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Jail Time 

Coined phrase by "JOJO," which is a sex position where the partner is is on his/her back, with legs 90 degrees in the air and the penetrating partner's face in between those legs as if to look through jail bars.
jail time is example of a prisoner holding jail bars and looking through :-)
Jail Time by team esto November 21, 2013
Related Words
Cuffing season
A term typically used by males to describe a hot female displayed in one of two ways:
Either kill him
Or put him on trial
Because what happens afterwards is out of his control
Example 1
"Have you seen Alyssa today?"

"Yeah bruh I'm on serious jailtime now!"

Example 2
"Jailtime?"

"Dude put me on trial!"
Jailtime by Suck a toe January 11, 2019