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1.
to have sex with someone without their express consent.
example 1
jimi: dude, did you just rape that chick?
mark: nah man, just gave her a gypsy cuddle.

example 2
girl: what are you doing?
guy: relax, i'm just giving you a gypsy cuddle
by joshandymatt October 23, 2010
 
2.
Sexual assault. Specifically rape.
Do you want a Gypsy cuddle?
by gypsylove67 September 19, 2011