Cross Dressing Stories

72,522 results
Orientation
Length
Source
Infinite Scroll

Sissy's First Time

by Sonjas_pet on May 23, 2018
First Time

By the time my wife, S, and I had been married for fifteen years, there was not much that we didn't know about each other. If you're going to make it that long, you're going to have to learn to be honest with each other. This is what had led to me recently, cautiously, come out to her as being bi, turning at once tepid physical relationship into one of ongoi...

Mistress Meets Biker Boy

by glorialamuse on Sep 16, 2017
Transsexuals & Crossdressers

I have been cross-dressing since I was a young teenager trying on my mother's clothing whenever I had the house to myself. I was now out on my own and between relationships. I thought I was a heterosexual male, having only had sex with females. I was not attracted to males at all. All my relationships were with females, several long-term girlfriends included...

Pussy-Licker: The Man Who Loved Vaginas

by tristantrotsky on Jul 13, 2020
Group Sex

The Yorkshire village of Hornsthwaitedale straddles the lazy curve of the river around the old stone bridge where the oak tree bends low beneath the lush weight of its own greenery, and willows ripple shadows up from the shingle riverbank across the cemetery towards the tall spire of the Norman church. Several narrow ginnels and snickets radiate between clus...

Change of Fate

by Neorotoxin on Sep 16, 2017
Transsexuals & Crossdressers

Foolish choices fill most every persons life at least part of the time. Most of these choices are harmless enough, and don't leave much of an effect on our lives. Other times, like this, we make a choice that forever changes our lives... I used to be a normal guy, like many others, at least for the most part. I dated normal women, and did normal things. The...

My New Life Ch. 01

by sissy_traci on Dec 31, 2017
Transsexuals & Crossdressers

My name is Stephen and my wife's name is Veronica. At the time of this story, I was thirty years old and we'd been married for five years out of the eight years we'd been together. Our relationship had begun to change due to the fact I'd kept a secret from her because I didn't want her, or anyone, to be judgmental of me...I'm a cross dresser and have been si...

00063 An MtF with a Bi Wife Ch. 01

by Tarbut on Dec 25, 2019
Group Sex

Ralph is quite a strange husband: his wife Cora is lesbian, and he has assented to let her have lesbian affairs -- and after several one-night stands, she's settled with a longtime friend named Naomi. Ralph has never meddled with Cora's lesbian relationships, although he sometimes complain that Cora could have more sex with him, and has joined an LGBT assoc...

Something in the Water

by sublocked on Sep 19, 2017
Transsexuals & Crossdressers

The new house was a dream come true and, believe me, we had needed a change; oh, how we had needed a change. Married for seven years, and it was true; there was a seven-year itch, an itch made that much more intolerable by the fact that it was unscratchable. How could you scratch THAT itch when you loved your wife so much that it was unthinkable? Well, obvio...

Biker Boys Replacement

by phoenix196 on Sep 16, 2017
Transsexuals & Crossdressers

This story has been inspired by Glorialamuse's – Mistress meets biker boy story. As a lover of bikes and cross-dressing mistresses I have really enjoyed writing this story and the sequel which I will publish once this one has been approved. *********************************************** Last week I met my old friend Mike for a farewell drink at our favou...

It's a Beautiful Day

by BabyPink on Sep 16, 2017
Transsexuals & Crossdressers

The weekend started off the same as any other for Simon. He threw off his drab male work clothes with alacrity and stepped into the shower. He shaved his face, legs and pubic area as was his custom, then, after turning off the tap, moisturised his legs, stepped into a pair of lacy pink panties and hooked on a matching bra. The feel of the light, soft, femi...

College Dom - Professor Sub Ch. 02

by Kristofe on Sep 19, 2017
BDSM

****** This is a collaboration between myself and unpublaauthor. Each took a role and wrote for that role. I wrote for Jake's point of view and unpublaauthor wrote for Violet's point of view. We hope you enjoy it and will continue to write more. ****** ***** I awoke the next morning and stretched. I could still feel the vibe egg's aftereffects from the n...