Originates from the movie Vanilla Sky. When your f-ing a chick and you confuse her with another girl, but continue to have sex with her (usually even harder).
I pulled a Vanilla Sky last night; I was having sex with Racheal, but then I thought it was Lindsay, so I used the moves I that pleasures Lindsay. It gave Racheal a triple orgasm.
by Trip Aces January 5, 2005
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i looked up at the sky and a bird poo went in my eye and i say @#$@#$!. screw this @#$#@ vanilla sky
by GXBJB September 23, 2003
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A really good movie starring Tom Cruise. It gets confusing a little bit but the climax is amazing.
Let's watch Vanilla Sky.
by sagzag June 23, 2004
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To 'Vanilla Sky' somebody is to fuck them 4 times and then drive them off a bridge.
Guy 1: Wow Kate is kind of hot. I'd sure like to Vanilla Sky her.

Guy 2: Oh really?
Guy 1: Yeah, totally bang her over and over and then be done with the world, ya know?
by SomeThingsAreRealFuckedUp April 25, 2021
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Dude: Hey baby you wanna watch Vanilla Sky tomorrow night say around 10.

Girl: Oh yeah. Good thing I took the pill this morning
by Tiger RAARRRR May 2, 2008
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The concept of vanilla sky is basically:
Sign up to LE (Life Extension) and when you die, your body will be taken and frozen, you will be connected to a machine and live on in a dream. Your death will be erased from your memory. You make your own dream, useing images, films and songs which moved you.
The 'Vanilla Sky Moment'
When we learn something, discover somthing, or are reminded of something we had forgotten, it appears in our everyday life without interference of ourselves or anyone else. This can be seen as our mind or our 'dream world' using this in our life.
Woah man i had the worst vanilla sky moment just then. Earlier i was watching MTV Base, which i hardly ever watch, and 'Obie Trice' 'Got Some Teeth' came on, i hadnt heard that song in ages....i forgot it existed. And then i turned on my ipod, and the first song was obie trice got some teeth!
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The strange feeling you get after watching the picture "Vanila Sky", with Tom Cruise.
«Look at Matt, crying like a little kid, staring at the moon... is he drunk?»

«No, we had just been watching Vanilla Sky *sigh*, he got Vanilla Sky hangover again»

«Oh, I see...»
by fdmg July 22, 2011
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