Sissy, Heels, Cuckold Stories

88,578 results
Orientation
Length
Source
Infinite Scroll

The Robertson's Sissy Ch. 13

by Clite69 on Dec 2, 2019
Transgender & Crossdressers

*** The stories in the chain constantly shift in content. The main character may experience soft passionate encounters as well as humiliating rough sex at the hands of his dominant partners. All sex is mutually enjoyed by all participants as this submissive sissy is pushed to their limit. If you are only into softer stories in this category than some chapter...

LMC Ch. 02: The Camping Trip

by BobbieKayeCutie on Mar 13, 2019
Exhibitionist & Voyeur

Some years ago, an excellent writer of adult fiction, writing under the pseudonym "Little Joe," created several characters inspired by myself and several lovely ladies we both knew. One character was based on me, Bobbie Kaye, and was nicknamed Cutie, or Little Miss Cutie. Little Joe posted a number of these wonderful stories, in which Bobbie Kaye and her fri...

Dark Desires Ch. 01

by wantwhitewomen on Sep 12, 2017
Loving Wives

Please note that this is a hard core cuckold story and a black man fucking a white married woman story. If you read any further I will know and so will everyone else that you like this sort of story. You have been told. I would really like to thank WhiteWave48 for the help with proofing and correcting this story. She is a very sweet person and a great assi...

Elizabeth's Roman Awakening Ch. 02

by LeMondial on Sep 15, 2017
Interracial Love

6. In less than ten minutes, she heard a strong pounding at the door. She barely had time to wipe her pussy and squirt a mist of her favourite perfume between her legs and in the nape of her neck. When she heard the knock, she threw the robe on and raced downstairs. Breathlessly, she threw the door open and Joseph stepped through. He walked into her, backin...

Katrina Enjoys Her Cuckold Slave

by Robert_Anthony on Sep 25, 2017
Fetish

Alan stared out of the window, his mind far away from the reality of the overcrowded train. This journey had been decided on a week ago and since then it had been all he could think about, nervous anticipation coursed through his body and as the train approached its final destination the feeling rapidly intensified. The train inched into the station and Ala...

Grim Fairy Tales Ch. 01

by DocCIS on Sep 11, 2017
Group Sex

Author's Note: This story is a bit different than some of my others, not having any long-winded plot and only written in a day. It is merely a short (for me at least) spank story. Some may like it, some may not. It is merely a hot wife type story and a cuckold, so if you do not enjoy such things, move on... * Prologue My wife is extremely beautiful and se...

Sweet Ass Pt. 03

by stormbreyer on Sep 26, 2017
Loving Wives

Thanks to everyone who reads the stories on Literotica and provides feedback. Please leave a public comment at the end of the story or click on my username to send me a private message if you enjoyed reading it and want to let me know your thoughts. I try to respond to everyone who has a question or offers suggestions. And please remember to vote after you...

The Knave of Jacks Ch. 01

by WifeWatchman on Sep 13, 2017
Novels and Novellas

The chronological order of my stories is now listed in WifeWatchman's biography. Feedback and constructive criticism is very much appreciated, and I encourage feedback for ideas. This story contains graphic scenes, language and actions that might be extremely offensive to some people. These scenes, words and actions are used only for the literary purposes...

Degradation of Peg

by rich0524 on Sep 16, 2017
Interracial Love

All my stories deal with interracial sex, especially large dicks and small pussies. If this isn't your thing, find another story. * Ron was working at his brother's adult video store. It didn't pay much, but, he figured the fringe benefits would more than make up for the money. He had been watching the white wimps reading the interracial books and renting...

Happy Place Pt. 04

by Miguel59 on Sep 24, 2019
Loving Wives

Barbara's story. My gown has nothing to do with what I'm about to tell you. I'll save that story for another time. Those cotton panties, however, have everything to do with my story. Remember how I wore cotton panties when we first started dating and then one day I switched to sexy panties, the kind women wear. I'm getting ahead of myself. You've heard the...