Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

Hostess with the Mostest Ch. 10

by MicheleNylons on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten -- The Hostess With The Mostest "I don't care if there's a fucking flying saucer from Mars down there; I just want some sleep," Candi replied and Millie giggled as the Skyliner made its approach into Changi airport, Singapore. The flight deck crew and the first class hostesses were rushed through customs and immigration and bussed away to a fiv...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Sissy Perfection

by cornthuxton on Dec 23, 2019
Transgender & Crossdressers

Hello. I had done just about everything there was to do mature, lesbians, trannies. And several times each variety. So I thought it was time for a twink. As with my previous adventures Hong Kong was my hunting ground. Two, week long trips a year made it easy for me to indulge me desires. I guess I am pan sexual...whatever that means. I'm open to lots of...

CD Asst. Secy. Ch. 02: Continued

by cdtycoon on Apr 22, 2020
Transgender & Crossdressers

All the characters in the story are above 18 years of age. So, just sit and enjoy the story. Then, after pulling up our panties and readjusting our skirts, we sat down, back in the chairs & inserted the earpiece; which had a speaker & mic. and was about 1 cm. so it easily got fit inside our ear. After fitting the earpiece, she again started explaining fur...

Becoming Jessica Pt. 03

by Lovely_Jessica on Sep 25, 2017
Transsexuals & Crossdressers

To recap: I came out to my wife Emma yesterday that I was a crossdresser and was considering transitioning into a woman. After some initial grief she became supportive and helped me fully dress as a woman for the first time. We even went on an impromptu 'girls night out' at a piano bar in a local hotel/resort in suburban Chicago where I met a man named Drake...

The Marriage of Martin Hastings Ch. 14

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin walked down the walkway his heels clicking loudly as he moved quickly away from the house. He felt almost naked walking in the bikini that Leanne had seen fit for him to wear out today. Wearing 6" spiked heel sandals and his hair in curlers covered with a large white scarf tied under his chin, he walked with his head slightly bowed as he thought about...

Teen is Forced to Crossdress

by fun4all6969 on Sep 18, 2017
Transsexuals & Crossdressers

My first time with another man was when I was 18 back in the late 80's. My girlfriend was a virgin and the farthest we went was kissing and rubbing together with our clothes on. I would take my dirty magazines out behind where we lived in the woods and take off all my clothes and masturbate. I was out there every day there was nice weather masturbating and...

Becoming Cassie Ch. 01

by TGJamie on Sep 25, 2017
Transsexuals & Crossdressers

Money was hard to come by in our household. Being the oldest of four and my mom being a single mom put a real strain on our resources. Rarely did we ever have any extra money in our family to spend on things like eating out at a restaurant or going to the movies. If we wanted to do that, we had to save our own money to do it. Things were just tight. That sai...

Alex

by WhiskeyIsGood on Jan 15, 2019
Transgender & Crossdressers

Meant for this to be out before New Year's Eve but, it didn't work out that way. I apologize for that. Anyway, this is not meant to be a big story or anything fancy, just a little something I worked up over the holidays. I apologize in advance for any spelling or grammar issues...I use a program to edit my work but, it does not always fix everything that I n...

Frolicking on the Fifth Ch. 02

by Entrammeleur on Jan 22, 2020
Transgender & Crossdressers

This story follows the events of "Unleashed By Nair" and "Boned on the Fourth of July." *** After dancing on my driveway in my wife's off-shoulder mini peasant dress, I needed a drink. I sipped Gatorade through a straw to avoid messing up my lipstick, and leafed through the local paper while pondering my next outfit. An item near the automotive ads caugh...