I'm taking a wild guess and saying they're playing a game of sorts. The more questions you get correct, the more cushions you get. That would explain why Yu has the most. But... I find it odd that Naoto only has two, then. ...I'm assuming if you get a question wrong, you have to strip, which would explain Teddie. As for the image itself... A friend translated the description for me. Apparently the artist just wanted to draw Kanji in a kimono and this was the result. I wasn't sure if that was worth adding to the artist commentary, though.
Grabbed some of the tags. Perhaps they'll provide some context?
Basically, they're parodying a talk show where the host awards comedians cushions when she (Yukiko, in this case) thinks they're particularly funny or witty.
Basically, they're parodying a talk show where the host awards comedians cushions when she (Yukiko, in this case) thinks they're particularly funny or witty.
Welp. That definitely explains Teddie (and Yosuke). Poor, poor Teddie.