Shemale Caption Story Stories

702 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

Commissions

by Rekki on Oct 27, 2020
Miscellaneous

A combined ensemble of all the public commissions I made in 2020. All the mentioned characters are 18 years of age.What's next? Red on White - Asami Sato x Blanca Vasquez Futa-TF Kimono The Spartan Finals Tracy and the Greenhorn Barbaric Love Lordran's loyal whore What's next? Red on White - Asami Sato x Blanca Vasquez Futa-TF Kimono The Spartan Fin...

All Girl's School: A Cunt Fest

by silkstockingslover on Jul 8, 2019
Illustrated

Editor's note: this story contains scenes of incest or incest content. Summary: A teacher's lez side is awakened by a hot teen. All characters in sexual situations are 18 years of age or older. Note 1: This is a Nude Day 2019 Contest story. Note 2: This story was inspired by this caption photo by @Mistressr3: At the top was the following text: Ever si...

Exploring My Fetish

by fetishguy81 on Jan 7, 2018
Anal

Note: This story plays off of my previous 2, taking place after both of them. You won't miss too much but you can get more of the backstory by reading my other 2 stories first. ***** I developed to rather uncommon fetish's in pretty uncommon ways through out my life. My first was a fetish around salon capes and haircuts in general. When I was younger I dre...

The Rise and Fall of The Queen of Hearts

by Stormbringer on Sep 19, 2017
Interracial Love

A Golden Shower Universe story Copyright 2013 by Stormbringer * Olivia Queen Hart turned her BMW on to her driveway and honked the horn twice. It was a little ritual she did to inform her husband that she'd made a sale. Sure enough, he came out of their lovely three story house with a broad grin on his face, their five year old daughter in his arms. "Cong...

This Story Sucks Ass

by YANKEE DAN on Sep 15, 2017
Humor & Satire

Part 1, The Intro Some very few of you may know who Matt is. For those of you who do not let me make a short story even shorter. Matt was sucked into a dimensional portal created by the meeting of two very special books, soon after he met up with some shemales who turned him into a girl and banged him. Afterwards, he ran afoul of a tribe of penguins, and fl...

What It Takes Ch. 04

by YKN4949 on Sep 25, 2017
NonHuman

Dear Reader: This is part 4 of a 4 part story. All four parts are written and will be posted sequentially. In Part 1, struggling space crew member Luna walked in on a crew member, Dr. Janice Alton, sharing an intimate moment with a giant space slug. In Part 2, Luna was attacked by a space spider. In Part 3, Luna befriended "Rex" and helped him out. This is n...

BORG Collective Pt. 03

by bladeday on Jun 8, 2020
Sci-Fi & Fantasy

Prolog In the first story, I willingly agreed to join a BORG Collective, the acronym stood for Beautiful Order of Rare Girls. I was Invited to a Cosplay party where I would be assimilated. Arriving to Find ten stunning women with breasts exposed to my delight. Eight dressed as BORG Drones, the Queen, and Seven of Nine. After pledging to serve the needs of t...

A Latex Crossdresser's Dream Pt. 05

by shinyglove on Nov 18, 2019
Fetish

Please read A Crossdressers Dream parts 1-2-3& 4 before moving on to this story. *** The party was certainly in full swing as we had all seen some sort of action. The room smelled entirely of sex and latex, I was very happy with this as the aroma of rubber turned me on. Every time I opened the bag where I kept my latex collection the smell coming from it w...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

The Bio of a Masturbator

by Chatomana on Sep 18, 2017
Toys & Masturbation

Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital. Prologue This story is not about love, nor about romance, or...