Shemales Stories

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My First Trans Woman

by Indianaboy6555 on Sep 23, 2019
First Time

One of my favorite fantasies has always been shemales. I kept it a secret for a long time, but finally I had to explore it. I loved the videos I saw. Long hair, big tits, feminine features and a hard cock. I used to joke that they were the best of both worlds. I never pursued any though. They remained a secret fantasy until eventually I basically forgot ab...

Die Vermieterhure

by SuendigeLisa on May 28, 2012
Non-English (dated)

Mein Name ist Nora Zeitlos und ich möchte ihnen heute meine Geschichte erzählen! Alles fing damit an, das meine Mutter das dritte Mal heiratete. Als sich auch noch Nachwuchs in form von Zwillingen ankündigte, mußten Felix und ich uns sehr schnell um eigene Wohnungen bemühen. Für meinen älteren Bruder war das auch kein Problem. Felix war damals schon 24 und h...

Dick World

by darkness_drearing on Dec 25, 2019
Bisexual

For contributors As was stated at the top: while there were will be two general threads to go off of (for a guy and girl), feel free to create your own characters or scenarios. The only shared premise among them needs to be that they find themselves, however you decide that happens, in this universe and, as The Eagles would say, "You can check out any t...

Jack Off Junkie Ch. 02

by Anal Slave on Sep 13, 2017
Fetish

Jack Off Junkie Ch. 02: Getting Fucked By Shemales Well 9 PM rolled around and Kim and I were sitting in the living room waiting for Debbie to come over when the phone rang. My wife got up and answered it, it was Debbie and she wanted to know if she could bring a friend of hers along for the night. Kim asked me if it would be all right, I said sure that wo...

Pool Party

by GuyIncognito06902 on Sep 26, 2017
Celebrities & Fan Fiction

Happy to share this story with you. This one is a bit odder than the usual fare and I warn you going in that this story involves well hung celebrity shemales. I kind of wanted to save it as a surprise twist, but that seemed a bit unfair to have the story seem like a typical lesbian celebrity story and then have it be about girls with hot cocks instead of cun...

Pinch Hitter Ch. 01

by npanxx on Sep 14, 2017
Anal

This is a work of erotic fiction. All characters in the story are over the age of 18. ~~~~ My fascination with shemales had cost me my first marriage. I guess if I were to be honest with myself I would have to admit that the marriage was doomed to fail anyway. Barbara was as close to being asexual as a person could get, and in addition she was bitchy a...

First Cum, First Serve Pt. 02

by dreadknots on Jan 23, 2019
Sci-Fi & Fantasy

A sequel! This one has transformation of not just a gal but also a boy! If you don't like femboys and shemales might as well turn around at this point cause there's gonna be dicks, let me tell ya. Oh, and the standard cadre of weird fucking perversions: lactation, mind control, transformation. You know: totally normal things to get a boner over. Enjoy! **...

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...

Pinch Hitter Ch. 02

by npanxx on Sep 14, 2017
Anal

This is a work of erotic fiction. All characters in the story are over the age of 18. If you are going to vote, please vote on the story's merits. ~~~~ Lindsey, my daughter's best friend, had just fucked me to a mind blowing orgasm while posing as Sarina, one of my favorite shemales. "You are a DIRTY little boy, aren't you sugar? My, my! I never wo...

A Changed Man Ch. 1

by sub5000 on Sep 12, 2017
Fetish

Part One - Beginnings It had to happen one day I guess. I had such a collection of porn on my hard drive, that it was inevitable that one day my wife would stumble across it. It wouldn't have been so bad if it was average, everyday porn, but my collection consisted of more 'specialist' images. There were pictures of shemales with big hard cocks dressed in s...