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This game is very linear, there is no wrong way to progress with characters. At the end of the day you will basically have to progress almost every kink with every character in order to move the story forward.

As for specifics on your issue, you could check Ran's page in the game's wiki.

https://wiki.blackcatstudiosdev.com/wiki/Characters_(GO)

Thank you for the reply. I've tried to follow Ran's wiki page. Not sure if there's a hidden lock-out, if you progress the story too far, maybe? (I started Kubas stuff.) I go to Ran with high lust, and he takes me to his office, but it's the same scene. I tried now for several in-game days to raise my lust and go to him again and save my progress at the end of each day. Even with as low HP/stamina as I can go (10) and as high lust as I can go (100), it never progresses, no matter how many times he takes me to the office for "punishment." I can't trigger the gameover 1 scene and the end-of-day progress screen doesn't show any "pup" scene completed. Not sure why. 

I wonder if the issue is not being able to trigger the gameover 1 scene? Even with 10 HP/stam and 100 lust, it never triggers during the desk scene. Maybe it's the wrong scene for the gameover? The wiki isn't specific about it.  

Thank you for your help. It's good to know the game guides you forward to some degree to complete the story. I hope I can figure this issue out.