Shemale Taboo Stories

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Dick World

by darkness_drearing on Dec 25, 2019
Bisexual

For contributors As was stated at the top: while there were will be two general threads to go off of (for a guy and girl), feel free to create your own characters or scenarios. The only shared premise among them needs to be that they find themselves, however you decide that happens, in this universe and, as The Eagles would say, "You can check out any t...

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Craving Shemale Cock Ch. 01

by jeritza on Oct 22, 2019
Transgender & Crossdressers

I stood nervously on the dark cobblestone alley street, in front of the unmarked door, running through the possibilities in my head, speaking under my breath. I was thinking of all the events that led me to this moment - the perverted path I had gone down. This is it. This is finally happening. No turning back now. Dear god, no turning back now. *** I was...

Becoming Her Whore

by HerLittlePiggy on Sep 12, 2017
BDSM

"I know," my wife Casey said softly as her hands caressed my naked body beneath the covers of our king sized bed. "You know what?" I asked. I didn't know what game we were playing but I was ready to fuck. "I know what you look at on the computer and what you fantasize about," she answered softly. Her hand had found my hard cock and she squeezed it tight...

Twenty Questions

by silkstockingslover on Jan 7, 2018
Reviews & Essays

Summary: Jasmine responds to most common questions asked by readers. Thanks to: Tex Beethoven, thor_ph, Robert, and Wayne for editing. 20 Questions I get asked a lot of questions about myself and my writing. There was even an article by Bob_Aganoush called Literotica Authors 02: silkstockingslover. This makes me think I should go into more detail. So her...

Life for Futa

by GCStarnen on Jul 22, 2018
Fetish

Disclaimer: This story is the story "Living in a Futanari society"/Shemale Worldo but kind of reborn, somethings in the story have been edited here and there and some characters names and traits they have might also change from the original. (Such as the mothers name being changed). Also this story is hugely inspired by Futanari World/Shemale World...

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Jenna & Stephen Ch. 01

by Naf_Noparts on Sep 12, 2017
Fetish

(Author's Note: This is a true story, one that tells of my hot experience with a friend who fucked me with a strapon. If you are bothered by the idea of women ass-fucking men with toys, then this story will not be to your liking. Thanks in advance for all constructive feedback!) * Jenna and I have been friends for nearly 15 years. We dated ever so briefly...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

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! --...