Comes from the Latin "Risk it for the biscuit". Term was Americanized in the late 19th century. Generally used in situations that are risky.

When some little bitchboy is acting like a little tiny pee pee poo poo baby and messing up the group plans.

A brigade of Pirates in the game Windward known for their fearsome cruelty and fun-loving questing.

Relates to pro-evolution soccer. The term is applied to a situation where a foolish and un-necessary risk is taken but goes unpunished.

When a women is extremely fertile, and it's risky to cum in the biscuit.