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jailbait and switch 

A cougar dressed in a schoolgirl outfit
My friend thought he was hooking up with a tight little chick, but turned out to be a hag pulling a jailbait and switch.
jailbait and switch by Mrs Plow December 1, 2010

jailbird 

Someone who consistently gets sentenced to jail time and doesn't care. If they have to do a 4 year bid they would just eat it up like its nothing. They eat, sleep, and think jail and are institutionalized. When released, they have a hard time reintegrating back into society and are likely to somehow end up right back behind bars.
Person 1: Did you hear Ramón got locked up again?

Person 2: I'm not surprised. He's a jailbird. That's all he knows.
jailbird by haanspeedball July 9, 2016

jailbait 

An attractive underaged girl who you'd like to bang. But if you get caught banging her you'll go to jail, so she's the bait that lures you into the jail cell, hence the term jailbait. Is similar to a lolita, except the term jailbait only applies to an attractive underaged girl that you want to bang, while a lolita is an attractive underaged girl who also wants to bang you
R. Kelly's next concert is gonna be in cellblock 4 cuz' he got caught messin' with jailbait.

Guy #1: Hey man, look at that girl over there she's really cute, I'm gonna go kick some G to her.
Guy #2: Naw man, that girl looks like she's about 14. She's fuckin' jailbait, dude.
jailbait by Joey Bishop March 8, 2004

Jailbreaking

The process of opening your iPhone, iPod touch, or iPad to many new possibilities. While Apple allows you to install most apps, jailbreaking allows you to install apps apple doesn't like, as well as tweaks (things like an alarm clock that requires math to unlock, to make sure you're truly up), add-ons (iPod controls in Notification Center), and Themes (change the icons, sounds, and system images of your device, giving it a unique look. You can also fix bugs with iOS before apple does, use your device as a wireless flash drive, change your brightness in 2 seconds flat from anywhere, remove ram restrictions (apps run much, much faster, but some battery life is wasted), tap to unlock instead of slide to unlock, download and save youtube videos to watch offline (or if you think they will be deleted), private browsing (for all your porn needs), terminal access, FaceTime and other restricted apps on 3G, video wallpaper, make your home screen look and work like Android or Windows Phone 7, change system fonts, get "unapproved" apps rejected from (too hot for) the App Store, open a text message from anywhere, customize actions (play music when you plug in to charge (or come home with a date), open a favorite app when you shake your phone at the home screen, etc), extend volume WAY over Apple's limit, and lots more!
You: "I just finished jailbreaking my iPhone! Now I get ALL my $600 worth!"
Jailbreaking by Lphil March 15, 2012

jailblazer 

the destruction of self and team through your own careless, stupid, and often illegal activities. In other words, squandering the sum of the parts. Nickname given to the NBA's Portland Trailblazers for obvious reasons.
Fan 1: "I can't believe the Blazers lost again."
Fan 2: "Hard to win when half your team is facing drug charges and the other half just doesn't give a crap."
Fan 1: "well, I suppose they don't call them the jailblzers for nothin'"

Student 1: "dude, got some weed in my locker - let's go"
Student 2: "hey jailblazer, we got our team presentation in 2 hours!"

Monica: "do you need some intern services?"
Bill: "I'm so glad you asked, that way I won't get accused of forcing myself on you, like Paula, Kathleen, and Juanita."
Monica: "why, you little jailblazer..."
jailblazer by workinglate February 8, 2007

Jailbait 

An underage boy or girl who is sexually attractive. Typically young teens who aren't aware of their status. If you DO end up getting with one, it'll land you in jail. That's why they're BAIT.
"Dude, look at that girl/boy over there. What a cutie~"
"Bro, they're like 15. Total jailbait man, back off."
Jailbait by giomanach July 22, 2014