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Drilling Skins

Another street term used to define or indicate vaginal penetration, usually for multiple females from the same male or the same female but multiple times.
“ I used to stay drilling skins before I got married”.
by NDemGuts February 23, 2021
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drilling for oil

A rhetoric phrase used to mock women in absurdly high heels.
by Gumba Gumba April 4, 2004
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drilling for oil

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 Michael Scot Phisher Pfisterly September 23, 2011
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Drilling for oil

Anal sex with the intent of diarrhea.
"Hey guys,I'm going drilling for oil tonight."
by Jiggly-jizzly69 October 20, 2017
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Drilling for oil

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 8, 2010
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drilling em

It is often used from the people called 'roadmen'.
It means to shoot up a group or gang .
In the song 'redrum reverse' from R6 67, it is used to show a threatening fallacy to express their anger.
'Cuz dem youts be chatting shit , in 5 minutes we should be drilling em'
by Jdadlani1304 January 16, 2018
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drilling taters

to hit several homeruns in MVP baseball '05
'the cubs were forced to go the bullpen early in liue of the 16 taters that were drilled off the starting pitcher'

'i shellacked 37 dingers, also smashed 12 round trippers, and ultimately was drilling taters 88 consecutive times, shattering the single season record'
by Twitzle to the tweezy December 6, 2007
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