Pimp And His Boys Stories

369,102 results
Orientation
Length
Source
Infinite Scroll

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...

My Wife Takes a Pimp

by Veri on Sep 19, 2017
Loving Wives

My wife is 40 year old executive at a major corporation. She is in a high powered field and earns a great income. She also has had an overwhelming fantasy to be a whore to a black pimp. During our love making we would tell each other fantasies. That led to me buying her hooker outfits, which led to me videoing her walking down the street pretending to look f...

Michelle Gets Ready To Go Out Again

by Veri on Sep 17, 2017
Loving Wives

After Michelle got home she slept for several hours. Her body had some bruises on it, noticeably around her breasts where her customers had marked her large breasts with bite marks and bruises. A few hours after she was home her phone started to ring with voice and text messages. First was from her pimp telling her to call. Then the guy she had met who want...

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...

My Wife Becomes Whore to a Gang

by Veri on Sep 26, 2017
Loving Wives

My wife Michelle is a high powered lawyer in our town, which is a medium sized Midwestern city. We've been married for about 22 years. About 3 years ago we were in a bit of a doldrums and I decided to spice things up by renting a room at a sex motel in the seedier side of town. The motel was one with themed rooms and Jacuzzis. To my surprise Michelle dressed...

Meagan's Story Ch. 05

by TX_Fun_Dr on Sep 19, 2017
Interracial Love

All characters are at least 18 years of age Chapter 5 – We made over $11000 in one weekend – Wanna make even more!!! OR – How I Sweet Talked My Big Black Daddy Into Being My Pimp As the alarm went off at 6:00am Marcus heard the shower running. Meagan was already up and in the shower. Laughing he thought to himself – Yeah she had a major clean up job to...

Pimping Angel

by Angelscuck on Sep 16, 2017
First Time

"Oh, here's something interesting," my fiancée Angel said, browsing through the throw away paper calendar. "A local strip joint is having a Pimp 'N Ho Party Saturday night. Bikini dancers, good food, music and live entertainment and customers are encouraged to dress up as pimps and whores. Sounds like our kind of party, interested?" "Sure, why not?" I repli...

The Making of Davina Ch. 02

by Timewarp10 on Nov 20, 2018
Transgender & Crossdressers

David put make up on, and looking in the mirror he liked what he saw. It was as if he saw himself for the first time; a person within being born. Davina came to life. "Oh God! It feels so right!" David remarked, seeing Davina smiling back with Davina's eyes, and not David's. He was looking through a portal into his own true soul, and he wanted to step into...

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...

Yin-Yang 02: The Return of Jack Daniels

by Skippy47 on Oct 5, 2020
Non-Erotic

THE RETURN OF JACK DANIELS Author's note: This is a sequel to Yin-Yang, a short, weird tale. You probably would enjoy this one better if you read it first. I had a hard time and many drafts before I came up with this. Hope you enjoy. The end of Yin-Yang: Jack was vacationing after he had killed a mother and son who had used Jack to steal the inheritance fr...