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Sexy Hobo

A Sexy Hobo is a homeless man who might not have any money, but he can show you a real good time in his box.
I am a ugly virgin so I fucked a Sexy Hobo in his box, but he also got me hooked on crystal meth.
by Mystical_Voodoo November 2, 2020
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broke hobo

Lenny- The broke person who sleeps on peoples couches and don’t pay rent
Don’t be a Lenny (broke hobo) when you grow up.
by Broke Hobo March 26, 2021
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Logan Hobbs

Logan Hobbs is a great guy with a massive schlong. He will pound through anyone who gets in the way of his dream of becoming a professional toe sucker.
“Logan Hobbs pounded through my stepsister last night because she wouldn’t let him suck her toes!”
by Myteatsarebiggerthanyours December 10, 2021
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cuddle hobo

This is a term that has arisen in D&D / TTRPG circles where the players just want to adopt everything. It's a bit of a juxtaposition and play off the term "murder hobo" for the players who want to kill everything.
My players have now adopted a displacer cat, three wolves and an owl bear. They are real cuddle hobos.
by Ed DM March 6, 2022
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The Hobbs Tree

The Hobbs Tree is a curious sexual endeavour originating on the southern coast of England. Usually performed by men with unfortunate hairlines and terrible comb-overs, upon their unwitting, and soon to be damaged girlfriends. The male, after a healthy and indeed sloppy helping of foreplay, places their face within their female's vagina, who should be placed on her shoulders facing upwards with her legs akimbo at a 180 degree angle. Upon the disappearance of the face, all that will be visible is the sparse locks of curly, combed over hair, now nestled between two outstretched legs, like the leaves and branches of a tree.
I know me got no hair. But it mean me and julie can do The Hobbs Tree every night, me love the taste of me julie.
by bencurryy May 3, 2022
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Chilly Hobo

The act of inserting both hands inside a women, then rubbing your hands together as if you were a cold homeless person trying to warm up.
I brought a girl home last night and she had me do the “chilly hobo” on her, it was dope.
by Richarazardd July 7, 2022
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Sloppy hobo burger

Two homeless people under a bridge, doing the six 9
Yesterday I saw two homeless people doing a sloppy hobo burger.
by Peepe435 December 27, 2022
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