Crossdressing Dare Stories

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An influential Dare

by femboyslut122 on Apr 20, 2015
Fetish

As a college student most of Kyle's time was spent in class or doing work for class. He knew that others found a better balance, or lack thereof, between class work and a social life. Because of this Kyle always looked forward to the last Saturday of each month. He and his friends would get together once a month to catch up and dick around while playing tabl...

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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...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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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...

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...

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...

The Fairer Sex

by PrinceCai on Aug 13, 2020
Fetish

What might the world look like if women were usually stronger and more aggressive than men? Perhaps a society existing very much like the one we know, but with almost every gender role reversed. Not only that, but what if the ideas about the sexes that evolved in such a world were far stricter, enforced through every aspect of society and any deviation looke...

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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...

Crossdressing Confessions Ch. 04

by EvelynWilde on May 13, 2020
Transgender & Crossdressers

I roll over, back under my sheets right after I read her promissory message. I changed back into boxers in a fit of shame after coming home last night. Still the thrill of that night lingers like a lead weight on my chest, making my breathing shallow and constricted. The sensation resurrects the memory of her hand holding me down against the mattress, the sh...