Pimped Out Sissy Stories

353,644 results
Orientation
Length
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Infinite Scroll

Girl's Night Pt. 08

by DifferentBreed on Sep 14, 2017
Fetish

This a continuation from an earlier story. It contains fetish themes of forced feminization, public humiliation and other erotic themes that may not be to everyone's taste. If you enjoy these, please read on and leave comments as to how you'd like the story to evolve or what you like. Enjoy. - DB ***** After a short walk to the restaurant level Sophie excu...

Michelle Fucks An Intern

by Veri on Sep 19, 2017
Loving Wives

Michelle's problem at work was only getting worse. For months she had willingly allowed herself to be pimped out as a whore and walked the streets or worked in a bar while her pimped either collected her money or pimped her out to a gang member which then had her work for him for the weekend. This had gone on for a few months with no problems at her work at...

Dana - An Evening of Play

by thunderhead12 on Sep 17, 2017
Loving Wives

Yes - This story is true. My wife and I have talked about her servicing and being serviced by other men- especially blacks or Mexican men with dark Complexions. We once had a three- some with another guy. I also know she was in the game a few years ago (we were married about 15 years at the time) where she was enjoying a sexual relationship with a black guy...

Michelle Gets Pimped By Tony

by Veri on Sep 19, 2017
Loving Wives

(This is a continuation of the story of my wife becoming a whore.) Thursday morning my wife Michelle was up early for work. I saw her spending time in her closet examining outfits. In her hand she had a tube top that really didn't fit her. The word SLUT was across the front. This was one of the tops she wore when she became a whore on the weekends for the...

The Hot Milf Rachel Nichols

by DickThePimp on Feb 12, 2019
Celebrities & Fan Fiction

Freaky Rachel Nichols Fuck Parody I was looking out my bedroom window, in the late evening... doing some sightseeing with my binoculars... around the neighborhood for some action. It didn't take long, as I noticed my very sexy next door neighbor ESPN hottie Rachel Nichols. The beautiful read haired host of The Jump had just taken a shower and accidentally.....

After Bar 69

by Nudemodel on Sep 2, 2017
Interracial Love

"After Bar 69" is the second story in a series of four. It is drawn from experiences of a white American male nude art model, Tom, from Cleveland. He becomes a dirty naked sex-model publicly engaging in sex and rimming a naked black Jamaican female, Angela, in an open-to-the-public live-sex-peepshow on the Reeperbahn in Hamburg, Germany. Characters and place...

Shooting The Moon Ch. 02

by SEVERUSMAX on Sep 15, 2017
BDSM

Apparently, I fell asleep drunk and tired, which wasn't too surprising, given how much Jameson I drank the night before and how much I had fucked my three playthings. I didn't wake up alone, however. I was in my studio apartment, lying on the sofa, with Dana planting kisses on my cock and balls. Oh, yes, Dana ... the pizza girl, who had been so passionate an...

I am Number Four

by princessnocturne on Sep 18, 2017
Transsexuals & Crossdressers

I stood silently in the middle of my living room, surveying my very own new apartment with a weary satisfaction. I still had boxes of small stuff to unpack, dishes and books and the like, but the furniture and appliances were all in place, and the heavy lifting was more or less done. I felt a warm glow of pride as I saw it take place before my eyes, my first...

Mistress Treva Wins Again

by justincbenedict on May 29, 2018
BDSM

Dr. Shepherdson Grangerford milled about at the fundraiser, his adoring wife, Treva by him, the ultimate arm candy even after all these years. A balding, chubby fellow came up, grabbing Shep's hand. "Dr. Grangerford, everyone is so pleased that you made the fundraiser, and that you'll be heading up the Ophthalmological Wing. We probably couldn't have gotten...

Rosie Finally Meets Jessica

by DoesAnyNameWorkOnHere on Aug 6, 2019
Transgender & Crossdressers

It was cold. Bitter cold. January always brought negative temperatures and more snow than I care to see. It's the kind of cold that gets into your bones and you can feel it for hours after being in a warm place. Not even a hot shower can soothe the chill you have inside. Short days and long nights made the month long and depressing. My only respite from the...