Mistress Shemale Stories

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Orientation
Length
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Infinite Scroll

Loraine's Self Bondage Re-Creation

by loraineveritas on Mar 12, 2019
BDSM

The following is my re-creation of an event that happened a few years ago. I had been a sissy slave to Mistress Marie for over 2 decades during which I become a totally submissive slave to Her every desire. I think of Her often as She has passed now. While doing Self-Bondage activities shortly following Her passing my wild imagination conjures up the Mistres...

Swallowing My First Shemale

by Nitromethane on Oct 14, 2017
Transsexuals & Crossdressers

It's been a couple of years now that I've been intrigued by shemales, and though I've met up with a few I've met online, I've still not gone any further than some stroking or letting them blow me. I'm not sure what my hangup is, since I can't seem to stop watching these gorgeous girls on all the websites, but I'm still so nervous about taking that big first...

Genie Chronicles - Make a Wish 02

by BebopJet on Sep 19, 2017
Sci-Fi & Fantasy

A big thanks goes to Joe Brolly for the original Genie Chronicles. As many people have done, I'm simply taking his original story format and giving it a twist. Fair warning, lesbian and futa (shemale) sex will feature heavily in this storyline. Thanks to Ultrafem and Stickymon for drawing pictures that inspired these stories. Scarlett Johansson also appears...

Sweet Julie Birth of a Shemale

by tawnysuede on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One Is It Just a Role? The dress rehearsal for the drama club's latest production was over. The curtain fell, the audience of excited parents applauded enthusiastically. The curtain rose and the performers stepped forward to take their bows. The curtain fell again and still the crowd applauded. The two stars, Troy and Julie, took their positions ce...

Dark Angel Ch. 03: The Ride

by ReiverToo on Sep 16, 2017
Transsexuals & Crossdressers

Agreeing to lick Angel's ass and actually doing it, I found, were two different things. Between my mouth and her asshole were two significant obstacles . . . her dick and her balls. I'm kneeling painfully between her legs in the cramped confines of the Town Car's floorboards. I'm trying not to interfere with her safe operation of car's pedals. And I'm trying...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

The Shemale Apocalypse Ch. 01

by cocklover1000 on Sep 15, 2017
Sci-Fi & Fantasy

The first place anyone really heard of it was large outbreaks in Thailand. No one knew what it was but the government played it off as a life choice via simple operation. But it was more then that. Minor cases were reported all over the world until 2011 the government in an effort to quell what they called an infection told the earth the truth about the wond...

Bambii's New World

by mikhaylacumme on Sep 12, 2017
Transsexuals & Crossdressers

My mind was racing the whole time. I couldn't believe where I ended up. But the sensations were running through my body. A 9-inch cock was ramming my boy pussy as hard as it could. Another cock, at least 10 inches, was being forced down my throat as his hands wrapped around my head, forcing me to deep-throat his amazing piece of man meat. Once he allowed...

Genie Chronicles - Make a Wish 01a

by BebopJet on Sep 19, 2017
Sci-Fi & Fantasy

A big thanks goes to Joe Brolly for the original Genie Chronicles. As many people have done, I'm simply taking his original story format and giving it a twist. Fair warning, lesbian and futa (shemale) sex will feature heavily in this storyline. Special thanks to Ultrafem, Stickymon, and Ninjakitty for drawing this and many other pictures of these two charact...

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...