Homeless Stories

3,543 results
Orientation
Length
Source
Infinite Scroll

My Struggles with Trupti Ch. 01

by urbanslut on Feb 6, 2018
Exhibitionist & Voyeur

There I sat, naked and bound to a chair. The rope was tightly bound over my boobs, digging into my nipples, hurting them, making my massive boobs look like four globes instead of two. A rope ran over my crotch too, digging into my labia, rubbing against my clit, creating a painful yet pleasant sensation. Trupti stood a few feet away from me. Also completely...

Charitable Contributions

by j267 on Apr 20, 2020
Loving Wives

Trish, my wife of a dozen years, had just returned home from dropping our two kids at their grandparents when the temperature started to drop. The forecast called for a deep cold snap and we planned to enjoy it by spending our time with a glass of wine by the warm fire before moving to the bedroom. "Wine!" she called out from down the hall as she changed....

The Empathetic Girlfriend Ch. 02

by StudStory on Sep 13, 2017
First Time

This work is copyrighted under the Creative Commons Attribution-Noncommercial-Share Alike 3.0 license, which means it may be modified as long as the modifier uses the same copyright license and is used for noncommercial use. -------------------------------------- The sun shining through the window woke Yuna up from her sleep. She found herself lying on top...

From Haiti to Japan Ch. 01

by Samuelx on Sep 16, 2017
Interracial Love

"Samuel, I'm sorry but I'm just not interested, besides, I'm with someone else," Esther Voltaire said to me, after I confessed my feelings to her. Esther, the queen of the Haitian Adventist church of Ottawa, and the gal I've worshipped since High School. One bright Saturday morning I decided to tell her how I feel, and as you can see, the results were less t...

Somewhere Over the Rainbow Ch. 01

by SusanJillParker on Sep 15, 2017
Non-Erotic

Susan's asked to leave Hannah's spare bedroom in Hershey, PA. Susan sat on her twin, lumpy bed in Hannah's small, spare bedroom talking to herself through her tears. Albeit much better than living at the shelter, she was still unhappy nonetheless. Without having a car or money to travel anywhere, she felt much like a prisoner living in a 12' by 12' room in...

Pennies

by BigGuy33 on Sep 26, 2017
Romance

My good friend StangStar06 recently published a romance (8 Mile) about a homeless woman with red hair, just like there is in this one. The stories themselves are different and I actually wrote this story months ago but only recently finished editing it. I just didn't want anyone to think I had stolen any ideas. ROCHELLE It was a chilly night but not col...

Hear no Evil

by R410a on May 11, 2020
Romance

This story is the result of a request featuring a deaf homeless woman. This is more story than sex although the two main characters do finally reach that end. Anyone engaged in sex is 18 or older * Hear No Evil I was washing the sidewalk in front of my produce store just as I had thousands of times before, a store that had been started by my Korean grand...

Solace & Rosanna Ch. 20

by Alacia on Sep 13, 2017
Novels and Novellas

2003: The homeless woman stared up at Solace’s window. Her bony fingers lightly gripped the handles of her ancient shopping cart, which contained her entire life. Her eyes blazed with determination. She wore a tattered tee-shirt with the phrase “Isn’t It Ironic?” emblazoned in large, red letters. Surprisingly, her jeans and sneakers were in relatively good c...

Just Another Sunday Afternoon

by fantasex13 on Sep 19, 2017
Erotic Couplings

As usual, this morning, my wife, and I woke up to the sun shining in our bedroom, the sounds of birds welcoming the new day, and had really great sex as she screamed thank you, thank you, thank you, thank you! This has been our Sunday morning ritual for the last six years. After she has had an oral orgasm, where she screams Alleluia, and then a fucking tha...

Dreamboat Ch. 01

by SleeperyJim on Dec 18, 2018
Novels and Novellas

Usual standard declarations about age, etc. apply here. I like writing long stories, and this one drifted into becoming a novel-length story in the planning. I've dropped the first couple of chapters in to test the waters, so I hope you like it (no sex in the first chapter though – it takes a while to set things up). It covers a multitude of genres, so hope...