Crossdressing Stories

1,097 results
Orientation
Length
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Infinite Scroll

Crossdressing Dad Takes on San Fran

by vikkihawe000 on Dec 24, 2019
Transgender & Crossdressers

*A bit different than my other stories, but shares some similarities. Let me know what you think. xx Vi ***** Kelly sat in a parked car in the San Fransisco Airport parking lot waiting for her father, Rod, to emerge from the terminal. Kelly loved her father and was glad he was visiting all the way from England, but she was not looking forward to him spendi...

The Role Players Pt. 07

by hollygurl29 on Aug 7, 2018
Transsexuals & Crossdressers

DISCLAIMER: This is a work of fiction and all characters represented here and in any additional parts of this story are all over the age of 21. This tale involved crossdressing, bdsm & role playing. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. The main characters in this tale are as...

Abby's Tail

by Abby_Hart on Dec 18, 2018
Transgender & Crossdressers

Note from the Author I would like to take a moment to thank everyone that has been reading along with Abby's adventures. All of the comments, and private messages, have been really encouraging. Please don't hesitate to comment or send me a mail. I always try and respond to each of them. This is a stand-alone short story that I wrote several years ago abou...

Becoming Cassie Ch. 11

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

On New Year's Day, I slept late, real late. I was still trying to process the month of December. It was clearly a month I would not forget. I did a lot of daydreaming that day and watched TV with the family. I was pretty zoned out. New Year's Day simply came and went. My cell phone rang early the next day and I was asked to price out 2 different painting j...

Birth of a New Sissy Ch. 01

by AltErik on Sep 18, 2017
Transsexuals & Crossdressers

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains male to male sex, Crossdressing and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I did use myself an...

Birth of a New Sissy Ch. 03

by AltErik on Sep 18, 2017
Transsexuals & Crossdressers

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains male to male & male to female sex, Crossdressing and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I...

Dressed To Please Kate

by jealouscuck on Sep 25, 2017
Transsexuals & Crossdressers

My name is William Michael. I go by Bill. I know, stupid way to start a story. My wife is Caitlyn and goes by Kate most of the time. You will see why I started with names. Kate is thirty and I am thirty-one. We had been married three years when all this started. Kate is a very perky brunette, five-four, about 130 lbs. She has very little body fat and is athl...

Recruiting of a Sissy Maid Ch. 08

by Sissy_Chantel on Oct 15, 2017
Transsexuals & Crossdressers

Chapter Eight: Chantel Moves Up at The Jade Maid Club. Six months now into Chantel's new life as a t-girl maid and slut at The Jade Maid Club has her progressing well. Hormones have aided in her feminization and she has proven to be a very good and docile enslaved sissy girl. Not perfect but impressive to see that Mr. Luftgrin, Mr. Jenkins in reviewing all...

Casey's Submissive Journey Pt. 09

by corduroysissy on Jul 17, 2018
Transsexuals & Crossdressers

A day With Dorothy -- Part One - The Players Casey -- Submissive closet sissyfag with a corduroy fetish, owned by Karen. Karen -- Wife/Mistress to Casey and member of the Lady's Club. Julian - Submissive closet sissyfag owned by Dorothy (Dottie) Dottie -- Wife/Mistress to Julian and member of the Lady's Club. Maxie -- President and founder of the Lady...

Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...