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.
#jamestown #boy #nuts #sack #head #sexual #face #making #out #oral
by Ivan M. May 31, 2007
10 Words related to Jamestown Boy
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