Patches
By LiciousRyan 20 May 2022
A vicar living in a small, rural village falls in love with a homeless beggar.
Gay Homeless Sex Stories
GayDemon's Stories: On this page you can find erotic fiction where you can read about meeting and having gay sex with homeless guys.
Street Love & Adventures
By Brent Boyco 15 May 2022
Last year I faced several months of homelessness. I failed to depair though, for I found love in the grungy shelters, took care of my body the whole time, discovered myself, and eventually found my way back home.
A Tale of a Homeless Homo
By Used&Abused 1 May 2022
A young gay guy becomes homeless and while in a camp gets used and abused by an older straight man.
Homeless John
By PPP343 20 Apr 2022
Met a homeless straight guy and fulfilled his wild foot fantasy
Picking up a Stray
By Disbtm 8 Feb 2022
Driving long distances can be lonely. Here's a tale of a driver picking up a little friend on a dark highway and teaching him how to be a good cock sucking sissy. Gas, Grass or Ass, nobody rides for free.
Homeless Bodyguard
By Stipa 22 Jan 2022
Sawyer founds Homeless man at his doorsteps and offers him a place to stay and more.
Crossdresser makes homeless man happy
By Paulacd 17 Jan 2022
I had gotten dressed very sexy and slutty one night being completely hairless permanently except for my eyebrows eyelashes and long hair on my head.
My Favorite Whore
By DarkDesires 30 Dec 2021
Meeting David behind the Big Box store turned out to be the best introduction I've ever had...
A shoulder to lean on
By Drew 3 Dec 2021
A marine falls on hard times and gets rescued by a queer.
Shelter from the Snow
By Habu 29 Nov 2021
Novelist picks up homeless guys in a Boston park.
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Blue Christmas
By Habu 20 Nov 2021
Fighting bad memories of a previous Christmas Eve.
Homeless guy gets lucky, so do I
By cbrguy 19 Sep 2021
I give a mature-aged but fit-looking hitch-hiker a lift in a country town. He has just become homeless and I have a spare room at home, so why not do the right thing and invite him to stay? Soon enough I get my reward.
Dedication Row
By J.W.G.L 23 Aug 2021
Chapter 1 - Ted was walking at the park looking for that homeless man, luckily he found him as soon as he saw him, he was crying. Will Ted approach him?
James Grady (ch. 14)
By Nyguy 2 Aug 2021
James opened the door. There was a tall dark-haired thin man with stubble wearing a dusty suit and shoes that were falling apart. “Good morning, I was wondering if you needed any odd jobs done around the house or maybe you need the lawn mowed” said the man.
Special Treatment (ch. 2)
By Zeen 29 Jul 2021
Out of sympathy, Alan takes in a homeless man going through hard times. Little would he realize that this would prove to be the best decision ever.
Degradation
By Todd Curry 30 Jun 2021
Drunken slut takes any nasty cock he can get
Jason and the Abandoned House
By DarkDesires 29 Jun 2021
I stumbled onto a homeless guy in an abandoned house and had some fun with him--whether he wanted to or not.
Bandstand
By Caliban 18 Jun 2021
A chance meeting with a homeless man develops into a hot incest threesome with his father…
And into the Fire
By Habu 31 May 2021
Homeless to rent-boy journey to escape family, crime.
The Homeless Guy
By Norm 9 May 2021
A guy who has lost his partner, and a homeless guy, in need of help, meet, have wicked, hot sex, and fall in love.
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Jogger's Dilemma
By Caliban 6 Mar 2021
A voyeuristic jogger accidentally falls into the clutches of a horny homeless duo…
A Homeless Treat
By Caliban 27 Jan 2021
A bisexual couple decides to be charitable when they invite a homeless guy for Thanksgiving…
Hot and Homeless
By Caliban 23 Dec 2020
Three hot and homeless men expand my sexual horizons…
The Tent Boys (ch. 13)
By Alex Ryder 10 Oct 2020
Jack and Lucas realize their strong feelings for one another. A threesome brings two of the boys closer together. A troubled Blaze has a last fling with a favorite trick. Lucas makes a new friend and possible has a new experience.
Taking a Hard Right
By RJC 30 Sep 2020
I didnt understand what I was doing.
The Tent Boys (ch. 12)
By Alex Ryder 24 Sep 2020
Jack and Lucas have a very special night together. Lucas comes out to Jack about his gender identity. He also realizes that he's more than just a boy to push around. Jack finds himself falling for a second boy in a week and makes a big promise to Lucas.
The Tent Boys (ch. 11)
By Alex Ryder 23 Sep 2020
Blaze hasn't had a night out in the clubs in a long time. He has been wanting to share the experience with Harrison. The two boys drop a couple of pills and have a wild night. They go home with a hot couple and make some new friends. Harrison has a night of firsts.
The Tent Boys (ch. 10)
By Alex Ryder 21 Sep 2020
As we learn in Lucas' backstory, life has not always been good to him. In fact, it has been absolutely terrible. After yet another disastrous night, Lucas meets a kind stranger who brings him back to his hotel. He'd meet his best friend through this encounter. Thinks seem to be looking better, for now.
The Tent Boys (ch. 9)
By Alex Ryder 20 Sep 2020
The backstory on Blaze. Blaze could have had a very privileged life. Unfortunately, his parents ruined that. He found his first true love, and he was taken from him. He turned to the streets and loneliness. He what might have been a second love, but lost him too. A gentle trick would turn out to be so much more.
The Tent Boys (ch. 7)
By Alex Ryder 17 Sep 2020
A bit of backstory on Harrison. He escapes his right wing parents and heads east. It doesn't always go well. Homelessness is tough. He loses everything and is taken advantage of. He gets close to getting into the worst trouble until he's saved by Blaze.
The Tent Boys (ch. 4)
By Alex Ryder 10 Sep 2020
Harrison feels like this thing with Jack will go places. He wants to share his newfound riches with the boys he considers his family - Blaze and Lucas. Lucas is ecstatic. Blaze is skeptical.
Certain Type of Man (ch. 3)
By wabuck 6 Sep 2020
This was a moment in my life I was, at first, not so proud of. Some guys I knew got together at a hotel and partied. We got drunk, and on a dare, I was told to seduce a homeless guy near the hotel (we could see him from our room) and bring him back him and suck his dick. He was a stocky black man, so I was definitely attracted to him. Afterwards I felt guilty about using his unfortunate situation,
The Tent Boys (ch. 2)
By Alex Ryder 3 Sep 2020
Jack slowly finds himself getting hooked on Harrison as Harrison finally gets closer to getting Jack in bed.
The Tent Boys
By Alex Ryder 1 Sep 2020
Harrison and his friends are homeless boys living in a tent city in Washington, DC. Life changes for the boys when they meet a generous billionaire who falls for Harrison.
Hard Times
By Slutty Texas Btm 27 Jul 2020
I agree to give a homeless young man a hair cut and next thing I know he's made me his bitch