Shemale First Time Stories

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Orientation
Length
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Infinite Scroll

Conditioning of a Scat Slave Pt. 13

by subtlesurrender on Sep 19, 2017
Fetish

The Ultimate Punishment Alone again in a bathroom; chained to a toilet bowl. At least this time Claudia had ample shit at her disposal. Almost the entirety of her load lay on the floor, as did the overflow from Shitface's diarrhea; which was in itself substantial. This time she wanted to savor the moment and avoid being left with nothing to do again. Let's...

My Shemale Mother

by yarracuda on Sep 19, 2017
Transsexuals & Crossdressers

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several years..here it is... I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I...

BORG Collective Pt. 02

by bladeday on Feb 3, 2020
Transgender & Crossdressers

Prologue In my first story, BORG Collective. I had stumbled upon a chat group obsessed with Star Trek Voyager. Their interests were the BORG Collective. After two nights of interaction in a chat with ten people, they invited me to a Cosplay party. At the party I could join, I had to swear to serve the needs of the Collective and follow all orders given, wit...

Becoming Victoria

by Writer345 on Sep 18, 2017
Transsexuals & Crossdressers

Prelude. I was happily married and still am, but things have changed; or should I say that things have been changed - I have been changed. I was or rather am still wed to Anika, a rather dominating Polish lesbian, who married me for reasons of her own that are still a mystery to me. I'm not the man that I was...Oh, this is so confusing I'd better start at...

Jabba's Shemale Slave Pt. 01

by mkh78 on Sep 24, 2019
Celebrities & Fan Fiction

This story is from the imagination of the writer and inspired by Return Of The Jedi. ***** The Hutt's sexual appetite was growing. He had been thinking about expanding his harem of gay sex slaves to include a transsexual. This was all due to a drug dealer who caught the eye of the exalted Hutt. Although they had done business only two times in five months...

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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Fun For The Powerful

by FEZBEE on Aug 5, 2019
Fantasy

An ancient entity without any name has decided to go into the human world and have some fun. In order to do this, the entity will be able to use all the powers at their disposal: -Electricity and Fire Manipulation And Generation -Superhuman Strength -Superhuman Durability -Superhuman Stamina -Super Speed -Shape Shifting -Teleportation -Healing Factor -Telepa...

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Hell of a ride

by Nqjim on Jul 18, 2018
Transsexual

(Would you like a German translation? I can make one as German. ) Hello. This story started as roleplay between me and a very sweet and sexy Girl from Kent. (If you read this. I hope it goes on for a very long time. Every word from you is pure sexy gold). I will write this story out of our two perspectives. so you can play the "innocent" Hitch-hiki...

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Zapp!

by The Dark Traveler on Jan 20, 2019
Science Fiction

You go to bed after a long day. You set your alarm as you have another long day tomorrow. You change into pyjamas, bush your teeth get into bed and try to sleep. You dream of your favourite sci-fi show. Then you dream you are in the show. Your dream shifts to another show also Sci-fi then your job. You dream of your friends your family. Then you dream of you...

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A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...