Crossdressing Aunt Stories

13,440 results
Orientation
Length
Source
Infinite Scroll

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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Interracial Extravaganza

by Yelawolf on Nov 26, 2018
Interracial

All stories in here should be about people of different races, anything else goes, you may have a single couples or contain multiple partners as long as one is of a different race to the rest. Human, Monster or Furries will be allowed if you want to start a story concerning them. Remember; all stories contained in here are fiction and the author does not con...

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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...

Best Camping Trip Ever Ch. 04

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a work of fiction. Most of my stories are true, but I do have unrealized fantasies...that I'll try to make reality...hope you enjoy!* *Note-this is part four of my story entitled 'Best camping trip ever for CD'...if you haven't read the first three parts, or at least part two and three, you won't understand what's going on at first. I don't like to...

Stacy and Matt

by mattpantyhose on Jan 28, 2020
Fetish

Matt's bliss ended almost as soon as it had begun. The girl he had met and who not only was pretty and smart, but also enjoyed his crossdressing decided that career was her priority after merely few weeks of their relationship; the two broke up as she moved to a different distant city. Matt still had a good job, amazing boss and sympathetic co-workers, but d...

Sissy Slut Boy

by SissyBoiToi1 on Jan 2, 2017
Fetish

You wake up in your bed, in your attic bedroom. You sigh, not wanting to get out of bed. But then, you realize 2 things--one, your alarm clock didn't go off, you overslept! You have 5 minutes to get to the bus! And two--your bed is soaked in warm, smelly liquid. Did you wet yourself? (Just a note: The "catch the bus" route leads to diaper-related c...

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Mistress Mariegolds Academy

by Heinrich12345 on Dec 25, 2019
Transsexual

The Academy was founded and is still leadet by Maria Mariegold. With a lot of hard work and pasion she managed to make the Acadamy to one of the most prestigious schools in the whole Empire. Today some of the most influential Families send their kids to this fecilety to become influential Futanari or a great cocksucer for some high class Futanari. Over the l...

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Caught en Femme

by RisqueRavisher on Sep 12, 2017
Transsexuals & Crossdressers

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx ***** "I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out wi...

Secret Lives Pt. 02

by WildDaisy85 on Dec 16, 2017
Transsexuals & Crossdressers

This is a continuation to Secret Lives Pt 1. I highly suggest reading that first as it sets the stage for this. As requested by a reader on Pt 1, I have combined two chapters into this one to provide more length. I appreciate the feedback and please keep it coming. *********** I laid in my bed, dressed in women's lingerie and completely bound, as my siste...