Top Definition
verb. To have your penis slip out during sex and accidentally insert it into the anus.
Guy 1: How was the sex last night?
Guy 2: It was awesome until I accidentally gave her the midnight surprise, then she ran out crying.
by theaLyssavirus May 13, 2009
When your girlfriend is sleeping soundly next to here and all of a sudden you jizz all through her hair without her realising.

She'll wake up the next day and freak out.
"yeah, totally gave Catherine the midnight surprise last night"

"Maaate, I midnight surprised her while she was reading the Kite Runner, total bad move on my part"
by Jackbot February 17, 2009
Secret acts of fun performed by girls, nationwide, at midnight. Origin: Trinity College in Hartford, CT.

(Term coined by DJ Underberg, NYC.)
i i i im your midnight surprise
better believe your eyes and get ready to play
i i i im your midnight surprise
goin to tantilize you in every way
by THE midnight surprise March 09, 2007
While sleeping with your girlfriend, quickly yank down your pants and sit on her face, after doing so you may let out a large puddle blanket, which may spray fecal matter on the woman's lips and or nose.
Man, While sarah was sleeping I gave the ol' midnight surprise with a swift poop spray to the mouth.
by Shizni January 22, 2007

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