Crossdressers Chastity Stories

18,166 results
Orientation
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Infinite Scroll

Truth Comes Out

by TazDeVille on Sep 14, 2017
Transsexuals & Crossdressers

"Whose panties are these?" Jane shouted at Liam waving the lacy pink panties at Liam. "I found them in your pocket! Who is she? I want to know now Liam!" "They're mine!" he answered quietly standing in his bathrobe in the kitchen. "Is she that whore at work manning the phones? We've been married for two years and you're already cheating on me. I'm going to...

Pandora's Promise Ch. 02

by adoration on Sep 13, 2017
Transsexuals & Crossdressers

The rest of the evening was spent with us chatting, interrupted by the occasional blowjob from her to me, but she didn't come again. "Tomorrow's a big shoot day and I must be at my best," the lovely 22-year-old told me. "After the shoot, I'm all yours." "Promises, promises," I laughed, in what had become a sort of catch phrase between us. Pandora, I learne...

W Is for Wendy

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

*** A series of stories with TG themes, dedicated to women, and to men who like to be women (which includes me!) *** "Will, I need to talk!" My cousin Amanda pushed past me through the hall and strode into the lounge. I'd not been expecting her, not at all. I made sure the front door was closed and then turned and followed her. When I got as far as the lo...

Korra & Asami: Morning in the Palace

by Otaku_Apologist on Sep 14, 2017
Transsexuals & Crossdressers

She was in that mellow state of morning stupor that follows a good night's sleep. For a second she felt light like smoke: softness of the bed embraced her back, blanket her chest. Narrowing her eyes in the dark, she could see but shapes of furniture. The room's smell was familiar; it stirred memories from last night. Even under the twilight of drape-blocked...

Going to a Wedding

by weluvhose on Sep 16, 2017
Transsexuals & Crossdressers

My wife and I recently were invited to a friend's wedding and reception. I knew that this would be the perfect dress up occasion for both of us and the excitement built inside of me thinking of the possibilities! As she prepares herself in front of the mirror, I ask the timid question if she minds if I wear a pair of hose under my suit. She responds, "Of co...

The Frill Of It

by decimus on Sep 16, 2017
Transsexuals & Crossdressers

The crunch of dirt underfoot doesn't hide the louder sound of your heels on the floor. The room is empty, it echoes as you walk. It is dark. You can only just see. You are alone. Probably. Being here was your idea; your fantasy. Making it a reality is at the same time the most exciting and most terrifying feeling. Walking here, dressed as he demanded the...

My First Ladyboy Ch. 02

by 69plus1 on Sep 19, 2017
Transsexuals & Crossdressers

We had just fucked ourselves senseless and Billi was leading me to her shower. After she adjusted the temp we got under the spray. First off was to clean my cock of the lube and cum. I leaned back to the shower wall and spread my legs like a slut as she covered me with soft soap from cock tip to balls and back to my ass. I was sexually spent but she easily...

Birthday Party Ch. 02

by iser21 on Sep 12, 2017
Transsexuals & Crossdressers

If you have not read part 1 please do. This way you will know what happen up till now. It was now about 11 pm and Sue and I have been at it for the past 3 hours. Sue had me get up and go into the bathroom. As I stood in the shower I thought of what we did. Sue knew how to pull the right strings on me or in me. And she knew what pleased me. I washed all over...

A Holiday Job

by Misslexia on Sep 14, 2017
Transsexuals & Crossdressers

'Bye!' Paul stirred briefly in bed as his twin, Anne, called out as she dashed from their holiday apartment. Paul glanced at his watch; it would be a rush but she should make it to the airport in time for her flight back to England. They had been on holiday at a popular Mediterranean resort for a week. Anne had to return for her job was starting, but joble...

Cancelled Date Night Ch. 06

by kinglem on Sep 16, 2017
Transsexuals & Crossdressers

Colleen looked gorgeous, as hot as any girl he'd been with, including Sarah. Her face, even with smeared make up and frizzy hair, was still cute as hell. Her slim body was smooth and soft touch, the push up bra even giving it just enough shape to complete the look. Her ass gripped his cock so tightly he swore he could feel the vibrations from her heart bea...