Sissy Cum Inflation Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

The Visitor Ch. 02

by RobertoTropical on Sep 18, 2017
BDSM

Later that afternoon I found myself securely spread-eagled face-down on our bed with my mid-section raised by three pillows. As the two of them were tying me down, M. asked Emma if she wouldn't mind removing the giant steel butt plug. "Won't he feel empty and denied if we take that pleasure away from him," Emma asked. "You need for him to get something out...

The Best Medicine Ch. 03

by Evil Alpaca on Sep 13, 2017
Sci-Fi & Fantasy

This story is a bit wordy and fairly long, so if you are looking for immediate gratification, you might want to look elsewhere. The following story is a work of fiction. Any resemblance between these characters and events and any real person or events is strictly coincidental . . . and pretty darn impressive seeing as it is a science fiction story. Do not r...

The Adventures of Sage Tumbleweed Ch. 01

by RandyGonzalez on Apr 23, 2019
Sci-Fi & Fantasy

In Adventure 1, we find our intrepid agent, Sage Tumbleweed, on the trail of the alien infiltrators plotting to exploit Earth's resources. Galactic immigration was getting out of control. Not only that, but using humankind's dimwitted senses against itself, the alien marauders secret agenda included increasing the stupidity level on a global scale. Intending...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

On Her Terms Ch. 04: The Party

by econut on Sep 18, 2017
Fetish

Dale was just bending over to pull the laundry out of the dryer when his ass began to vibrate. The sensation caused him to jerk back upright. The vibrating butt plug, operated by remote, was his signal to go find his Mistress. It vibrated quite often throughout the day. His Mistress, Sam, a butch lesbian, had trained Dale to be a sissy slut, and her personal...

Chloe's Story Ch. 01

by MandyM1 on Sep 16, 2017
Novels and Novellas

The Dilemma As the tattooist's needle pierced my delicate skin and the painful process of inscribing the company logo above my bare pussy proceeded, I began to think again of all the chaos I'd recently caused. Derrick's bankruptcy and impending incarceration, the rapes of Carla and Amber, and the anguish that awaits my husband. I knew too what awaits me, th...

More than I Deserve

by StangStar06 on Sep 18, 2017
Loving Wives

Hey folks. I hope you all had a great Christmas and New Year. I'm starting the year off with a story that's a little bit softer in tone than usual, but we're gonna do some different things this year. Some of them are designed to involve you guys more in the story making process. Who knows maybe I'll fall flat on my face but it won't be the first time. So be...

Exposing Cindy Ch. 02-03

by cindyexposed on Sep 26, 2017
Interracial Love

Coming soon: Chapter Two: Exposing Cindy - Facing my husband. The evening with Denzel was uniquely dangerous and exciting experience. It was degrading and humiliating; and yet, I came three times. But most of all, it was stupid. It was irresponsible. It was wrong. I violated one of the fundamental precepts of my marriage. My husband, whom I love dearly, ha...

Road Trip Pt. 04

by TLCgiver on Sep 19, 2017
Novels and Novellas

... Continuing on from the previous chapter ... Chapter 18 North Dakota Bismarck is a pleasant little city and the state capital of North Dakota. I found myself surprised at how hilly the environment was, particularly near the Missouri River that cut through the city. I'd been on some pretty flat land getting there. The Northern Pacific Railroad dominate...

The Holiday

by Lord_Overload on Sep 12, 2017
BDSM

PART ONE It was a warm morning in late summer; Stef and Kayleigh were lying naked, bar their collars, on the sofas in the conservatory, enjoying the warmth of the rising sun. They looked over Exmoor, wondering what the day would hold. The two girls heard a noise and turned to see their Master, he was carrying a number of suitcases. "Morning Girls" He said...