White Sissy Stories

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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...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

Sissy Chantel, New Reality Ch. 06

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Six: On My Way to My New Life at The Agency. Well the day has come for my transition in my life to becoming another sissy maid and sissy slut (aka: comfort girl) to 'The Agency'. Over the last two hard and humiliating weeks Master Camron and Sir Gage now as paid agents to my joining the team at 'The Agency' have helped me sell, give away or toss o...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters 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. Jere...

Recruiting of a Sissy Maid Ch. 10

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Ten: Changes Continue for Chantel as Her Relationship with Carl Grows. Awake and having a great breakfast superbly made by Carl, Chantel enjoys her morning with him. He has her in one of his robes as they talk about things and their future together. After breakfast Carl says, "Put on a pair of my jeans with your white satin blouse, you can wear yo...

Sissy Life

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I kept staring at the strap-on. I couldn't understand why it was out on the dresser. I tried not to let the concern show. I stood up straight - stood to attention - and thought back to the conversation that had led me here.... I was just finishing the washing up when my Mistress came into the kitchen. This in itself was unusual. Usually if she wanted me, s...

Life With Miss Ida Ch. 06

by Sheermistress on Dec 5, 2017
Transsexuals & Crossdressers

Life with Miss Ida – Part 6 - A New Development On most weekends Mistress and I would enjoy a nice wine or two with our evening meals however, on this particular Saturday, Mistress was enjoying more wine than she usually drinks – we had decided to do the twin, 'Schoolie-Slut' thing this evening, with both Mistress and I in matching, tartan mini-skirts, whi...

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...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

A Week End with Mistress Pt. 02

by gasissynora on Oct 30, 2018
Transgender & Crossdressers

Dear readers this is my first story and I hope you enjoy it. Your comments and suggests will be most helpful. I am planning on continuing the story if the feedback is positive. This story is based in part on facts and part on fiction. I will leave it to the reader to decide which is which. ***** I arrive at Mistress Nikki''s a couple of minutes before 2:0...