Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Witches of Westfield Mall

by Vestiphile on Apr 22, 2019
Fantasy

I was in the Westfield Mall to return a couple shirts that didn't fit me. I knew I should've tried them on, but dress shirts are a massive pain in the ass when you're in a fitting room. All those pins and clips, the cardboard holding the collars and cuffs in place...way too much work. So imagine my surprise when I saw people running or briskly walking out of...

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A day in wonderland

by BadUsername1 on Jun 26, 2015
Fetish

You awaken in a strange room in a haze. Your vision is foggy and you become aware of your body, you feel it dragging as you get up to move. You rub your eyes and your vision clears up. Your first sight is the floor below, its a white and black chess floor pattern. You follow it with your eyes up to the wall, its a regal beautiful pattern, a deep red. Somethi...

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A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

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Barrack Room Betty Ch. 10

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Ten -- Sea Daddies and Sea Mommies Seaman Michael Nyland graduated from Recruit School in March 1974 and was immediately posted to HMS Raleigh to commence training as a Writer; a sailor specialising in pay, personnel matters and administration. He was glad to see the back of HMS Chelmsford; Spike and the three other Leading Recruits had passed out...

CD Stacy's First Adventure

by CDStacy on Sep 18, 2017
Transsexuals & Crossdressers

I've enjoyed crossdressing for most of my life, but it has been only in the past few years that I have discovered that there is a Stacy inside of me, and have allowed myself the joy of complete transformation: clothes, wig, makeup...the full package. Crossdressing has always been an erotic turn-on for me, and even more so when I am dressed up and completely...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Madam Molly Pt. 01

by corduroysissy on Feb 6, 2018
Transsexuals & Crossdressers

It all started in a chat-room, "Closet Sissyboys." Jesse had been spending a lot of time in chat-rooms in the six months following his divorce. He wasn't looking for love, he just liked to drink and have cybersex while jerking off with corduroy. Yes corduroy. Jesse had a corduroy fetish his whole life and now at the age of 36 it was stronger than ever. He...

First Time Blowjob

by MyWhoreWife on Dec 10, 2019
First Time

I'm a man and I love crossdressing. I love the feeling of nylons on my legs and wearing strappy high heel shoes. While wearing them I would wonder what it would be like to suck a COCK in them. Kneeling between a man's legs and sucking his hard and meaty COCK. I started to go to adult cinema's in the downtown area after accidentally discovering their existen...

Dungeon of Bad Ends

by Hacksource on Dec 12, 2020
Fantasy

Introduction. All great stories must start with an introduction. Welcome to the Dungeon of Bad Ends! Here, the harrowing main characters will do everything in their power to escape from the dungeon unscathed, fighting through many, many, wrong turns on the way out! The dungeon is a massive structure, existing in its own time period as it lays right under the...

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Cruising for a Bruisin' Ch. 01

by komrad1156 on Sep 16, 2017
Transsexuals & Crossdressers

*Note to readers: After writing The Agreement, I had several people email me and ask why I don't go full time. The answer is very simple: I like being a guy. I only want to be a girl part-time. I've never had any interest in being a woman, and any thoughts along that line were completely dispelled after going on a cruise with a former boyfriend. Whenever I...