Risque Sissy Stories Stories

65,590 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

My Girlfriend's Sissy Roommate Ch. 02

by SEVERUSMAX on Sep 16, 2017
Loving Wives

"So, buddy, what gives? Or should I say, girlfriend, because, let's face it, we've always acted more like girlfriends in the platonic sense, well, minus your tongue going between my thighs. Other than that, you've been more like a female friend or a gay male one or something like that. Anyway, let's talk, openly now, about what Rain wants out of this relatio...

Southpark's Kyle Literotica Lesson

by RacheleRFranz on Sep 17, 2017
Non-Erotic

la la la"I can only give you everything I have" la la la "I know there's angels by your side. If I could be the perfect man in your eyes, I would give (anything?) to be a part of your life." la la wow hey Clay Aiken, thanks for the..umm, song in the background while I write! very inspirational! clap clap clap A trip to Hawaii? I LIVE in Hawaii! But I am a...

The Making of an Angel Pt. 04

by AngelLawrence on Aug 6, 2019
Transgender & Crossdressers

The story continues with the explanation of how I become a shemale slut. In the last episode I related how I lost my anal virginity to a stranger. All persons are over the age of 18. *** I got home to find thankfully my wife was still out. I stripped off my lingerie before jumping in the shower. My boi pussy was very tender and I gently slipped a fing...

K.U. High School Stories

by seannelson on Sep 17, 2017
Non-Erotic

(for those from less advanced cultural meccas: that's Klamath Union High School in Southern Oregon, USA) 1.) In freshman year, I went out for track and joined the long distance team. I did this because I wasn't very fast and really just did it for fitness and to see pretty girls in their track outfits. One day, I just didn't want to do the 5 mile run so I...

Young Sissy Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"Pleez...por favor...pretty pleez...fuck me..." I looked up at her with tears in my eyes, pleading to be penetrated. I didn't have to beg...nothing in the world would have stopped Lola from spraying her seed deep inside my ass...but I know it's what they wanted to hear. I regretted it immediately...well almost immediately...nothing can take away from the pur...

Hottie Diane Ch. 01: Just Us!

by HottieDiane on Jun 1, 2020
Loving Wives

AUTHOR'S NOTICE: Copyright © 2020. This is an original work by HottieDiane (alias). The work is protected under copyright by United States of America copyright law. This work is only submitted at Literotica.com and the Author has not authorized submission to any other site. AUTHORS NOTES: Our stories are first written for an audience of one, the love of my...

Futas & Fertility

by Genericc616 on Jan 4, 2021
Transsexual

A collection of short (probably) stories featuring fantastic futanari spreading legs and letting their seed flow. I'll be using this page to write a short synopsis of each of the stories, to give you a rough idea of the feel and themes each one will consist of as I think and add more. Alice - Sibling Rivalry heats up - Taboo, **** Alice and her twin siste...

Open in Reader

Daddy's Sissy Staircase Ch. 03

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

This is part 3 of a 3-part series, to understand better, go back and read parts 1 and 2. Thanks for everyone's comments, this has been my first story here at Literotica, and I have ideas for many more. Please feel free to contact me with ideas for future submissive sissy slut stories! My visits to Daddy now typically involve more time than just during the...

The Naked Bleached Blonde "Sissy Barbie Bimbo"

by Crissy on Apr 22, 2025

Did You Know? According to a study conducted on 293 female college students at the State University of New York in Albany, exposure to semen can lower symptoms of depression. And it’s mighty healthy: One teaspoon of semen contains over 200 proteins and several helpful vitamins and minerals including vitamin C, calcium, chlorine, citric acid, fructose, lacti...

Open in Reader

Down Under Dee

by SEVERUSMAX on Sep 17, 2017
Loving Wives

I sat down at my usual stool at Kieran's, an Irish style pub in my neighborhood, and I naturally expected to order my usual Harp's or Guinness, from my usual bartender, Kevin Murtaugh, a gruff, but otherwise likeable fellow always willing to lend an ear. That was not what happened, of course, or there wouldn't be a story to tell. At any rate, there I was, wa...