Jack-in-the-ass 

When a girls is pride or uptight and you want to have intercourse so you get her naked, uncap a bottle of Jack Daniels, pop it in her ass and flip her upside down so she absorbs the alcohol. This allows her to lower her inhibitions and relax.
PRO-TIP: It may be a few minutes before she feels the alcohol so pass the time with a standing 69!

Man, Carla was being such a prude at the party last night I had to give her a Jack-in-the-ass.

Jack-in-the-ass by K-Train91 April 17, 2017

Jack in the Ass 

A cream of the crop jack ass; An elite group of jack asses that deserves to be classified one step higher.

A jack in the ass cop just searched my car E legally and found nothing like I told him. I wonder why people in town don't respect the law?

You are one sincere jack in the ass.

Jack in the Ass by Hatsitting203 November 14, 2010

Jack in the Ass 

When you go to Jack in the Box but the employee treats you like shit

I went to Jack in the Box yesterday but the Jack in the Ass wouldn’t give me extra sauce

Jack in the Ass by AlphaHormesis November 15, 2022

Jack in the Box ass nigga 

A hater that stays talking breakfast 24/7, A rat that if he knows what's good for him stays out of my trap.

You snitched again dog? Yous a jack in the box ass nigga; always talkin breakfast.

Jack in the Box ass nigga by never talkin dinner July 11, 2011