Caught Sissy Stories

167,051 results
Orientation
Length
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Infinite Scroll

Casino Weekend

by Lindseycd4rp on Jan 15, 2019
Transgender & Crossdressers

Some days Will's cubicle felt like it was closing in on him, eventually trapping him inside. That feeling was self inflicted today which made it bearable. There was just one more hour of work before his five days of freedom. Five days at the casino, doing whatever he wanted with the guys. "Just a couple more things to finish up and I'm out of here," he thoug...

Thrusty's

by qoo123 on Nov 18, 2019
NonHuman

This erotic story features anthropomorphic (furry) characters, intelligent humanoid beings with both animal and human characteristics. "Thrusty's" SHORT STORY Gary and his wife Kat explored the sex shop, seeing what it had to offer. This place was a speciality retailer both of them had heard about online. It focused on breeding, reproduction, raw bareb...

Linda - "Before"

by nadiaden on Sep 23, 2019
Interracial Love

Special thanks to the Literotica member for editing assistance and excellent creative input. Thanks to the efforts of merrySM, new colors have appeared in this story. ***** Linda finished the usual household chores and peeked at her husband. Tonight did not promise anything unexpected. Having settled down in an armchair in front of the TV in anticipation...

The Sacrifice and the Scholar

by Tio_Narratore on Nov 26, 2018
BDSM

Once there was a small valley, nestled deep within the craggy mountains, and within it was a small village of farmers. For years they and their fields had received water bountifully from a large spring that gushed from beneath a granite outcrop. For three years now, however, the flow lessened and lessened until there was barely enough to sustain their lives....

After School Sessions

by AbsintheRose on Mar 26, 2019
Erotic Couplings

Math is, was and always shall be my worst subject in school. I scraped by with C's most of my high school career and college thus far was proving to be a similar situation. Except with college math my C's turned to D's and F's and as someone who heavily relied on the grants I got from the government to attend school, grants that required a certain GPA to qua...

The Chance to Change Ch. 03

by GalaxyGazer on Mar 30, 2020
Erotic Couplings

This was a brilliant chapter to write and I hope you all enjoy reading it as much as I did writing it. Another big thanks to my editor WokeUpOneDay for his continued efforts. Please support him and his work. Chapter 4 is already written and is currently being edited. Chapter 3 The morning started off well. We went through all of the software that we use...

Steve's Surprise Ch. 01

by BarbBud on Jul 8, 2019
Exhibitionist & Voyeur

Steve pulled up at Cindy's house a few minutes late. Although normally punctual, he relaxed on Saturdays. There were three cars beside hers in the driveway but he didn't think much of it knowing he would be occupied with a list of chores. He parked his truck on the street in front of the house, irritated that he was unable to park closer since he had tools t...

Emily's Bad Habits

by golden_eyes94 on Dec 10, 2018
Exhibitionist & Voyeur

As I looked in the mirror I appreciated my figure, my long legs, a somewhat shapely but not fat ass, a rather thin waistline and my perky C cup breasts, with a head of long blond hair to top it off. My pussy was adorned with a short neatly trimmed strip of public hair and already dripping in anticipation of what was to come. My name is Emily and I was 23, I...

Jessica Alba Gets Caught On A Hook

by JakesZA on Oct 21, 2019
Celebrities & Fan Fiction

The year of my 25th birthday a lawyer contacted me and informed me that my real father has died and left me everything, I did not really care about a man I never knew, my adopted parents had died the year previously in a car accident and money they left me with the other funds from their house and some other stuff that was sold was still untouched in a bank...

G Spot in Goa Pt. 06

by no1mf on Sep 21, 2020
Loving Wives

This is a genre I am exploring, part biography, part fiction, some imagination, full pleasure. All characters in this story are above the age of consent . Dedicated to S., my wife, the love of my life who has been gone for 7 years now, whose image comes to mind, as I put these words down. I write because it gives me pleasure. My initial writings drew great...