Sissy Pimp Stories

9,288 results
Orientation
Length
Source
Infinite Scroll

Freak Daddy

by DickThePimp on Jul 6, 2020
Celebrities & Fan Fiction

Keeping it simple... And freaky... Parody... Offensive, but fun... For perverted entertainment purposes only... It's fuck time, bitches... You ever freak a bitch while your sweet mama makes you breakfast? I did just now. My girl Rosario Dawson strolled her fine Puerto Rican ass into the kitchen all nude and shit... Except for her gold and diamonds FREAK ch...

Michelle Goes Out And Gets Pimped

by Veri on Sep 16, 2017
Loving Wives

My wife Michelle was getting dressed and she had that look in her eye. It was a Thursday night and she had worked hard all week in her law firm where she was a partner. However as she got dressed, this was not her conservative persona. She put on a pair of way too tight jean shorts and some five inch red heels. When she walked her ass cheeks hung out and sho...

A Very Hard Working Girl

by keptsissy on Sep 12, 2017
Transsexuals & Crossdressers

I jump around a lot when I tell my story. I don't always tell it in the order that it happened. But I do tell my story accurately. It's all me. I write from experience, love to share the dirty little kinky things I do. There is no moral to the story, no ending. I just like to write about the things I've done and continue to do. And I love to think back and r...

Babette in K-Town

by Babette_Boisjoli on Sep 16, 2017
Transsexuals & Crossdressers

I'm in an alley, on the west side of Chicago. There is no mattress or anything, but I have a towel to kneel on. My pimp is lining up men. They are lining up to fuck my face. They are looking at me, drinking, smoking, laughing. I can overhear comments about this "fuckin white ho" and "them nice big titties". They are right. I do look like a fucking whore. I...

Ms. Dollie's Random Stories Ch. 15

by LIVINRFANTASIES on Sep 15, 2017
Exhibitionist & Voyeur

ADULT CLOTHING SHOPS OF THE FLORIDA KEYS Let me apologize for adding things here which are not exactly dress-up surprise games. However, they were games, Dollie and many people got surprises. This counts!! Here I am, again jumping forward, this time to 2004. It was our long Florida Keys Summer getaway. So many fun kinky adventures during more than two mont...

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...

Jack's Women

by LustinTranslation on Sep 11, 2017
Novels and Novellas

This is my first attempt at submitting a piece of my work. If this is received well, I'll add more. This story is a total work of fiction, it never happened and the people do not exist. I hope you enjoy. Jack's Women Chapter 1 He sat in the alleyway, drinking from a bottle of Jack, pissed and tired of all the bullshit in his life. All he wanted was so...

Fuck You TV Ch. 04

by DickThePimp on Jan 21, 2020
Celebrities & Fan Fiction

"So... Megyn... what do you think about my idea to spice things up around here?" "What about you Gretchen?" "Uh huh... and you Katie?" I'm leaning back in my very comfy office chair, asking my three main ladies Gere at the Network how they feel about my idea of having a fan raffle each day, so a lucky fan can come up to Fuck You TV and fuck their favorite...

Evening Class

by Winterfrog on Sep 12, 2017
Loving Wives

Many thanks to Dennis for his editing of this story. * It began in a very unexpected way, I got a small folder about evening classes in my mailbox and found out that some further education in Spanish would be fine because the Spanish islands are very popular tourist spots for us in the Scandinavian countries. Decision followed by action and two weeks later...

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...