Streetwalker Stories

352 results
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Tips for the New Streetwalker

by Martika_Duponte on Sep 1, 2017
How To

Hi, allow me to introduce myself. My name's Martika. I'm 30 and I'm a 3rd generation prostitute and I've been so for the last 16 years. I've always worked the streets, never even bothering to think about any other form of prostitution. Streetwalking is the one for me! So I know my shit, right? Right! So let's get on with it! Attitude ; attitude is ever...

Courtney Love Streetwalker

by DickThePimp on Jul 25, 2018
Celebrities & Fan Fiction

THIS IS A PARODY... IT IS NOT REAL This is my new series about famous women giving in to their deepest, darkest sexual urges and becoming prostitutes... First up is Courtney Love... Enjoy *** Courtney Love had decided she wanted to become a streetwalker, because her acting and music career had hit a snag and mostly because she craved dirty, cheap sex. She...

Fun with the Boss

by CAExhibitionist on Sep 15, 2017
Exhibitionist & Voyeur

As agreed, I wore a sheer blouse, jacket, and short skirt with fishnet hose and garter belt, but no bra or underwear, not even a G-string. Sleeping with the boss isn't as bad as I'd thought. It turns out he's a kinky bastard. And of course, my unwarranted promotions sure help things along. Tonight he's taking me to dinner at my favorite, swanky -- and very e...

Stephanie McMahon The Streetwalker

by DickThePimp on Jun 4, 2019
Celebrities & Fan Fiction

SEX FICTION... NOT REAL I was sitting in the WWE Headquarters office of the one and only Stephanie McMahon. She and I know each other very well. We used to go out. We've shared some fun memories over the years. Stephanie walked in and greeted me, hugging me, kissing me on the cheek. "James... long time no see. How have you been dear?" "Great. You're looki...

Chelsea Handler Streetwalker

by DickThePimp on Aug 21, 2018
Celebrities & Fan Fiction

This is a parody... It is not real Chelsea Handler had been a slut for awhile. She has blown producers and comics, anyone that could help her career. She has always enjoyed using her body for her career, so it always made her cum real hard. She has a great body she's tall, has nice legs, a nice ass and great tits. She loves showing her tits. She's always po...

Valerie in New York Ch. 01

by gunhilltrain on Jan 15, 2019
Celebrities & Fan Fiction

[A number of years ago I became interested in the movie I Shot Andy Warhol mainly because of Lili Taylor's performance as Valerie Solanas. Although I was impressed by her work, I thought Taylor fell somewhat out of character at times and made Solanas appear more personable than she likely was in reality. Anyway, I thought that the movie needed more detail a...

Bank Teller Turned Hooker Ch. 18

by SweetTastnNess on Mar 9, 2020
Group Sex

Chapter 18 - RICE-A-RONI IS NOT THE ONLY SAN FRANCISCO TREAT (NOTE TO READER: One of my followers suggested that I might start this chapter with a comment about my story. As many have surmised, this is not a story of fiction. My writing reflects real events in my life. As described to one reader, "As written, the timeline is probably 90% accurate; the dialo...

Kayla and Tracy: Change of Pace

by BrettLynn on Sep 16, 2017
Transsexuals & Crossdressers

Hey, after being inspired by some fan mail, I decided to toss this story together on a lazy holiday Saturday. Let me know if you want me to write more. Heck, let me know if you want to take something on, so long as you don't add any transsexual on male sex. On that note, let's get to it. * She twitched in her seat as she rode along in her limo, her long,...

Stopover in Peoria

by luciarochester on Sep 14, 2017
Erotic Couplings

Randy drove slowly through the red light district of Peoria. Work had brought him to Peoria, but his lust drove him to the decaying west end of the town. He had been through this town many times, driven down the gritty streets, watching as half naked women, some young and others not so young walked the sidewalks, waving and smiling at him through the car win...

Penny's Worth Ch. 05

by Krystal0690 on Sep 19, 2017
Loving Wives

Parts per Million The surfer carried his board onto the beach and buried its tail into the soft sand so that it stood upright. I was thankful that he was in the process of putting on a pair of long shorts as I approached. That would make our introductions less awkward. "Hi, my name's Stella. I wanted to ask you something." I smiled pleasantly and used a sw...