Homeless Sex Story Stories

265,341 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Old Bag Lady is a Recycling Witch

by SuperHeroRalph on Sep 25, 2017
Sci-Fi & Fantasy

This is a Earth Day contest story. Please vote. * An old, bag lady takes a liking to a man who has shown her kindness. I'm the type of person who always reaches in my pocket to pass out spare change to homeless beggars. I don't think twice about it; I just do it. Not the best that I can do, it's the least that I can do. What is just loose change to me, ma...

A Small Price To Pay

by PositiveThinker on Sep 14, 2017
Non-Erotic

I dedicate this story to Bostonfictionwriter, who helped me get off of drugs, gave me a place to stay, and found me a job that paid enough to keep me off the streets and out of the shelters. Most of the story you are about to read is true, just the names have been changed. There is no sex in this story, just emotion. * There's no better day than Earth Day...

"Will You Be My Valetine Day Date?"

by SusanJillParker on Sep 12, 2017
Non-Erotic

This is a Valentine's Day contest story. Please give me the support of your vote. * Memories from the past, this is a true recount of a man who tries to pick up a woman at McDonald's as his sexy Valentine's Day date. After losing everything in a flood, there was a time when Susan Jill Parker was homeless, sleeping at a shelter, and eating at a mission. No...

Without Remorse Ch. 02

by shandal on Sep 14, 2017
Novels and Novellas

This is a crime thriller with some romantic sex, and a smidgeon of violent non consensual sex and interesting by-play between various characters whom I hope you'll enjoy. Ten chapters long it tells the story of an investigation, with many characters weaving in and out the story. Definition of a Sociopath – someone unconcerned about the adverse consequences...

Who is the Writer, SusanJillParker?

by SusanJillParker on Sep 13, 2017
Reviews & Essays

An up close and personal look at the writer behind the stories. I've been busy writing, since I joined Literotica on January 1, 2007 and before, of course. I started writing, when I was 13-years-old. Graduating magna cum laude with a 3.65 grade point average, I received my bachelors degree in English from Northeastern University in Boston in 1999. I nearly...

Collecting Bottles, Cans & Friends

by SusanJillParker on Sep 19, 2017
Novels and Novellas

This is an Earth Day contest story. Please vote. Homeless and destitute, prostituting herself for money to survive, a woman collects bottles and cans, while making friends. * "Hi," said the man to Susan passing by her in the alleyway, while staring. Accustomed to men staring at her, such an unusual sight to behold, men don't normally see a woman who loo...

The Empathetic Girlfriend

by StudStory on Sep 13, 2017
First Time

Greg and his girlfriend Yuna were driving back from a movie when their lives changed forever, although neither knew it at the time. They were returning from a romantic movie although neither could explain the plot. They made out during most of the show and Greg hoped to have sex with Yuna after they got back to her apartment or at least get to third base. Th...

Eddie Silver Ch. 02

by PrincessErin on Sep 1, 2017
Humor & Satire

Ruth was enjoying a relaxing time in her bathtub. She had just gotten home from the homeless shelter where she worked. It had been a busy day as the cold Boston winter had set in and those men who normally were too stubborn to come in for a hot dinner had finally conceded. She was enjoying a glass of wine and was going to cuddle in bed with a book. Ruth was...

How I Became Alison Ch. 02

by JayDeviant on Oct 24, 2018
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I had told you about how I had met old Mr. Spandwick and how he had insisted on dressing me up like his granddaughter, Alison, before having his way with me. Pretty hot, right? I thought so too, but it did freak me out a bit... It just wasn't the kind of thing I had ever done befo...

HOMELESS & HUNGRY

by Bondage4u on Apr 29, 2025

THIS STORY WAS REQUESTED BY A CERTAIN DEVIANT ON HERE, HE HAS A HUGE CRUSH ON JENNA ORTEGA! "Thank You, thank you so much sir” as he opens the door and allows the young, homeless urchin to enter his domain, “I promise you won’t be sorry you took a chance on me sir, I’ll make you very happy whatever you want or need me to do I am very obedient…what is yo...

Open in Reader