Sissy Truth Or Dare Stories

319,164 results
Orientation
Length
Source
Infinite Scroll

Life With Miss Ida Ch. 05

by Sheermistress on Dec 3, 2017
Transsexuals & Crossdressers

Most evenings, dinner at home consists of me preparing all meals, serving it up to the table for both Mistress and I, having pleasant dinner conversations and then me cleaning up as always - just part of my Sissy role really, and one that I'm more than happy to undertake. And, dinner is always; entrée, light main meal and some kind of dessert - all served...

The Babysitter Takes Over

by sissysherry2 on Mar 13, 2018
BDSM

"I know your secret." These were the words that I had both dreaded and longed to hear from my babysitter. Let me start at the beginning. I am single and have a couple of kids at home who aren't quite old enough to be on their own when I have business obligations. I share custody with my ex, who left me to be with another man, who happened to be black. I ge...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Neighbourhood Terror to Sissy Pt. 12

by Fibaro on Sep 9, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Chapter 14 On Monday morning Mark got woken up rather roughly. It was only 7:30 am, but his phone was going off loudly. Confused he picked it up to see who would call at this ungodly hour. Nerves instantly struck him when he saw his girlfriend's caller ID pop up. What ha...

The Dragon Ring Ch. 04

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

The first days travel was wholly uneventful. We stopped to rest the equinininys mid morn; some people had brought snacks to eat while others including us took the air. My mistress declared that eating was bad for the digestion when one was thrown around on the track, which had turned to bare earth outside of the town. We stopped at an inn at lunch time t...

The Last Range War

by Egmont0409 on Aug 31, 2017
Humor & Satire

A SATIRE, perhaps historically incorrect in places. INTRODUCTION In 1912 a rancher's son Lee Stanton, aged twenty-two who was heading home after failing final exams to qualify as a pastor, unintentionally started an escalating feud between the Stanton and Murphy families that probably was the last of the range wars. You won't find it in history books beca...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

Barbara's Binoculars

by CarrieQ on Mar 21, 2018
Transsexuals & Crossdressers

A bit about the house I grew up in. It was one among many rows of identical boxes built after the war; an anonymous place with no obvious character, in an estate on the outskirts of a town in sharp industrial decline. My favourite room was the attic! I'd climb up there and pull the ladder up behind me, guaranteeing I wouldn't be disturbed. Mother liked to...

Made to Obey Ch. 08

by madetoobey on Jul 29, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

The Work Shower

by AnotherRandomWriter on May 2, 2018
Transsexuals & Crossdressers

Howard Bryce went to the locker room five minutes before the whistle blew. He was in a hurry, hoping to beat his colleagues so he could change into his street clothes unobserved, and protect his secret. He power walked through the factory, taking an unauthorized shortcut between two processing machines (an act that would get him suspended for three days w...