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Tear Jerker: Hivefled
Reprise was so sad its requester felt guilty and is now collaborating with its writer to create the plottier and more hopeful spinoff Hivefled to give the characters a better happy ending. Now that's an achievement.
The first time Gamzee is raped, then has to clean himself up alone while wishing his friends were there.
Tsukey Morney, Tavros' palecrush, is captured and tortured. The reader at first thinks she's just dead, but then the Kin answer some questions... and all she says is "Yeah... Tsukey will be brave." After everything she's gone through, it's enough to make anyone cry.
Speaking of Tsukey, it turns out that she's not actually part of the Kin, she's just staying with them because she thinks she's let everyone down and that Lereal will hate her.
Because of the Signless's blood mutation, he and the Disciple could never turn in a pail. Before the Signless's execution the Condesce and Grand Highblood raped him while forcing his family to listen, and it's implied that they did this at least partially to torture the Disciple with the knowledge that all his descendants would be theirs instead of hers, and that they would ensure that those children would be in exactly the same situation their ancestor was. Doubles as Nightmare Fuel.