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1.
standing over a women and proceding to squat down into her vagina, similar to an oil rig...and then when you "hit oil" it explodes...recommended to wear a hard hat.
i am going to drill for some oil in your mother tonight.
by jiga boo August 10, 2004
51 9
 
2.
The act of stealth masturbation on a beach, done so by lying face down on the sand and humping the warm ground, creating a hole of pleasure. Easily spotted due to the rhythmic pumping of the hips, not unlike that of an oil well.
When Cindy and her daughter Sam walked by old man Johnson, they noticed their presence had prompted him to start drilling for oil.
by Iroquoi Plissken July 26, 2009
9 5
 
3.
A sexual position in which the man stands over the woman, who may be on her back or knees with her cheeks spread, and inserts his penis repeatedly into her asshole, particularly when she has diarrhea.
Drilling for oil is a highly controversial practice that has fallen into disfavor in the last decade, primarily because of The toxins it can release into nearby areas such as your penis and bedsheets.

Doug put himself in immense danger by drilling Anna for oil without first checking the pressure of the well.

Left-wingers both drill and are drilled for oil but condemn BP and Haliburton for similar practices.
by ConnieOnTheSpot September 22, 2011
4 1
 
4.
Having sex with a woman while she is menstruating.
Guy: "I want to put my dick inside of you SO bad!"
Girl: "Not unless you mind drilling for oil."
Goy: "No...that's okay..." *goes flaccid*
by PickleSnuffler July 07, 2010
5 6
 
5.
A rhetoric phrase used to mock women in absurdly high heels.
Are you drilling for oil?
by Gumba Gumba April 04, 2004
11 15