Prissy Sissy Stories

7,690 results
Orientation
Length
Source
Infinite Scroll

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. 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...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

BoyTrainers, Inc.

by LicoriceOrElse on Sep 19, 2017
Transsexuals & Crossdressers

Peter was taking a long time in the shower again that morning. His mother pressed her ear to the door, and detected soft moaning. Inside the shower, Peter stood, pumping his penis with his hand, eyes squeezed shut. He was a little underdeveloped for 18 – short for his age, and didn't seem to be going through the final stages of puberty just yet, but he was...

Robin and Jimmy Olsen - Sissies Ch. 02

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Chapter 2 Robin prepares, Alfred beware! The evening before the date in Part 1... Sitting in her resplendent suite of rooms in the Manor, Robin inhaled a slow drag from her cigarette. As she exhaled the stream of smoke, she admired her lipstick on the filter of the cigarette. It was funny. More than a year ago, when "he" was just "Dick", he was appalled...

A Birthday to Remember! Ch. 04

by searic on Sep 11, 2017
Transsexuals & Crossdressers

A Birthday to Remember Part 4 In some ways the meeting room in which Haley and I found ourselves looked typical of the species: there was a long table labeled "Welcome--Registration"; A couple of folks behind it helping individuals sign in; a coffee urn with cups, cream and sugar; next to it a selection of cookies; and a place for seating with whiteboard,...

Man Disciplines Sissy Ch. 01

by LanaBehave on Sep 14, 2017
Transsexuals & Crossdressers

I enjoy nice undies, sexy undies, soft and pretty lingerie, and delicate and dainty clothes whenever possible. I put on these things, and feel feminine and aroused, eroticized....the pretty dress, the wig, the nylons, panties and bra, heels... I also feel the misbehavior aspect. A boy/male like me, even if it looks sexy or feminine on me...dressing girly is...

House Rules Ch. 09

by EROTICbearscribe on Jan 22, 2020
Transgender & Crossdressers

AUTHOR'S NOTE: This story contains characters and references to events in two previous stories I have written: Just Across The Hall and PIXIE: Sissy Stripper. It is not necessary to have read these two story chains. This chapter of House Rules could stand on its own for entertainment purposes. If, however you want context, please read the other two stories f...

A Downtown Moment

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the company. While I never went out with Loretta, we did have the od...

Fifi La Femme: A Pansy at Last

by pris69696 on Sep 16, 2017
Transsexuals & Crossdressers

I have written this story "Fifi La Femme-A Pansy at Last" mainly from personal experience as a mature homosexual transvestite who was a gay virgin until my early 40s. I hope that it will appeal both to extreme effeminates and the ultra-masculine men they ache to serve. Now divorced I've been living with my boyfriend Ron for three years as his gay wife and ye...