What is Pin The Tail On The Donkey?
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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.
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