Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Blushing Bride Ch. 06

by britneyfan on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Six: Wedding Presents I was on an incredible high for a couple of days after my wedding. Like many bridegrooms on the day, I had felt very nervous, both about the day itself and the years of married life that stretched out before me. Only, I had a little more to be nervous about than many. It wasn't just my bride-to-be's contrasting virginal Catholi...

A Latex Trap

by Lifeinlingerie on Sep 21, 2020
Fetish

I had been perfectly set up. All the pieces fell into place, and I followed each part of their plan as if I'd had step by step instructions - all leading me to my current predicament. To set the scene... I am currently tied to a soft, red-leather covered bench. My knees, thighs, and arms are bound and clipped to the frame of the bench. I'm wearing a bright...

Made to Obey Ch. 06

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Sleeping Beauties Ch. 06

by MicheleNylons on Dec 10, 2019
Transgender & Crossdressers

Chapter Six - You didn't accidentally fuck her did you? After his fight with Penelope, Bradley Wilson had gone back to his hotel and had a fitful night's sleep. As directed, he put on his best Brooks Brothers navy-blue suit and crisp white shirt. He wore a blue silk tie and highly polished black shoes. He left the hotel at seven o'clock to make the eight...

Tiffany's Deal Ch. 01

by MicheleNylons on Jun 24, 2019
Transgender & Crossdressers

Chapter One -- The Deal Author's note: I know very little about playing poker. I have played blackjack in a few casinos in the USA, Australia, Europe, UK, even Vanuatu but that's the sum of my experience with gambling. Blame any factual errors squarely on me rather than my researchers, Google and Netflix xxx Michele Tiffany was not the name on her birth ce...

Made to Obey Ch. 05

by madetoobey on Jul 2, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

Creating Ginger Ch. 09

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. ~~~~~~~~~~~~~~~~~ To say ginger was in hell would be an understatement, although it would be more accur...

Creating Ginger Ch. 07

by Ms_Allison on Aug 31, 2020
Transgender & Crossdressers

Author's note: This is a story of a loving, married couple who wanted to expand their boundaries. It involves crossdressing, gender play and their foray into dominance and submission. If these are not topics you are interested in, then please move along. Hopefully you've read the previous chapters to understand the nuances of this storyline. ~~~~~~~~~~~~~~~...

Submitting to Dominance Ch. 01

by _pdy_ on Sep 28, 2020
Transgender & Crossdressers

Warning: this chapter does not include explicit sex. That will come in later chapters. Instead this first chapter is meant to chronicle the beginning of Perry's descent to submission. It's meant as a setup chapter and will lay the ground work for what is to be a story of how she is taken from unsuspecting young man to insatiable crossdressing, sissy slut. Ho...

Forced Entry

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world. Danny was a large man in his forties and was running to fat. He was dressed in a travel-weary navy-blue business suit, a crumpled white shirt now open...