Homeless Man Stories

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Homeless Man In My Locker Room

by Phallux on Sep 12, 2017
Erotic Couplings

It's the start of another school year at Goodyear High School for me after a long summer of waitressing at the local ice cream shop. I've always wanted to be a cheerleader, ever since I was about 5 and went to my first football game in town and saw all the beautifully dressed girls doing acrobatics and waving their pomp-pons. My mom promised me, "One day, Na...

A Homeless Man

by Beejayne on Sep 19, 2017
Group Sex

Diana and Dave had only been in London a few days and were over the jet lag they both usually suffered from. They were staying with Al and Brad a gay couple who lived in Northwest London. Al was a friend of Jim, Dave's brother, who drove a minicab in London. Al had taken them across the street to a small private club where they had a nice meal and too much...

The Homeless Man

by Grey Eagle 286 on Sep 17, 2017
Loving Wives

The men sat on a park bench. One was a small older man. His companion was about thirty five or so but it was difficult to accurately tell his age. His eyes were unfocused and blank. It was clear he had not bathed or changed clothing for a long time. His clothes were in rags and were filthy. His hair and beard were matted with filth and debris. The older ma...

Inspiring the Muse

by tinybabelost on Aug 21, 2018
BDSM

The homeless man trying to nap on the platform gave her a curious look when she failed to get on the third consecutive train that passed by. She stood back against the wall, out of the rush of commuters trying not to look anxious, like she was waiting for someone. She held a trade paperback loosely in her hands and tried to concentrate on draining her face o...

A Favor for the Homeless Man

by Sugarrushwerewolf on Oct 24, 2018
Fetish

A husband and wife were eating at a Restaurant late one night when they were greeted by an older gentleman who happened to be homeless. Out of courtesy they allowed him to sit and talk with them. The man talked about all he places he had visited being homeless and how he lived alone and traveled alone. A wicked idea crossed the husbands mind and he decided t...

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...

Old Man Fetish

by CumalotCastle on Sep 11, 2017
Mature

I'm your typical 19-year-old girl. Just finished college, started my first job. I like to socialise. I like to buy new clothes and read girly magazines. I'm medium height, dark hair, blue eyes. My body has developed well and I have fairy big C cup breasts and a nice pert ass. I keep my pussy trimmed and I go to the gym a couple of times a week. Other than al...

The Man Who Fucked His Way Across... Ch. 02

by Hugopossetposset on Sep 2, 2017
Fetish

The Man Who Fucked His Way across Chelsea and Back Again - Part 2 INTERVIEW I was invited to see the head designer, Liza Blow at Vagina Shoes after a successful phone call. I forwarded some of my friend's best sketches by email and she phoned me back a few weeks later. Jefferson, who let me borrow one of his portfolios, was a Cordwainer's graduate and spec...

Homeless Heart

by sr71plt on Sep 14, 2017
Erotic Couplings

Almost. Getting there. This time. Oh, dear god, have him take me . . . there . . . this time! Panting hard, rubbing her clit to beat the band, concentrating on him moving inside her, she began to emit little yipping sounds. Tightening up, just . . . about . . . And then Kurt jerked and shuddered and rolled off to the side and stared up at the ceiling. "I ....

Abandoned Building Homeless Voyeur

by urbanslut on Sep 15, 2017
Exhibitionist & Voyeur

Note - This is a slightly different story from my usual ones. Narrates in the third person but from individual perspectives. And low on wham-bam action. HIM He groaned at the pain in his arms as he gingerly climbed over the barbed wire fence, careful to avoid getting pricked again. The last time he tried to climb it, one of the spikes had cut his thigh an...