Pantied Sissies Stories

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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...

Sissy Crissi Ch. 02

by sissycrissi on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2 -- Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and man...

Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...

Ultimate Sissy Weekend Ch. 01

by SissyTwinkleToes on Dec 24, 2019
Transgender & Crossdressers

Dressed head to twinkle toes in beautiful baby pink, Sissy Susie nervously waits for her friend to arrive and the most humiliating weekend of her life to begin. She winces as her teeny clitty squirms in its pink prison, a chastity cage that's been on for four frustrating weeks. Her cage is safely tucked away in her pink ruffly panties, covered in sweet littl...

The Booth in the Back

by mona215 on Sep 16, 2017
Transsexuals & Crossdressers

On my knees on the vinyl floor, the metal choke chain around my neck, one end of the chain under the pointed toe of her fuck-me heels, keeping me bent over so that my pantied ass is sticking up into the air. The sound of her crop slapping against my silky undies punctuating the mean things she says to me in a bored voice. "Real men don't wear girly panties...

From Husband to Man's Sissy Wife

by Pantypansy on Jul 8, 2019
Transgender & Crossdressers

I was pulling up my white panties and smoothing the tops of my stockings when I heard the doorbell, and my wife welcoming somebody at the door. He had a deep, Scottish voice. Lucy welcomed him into the living room, then closed the door and came into the stairwell and beckoned for me to come down. I felt a chill of fear, but tottered down the stairs in my...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Sissy Maid to Be... Ch. 02

by missjennymaid on Sep 10, 2018
Transsexuals & Crossdressers

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jeremy is get...

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

A New Life Ch. 05

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

I remember that night I drove myself home from work after getting her phone call filled with humiliating demands and insinuations. I was in an absolute panic. I had no idea if Mistress Sally was serious about all of this, or if she was just playing elaborate games with me. But I honestly feared the worst, and my fears were realized as I pulled into my drivew...