Date Day by ImoutoCommissions

Chapter 1

When Lucy wakes up, it is in the sort of situation she is finding 
herself waking up in more and more often lately, a situation that she 
couldn't be happier about. Today, the pajamas she finds herself in are, 
as usual, animal themed and full body, and James has completed the look 
for her with the fake ears and tail, and gloves to look like paws. The 
animal of choice from the night before is a cute little bear, something 
that he could not get enough of when she first donned the outfit.

She lets her mind wander, remembering the first morning she woke up with 
James, her reindeer pajamas absolutely soaked after her first bedwetting 
incident in years. But, despite failing her first challenge with her 
boyfriend, it is not a bad memory, and as she remembers his punishments 
for all her failures, and his rewards for her successes, she can feel 
herself twitching in excitement. Even right now, her bladder is achingly 
full, but she managed to make it through the night without wetting.

Of course, thinking about the past incidents and their aftermaths turns 
her on, but it also reminds her of the pressure in her abdomen and she 
knows that, though she didn't wet overnight, she is nearly at her limit. 
Still, she doesn't want to wake James up, and she knows that there is no 
way to get out of bed without doing that, and so, she decides to try to 
fall back asleep, snuggling up against his chest.

However, now that she is awake and aware of her need, and now that she 
has inadvertently turned herself on, remaining still is a lot more 
difficult than it was before, and she finds herself squirming both in 
her desperation as well as her arousal. Try as she might, she can't get 
herself to fully stop, and so, it isn't long before James is stirred 
awake by all of her movement.

"Good morning, my little teddy bear," he says, once he is fully 
coherent.

Lucy blushes, saying, "Good morning, big bwother," talking in a more 
childlike manner, just the way he likes. "Did you thleep good?" she 
lisps.

"I always do when I have you here," he replies, before rolling her onto 
her back. He reaches between her legs to check for any signs of an 
accident, and when she moans from the touch, he begins rubbing her over 
her pajamas. She squirms and moans, then squeaks in surprise as he 
reaches up to feel her bladder bulge. James grins at the way she squirms 
from both how badly she needs to pee and from how easily he can turn her 
on like this.

But she knows that he's going to push her past her limit like this, so 
she opens her mouth to tell him this, to tell him to cut it out. Of 
course, he will hear none of that, silencing her with a kiss and, while 
she is distracted by this, reaching to the bedside table to grab a small 
remote. He uses this remote to activate the vibrator function of the 
buttplug being used to anchor her little bear tail in place.

Finally, he breaks the kiss, and she protests, "But I'm gonna be a wet 
wittle teddy if you don't let me go potty thoon!"

She looks at him with such wide, cute eyes that he can't hope to resist 
her and, deciding to show her some mercy, he helps her up, and follows 
her into the bathroom. Lucy squirms in place, begging him, "Pwease, 
unzip me, hurry before I have an accident!"

Just to draw this out a little bit longer, he takes his time in pulling 
down her zipper, doing so slowly and enjoying every last bit of 
squirming as she impatiently waits for him to finish. Finally, he 
reaches the end of the zipper and pulls her outfit down to her ankles, 
and Lucy scrambles to sit on the toilet, though she just barely makes it 
over the bowl before she loses control, just seconds away from making a 
mess of herself and the floor.

She sighs in relief, the force of her stream intense until it slowly 
trickles to a stop, her overfull bladder still cramping a bit even after 
she has emptied it. But before she can grab the toilet paper to wipe 
herself, James has already made his move, tossing her legs over his 
shoulders and leaning in, murmuring, "Did you think I forgot about your 
other need this morning?"

With that, he buries his tongue inside of her, and she loses herself in 
her pleasure, moaning in surprise and delight as her big brother gets to 
work. She leans back, relaxing and letting him take control, tracing his 
tongue inside of her until she tightens so much that he can tell she's 
right on the edge of her orgasm. When he notices that, he pulls back, 
only to push his erection inside of her, filling her completely and 
sending her over the edge with this motion.

Not stopping at this, he begins pounding into her, prolonging her 
climax, and she moans and cries out for him, so lost in this that she 
doesn't even notice that he picks her up. In fact, she doesn't notice 
anything until they're already in the shower, when the cold water comes 
on and surprises her.

