Sissy Pimp Stories

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Discovering Mistress Sarah's World Pt. 07

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

CHAPTER 18 A Life Changing Decision Sunday morning was not much different than the day before for Josie. He woke-up on the floor outside Mistress Sarah's bedroom, dressed in a silk night-gown and his cock was hard and aroused when he awoke. Just like Saturday morning, he crawled into the bedroom. Mistress Sarah was waiting for him. She was lying on her side...

Black Man's White Sissy

by nancyvasquez on Sep 18, 2017
Transsexuals & Crossdressers

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince...

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...

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...

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...

Whore for Black Cock

by the_harmless on Sep 12, 2017
Interracial Love

Dear Paul, I wanted to write you to catch you up on my latest adventures. I know you're always eager for details, and I have some for this month I which I think you will enjoy reading about. Be sure and get somewhere private when you read this because you are going to be hot under the collar (among other places) with what I have to write! Only a few close...

iWhore

by FellatiaViper on Sep 15, 2017
Transsexuals & Crossdressers

Chapter 1 The dimly lit room brightens in flashes of red and blue from outside the window as the sluttily dressed transwoman kneels over the body of her victim, crying, after she just slit his throat open from ear to ear, and still stroking his deflated penis as the door to the apartment is kicked in and the police rush into the room. "Freeze! Drop your we...

My Mother's Boss Pt. 03

by phoenixcinders on Jan 20, 2020
Transgender & Crossdressers

Hey everyone! Here's part 3. All characters engaged in sexual activity are above the age of consent. Also, because someone decided to copy my stories and publish them online, I would like to remind everyone my stories and characters are protected under copyright law. Now read on and tell me what you think in the comment section below. Feel free to reach out...

Anklet Adventure Pt. 04

by dometoo on Nov 27, 2018
Interracial Love

Editor's note: this story contains scenes of incest or incest content. *** The last time Lynda and I returned from our romantic getaway cruise, she came back black bred and knocked up, cuckolding me and keeping me in chastity much of the time. I'm now the proud father of a three-month-old black boy, Mark, her bull's namesake; with strong prospects of havin...

Whore Today, Gone Tomorrow

by Hobbes Goblynn on Sep 14, 2017
Humor & Satire

One day Eric the Weenie was coming back from a NASTY (National Association of Saddened and Tampered Youths) meeting when he saw a whorehouse. Eric wasn't the prettiest apple in the tree, so he doesn't get laid a lot. He's so Ugly, the only girls whoever look at Eric are bulimics because he makes vomiting more easy. Since he was right at a whorehouse and feel...