Pegging Sissy Stories

7,509 results
Orientation
Length
Source
Infinite Scroll

Commander Murphy's Woman

by Grey Eagle 286 on Sep 13, 2017
Romance

Commander Andrew David Augustus Murphy, U.S. Navy (Retired) sat in his lounge chair and watched the Fox News Channel. He was not pleased with what he saw. He was disgusted with the way the war in Iraq was going. Having a fair amount of experience in the Mid-East he was of the opinion that bringing all the factions together in a common government was next to...

Killing Daddy Blue

by WickedDrX on Sep 12, 2017
Novels and Novellas

Wednesdays were always boring for Holly, and this one was worse than most. Her usual trade didn't hit the streets until the end of the week when they got paid, or until the welfare checks came. This wasn't the week for the welfare checks. It was cold, and there was a light mist falling that promised to turn into snow very soon. She could move up a few blocks...

Birthday Present Pt. 01

by donnaallure on Sep 18, 2017
Transsexuals & Crossdressers

Birthday Present or (I've Looked at Love from Both Sides Now) Chapter 1 "What would you like for your birthday?" my wife asked. "An unforgettable sex session" I answered, jesting. "Is that right? Well, we'll see" came the reply. I forgot all about the exchange and nothing else was said about my birthday. The day arrived and I got home from work exp...

Flowers in the Heart Pt. 02

by JimBob44 on Sep 15, 2017
Transsexuals & Crossdressers

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. **Author's Note: This has an alternate ending to 'Flowers in the Heart.' It read the same as the original posting, until page 4. After posting the story, I realized that Scott was just a little too quick to accept his girlfriend's differences, especially...

Coming Together

by davepepperbury on Feb 25, 2019
Novels and Novellas

"Get that down you," Suzi said, "and tell me all about it." Linda took a long swig of the chardonnay, and sighed. Where to begin? The trouble was she had so much going on, and none of it was really a problem, on its own. There were no real money problems to speak of. Yes, she was doing two jobs - part-time at the school, and these occasional PR events with...

The Old House

by l_anonym on Jan 22, 2019
BDSM

Prologue This story is about a group of young people living together in a big old house a bit outside of town. Most of them are students so they enjoy the rather cheap rent and the somewhat secluded place where they can party anytime without having to worry about the neighbours. Don't get me wrong: It's not a place with a nonstop party -- they all have to...

Awakening: 7 Slutty Blackmail Tasks

by silkstockingslover on Mar 20, 2018
Illustrated

Summary: MILF's sexual awakening by being forced to do 7 slutty tasks. Note 1: This is an April Fool's Day 2018 Contest Story so please vote. Note 2: Thanks to DARKBREEZLY for collaborating with me and creating all the illustrations that bring this story to life. Note 3: Thanks to: Tex Beethoven, thor_p, Robert, and Wayne for editing. Note 4: A warning:...

By Demon's Driven

by xelliebabex on Mar 12, 2019
Novels and Novellas

Author's note: The story is part of Literotica's unofficial tag team competition. Twenty of Literotica's authors have accepted the challenge of being randomly paired with a partner to co-author a story under the pen name "The_Odd_Couplings." The pairings have remained anonymous and the true authors of this story will be revealed in the comments section one w...

Wingnut

by ausfet on Mar 7, 2018
Non-Erotic

Robert leapt up the polished hardwood steps of the New Farm art deco apartment building, an overnight bag slung over his shoulder and a bunch of flowers in his hand. It was Friday night and after a two hour journey he was just metres away from his destination. He'd first made the trip to Audrey's home twelve months ago. He'd gotten hopelessly lost driving...

Dawn's Darkest Hour

by msnomer68 on Sep 11, 2017
Novels and Novellas

114 chapters plus epilogue. Everyone in the story is specifically stated as being eighteen years old or older. ***** Prologue The Great Father wound his way through the destruction sickened by the death around him. A once thriving village lay in a heap of smoldering ruins. The bodies of brave men who had fought to protect their families were scattered lik...