Top Definition
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.
by Daniel Patrickk December 16, 2006

The Urban Dictionary Mug

Lotsa space for your liquids.

Buy the mug

The Urban Dictionary Mug

Lotsa space for your liquids.

Buy the mug

The Urban Dictionary Mug

Your favorite word on a white mug.

Create a mug

The Urban Dictionary Mug

One side has the word, one side has the definition. Microwave and dishwasher safe. Lotsa space for your liquids.

Buy the mug

The Urban Dictionary T-Shirt

Soft and offensive. Just like you.

Buy the t-shirt

The Urban Dictionary T-Shirt

Smooth, soft, slim fit American Apparel shirt. Custom printed. 100% fine jersey cotton, except for heather grey (90% cotton).

Buy the t-shirt