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1.
When upon removal of the penis from the anus--after and ONLY after FULL anal penetration (full anal penetration being defined as the scrotum making full contact with the "ass cheeks")--the penis head emerges COVERED in fecal matter.

NOTE: It must be the head of the penis and not the shaft which is covered in fecal matter. A covered shaft is known as a "brown barber pole" and should not be misidentified as "hitting paydirt."
Upon conclusion of a good round of anal sex, Ron gazed proudly at his shit covered helmet and excitedly proclaimed: "Hey, hey! I hit paydirt!"
by Captain Insano July 12, 2004
 
2.
to make it big, to hit the big time, to gain large amounts of money, to generally gain(in a positive way)from something.
(1.)"man that band hit the paydirt with that last song"

(2.)"name's mc, my band's the lee majors put us on the bill, and boy ya hit paydirt when i'm on the mike, girlies wanna flizzirt but I tell'm chill like a dq blizzard" -'DQ Blizzard' by MC Chris
by Erick October 14, 2004