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1.
This is used to describe what happens when a man tries to have sex with a woman in the middle of the night and accidentally misses his intentional target and instead ends up trying to get in the outdoor.

Note on usage: The "accidentalness" of the midnight tragedy is debatable depending on the situation.
Bill: "Wow, you were pretty hammered when you left the bar last night. How'd the evening turn out?"

Jack: "So so. I had a midnight tragedy with Sarah when I got home. She wasn't happy."
by Fernando Anando October 26, 2007

Words related to midnight tragedy

outdoor anal sex backdoor accident anus but sex wrong hole