I bet Yuri's extra annoyed because people will think he's a girl more often that normal now.

Karol has no idea what it's like for us long haired dudes.

Should this get a crossdress tag since he's wearing Judith's maid costume?

Akari said:
Should this get a crossdress tag since he's wearing Judith's maid costume?

Why yes, yes it should...and yet you didn't add it.

I think it's better to ask first if one is unsure.