Top definition
The act of stretching ones scrotum over ones head.
Then performing sexual acts such as oral sex and making out.

A Jamestown Boy is only possible with at least one male.
So How about them Jamestown Boys?
Lets say we go behind those bleachers and try a Jamestown boy?
I tried a Jamestown Boy and now my sack hurts.
by Ivan M. May 31, 2007
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