Sissy Truth Or Dare Stories

319,164 results
Orientation
Length
Source
Infinite Scroll

Creating Ginger Ch. 08

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Michelle awoke to the smell of coffee, which as of late had become her...

Neighbourhood Terror to Sissy Pt. 11

by Fibaro on Jul 2, 2019
Transgender & Crossdressers

Chapter 13 To Mark's huge relief he witnessed Lisa opening her shorts. Without the tight fly holding the dildo in place it would fall out, at least if Lisa hadn't taken a hold of it to put it neatly back on Mark's night stand. Lisa took off her shorts completely and her panties along with it. It was instantly clear that her neatly trimmed pussy was soppin...

Kasey's Confession Ch. 02

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

After Mike left, I stood in front of my big mirror and stared at myself. I kept thinking of all the excuses I had given myself, and other people, about why I shaved my legs and liked wearing short shorts, skirts, high heels and stockings. All that had changed in a single afternoon, although the writing had been on the wall for a long time. Even before I had...

Sissy's Shopping Trip Pt. 02

by SissyFaye on Jul 6, 2020
Transgender & Crossdressers

Hearing my beautiful mistress say that she needs to cum before continuing gets me excited. I have an idea of what she has in mind, but I'm not sure because this trip is different than any before. Mistress walks to the back passenger door and opens it, "Get in here on your back with your head on the edge of the seat," commands Mistress. As I comply, I not...

Another Submissive Slut Ch. 11

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

My land lady's knowing look held me transfixed. Quietly Mrs. Lehrer purred, "What are you?" A spasm of trembling shook my body before I could mew out, "I am a sub sissy slut, Mrs. Lehrer." "Hemmmmm," She hummed, "And what else are you slut?" Her voice was quiet, soothing, inquiring. "I am a wanton cum whore, Mrs. Lehrer," I admitted, blushing at such an a...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

Reversals Ch. 15

by RachelClark on Mar 27, 2018
Fetish

Alterations Bright lights and a murmur of women's voices poured into the hall as Pamala opened the beautifully carved door to the treatment room. Julia smiled broadly in anticipation as they entered. It was going to happen here, in this room. She could hardly wait to see it, to watch him get injected, and to see the look in his eyes afterwards. Julia could...

Mistress Marisa's Estate Pt. 11

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ******************************** The matron sits at the front of the room, gorgeous and tailored perfectly. She's wearing a tight short black dress and nee...

Sissy's First Day

by whispy_sub on Sep 13, 2017
Transsexuals & Crossdressers

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this." It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enrol...

Dani's Night Out

by Jemina004 on Sep 26, 2017
Transsexuals & Crossdressers

Danielle Winona was very nervous. Maybe it was because he was standing outside the door of a strange man's house at night in a mesh top, tiny skirt and thong panties. Maybe it was because he had just rang a stranger's doorbell and he had no idea of what awaited him inside. Whatever it was, and whether he enjoyed it or not, Dani had to be as pleasing and sexy...