Sissy Bra Stories

144,731 results
Orientation
Length
Source
Infinite Scroll

No Choice

by AZgirlMichelle on Sep 16, 2017
Transsexuals & Crossdressers

You act as if this is news to you. I'm surprised that you would even question the fact. This isn't a bedroom game. It never was. I have a plan and you WILL follow it. Choice? What choice? Whatever gave you the idea you had a choice? I told you that things would change if you wanted to live with me. I told you it was my way or the highway. And what did you s...

The Unsuspecting Candidate Ch. 02

by missvicky53 on Sep 11, 2017
Fetish

Part 2 Helen continues Mike's training, this time in a French Maid's uniform The aftershocks of his climax were still coursing through his body as I teased him. "Did you have a nice cum, sissy?" I cooed at his still bound form. "Do you want me to release you now?" "Yes, please," he replied. "I'd like to get dressed now." "And get dressed you shall," I tea...

Step by Step Sissification Ch. 02

by satinmarabana on Sep 16, 2017
Transsexuals & Crossdressers

Over the years, I've been with a few different sissies who were in different stages of their exploration and this gave me the opportunity to participate with them and learn a lot. I've also spoken with a couple dozen sissies on literotica who shared their own fantasies and desires. This story is sort of a distillation of my favorite stuff. -- "Oh, well,...

The Awakening of a Sissy Pt. 04

by sissyjolie4u on Jan 27, 2020
Transgender & Crossdressers

After a long evening of studying, practicing, and of course grooming myself, I woke to a message from Mistress. The message read; Sissy Jolie, douche your pussy, bath yourself, and be ready to meet. Make sure you douche and your trainer is inserted. I'll be over around 11 and I expect you to be in matching bra, panties and your heels. Also, ensure your cocks...

The Pantysissy Diaries Ch. 03

by JPantyboyVSL on Apr 23, 2019
Transgender & Crossdressers

This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapters 1 and 2 before reading chapter 3. ***** It was nighttime in NYC, and Jaymie and her 6 Mistresses had just left their apartment to head to Vic...

Discovering Mistress Sarah's World Pt. 03

by oneguy4fun on Sep 12, 2017
BDSM

Chapter 7: A Brief Digression Mistress Sarah sat naked, in a stiff padded chair in front of a large vanity. She waited patiently for her two sex pets to return. It was time for Joe to learn how to properly dress her for a night out and she wanted him in full sissy attire for the event. May had been charged with the task of getting him back into his dress....

Being a Sissy for Viv Ch. 02

by Caron on Sep 25, 2017
Transsexuals & Crossdressers

After Viv's stimulation it took me a few moments to recover. By the time I looked around Viv was sat on the couch sipping at her almost empty wine glass. A slight smile on her lips and a satisfied look on her face. Our eyes met for a moment before hers wandered down to her pink lace fronted panties I was wearing. A wave of awareness swept over me as I sudde...

Tales of Sub Asian Sissy Ch. 01

by subASIANsissyJADE on Apr 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (I'm new here and this is my first post! I'd soooooo love to hear any feedback, questions, or comments! Many thanks, xxx, Jade) ***** I wore exactly what he demanded - he told me to dress like a regular girl... he told me he had nosy neighbors and, being a married man, he...

A Sissy Cuckold to another Sissy

by Gemsissy on Sep 26, 2017
Fetish

"Christ, Bob!" snaps Julie. You just sigh as you feel your skinny cock throb and spurt into the condom next to her bottom. "What about me?" "I'm sorry, honey. You're just too sexy! I came so fast!" you say, blushing in embarrassment that you couldn't fuck your own wife for more than 30 seconds. "Are you some fucking teenager dweeb?!" She spits as she glare...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...