Leave me alone!"

That doesn't stop her from escorting you to the living room, warm tears of frustration at the corners of your eyes as she kneels down, starts to undress you, pulling away the carefully considered outfit you'd chosen for your date.

"Which do you want to try?" she asks, holding the diapers up. "We can..."

The doorbells rings again, and she turns her head. "Is that your Mommy or Daddy? No, why would they be ringing the doorbell."

"No!" you protest as she gets up to go answer, leaving you lying there, half naked, returning after a moment with your date.

"See?" the babysitter says. "Much too little to be on any silly dating app..."

Your date snickers, looking down at you as you whimper, blush. "Well, the picture does match, but... I bet this little cutie was just playing with their Mommy's phone and didn't realize what they were doing."

"Definitely," the babysitter agrees. "I'm sorry about the confusion, and I hate that you came all the way out here..." She looks your date up and down, smiles. "I mean... I don't know if you're interested, but I am single."

Your stomach churns as you see your date size up the sitter, obviously able to tell what a jackpot they'd hit. "Don't you have to...?" your date glances down at you.

"Here," your babysitter kneels back down in front of you. "Why don't you help me get them into their nighttime diaper, and then we'll get them fed their supper, and tucked into bed, and we'll have the whole place to ourselves... The bed in the spare room is nice and big..."

You shake your head in frustration at the idea of this woman doing this, at her treating you like a baby, stealing your date, using your own spare room to woo your date... But what can you do about it now? The answer, very clearly, is 'Nothing,' as your date points to one of the diapers in your sitter's hands and says, "I bet they'd look cute in that," taking away even your chance to choose for yourself.

"I think you're right," the sitter agrees. "All right, sweetie, legs up! It's diaper time!"