Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

Pins Ch. 04

by Reefkeeper on Sep 13, 2017
Erotic Couplings

PINS I'd gone back and forth quite a few times in my head on the issue. While I'd originally thought Bianca's impending gangbang shoot would scare my cousin Ashley away from ever considering stepping in front of a camera, the opposing point of view held that after seeing something so totally outside her experience, anything of lesser intensity might be cons...

Carla Becomes A Nude Model Ch. 03

by Photman on Sep 25, 2017
Exhibitionist & Voyeur

My name is Joe and this is part three of a true story that happened within the last two years. It is the story of my wife's, Carla's, photo shoot with Bradley. Bradley is an artist commissioned by a French collector, Stephane, to take photos of a bold, beautiful American woman and then do sketches and oil paintings of her. A week before the cocktail party a...

The Seamstress Ch. 01

by L O Reins on Sep 19, 2017
Exhibitionist & Voyeur

Souvlaki, The Hamburger of Greece. "Stand nice and straight, Mr. Kotukus. I need to get your inseam." "Uhhh, Yes Ma'am, like this? Carl stood straighter and separated his feet a little more. Vivian held the end of the fabric tape loosely in her left hand. She was kneeling behind the young man standing in front of her on the raised platform. She peeked a...

Sylvia's Next Door Affairs

by Cleevedreams on Dec 30, 2019
Mature

The affair with Sylvia began in the week before Christmas. Sylvia was just forty. I and Janet were both fifty one, and had lived next door since just after Sylvia's husband had passed away two years ago. When we moved in I had noticed how attractive she was, how could any red blooded male not notice her shapely ass, and well proportioned tits. Her red ha...

First Date

by daddybear_ on May 15, 2019
BDSM

Chapter 1 Daddy is staring at Jessica across the breakfast table, watching how she's lining up the pieces of toast. Jasper the bear is sat on the table next to her watching the precise way she eats through the food in front of her. Daddy chuckles as she gets down to the last two pieces and stops to work out which one to eat first. "Why are you laughing Da...

Vinyl Groupie Surprise

by shinymagicbeauty on Oct 6, 2020
Fetish

Vinyl Groupie Surprise "Thank you London, good night! See you next time!" "Whew," thought Mike to himself. "Another show in the books, and this one didn't go half bad." He'd been on tour for about a month now, pumping out his patented brand of retro-electro keyboard indie pop, and for the most part, it had been going well. His latest album, Dive Into the H...

Hell in Heels

by westerntiger on Sep 13, 2017
Erotic Couplings

Hell In Heels. (A Dylan James Adventure) These are all of the "Dylan Joins The Band" series put together. Several of my really nice fans had asked me to do this -- so this is for them. The text has been cleaned up a little, and there are some small changes. Hope you enjoy! These are the continuing adventures of Dylan James, Hollywood stuntman and stud. Dyl...

A Mage's Tale Ch. 16

by NeoShade on Dec 8, 2017
Sci-Fi & Fantasy

I groan awake with a pounding in my head. I open my eyes timidly. They really do care about me, the blinds are drawn. Nix is lying in the bed with me and Oasis is quietly moving around in front of the stove. Nix locks eyes with me, a questioning look in her eyes. Leaning back I grown wincing from the herd of mammoths stomping the inside of my skull. "Was it...

Angel's Loophole

by HusbandsWhoShareCare on Feb 4, 2020
Loving Wives

As high school sweet hearts married at 18, my wife and I had never been with anyone sexually other than each other. This never seemed to bother her. And it surely didnt bother me as my wife was an absolute knockout at the time (still is to be fair). 5'6", 36C, Blonde hair, with larger than average blue eyes. 113lbs. any weight she did have was in her ass. Sh...

Flatmates: 21st Birthday Surprise

by milfocker on Sep 12, 2017
Group Sex

It was my 21st birthday and I was on my way to my fiancée's flat in London, where she went to university. She shared it with two of her friends, Diane and Rachel, Diane was short, attractive and slim with olive skin, Rachel however was tall and skinny, but still reasonably attractive. My fiancée's best friend however was Suzie, who was on the same course as...