Pimped Out Sissy Stories

353,644 results
Orientation
Length
Source
Infinite Scroll

Anklet Adventure Pt. 02

by dometoo on Oct 29, 2018
Interracial Love

Day two of our cruise started with the sun shining through the open balcony slider and a slight, warm breeze dancing over our naked bodies. The rhythmic sound of waves breaking against the hull was memorizing, almost hypnotic. My beautiful wife of 20 years and I lay exhausted on the cum stained sheets she and her bull made without me last night. We were both...

How it All Began for Us

by flashgordon562006 on Mar 11, 2019
Erotic Couplings

I just about opened my eyes when I noticed that my husband of thirty plus years was naked and had his arms all over a woman I barely recognized. Then, I opened my eyes wider and looked around and saw naked bodies all over. I looked at myself and saw I was covered in cum and a guy nestled against my naked body. I then somewhat remembered what happened. And,...

An Emily Story: Mom Pimped

by B5040905 on May 13, 2020
Loving Wives

The next part of Emily's Mom Story I thought I had found an editor but I have not heard back from them after sending this story to them. I assume it means the story is terrible but I am posting it anyway. Janet's phone vibrated in her pocket. She looked at the text. "The Hilton downtown. Room 1203 9 PM. Dress like the slut you are." The text sent a chill...

My White Trash Life Motherfucker Ch. 01

by DickThePimp on Jan 15, 2019
Celebrities & Fan Fiction

Fucked up fuck parody series alert WARNING : The most offensive and depraved fuck parody series ever written... Read at your own risk... If you're not offended then you're one of my fans motherfucker... I approved this fucking message... Read on motherfuckers... This series replaces the White Trash For Life series... Pussy + Moonshine = Life... FUCK YEA...

Money Shot Pt. 02

by GavinIsaNuisance on Jul 27, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and completely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Tanya introduces a newly sissified Danny into the world of erotic photography which gets them into a hot offer they can't refuse. Author's Note: So, I establ...

Pimpin' ESPN Ch. 02

by DickThePimp on Oct 30, 2018
Celebrities & Fan Fiction

This is a sleazy ass fucktastic sex parody series... It ain't real Star of this story : Sarah Spain "Sarah, I have big plans for you. I wanna make you the FACE Of ESPN. You're exactly the face I want all over my network... and the rest of you as well." "Well, thank you James. I appreciate that and I appreciate the confidence you have in me as well. I prom...

Laurie's a Good Girl

by ElGreco on Mar 25, 2018
Cheating Spouses

Laurie was a cute young lady. You wouldn't call her "sexy", or "hot". AAlthough she had D-cup breasts, a curvy figure, and a round backside, her demeanour was far too sweet. Her smile was warm and charming rather than sultry; her wardrobe favoured cardigans and trainers rather than short skirts and high heels. She was pretty, friendly and...

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Dick the Motherfucking Pimp

by DickThePimp on Aug 1, 2018
Celebrities & Fan Fiction

This is a parody... It is not real *** This is my story, sort of. It's a small example, of who I am. I came along and took the sex story world by storm, with my freaky, in your face, stories and swagg. I was invited to be on Ellen the other day. I decided if I was gonna do it, then I was gonna do it big pimpin' style. I was gonna show Ellen DeGeneres exact...

Pimpin' Jersey Shore Ch. 03

by DickThePimp on Nov 20, 2018
Celebrities & Fan Fiction

THIS IS A PIMPED OUT FUCK PARODY SERIES... IT AIN'T REAL It was the last day of my Jersey Shore vacation. The weather was great, 80 degrees and sunny. I was on the deck of my rental place, relaxing with my girl, Jwoww. She was topless sunbathing, a hot pink thong on and nothing else, except designer shades. She had her right hand in my swim trunks, slowly.....

Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...