Smutty Sissies Stories

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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. 05

by SissyTwinkleToes on Jan 21, 2020
Transgender & Crossdressers

Susie can feel her diaper getting warm as she fills it with more pansy pee. 24 hours ago, she posted an envelope containing five keys, and still has another 48 hours until they arrive at her house. Those keys are for the lock that keeps her in her dress, the handcuffs that keep her right hand locked to this sissy on her left, and the tiny pinching chastity c...

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...

Ultimate Sissy Weekend Ch. 03

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Before today, Susie had only ever spanked herself. Nothing could have prepared her for the 220 spanks she'd received earlier, her first serious sissy spanking. Still her butt burns, even in its new pink poofy diaper. And now it's joined by fresh welts and lines on her inner thighs from the cruel canings of the redhead's ruler, as she happily decorates the tw...

Ultimate Sissy Weekend Ch. 04

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Susie is lying in the store supply closet next to Tinkerbell. It's six in the morning, and they've only just finished cleaning the entire supermarket. After changing each other into fresh diapers, and using the few left over to make pillows for them both, the two exhausted sissies lie side by side in the cramped supply closet. Tinkerbell's right hand, handcu...

Pillow Fight

by AmberFemXD on Sep 16, 2017
Transsexuals & Crossdressers

Five little Sissies laughing and giggling like goofy teenage girls exchanging recipes, sharing makeup tips, Omigawshing about everything, and who knows what else. Wandering around in the gossip garden . . . Planting new seeds, indeed. A night, tonight together. Funzies. Sissies only. No! Men! Allowed! Grrrrrrrrr. Purrrrrrrrr. SPLAT! And the slumber party b...

Ultimate Sissy Weekend Ch. 07

by SissyTwinkleToes on Mar 10, 2020
Transgender & Crossdressers

Ruby is sat flicking through a magazine. Mid-twenties, she's been working in the tattoo parlor since college and is soooo bored. So her face lights up when two sissy dumplings mince into the tattoo parlor. She gasps at their ridiculously effeminate outfits that no woman would be caught dead in. She can't believe they've handcuffed themselves together and loc...

Charlies Sissies

by Bisexual Zam on Apr 29, 2025

Once upon a time, there were three very different little boys... who grew up to be three very different Glammed-up, twerkalicious, super slutty Booty Boiz. They have three things in common: They're brilliant, beautiful... and they work for me. My name is Charlie. The sissies were hired, trained, and given new identities. Their old identities are lost to the...

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A Birthday to Remember! Ch. 05

by searic on Sep 11, 2017
Transsexuals & Crossdressers

Decidedly put in my sissy submissive place by Mistress Leader Marta, I resolved to be much more careful and obedient. I also was aware of my excitement at her Dominance and power. When another participant sat down next to me, I was recovered enough to look up to say hello. I recognized him as one of those I had seen earlier standing around and chatting afte...

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...