Homeless Fuck Me Stories

345,626 results
Orientation
Length
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Infinite Scroll

The Homeless Woman

by jackal1 on Sep 13, 2017
Erotic Couplings

She was standing at the corner of third and market. It was a foggy January morning in San Francisco. I was in town for a professional conference. Lowering the driver's side window of my rental gave me a better view of her. She held a "homeless, will work for food" sign. She was staring into the morning traffic and seemed oblivious of the falling rain. You co...

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...

The Homeless Obsession Pt. 01

by Deckard6969 on Mar 2, 2020
Celebrities & Fan Fiction

A trophy plaything for a wealthy Manhattan businessman takes an unexpected slip from life's pedestal when she finds herself underneath a homeless man -- but discovers it is just where she needs to be! Racquel Darrian had grown tired of being an objectified fashion model -- it was such an empty existence. Something had to change, but what? Her uber-rich boyf...

Salvation a la Mode and a Cup of Tea

by Stardog Champion on Sep 15, 2017
Mature

"Freefall," Rebecca Quinn thought to herself as the elevator lowered her and her Husband down to the lobby of her office building so they could go have lunch together. "Freefall...That's just what my life feels like right now," she had to stifle a perverse chuckle at the irony of the comparison between the elevator and her place in life. Rebecca had been m...

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...

Do You Wish You Were Rich?

by SusanJillParker on Feb 7, 2018
Reviews & Essays

As if your vote is my applause, please vote. * There's no one here but us. Tell me. Do you wish you were rich? If you're not already rich, do you wonder why you're not rich? Why "them" and not "you"? Listed below are SusanJillParker's miscellaneous ramblings of things that are not right and/or not fair with the biggest issue being money. MONEY. M-O-N-E-Y....

Real Property

by peggiesue1963 on Oct 13, 2017
Loving Wives

Shannon stood, bent over, gripping the kitchen counter at the sink, naked save for a pair of black heels. Her 42Es hung under her and bouncing from the impact of the stud who was holding her at the waist, his thick throbbing cock pounding in and out of her horny MILF cunt. Shannon moaned at the sensation of being held in place and used in this manner, enjoyi...

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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Saving The Prince

by jessy19 on Sep 17, 2017
Celebrities & Fan Fiction

William was tired of it all. He felt trapped going from table to table and talking to boring, uptight people who only wanted to speak with him since he was a prince. Pretty rich girls dressed in beautiful designer dresses gathered around him giggling and batting their eyelashes trying to catch his attention. It wasn't unusual for him to be around classy rich...

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...