Mature Crossdressing Stories

29,827 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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Anime ENT

by akikuka on May 16, 2019
Exhibitionist & Voyeur

They always confused people around them of their true genders as their appearance and figure contrast their true physical self regardless of their claim. It doesn't help that most of them wear female clothing to further add our confusion(and our sexuality). They are called Traps, or Tomgirls if you will. Having the beauty that brings girls to shame, these tr...

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The Slut Couple

by kin1041 on Sep 30, 2019
Swinging

The Slut Couple is inspired by the cover art (made by Chromosomefarm from Hentai Foundry). The idea of a slut couple was interesting and I liked the idea of couples getting into sexy situations but coming out of it still together if not a little twisted at the end. Something like borderline netorare and such. So before we begin; who's the couple?What's next?...

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My Neighbor's Submissive Ch. 01

by marissacd on Nov 27, 2018
Transgender & Crossdressers

Chapter 1 - Exposure They moved in next door shortly after we bought our house about five years ago, a nice couple who were a few years older than my wife and me. My name is Michael. I'm twenty-eight years old, white, five-seven, brown hair, blue eyes and a lean build, suitable for cycling, which I do a lot. My wife, is five-four, slim, athletic and blonde....

Lipgloss Dreams Ch. 01

by lipglossdreams on Sep 12, 2017
Transsexuals & Crossdressers

I suppose that my story starts in the same way as a lot of other crossdressing boys with busy real lives: year after year of bottling things up, slowly buying clothes, dressing furtively, shamefully, until things would get too serious with a girl, then - a fearful, hurried purge, a headlong plunge into the cold waters or normalcy. What a deceitful plunge it...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Life and Time of Lady Vargos Ch. 18

by rik581 on May 21, 2019
Transgender & Crossdressers

Chapter 18 "Changes upon Changes" Martin rolled over on his side hugging his pillow trying desperately to fall asleep. Though the curlers that Leanne had tightly wound in his hair for the night were very uncomfortable and trying to position his head to sleep in them was exhausting, it was the events of the day weighed heavily on his mind and kept him awake...

Soft Sissification

by Lying_Smitten on Feb 21, 2019
Fetish

Welcome to the softest sissy story around, but first you need to choose your character. Would you like to play as the Sissy themself, Mike, soon to be known as Mia, a 5'8 man with dark brown skin and black hair, with equally dark brown eyes, and a slightly soft build? Or would you like to play as the Sissy's sweetheart, Kate? A woman of the height of 5'6, wi...

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Halloween Problems

by Haley_Hazel on Oct 22, 2019
Fetish

Your not that old... So it makes sense you'd want to celebrate Halloween still as an adult. The thing is, you don't care about candy, and costumes, and spooky stuff. Nope, not you. YOUR into this holiday for the skimpy outfits, and parties... for the easy woman at those parties who are even better than candy! So as you walk downtown ignoring the kids in thei...

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Escapism: Nightingale

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

I slobber on the thick, veiny cock in front of me. I slurp away like it's an ice-pop on the hottest day of summer. I'm dressed in a red plaid skirt, a white shirt with a matching plaid badge that reads 'head girl', the neckline just low enough to reveal my leopard print bra. The skirt is riding high enough to reveal the matching thong and floral patterned...