This is a game of Don't Rest Your Head that anonymous reported to /tg/.
(1) - OCD clocksmith with a madness power for ejecting things out of time. Just got robbed by (2)
(2) - Amish auto-mechanic on rumspringa who just stole a lot of money from in laundered campaign donations from (3)'s boss, and is trying to collect money to pay it back before people notice.
(3) A political accountant who is starting to realize money is being laundered in and goes to (4) for legal help on the problem.
(4) a Legal aid who is aware that she is the scape goat for the political system if people find the connection with the money. recently divorced, bought a watch from (1) to celebrate their 5th anniversary and needs to return it.
Game starts with the clock-smith getting dragged into the mad world at the top of the clock tower in the financial district to find that the main clock that officer tock and the clockwork constables set themselves too was broken and kept alternating between 12:55 and 13:03 before rewinding back
The accountant and the mechanic wound up at the news paper to find that their political candidate that the accountant worked for was on trial and awaiting sentencing at 13:30 tonight.
The legal aid was forcibly detained and arrested and was being forced to serve as a character witness in the trial. But since the clock tower was broken the trial kept looping in on itself and never taking place.
Since it was everyone first time playing and their characters were all 'new' insomniacs they had a bit of time exploring the city and the idea of selling memory in return for other memories, Drinking to 'forget', and getting chased around by a rather diligent nightmare called 'The Workhorse'
Turns out the Guilted Citadel ran on, well, guilt. What it did was take the guilt from a person, run it through pipes, which then fuelled the machinery of the citadel. In order to progress further down, the players did not only have to deal with White Knights, but also go through various really cruel and rather arbitrary tests along the way ("You can either forget your parents, or you can make ten random children addicted to crack").
By the end, they got to the bottom floor, where the White Knights guarding the single cell insisted there was nothing in it. In fact, they seemed utterly oblivious to the fact that there was obviously a man screaming his sins as loudly as he could. In fact, so loudly that the voices the party had heard since they entered the Guilted Citadel were all his. But the White Knights insisted there was nothing there and that there never had been and no they didn't kill the cat when it got more attention than them.
So the party approached the cell, only to find a decrepit old man. He told them the most terrible things. He knew exactly what each and every one of them was most ashamed of, and he screamed it as loudly as he could. He screamed about how they had condemned innocent people to slavery under the Wax King, how they had let hundreds of people die to get here, and asked if it was worth it.
When the party killed him, he simply looked at them in surprise. When he was locked up, he had all the power in the world, but when confronted directly, he was just a pathetic little creature.
The clocksmith and the Amish are freaking the fuck out and wanted to get home. In due time they realize that they need to fix the clock tower and that the legal aide needs to find evidence in the trial that can end it quickly and keep the clockwork constables off of her.
The clocksmith tells them that he needs a few tools, and a very specific set of gears to fix the tower, as well as the man power to lift everything as necessary. They end up going to the newspapers to see if they have any leads on such a thing. Two rival news rags basically offer them to kill the other in return for the information as necessary. The Amish mechanics madness ability of 'powerless' is used here rather well to shut down the printing capabilities of one of the newspapers so they wouldn't be killed by hordes of paper boys.
Rather than get any evidence for the trial though the lawyer uses her power of 'tell the world' to broadcast that she died. and the accountant uses his ability of 'don't mind me' to make her roughly invisible.
The tower gets fixed, the court case executes the politician. and everyone makes it back to the real world. The with the politician dead the accountant is out of a job, and the lawyer gets set up as the scape goat when investigators start snooping around the investments. Since he didn't have to pay back any money now, the amish kid gives most of stolen loot to the clocksmith and helps him repair his shop.