Shemale Taboo Stories

9,248 results
Orientation
Length
Source
Infinite Scroll

Letters from a Stalker

by Cinner on Sep 19, 2017
Transsexuals & Crossdressers

"How long have you been receiving these letters?" Det. Anton Judge asked the distraught woman seated in the visitor chair in his office. "About three months," she replied, clenching her fist and raising it to her mouth. "At first I thought that it was a sick joke from one of my idiot friends to celebrate Halloween, but after the second one I began to have m...

A Shemale in New Orleans

by Ganistaniro on Sep 16, 2017
Transsexuals & Crossdressers

New Orleans, Louisiana, May, 2001 As we approached the world famous French Quarter we were instantly excited. Bright lights lit up the street and the atmosphere reminded me of a carnival. People were everywhere! People were carrying giant buckets of booze as they walked the street yelling at women to take off their clothing. It was about 10 PM when we arriv...

A Night to Remember Ch. 02

by Master_and_Sex_Kitten on Sep 16, 2017
Transsexuals & Crossdressers

Happy Birthday to me...Friday April 24th was my four year anniversary of joining Literotica.com, so as a special treat, four new stories in one go! * Author's note: If you haven't read part one -- A Night To Remember -- that might help provide a little context :P this is a transsexual story about love, confusion and exploring a new world of sex. Enjoy! --...

Sissy Fantasy to Nightmare

by Anon729 on Sep 16, 2017
Transsexuals & Crossdressers

My first ever story here so I would appreciate any feedback. Hope you enjoy it! ***** Sunlight drifted gently through the hotel room as I woke up and rolled over to feel the warmth of Rosie next to me. "Morning sleepy head," she greeted me with a smile. "No time to waste if you're getting ready for the stag." It was just 3 days until our wedding and the...

A Son's Virginity: A Christmas Tale

by silkstockingslover on Dec 11, 2018
Illustrated

Summary: A mom gives her son the best Christmas present ever. Note 1: This is a 2018 Holiday Season Contest story so please vote. Note 2: Thanks to Tex Beethoven, Wayne and Robert for editing this story. 2018 had been a tough year for our family. First, a small fire in our house led to our losing almost all our family photos, among other less significa...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Secret Makes Him a Cuckold Bitch

by Subkoksukr4u on Jul 29, 2019
Fetish

Getting caught doing something kinky or sexual for some people is a turn on, for others it's humiliating. There's lots of different variations. Like when you get caught doing something with another person or get caught doing something by yourself. Anyway way you slice it, getting caught can be embarrassing to some degree. This story is about someone finding...

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

A Dare Gone Right

by sammicon on Sep 11, 2017
Transsexuals & Crossdressers

'Well, Paul, if you're not man enough, just say so!' 'Come on, that's not fair, Isabel. I've never dared you to do anything this risky,' I replied. 'Oh yeah? Walking around the mall in a pink latex micro-skirt and no panties wasn't risky? My balls were swinging around for all to see!' 'Yeah, but it wasn't entirely out of character for you. And nobody did...

The Devil's Harem Outfit

by Miles63 on Sep 18, 2017
Transsexuals & Crossdressers

Author's Note: Hey guys, when I was finishing my last story I found a file with this story half finished and I thought, what the hell lets finish it. Now this is a very very dark story with strong erotic horror themes that some may not find pleasing. There is some strong incest thrown in too. If you are not into that this may not be the story for you. Other...