Sissy Stories

6,529 results
Orientation
Length
Source
Infinite Scroll

Maiden Voyage

by jessicaj64 on Sep 16, 2017
Transsexuals & Crossdressers

Note to the reader – this is not a work of fiction. It is the story of how one woman found herself, in spite of the odds, and in spite of being born with a male body. It is entirely autobiographical, sometimes painfully so. But having read many tales of transsexuals, which end up being, in most cases, little more than tales about the cross-dressing fetish, a...

Savannah's Hypnotic Socks Pt. 17

by Fibaro on Oct 7, 2019
BDSM

Hello everyone, sorry for taking such a long time to update. Going forward I will try to get one story updated each month. I know that isn't a really fast pace, but I don't have a lot of time to write on my hands for which I want to apologise. I also know that I have made starts for a couple of side stories already without doing anything with them. I do plan...

1, 2, 3.. As Easy as ABC Ch. 17

by boo_dreaux on Oct 8, 2019
Group Sex

They were alone now. They only had each other now. But, for Tess and Jo, it was enough, it was all they needed.... "Thank you, thank you for coming to say goodbye to them,....." the, almost, identical words flowing from the sibs' mouths as they bade the well-wishers farewell, thanking each and every one, a 'well attended service' the newspaper would say in...

Living the Good Life Ch. 01

by DickThePimp on Oct 8, 2019
Celebrities & Fan Fiction

"Where's my darling grandson?" "He's upstairs. He hasn't been feeling well. Bridgette is taking care of him." "I bet she is." (Grandmotherly giggling) "She does a great job for my baby." "Yes. She's a talented employee. I'm glad she can help my grandson feel better. I'm more than happy to do that myself though, dear." "I know you are mom... so am I. Don...

Have Trouble? Contact T. Rex

by imhapless on Mar 31, 2020
Loving Wives

All characters in a sexual situation are eighteen or older. ********* In the early-1930s in the United States a small pacifist Christian sect known as The Lord's Sheep established itself near Moab, Utah. The sect consisted of fourteen adults (seven couples betrothed to each other before God) and sixteen children. All married couples, except for childless...

Submissive Cum Laude Ch. 01

by ChainedToAKeyboard on May 4, 2020
BDSM

It was a beautiful fall day as Alexander made his way across the quad to the campus library. Beaming rays of sunshine took the sting out of the crisp air and leaves crinkled across the ground as a light wind blew them about. He unzipped his coat, relaxing it around his tall, lean frame. His nostrils inhaled the unique aroma that only a New England autumn cou...

The Robertson's Sissy Ch. 01

by Clite69 on Jul 31, 2019
Group Sex

*Being a long time reader I finally decided to try writing my first story. I plan to make this a longer series so this part is a build up of what is to come.* Summer was finally here and school was out! For me it wasn't just out for the summer, but it was out for good! Through all the years of working my way through the public education system I finally gra...

Futanari Academy Ch. 04

by TheOrcKing on Jun 5, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Chapter 04 Bailey was surrounded by cocks. The smooth, girlish little twink was nude and on his knees in a soft ocean of satin pink pillows, com...

The Cruel Step-Mother Ch. 03

by Croony on May 13, 2020
Mature

'Good morning Timmy, how are you today? Did you sleep well?' asked Joanna, his step-mother as he walked into the kitchen. Timmy felt like telling her he would have slept a lot better if her mother had let him sleep. Joanna's mother Jean had been to his room after they had all gone to bed complaining she was horny and needed Timmy to do something about it....

Straight Crossdresser

by silkstockingslover on Oct 22, 2019
Transgender & Crossdressers

Summary: Guy dresses as a girl on Halloween and ends up performing as one. Note: This is a Halloween 2019 Contest story, so please vote. Thanks to: Tex Beethoven, and Robert for editing. * As I draped the sheer pantyhose onto my legs to finish off my Halloween costume, preparing for a night of cock sucking and bottoming at the annual Halloween men's onl...