Homeless Stories

3,543 results
Orientation
Length
Source
Infinite Scroll

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...

Rosanna Pansino's Pervy Challenge

by Swallows998 on Sep 13, 2017
Celebrities & Fan Fiction

"Hey guys its Ro and I'm here with my sister Mo! Today we have a special guest, a random homeless man we picked up from the street!" The two beautiful young ladies present the filthy man between them, a disheveled homeless man with a clear bulge in his pants. Rosanna and her sister Molly are wearing a salmon pink and a light blue blouse respectively, covered...

Without Remorse Ch. 01

by shandal on Sep 14, 2017
Novels and Novellas

This is a crime thriller with some romantic sex, a smidgeon of violent non consensual sex and interesting by-play between various characters whom I hope you'll enjoy reading about. It has ten chapters, and I do hope you enjoy reading it as much as I enjoyed writing it. Definition of a Sociopath -- someone unconcerned about the adverse consequences for othe...

"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...

My Late Night Subway Ride

by pink2468 on Sep 12, 2017
Exhibitionist & Voyeur

I was riding the subway late at night. I had left a friends house after having a few and decided to take the subway so I didn't have to pay for a cab. We had originally planned to go out clubbing, but ended up just hanging out at her place until late. When I got on the train there was just a couple, a homeless guy, and me. The homeless guy stared back and fo...

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...

Public Transportation

by ShaylaStriffler on Nov 6, 2018
Exhibitionist & Voyeur

With the lousy, icy weather we have been experiencing lately, I decided to ride the bus to get to and from work. No need to risk wrecking my car on the slippery roads. On my way home after work one night, things got a little more interesting. I had my heavy coat on over my white blouse and skirt, but it was really warm in the back seat of the bus on the rid...

Dirty Secrets

by azzure1020 on Sep 16, 2017
Interracial Love

Chapter 1 Hell on earth is a crowded subway train at 6:00 a.m. in the morning, Adele thought, looking at the bent heads and blank faces of her fellow straphangers. She rode the number two train downtown to 23rd Street, where she played executive assistant to her psychotic boss: Mindy Corentini. Mindy was a trust fund baby. The only child of Apollo Corenti...

The Slut Truck

by slutluva on Jul 24, 2018
Group Sex

A regular Jordan fucker, Taylor, a carpenter friend of ours, modified one of his ex-work vans to be a mobile glory hole toy. So far the only slut that's used the slut truck has been Jordan. Then again Taylor does come around Jordan's work with the van and his apprentice to fuck her during the week. Some weekends Taylor has to stay home with his wife so Jord...

Julie's Climb Pt. 01

by TheLucasDaden on Sep 16, 2017
Novels and Novellas

Her name is Julie, she's four feet eight inches tall and light maybe one-hundred pounds soaking wet. Her hair is red, long and not terribly well kept, she wears no makeup but her green eyes shine when she looks at you. She wears a dirty plain white t shirt that's too big over a old ratty purple sports bra that holds her pleasantly sized C cup breasts, old ta...