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What is pull an Oscar?
When a man and women are involved in intercourse, and he feels he would have more statisfaction by sticking his penis in a cup.
Mikey: "hey man, you hooked up with that girl?"
Oscar: "yea"
Mikey: "how was it"
Oscar: "Should have not wasted the time, stayed home and stuck my penis in a cup"
Mikey: "oh man, you're pulling an oscar"
pull an Oscar - video
Pull an Oscar - what is it?
The act of receiving a tattoo while in a state of inebriation.
Check out the kanji character on that girl’s back. She sure did pull an Oscar.