In Canto XXI, Dante and Virgil make their way to the fifth chasm, which is very dark and filled with boiling pitch. Dante compares the pitch to the material used to caulk the seams of ships. Suddenly, a raging demon appears, and Virgil hides Dante behind a large rock so he can go to the demons and make a deal for their safe passage.
The demon is carrying a sinner, which he tosses into the pitch, saying that he is going back for more sinners to place in the chasm of Grafters. The other demons warn the sinner to get beneath the pitch or the sinners will taste their grappling hooks.
Virgil confronts the demons, and they threaten to harm him. He asks to speak to one of them, and Malacoda, leader of the demons, steps forward. After hearing about Virgil's divinely inspired journey, Malacoda grants the poets safe passage and rounds up a group of ten demons to escort them to the next bridge. The poets must travel on the next bridge, because as Malacoda tells them, the closest bridge fell in an earthquake 1,266 years, one day, and five hours from the present point in time (indicating the Harrowing of Hell on the day that Christ died).
Dante is afraid of the demons and pleads with Virgil to go on without them, but Virgil reprimands him for his fear and reminds him that the demons are there only to guard and torture the sinners in the stew of pitch. After a vulgar sign and countersign between the demons, the poets move on with their escorts.
