Crossdressing Stories

1,097 results
Orientation
Length
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Infinite Scroll

CD Asst. Secy. Ch. 06.1: Prez.'s Prop.

by cdtycoon on Jun 2, 2020
Transgender & Crossdressers

All the characters in this story are above 18 years of age. Also it is first part of my last story in this series. PRESIDENT'S PROPERTY 9th January 2021, here I am in the presidential suite, on the top floor of the inpatient building of the Lion Fisher Hospital. wearing asst. nurse's uniform riding on our President's(Chairman's) cock, which was the same i...

Couples Only: Glory Hole Night Ch. 04

by married40scouple on Jun 16, 2020
Transgender & Crossdressers

Hi All, You don't need to read the previous chapters to understand what is happening, though it would be nice. Really, though, this chapter is about how two male roommates were invited to a party and how their lives changed after that very special party. I hope you enjoy. Feedback is always exciting and I greatly appreciate all your comments. Please enjoy, v...

The Wolf and the Seven Young Goats

by ViridianLibrarian on Jul 14, 2020
NonHuman

Author's notes: Welcome to my third Fucking Fairytale! I hope you'll like it, and please rate and leave a comment! A warning: while it would've been simple enough to transform this fairytale with just regular crossdressing, this version contains magical transformations and dick-girls, and if that's not your thing, I suggest trying something else. --- Once...

Michele And The Predator Ch. 03

by MicheleNylons on Jul 15, 2020
Transgender & Crossdressers

The Predator was stunned; it dawned upon him what had happened; he had fucked and been fellated by a transvestite. A man dressed as a woman! He looked at the pathetic sight lying before him on the bed and laughed. He thought to himself that she was just as good as any 'real' woman he had fucked; and she sure wasn't going to be telling anybody about this even...

So You Want to be a Nurse? Ch. 01

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Bound to Her Calling Males make up around 10 percent of the nursing workforce in the UK. Nurses are typically regarded as female and males in nursing can find themselves referred to by the public and patients as 'male nurses' or 'murse' to distinguish them from other nurses. After the Second World War, large numbers of male nurses moved into the work force...

The Wedding Ch. 02

by kinglem on Sep 16, 2017
Transsexuals & Crossdressers

Dave and Sarah were expected down the day before the wedding for the rehearsal dinner. It was a long, quiet drive for Dave, Sarah had agreed to go to the wedding but she had not spoken to Colleen since the botched bachelorette party. They chatted briefly at the start of the trip but as they got nearer their destination Dave could see Sarah's nerves take over...

Ladies Night at the Leather Bar Ch. 01

by latecomer91364 on Sep 15, 2017
Transsexuals & Crossdressers

Chloe McGill never led me astray. I was a full time, tax paying citizen of 'Astrayville' long before I met her - I just wasn't that good at it. Then Chloe came along, and that girl would end up getting me into some of the most outrageous adventures. I adore her. It must be made clear how much more she is than just a cohort in gang bangs and sexual trysts of...

Life With Miss Ida Ch. 01

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

Ida and I had been seeing each for about six months and it was all going very well – I was 30 at this point with Ida being only a year younger. Me - a very easy-going young man, fit, lithe and a hundred percent, dedicated cross-dresser! Ida – also young, Italian and with a sexy curvy figure that matched her petite frame very nicely. I was secure in a well-pa...

Obey Thy Neighbor

by jealouscuck on Sep 18, 2018
Transsexuals & Crossdressers

My name is Melvin Johnson. I am an accounting executive for a very large medical conglomerate. I have the luxury of working from my home office a good portion of the time. Not that it is all roses for I travel some and work some long hours out of town. My wife Chelsea is also an accountant. However she travels at least sixty percent of her working time. She...

The Game Ch. 05

by MicheleNylons on Feb 12, 2019
Transgender & Crossdressers

Chapter Five - Edinburgh 21 September 1987 Petra met William at the door to her flat dressed in a black see-through negligee, red satin suspender belt and matching panty and bra set, fully-fashioned black stockings and red high heels. Her makeup was heavy but perfect and she had accessorised with silver costume jewellery and she reeked of Poison, their fa...