Cross Dressing Stories

72,522 results
Orientation
Length
Source
Infinite Scroll

Black Sissy For Black Dominatrix

by Samuelx on Sep 1, 2017
Group Sex

As a Black mistress, I totally love it when my Black male Sluts dress up for me. Gleefully I slid my strap-on dildo into Reginald/Slut Gina's ass while spanking him and cussing him out like the bitch he is. The big Black dude is now wearing a frilly pink dress, red panties, stockings, and a wig, and his ugly mug is well-made up. Transforming macho Black truc...

Caught

by Geraldine01 on Jul 27, 2020
Transgender & Crossdressers

My name is Geraldine and here is a story of how a friend discovered that I was a secret cross dresser. The experience I am about to tell you about happened when I was about 23. I had been dressing for years and loved how sexy wearing female clothing made me feel. I about 5ft 7 and have a very slim and toned body which I keep in shape by going to the gym and...

Pantyboy Graduates to Crossdressing

by laceypantyboy on Oct 8, 2018
Transgender & Crossdressers Stories

Pantyboy graduates to public cross-dressing. Hello. Let me just say at the outset that I am not gay. I am a hetero man who really likes panties, stockings and pantyhose. I had been wearing them under my boy clothes for years. Some of my girlfriends were disgusted, some were OK with it while not being turned on by it, and a few of my girlfriends did (and do)...

Fetishville (Adding Encouraged)

by VioletWinters on Sep 26, 2017
Fetish

Welcome to Fetishville! I am Violet, the mayor here. I know you're eager to start so let's get to it. To begin with your adventure, press the "Start Game" button on the right and find your fetish. It is pretty straight forward. If your fetish involves dominating, select [Dominant]. If it involves being dominated or being submissive, select [Submiss...

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Hot Sex Instead of Dancing Ch. 18

by SusanJillParker on Sep 16, 2017
Transsexuals & Crossdressers

Please give me the support of your vote. * Instead of suffering through looking more like a man dressed as a woman, Tiffany helps Walter look more like Wendy by doing his hair and applying his makeup. In exchange for giving Tiffany the three pair of shoes, the black pair of Jimmy Choo shoes, the Nike sneakers, and the Prada sandals, Tiffany offered to sty...

Could It Happen Again?

by mumblegooseegg on Sep 17, 2017
Loving Wives

This story is dedicated to those readers who liked "It Has Only Happened Once," a previous story of mine, and especially those who documented their positive feedback: RyeandGingerAyle, bruce22, johnnyjay85, HappyWife85, Grayhair61 and Bill (via email). Thank you, all of you! Here is a happy sequel to the saddish ending to that story, with my wife Linda losin...

Giada: Widowmaker Ch. 01

by WuddaWad on Sep 13, 2017
Celebrities & Fan Fiction

Diane Sawyer did her best not to be noticed by any of the NBC news personnel, as she hurried through the backstage area. Some staffers passed her by; none seemed to notice her hiding behind large dark sunglasses. Taking quick peeks at the names on the doors to the dressing rooms, she found the name she was looking for. She felt the cold steel of her .44 Dese...

Daddy'ss Girl

by Alice994 on Sep 1, 2017
Fetish

Even although my girlfriend was to be working away from home during the summer I was really looking forward to my long break from college. Clare had been offered a summer job in Canada - I would entertain my cross-dressing fantasies while she was away. And that was just how things went until in walked Clare's dad on me, while I was dressed only in lingerie,...

Internet Meeting

by Stillherer on Sep 16, 2017
Fetish

We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear -- discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures. We chatted online...

Story of Sissy Blackmail Ch. 01

by richysissy34 on Sep 13, 2017
Transsexuals & Crossdressers

I have been debating writing this up for a while, but it truly is a really hot story, that I figured you would all enjoy... so enjoy! (And yes, the title does speak for itself; it's a true story...) ***** I began cross dressing when I was 16 years old, and I am now 21. When I was 18 I moved away to college, and began living in a dorm on campus. I chose to...