Pimped Out Sissy Stories

353,644 results
Orientation
Length
Source
Infinite Scroll

Sissy Gets Punished

by MsMorrigan on Sep 16, 2017
BDSM

Once upon a time there was an overly eager sissy girl. This sissy girl loved her mistress. She loved her so much she tried to anticipate her every whim before she needed to even speak the words. One day the sissy girl was vacuuming, dusting and general cleaning. She was openly lamenting on how her overly large pathetic sissy clit was getting in her way. How...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Jesse's Journey Down a Rabbit Hole Ch. 19

by sadkins116 on Sep 15, 2017
Illustrated

Jesse and Marcus tried to sleep, it was difficult with the ball and chain still attached to their butt plugs. They would drift off to sleep but then wake with a shock whenever they moved. The balls were heavy and slippery, weighing almost twenty pounds. The stainless steel finish was polished with a thin coating of something very slippery, like Vaseline. Whe...

Mistress Barbara Calls Ch. 03

by goamz86 on Sep 19, 2017
BDSM

Letter to the reader: This is a story of female domination of a submissive couple. It includes the man sucking dildos and taking thinks up the ass. If this is not your cup-o-tea, please find another story. Don't waste your time and mine reading it and making comments about me being a fagot or other asinine remarks, I will just delete them. Constructive comm...

The Dominatrix Order Pt. 02 Ch. 03 - Romance

by Jwwsmith on Feb 12, 2019
Transgender & Crossdressers

The next afternoon, Johanna invited many of the Goddesses of the Council over for lunch. Much to everyone's surprise, Representative Pencalia arrived as an uninvited guest. Pomona prepared a fine meal as the Goddesses deliberated over various issues. Pomona was very accommodating to the guests, serving them tea and salad and shrimp. She even placed cloth nap...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

The Government Lottery

by Girl Friend on Sep 15, 2017
Sci-Fi & Fantasy

Pandora had gotten the official government letter informing her she was selected for the lottery. The lottery was a secret ballot for the granting of a license to have sex. In the year 2099, it was illegal to have sex WITHOUT a license, and since babies were being bred via test tubes, a couple wishing to have a baby had to have their sperm and eggs surgicall...

Sissy and Paul

by slowhand1234 on Apr 22, 2019
Exhibitionist & Voyeur

Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married sev...

X-Men: Raven's True Blu

by Tara_Neale on Sep 17, 2017
Celebrities & Fan Fiction

Blue! Beautiful blue as far as the eye could see. Blue oceans teaming with life. Blue skies marred only by a handful of white fluff. Although in a few hours, the tropical afternoon heat might well give way to something more ominous. The white clouds replaced by storm clouds, but that was life. Storms always came when you were a mutant. Raven rested her hand...