Any person who trades sexual favors for a roof over their head regardless if it's overt or finessed.
by Asdvhjitd November 19, 2021

A dude or chick that has sexual encounters in homeless encampments and usually only has sex with homeless people.
I broke up with Eddie because hes a closet/covert Hobosexual. I followed him down to the riverbottom and spied on him as he slammed meth then preformed oral sex on a dirty homeless dude.
by Octilted July 6, 2017

by MandM Productions November 24, 2019

by LBONUDL January 22, 2011

Kate: Sarah, look! There's a homeless man!
Sarah: I wanna fuck him sooo hard!
Kate: You're such a Hobosexual Sarah...
Sarah: I wanna fuck him sooo hard!
Kate: You're such a Hobosexual Sarah...
by DinosaursAreRapists April 30, 2014

A person who is in high school but looks like they are 40 years old. They generally wear the same jacket everyday, ripped sweatpants, and rarely shave or get their hair cut;giving them the appearance of a hobo.
by Urban Dictionary June 11, 2006

Style that is a cross between hipster (or metrosexual) and hobo. Coined by Cobra Starship lead, Gabe Saporta. Only to be used with permission by Gabe Saporta.
by leaax3 September 25, 2009
