Chastity Cross Dressing Stories

77,281 results
Orientation
Length
Source
Infinite Scroll

My Initiation

by lockedupslut on Sep 13, 2017
Transsexuals & Crossdressers

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.) * I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a ma...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Black Cuckold into Black Femdom

by Samuelx on Oct 29, 2018
Group Sex

What's good, boo? My government name is Josephine Ajoku, and I'm originally from Port Harcourt, Nigeria. I came to Canada a long time ago as an international student, majoring in Computer Science at the University of Ottawa, and opted to stay after I got my permanent residence. I also remade myself from prim and proper, church-going Nigerian gal into a full-...

His Sissy Bitch Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"You've come a long way, baby." He smiles at me, watches me as I cross my legs. I'm sitting across from him. I can tell the effect I have on him, every time he visits, sees me dressed fem for him, he's hard, rock hard when I meet him at the door. And I know what outfits turn him on the most. I know he fantasizes about me when he's fucking his wife. She doesn...

The Perfect Pair Pt. 10

by ChangeYourPassword on Sep 14, 2020
Fetish

The Perfect Pair, Chapter 10 (fetish, chastity, consensual, cross dressing, anal) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this...

The Perfect Pair Pt. 03

by ChangeYourPassword on Jul 6, 2020
Fetish

The Perfect Pair, Chapter 3 (fetish, chastity, consensual, cross dressing) By ChangeYourPassword Author's Note: This is a work of fiction. It is a story of sexual fantasies and fetishes. These sexual practices are not for everyone, but those of us who delve into them understand the allure. The characters in the story certainly do. If you enjoy this story...

Little Red Riding Hood

by asian_princess on Sep 13, 2017
Reviews & Essays

Little girl, little girl In your cloak of scarlet red Do you mean to raise the desire in my eyes? Little girl, little girl. What little seductive thoughts Do you hide behind that seemingly innocent guise? Little girl, little girl Do you know the things you do. Through darkened woods, as you skip alone Little girl little girl, Do you see me in the s...

Mandy's Reward

by sissymaidrose on Sep 12, 2017
Transsexuals & Crossdressers

There was a sharp, heavy rap at the door. Mandy scrambled out of bed as Mistress Charlotte pushed the door open, hastily smoothing the tiny, soft, pink and green nightdress that barely went past her hips and surreptitiously tugged the matching knickers down from where they had ridden up into her bottom. As Mistress sashayed past to the throne like chair in t...

Lanceolina and Guinevar

by dantemendoza on Sep 1, 2017
Humor & Satire

6th Century A.D. Legend tells of the great Queen Arthuria who pulled, tugged, and yanked the great wizard Merlin's long sword out of his rocks proclaiming her as the first female monarch of England. Uniting all the neighboring borders into one huge kingdom, which she aptly named Cameltoe, Arthuria created the historical Knights of the Oblong Table. She ori...

Decent into Debauchery Pt. 01

by LucidlyConfused on Sep 12, 2017
Exhibitionist & Voyeur

Edited by Slavegirl70 ***** I woke up early for a run in the crisp air before the sun came up; it was the only way I could clear my head. I got dressed in a pair of tight shorts that were a bit small and a sports bra. Sure, the outfit was a bit revealing, but it was four thirty in the morning—who was up besides me? I began to stretch in the front yard as...