Sissification Story Stories

65 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

Soft Sissification

by Lying_Smitten on Feb 21, 2019
Fetish

Welcome to the softest sissy story around, but first you need to choose your character. Would you like to play as the Sissy themself, Mike, soon to be known as Mia, a 5'8 man with dark brown skin and black hair, with equally dark brown eyes, and a slightly soft build? Or would you like to play as the Sissy's sweetheart, Kate? A woman of the height of 5'6, wi...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Sissification 101: Ch. 02

by silkstockingslover on May 18, 2020
Toys & Masturbation

Summary: Both Eric(a) and Joan discover the joys of toys. Thanks to the real Eric who requested and helped plot this lengthy story. Thanks to Tex Beethoven and Robert for editing this story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose wat...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...

Sissification 101: Ch. 06

by silkstockingslover on Sep 28, 2020
Interracial Love

Sissification 101 Ch 06 Summary: Eric gets fucked by BBC for the first time; Joan gets black pussy. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by...

Tricked into Sissification

by AnalOnlySissy on Aug 4, 2020
BDSM

Rene: How do I get her to go out with me? Brittani: You dont! Hahaha. She is way too pretty for you. Rene: I know. It's just I really like her. Isn't there anything I can do? Brittani: I can put in a good word for you, but you have to do something for me. Rene: Oh that would be so great. I'll do anything please. Brittani: Hahaha you are such a pathetic loser...

The Sissification of a Hero

by Clutterspunk on Apr 22, 2025

Izuku Midoriya loved being a hero. He loved saving people with a smile and giving strength to the weak. He loved the feeling of doing something great and the happiness that followed from the people around him. Something he did not love however was paperwork. Sadly however, with great responsibility comes a great amount of paper-work. Especially if you're the...

Wet Dream

by sissymissyct on Jan 21, 2020
Fetish

@2020 by Brenda Goodwin (This story deals with fem-dom, sissification, diaper wetting. If that offends you please read something else.) * "You're still playing that World of Warcraft game I see. Well, I am going to bed." "That's OK hun, I got a new "white-noise" machine so the noises won't keep you up. Just put in the earbuds on the side table and I will...

Everything Has a Price Ch. 06

by MALIBUMAN666 on Sep 14, 2017
BDSM

Author's note: This story doesn't seem to be as popular as some of my others, I don't know why that is particularly... it's a lot more 'real', certainly more 'real' than 'Owned!' or 'Out of Your Hands' which are both quite far-fetched really... It doesn't bother me particularly I'm just interested to know people's opinion and so I really do welcome your feed...

Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...