Crossdresser Caught Stories

163,967 results
Orientation
Length
Source
Infinite Scroll

Interactive Crossdresser...Dare Me Ch. 02

by PorscheKaru on Sep 16, 2017
Transsexuals & Crossdressers

Hi Porsche I loved your kinky stories and I think its hot how you let strangers tell you what to do. I would like to hear you do something more humiliating though... Are you ready? I dare you... to dress as a hot woman, very high heels, fishnets, tits on, makeup, but with a very short mini skirt and no panties. I want you to get a dog collar and a lead...

My Second Time

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

I hope you've been enjoying my previous stories thus far. As you know (unless you HAVEN'T read them) my stories are short, true, and to the point, so you may enjoy them that much quicker without reading long drawn out writings. So here is another true story for your enjoyment. This was my second time (well, technically my third, as the first guy fucked me...

Gender Bent Society

by turtlerocker on Sep 26, 2017
Fetish

Welcome to GenericVill! A small town in a world that has the opposite gender norms of our society. Some changes from our society is that it is a matriarchy, Girls are considered more athletic, Boys are considered nicer and more emotional, Boys wear what our world's girls would wear, and vice versa, and most importantly, Boys are submissive while Girls are do...

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My Summer as a Girl Pt. 02

by RightButSexy on Jun 19, 2018
Transsexuals & Crossdressers

I woke up with the sun already climbing into sky. I was in my Aunt Janey's bed, but she wasn't here. Last night we had the craziest internet date for money. The crazy part was that I was dressed like a girl, even though I'm not. I looked down at myself. I was still wearing those trick panties that hid away my package so I'd look more like a girl, but the bu...

Real Life: The RPG

by Katnaace on Nov 25, 2019
Fetish

Having logged in, you get to the biggest question of all - who are you going to play? It's not like this is a big deal. You can just create your character and be on your way.What's next? Danny Hopkins - Dude with a sister Lydia Onava - Widow waking up in an unknown place Claude Rogers - On his way to visit his Aunt Henry Wells - Protesting H20 What's next...

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Gender Change: Woman for a Day

by Zekar on May 1, 2020
Transsexual

Sometimes a man wants to experience what it’s like to be a woman. In this story you will experience a makeover, go on an adventure, and at the end of the day you can go back to your old life. Maybe it’s not for you. Maybe it’s for a friend who you will take on a date. All of this is consensual and in a variety of scenarios. Starting off there are real world,...

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Vacation with Aunt

by Alice Dragonslayer on Mar 19, 2018
Transsexual

Hello, you are 18, semi long black hair, feminine build, shy and submissive. You visit your Aunt Katy (looks like Katy Perry) for the summer. She may or may not have a daughter. She has a very feminine house and has a pink car. She dresses pretty hot. Her breasts are perfect and she's in her 30's. She doesn't have a husband and stays in an apartment with one...

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sissy's life

by cdbaby on Apr 20, 2018
Fetish

INTRODUCTION: (sorry the way it was originally seemed unclear) Sissies, they're all over the world, and beyond. Discover their origins, their fears, their lusts.What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy? What's next? halloween vinny Messaging with a dream Trendsetting slumber pary Are you my Mummy?...

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Brotherly Desires

by fuzzie_writer on Sep 16, 2017
Transsexuals & Crossdressers

James heard the doorbell go, and opened it to find his neighbour standing there with a smile. "Hi James, I'm wondering if I could ask a favour? My broadband's down and I have some urgent emails to send. Would I be able to use your computer for half an hour?" "Sure Dave, come on in and I can help you out!" Dave grinned at him as he squeezed past. James had...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...