While squatting over a girl, the act of first placing the entire nut sack in the anus and then the shaft into the vagina and continuing intercourse.
Dude #1 : "Did you hit her with the oil drill last night?"
Dude #2 : "Oh yeah, I struck it rich!"
by K-Bone January 31, 2008
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Involves two men and a woman; where one guy has the woman held up and she's riding him, while leaning backwards and getting tea bagged by the other guy (can be altered by sucking him off)
Gordon lifted Christina and she leaned back so Josh went and tea-bagged her...David came up with the name the oil drill for it.
by J-Killin December 18, 2008
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When one is having anal sex with someone, the reciever squirts diarrhea out of their anus and onto the penis of the other person, as if they have struck oil
Person 1: Woah, you got anal?!
Person 2: Yeah but they pulled an oil drill on me.
by pugnificent August 23, 2015
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When you buttfuck a chick so hard that she shits on your dick.
Did she shit on your dick?

Yeah, I oil drilled that bitch.
by shartattack2014 August 21, 2014
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When in the act of anal intercourse, the woman profusely defecates over the mans genitals after it falls out of the woman's genitalia.
Damn man, I was Oil Drilling Sarah so badly that I had to take 3 showers to get the smell of her shit off my dick.
by Stu Feiner October 21, 2020
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When someone diarrheas on a man's penis and he uses it at lubricant to fuck them, either anally or vaginally.
"I still can't believe you wanted to try Oil-drilling last night! What if you caught my flu?!"
by Eleven Tails February 15, 2020
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While receiving fellatio from a woman, the man positions her in a horizontal position and crouches above her mouth. He inserts his manhood into her oral cavity and begins to thrust. When finished, the man ejaculates in her mouth, jumps up and screams black gold! He then sprints out of the room and never speaks to her again.
Justin caught me totally off guard last weekend when he decided it would be a good idea to start oil drilling me, and now he won't answer my phone calls.
by LennyLenLen November 4, 2008
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