Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Jessica Ch. 02 - Vanessa

by Floydman1 on Dec 16, 2019
Transgender & Crossdressers

Her name was Vanessa. She was very cute, about 5'4", slim, with big brown eyes and skin that was very clear and smooth. We had met online, of course. She had reached out to me for advice and friendship, as I was an experienced transwoman. After talking online first and then over the phone, we met in person. It was at her place, since she wasn't all the way...

Julia, Ben and Lisa Ch. 01

by chloejacobs83 on Feb 10, 2020
Transgender & Crossdressers

A few quick notes: 1. this is the first chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned chloe *** MONDAY I was sitting in Julia's back yard as the evening sun faded, the t...

Crossdressing Days 02: Annual Day

by cdtycoon on Mar 17, 2020
Transgender & Crossdressers

All the characters in this story are above 18 years of age. Also, this is the second story from the series, so for better grasping, you may like to read the earlier one first, but anyway it is an independent story so let us start with it. ---------------- Again it all begins with an announcement for annual day drama or dance participation, which was due in...

The Club Pt. 01

by Paulateevee on Jul 13, 2020
Transgender & Crossdressers

This is a continuation of 'The Trap'. It would be best to read that story (5 parts) first before reading this one although I will try to make this story as stand alone as I can. Background - Paul has been outed as a cock sucking sissy to his friends, family and work. He's lost his job, his wife and friends. Louise offers him a way out. Usual disclaimer. An...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

Pleasures of Life

by InnocentMissLittle on Sep 12, 2017
Exhibitionist & Voyeur

The convention was insane, I had never seen anything like it. Pleasures Of Life wasn't your average convention with a few stalls with chocolates and free massages, or coaches telling you how to enjoy life. Pleasures Of Life was out of proportions. There was over a hundred meeting rooms and auditoriums in the congress and exhibition center, and it was placed...

Whores And Pimps Ch. 04

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

(Warning -- Contains Incest) * Michele lay on the bed sated; splashes of semen glistened on her stockings, blouse, face and hair. Steve, Joe and Bill stood around the bed looking at her, their erections slowly subsiding. She looked across the room and saw that Ellie had returned to administering to the fat cop's needs. She was on her knees and her pretty...

A Murder Misstery Finis

by thrillerauthor on Sep 19, 2017
Transsexuals & Crossdressers

For those who came in late, Matt McCoy -- now Madeline Moreau -- is on the run for a crime he did not commit, and a murder which she did....as the saga concludes, Maddy vows to end her life on the lam. By the author of The Jessica Project "Jacques, when I saw Dr. Villiers, the name I gave him was Madison Monroe. Do you think we can trust him not to talk to...

Damsel in Distress (5 & 6)

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Imagine your sister asking you to chaperone her on a date. Would you? Debatable - Now suppose you had to dress as her girlfriend? Duncan did but it was his sister who came to his rescue when subjected to a humiliating ordeal. This story can be misleading. It starts as an endearing sister, brother crossdressing scenario that develops into a humiliating and b...

Damsel In Distress (3 & 4)

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Imagine your sister asking you to chaperone her on a date. Would you? Debatable - Now suppose you had to dress as her girlfriend? Duncan did but it was his sister who came to his rescue when subjected to a humiliating ordeal. This story can be misleading. It starts as an endearing sister, brother crossdressing scenario that develops into a humiliating and b...