Crossdressers Stories

12,121 results
Orientation
Length
Source
Infinite Scroll

Mistress Sylvia Pt. 01

by corduroysissy on Dec 18, 2018
Transgender & Crossdressers

Debbie arrived for his counseling session with his therapist Anne O'Malley at 8 pm. As he sat in the waiting room dressed in his maroon, Laura Ashley, wide-wale corduroy dress he wondered why Anne suddenly wanted him to dress in drag for a session. He was puzzled too by the fact they were meeting at night. That had happened only once before due to an emergen...

The Saree Bet Ch. 03

by piyali19 on Sep 14, 2020
Transgender & Crossdressers

The next morning, I woke up in Saloni's room. I was still wearing the cum stained saree from the previous night. Now that the effects of last night's alcohol were wearing off and reality was setting in, I was full of mixed emotions. I was very happy about dressing up as a woman, but at the same time I was conflicted about what I had done with Pranav... or r...

Fucked: The Interview

by thereshegoes123 on Sep 14, 2020
Transgender & Crossdressers

The camera winked on, and the familiar scene of the influencer's bedroom came up on the screen. A Cheeky grin. Showtime... "Hey guys, I'm Dizzy-Dom and today, we're doing another crazy Q and A!" Dom's carefree blond hair and cherubic features radiated energy. "Today we are joined by a very special guest... Jessica Deluxe!!" Lounging in the chair next...

Girlfriend with Testing Device Ch. 25

by Razmagurk on Mar 16, 2020
Transgender & Crossdressers

Warning, this chapter includes the second person, topless waitresses, ironic reveals, resets, rollbacks, coffee, anger, justice, mercy, vengeance, truth, confrontations, further hard decisions, mysterious benefactors, opportunities, and a bright light shining in from the future. Girlfriend with Testing Device - A Smutty Fanfiction, of Sorts - = Part 25...

The Priestess of the Night - Night 02

by Liver96 on May 12, 2020
Transgender & Crossdressers

Not a big fan of second parts, but as some emailed me for this one, I took the time (very limited with the team season suspended, travel, coronavirus hysteria) to write this one. Will Dogannu survive his second night against Aalyat? We will see it. A new important character joins us, will it change the course of the story? Once again, this isn't intended to...

One for the Team Ch. 02

by MicheleNylons on Jun 1, 2020
Transgender & Crossdressers

Chapter Two - The Inner Sanctum September 1984 Charles lived with the veiled threat made by Robert Fellows that he knew Charles' secret, whatever that meant; but Robert didn't bring it up again over the ensuing days and Charles was just too busy to ruminate over it as the days turned into weeks. Besides the hours he devoted to class and studies, his comp...

One for the Team Ch. 06

by MicheleNylons on Jun 1, 2020
Transgender & Crossdressers

Chapter Six -- Smells Like Poison May 1986 Mrs Frobisher turned out to be a rather attractive forty-something matron who exuded suppressed sexuality with her tight skirt and jacketed business suit, long legs, stiletto heels, red hair and milky-white skin. Detective Sergeant Archie Sanders fell in behind her breathing in her scent, his eyes locked on her Ru...

One for the Team Ch. 01

by MicheleNylons on Jun 1, 2020
Transgender & Crossdressers

Chapter One - Trans Sexcretary Author's note: When I began this story just before Corona Virus changed our lives, it was going to be a short story about forced feminisation. With time on my hands because of the compulsory isolation the story grew and morphed into a love story and finally a 'whodunnit'. I hope you enjoy the twists and turns and please leav...

Red Swallow Ch. 01

by BJGoodhead on Mar 31, 2020
Transgender & Crossdressers

After completing "The Diary of Jewel Delacroix" I was approached via E-mail by Rachael Ricci Swede and asked if I would consider writing a story idea she had. After a few emails I was intrigued by her idea and agreed to write it. This is an original story by Barbara Jean Goodhead. Written in collaboration with Ideas and Plot Points by Rachael Ricci Swede....

Creating Ginger Ch. 02

by Ms_Allison on May 13, 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 cuckoldry ,dominance and submission. If these are not topics you are interested in, then please move along. In the below story I refer to the male character several ways but try to maintain a consisten...