Shemales Stories

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Orientation
Length
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Infinite Scroll

Alternate Reality Ch. 03

by grgy56 on Sep 12, 2017
Transsexuals & Crossdressers

"What? How the fuck can I get pregnant?" I asked myself. Dressed in some new, experimental VR body-wear equipment, I am my avatar Krystal. I'm stuck in the SIM: Slut City VR game because I skipped reading the manual on how to exit. I asked my VR lover Renee to help me out. She came over to my VR apartment where I found out she changed herself from a female...

Broken on My Break Ch. 02

by TopSeeker on Nov 13, 2017
Transsexuals & Crossdressers

**Disclaimer, all people places and events in this story are completely fictional and made up by me. This story contains the following elements: non-consent, dominant shemales, spiked drinks, shemales/transgenders being the penetrative partner to males, many terms used which are derogatory both in general and specifically to trans-gendered individuals. Pleas...

Pandora's Box Ch. 01

by afroauthor on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 01: Paul and Mag Hi, my name is Paul and this is the story of my first time, sort of. * I discovered transsexual women completely by accident when I was 18. I was watching one of those Real Sex shows on HBO, and without warning, two women who were showering together for a video shoot turned around and I was shocked when I saw cocks where I expecte...

Conditioning of a Scat Slave Pt. 07

by subtlesurrender on Sep 19, 2017
Fetish

Part 7 – The Filth of No Return This exchange between Mistress and slave, this confirmation of her brutal humiliation, exacerbated Claudia's hormonal roller coaster ride. The submissive switch had been activated and she was well aroused by now. More and more people were taking part. Everywhere she looked was a stream of piss, a load of cum, or a dump of tur...

My First Bottom Experience

by NoLongerCurious on Jun 4, 2019
First Time

I never thought of being with a man until I was 45. It was the internet that sparked my curiosity. I first discovered shemales on the internet and was very aroused by men sucking shemale cock. I realized that cock was really hot and I wondered if it might be fun to suck one. That lead to a nervous craigslist encounter with a very nice guy who lead me patie...

The Bimbug

by Testytesterton on Jun 17, 2020
Science Fiction

The world changed overnight with the first cases of the Sexually Infected Subjects Spreading Infections Exponentially Syndrome, or SISSIES, became known. At first it sounded like some urban legend, men turning into hot, horny, hung shemales and spreading the infection to any man that came in them...or any man they came in. It was only after you saw video evi...

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Husband's Anal Adventure Ch. 08

by Anal Slave on Sep 19, 2017
Fetish

Well I woke up this morning and everybody was still a sleep so I got up and made some coffee. I was sitting at the table drinking coffee when my wife came walking in and sat down beside me. She gave me a big kiss and I could still taste the male cum in her mouth from the previous night of fucking and sucking. She whispered in my ear that I was going to have...

The Lands without Men

by gothamalleyviper on Oct 19, 2019
Fantasy

The Island continent of Lemuria isn’t of this earth. It lays in the ocean of the red currents in the southern hemisphere. It looks like a dart board target with forest and city islands forming circular bands with three kilometer water ways forming the lines between the sections and the radials towards the center of the land mass. In the center is an island c...

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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...

My New Neighbours

by csm1967 on Dec 12, 2018
Transgender & Crossdressers

The house next door had, for the past 15 years, been a rental property, mainly for members of the defence force. Neighbours stayed not more than 2 years and some seemed almost gone overnight. Tenants ranged from singles, to couples, to families with children. The place had been empty for a couple of months since the previous quiet couple, and their noisy dog...