Cross Dressing Stories

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High Heels and Stockings Tryout Ch. 02

by neon_noodle on Sep 11, 2017
Transsexuals & Crossdressers

Chapter 2: Bi-sexual Sluts in Stilettos Author's Note: Thanks to all who read and enjoyed my first story. I hope you like this one too, and get so excited by it you have to jerk off and blow a big, wet load. Enjoy! * After my first semen-splattering cross-dressing experience, I was hooked on dressing up like a slut, and masturbating in stockings and high...

Influential Factors! Ch. 15

by gummidurango60 on Jan 1, 2019
Transgender & Crossdressers

I woke in horror; only to realize I was in bed... my bed. Nothing seems to have changed from yesterday; I was still in my LA Rams Cheerleading outfit... boots and all. I reached up and felt the collar around my neck, it wasn't tight; but it wasn't loose either; and to my delight the cuffs were gone. I got out of the bed and headed toward the bathroom to d...

Unbelievable! Ch. 04

by peterpeck on Sep 16, 2017
Mature

When I returned to the studio around five in the afternoon, I found Eve busy in the editing suite. I showed her the results of my location visit and the meter readings from the church. However, I didn't report I'd spent a couple of very pleasurable hours screwing the bride's mother and the maid of honour! Although, I was damn sure she could sniff the residua...

Black Femdom for Black Sissies

by Samuelx on Oct 15, 2017
Transsexuals & Crossdressers

"Dammit, Dalton, you're into some seriously twisted shit," Marjorie Etienne said, and the tall, curvy, dark-skinned young Haitian-Canadian woman looked at the man standing in front of her. Dalton Etienne liked to walk around the City of Ottawa, Ontario, like he owned the damn place. Six feet three inches tall, burly and chocolate-skinned, with a slick goatee...

The Lap Dancer Ch. 03

by Travel_by_day on Sep 16, 2017
Transsexuals & Crossdressers

After the break of more than a week between my first and second lap dances by my cross-dressing roommate, the frequency of our session increased dramatically. The transformation of my roommate Jim into his female alter-ego Jubilee and the transformation of our living room into the strip club "The Pussy Pole" was soon a daily occurrence. "Jim, you realize th...

Hot Sex Instead of Dancing Ch. 16

by SusanJillParker on Sep 16, 2017
Fetish

Please give me the support of your vote. * Walter shares his fetish for women's panties with Tiffany after having sex with her. Never wanting to let her go, Walter remained in bed with the love of his life, 30-something-year-old Tiffany. With him suddenly a player, the big man on campus, and the Don Juan lover of a man, albeit a man in a dress and wig whi...

Yellow Polka Dot Bikini(s)

by PositiveThinker on Sep 14, 2017
Transsexuals & Crossdressers

"She was afraid to come out of the locker. She was as nervous as she could be. She was afraid to come out of the locker. She was afraid that somebody would see. Two, three, four, tell the people what she wore. It was an itsy, bitsy, teenie, weenie, yellow polka-dot bikini that she wore for the first time today. And itsy, bitsy, teenie, weenie, yellow polka-d...

Halloween Cross-Dressing Bash Ch. 03

by BOSTONFICTIONWRITER on Sep 16, 2017
Exhibitionist & Voyeur

She escorted him to the other side of the store and now that he was relaxed enough to take note of the woman who was helping him, he determined that they were both about the same size. She was pretty, much prettier than his wife. He felt better knowing that she could help him pick out the correct sizes he needed without making her think that the clothes were...

Men's Sexual Confessions: Henry

by PositiveThinker on Sep 14, 2017
Fetish

Best Buddy's Sexual Peccadillo A group of men sit around talking candidly about their sex lives. I'm Paul, the host of this party. Thanks for stopping by to read my story. We were all sitting around the big screen watching the Super Bowl one year. I had invited all of my best buddies to watch the game with me. There were 21 of us guys, including me. Our w...

Adventures of Alice and Alex Pt. 04

by AlexCarroll on Sep 14, 2017
Transsexuals & Crossdressers

Alex wears lingerie again, and Alice hears of his first cross-dressing experiences ... In the following days I nervously waited for Alice to mention, what had for me been a momentous occasion, and now I could not stop thinking about sex with Alice while I wore the red teddy, or perhaps the black baby-doll, and I was desperate for more. After about a week,...