Cross Dresser Stories

60,464 results
Orientation
Length
Source
Infinite Scroll

Jay Cross

by JayCross on Sep 14, 2017
Transsexuals & Crossdressers

It was getting dark outside. I sat on my bed reading my favorite magazine, waiting. The sunset ment it was getting closer for my mother to go to work. I walked out of my room and looked down the stair case. I can see her getting her purse ready. I was already done with all of my homework and was ready for a little fun. "Jay, honey I'm leaving" "Ok mom, I'...

The Roommate

by ValoryG on Sep 14, 2017
Transsexuals & Crossdressers

Josh preferred living alone but since he switched to teaching part-time (so he could write the great American novel), he could no longer afford his apartment's rent. He had relished being able to walk around half naked, watch what TV shows he wanted, let the dirty dishes build up, keep whatever hours he wanted and be a slob. That was going to change, he real...

Unmentionable

by Bellatrixie on Sep 18, 2017
Text With Audio

* * * * * Click Here to listen. (20.5 min/mp3) * * * * * You have come into my house to design new furniture for the master bedroom. You are an artisan and have been taking measurements and making notes of the contours of my bedroom as your minds eye envisions the end result of your labours. You think I have gone downstairs to run the laundry and so you...

Lisa, A Story From A Male Admirer

by RubberBudcus on Sep 16, 2017
Transsexuals & Crossdressers

This story is based on the truth and real people. It all started in a routine sort of a way. Well, routine in a Literotica sort of way really! Let me explain. I am a lifetime fetishist. Male, 63, heavy build and hairy to gorilla standard. I experimented at an early age with wet clothing and kept at that converting to female attire through two marriages, tw...

Interactive Crossdresser...Dare Me

by PorscheKaru on Sep 16, 2017
Transsexuals & Crossdressers

In here my name is Porsche and my other name you'll never know. I have two bedrooms in my condo, in one I am the normal man of the house however down the hallway I am in Porsche's bedroom. In Porsche's bedroom I wear sexy thongs and boyshort panties, matching bras and always garter belts with sexy thigh high nylons and stockings. I have a 36d chest, 30 waist...

A New Adventure...

by johnjinglez1 on May 16, 2018
Transsexuals & Crossdressers

I saw someone begin a "diary" of their experiences as a sissy on here recently and it inspired me to give it a shot myself. The following will be true stories from my past starting from the first time I ever hooked up with a Tranny / Cross dresser / Sissy. First things first, I consider myself to be a straight male; despite having had sex with all of the a...

Stepping Out

by hydrangealawrence on Aug 27, 2019
BDSM

Jackson pulls into the driveway and turns the engine off. He kisses my hand in the darkness. "There's a bottle of Shiraz inside with our name on it," he says. "Sounds delish." We step out of the Audi and go up the stone path to the house. All the lights are off. Jackson unlocks the door and holds it open for me. I look around at the hardwood floors and...

How to Just Get More Kinky

by Decayed Angel on Dec 12, 2018
How To

Sex, isn't it grand? Especially considering the amazing wide variety of persons, places and things there are out there to fuel our sexual appetites. Considering the many odd fetishes and sexual practices that people indulge in or fantasize about, erotic writers have a rich fertile place to look for story ideas. Of course this rich fertile place for story...

Chance Encounters Ch. 01

by KuriousGrl74 on Sep 14, 2017
NonHuman

When the phone rings, I am hesitant to pick it up, letting it ring five times before I find the receiver in my hand. On the other end, the same quiet breathing echoes in my ear before the familiar voice whispers, "Tonight." Then ... the click on the other end and the hum of a dead phone. I close my eyes, holding the receiver intimately, lulled by the constan...

Kayla Caught Me Ch. 01

by lulu_dools on May 1, 2018
Transsexuals & Crossdressers

Hello there. Let me tell you what happens when you get caught... You see I am a cross dresser when I get time and have lots and lots of clothes and lingerie to play with. I keep all my female stuff in the computer room where no one ever gets to go. I am 40 years old with long curly brown hair and brown eyes. I weigh about 80kgs and am 5ft 8inches tall. I l...