Shemale Aunt Stories

13,688 results
Orientation
Length
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Infinite Scroll

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

Erotic Dreams

by NewHere123 on Apr 22, 2025

Hi everyone, This isn’t so much a story as it is a dream diary. Sometimes I wake up from really intense, vivid dreams. And sometimes I spend five minutes writing down the details I remember from the dream (in an effort to increase lucid dreaming). Sometimes these dreams are pretty epic, with dinosaurs and robots and stuff. Other times, they can be pretty ero...

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Mommy's Slave

by Futafan567 on Dec 7, 2019
Transsexual

You are Jim. You are 18 years old and live in an average sized home with your mother Jennifer (Jen for short). Being homeschooled for most of your life, you never went outside very often. In fact your only “friends” are the two girls Amy and Mary who live across the street. You are really only friends with them because they live so close but you were never t...

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Room service

by Rookiegag on Jan 10, 2015
Miscellaneous

You´ve been driving all day on the highway. Fear of flying has its massive downsides, like incredibly boring days spent driving to get to your aunt in Chicago for Christmas. You check the GPS app on your iPhone and it alerts you of a motel a few miles ahead. It´s not cheap but not expensive either. Feeling weary to the bone, you decide to get a bed for the...

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Sheena's New Girlfriend

by Writer345 on Sep 16, 2017
Transsexuals & Crossdressers

Okay, here's my second attempt at a story for this site: it starts slowly, so if you are after instant gratification: look elsewhere. Thank you to the people who advised me about story classification after "Plaything": I'm pretty sure that I have got this one right, though! Please let my have your constructive comments as they will help me to improve. Please...

Shemale Beauty: 1st Female Conquest

by silkstockingslover on Sep 13, 2017
Transsexuals & Crossdressers

Summary: 18-year-old discovers her powerful sexual persona. Note 1: This is the first of potentially many shemale stories starring the beautiful seductress Kara... Note 2: Thanks to... Tex Beethoven, Robert, and David for editing this story. Shemale Beauty: 1st Female Conquest Everyone has hobbies. For most people, hobbies can be activities like trav...

Just as I like it.

by Revan on Apr 18, 2017
Miscellaneous

Important Notice: On my vacation just now, I found out that I lost some of my fun at writing ever since posting what I created, because I always thought about what would be good for the readers. Something I never did in the years before. I wrote a story just as it came to my mind once again and can tell, that it does far more to relax me than what I did in t...

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The Society Ch. 02

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

The French maid outfit was just a little loose. I was borrowing Corinna's dresses until I was fitted for my own uniforms and outfits. Actually Corinna and I were close to the same dress size yet our body types were different. I had a more feminine build with flared hips and hard round buttocks while Corinna's more muscular build created a deeper V shaped upp...

My Journey Ch. 04

by npanxx on Sep 25, 2017
Transsexuals & Crossdressers

This is the fourth installment of My Journey. Although not necessary, this story will be more appreciated if you read Chapters 1, 2, and 3 first. Thank you to all who read my first three submissions and provided feedback. I hope you enjoy reading the story as much as I enjoyed writing it. Please, please leave comment and suggestions! ***** I opened the...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....