You Are A Sissy Stories

361,487 results
Orientation
Length
Source
Infinite Scroll

Ultimate Sissy Weekend Ch. 02

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

It had taken a good half an hour via taxi to get to this postbox, across the city from Sissy Susie's home. All so Sissy Susie could post five keys to herself, containing the keys that keep her and Sissy Tinkerbell locked in their ridiculous sissy dresses, locked in handcuffs to each other, and locked in the clitty cages that have kept them chaste for the las...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

The Dominatrix Order Pt. 02 Ch. 01 - Sissies

by Jwwsmith on Jan 22, 2019
Transgender & Crossdressers

THE DOMINATRIX ORDER: FEMDOM EROTICA 2 BOUND BY LAWS BY J.W. SMITH *** "All Women Are Created Equal" was inscribed on the bronze plated plaque on display in Representative Johanna Aletheia's office. It was the declaration put forth by The Founding Mothers of Femininus, of which Johanna's ancestor belonged to. Johanna was of the oldest lineage of Feminin...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Sissy's Shopping Trip Pt. 01

by SissyFaye on Jul 13, 2020
Transgender & Crossdressers

"You finally got paid, Sissy!" my mistress says with excitement. "Yes, I did, my love," I say. "Well, I think in celebration of your first paycheck from this new job, we need to go shopping!" she says. "Oh really, shopping for what? I ask. "Clothes for me, and maybe some for you," she says. "Mmm, sounds like fun!" I say with excitement getting hard...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

From a Husband to a Dutiful Sissy Ch. 03

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Three: My sissy maid lifestyle becomes more set in reality. Morning comes and I carry on my new sissy morning ways, shower, shave, makeup and dress up in my maids dress, this morning a pink satin one over pink pantyhose and pink patent 5 inch spike heel pumps. I dutifully prepare breakfast for my Mistress Helen and get a bowl plain porridge for myse...

Thrift Store Sissy

by sissywendi on Sep 16, 2017
Transsexuals & Crossdressers

A story by wendi marie st.clair She was looking at girl's blouses the first time He saw her. Of course, most of the world wouldn't have seen her as a "she" at the moment, but wearing her flare-leg, hip-hugging jeans that were obviously from the junior miss department and the androgynous purple t-shirt that showed that she shaved her body, she looked like a...

Sissy Chantel, New Reality Ch. 04

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Four: More Sex, Public Humiliation and a Soon to be Turn for My Sissy Life. 8:00am and my alarm clock goes off, I am groggy as I awake but I soon realize I'm about to have another exciting sissy day with Master Camron and Sir Gage. I quickly shower and do myself up as expected in, make up, wig and my black maids dress, black sheer pantyhose and blac...