Gay Homeless Stories

25,551 results
Orientation
Length
Source
Infinite Scroll

The Homeless Old Man Ch. 02

by trishotoy99 on Oct 31, 2017
Mature

There was an old drunkard who occasionally appeared in town. Once a week this old fellow would sell jungle produce in the market. He would then buy cheap liquor and drank straight from the bottle. By the time he got to the third bottle, the scenario changed. He would sing and sometimes gave meaningless speeches. There were times he acted aggressively too. He...

Homeless Pretty Woman

by Squishmitton69 on Mar 12, 2019
Mature

Just another Wednesday night, going home after work as the sun is setting. Life has become boring. I go to work selling insurance, get in my Honda, go home and masturbate. My name is Jarrod and I'm a 24 year old man. I'm very tall but average looking. I'm able to pick up girls at the bar but lately that's gotten boring. I've been looking for a little excitem...

Melissa's Legacy Ch. 02-03

by readyforprimetime on Sep 16, 2017
Romance

readyforprimetime This is a work of fiction. Names, characters, businesses, places, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. This story originally appeared as Melissa's Legacy, and was written around V...

Jocasta: Second Session

by emap on Sep 2, 2017
Erotic Couplings

So yes I know a second one took forever, got a little lost in the pile. If you pay attention this one is in a different category than the first, I am going to be an evil bitch about that so there. :p ** I am understandably peeved when I get into work today. I didn't get my black belt, and the only thing different from earning the prior belts is simply, I w...

Inheritance

by thucydides on Mar 14, 2017
Fetish

You wake up on the bus, which is strange considering you don't even remember getting up this morning. Looking around, you notice something is off - you have long hair, and clean clothes, and you're thin, and you have breasts. Your heart starts racing and feel the sudden urge to get some air. You step off the bus to collect your thoughts...What's next? &quot...

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FUCK IT

by Bossfrog on Feb 3, 2019
Cheating Spouses

Aaron Lock, a long time businessman at one of the largest charitable companies in the world. Hug the world, after working for then for over 10 year he has helped thousands of homeless people, helped clean the oceans and helped across seas in poor or war torn society’s. He’s gotten rich and worked to the position of second in command. when his boss Kara woods...

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Gift

by kaiserreich1918 on Jan 19, 2021
Cheating Spouses

An Unknown entity has entered the earth looking for someone who will inherit the power this unknown entity have. This entity circled the world to find not the worthy one but the capable one. This entity can neither be good or bad, does not seek peace nor looking for a place to destroy. A month after looking for candidates, he found several possible people to...

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An Angel's Wish

by Tara_Neale on Sep 14, 2017
Non-Erotic

Keisha Jackson rearranged the few brightly wrapped presents in the trunk of her old SUV to make way for her daughter's wheelchair. How could something so small be so bulky and heavy? "How was choir practice tonight, my sweet angel?" she asked as she worked to get it in around the presents that she had picked from the charity while Breanne was at church. Ir...

Middle Ages Sex Adventures

by knulpul on Jun 17, 2018
Fantasy

Your name is Jenny. You are a homeless girl living on the street and the only way out of your situation is to travel to the Mystic Ponds far beyond the Troll Mountains for this place is said to give mystical powers to those who drink out of them. This could be your only way out of your misery. It is dusk and you walk through your hometown, a little village c...

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From Winnipeg With Love

by Samuelx on Sep 12, 2017
Interracial Love

Greetings, folks. My name is Algoma "Allie" Witashnah and I'm a young Aboriginal woman living in the City of Winnipeg, Manitoba. My father, George is Aboriginal, originally from the Sioux band, and my mother, Beatrice Kensington, is originally from Berkshire, England, but moved to Canada in the 1980s. I am the daughter of two worlds, but fiercely and proudly...