Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

Finishing School For Ladies Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One -- The Beginning Valerie Swindon sat at her desk in her small study grading exam papers. A shadow fell over the opaque glass panel of the door and she looked up at the ornate mantle clock and realised it was time. She arose from her chair and came around to the front of her cluttered desk and unzipped her skirt. She caught it before it pooled...

Kasey's Legs Ch. 06

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

It was no more than fifteen minutes after I finished giving Steve head that Darcy came home. She looked happy to see me dressed and sent me to get her things out of the car. When I got back I told her about my time with Steve, including the plan to make a movie so Steve could get his money back from Bruce. "If you just want to make a movie, just make a movi...

The Roommate from Hell

by dreadknots on Jun 5, 2019
Transgender & Crossdressers

"So what's the catch?" Tom asked. Vi tilted her head, orange eyes glaring at him. "What do you mean by that?" He raised his hand to indicate their surroundings. The kitchen of the apartment was less than ten years old and had appliances that looked like they just walked out of a catalogue. It was clean, there was no deathly racket from a heavily trafficked...

My Name is Raquel Ch. 07

by Raquels_Panties on Mar 16, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. My saga began when I was about five years old. I mostly played with my sister and her friends and they would sometimes dress me up in girl's clothes. When I was 18, I started wearing my sister's panties. My freshman year in college, I acquired my first pair of panties in the dorm laundry room. And I began a colle...

Lady In The House Ch. 05

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

From Part IV Then Eddie looked down at my body and noticed the semen pooled at the front of my panties. My semen! He looked down at his tight belly and saw a slimy stain that was the result of my ejaculate spread there when he had pressed his body against me. I watched the terrible storm brood in his eyes as he reached out and smashed me across the face....

Pillow Talk Ch. 02

by MicheleNylons on Sep 10, 2018
Transsexuals & Crossdressers

Chapter Two -- Tranny 101 Michelle Clooney sat in a booth in a rundown coffee shop near Times Square. The grimy window provided views of go-go bars, sex shops, peep shows and adult theatres, the iconic square had not improved any since it's setting for Midnight Cowboy a few years earlier. Michelle was dressed in red spandex hotpants, a long sleeved purple...

Undercover Angel Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

When Mike Harris stole two point seven million dollars in cash from his employer, he knew that his life had changed forever. It's one thing to steal that amount of money from your bosses' safe; it's quiet another to steal it from a ruthless gangster who is heavily involved in narcotics, prostitution, gambling and murder. Mike was Tony Leonardo's bookkeeper,...

Matt Becomes Mattie Ch. 01

by clarepanties on Sep 11, 2017
Transsexuals & Crossdressers

Part 1 It was 2006, a day in April; I can't remember exactly the first day of the rest of my life begun but begin it certainly did. And for my wife, Joanna, it also meant a massive change. I was back in England from a business trip to Canada, to Vancouver to be precise, and I had been back four days since being over there. It was a business trip but Vanco...

Those Shoes Double Date

by cd_donna on Sep 16, 2017
Transsexuals & Crossdressers

** Getting Ready ** It takes me three days to fully recover from great sex, even if the love session ends in an ideal sex nap like it did with Rex and Jennifer. I put out so much energy on the bed, my mind and body are slow the next day. I felt lucky that we were not able to do a double date with Mike the next evening. The plan was for a week from that nig...

The Book of Dreams

by cddannie18 on Sep 15, 2017
Transsexuals & Crossdressers

So there I was, once again sitting at home on a Friday night! I was convinced I must be the only high school senior without anything to do tonight. And just to top it all off... its Halloween! The biggest party and socializing night of the year. I am such a loser. I have no girlfriend... no social life for that matter, and the one thing I really love to do I...