Why hasn’t there been a fanfic made of this yet?

@Gomenasai  
Headcanon accepted. That’s a lovely tale :)

@Gomenasai  
I can dig it.

@Gomenasai  
That’s a really nice back story!

So adorable!

@Gomenasai  
Y’know, that’s oddly quite touching. Kinda like a childhood imaginary friend.

@Beau Skunky  
A dream. RD asked Rarity for a plush of WB, based on the description she gave her.
 
At the time I liked to think of WB as manifestation of RD’s subconscious attempt to fill the role of mother figure in her life with an imaginary character during her childhood, she would only have visions of WB in her dreams. She doesn’t dream of her anymore, but she wanted to have a plush as a reminder.  
Additionally, the fact that Scootaloo favors a wheeled form of transportation further increases RD’s attachment to the filly by subconsciously triggering associations with her past dream friend.
 
This isn’t canon or anything, I just thought it would be an interesting spin on WB’s origin. But that’s assuming RD really grew up without a mother, which is probably not true.

Awww. Weird, but awww.

So this whole time Wheely Bopper was just a toy?

And then Wheely suddenly appears at one of her birthday parties and it turns out it wasn’t a dream after all and she really did have nightly adventures with a dimension-travelling wheeled pony as a filly.

@Background Pony
 
What do you plan to do for the next image?
 
PLEASE DRAW HER CONNECTED TO A BICYCLE PUMP

@Masem  
Pretty much exactly what I had in mind with the substitute for real mother, seeing how she didn’t appear with Rainbow’s dad in the flashback.
 
It goes even farther than that when RD takes notice of Scootaloo riding scooter all the time, thus subconsciously starting to feel more and more attached to her due to the whole “pony on wheels” parallels. Scootaloo is the new incarnation of Wheelie that RD needs in her life.
 
-∀

This idea works so well if you add:  

That may be the single cutest thing in the history of the ponyverse. And that is saying something.

i can’t decide which is more cute, the wheeled pony or filly dashie. seriously you can’t get cuter than that!

Awwww, that’s soo adorable

I can dig it.

@Zennistrad  
Sure, let’s do that. :D

@Keith Mowz
 
Pinkie’s imaginary friend is Surprise.

And now the rest of the Mane Six need an imaginary friend, and for Wheely Bopper, Smarty Pants and the other four to go on an adventure together.

So she’s basically the “Smarty Pants” to RD?
 
I like that canon.
 
And I also like the idea of Rainbow making a “children’s series” of books detailing Wheely’s adventures on the side of being a Wonderbolt sorta as tribute to her love of Daring Do.

@Background Pony  
HNNNNNNGGGGGGGGG

@Background Pony
 
How cute.
 
And it works.

@bradzz  
Alright, added it in the description. Tried to make it shorter but it’s still sort of long, sorry.