Shemales Stories

429 results
Orientation
Length
Source
Infinite Scroll

Opening Him Up Ch. 07

by humbleboy on Sep 17, 2017
BDSM

Amy looked down at her slave Lisa, her former husband, which now appeared very effeminate. He stayed perfectly still on his hands and knees in front of her, not only because of his obedience but also the shock that he was finally able to cum with just the stimulation of his Mistress's strap-on. She looked down between her legs and saw the thick dildo protr...

Trailer Trash Tranny Ch. 06

by Travel_by_day on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 06: Hotel When Alexei and Mats left, Alexei gave Jeannie his email address. "Email me, and I will let you know when your movie is up on the Internet." Jeannie didn't have an email account or a computer, but there was someone in the trailer park that had a nice computer set-up. Christopher Dalton was a class mate of Jeannie's back when she used to g...

Trucker's Surprise

by Mymantoy999 on Apr 3, 2019
Transgender & Crossdressers

NOTE 1: First I would like to thank Silkstockingslover for granting me permission to use her name and story title as a background for my story. NOTE 2: This is my first attempt at fantasy, meaning other than the fact I am a truck driver and I do like the food at Petro truck Stops, none of this is factual in any way. NOTE 3: As stated above this is my fir...

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...

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Shipwrecked Pt. 01

by JJ122964 on Sep 13, 2017
Transsexuals & Crossdressers

I was not sure where to put this story. The story is just starting out so some prep time is required. I hope you all like and say so in the comments. ************************** Shipwrecked I don't remember too much of what happened to the ship, all I really know is that it sank. It was a cruise that we had chartered for a week and everything was fine unti...

My Life as Lauren Ch. 03

by Lauren_xxx on Sep 13, 2017
Transsexuals & Crossdressers

I had become a manager in the shop which meant that I had to dress in a very professional way, if I was still a man it would have been quite annoying but Bev new that as a woman I would love to wear a blouse and skirt but she also knew it meant that I could dress really slutty at the same time a "smart tart" in a way. Whilst working there the shop had opened...

Bangkok Hilton

by Erotica1970 on Sep 16, 2017
Transsexuals & Crossdressers

A straight guy for 34 years, I had always harbored a special interest in shemales. Not that I would ever admit it publicly. And that's how I met her, in an internet chat room. Cyberspace, where one can indulge in every fantasy in complete privacy. I was in the Big Apple and she in Bangkok. We chatted sporadically for almost a year. She discovered I was a ban...

Riding in Cars with Shemales Ch. 02

by lfullback on Sep 25, 2017
Transsexuals & Crossdressers

Note: This is a sequel to my previous story, "Riding in Cars with Shemales." If you would like some back story into how Terra and Matt met, please read it. If not, you can probably still enjoy this one by itself. * It was a wonderful day in May. The sun was shining. The sky was clear. Birds were chirping everywhere and everyone was spending their Friday a...

Shemale Surprise

by luckybaldrik on Sep 12, 2017
Transsexuals & Crossdressers

It was a Saturday night and I was chatting up this girl at my favorite bar. Her name was Heather and she had short light brown hair. She was cute, big in general, big boobs and a big ass, but she wasn’t pudgy, and in fact she had a very athletic body. She wore a short white miniskirt with a dark tank top and pink fishnet type top over it. We had really hit...

Shipwrecked Pt. 03

by JJ122964 on Sep 13, 2017
Transsexuals & Crossdressers

I am Sorry, but I have to break up the forum portion of this story. Otherwise it would be too long. I hope you like the series and please comment. Thanks J. ********** The tasting house. I woke up to the feeling my ass being penetrated by something. I was still on the X and being cleaned again. I saw that my loincloth was on the table and the ooze was on...