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Ok, so I bought the costume from the pink bear and topped Shiba twice, once as a sub and once as a dom, but the costume still doesn't show up in the selection. Am I suppose to top Shiba before I buy the costume? 

you have to wait and keep visiting him weekly, at some point it will  triggers after being with him in the morning

also i made a cg guide, if you want here's the link: ♡

I got it! It took ~50 days of having as much sex as possible but I finally got it! Also, it's visiting him in the daytime after the voice acting lesson, not in the morning. Thank you!

Hey, I saw your guide and in Shuu's route, you get the 6th cg by giving Shuu a blowjob, not the other way around. Thanks for the guide tho! It's a lot of help.