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1.
The act of pulling out of vaginal intercourse and engaging in imprumptu and brief anal intercourse and yelling "Surprise!!!"
Tom was getting it on with sue when he suddenly pulled out, shoved it in her a$$ and yelled "Surprise!!!" He never saw sue again.
by King Kong June 18, 2003
 
2.
When a woman is giving a dude a blowjob, but she's not doing it very well, so he yanks it out of her mouth, bends in half, and sucks himself off right in front of her.
Monica Lewinski was really upset when she was blowing Bill Clinton and he got impatient and showed her the Nantucket Surprise! Cigar smoker alright ... and I heard he DID "inhale".
 
3.
Any surprising incident encountered while on Nantucket Island, MA, such as gifts or occurences. See surprise. See also nantucket
Last time I went to Nantucket, I was surprised to see not that many drunken Kennedies.
by King Kong December 15, 2003