GayDemon's Stories: On this page you can find erotic fiction where you can read about meeting and having gay sex with homeless guys listed by date.
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.
Topics: Anal Sex, Crossdressing, Forced, Daddy, Sissy, Hitchhiking, Virgin, Homeless, Slave Training, Fucking
Sawyer founds Homeless man at his doorsteps and offers him a place to stay and more.
Topics: Romance, Homeless, Love
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.
Topics: Crossdressing, Daddy, Homeless, True Story
Meeting David behind the Big Box store turned out to be the best introduction I've ever had...
Topics: Anal Sex, Prostitution, Oral & Blowjobs, Homeless, Gay for Pay
A marine falls on hard times and gets rescued by a queer.
Topics: Anal Sex, Straight Men, Homeless, Marine
Novelist picks up homeless guys in a Boston park.
Topics: Fiction, Sex, Homeless, Age Difference, Hookups & Dates, Sixty Nine
Fighting bad memories of a previous Christmas Eve.
Topics: Big Dick, Voyeurism, Romance, Relationship, Interracial, Homeless, Christmas, Loneliness
Joe finds himself in a different city under trying circumstances, but a sudden incident changes the course of his life again.
Topics: Fiction, Prostitution, Homeless, Houseboy
The story of a runaway boy in Britain in the '90's. In the final part (for now) the boy, Jack, says goodbye to Nick and learns the ropes in his new job. But why does he feel this way when James looks at him? And should he take part in Nat's organised sex activities.....?
Topics: Romance, Friends, Bisexual, Twink, Sex, Homeless, Love
The story of a runaway boy in Britain in the '90's. In Part 4 the boy is interviewed for a job with Nick's old friend, Nat. Everything seem almost too good to be true. There's another boy working here, too. A beautiful boy called James. When James shows the boy to his room, there's more to see than just furniture!
Topics: Romance, Friends, Stripping, Twink, Sex, Homeless, Love
The story of a runaway boy in Britain in the '90's. In Part 2 the deal with Nick is strained. Can the boy and Nick work something out, or will Nick's tendency to use the boy for his own ends stretch this odd relationship to breaking point? Either way, something has to change.
Topics: Anal Sex, Forced, Daddy, Twink, Homeless, Age Difference, Rentboy
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.
Topics: Piss, Anal Sex, Hitchhiking, Bareback, Oral & Blowjobs, Homeless, Kissing
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?
Topics: Muscle, Hairy men, Romance, Daddy, Relationship, Bear, Homeless, Stranger
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.
Topics: Straight Men, Big Dick, Historical, Twink, Homeless
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.
Topics: Fiction, Romance, Sex, Homeless
Drunken slut takes any nasty cock he can get
Topics: Piss, Anal Sex, Dildo, Bareback, Drunk, Homeless, Degradation, Anonymous
I stumbled onto a homeless guy in an abandoned house and had some fun with him--whether he wanted to or not.
Topics: Asian Men, Anal Sex, Forced, Homeless, True Story, Fucking
A chance meeting with a homeless man develops into a hot incest threesome with his father…
Topics: Anal Sex, Big Dick, Threesome, Incest, Oral & Blowjobs, Homeless
Homeless to rent-boy journey to escape family, crime.
Topics: Rough Sex, Bondage, Prostitution, Interracial, Mystery & Crime, Homeless, Age Difference, Gangbang, Rentboy
A guy who has lost his partner, and a homeless guy, in need of help, meet, have wicked, hot sex, and fall in love.
Topics: Anal Sex, Rimming, Romance, Homeless, Nipple Play, Fucking
A voyeuristic jogger accidentally falls into the clutches of a horny homeless duo…
Topics: Anal Sex, Rough Sex, Group Sex, Voyeurism, Coercion, Oral & Blowjobs, Homeless
A bisexual couple decides to be charitable when they invite a homeless guy for Thanksgiving…
Topics: Anal Sex, Group Sex, Bisexual, Oral & Blowjobs, Homeless
Three hot and homeless men expand my sexual horizons…
Topics: Piss, Anal Sex, Rough Sex, Gloryhole, Oral & Blowjobs, Homeless
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.
Topics: Rough Sex, Threesome, Hotels, Twink, Virgin, Oral & Blowjobs, Sex, Homeless, Ass Play, Fucking, Throat Fucking, Depression
I didnt understand what I was doing.
Topics: Fiction, Big Dick, Sex, Homeless
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.
Topics: Romance, Transgender, Feet, Homeless, Age Difference, Kissing, Fucking, Love
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.
Topics: Dildo, Fisting, Feet, Drugs, Twink, Homeless, Fucking
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.
Topics: Prostitution, Friends, Shower, Twink, Homeless
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.
Topics: Voyeurism, Romance, Prostitution, Twink, Homeless, Love
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.
Topics: Fiction, Twink, Homeless