Sissies Entrapment Literotica Stories

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Clara Bow's Academy for Ladies

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she'd also chose...

Something New Something Old Ch. 03

by dorian87890 on Sep 25, 2017
Fetish

Ted's life had been turned upside down in the last five weeks. He was currently on his hands and knees in the bed of his neighbors' Josh and Nancy. A pair of pink panties were at his ankles and he was wearing a matching pink bra. His cock dangled between his legs trapped in a cage. Nancy was behind him with a strap-on. She was fucking Ted mercilessly. Josh...

Life underfoot

by softspank on Apr 29, 2025

Rodney was used to living in a world full of giant women. He liked to travel but the only way he could to do it was on the cheap. He would hide in a women's shoes and without much thought these women would flatten and crush Rodney under their foot. He would be stuck under the person's foot for the entire flight. Once the person reaches their destination he w...

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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...

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...

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...

Shelacta Tales Ch. 13

by oggbashan on Sep 19, 2017
Sci-Fi & Fantasy

If this is the first Shelacta Tale you have read, please go the appendix to learn about this world. Copyright Oggbashan November 2010 The author asserts the moral right to be identified as the author of this work. This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represen...

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...