Halloween Crossdress Stories

5,980 results
Orientation
Length
Source
Infinite Scroll

Stuck at an All Girls Reform School

by Therock99 on Jul 12, 2018
Fetish

"John Doe to fit in with normal society, you have been sent to a reform school to make sure that your troublemaking ways are dealt with before they get out of hand. As normal failure to go to the pick up point for your school will result in a warrant being issued and a ten year jail sentence will be issued to you. We understand that this may seem unfair...

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Die Mädchenschule für Jungen

by Redboom on Feb 12, 2020
Transsexual

In einem kleinen Café: Verträumt blick Leon in den großen Spiegel auf der anderen Seite des Raumes. Das Spiegelbild zeigt zwei Damen in den Enddreißigern, eine junge Dame Anfang zwanzig und ein hübsches Mädchen gerade achtzehn Jahre alt geworden. Zumindest sieht sie aus wie ein hübsches Mädchen: Eng anliegendes dunkelblaues Chiffonkleid mit locker über die S...

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Princess of Lustria

by Amylili on Feb 7, 2021
Fantasy

The great holy kingdom of Lustria is a large and prosperous nation, freshly victorious of a long lasting war against the forces of the Shadowlands where it set itself as the most powerful force of the northern continent. Its capital Lewdale, was founded centuries ago at the merging point of two large rivers and became a growing center of trades. From his fam...

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A Dirty Little Theory

by bigrusker on Jul 30, 2019
Transgender & Crossdressers

I have a theory. Or maybe I'm just trying to justify how it came about, but for now let's call it a theory and stick with that. Capiche? Excellent. Glad you're on board. Now, as I said, I have a theory, and it goes something like this: if you marry someone that's of a similar size, eventually you end up wearing their clothes. I think most of the time it ha...

Sissy life

by Kaori_chan on Jan 21, 2021
Fetish

So Ive always had this fetish. I love wearing panties. My name is Jake and Im a twin with my sister Jane. Ever since I was young I would sneak into the laundry room and wear my sisters panties. Being twins, we were always around the same size. She always had the cutest underwear. It was pink, frilly, and sometimes had cute designs all over them. My fetish de...

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Caught My Husband...in Lingerie

by TheGenderBender on Sep 16, 2017
Transsexuals & Crossdressers

I had been away on a spa weekend with my girly friends so was going to surprise my husband by arriving home 4 hours early. He had been so happy for me to spend two nights in a luxury spa hotel I had to repay him the favour, and I knew just how to do it. I crept slowly into the house, and by the sounds of it he was upstairs in our bedroom, probably doing som...

Wet Dreams

by TheNextGamer on Jul 15, 2018
Fetish

For two entire weeks, you, John Doe, have researched tirelessly on a place that historians and philosophers have secretly called... The Labyrinth. A special location that links the psyche of every living being on Earth. The place where you can traverse in people's dreams and do whatever you've wished. Out of sheer luck, you've managed to find a way to enter...

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Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Sissy Academy

by Cynthia Sissy on Jan 2, 2019
Transsexual

(feel free to message me about anything! I'd love to hear from my readers :)) The alarm beeps away as you groan at the sound of it. A cool breeze rustles the curtains, letting the sun peek through. Pushing your hair to one side, you check the time. "Oh, it's still early," you say, pushing the sheets away to reveal your blue satin panties and chemis...

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Curse of the Living Clothes

by calx86 on Jan 8, 2020
Fantasy

There are several stories out there involving living clothes but I want to leave this open to allow many collective authors to be as creative as possible. For example, you can write a story about clothes simply coming to life and stripping their wearer, leaving them nude and embarrassed or maybe the living clothes forces someone to wear them and turns them i...

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