What is Jailbaited?
1.
Having a relationship with someone underage and only discovering this much later on in the relationship.
"Hey man you look upset"
"Yeah, well, you know Carol?"
"Sure, your girlfriend for the past 4 months"
"Turns out she just turned 15"
"Oh...did you two ever....?"
"Quite a lot, yeah"
"You've been jailbaited!"
See
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1.
when you stick small objects, e.g. cherries or bananas, into your ass and then launch them at something.
"I dated this one chick a..