Trans Mistress Stories

28,432 results
Orientation
Length
Source
Infinite Scroll

Modified Escort Service: Nancy

by Crimson_Spectre on Jul 27, 2020
Sci-Fi & Fantasy

Author's Note: it has been a long time since I wrote the original Modified Escort Service. Sorry I kept y'all hanging but I wanted to make sure I treated sex workers with respect and had to do a lot of reflection on how to get it right. I want this to be an anthology with a lot of diversity and respect for the escorts. Any feedback is appreciated. *******...

The Dream Job Pt. 02

by MrWidetool on Mar 24, 2020
Transgender & Crossdressers

The Dream Job - Part2 The new job was going great. The work was easy and the pay was good. Paul and Debbie had celebrated well into the night after Paul's interview with Jasmine Miabella. Debbie excitedly interrogated Paul for every last detail she could think of. Was she really as tall in person as she looks on TV? What was she wearing? How big was her off...

Onyx's First Summoning Pt. 01

by RubyDusk on Aug 7, 2019
NonHuman

Heya people, had to do some heavy editing of chapter one in regards to pronouns mostly, so I figured it would be good to post both chapters together. Feedback is of course appreciated. As a reference note, Onyx's pronouns are Ve/Ver/Vis/Verself and for comparison sake: Ve=he/she, Ver=him/her, Vis=his/hers, Verself=himself/herself. Chapter one The circle...

Ms. Greys' School Ch. 01

by Lydyia on Sep 15, 2017
Transsexuals & Crossdressers

written LJP edited another wannabe Preface:This school is for young women(18-20) and is focused on helping young trans women with their transition. Also I would like to thank my Editor for all his help. * It was already a long day and it was only 10 am. "I must discuss hiring more girls with Ms. Green tonight," Shelby exhaled. Ms. Grey's school for yo...

Teach Me Trans-Mistress Ch. 03

by JoannePare on Sep 12, 2017
Transsexuals & Crossdressers

Chapter 3 The Seduction/Domination Begins At precisely seven the bell rang, I answered the intercom and Ryan announced that he was in the lobby. Without bothering if any one else was in the lobby I decided to use the feminine name I had chosen, "Yes Nancy, come up to your Mistress!" and opened the lobby door. I walked to the elevator to wait for him not eve...

The Alex Experiment

by Certeis on Aug 21, 2019
Transgender & Crossdressers

Alexa timidly set foot in the bar, and was immediately assailed with a sense that she didn't belong there, but she fought back against it. She really wanted to go out and have some fun, to have a nice night without some creepy guys hitting on her or groping her. Last week she'd even caught some weirdo trying to put something in her drink, and she was thoroug...

Made Up

by ChewToySub on Sep 15, 2017
Transsexuals & Crossdressers

My first story on Literotica! Hope you like x ***** For the longest time, I've crossdressed alone. I taught myself how to climb into girly clothes, how to roll on tights without tearing them, how to put on my wig without it looking like roadkill. It took time, but I slowly learned how to get myself ready to enter girl mode. But there's a few things I've ne...

Writing Healthy Relationships

by yumeko on Sep 16, 2017
Reviews & Essays

I love written pornography. From the time I first discovered the written pornography in magazines when I was young, the written word has always been my favourite way to get off. And perhaps that should have been a clue to me, because I found out later that supposedly boys and men prefer visual material, but at the time I didn't much care. I only cared that r...

Shemale Orgy

by xploring96 on Nov 14, 2017
Transsexuals & Crossdressers

The following story includes transgender characters, Domination/submission and derogatory terms used to humiliate. If this offends you please do not read any further. Feedback on my stories is always appreciated. ***** All Ron could think about while he stared into her sultry eyes with their smoky dark eyeshadow was, how lucky I am that I am a faggot....

Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...