My friend  AssortedFlavors and I were having trouble deciding on a costume to wear for Halloween this year. I don't know how the subject was changed to maids, but JR at some point told me that he always wanted to dress up like a maid. I encouraged him to be a maid for Halloween. What's a more perfect opportunity to dress up however you want? Surprisingly, he asked me to join in and dress as a maid with him, so he won't feel as nervous about it.
Naturally this made my cheeks burn up. Wh-what's worse is that he wanted me to also be diapered during the holiday! I tried to reason with him that I could just wear regular underwear, but he said we wouldn't match if I chose to do that. Unable to argue with such solid logic, I accepted his request. It wouldn't be so bad; it was just one night.
There was nothing more embarrassing than having to be helped into that outfit and diapered by my friend. How was I supposed to know how to put that stuff on? Also how does he walk in these?! I was blushing a storm for the first few hours of the night, but I eventually calmed down and distracted myself by Trick or Treating for as much candy as possible! Though somehow JR got so much candy, and I hardly got any! I knew he was way cuter than me, but I didn't think I'd suffer like this. I barely got anything! Well....at least I got to have a fun Halloween.

This art was made by  CookieFennecCreations and what a masterpiece it turned out to be.