Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

The Dutchess and Me

by cuckytoher on Sep 11, 2017
Fetish

CHAPTER 1 When I met my girlfriend she didn't know what the term cuckold meant, let alone have any interest in participating in the actual lifestyle. Oh, she knew that one of the reasons for my recent divorce was that my wife had left me for another man after an ongoing three year affair, and was now living with him. She also knew of my submissive tendencie...

Olympus has Fallen Ch. 23

by Gaius8666 on Sep 19, 2017
BDSM

Peander was fast asleep. In fact, he was in a slumber, deeper than any doze he had enjoyed his whole young Greek life. This was that sleep that comes only to the well fed, the well drunk and the well fucked; and he was all three. Laying flat on a large bearskin rug in Freya's tent, his face was frozen into a wide-toothed grin. His neck, chest and back were c...

St. Clair Ladies Circle: Beginnings

by 1946EW on Sep 14, 2017
Transsexuals & Crossdressers

I Become A Woman (Author's Note: I Become A Woman is the true name of this chapter. Since Literotica's protocols do not permit long titles, I shortened the title used by Literotica. * My name is Valerie. Well, my en femme name is Valerie. For the past two years I've lived as a woman—dressed as woman, presented myself to the world as one, think lik...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Ensnared by a Corset

by spinder on Sep 16, 2017
Transsexuals & Crossdressers

Warning: This story is a work of fiction and contains descriptions of explicit sexual acts between women. If this type of content offends you or you are under the age of 18 do not read it. Author's Note: This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at you...

Transforming Brent

by sissymissyct on Jul 9, 2019
Loving Wives

Katherine decides she wants to live with her lover Wendy. They come up with a plan to slowly change Wendy's husband, Brent, into their girly sissy maid full time. Will his resistance be broken? I put it in loving wives but it fits multiple categories. Will he will learn to love his new role in life? Yes, The narration switches between characters. If this bo...

Sissy Shopping

by Candour on Sep 25, 2017
BDSM

My first story, finally edited and tidied up. I hope you enjoy it, I enjoyed writing it. --------- You were standing in your local department store in the make up section, looking for foundation. Not too sure what you are doing, and must have looked a little lost as one of the sales girls came up quietly behind you. She was a delightfully pretty 18 year ol...

Katelyn's New Sissy Pt. 01

by bluesbirds on Dec 25, 2018
Transgender & Crossdressers

I remember she made me try the Sissy Peni-Pacifier in the store. It was a humiliating day outing, meant as "my" Christmas gift. Dressed up in a tiny bright red sexy elf costume with marabou trim around the edges that ended at my sissy clit, black fishnet stockings and 4" black heels, with a ridiculously large shiny red bow in my hair, surrounded by mirrors a...

Casey's Submissive Journey Pt. 07

by corduroysissy on Mar 6, 2018
Transsexuals & Crossdressers

Note: This part of the story, and those to follow, occur after Karen had been accepted into the Lady's Club. ***** Karen spotted Betty Jean from across the room and she looked interesting. The ladies were all watching their husbands sucking and fucking each other in full drag, it was Fag Night at the Lady's Club and the sissies were giving them a really go...