When you succumb to your fetish of having sex with homeless women, but you chose to fuck them solely in the asshole because their pussy smells so vile you couldn't possibly get near it. Much like the blue waffle.
Dude I was totally in a hoboing gang bang last night. Now my dick smells like road kill and the inside of an Iraqi prison after rape night.
When you spend the night somewhere and you realize the next morning that your shirt (or some article of clothing) has become dirty, so you turn it inside out to give a spotless appearance for the new day.
The name hoboing is given to this because the homeless will turn their only clothing inside out when they need to appeal to people.
Fredrick: Yo homes, why do you smell like hooker blood and vodka?
Willis: Because I was at Jeremy's house last night! Im covered in this shit, man!
Fredrick: That shit's crash, bro. But wait, you dont look like you did you have anything on you.
Willis: Thats because I've been hoboing my all my clothes today.
To Hobo it out, (or hoboing it out) is to leave someplace in a hurry while looking muddled and unprepared (like a hobo or bum.)
"Zoe hoboed it out to the schoolbus; her hair unbrushed, a jacket half on and her shoes untied."
"Gabby, with a hand full of loose papers and her backpack still open, was hoboing it home."
To find a outdoor place that is not yours and sleep there.
Lets go hoboing at the beach