Halloween Crossdress Stories

5,980 results
Orientation
Length
Source
Infinite Scroll

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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Kasey's Legs Ch. 06

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

It was no more than fifteen minutes after I finished giving Steve head that Darcy came home. She looked happy to see me dressed and sent me to get her things out of the car. When I got back I told her about my time with Steve, including the plan to make a movie so Steve could get his money back from Bruce. "If you just want to make a movie, just make a movi...

Summer at Auntie's

by BimboBarbie on Dec 18, 2017
Transsexual

You stumble off the plane and into the airport with your legs feeling like jelly having been seated for a few hours, heading down to the conveyor belt to collect your suitcase. Watching as a few familiar people you recognize from the flight all come and go, collecting their bags happily and leaving while you remain growing increasingly worried. Eventually it...

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Sex therapist

by qaz on Sep 1, 2016
Miscellaneous

Who do we follow?What's next? A boy A girl What's next? A boy A girl...

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Dream Prom Date

by Zelonkarac on Sep 26, 2017
Science Fiction

It is that time of year again, Prom season. But this year is different, this is the Senior prom that will change everything. Sadly the only thing missing for someone is the actual prom date. Who is the protagonist or victim? (Dear reader, as you read this story please remember that if you like any of the chapters that you read please take a second to click &...

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Forced Crossdressing Stories

by Dayeandknight on Feb 1, 2018
Transsexual

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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Internship

by nimt on Jul 12, 2018
Transsexual

An internship was compulsory as you approach the final year of your high school. The school believes in providing students with the opportunity to gain valuable practical experience by learning from the industry of tomorrow directly. You went for several interviews and only successful candidates get notified. In the events that the none of the companies pick...

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Second life of Emily

by Alexia Wright on Jun 3, 2015
Fetish

I have always wanted to get fucked by another man. Being 5'6" and weighing little over 60 kilos, my effeminite and near hairless body bore no signs of an able bodied alpha male, so i decided to explore my inner girl since my mother and sister are the only people i live with. It started with simple things, like my sister's school clothes, then her under...

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Friends with benefits

by Kashman007 on Jun 27, 2020
Mature

Sam and Andy had been going steady for about a year now and they loved each other deeply. Both felt that they had found their soulmate. This evening they were walking back home after watching a movie with Sam’s friend from childhood, Beth. They turned into an alley that was a shortcut between the Main Street in town and the street where they lived. Although...

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The twisted DM

by Nobody567 on Nov 21, 2019
Fantasy

Authors notes: please like and comment my stuff I desperately desire your feedback and approval. I am new at this and recently redid the intro hope you like it. A being beyond space and time whose goal is to torture, torment, pleasure and change his players in ways that you cannot begin to fathom for his entertainment and pleasure. He sits at multiple tables...

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