(Just moving these from PMs)
I was thinking, since it could involve trick or treating with long breaks between going to the potty, Tails could have trouble holding in his bathroom needs.

So, if Vanilla is watching Tails and her daughter while they trick or treat, then she could diaper Tails beforehand or find a way to diaper him when he feels the need to go when they can't get to a toilet on time. Perhaps, additionally there could also be an issue of costume complexity causing the problems (Getting the costume off in time to not have an accident in it.) as well, leading to diapering Tails being a logical and preventative decision of Vanilla's well as outcome.

A second thought I just had was the above, but placed in the Sonic Movie 2 universe with Tom and Maddie. So, a part of costume shopping is to stop by the baby aisle to get a small pack of baby diapers for Tails (Unless they already have a pack at home for long car trips or bedwetting.) to wear while out. This could possibly introduce other cute stuff like Tails falling asleep in a stroller.
I guess he might be curious about them and might want to try wearing them full time, having Tom and Maddie care for him, after that, especially with how he grew up?

Those are some really cute ideas! I'm trying not to include any official characters or anything like that in the Nappy Halloween series.

I might still do a story like this, but I don't think I'll have time to get to it before Halloween. I might do it later.

Ok. Thank you.

OH!

What about a she wolf burglar who breaks into a house on Halloween, knowing that the couple, a pair of loving large tigers, have taken their five year old daughter trick or treating and will be gone, leaving their house vulnerable. However, she doesn't know that they are magical and after breaking in, while starting to ransack the place, she starts feeling different. At first, she gets an urge to suck her thumb, starts crying when she stubs her toe, and even wets and messes herself, suddenly realizing she's wearing a diaper with cute designs on it and a legless onesie, a large pacifier in her mouth. The family have returned early and find the large puppy. The couple decide that they have room in their family for the new addition, and the daughter is excited to have a baby sister. The burglar tries to run/waddle, even calling out for help from the neighbors, but they just all see a toddler, before she is scooped up by her new mommy or daddy, dressed in a cutesey costume, after a diaper change, and then taken trick or treating. At one point her stomach rumbles, so her new mommy starts to nurse her, which she cannot resist until her tummy is full. A week later, and she has more or less settled into her new life, granted having made some escape attempts, all of which failed. She's nervous because she's heard mommy and daddy talk about enrolling her in pre-school all while her big sister lovingly checks her diaper, even able to pick her up and carry her to the changing table in her new nursery.

Now that sounds like a fun idea! That would make a great story.

Yay!

Might have to switch up the ending a bit though as I try to keep these stories focused on Halloween night. We'll have to see.

:-D

Some friends lost a bet with their rivals at school and are forced to diaper up and sneak through a "haunted" forest while the other kids try their best to scare them into having an accident. Turns out the forest is actually haunted.

Ooh, that sounds like a lot of fun. It's also kinda similar to another idea I had so I might have to tweak it a bit. We'll see.

I'm guessing that the other kids end up having accidents without being protected, causing them to be worse off, more obvious, and more uncomfortable than the kids who actually wore diapers and can just easily change them?

interesting twist. Not where I would have gone but that could be interesting.