Shemales Stories

429 results
Orientation
Length
Source
Infinite Scroll

Dickish Direction: Shemale

by Gweh on Apr 24, 2018
Transsexuals & Crossdressers

2:45. Friday. Three separate re-sets, personally handled. And very, very little patience left for his...'actresses'. Leon Whittaker's lip curled a bit further at that last thought, the mere word souring his mood, even as he kneaded his brow ever-harder, even as he slumped ever further back in his flimsy directorial chair, even as he tried again, equa...

A Romantic Story

by YKN4949 on Mar 5, 2018
Transsexuals & Crossdressers

"Oh my God, a honeymoon! How romantic! We went on cruise for our honeymoon too!" the bleach blonde, taut-skinned woman of about 42 sitting across from us gushed. She had that sort of drawn look that pretty woman who resist aging get. Hannah always called it "Courtney Cox Syndrome." But I wasn't focusing on her. Even looking across the table would make my hea...

Britney Story

by britneyfan on Sep 16, 2017
Transsexuals & Crossdressers

Yeah, for those of you that have already read it, this is just my "Oops, I Did It With Britney" story that has previously appeared in four separate parts in the "celebrities" section, but I've put it on here for a couple of reasons. For one thing, I've noticed that the stories in this section appear to get a lot more readers and a lot more feedback than in t...

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

Syn's Eden

by MadQuill on Sep 25, 2017
Transsexuals & Crossdressers

Please remember this is a copyrighted work and all legal disclaimers apply. I appreciate that the poor grammar may take away from the tale. My editing could be better and I continue to work on it. I'm sure there are some errors and I do care. Thank you for your comments. ***** The meeting was arranged by a voice on the hotel phone and it sound like a fe...

Mistress Maggie

by Joscelyn2tg on Sep 15, 2017
Transsexuals & Crossdressers

My Dear Reader, Welcome to a most unorthodox love story. A story containing romance, transgenderism, spirituality and yes, even S&M. But first allow me to ask you a question, and when you reach the end of this story, it will make much more sense to you. If your soul returned in the body of someone else after you died. And you were allowed to whisper one th...

The School Tramp

by tawnysuede on Sep 19, 2017
Transsexuals & Crossdressers

(From "Boy" to " Boy oh Boy!!") Chapter 1 - The School Tramp I was a virgin. I did not want to be a virgin. I asked my sister for help, and that was a mistake. Well, at the time I thought it was a mistake, but it turned out to be the best mistake that I ever made. I was nineteen years old at the time and entering my junior year of high school. Yes, my ju...

What Did You Do Last Night, Miss? Ch. 07

by Arsehole Addict on Sep 26, 2017
Fetish

Emma sat silently on the bed in her hotel room, her cheeks flushed, panting slightly from running up the stairs. The events of the previous hour swirled in her mind, a tangled web of erotic confusion. Her mind reeled in disbelief at what she had done. After all, she was a respectable woman, a schoolteacher no less, and yet minutes earlier she had been squatt...

Compromising Positions: A Fantasy

by GingerM on Sep 14, 2017
Fetish

This is a story born of a role-play exchange in the forums of a futanari-interest website, hence the credit to the other player. © 2010 Bishiebunny and GingerM Act 1 - A Fortuitous Meeting He wanted to visit Ireland, see the castles, the green hills, visit a pub and maybe explore his roots. She wanted Cancun, to hit the beaches and drink exotic drinks...