Crossdressers Chastity Stories

18,166 results
Orientation
Length
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Infinite Scroll

The Cuckold Ch. 04

by sissyboycamille on Sep 13, 2017
Transsexuals & Crossdressers

I don't know what had gotten into me the night before. I couldn't look my wife in the eye the next morning and it was a relief when she finally went out to go shopping. I stayed at home and thought about what had happened. I had actually sucked another man's cock, what made it worse was I had swallowed his come and done all this in front of my wife. Charles...

Buying Heels

by OpenMouth on Sep 16, 2017
Transsexuals & Crossdressers

I have to know what it feels like to wear heels. I have the house to myself tonight and I'm going to play. I already have panties but want to buy some new ones. My wife bought me a black, frilly thong which I wore for her when we went out one night; I also have a cheap, supermarket pair of sheer black briefs, which have a tiny red bow and a little silver k...

Dorm Floor Bitch v. 06

by GirlyCumslutBoy on Sep 16, 2017
Transsexuals & Crossdressers

It had been almost half a year since I had first dressed like a girl. I loved the feeling of the lovely lacy panties and bras on my bare, shaved skin, and the unmatched erotic feeling of wearing slutty little short miniskirts, tight t-shirts that exposed my taught tummy, and putting on whorish makeup. By now I had relished my slutty alter-ego, Michelle. But...

This Thing Called Life Ch. 06

by noodneighbor on Sep 14, 2017
Transsexuals & Crossdressers

If I had walked into a room and found a man handcuffed to a bed and his ass resting at the edge of the bed with his legs Velcro tied to modified bedposts to keep his ass exposed for easy access I'd ponder a few things but the five large cocked women who entered seemed to take it all in stride. My mistress, a muscular woman with veins popping all over her t...

I'm Every Woman

by xxvicexx on Sep 16, 2017
Transsexuals & Crossdressers

Ever since I was a little boy I've always loved wearing girl's clothes. I remember going through my mother's lingerie drawer and trying on her panties and bras. I loved the way the silky sheer material felt against my body. As I got older I had less opportunities to indulge in my fetish until I got married. When my wife was away or at work I would wear her p...

The Birthday Gift Ch. 02

by BW3 on Sep 14, 2017
Transsexuals & Crossdressers

This story continues the events started in "The Birthday Gift." If you want the full effect you should go back and read part one. If you like it, and this story as well, be sure to vote and leave feedback. The TV standing in front of the bed showed the scene we had watched I don't know how many times. Me- handcuffed, naked, and bent over a table-at the merc...

Gemini Triad Ch. 02

by JordonLynn on Sep 13, 2017
Transsexuals & Crossdressers

Author's explanation of a minor editorial glitch: 3 places in the last chapter (Chapter 1) you will see something like this 1. Please ignore the number and consider what is written inside the brackets to be in italics. Chapter 2 Except for the wide staircases leading up to her apartment and Domino's rooms on the third floor, Solitaire had the second floor...

Kevin's Sordid Surprise

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

I really love the secretary look, and so do loads of my clients. That's why I'm usually pleased as punch when I get asked to turn up dressed for taking dic(k)tation - I've done it on countless occasions, and find it great fun! So much so that, most days, I'd call it money for old rope. But there's always that one time when nothing goes according to plan......

After Gym Class Ch. 03

by alwaysupforu2004 on Sep 12, 2017
Transsexuals & Crossdressers

Previously: In part 1, Candy had learned of Sara's "special secret" as they showered after working out. Later in part 2, they had gone to Candy's house, where playtime continued in Candy's bedroom. ----------- Sara jumped out of bed, and stood at the side of it, looking down at me. I lay back, still enjoying the afterglow. With my fingers, I absently rubbe...

Paradise

by Bodacious1 on Sep 16, 2017
Transsexuals & Crossdressers

After dinner we take a stroll on the beach. Your hair is pulled back and you wear simple gold rings in your ears. The bone structure of your face catches the light in an amazing display of proud beauty. Your pink evening dress reveals and supports your luscious breasts in a way that no man's eyes can avoid. The lovely Thai women sneak glances at you, awed by...