Mature Crossdressing Stories

29,827 results
Orientation
Length
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Infinite Scroll

The World's Trashiest Strip Club Ch. 01

by DickThePimp on May 21, 2019
Celebrities & Fan Fiction

PERVERTED WHITE TRASH DEBAUCHERY... FUN FUCKIN AND FREAKY SHIT... OH HELL YEAH!!... ENJOY PERVERTS STORY : MY MAMA AND I RUNNING THE WORLD'S TRASHIEST STRIP CLUB... IT'S FUN... IT'S FREAKY... IT'S A CUM BLAST... FOLLOW OUR TWISTED PERVERTED ADVENTURES... AND AWAY WE GOOOOOOOO... "500... 600... 700..." "Beth... have you seen James? I need to talk to him."...

Fuck Buddies with Privileges Ch. 10

by Ratamaquee on May 11, 2020
Romance

The Mommy Gene - June 30 Six years after we both graduated from college I ran into Allison Caroll in the mall. While we were only casually acquainted in college, we found out that we had a lot in common now. Namely we are both obsessed with work and career. That was three years ago and at the time Allison was an accountant with aspirations for a career in c...

My Summer Cougar Pt. 13

by storyfella on Apr 13, 2020
Mature

Having a few requests for more in this series I thought I'd give it a go. Hope you enjoy... The weather had taken a turn for the worse. It was still warm but the rain was falling down and when I looked up the forecast it looked like it was in for the day. I gave Annie a call to say it wasn't worth me coming today but of course she had different ideas. She...

Sweet Laura (Black Femdom)

by Dunn81 on Aug 7, 2019
BDSM

Laura was in her senior year of high school and was a slender blonde-haired woman with big boobs and a small ass. She was in the Cheerleader team and had many friends. She was kind of sad it was her last day of school today. She was attractive to both man and woman even straight one. She had that angel face everybody was watching with envy and desire. She kn...

Celia, The Cello, And Cigarettes

by homerdepot on Sep 9, 2019
Mature

Celia, The Cello, and Cigarettes My name is Francis. I teach ballroom dancing. Rock music never turned me on. I could listen to Metallica, Aerosmith, or The Who... It all sounded the same to me. Like noise. I was trained as a classical musician. I played woodwinds -- the flute, clarinet, saxophone, even the bassoon. My father, who played violin, wanted to...

Strip or Take a Walk

by jessanddrew on Nov 18, 2019
Mature

All characters in this story are above the age of eighteen. There is not a person under the age of eighteen that takes part in any sexual activities or even mentioned in a sexual way. *** One morning I was in my office, sipping a cup of tea as I take a little look at surveillance, to make sure everything is fine, when I see something intriguing. Steven, i...

Filming - A Short Story

by WatchedBeth on Nov 18, 2019
Mature

I had been doing very well in my new sales job, selling DVD's and other items from our ever-growing catalogue. But I still found the time to visit Roger and occasionally Trevor for afternoons of fun. Roger contacted me weekly to see if I ever had time to drop in to see him in between my busy schedule. I always had butterflies and a feeling of excitement wh...

Titty Freaks Ch. 01

by DickThePimp on Jan 21, 2020
Celebrities & Fan Fiction

GOD BLESS TITTIES!! Inside of my van... "Damn dude... shove it down her throat. Fuck... that looks good!" My gal pal, Mob Wives star, Drita D'Avanzo says, licking those delectable lips, blowing a huge slutty kiss at me. My dick is being shoved between my girl Oprah Winfrey's huge ebony melons and down her throat. My hand's on the back of her head helpin...

Unleashing Mary's Inner Slut Ch. 01

by ifry on Jan 21, 2020
Loving Wives

It was a new feeling John experienced, sitting there in the exam room with his wife Mary. The plastic surgeon was drawing with what looked like a sharpie pen the lines along which he would be cutting Mary's breasts to reduce them from their current, somewhat droopy 34D breast size to what would become perky, firm C cups. The feel John was experiencing coul...

Wife is Admired During the Virus

by happycouple1 on Jun 15, 2020
Interracial Love

The corona virus was in full effect, and had ruined much of the early part of the summer of 2020. My wife and I were confined to the house, and the pool in the backyard, since we were not able to socialize with family and friends. Wendy was in the yard tanning in a lawn chair and I was upstairs doing some work for the upcoming school year. I knocked on the...