Sissy Pimp Stories

9,288 results
Orientation
Length
Source
Infinite Scroll

Pimpin' The Tweeds

by DickThePimp on Sep 4, 2018
Celebrities & Fan Fiction

This is a parody. I was kicked back, after an all morning fuck fest with my girl, Kim Kardashian. My cock was pleasantly sore and well pleased. My phone rang. It was an old friend of mine, Shannon Tweed Simmons. We used to fool around, back in the day, but I haven't seen her in a couple of years. She asked me to come over. I told her I was tired, but she in...

All Women are Bitches Ch. 16

by Samuelx on Sep 14, 2017
BDSM

Oh, my frigging Gawd! My ass is full! Currently, I'm on all fours, my big black plump butt cheeks spread wide open. Drilling his twelve-inch uncut black super cock into my tight asshole is my main man Trevor. The roughest, meanest black pimp this side of Detroit. Every time he slams his cock into my shit hole, I feel like I am frigging dying. And I totally l...

Pimping My Ride

by Twotooto222 on Nov 8, 2017
Loving Wives

My hot wife Brandi, 40, 5'8" with killer 36D silicone tits, long toned legs and an all over tan, and I went to Vegas recently to party, gamble and some swinging. We spent the afternoon at one of the casino's topless pools and Brandi had the attention of most the men there who'd walk by slowly checking her out trying not to be too conspicuous. I'd send her to...

My Wife Takes a Pimp Ch. 02

by Veri on Sep 12, 2017
Loving Wives

This is a prequel to the story where my wife gets a pimp. It documents the fantasy play that my wife and I engaged in as she moved closer and closer to her ultimate fantasy of being a street whore. I was sitting in my car watching my wife walk down the street swaying her ass from side to side. She was wearing a pair of ripped jeans shorts that were two siz...

How The Inch Stole XXXmas

by SanchoHardbottle on Feb 6, 2018
Humor & Satire

Every Fuck Down in Fucksville Liked XXXmas a lot... But the Inch ,Who lived just north of Fucksville, Did NOT! The Inch hated XXXmas! The whole XXXmas season! Now, please don't ask why. No one quite knows the reason. It could be that his testicles were hung up far too high. It could be, perhaps, that his bladder was shy. But I think that the most likel...

Club 18-22

by abroadsword on Sep 17, 2017
First Time

All characters are over 18. "Ola, hello, welcome to club 18 -22, I am Miguel and I am your pimp for the week," the sun bronzed Spaniard announced as he walked into the girl's room. Sandra laughed drunkenly and said, "Oh right, Pimp eh, maybe your English isn't too brilliant?" "Pimp, he said Sand!" Irene replied equally drunkenly, "Because if he's our...

Driving Miss Rousey

by DickThePimp on Sep 18, 2018
Celebrities & Fan Fiction

This is a fuck parody... It ain't real. "How long have you been driving celebrities?" "About a year. It's a part time diversion for me." "Diversion from what?" "Life in general... No, just kidding, from my other job." "What's your other job?" "I'm a pimp." "You're kidding." "Nope. Pimpin' ain't easy ma'am." "Ha. I'm sure. Call me Ronda. I like you J...

The Adventures of Astoria Morgan Ch. 02

by Longo_Afar on Oct 16, 2018
BDSM

Chapter 2 - Little Bird Sings Pudenda Minks looked down at the young woman tied to the chair in the center of the room. Naked and trembling, just the way she liked them. A lamp hanging low from the ceiling threw a merciless light that made the sweat on the captive's forehead glisten and her red curly hair glow with an almost bloody hue. Bloody but not brok...

Modern Fairy Tales Ch. 13

by Boxlicker101 on Sep 11, 2017
Chain Stories

They weren't really little and they weren't really pigs; they were just called that by way of being disrespected by their pimp. Actually, they were all beautiful young black women and classmates, who had been working as prostitutes to pay their way through college. To keep the cops or other pimps from hassling them, they signed on as members of the stable of...

Pimpin' Jersey Shore

by DickThePimp on Aug 7, 2018
Celebrities & Fan Fiction

This is a parody... It is not real *** I decided to take a vacation from my pimp work. I headed down to the Jersey Shore. I hadn't been there in awhile and I heard they had some hot pussy down there nowadays, so what the hell, I decided to check it out. I ended up in a nice house, right behind the house from Jersey Shore, that MTV show. Nobody was in it, s...