Transsexuals & Crossdressers Stories

15,868 results
Orientation
Length
Source
Infinite Scroll

Riley and Julie Ch. 02: Exploration

by AimeeDaze on Feb 7, 2018
Transsexuals & Crossdressers

I franticly waved my hands, trying to speed up the drying process of the deep red coloured nail varnish I had just finished applying. I had been late leaving work and had rushed home to get ready for when Julie would arrive for the weekend, the usual quiet Friday proving instead to be busy and making me fret a bit as I wanted to make sure she returned to Ril...

My One True Love Ch. 11: Epilogue

by f1dude_lotus on Feb 5, 2018
Transsexuals & Crossdressers

Well, I can't believe it's just been over a year since I last posted! Apologies to all for my absence. I do have a few stories in the works; one of them is in the same lines as MOTL - but longer, and then I have a few shorter stories as well. Would love to hear (well read) feedback. As always, any characters depicted here in any sexual acts are over the age...

Seduced and Hoodwinked Ch. 06

by walterio on Jan 14, 2018
Transsexuals & Crossdressers

Darin woke up on Sunday morning alone in bed. It was early and the others were still sleeping. He took his morning piss and then crawled back in bed. As he had done the night before, he contemplated his current situation. He was very content with things at the moment but he would continually re-evaluate it again the coming days. He still had no interest in d...

Biker Bitch Ch. 02

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter Two: Caught With Consequences Cameron Rivers' first memory of feeling different to everyone else was when he was eight years old. The other boys liked to play with bikes and toy trucks and toy cars but he much preferred his younger sister's Barbie. But even then he was smart enough not to say so. He used the excuse that he had to play with her becau...

How Nathan became Natalie Ch. 01

by saintlycd on Nov 22, 2017
Transsexuals & Crossdressers

My name is Natalie but that was not the name I was born with; rather it's the name my wife gave me when she made me her "sister" and her cuckold sissy not long after we were married. My real name is Nathan but that's a name I would prefer never to use again because I enjoy being Natalie much more than I ever enjoyed being Nathan. This is a story of how my wi...

Recruiting of a Sissy Maid Ch. 03

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Three: Training Done, Chantel is On Her Way. Waking up back in her cell, Chantel finds that her days being trained, orientated and broken off will here with the Burrows brothers are wrapping up. Mitch enters her cell and has her come back out and back into the house with him and Nate. Mitch says, "Well Chantel, time has come for us to part our ways...

Cockatoo Pt. 36

by nikkiesilk on Oct 3, 2017
Transsexuals & Crossdressers

Nin was chattering away in the tuk-tuk back to our hotel, but I didn't feel like talking much. I was too exhausted from what had happened with Nancy and Joe to be very talkative. I was simply aching for sleep. Back inside the apartment, Nin fished a bundle of notes from her bag. 'Half for you, Jamie.' She held out a fistful of Dollar bills. 'Nin, you keep...

Riley and Julie: Discovery

by AimeeDaze on Oct 10, 2017
Transsexuals & Crossdressers

The doorbell rang and I froze. I was halfway to the kitchen, empty wine glass in hand, teetering tipsy drunk in my heels and I stopped so fast I almost fell over. It was late at night and I wasn't expecting anyone. If I was I wouldn't have slipped into these clothes when I got home from work. You see during the week, or at least the 9 to 5, I'm a boring, mil...

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....

The Game Ch. 02

by MicheleNylons on Jan 22, 2019
Transgender & Crossdressers

Chapter Two - Petra Returns 21 September 2007 David had showered and dressed while his daughter Rachael lay sleeping and then waited impatiently for the nanny to arrive. He'd drank too much coffee and stole another two elicit cigarettes and was feeling a little high as well as anxious and preoccupied. Who was the Quizmaster and why were they blackmailing...