Extremely deeply-penetrating sexual intercourse (vaginal, anal, oral, etc.), measured by multiplying the length of ones' index finger. (See formula below).

Formula: If your index finger is 3 1/2 inches long, then to go "five deep" would equal 17 1/2 inches of penetration.

Lx5=P where L=Length of index finger and P=Penetration depth
Franco: "Hey, what's your sister up to tonight?"
Jared: "Why do you ask?"
Franco: "I was hoping to go five deep tonight, and she's the only bitch I know who's seasoned enough for that kind of punishment!"
Jared: "I'll kill you".
by Babies August 13, 2006

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