Crossdressing Dare Stories

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Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

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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From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

An Intimate Caning?

by deference on Nov 26, 2017
BDSM

An oxymoron is said to exist when two words are used whose meaning does not seem to fit together such as jumbo shrimp or government intelligence. No doubt, the words 'intimate caning' would also fit this definition. However, while a majority would view corporal punishment and domestic discipline as either sadistic or sexually deviant, a minority have found i...

A Night of Surprises

by StephaniePlayland on Oct 16, 2018
Transgender & Crossdressers

Back story. I've been crossdressing for many years. The reasons for it are not really important however, I know I enjoy escaping being me, and getting to be softer, submissive and docile. My friend, Sir caught me crossdressing a long time ago, he has never really cared what I do as he has lots of women. We both enjoy the friendship and no judgements about a...

Crossdressing Stories

by Dayeandknight on Apr 29, 2025

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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Confession Pt. 04

by holukukkar on Apr 17, 2019
Transgender & Crossdressers

We both were lying on the bed naked, when I felt a kick on my back on turning I noticed that Shivani was hitting me, when I asked her "what happened?" Shivani:- We have a long day today. Me:- Means? Shivani:- We will be going to some place and have many things to do. Now sleep and wake up by 11:00 AM and then wake me up by licking me and then we have to g...

The Many Tales of Crossdressing.

by Whiteskorpion on Apr 22, 2025

This story is open to anyone who wants to write a crossdressing story, it doesn't matter if it's an original story or a fanfiction. Please respect Chyoa's rules, so ****, underage sex (younger than 18 years old) and **** **** are not allowed. I would like to keep this story as organized as possible. For example, if you're writing a fanfiction, before you rea...

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Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...