
OKAY I come back after 1000x re-reading this and I hope I understood here we go:
So some of the panel with The past/black panel is actually happening In reality
1. Chester loves Jesse since he’s kid but Jesse has this “I have everything so I don’t really need anything anymore” attitude which twisted the hell out of Chester because he wants to be needed by Jesse and not get abandoned
He also hates how manipulative Jesse is
2. After they grow up (in reality), Chester left the country for some time to study and come back and offer Jesse tea (the beginning of it all) and plug Moritat to Jesse’s head while he’s unconscious for a day (Yes 40+chapters of Moritat is actually happening IN A DAY)
3. because Chester is twisted and always scared of Jesse leaving/abandoned him(which probably just in Chester’s mind) he created Moritat scenarios to TEST Jesse, something like “10001 situations that could make Jesse leave me” that include : Chester killed his parents, Chester betrayed him, Chester is a murderer of Board members, etc.
4. Yet He ALSO make fake scenarios in Moritat (About Jesse parents, company, there is also fake kidnapping and fake video tape) to test if Jesse will choose Chester if Jesse had lost everything,
5. BUT THEN in Moritat there are times when Jesse actually didn’t leave Chester and actually be together with him(when they want to commit double suicide)
6. But that also scared the shit out of Chester (he’s ridiculously weak), because he’s not confident he could HANDLE Jesse if they were together(bcs somehow Chester also hates Jesse)

YOU ARE AN ANGEL... A LIFE SAVER... FOR REAL... SERIOUSLY THANKS A LOT... CUZ I SWEAR TO GOD MY BRAIN WASN'T ABLE TO PROCESS ANYMORE I WAS BRAIN DEAD AND I SPENT THE WHOLE TIME READING THIS MANGA... EVEN THO I WASN'T ABLE TO UNDERSTAND A SINGLE PLOT I STILL KEPT READING IT... FOR A SEC I EVEN THOUGHT THIS MANGA WAS CREEPY...

hiya love the analysis just wanted to add something too.
In the later chapters Law Chester explains how all the nightmares and images he sees are "after images" as they did actually happen in the moritat space.
I think that in this he means that all those "1001 ways to test Jesse", jesse was actually getting short memory bursts from all the different scenarios, but Chester actually lived through all of them. So we only saw one test end when really there were 1000x more ones which ended differently.
Yet i think this was the only time Jesse accepted him so he ended up ending the entire system completely, rather than changing simulation. So im thinking all 1001 happened in a day or so
Chapter 4 and the emperor is already out of character I’m errrr