Shemale Stories

1,331 results
Orientation
Length
Source
Infinite Scroll

Sweet Sherri

by BrettLynn on Sep 16, 2017
Transsexuals & Crossdressers

"The fuck you want," the girl hissed through her teeth. Well, it's hard to say. For one, this was the one night of the week at the particular club that was tranny night. Unless the lucky woman was either a straight freak or had been exposed to the scene, there weren't too many people walking around with a double dose of X chromosomes. Two, the girl hissed w...

The Librarian Ch. 05

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Part Five -- Trust Sarah finished in the shower and came out to find the Makeup and Wardrobe departments had been at work. There was a small toiletries bag, similar to those gifted to first class passengers on long flights and she was able to brush her teeth, gargle with mouthwash and brush her hair. She used deodorant but there was no makeup. There was al...

A Cyber-Awakening

by fyredreams on Sep 15, 2017
Transsexuals & Crossdressers

This story is based partially on an online chat I had once with a real person, who will remain nameless for the sake of privacy, when I was back in college. The woman in the story showed me a new side to myself and my sexuality that I had never known existed until I met her online. I will be forever grateful to her for taking me under her wing, showing me a...

Learning the Chocolate Life Ch. 02

by boomeronaleash on Sep 17, 2017
BDSM

It had been a week since my glorious encounter with Mistress Angie. I swear I can still feel my balls on fire. I had sent numerous IMs but no reply until Thursday. "Stop pestering me you little fuck. I'll contact you not the other way around. You'll just have to wait until I feel you are worthy of another session. Contact me again and I'll show your prissy,...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Balancing Act

by devoutmalesub on Jun 24, 2019
Transgender & Crossdressers

*Delayed sex for my typical stories. Please remember the category you're in. *More comments/feedback, please. Have the fortitude to not be anonymous. ***** At my last company, I was the fixer. I was brought in to right the ship and save myriad accounts from leaving. Along the way, I built a team stealing other people from other places in the company. Buil...

Cam Slut Pt. 01

by GavinIsaNuisance on Oct 26, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Eighteen year old Jeremy Briarstein is forced to remain home while his parents go on an extended twenty year anniversary vacation. He is further dismayed to dis...

Love Rekindled

by HerLittlePiggy on Sep 19, 2017
Fetish

I watched her walk naked into the room, my eyes devouring every nuance and curve as my heart raced and my flaccid cock began to stir. Her bright green eyes sparkled knowingly and a mischievous grin danced on her full lips. She was beautiful, sexy, intelligent and giving and I loved all of those things about her and more. I'd first met her nearly a decade ear...

Oops, I Did It With Britney Pt. 02

by britneyfan on Sep 14, 2017
Celebrities & Fan Fiction

3. I'm Not a Girl, Not Yet a Woman As you can imagine, the sight came as quite a shock to me. My eyes practically popped out of their sockets and my mouth dropped open at the sight before me. Britney Spears, America's sweetheart, the world's sexiest superstar, the woman I had spent the last five years lusting after, was no woman at all. Sure, she had those...

The Virgin Tranny & the Bride Ch. 04

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Continuing the story of young transvestite Roberta and her adventures with Margaret and John. I have also received the following letter which is a little worrying. Dear Yano, I'm very sorry it has taken me so long to send the next part of my story, things have been very strained over the past few months and particularly between me and Margaret since I got...