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1.
Sexual euphemism for a one-guy/three-girl situation, in which the women are on all fours facing the same direction with their rears raised, and the man is inserting his penis into the girl in the middle while inserting fingers from his left hand into the woman on the left, and fingers from his right in the woman on the right, in a motion reminiscent of an oil pump.

(Extended version of The Dip, which involves only one woman and one man.)
Last night, I got these three chicks to let me give them the Triple Dipper.
by CRAS Hole September 24, 2009
 
2.
When a man "dips" his penis three and no less times in a woman's anus and then proceeds to have vaginal intercourse with that woman or another.
Dude, I totally gave her a triple dipper last night!
by thebigdipperz45 May 19, 2011