Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Tai's Story Ch. 05

by Cagivagurl on Nov 4, 2019
Transgender & Crossdressers

So back at work and it was hot and sticky 300 KM from anywhere. The daily temperature on site was close to 45 degrees Celsius and I had never seen rain in all the time I had been there. It was hot dry and arid. Work was becoming more and more of a chore. When I started here initially it was amazing. It was good to get away but now it was becoming a drag. The...

Born to Be Ch. 04

by DamienDeath20 on Dec 9, 2019
Transgender & Crossdressers

A.N. Back at it again with the interracial pegging!! Thank you all as always for your patience while these chapters come out! And thank you a huuuge amount to my supporters! :3333 you guys make it so I have food on the table and can keep doing what I love! The Following Contains: Black Amazon Woman on little girly white boy who is progressively becoming...

Sam and Jodie - A Fairy Tale

by 33shadesofmorg on Jan 21, 2020
Transgender & Crossdressers

THE CHRONICLES (AND THE CHARACTERS) OF SAM AND JODIE (A FAIRY TALE) PREFACE THE HORN I am looking for a unicorn. But I cannot find this beautiful and magical creature. Something so rare and special that few believe exist. But I believe. I know she is out there. I also know that when my unicorn and I find each other - boom - explosions of sparkle dust, a...

An Interview with a Trample Lover

by TeroWright on Jan 21, 2020
Letters & Transcripts

Author's Note: This story correlates with Christie's trampling adventures commonly found under the 'Fetish' category. It has been converted from a fictional transcript, and is therefore mostly TELL and very little show. The interview is done in real-time and is a tad over an hour long. ----------------------- Not being one to shy away from something differ...

Under My Umbrella Pt. 01

by R410a on Mar 16, 2020
Interracial Love

All who participate in sexual activity are 18 or older. The impetus for this story derived from a request by another member for a bwwm story with a certain theme. If you're looking for a story with lots of quick sex this one will disappoint you, there is a lengthy build up to intimacy. Consider yourself forewarned. ***** Though I had a wide umbrella ass...

Finally a Princess Pt. 02

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

Part two of a crossdresser who loves Disney who has come out to his wife while on a Disney Cruise. New experiences and adventures are ahead. Finally a Princess (Part Two) I woke the next morning around six thirty which was a little late for me. I laid in bed and thought about what had happened yesterday. I had actually spent time in front of my wife Sarah...

The Professor's Women Ch. 11

by jsmangis on Sep 25, 2017
Erotic Couplings

This is the eleventh installment of my story about a family with an interesting dynamic. His Baby returns, and a new Mommy joins the family, but something is not quite right. * Note to my readers: This chapter contains references to certain religious practices that may offend some members of a particular Protestant Sect. I apologize in advance to anyone w...

Destroy and Rebuild Pt. 08

by The Avenger on Sep 16, 2017
Interracial Love

Chapter 1: Setting up Robert Jay told Dianne not to tell Hilary about him fucking two of her brothers. "She might hate them for being ass holes and never supporting her, but blood is thicker than water. We can only trust her completely when she had delivered my child. Coz then, she will stand behind the father of her children." Therefore, Hilary was kept...

I Spy On Love

by FantasyXY on Sep 13, 2017
Romance

My name is Gunn... James Gunn. I am a spy. To be more accurate, my life's work is in intelligence, if you actually want to call what I do intelligent. I guess you could say I'm a spy, but it's not what you might think. My profession is actually pretty pedestrian. It's just a job, not unlike any other line of work. Sure there are more cloak and dagger jobs...

Whistler's Mumma

by Sputnik57 on Sep 12, 2017
BDSM

Synopsis; 'Plain Janes' are not always as they seem – some have been tutored by relatives who lurk in the background, waiting to receive those caught in a contrived web. Jane Whistler's appearance was that of a well groomed, prim and clean living girl. At 30, she appeared to have been left on the shelf. She rarely socialised, other than to indulge her work...