In the video "Dear Gilligan," we see the protagonist, Gilligan, being held captive and subjected to intense humiliation and degradation by an anonymous person. The captor, who remains off-camera throughout the video, forces Gilligan to write letters addressed to themselves, revealing their darkest secrets and desires. As Gilligan writes these letters, they become increasingly distressed and broken down emotionally, eventually breaking down in tears and pleading for mercy. The captor continues to taunt and humiliate Gilligan, asking them to engage in self-harm and other degrading activities on camera. The video ends with Gilligan, reduced to a quivering mess, promising to do anything the captor asks if they will just release them from this living nightmare.
