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1.
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
68 4
 
2.
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
9 7
 
3.
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
27 32
 
4.
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
3 9