Sissy Anonymous Cumdump 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

A Positive

by cpete on Sep 26, 2017
Loving Wives

Our son Tony was at the table doing his science homework, while my wife Gina and I set the table. Tony was a big boy for his age already over six foot. Both Gina and my family were of southern Italian breeding. Any family member rare enough to get near 5 foot 9 was automatically called "Goliath". "Who did I get my height from?" Tony asked. His science book...

Coming Home, Coming Out Pt. 09

by EiryCGar on Jun 1, 2020
BDSM

Author's note. As this saga continues, aspects of sadism, slavery, cuckoldry, lesbianism, denial and general bdsm are explored. All characters are figments of the author's imagination, and all characters consent to every aspect of the activities described. As always, all characters are aged over 18. Chapter nine. Saturday morning dawned, and Sara slipped f...

Queedom's Corruption Ch. 01

by SassyAnonymous on Jul 27, 2020
Sci-Fi & Fantasy

Hi everyone, I'm Sarah. Thanks for reading this! This story may be formatted a little differently than you may be used to on Literotica, and that's because it's a collaborative roleplay that is ongoing between myself and my RP partner Emily. I write from the point of view of Princess Alina and she writes from the point of view of Khalia, a succubus and the R...

Debt Collection Pt. 06

by shittylifelessons on Jun 8, 2020
Erotic Couplings

If you're new to the story, please start at Chapter 1. If you've made it this far, enjoy the finale. As with the previous chapter, I've combined two into one, so this one's pretty long. It's been a real pleasure writing this story, and I hope you all enjoy reading it as much as I enjoyed writing it. As usual, remember to rate and comment, I love hearing y...

Sissy Hubby Ch. 01

by buttboi on Sep 19, 2017
Loving Wives

From the beginning of our relationship, my wife Stacy has been the dominant partner in our relationship, especially with regard to our sex life. We have had traditional intercourse only once during our seven year marriage and it was a disaster like my three previous experiences. Since then she has refused to try again, insisting on oral sex. As I lay in be...

The Black Power Virus: Gold Digger

by amb_anonymous on Sep 13, 2017
Interracial Love

Hello BPV fans. This is a chapter that could have been a part of Chapter 3 in terms of timeline. It's a more cuckold-themed side story that takes place right at the start of the outbreak with a brief cameo from Cindy. As always, feedback keeps me writing. If you're not OK with heavy racial themes, than stop reading. If you're offended, why have you been re...

The Visitor

by Leanne_sissy on Sep 26, 2017
BDSM

He felt nervous, probably more nervous than he had ever felt before, he knew he was stupid to have ever let it go as far as this, but somehow he just hadn't been able to stop himself. He'd placed the chair in the centre of the lounge as he'd been told and now he sat on the settee looking at it, waiting. Waiting for the text message that he feared would come,...

Anonymous

by hyperpress on Aug 30, 2017
Fetish

I'm on my knees, staring up at a beautifully round, fleshy, tanned ass. It's spherical shape so perfect, and because the woman who belonged to it was bending slightly forward and bending at the knees as if she's about to sit down directly onto my open mouth I was infatuated and driven to fanatical heights thinking about it, looking at it, admiring it...it be...

Sissy Training

by kendra13 on Feb 13, 2018
Fetish

I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...