Sissy Loser 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

Lucas's Prom Night Ch. 02

by Lucas96 on Mar 23, 2020
Fetish

Author's Note: this story contains cuckolding, humiliation, homosexuality, and forced/non-consensual sex. *** After my prom night, my wish came true - I spent the rest of the school year receiving texts of pics and videos showing Jeff fucking one or both of the girls, and on lucky days he would invite me over to watch, even sometimes letting me suck his d...

Cream Puff Ch. 03

by RubixStu on Mar 25, 2019
BDSM

I was naked except for my wig, my makeup, my stockings and my heels. I sat on Roger's lap, his erect cock deep inside my ass. He was watching a nature program. My legs were spread and his arm was wrapped around me while his hand lazily toyed with my little boy parts. He wasn't fucking me, he was simply impaling me, filling me with his masculinity while I rev...

Arab Femdom

by Samuelx on Sep 11, 2017
BDSM

I think all human beings are bad news. Doesn't matter what their race or gender is. Even people who have been mistreated throughout history turn around and do the same exact thing to innocent others. It never ceases to amaze me. The bigotry some minorities can have for other minorities. Take my submissive Ahmed Aimren for example. He's a Middle-Eastern guy l...

Sissy Escape

by Haley_Hazel on Sep 26, 2017
Fetish

You are John Doe An average man, not too young, not too old. You have zero money, no car, no girlfriend... Basically a real loser. You live in a dive apartment downtown. It's not a great place to live, but it's home. Everything you need is right nearby. Groceries, Bar, Restaurants, it's near a park, and there's even a porno shop down the road. Because it's d...

Sissy Powers Ch. 09

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

When we made our way into the living room (with me back as Leah), Connor's eyes bugged out of his head. "MMM MMM NNN!" he screamed through his gag, a sock balled in his mouth and held in place by duct tape. "Oh, baby, sweety it's okay!" cooed Heather, moving over to him. "These wonderful people have shown me why our relationship is so bad! Good news, it's n...

Black Sissy For White Mistress

by Samuelx on Sep 16, 2017
Interracial Love

Right now, I'm lying in my king-sized bed. And I'm getting fucked in the ass. Picture this, if you will. A big and tall young Black man of Haitian descent getting fucked by a tiny, blonde-haired white chick wearing a strap-on dildo. My name is Stephen and this is actually my idea of heaven. I live in the Vanier sector of the City of Ottawa, Province of Ontar...

RRRing, Ring, Mistress Calling

by lushusboobs on Aug 30, 2017
How To

Part 1: Phone Domination Isn't For Losers As a phone sex Mistress, I hear a lot of excuses as to why people choose not to call ranging from "Why pay when I can get it for free?", "Phone sex is for losers", "I can't get turned on by it." to "I want the real thing, not a fantasy." They are entitled to their opinion, however, I think that many people are close...

Arnold’s Little Friend

by ittybittyht on Apr 29, 2025

Arnold Sebastian Stuart is a geeky nerd and has one little friend between his legs. He’s always been a big loser and has constantly been picked on. But now that he’s older than 18… things begin to escalate. So far Arnold has been able to keep his privates private… his one inch nub and all, but things are about to change… —— This story is humiliation focused....

Lucky Jack Ch. 02

by GreenFingers2015 on Sep 19, 2017
Novels and Novellas

LUCKY JACK Being the misadventures of one of life's losers. Chapter Three: Jack in Clover WARNING TO NEW READERS- This is a rambling, VERY British episodic part work which was originally published as a series of short stories in the 1990s but has recently been modernized and brought into the 21st century. The main character, Lucky Jack, some readers may r...

Payback - Ten Fold Ch. 02

by Turned on Sep 14, 2017
Loving Wives

Thank you for the all the comments on my previous submissions. I really enjoy being called gay, fag, sissy, wimp, and especially the more creative names like "dickless panty wearing piece of pig shit" -- it turns me on. I promise I will write one new story for every such remark -- so keep them coming so I can stay busy!! Chapter 2 -- Bad Influence "Hey b...