Surprise Shemale Erotic Stories Stories

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"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

Asian Innocence Manipulated Ch. 09

by BeamMeUp on Sep 18, 2017
Erotic Couplings

In this saucy chapter a chance meeting in a Singapore beauty salon adds a telling new erotic dimension to the innocence of sensuous Selena, the buxom local virgin just one day out from her 20th birthday. The naive au pair to a 50 year-old masterful seducer, French photographer Jacques Pardie, is turned on by his ardent amorous charisma, yet she's determined...

What a Long, Strange Trip It's Been

by kurrginatorX on Feb 11, 2019
Romance

This is a Valentine's Day Contest entry. To vote, please click the stars at the end of the story. Thank you. ********************** Sunday evening I emailed Mrs. Sherman, my English instructor, with the following message: Mrs. Sherman, I know I have no right to ask this, but I need an extra week for my project. I have had one terrible incident after the...

Vendetta

by RexEatapuss on Sep 17, 2017
Celebrities & Fan Fiction

This is a true story, I swear, up to a certain point. It then becomes a fantasy of what may have happened, had things continued. Conversations are repeated as closely as I can remember them. Some names and locations have been changed to protect the guilty. ---------------------------------------------------------- I love my wife, but due to various reason...

Wannabe Cuckold Gets Found Out

by tombrennen on Jan 20, 2020
Fetish

A little about myself before I start the story. A trim 35 year old man that would probably be diagnosed as a sex and porn addict. As long as I can remember, I've been extremely sexual. Starring at cleavage and tight pants, led to porn mags and the occasional video, led to the internet. Once the internet exploded, so did my sexual fantasies. Shemale porn, and...

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...

Shemale Stories: A MILF Fucked

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Lonely MILF walks in on teen girl masturbating and.... Note 1: Thanks to Hernandez for doing the photos for this story as well as the plot bunny that led to the final story. Note 2: This is a 2017 April Fool's Day Contest story so please vote. Note 3: Thanks Tex Beethoven, Robert, goamz, With my daughter Simone away at band camp as a counsello...

Pam's Threesome Experience

by majicman21 on Apr 3, 2018
Loving Wives

Author's Note #1: This is a continuation of 'Pam's Shemale Experience' from the Transsexuals/Crossdressers category, as well as of 'Pam's Gangbang Experience' from the Group Sex category and 'Pam's Lesbian Experience' from the Lesbian Sex category. Reading those stories is hopefully not necessary to enjoy this one, although it will likely enhance said enjoym...

2019 Literotica Reader's Choice Awards Winners

by Literotica on Jul 13, 2020
Mature

The stories and authors below were chosen by our readers as the best of 2019, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of reading enjoyment, and to all of the readers for your input, support,...

2016 Literotica Reader's Choice Awards Winners

by Literotica on Sep 16, 2017
BDSM

The stories and authors below were chosen by our readers as the best of 2016, in voting which took place here. Though these are not the only wonderful authors and stories on Literotica, they are worthy of praise and recognition. Thanks to all of the writers for providing us with hours of hot reading, and to all of the readers for your input, support, and a...