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1.
When you reach from behind and through your legs in a bent over fashion with one foot propped up upon an object such as a table or chair.
My mom totally caught me busting out a Jamaican Jerk last night.
by Lickibra June 09, 2008
 
2.
A woman, who is currently menstruating and not wearing any protection, only panties, gives a guy a handjob and lets him cum all over her "Red Stripe".

Red Stripe is usually known as the most famous beer from Jamaica
"My girlfriend is on the rag, and it sounds weird, but that turns me on. She gave me a Jamaican Jerk the other day. It was awesome!"
by Gutterbrain August 28, 2011