When you put two fingers in a girls vagina and two fingers in her ass. You then proceed to wipe your fingers just below her eyes so it looks like she has Native American war paint.
Sean was trying to fuck this one chick last night, unfortunately his penis was much too small for her so he gave her the trail of tears instead.
Contrary to popular belief, the Trail of Tears isn't the strip of hair from a girl's back to her asscrack. It is actually the name given to a particularly hairy man's happy trail, or trail of hair starting as far north as the chin and ending in the pubic region. Some men's Trail of Tears are so hairy they actually do not have a distinct path and may continue onto the rest of the man's belly or chest.
When Zack Martin took off his shirt for the swim meet, we all got a really good look at his Trail of Tears...