Puddin' Poppin'

Puddin' Poppin' is the sexual act of doing Jello shots out of another person's anus. It's name is derived from the Jello Pudding Pops that were popularized by their advertising featuring Bill Cosby.

Incidentally, if you do your best Bill Cosby impression when describing the nature of Puddin' Poppin' to friends or acquaintances, the comedic factor rises exponentially.

Have you heard about Puddin' Poppin'? Apparently, it's really popular with the college crowd.

Puddin' Poppin' by JohanGasmask October 16, 2010

Poppin' The Puddin' Cup 

Much like "Popping The Cherry", except this term implies the loss of Anal Virginity.

Man, Kate was so happy last night we were Poppin' the Puddin' Cup till 2 Am!

Poppin' The Puddin' Cup by Bill Costby January 4, 2015