Pimped Out Sissy Stories

353,644 results
Orientation
Length
Source
Infinite Scroll

Can't Say No Ch. 01

by MobeyDick on Feb 11, 2019
Loving Wives

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Chapter 1 - Skipping Class Cathy Successfully Resists Her Boss, In A Series of Completely Unavoidable Accidents. Cathy walked into my at-home office, after coming home from what we had both assumed would be a day of continuing education training. Her hair was mussed and d...

Traci's Earring

by johnson69 on Feb 26, 2019
Transgender & Crossdressers

I found Traci's pierced earring on the floorboard of my car when I got in it this morning. It was a small dangling silver ankh with turquoise inlay centered in the line of the cross throughout the shape. The sight of this icon, the crux ansata, flooded my head and body with memories of the past evening and early morning. The little cross moved feelings in my...

Behind the Scene

by psiberzerker on Aug 1, 2018
BDSM

The Elephant (FFFM Bond Toys) They didn't talk about me. Not even as if I wasn't there, they looked, and smiled, then went back to their conversation. The Bechdel Test. I guess, but my girlfriend isn't a lesbian. She's an "entreporneur." Her little joke, but we saw a niche, and figured out how to exploit it. "See, the problem with Buying sex toys," more th...

I had to Find Out

by blondsubles on Sep 26, 2017
First Time

This weekend would be the perfect time to find out too. It was my last three days in Vegas. The convention that I was in town for had been educational but rather dry and I was ready to go back home to Mississippi. It wasn't like I was cheating on anybody anyway. I hadn't been in a serious relationship in over a year. That isn't to say that I hadn't had sex....

A Second Night

by Phased13 on Sep 2, 2017
Fetish

The key card slipped through the door reader and we heard the click of the lock disengaging. I turned the handle and we walked into the room, tossing our coats into the closet. I quickly take off my shirt and sit down on the bed to unlace my shoes as you take your shoes off beside me, setting the bag next to the bed. We both sit up, look into each others eye...

My Fantasy Island: Jessica & Sarah

by willielongfollow on Sep 14, 2017
Celebrities & Fan Fiction

Two of the most stunning actresses in my opinion to ever come out of Hollywood were arriving at my Island. I just can't wait to make their wishes come true. As they walked up the dock, my cock got instantly hard, looking at them they were stunning, no beautiful, Jessica was wearing a white strapless tight fitting mini dress, Sarah's was wearing the same thi...

Beyond Boundaries

by subnonnie on Sep 17, 2017
BDSM

When we first met, i had no idea where the relationship would take me. We got along very well, and our sex life was fantastic. We had few boundaries in bed, but the one that frustrated my boyfriend the most was that i refused to any anal penetration. No fingers, no toys, and especially no cock. We started experimenting with submission about six months ago,...

The Wallflower Ch. 02

by BlessingAndCurse on Sep 25, 2017
Erotic Horror

/// I thank everyone for the support. I would really love for more criticism for this chapter. Write me in the comments what I can work on in the next chapter and even tell me what I'm doing right. I'm mentally prepared that not all comments will be positive, just as long as you leave criticism, I don't mind. But remember there is a difference between mean c...

Marley's Story: A Beach House Extra

by artiepuy on Sep 12, 2017
Erotic Couplings

This is one of several extra "mini stories" that are supplements to the Beach House series. Some of these will be elements of the story that I had in my head as I was writing a particular chapter, but which were left out because I couldn't fit them in or they didn't lend themselves to the first-person narration of the story. Others will be side stories that...

Easter Weekend

by Redrosesx on Sep 16, 2017
Romance

As I lay back in my seat on the plane taking me back home I looked out of the window and thought back to my night of Easter passion, my legs were still shaking, oh boy it was sure a good Easter had by all I can tell you! It all started when I landed at the airport around 9am Saturday morning. As I came out of the airport he was stood leaning up against his...