Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

The Tales of Crissy the Sissy

by EPCene on Oct 5, 2020
Transgender & Crossdressers

Chapter 01 Halloween night 'Those guys are real fucking assholes,' Chris Masters thought as he walked alone down the crowded street. He had known most of them for the better part of a year and never thought they could do this to him. They had met at work. Chris was the new guy and was instantly brought in to meet the rest of the middle management team. Th...

Cam Slut Pt. 01

by GavinIsaNuisance on Oct 26, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Eighteen year old Jeremy Briarstein is forced to remain home while his parents go on an extended twenty year anniversary vacation. He is further dismayed to dis...

A Small Favor

by ToSexorNotToSex on Sep 28, 2020
Transgender & Crossdressers

Note: You rarely see Futa-On-Futa stuff on Literotica it feels like, so I thought I'd give it a shot. Second Note: For those of you who are unaware, a "futa" is a person (generally feminine) who possesses both genitalia. E N J O Y! --- "God, why don't you two just get married already?" "CHRIS!!!" It was a bright, sluggish Monday afternoon. Currently...

Celeste Pharma Ch. 01

by HorribleHenry on Oct 12, 2020
Transgender & Crossdressers

CELESTE PHARMA CHAPTER ONE I needed to get some money really badly. If my life didn't depend on it my well-being certainly did. Any spunky twenty-four year-old male worth his salt would have wanted to fuck Carla Pincher.- and I was no exception. Undoubtedly Carla set out to trap me. Who could blame her for wanting an exit with a family like hers? Why did...

Maid to Order Ch. 01

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele Ascending My wife had left me a year ago. I'm surprised she waited as long as she did really. We were married when we were both eighteen when I was in the army. She had been my only girlfriend and I was scared she wouldn't wait for me because I was being deployed overseas. It was a whirlwind romance. I'd heard rumours that she'd been a bit loose be...

Bob, Sue and Anita's Romance Pt. 02

by Nellymcboatface on Nov 16, 2020
Transgender & Crossdressers

Dear Reader, hopefully, you will enjoy my second chapter of this story. By all means read the first to ease you into this one, as Bob isn't so coy in this one. I am happy to receive comments and PMs. I welcome constructive criticism. --------------------------- In the morning Bob convinced his wife he was getting out early to meet up with the, "lads," f...

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...

Matt Becomes Mattie Ch. 04

by clarepanties on Sep 14, 2017
Transsexuals & Crossdressers

The morning seemed to quickly arrive and I awoke in Jo's arms. She gave me a kiss and said, "Take your time, I will see to the children, but you will need to slip into your tracksuit bottoms or something before they see you in your pink glory." I slowly got up, did my basics, including a douche, threw on some clothing and went through to the kitchen and h...

Cockatoo Pt. 06

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback We stayed wrapped together until we began to fall asleep. Alex eventually turned over and I spooned up to her back, she pushed back into me, turned her head around and we kissed good night. As I drifted off to sleep I heard her say softly, 'Chan rak kun, James, I love you.' The day dawned as most do in Koh Samui with bright sunshine. A...

Lucid

by alias_the_archangel on May 15, 2018
Fetish

I always found that I had my most lucid dreams during Spring and Autumn, when the temperature was just right for snuggling up in the covers. Most of the time, when I was able to recall such a dream after waking, I could only piece together bits and pieces of what transpired. That was definitely not the case when it came to the events that changed my life for...