Pimped Out Sissy Stories

353,644 results
Orientation
Length
Source
Infinite Scroll

Wife Gets a Pimp Ch. 02

by MrsCanyon on Sep 14, 2017
Group Sex

As I stood up in front of Tony, I said, "Remember how I got Tracy fucking you guys to get us out of debt? Well you're in debt, you could be her pimp, and she could fuck for you!" Tony's statement was, "Are you serious? Me, her pimp!" I reassured him that I was serious and that I know that he could get a lot of his friends as clients to fuck my wife. I rem...

Laura, Steve and Me

by murphy621 on Sep 17, 2017
Loving Wives

I first noticed them on the dance floor. They were a handsome couple, who appeared to be about my age. They danced well together; they must have known each other for a long time. The reason I noticed them was not because they were good looking, it was because they seemed to be checking me out. As they rotated during the slow dance, the one facing me would s...

Hazardous Waste Ch. 05

by NOIRTRASH on Sep 16, 2017
Loving Wives

All characters are adults. Reminder. This tale is noire, and noire is neither kind nor gentle nor uplifting. It's supposed to stun and sting and offend. ***** I got sick as shit one night so they tied my sixty-five year old ass up in a straight jacket and hockey mask, like I was Hannibal fucking Lector, and led me off to the infirmary with an armed escort...

Truthful Ted

by AtFirstSight on Sep 15, 2017
Humor & Satire

Before I can tell you the story of Jerry, I have to tell the story of Ted. You'll understand when you're older. (Seriously, when you're a few weeks older and I submit the Jerry story, you'll know why I introduced Ted first.) Ted's reputation among my friends is incredibly divisive. One of my friends will burst out laughing and shout, "Yesssss! Big Dick Ted!...

Pimpin' the Women of WWE Ch. 03

by DickThePimp on Nov 5, 2018
Celebrities & Fan Fiction

THIS IS A SLEAZY ASS PIMP FUCK PARODY... IT AIN'T REAL Stars Of This Story : Nia Jax Sunny Sable Stephanie McMahon (My Wife) Alia Janine (My Girlfriend) Beverly Hills Hotel... Beverly Hills, CA. "Good Nia... great pose... kiss at the camera sweetie." "Make sure you get every angle Spence. Nia looks beautiful... I wanna capture her beauty from every...

Senatorial Secrets Ch. 05

by RedHairedandFriendly on Sep 14, 2017
Loving Wives

Taken from Ch. 04 ". . .I am currently between lovers," she answered and made sure no one but her husband heard her. She laughed for the crowd and stuck out her tongue in hopes all thought her dashing love had teased her unmercifully. His brow rose and he smirked. "Then may I steer you toward one?" he chuckled at her low throaty growl of "bastard." "I...

The Sleaziest Agent Ch. 01

by DickThePimp on Dec 11, 2018
Celebrities & Fan Fiction

This is a porn parody... It's a fantasy only... It ain't real This is a two part story based in 2012 and stars Chyna aka Joanie Laurier... R. I. P. "Yeah... that's right Steve. You get me 4 tickets to Madonna's LA show and I'll hook you up with Christy Canyon. You scratch my back... I'll send you some big titty whores." Christy smacked me as I fucked her...

Sandy's 30th Birthday

by PamR55 on Aug 17, 2017
Exhibitionist & Voyeur

For my wife's 30th birthday I surprised her with a suite at the Drake Hotel overlooking Michigan Avenue and dinner at a snooty downtown restaurant. I also bought her an obscenely short red dress that looked painted on her. Underneath she wore the rest of her present, a black shelf bra that gave her incredible cleavage and a pair of crotchless, black, backsea...

My New Job Ch. 02

by Deeplust on Aug 5, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** *I know there are plenty of mistakes, but I am moving to another story for awhile and will not come back to this one for awhile.* ***** I followed Jeri down to the room she used before and I saw that she had the bed made. I instantly saw multiple bottles of lube from the cabinet...

Spring Fever: Decisions

by wudelfin on Sep 16, 2017
NonHuman

The words on the page have blended together for the past twenty minutes. Sighing in defeat Junediai leans back. Details of the new Master's trail will have to wait until she can think straight. Gathering the report with a stack of other unread papers she locks them away in her desk drawer. Rubbing her eyes with the heel of her palms she tries to relax. The i...