Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Life and Time of Lady Vargos Ch. 09

by rik581 on Mar 26, 2019
Transgender & Crossdressers

Martin walked down the hallway at a brisk pace. Walking with a bit of exaggerated hip movement and fingers out palms down, just in case somebody was monitoring him. He had adapted quickly to walking this way and had found it not too difficult since his daily treadmill walks were done the same way. The walk was cute for others to watch, but Martin felt silly...

Hot Chocolate

by XtinaSmith2017 on Nov 27, 2018
Transgender & Crossdressers

"Booty call." Casey was sat cross-legged on his bed with his laptop open before him when he heard the familiar and teasing cadence of his sisters voice. Surprised by her presence he looked up from his laptop towards his open bedroom door, taking in the sight of his sister stood there, leaning casually on its frame, the hall's lights spilling into his room a...

Wedding Day Surprise

by Quietoldie on Dec 3, 2018
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** You might say I had an unusual childhood. My older sister had wanted Mum to have a girl when she was pregnant with me. She got over her disappointment by treating me like a girl from an early age. She'd dress me up in girly outfits and we would play with dolls. My father had never...

Pillow Talk Ch. 02

by MicheleNylons on Sep 10, 2018
Transsexuals & Crossdressers

Chapter Two -- Tranny 101 Michelle Clooney sat in a booth in a rundown coffee shop near Times Square. The grimy window provided views of go-go bars, sex shops, peep shows and adult theatres, the iconic square had not improved any since it's setting for Midnight Cowboy a few years earlier. Michelle was dressed in red spandex hotpants, a long sleeved purple...

The Punishment

by nat_rose on Sep 11, 2018
Transsexuals & Crossdressers

Fucking fantasy football. I knew there was going to be a punishment for finishing last in our fantasy football league. I didn't know my friends were going to be so extreme about it. Maybe I should've known. Now that we're all 30-somethings, I had seen the punishments escalate over the years. It started innocently enough-we made Greg sign up for and run a 5...

Casey's Submissive Journey Pt. 12

by corduroysissy on Jul 31, 2018
Transsexuals & Crossdressers

Mistress Maxi -- Part 1 Maxine Montgomery was sixty-four years old, five-foot seven-inches tall, and one hundred and forty pounds. She was an attractively handsome woman whose looks and demeanor were very similar to the character Katherine Chancellor on the soap opera The Young and the Restless. "Distinguished" was a very good adjective for Maxine, "arrogan...

Stockings & Stalkings Pt. 02

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Part II - An Unwelcome Visitor When Giselle got home she showered immediately, washing away her makeup and scrubbing at the tops of her thighs where Steve had deposited some of his seed. She had seen the whitish-silvery deposit dried on her legs above her stocking tops, which were also stained with semen. She had half a mind to throw them out as she had...

More Sheer Nylon Fun

by sheerpeter on Aug 18, 2017
Fetish

This story is a continuation of 'First sheer nylon fun' and it takes place in the London suburbs during the late sixties. In that story I befriended a lady called Clare who helped me explore and enjoy my sheer nylon and harem costume fetishes. She borrowed a couple of theatre-quality harem costumes from a professional wardrobe and we had an afternoon of slip...

Joanna's Contribution

by clarepanties on Sep 17, 2017
BDSM

A Contribution from Joanna: (as an adjunct to "Matt becomes Mattie"). * Mattie has asked me to consider writing something for you, the reader, especially about my experiences and feelings as regards the education that I have had from my now friend, Duncan. I am not as emotional as Mattie and tend to write in a more matter of fact style focusing on the ev...

So You Want to be a Nurse? Ch. 06

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six - Retribution 'Dr Stephen Mortlock esq' the card read followed by his phone number and his work address in a suite of offices used by medical specialists. The folded piece of paper attached by a paperclip read: 'Be there at 7PM sharp. He likes the nurse uniform so wear it and get dressed before you go. Go there and back in a hire car; Polly wi...