Hobo Stories

292 results
Orientation
Length
Source
Infinite Scroll

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 Letter to Dani Ch. 01

by laplappapillon on Sep 13, 2017
Letters & Transcripts

Do you remember the lake in Minorca, that lagoon on the coast north of Mahon? ...Es Grau I think it was named, where we had been promised we would see the sea-eagles. We walked up that gravel track in blazing sunshine and although it was really steep, it was an idyllic little journey. We were stopping every five minutes to take a photograph. There were tho...

Crystal Clear Ch. 22

by Romantic1 on Sep 11, 2017
Group Sex

This story is part of a stand-alone continuation of my Road Trip series (see the end of 'Road Trip – California' for a list of the chapters of that series, in the order to be read). You need not read that series to enjoy this series. Although real places and celebrity names are used for realism, this story is fiction. Please 'read, enjoy, vote, and comment.'...

Daddy Punishes Me

by ReneePfeiffer on Sep 12, 2017
BDSM

"How dare you fucking talk to me like that?" Daddy has me backed against the wall beside our bed. "Fucking bitch. You need to learn some gratitude and respect. I give you your perfect lifestyle and you wanna fucking leave me?" He's right. Daddy has always supported me and given me everything I want. Sex, drugs, a beautiful home, and his unconditional love,...

Gabrielle Ch. 01

by Sonreyes on Feb 12, 2019
Humor & Satire

Dating apps these days don't present a clear portrait of their users. From the moment I saw Gabrielle I knew she had to be different than the endless lists of fake girls that were in my area. With the face of Meg Ryan and the body of Sarah Jessica Parker and the ass of Chandler's hookup from Friends. I didn't think it could be true so I shot her message and...

Daddys New Toy

by need2nomyplayce on Sep 13, 2017
BDSM

I stepped off the plane, treading carefully down the metal ramp in my five inch black pumps, and starting searching through the crowd of people. Somewhere in that ocean of faces He stood waiting for me. I tugged at the hem of my black nylon dress, a little self conscious in its short length , knowing I was bare bottomed underneath it. I scanned the airport...

The Adventures of Sissy Madison Ch. 02

by sissymadison on Mar 6, 2018
Transsexuals & Crossdressers

They all got into Kim's car ready for the trip. Haley turned around as soon as Kim started the engine looking Madison up and down. "You are just sooo cute, I can't even get over it!" and with that Haley got out and hopped into the back seat with Madison. "So do you like being all dressed up like this?" Kent nodded but didn't say a word. "Oh don't be l...

Secrets, Fantasies, Lust, & Mischief Ch. 03

by ExotiqBeautii on Sep 14, 2017
Erotic Couplings

Hey guys. Sorry it's been So long. Hopefully this short excerpt will hold you over until I can really get into the story. Thanks for your continued support! -Ciao* * It had been about a week since I saw Felicia last. I guess she was pretty occupied with her man-friend. I hadn't gotten a good look at him yet; just a glance or two from a distance, so I don't...

Hauling Ass Ch. 01

by Maresy_Doats on Sep 12, 2017
BDSM

I drive a lot. I drive all over the state, and I'm never shy about seeing a new road or town. And it's not a small place. I was on one of my usual roadtrips, looking for new places and maybe a better job market, this time exploring northwestern bits I'd never been to before. I had a map, but I didn't usually use it. I didn't usually know where I was except...

Destroyed by text. Pt. 05

by Need_to_serve on May 11, 2020
BDSM

Wednesday: Pam 9:12am: 'Give me your landlord's contact details, hobo-trout.' John 9:13am: *Landlord contact sent to Pam* Pam 10:30am: 'Nice man your landlord. We have a lot in common; mainly in agreeing what a total fucking gutter mallet you are! LOL!' John 10:31am: 'Can I ask what you talked to my landlord about, please, Pam?' Pam 11:33am: 'I told him...