@RazorMane  
Not unless it’s messing with somepony really badly.
 
He has a heck of an ego, though. Comes with being a being as powerful as lawless as himself, I guess. But he’d probably never take much to humiliating things.
 
This is about the closest I’ve ever seen him believably come to diapers:  
>>1114763t (deleted)
 
Getting Pinkie in one just to make a joke/pun. Not forcefully. Just asked her to wear one to help with the shower I guess? And she’s definitely the only pony that would just say yes, hah…

@BlazeHeartUnicorn  
It just doesn’t really fit in with his character but that’s just my opinion.

Fluttershy: What you did at the Gala was very bad! Threating to send one of my best friends to the sock puppet dimension has earned you a spot in diapers!

yes. think about what you did…  
and while you do that, wonder why your neck is wrinkled.

You don’t normally see a lot of Diapered Discord

naughty bad boy!