To get raped as if you were in prison.
Florida really had jailsex with Florida St last year in Tallahassee.
by Dr Gator September 18, 2013
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To get owned, screwed, hosed. AKA raped.
Johnny: Dude, did you see the Ohio State & Michigan game in the 2010 Big Ten Tournament?

Roy: Yeah, Michigan got jailsexed at the end.

Johnny: I know, that is hilarious! Michigan fans are a bunch of cry babies.

Roy: Yep.
by Snap2ya March 12, 2010
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