Sissification Relapse Caption Story Stories

136,310 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Rapture

by Emptyplanet on Aug 12, 2018
Fantasy

Introduction / Guidelines This story contains some explicit scenes that all might not find tasteful to their pallet, the story can contain various characters existing on the same or alternative timelines to the main story, it is completely up to participating authors whether or not they tie in the events to the cannon storyline, what aspects they add, change...

Open in Reader

Sissification 101: Ch. 03

by silkstockingslover on Jun 8, 2020
Transgender & Crossdressers

Sissification 101 Ch 03 Summary: Eric(a) gets pegged for the first time. 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 a very supporti...

sissy's life

by cdbaby on Apr 20, 2018
Fetish

INTRODUCTION: (sorry the way it was originally seemed unclear) Sissies, they're all over the world, and beyond. Discover their origins, their fears, their lusts.What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy? What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy?...

Open in Reader

My Initial Sissification

by ShemaleMaid on Sep 16, 2017
Transsexuals & Crossdressers

I love cum. Always did. Whether my own when I started experimenting, or that of friends later on. By now it's mainly the seed of older gentlemen who enjoy spending time with a sissy, and I love every minute! My clit simply drooling. By now it doesn't get hard anymore, and if there's a hint I slap it good. Stay small! I'm shaved, small, uncut, and the dream...

Submission

by Domestic on Sep 24, 2019
BDSM

Your name is John Doe. Where this story takes you is up for your decision. You can choose your gender, you can choose your significant other. But after that, you will lose the ability to choose. You will become obedient, like you know deep down you should be. Ready? Pick one, and begin. NOTE: {[email protected]}It is highly recommended that you play thi...

Open in Reader

The Male Fantasy

by TheKink on Feb 28, 2021
Fetish

This introduction will be short as I feel I have explained what this "book" will contain. However, if you are into aggressive and often times degrading sexual encounters that involve: Futa, sissy, straight, gay or bisexual characters.. then this story will hopefully be to your liking. • Stories will most often be in 2nd person. Please leave suggest...

Open in Reader

Sissification Fad

by NaughtyEricka on Sep 30, 2019
Transsexual

Sissification hadn’t just become some sexual fad overnight it had actually become a practical way of life for numerous families across the country. The act of sissifying a male family member and using them as a family sex toy and also as an alternate source of income had started in China and Japan but had quickly spread to and across the US. Now 3 years late...

Open in Reader

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...

Open in Reader

Mellow Yellow Ch. 21

by miskeivitch on Sep 16, 2017
Interracial Love

MELLOW YELLOW 21 Dr. Wu makes an urgent house call to cure Charles’ willie again The distinguished-looking woman mounted the steps of the stage. At first, one might think that she was wearing an ordinary business suit but a closer look revealed first one shapely leg, then the other, alternately flashing out the slit of the skirt. Dr. Wu mounted the steps...

The Ultimate Cuck Experience

by Joggles44 on Mar 12, 2021
Cheating Spouses

(UPDATE: Custom names for all main characters have been successfully added! Enjoy!) (Note from the author: Hello! Hope you enjoy my story. Before you start reading let me clarify that this story is set to "private", meaning no one can edit it or add chapters but me. I'd like to keep the writing to myself while the project is developing. HOWEVER, I...

Open in Reader