Teen Shemale Stories

11,725 results
Orientation
Length
Source
Infinite Scroll

Sweet Julie Birth of a Shemale

by tawnysuede on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One Is It Just a Role? The dress rehearsal for the drama club's latest production was over. The curtain fell, the audience of excited parents applauded enthusiastically. The curtain rose and the performers stepped forward to take their bows. The curtain fell again and still the crowd applauded. The two stars, Troy and Julie, took their positions ce...

Pleasure World

by Robopoop on Jan 20, 2020
Science Fiction

(( Author's Note: Once again, in my fit of inspiration, I leave behind a mess that makes little sense or impact. This post and all others later written by me will be undergoing significant amounts of intensive editing. Otherwise, feel free to post anything you like. The thread has been set to Public after all. Note 2: Posts are notorious difficult to organiz...

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The crazy ex girlfriend

by zbloutch on Sep 5, 2019
Fantasy

-I think there’s someone at the door. Peter sighed and looked away from the newspaper he had been reading since he had started his breakfast with his family. He looked at his wife and smiled. After sixteen years of marriage, as both were approaching their forties, he was still in love with Laura. Her brown hair, her blue eyes, not to mention her generous cur...

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BBC Shemale: A Beginning

by silkstockingslover on Sep 9, 2019
Transgender & Crossdressers

Summary: A lonely white woman in a gated community befriends new black neighbour. Note 1: This is a Summer 2019 Contest Story so please vote. Note 2: Thanks to Tex Beethoven for a massive edit to this story. Note 3: Thanks to Tex Beethoven and Robert for editing this story. BBC Shemale: A Beginning "Thanks for stopping by," the very pretty black woman, m...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Danielle Ch. 06

by sexgundam666 on May 27, 2019
Sci-Fi & Fantasy

"Come on! It's my turn!" Casey whined. She leaned against the bathroom stall, watching and stroking herself to the scene before her. "Sorry, ahh, it's so good," Holly answered from her prized perch, though she didn't move from it. A train of complaints and insults danced between them, all while the albino bounced, swayed and clapped her body against a might...

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...

Shemale Sisters Ch. 01: Creating a Slut

by hfernandez1983 on Sep 13, 2017
Illustrated

*-*-* *-*-* So, I have been away for a while. Things have been really busy lately, but now I finally have some time to start some writing again. I have tried my hand at writing a straight story on forced sex, a couple of lesbian stories and a couple of transsexual stories. I find that I get quite a few hits on the transsexual stories and that I don't ge...

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...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....