Crossdresser Sex Stories

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Unexpected Delivery

by Spindizzy on Aug 21, 2017
Fantasy

You wake up to the early morning sun shining through your Venetian blinds, directly into your eyes. You throw off your blankets, open your closet door, and dig through the clothes on the floor. Searching until you find your least pair of dirty pants. You get dressed not bothering to change your boxers and head into the kitchen through the eerie silence of th...

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Dad My First Lover Pt. 01

by sarahchica96 on Sep 16, 2017
Transsexuals & Crossdressers

Introduction I'm Sarah a 20 y/o closet Bisexual crossdresser, 5ft 6 , slender body I achieved by working out a bit. I love dressing up in short skirts, dresses, heels, typical lingerie and I have a fetish for the Naughty Secretary look. Main story starts here I had come back home from college for the winter holidays. It was just dad and me at home since...

My Brother, My Sister Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

I wrote this story originally under the title "Be Careful In the Park" about an older crossdresser who meets a street gang in a park and gets more than she bargained for. There was no incest in the original version. I like this version better as it includes all my peccadillos: incest, crossdressing, nylon fetish, and forced sex. A warning to those who find t...

Secret Journey Ch. 02

by DrGonzo124 on Feb 11, 2019
Transgender & Crossdressers

AN: with profound thanks to Personal Deviant. 8 9 8 Suki dreamed of another time and place. A place filled with warriors drinking... feasting...fucking. Another body? His, yet not his own, to judge by the nipple clamps pinching him with a painfully arousing agony and the odd sensation along the length of his erect shaft that had to be a lattice of pie...

Gender Change: Magic Closet

by Zekar on Jan 26, 2017
Fantasy

There is magic in the world. Narnia was just the tip of the iceberg when it comes to the magic that a wardrobe or closet can do. You find yourself directly in the crosshairs of such a magical encounter. Whether malicious or benevolent, that is up to you... This is merely the introduction to a much more interesting tale. (Dear reader, if you like this story a...

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Crossdresser Evolution Ch. 06

by pantyhigh on Aug 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's panties. Recap - Crossdresser Evolution - Ch 02 - Getting my wi...

A Day at the Beach

by Danielle987 on Sep 16, 2017
Transsexuals & Crossdressers

Bit of background to understand the context. I am Danielle, I am 18, very petite 5" 8 65kg and have long blonde hair. I have been a crossdresser since I was 12. Australia, it was the middle of summer as I was driving to my friend Kate's house. We had planned to go to the beach as I became more brave in my crossdressing adventures. Kate was the same age as...

the corporation

by davidigor on Oct 21, 2014
Transsexual

you arrive to the building, you've been requested to come here to sign a contract for working here the call didn't give you too much information and you can't remember having asked for a job here... but you need the money so you decided to come here the building is a big one in an important neighbourhood... but strangely, the door is in a small alley in a si...

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CD Gets Fucked while House-Sitting

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story that happened recently. I also recently submitted a four-part, runaway-imagination complete fiction story, hope you enjoyed. For anyone not familiar with me or my stories, here's a brief background. I'm middle age, white, a little overweight (hidden well with the right garments), and a married bisexual crossdresser who LOVES getting scr...

Trapslut

by Alexia Wright on Aug 20, 2015
Fetish

Today is the day. Your erotic crossdressing blog videos have earned you your first practical job as an escort. Being the famous online sissy slut Annie, you used to pay the bills selling your horny pictures and masturbation videos to guys on the Internet. You got out of bed, still in your pink babydoll nightie complete with a baby blue thong and head for the...

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