Pin the Tail on the Donkey 

When you're about to have sex with a girl on her period... you turn out the lights so it's dark, flip her around into the doggystyle position, bend her over, pull her tampon out, and attempt to stick it in her ass in the dark as if you were blind folded and trying to pin the tail on the donkey. Upon completion, sex is mandatory but the return of the tampon to the vagina and/or Donkey Punch is optional.

"Dude, my girl was on the rag last night so I had to play a little "Pin the Tail on the Donkey" to get a piece.

Pin the Tail on the Donkey by Daniel Patrickk December 17, 2006

pin the tail on the donkey 

While having sex doggystyle and wearing a condom after finishing the male pulls off the now full condom inside out while getting the female's attention so she turns to look back at him, so he can then stick the condom between her eyes thus having pinned the tail on the donkey/ass.

I'm definitely goin to pin the tail on the donkey tonight when I'm done with that chick.

pin the tail on the donkey by MediumNasssty April 3, 2022