Lucy scowls at him, shivering, but it does not take long for the water 
to warm up, nor does it take long for him to resume thrusting into her. 
She cannot hope to speak at this point, moaning and mewling as he makes 
love to her, keeping this up until they reach a shared climax, James 
spilling into her with a low moan and Lucy clinging to him with one 
final cry of pleasure.

After taking a moment to recover, he begins massaging her with body 
wash, helping her shower as well as washing himself. It takes a bit 
longer this way than if they were both to do so separately, but he 
enjoys taking care of her in every aspect that he can. Once the two of 
them are completely washed up and dried off, they begin dressing for 
their day out together.

Lucy puts on a wine red sweater dress that comes down to her knees, one 
that has small hearts in purples and pinks all over it, wearing white 
leggings beneath it, and cinching it at the waist with a heart buckled 
belt. In their time together, she has come to love playing the role of 
his spoiled little sister, and once she is done getting dressed, she 
does a little twirl for him, asking, "How do I look?"

James grabs a hold of her, pulling her right off her feet so that he can 
spin her around, declaring, "You look absolutely adorable, my sweet 
little sister!" She giggles at his antics, until he sets her down, 
kissing her on the forehead and saying, "Alright, I hope you're ready to 
go to the mall!"

Chapter 2

James and Lucy arrive at the mall not long later, beginning their fun 
day of playing as an older brother spoiling his little sister. To most, 
they might look like a typical couple, but to others, they really might 
look like a pair of siblings, especially due to Lucy's small size. But 
they couldn't care less how they appeared to others, having all of their 
fun together.

They eat together and she has a couple of drinks, which means that it 
isn't too long into their date that she starts to feel her bladder start 
to fill, and when she knows that it's to a point that she needs to do 
something about it, she whispers in her big brother's ear, "I need to go 
potty."

"You do?" he asks. "How so?"

Blushing, she leans into whisper again, specifying, "I need to go 
tinkle."

"You need to hold it for a little longer," he replies, which isn't much 
of a surprise to her, knowing him as she does. "Do you think you can do 
that for your big brother?"

Lucy nods, trying to ignore the protest from her bladder, wanting to 
hold for as long as she can to impress him. Or, at least, that's what 
she wants to do, but as her small bladder continues to fill, she knows 
that she doesn't actually have very long before she meets her limit.

Still, she tries to fight it for as long as she can, ignoring the 
throbbing building up, but when she finds that it is becoming a 
challenge to walk normally, and she begins showing more outward signs of 
desperation, she cannot continue keep up the challenge any longer. She 
tugs on his sleeve to get his attention and begs, "Can I please go potty 
now, big bwother? Please?"

"Are you sure you can't hold it anymore?" he asks, the look in his eyes 
unmistakable as he watches her squirm in place, struggling against her 
need.

"Please," she repeats. "I'll make peepee in my panties if you don't let 
me go potty soon!"

He nods in understanding, taking her hand to lead her to one of the 
family styled restrooms, something that they have become frequent 
visitors of in their time as a couple. Once they are locked in, with 
Lucy dancing while she moves to fight her need, she goes in front of the 
toilet, giving a sigh as she undoes the belt around her waist. That at 
least undoes some of the pressure, and she lifts her dress so that James 
can pull down her leggings and her panties, exposing her cleanly 
hairless girlhood.

Rather than letting her sit, James reaches up to massage her small 
buttocks, pressing his tongue between her tightly pressed together 
thighs, finding her pussy with his tongue.

She begins trembling now from arousal, and asks, "Are you trying to 
become a literal potty mouth?"

He turns her around, freeing his cock so that he can tease her with it, 
slipping it between her thighs and rubbing against her slit. James 
continues riling her up until she can't take it anymore, begging him, 
"Please stick it in me!" Not needing any further convincing, he bends 
her over the toilet, spreading her thighs and pushing himself inside of 
her.

Though she asked for this, as she stares down into the water beneath 
her, she remembers their reasoning for being here and how close she was 
to relief. Now, she finds herself begging him, "Please, please hurry up 
and empty your balls so I can empty my bladder!"

