Okay, sorry for the late reply, here we go, the problem that i'm having is that, the Boss just keeps repeting the same scene, the one where he ask mitsu to ride him. There is no progress after that. Another thing is that, during the two midnight office event( the sex competition and the sticky dick challenge), after you do one of them, shota just disappers. And you can no longer do the the other event. I also tried starting a New start to see if that was the issue but no. I progressed Just as the hint item said to acheive 1420 lewdness to unlock new routes and options, but the boss still was repeting the same event mentioned uptop. I didn't even know that the Boss had a house event. I only found out now because you metioned it.
Without doing the event
After doing the event
The only boss event that appears
