Crossdressing Dare Stories

42,978 results
Orientation
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Infinite Scroll

A Confession of Mine

by Number23 on Sep 16, 2017
Reviews & Essays

This isn't a story of fantasy or sex. Sorry. This is what the title implies. Never wrote anything before, let alone something of this nature. Here goes nothing. I'm a man of 38. A man who has hidden a part of himself from everyone for a great number of those 38 years. I'm not a writer. Not a man who knows how to put his thoughts to print. At least not in an...

Cruising for a Bruisin' Ch. 01

by komrad1156 on Sep 16, 2017
Transsexuals & Crossdressers

*Note to readers: After writing The Agreement, I had several people email me and ask why I don't go full time. The answer is very simple: I like being a guy. I only want to be a girl part-time. I've never had any interest in being a woman, and any thoughts along that line were completely dispelled after going on a cruise with a former boyfriend. Whenever I...

Feminine Fate Fulfilled

by mattpantyhose on Jun 15, 2020
Transsexual

Like all of my other stories this one had been already published on Literotica. You can find it here: https://www.literotica.com/s/feminine-fate-fulfilled__ For whatever reason Chyoa doesn't include Crossdressing in the category of Transsexual and doesn't have a separate category for that theme. This story does not include any transsexuals, but I considered...

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Hostess with the Mostest Ch. 01

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Author's note: This ten-part story stands on its own but introduces characters from my previous story 'Transvixen'. It is not imperative to read Transvixen first but it will provide better context for those who like continuity. There is plenty of sex for those who like sticky fingers but also a decent plot and character development in my humble opinion. I wi...

The Devil You Know Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours...

Sarah Had to Give a Blowjob

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. ---------------------------- After collage, my girlfriend's best friend, Alison, and I found ourselves working in the same city and...

Caught in Her Panties Ch. 01

by Knightofround on Sep 12, 2017
Transsexuals & Crossdressers

In the past few months I have been curious about myself. I am a straight guy, always have been, but that's not to say I haven't had fantasies about trying something new. A girl I dated when I was 19 years old, I am now 28 years old, was a big freak. She was very dominate and loved forcing herself on me, both in private and public. She would tie me down and p...

Sarah has a Crossdressing Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I love to dress-up as a girl and get naughty with someone who understands the love of dressing as a girl. So I advertised on Craig's List for a crossdressing buddy; someone to play with and get naughty. A guy emailed me and we started exchanging emails and then a couple of phone calls. We discussed what we each liked to do. I love to kiss and cuddle before e...

Bitch

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

'I am ready, Sir.' I texted on my cell phone. 'Room 28.' A few moments later, the cell phone pinged and a return message appeared. 'You know what to do -- I'll be there very soon.' I took a shuddering breath and looked at myself in the bathroom mirror. An angry frown marred the soft made up sissy face looking back at me, framed as it was by dark straight h...

The Bio of a Masturbator

by Chatomana on Sep 18, 2017
Toys & Masturbation

Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital. Prologue This story is not about love, nor about romance, or...