Sissies Stories

1,006 results
Orientation
Length
Source
Infinite Scroll

Life according to Lizzie

by Lizziewannabe43 on Sep 16, 2017
Transsexuals & Crossdressers

As a word of warning this is more of like a pilot to see how this story goes if it is liked and good feedback is given then I will right more. Everyone mention in this story is above 18 years old and are not based upon real life characters. Please any criticism is accepted and highly encouraged thank you for reading my little tale...enjoy. ***** Luke began...

Clara Bow's Academy for Ladies Ch. 04

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Greville Hambleton tried hard not to think of the ginger sissy; he was married to a fiercely independent woman who was very much in charge in the bedroom, and who knew all too well of Greville's weakness for effeminate transgendered she-males. As he was often cuckolded, Tara his wife being partial to sampling cock, she turned a blind eye to his discretions....

Danni Ch. 02

by Coder3445 on Jan 20, 2020
Transgender & Crossdressers

This story starts where the last left off, read Danni to understand what is going on in this story. Of course all character are above the age of 18. The following story contain feminization and female domination. * Also another description Tara, Danni's Mother Unlike Danni Tara had tanned skin, she was five foot four inches tall. She had green eyes and...

The Femdom Milking Farm

by williewagtail on Sep 14, 2017
BDSM

1. In the yard The male human "cows" were all in the yard waiting to be milked. With the cows corralled together, the girls, Sara, Teri, Jo and Nancy liked top spend some time of a late afternoon inspecting their goods. Leaning on the rails, they ordered all the cows to line up on all fours facing away from them. Legs apart, yelled Teri, let's see what you...

Sissy Blane's Liquid Assets

by EvelynT on Sep 14, 2017
Fetish

ONE The Plumrose Dossier I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madam Harding at the Clinic. I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her he...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

The Office Ch. 05

by EasilyConfused on Sep 24, 2019
Transgender & Crossdressers

Tom had lost count of the number of times Hamilton had struck his ass with the wooden paddle. His cock ached for release but his unwitting periods of mental manipulation had embedded a control in his psyche. He knew that whenever he was in the presence of his Mistress he should seek her approval before acting. And that very much included ejaculating from his...

Little Larry Ch. 02

by pantywriter on Oct 9, 2018
Transgender & Crossdressers Stories

The transition from sleep to wake came rather early for Larry the following Monday morning. He rolled over and sat up, and winced as a blinding flash of pain hit him. "Owwwww fuck me," he moaned as he quickly adjusted his sitting position. When he stood it was slowly and carefully, and it wasn't until he had walked through his apartment getting ready for Mon...

Neighbourhood Terror to Sissy Pt. 23

by Fibaro on Aug 24, 2020
Transgender & Crossdressers

Chapter 25 While Marcy was doing her best to reapply the many makeup products Stephanie had shown her to use, Stephanie was making quick work out of repairing her own makeup. It was very clear that she was very practiced at it since she only needed a few minutes to reapply the complex look. The rest of it was spent sternly supervising Marcy's job. When she...

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...