Surprise Shemale Stories

136,276 results
Orientation
Length
Source
Infinite Scroll

Dr. Landry and Nurse Lisa

by newfield1981 on Apr 17, 2018
Transsexuals & Crossdressers

This story is a spin-off from the "Neighbors sissy son" series. Though it stands alone, it will eventually cross over with NSS. SPOILER This series falls in the transsexual crossdresser category for the first story. There will be very little in the way of men participating in gay sex. This series will sometimes revisit this subject. After that it will be ba...

A Shemale Christmas Carol

by ThomX on Sep 16, 2017
Fetish

I got a job working as a mall Santa at the local mall during the Christmas shopping season one year. It had been a real shitty year for me. My wife of almost twenty years left me for a younger man, I lost my other job due to layoffs and, on top of all that, my doctor diagnosed me with high blood pressure (gee, I wonder why?). So believe me when I say the las...

Making Francesca Ch. 07

by Spango on Sep 16, 2017
Transsexuals & Crossdressers

After the glorious sex with Mistress Celia, Frank spent the rest of that day doing housework with Justin. His mind was all awhirl. To all outside appearances, Mistress Celia seemed to be the beautiful woman he had lusted after when she was a waitress at his favorite bar, but now he knew that underneath her clothes she hid a wonderful piece of man-meat. His n...

Spicy Story

by TexanBelgianCutie on Jul 17, 2019
Transsexual

Family Kyle had wildly mixed feelings when he saw his mom walking towards him. He kept his feelings to himself however and forced a big smile to welcome her back from the SpringWood Adult Mental Hospice. He had not seen her since he was child, yet he was glad to see she looked healthy and happy. “Hey Sara”, he grimaced, “How are you? Sara had spent the last...

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TGirl4Life

by spitzharder on Sep 15, 2017
Transsexuals & Crossdressers

The multi corporation, 'TGirl4Life' had combined cloned human DNA and Nano-technology in what they called an 'Androgenous hybrid,' to all intents and purposes a living, breathing human. This new person, however, was created from artificial bones and flesh and already the equivalent of a nineteen year old. Their factory was in a discrete area of an ordinary...

Making More Dreams Come True

by Writer345 on Apr 4, 2018
Transsexuals & Crossdressers

Just a couple of points, this story is written in British-English so the spelling and grammar may well differ from that of the particular dialect in which you were educated. It is also FICTION: anonymous please take note! The events depicted in this story take place in the months following the end of Making Dreams Come True and so may possibly make more se...

How I Met My Shemale Pt. 02

by Eroticalover1968 on Sep 25, 2017
Transsexuals & Crossdressers

I sat motionless and stared at her as she swirled her thumb around the end of her glistening member. It was very well lubricated with her sex fluid. "Hey you! Don't you know it's rude to stare?" she shouted, breaking the trance I'd been lost in. "Oh, sorry," I said as I glanced up at her furtively. She was murmuring something to herself while drawing her s...

futapus complex

by redpulse0091 on Jan 28, 2019
Fetish

Erik walks up to the front door of his home and pulls out his keys from his backpack. Unlocking the door and walking inside he takes a moment to stretch. Feeling relieved that finals are over and he isn't going back to school for a while he starts walking to the kitchen to grab a snack. Grabbing a protein bar and an apple he continues to his room, turns on h...

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Poke-Futa

by Sex-Shooter on Dec 6, 2020
Fan Fiction

A light came upon a mysterious figure, feminine with a bulge between the legs, and the figure waved. Then she spoke cheerfully: Hello there, [Redacted]! My name is Professor [Redacted] and welcome to the [Redacted] region! Before we start, let me tell you about the world. Our world is filled with Pokemon, special creatures that resemble us in terms of body s...

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The Surprise

by Abusedbyfuta on Jul 17, 2019
Miscellaneous

You are a young man in his senior year of high school. Well man might be bit of a stretch. Your still immature, you still like to drive around in your car and go on pussy patrols, and you certainly aren’t was woke as you like to pretend you are when your around attractive girls. Although still a senior your one of the oldest in the school year which means th...

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