Sissy World Stories

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Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...

Black Femdom For Black Sissy

by Samuelx on Sep 11, 2017
Fetish

Sitting comfortably in her basement/dungeon, Ottawa's premier dominatrix Madame Whitley looked at her submissive, Shane Johnson, as the big and tall, formerly masculine Black dude stepped out. Clad in a pink Tutu, blonde wig, crimson pantyhose and high heels, the brother was finally letting out his inner slut. For years, Madame Whitley struggled to help Shan...

Discovering Mistress Sarah's World Pt. 02

by oneguy4fun on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 4 : Introducing Miss May! Miss May's arrival seemed sudden and quick to Joe. He heard the door close downstairs. Then there was the sound of somebody running up the steps. The bedroom door flung open and before Joe could look up to see anything, he heard an excited voice exclaim, "kitty-kat!" "I think someone is excited to see you," laughed Mistres...

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...

If Women Ruled The World Ch. 02

by chronoxxx on Sep 15, 2017
Fetish

I arrived at the bottom of the stairs of Sulihall College of Etiquette for the final time with my luggage, ready to meet my new Mistress. Nothing seemed real as I headed for the reception desk where 3 Ladies stood talking to each other, their towering high heeled silhouettes casting a shadow from the bright, unknown world outside. My mind was in a fug when I...

Sissy_World 04

by JDBones on Sep 14, 2017
Transsexuals & Crossdressers

Captain Darlene Marin of the United States Marine Corps sat in one of the many on base bars, a drink in her hand. She had many things on her mind, but the young woman was trying to drown out all of her thoughts. Drowning the thoughts and the memories was next to impossible though. How did one drown out the fact that they'd taken the lives of other women wi...

The Drop-Off

by Longo_Afar on Nov 18, 2019
Transgender & Crossdressers

"Where's my comb, Mommy?" Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls? "I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!" Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care...

Sissy Chantel, New Reality Ch. 07

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Seven: At 'The Agency' and I'm Off to a New Start In My Sissy Life. "Girls this is your new dorm mate, Sissy Chantel." one of the security staff says. The other staff member adds, "You shall take her into your group, help her set up her things and then take her around on a tour of the facilities and such. Report to the office after doing so, OK?"...

Natalie Continues to Learn

by natalieukcd on Oct 19, 2020
Transgender & Crossdressers

I could taste his cum and cock in my mouth all day from that first session. I was still very horny and that taste just added to my desire. It drove me wild wanting him again. I wanted him to treat me like Natalie again. I wanted to be sexy for him, make him hard. Yet, I did not want any of that. Welcome to the world of a sissy. The following day dragged. I...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...