James shifts their position, lifting her by her knees and stretching her 
panties and leggings as he reaches up under her dress to toy with her 
nipples. He shows her no mercy when it comes to his thrusts, aiming each 
one towards her swollen bladder and paying no mind to how she protests, 
begging for the mercy he won't give her. He has her carefully angled, 
after all, and as each thrust brings her closer to orgasm, he brings 
himself there as well.

As always, feeling him come inside of her, being filled with his hot 
seed, is too much for her to handle, and her climax spells her doom in 
terms of holding it. As she gives into her pleasure, her bladder gives 
in as well, and she is lucky that James is holding her so perfectly over 
the toilet, or else the force of her stream would have made quite the 
mess in the process.

Though this was definitely his plan all along, once she has recovered 
from her orgasm, he gives her a swat to the behind, sitting her on her 
shaky legs. "You peed without permission, so now your potty privileges 
are revoked for the rest of the day, young lady. Not to mention, you're 
in for quite the punishment when we get home."

"But I-" she starts.

"No buts," he replies, pulling up her panties and leggings, before 
fastening her belt even tighter than it was before.

~X~

They continue their date before deciding to end it with a trip to the 
movies, where James buys her the largest size soda they have. As he 
hands it to her, he jokes, "It looks like it's even bigger than you 
are!" In a more serious tone, he adds, "You'd better finish that before 
the movie is over."

Lucy nods, though she is a bit daunted, and when they are in the 
theater, she decides to get a little revenge by sitting on his lap for 
the movie. She is able to rub her butt against him throughout, teasing 
him quite a bit, but she also gives him yet another advantage over her, 
because he is able to rub his hands along her stomach, checking again 
and again for the steadily growing swell of her bladder. And, whenever 
she slows in drinking her drink, he can lean in to whisper reminders in 
her ear.

Needless to say, since she hasn't been to the bathroom since their 
little incident earlier, it does not take long for Lucy to feel the 
effects of the large soda. Soon, her squirming is not just to tease him, 
but simply because it is a struggle for her to sit still, and by the 
time the movie is over, she is absolutely bursting.

James leads her through the lobby, and as they pass the bathrooms, she 
stops, begging him, "Let me have a potty break before we go home!" To 
emphasize her point, she grabs herself, squirming around, and paying no 
mind to who might see her very over the top potty dance.

James is unsympathetic to her little display, and instead grabs her 
tightly by the wrist, dragging her out like a disobedient child, and he 
scolds her for behaving like that in public. "Don't forget, you've got 
to be punished when we get home, and for that, you've just increased 
it."

Lucy isn't sure what is more intense; her dread, or her excitement.

Chapter 3

When they get home, James wastes no time in preparing for his planned 
punishment, and quickly strips Lucy out of her dress and leggings, 
leaving her completely exposed before him. He rubs her now bulging 
bladder, saying, "You look so cute with this out and on display."

Producing silky rope, he ties her hands behind her back and lays her 
down on an absorbent pad he's placed on the living room floor, before 
tying her knees up around her elbows, leaving her squirming and 
vulnerable as he goes to prepare yet another feature for tonight.

James sets up a camera, with a live feed displayed on the living room 
television, which gives Lucy a greatly magnified view of herself, 
squirming and bound on the floor. In the back of her mind, she imagines 
James uploading what he records to the internet, and this thought is 
more arousing to her than she ever would have expected it to be.

"Alright, dear," he says, "why don't you introduce yourself and tell us 
why you're all tied up right now?"

"I-I'm Lucy," she says, pretending to struggle to pronounce the L in her 
name. "I had a accident today at the mall, so my big bwother is gonna 
punish me." She pauses for a moment, before deciding to add, "Actually, 
my big bwother has had to punish me a lot lately, because I keep making 
pee pee in my panties."

James remains mostly out of the frame, leaving Lucy to be the star of 
the show while he puts his hands on her flat chest, squeezing her small 
breasts. "Do you like that?" he asks.

"Yes," she admits, "I'm a naughty girl who likes having my tiny titties 
played with."

"And do you think you should be punished for that as well?"

"I think my big bwother should pinch and twist my nipples," she replies, 
and squeaks when James begins doing just that, taking both niples 
harshly between his fingers and applying pressure before twisting them. 
She squirms with the mixture of pleasure and pain, just barely holding 
onto the contents of her straining bladder as she does.

