did ray worked on a game called TeachingFeeling? If so I'm trying to find it but no luck.

He did, check out https://vndb.org/v18636, spotted the game CG on sadpanda earlier

honestly i thought it was hetza who did teaching feeling when i play the game... these 2 guys got a quite similar art afterall...

Besides Sachi and Akemi who are the rest (tagging Usui Sachi&Tsunemi Akemi) a quick translate gives Eishitahabi(bottom left) Shirakami Genhana (black sclera) and sadokawa something or other (top right)