Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Lucy's Revenge Ch. 05

by Cynthia_D on Sep 18, 2017
Transsexuals & Crossdressers

The techies had fun at my expense for the rest of the week and for the most part I was enjoying it. Everyday I was ordered to wear a different set of lingerie under my male clothes to work. Then at some point each day I was ordered to remove my male clothes and give them to my Admin Gayle who would lock them up in her desk till the techies sent her an IM tel...

Girlyboy

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

Sitting there looking at myself in the mirror while I touched up my makeup, I wondered what I'd become. The reflection gazing back at me with emerald green eyes was that of fresh faced young woman, 22 years old, dark blond, wavy shoulder length hair, a wide mouth with full pouty red lips, a strong chin and high forehead. A very good-looking young female, som...

I Am My Daughter's Bitch

by britneyfan on Sep 25, 2017
Transsexuals & Crossdressers

How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story o...

Transformation Ch. 04

by stillconfused on Sep 25, 2017
Transsexuals & Crossdressers

I was just lying back on the bed and enjoying how very good life can be. My wife Cat, Catherine to everyone else but me, and I had been playing our new game for about three months. If you have read the earlier tales you will know that after losing a bet to her I began a new and exciting lifestyle. The feeling of her mouth on me, slowly moving up and down m...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Ms. Rhonda's Finishing School Ch. 02

by hollygurl29 on Aug 20, 2018
Transsexuals & Crossdressers

DISCLAIMER: All characters in this and any additional parts of this story are all over the age of 21. This tale involved crossdressing and BDSM. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. If you choose to read this tale then I thank you in advance for doing so. When you have finish...

Important Business Comes Up Ch. 03

by Emmcee20 on Sep 16, 2017
Transsexuals & Crossdressers

Having gone to Dana's home on the evening he'd been caught out as a crossdresser, Jason explained how his sister had introduced him to going out dressed as a woman resulting in Jason's first sexual encounter with a man. For some years he had gone back to keeping his crossdressing a secret. __________________________________ Well the challenge had been set;...

Becoming Cassie Ch. 10

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

I was awakened when Eric kissed me softly on my cheek. He had been up early and brought me a cup of coffee in bed. I did a nice long stretch and he playfully kissed me on my breasts. "Hun, you really have to get up and shower. It's time to get ready for work." "I know babe, it's just that last night was so wonderful. I really don't want to go to work toda...

Giving My Ass to a Wealthy Stranger

by shyscholar on Sep 11, 2017
Transsexuals & Crossdressers

And just like that, there I was standing in a stranger's kitchen wearing women's clothing waiting nervously to be fucked by a real cock for the very first time. This is crazy, I thought, I can still get out of here. I'd hardly ever even seen another man's cock and certainly never touched one. But I'm about to let a complete stranger bend me over, put his ful...

Tight Spot

by XtinaSmith2017 on Dec 26, 2017
Transsexuals & Crossdressers

Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavour but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way towards the shop as a group, "Aw come on Cody!" one of them jested, "You aren't a...