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36.
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.
Yo Dave is such a hobosexual.
by Urban Dictionary June 02, 2006
 
37.
One who considers the homeless as sexual beings; one who likes to have sexual encounters with dirty strangers; one who dresses in a homeless person's costume for role playing in sexual enjoyment
My husband and I like to have sex in the dirt.We are hobosexuals.
I'm such a hobosexual, I would totally bang that dude over there holding up that cardboard sign.
I haven't showered today, I feel like a hobosexual.
by Amnika Maypry July 15, 2008
 
38.
(Adj)
1. One who must have a homeless person for their partner.
2. One who feels sexually stimulated only by a homeless person.
Person 1: Dude you have to hear this. Last night I was going over to Jenny's house for a project that we had to finish, and I saw a bunch of men in dirty clothes in her room... they looked like homeless people.

Person 2: Oh my god... what does this mean?

Person 1: She's hobosexual.
by Roberto Millero December 05, 2007
 
39.
a human that is a hobo, and/or resembles one
That hobosexual grows nice apples.
by Michael Bordelon August 07, 2008
 
40.
A gay dude with a cold.
"Yeah, it's true. I'm -achoo- a hobosexual."
by Lenses December 09, 2007
 
41.
A man or woman of any sexual/affectional persuasion or preference who is rated as a disappointment within the realm of surrendering to the exigencies of physical love; a Bum fuck
"I thought that Darlene was as pretty as a bowl of tits," Sydney said, "but when we slipped between the sheets and finally got down to it, she turned out to be a hobosexual."

"Wassathat?" Tommy barked.

"A bum fuck!"

by Twathenge April 21, 2006
 
42.
A metrosexual who doesn't have any money.
He could be a metrosexual instead of a hobosexual IF he had a job.
by Dr. Luv December 08, 2007