Even when he's done doing that, James applies nipple clamps so that the 
pressure is not lessened while he moves on to do other things. His hands 
drift down to her clit, where he at first gives her a few gentle strokes 
before he begins similar treatment to what he gave her nipples. As he 
tortures her clit, and then her pussy, she says, "I have a real naughty 
twatty that loves letting out peepee in my panties, so you should punish 
it real hard!"

"I know just the thing for that," James replies, and holds a speculum in 
front of her face. "Do you think I should use this on you?"

"Pry me open!" she replies eagerly. And so, he does, slowly pushing her 
open, and at first, it is like nothing to her, after some of their 
rougher love making sessions, but then, he begins to go farther.

Lucy starts to sweat as he stretches her beyond what she is used to, and 
she winces, the strain in her voice clear as she says, "This is bigger 
than big bwother's cock is. You're stretching me real big, aren't you? 
Everyone watching can see my womb now, right?" She isn't sure if she's 
talking for the benefit of the show she's putting on, or if she's 
talking to keep herself grounded, and block out some of the pain.

Finally, he seems satisfied with how he's pried her open, he leaves the 
speculum in place and moves on. Now, he runs a hand along her stomach, 
stroking her swollen bladder and saying, "How should I punish this?"

Lucy replies, "You should spank it! Spank me there, instead of my 
butt...or you could spank both!"'

He gives a smack to her stomach with one hand, and her rear with the 
other, before asking, "Is that hard enough for you?" When she admits 
that it isn't, he says, "Then I have just the thing for that."

It only takes him a moment to locate the ping pong paddle that they've 
used for this a few times in the past, and Lucy begs, "Please, paddle my 
piddle pot and pretty posterior!" For a moment, she lets her little girl 
facade slip, perfectly pronouncing that little tongue twister.

"That's what you want? Alright, then, little sister!" With that, he 
begins paddling her furiously, alternating between her buttocks and her 
stomach, and she cries out from pain and then pleasure, back and forth 
as she struggles to hold back the flood that each smack to her stomach 
threatens to send spilling over. Just when she thinks that she can't 
take anymore, he finally slows to a stop, leaving her skin reddened.

"Has my naughty little sister had enough?" he asks.

"Big bwother should punish me with his big, beautiful cock," she 
replies, and he agrees with that, changing her position, so that the 
television displays her upside down, pressing her ankles to the pad to 
either side of her head. But when he presses his tip against her, it is 
not to her pussy, but rather, to her other entrance.

"Big bwother has never used that hole before!" she says, somewhat 
panicked. "You're way too big!"

"You should have thought about that before you misbehaved, little lady," 
he replies. "Now you have to take your punishment like a big girl." With 
that, he pushes himself inside of her, claiming her anal virginity, and 
ignoring the way she winces and squeals at the sudden pain.

Lucy grits her teeth, and it takes all that she has not to lose control 
of her bladder in the process. James is not gentle with her, taking no 
time to ease her into it and instead fucking her roughly, but, 
fortunately for her, she soon finds that she enjoys it, the pain not 
able to compare to the pleasure it brings her. Soon enough, her squeals 
of pain have turned into delighted moans.

And then, when he feels himself getting close, he pulls out in time to 
fill her pussy, still pried open, with his seed. For a moment, he rests 
over her, panting, before he relaxes further, emptying his own bladder. 
This is absolutely torturous for her, but still she holds on, fighting 
her needs to the very end.

As their show comes to a close. James says, "You did a very good job, 
not wetting during your punishment. I'm very proud of you, little 
sister."

"Can I go potty now?" she asks pleadingly.

"Absolutely not," he replies so gently that it's almost hard to believe 
he's being cruel. Instead, he helps her up, after removing the speculum, 
and helps her get dressed in extra thick and absorbent panties, a pair 
of rubber pants, and on top of that, a brand new set of pajamas, this 
time resembling a mouse.

Once she's all dressed, still squirming with her need, he picks her up 
to carry her to bed. "You'll get a nice, big reward if you're dry in the 
morning," he promises her, but she isn't quite sure how she's going to 
pull that one off.