Interactive Sissy Stories

7,206 results
Orientation
Length
Source
Infinite Scroll

Release

by PrimitiveSexCord on Sep 15, 2017
Sci-Fi & Fantasy

The room was not terribly large, not like the factory floor. Several partial walls divided it into sections, though privacy was minimal and he imagined the walls were more to soften the noise and promote concentration. No one cared about privacy in here. Everyone participated, and no one was ashamed of what he did. Seeing what others did was exciting and...

Interactive Crossdresser...Dare Me Ch. 02

by PorscheKaru on Sep 16, 2017
Transsexuals & Crossdressers

Hi Porsche I loved your kinky stories and I think its hot how you let strangers tell you what to do. I would like to hear you do something more humiliating though... Are you ready? I dare you... to dress as a hot woman, very high heels, fishnets, tits on, makeup, but with a very short mini skirt and no panties. I want you to get a dog collar and a lead...

Pleasure Dome

by oggbashan on Sep 1, 2017
Humor & Satire

Years ago I had a computer game for my XT on two 360k floppies. It was called "The Pleasure Dome". I still have it somewhere. One floppy was for men, one for women. Once loaded the player had to chat up the opposite sex. Good chat led to higher levels and a better response from your date. Poor or hackneyed lines meant that you were stood up. It was all text-...

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...

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. 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...

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 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...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...