Shemale Stories

1,331 results
Orientation
Length
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Infinite Scroll

The Lost Boy Ch. 02

by DamienDeath20 on Sep 25, 2017
Transsexuals & Crossdressers

A.N. Hello hello hellooooo! Welcome back to the next chapter of The Lost Boy! Chapter one received soooo much positive feedback, and with a lot of encouragement from both you guys and the commissioner, chapter two was very quickly conceived! The Following Contains: Rough sex between a sexy as fuck dominant dickgirl and an adorable femboy. Who is reluctant...

Open Your Mind to Something New

by Dazman on Nov 4, 2019
Fetish

Open minds create amazing experiences This experience had its genesis in my early twenties when I unexpectedly began exploring my bi-side with my childhood buddy, Lyndon while both of us were studying at university (refer to my story Friends Satisfying Each Other for background context). This story takes place over a weekend, Friday evening to Sunday after...

Cheerleader's Mom: Fucking Her Ass

by silkstockingslover on Dec 9, 2019
Illustrated

Summary: Submissive Mom is trained in orgasm denial and ass fucking. Note 1: Thanks to hfernandez1983 for doing the visuals for this story. Note 2: Thanks to Robert, Wayne, and Tenzin for editing. Recap: In Part One, A POWER SHIFT: 39-year-old mother, Michelle, decides to try on her daughter Allie's slutty cheerleading outfit. Once she has it on, she beg...

Fledgling Pt. 01

by NRMathis on Jan 22, 2019
NonHuman

++++++++ Part 1 of 2 ++++++++ It's dark... It's silent... I'm alone... No, wait...I'm not alone. Something is waiting for me. I have to get to it. It has a magnetism I can't resist. I push and push and... My eyes open and the room I'm in fades into focus. I'm on a bed. How did I get here? Where am I? As I sit up, I try to think back to the last...

Hearts Academy Ch. 04

by RoseB on Mar 16, 2020
Transgender & Crossdressers

Disclaimer and Notes: Disclaimer and Notes: Hearts Academy is an dark horror/mystery story focusing on the reluctant feminization of a young artist. There are many themes such that cause it to be disturbing for those who cannot handle terror or dread well. This is a sequel to The Rose Diaries. While the characters are brand new, it does reference events an...

The Robertson's Sissy Ch. 14

by Clite69 on Apr 28, 2020
Transgender & Crossdressers

My apologies on my disappearance, life has been crazy. Though this chapter might not have been worth the wait I am sure the following chapters it sets up will. *** Lela and I had spent most of the night cuddled up on the couch. I was woken around 4am by Lela who wanted to go up to the bedroom. In a half sleeping state I followed her upstairs and collapsed...

My Journey Ch. 05

by npanxx on Sep 25, 2017
Transsexuals & Crossdressers

This is the fifth installment of My Journey. Although not necessary, this story will be more appreciated if you read Chapters 1 thru 4 first. Thank you to all who read my first four submissions and provided feedback. I hope you enjoy reading the story as much as I enjoyed writing it. (And I REALLY enjoyed writing this one!) Please, please leave comments a...

Meeting Raquel Ch. 03

by Floydman1 on Sep 15, 2017
Transsexuals & Crossdressers

After that, I didn't have much in the way of discipline problems with her. Raquel still got off in a big way on being punished, so I would incorporate it somewhat when we were having sex, but mostly I fucked her after she was tightly bound. Out of nowhere, one day she asked me, "Have you ever thought about bringing somebody else in to play with us? Like a re...

Sara's Silken Ladder Ch. 04

by Calandria2 on Sep 16, 2017
BDSM

Only if you've read the first three parts will this make sense. Everyone in this story is over eighteen. * I glanced at my companion as we were both eating a rather limp sandwich on our flight to Alicante, and wondered at just how little I knew about Kirsty, the girl I'd just agreed to share my life with. Achingly beautiful, she certainly was, and when she...

Mia Mine Ch. 10

by cliptoe on Sep 26, 2017
Transsexuals & Crossdressers

Mindy stared at the droplets of rain as they ran down the window of the little coffee house with free Wi-Fi. She was waiting for the special website to load so she could change the phone number in her ad to the new 'burner' she picked up. She needed one more "liaison" (she hated the word trick, it made her feel cheap), to make enough to get a room for the ni...