The first of many fingers to explore the new world, which is a girl's anus.
"That finger is a pioneer, the first one to land on Plymouth Rock!"

"Most girls want a pioneer finger, even if it's just to the knuckle."
by ThugLuvBonerJamz September 30, 2015
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The first of many fingers to explore a girls anus
I bet Christopher Columbus was the pioneer of pioneer fingers.

"All girls love pioneer fingers, even if it's just up to the knuckle" - Christopher Columbus
by Gstrangs October 4, 2015
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