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Description
Project Moon vs Hell's Paradise
Connections
Credits to Caski 16
Both are assassins that started from nothing and underwent intense training from their elders, eventually rising to be a legendary killer in their circles (the Hollow and the Black Silence respectively.) At some point during the peak of their careers, they met a woman that they instantly began to build a bond with (Yui and Angelica), softening them up and coercing them to quit their jobs as killers. However, their decision costed them basically everything, forcing them away from their families and into an unknown realm filled with abnormal monsters (Kotaku and the Library), forcing them to fight other visitors of the place there for their own goals (other death row inmates and ibrary guests.) There, they were monitored by a woman of superior power (Sagiri and Angela) on a quest to find an item that would promise them their freedom (the Elixir of Life and the ultimate book.) While initially combative with their overseer, even fighting and threatening to kill them at times, they eventually learned to respect them over their period in the unknown land.

TL;DR: two insanely skilled assassins driven by their love with family and their desire to see a better future for themselves stuck in an unknown land.

Description
Project Moon vs Hell's Paradise
Connections
Credits to Caski 16
Both are assassins that started from nothing and underwent intense training from their elders, eventually rising to be a legendary killer in their circles (the Hollow and the Black Silence respectively.) At some point during the peak of their careers, they met a woman that they instantly began to build a bond with (Yui and Angelica), softening them up and coercing them to quit their jobs as killers. However, their decision costed them basically everything, forcing them away from their families and into an unknown realm filled with abnormal monsters (Kotaku and the Library), forcing them to fight other visitors of the place there for their own goals (other death row inmates and ibrary guests.) There, they were monitored by a woman of superior power (Sagiri and Angela) on a quest to find an item that would promise them their freedom (the Elixir of Life and the ultimate book.) While initially combative with their overseer, even fighting and threatening to kill them at times, they eventually learned to respect them over their period in the unknown land.

TL;DR: two insanely skilled assassins driven by their love with family and their desire to see a better future for themselves stuck in an unknown land.