Crossdressers Stories

12,121 results
Orientation
Length
Source
Infinite Scroll

A Special Night, Laci's First...

by Sissy_Chantel on Nov 27, 2018
Transgender & Crossdressers

Prologue: My name is Lawrence, I'm a young 40 something widowed white male, living a heterosexual life. However I have my feminine side, her name is Laci and as such I am a transvestite. I have preferred the long classical term of transvestite for a genetic male who dresses in women's clothes. But crossdresser also works as well. As a transvestite in my fu...

Perfection

by ValoryG on Apr 23, 2019
Transgender & Crossdressers

It all starts, innocently enough, when Joanna's looking for a dresser. On one hand, she can just go to a big box furniture retailer and get an inexpensive, functional one that looks decent (and build it, of course). Or, she can browse around online and find a new or used one with a more elegant pedigree. Joanna, by the way, is a very practical, elementary s...

Love Your Readers: Categories

by Tx Tall Tales on Dec 9, 2019
How To

============================ Help Your Readers. Categorized Your Story Correctly. In Love Your Readers, I wrote about things you do to improve the reading experience for your readers. In Love Your Readers: Categories, I'd like to share my ideas on making it easier for the readers to decide to give your stories a read, by placing it in the right category....

Tranny at the Truck Stop

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

The Perils of Pauline -- Trannie at The Truck Stop Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour...

Female Seduces a Shemale

by Tashas Baby on Sep 25, 2017
Transsexuals & Crossdressers

* This story may not be copied or reproduced in any way. This is a story I wrote for my lover.* As you are sitting in your computer chair , chatting online, I walk up behind you and softly massage your arms. I lean around and kiss you on the cheek. You turn your head to see who it is and I kiss you full on the lips. I walk around your chair and sit on your...

Transsexual Treasures

by dirtyjoe69 on Sep 14, 2017
Transsexuals & Crossdressers

My name is Steve and I am a thirty seven year old divorced male. I am considered good looking. I am very tall standing six foot seven and have a good build for my size. My marriage didn't work for many reasons money, being too young were a couple of them but the biggest reason was sex. I wanted it and she didn't. It always seemed to be a chore for her and wh...

A Slut Is Born

by caroletv31 on Sep 16, 2017
Transsexuals & Crossdressers

I've always had a magnetic attraction to slender pointy hi-heel stilettos since way back when. And then these wonderful sensual sexy feelings between my thighs every time I see a young lady strutting and teetering around on these fabulously erotic pointy heels. It all started in the 1950s era. The era "par excellence" for these gorgeous shoes that did so muc...

The Tasting

by IraIrene on Sep 16, 2017
Transsexuals & Crossdressers

"Mmm. You're pretty in frills, sissy. Pink polka dots look good on you, and your lipstick is just so. Lift up your skirt for me, show me the panties you picked out." "Aww, those are too small. Your cock is poking out. Hee! Now turn around and wiggle your cute little tush for me. Good sissy boy. Now get down on your knees." "I suppose you're wondering why w...

A Fantasy

by Sittingwiththedevil189 on Dec 16, 2017
Transsexuals & Crossdressers

I want somebody to worship me, maybe with love or lust. I mainly want the lust right now. This person would wanna kiss me from head to toe and want to please me over and over again. The person would want to savor me; taste me in their mouth for day's to come. I want them to want me so badly they would do just about anything for me to be satisfied. I'd call...

Discovery by Disguise

by jenniferjoannarose on Mar 14, 2018
Transsexuals & Crossdressers

He bent me over and fucked me with a vicious hunger. This was my very first time. This gorgeous hunk of man was popping my gay cherry. He was so big, so very big, that I was afraid he was going to break my ass. I was hurting, but I was nowhere near wanting him to stop. He was bigger than the largest butt plug I had using to train my ass for just a moment as...