Double Anal By Shemale Stories

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Infinite Scroll

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...

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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Pool Party Ch. 02

by GuyIncognito06902 on Sep 26, 2017
Celebrities & Fan Fiction

It's time for a sequel and if you like imagining beautiful celebrities as hot, hung dickgirls with big tits and big cocks then this is the place to be. I hope everyone likes it. This story is COMPLETELY fictional and not meant for people under the age of 18. This is all fantasy and not any kind of reality. The story codes for this are FF, FF+, orgy, shema...

Pam's Shemale Experience Ch. 07

by majicman21 on Aug 20, 2018
Transsexuals & Crossdressers

Author's Note: While this is quite obviously a continuation of Pam's Shemale Experience, it also follows 'Pam's Gangbang Experience' from the Group Sex category, 'Pam's Lesbian Experience' from the Lesbian Sex category, and 'Pam's Threesome Experience' from the Loving Wives category. Reading those three stories might not be necessary to enjoy this one, but i...

My TG Tale

by mmm_tasty159753 on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 1 If I could see my future I would have no idea how I could have become what I see; a beautiful, young woman. You see, here and now, I am a slight young man, undersized for my age of 18; at just 5 foot 6 and 120 pounds I am far from the prototypical male physique. I have always been very nerdy and struggled to fit in anywhere or with anyone. As many...

Mikes First Transgendered Pt. 03

by SamanthaMeyers on Nov 16, 2020
Transgender & Crossdressers

Please read 1 and 2 before this one. Mid October has set in and once again I am leaving work later than usual. I am in the parking lot speaking with co-workers when my phone rings. I recognize the number as being from the restaurant Sara works at. I answered and hear her voice on the line. Sara Says, "Hi Mike. How are you?" "I'm good Sara. How are you?" I...

When Sara Met Bob Ch. 04

by yellowfrog on Sep 14, 2017
Fetish

PART IV: Sara sculpts Bob's lovely penis Days turned to weeks, weeks turned to months and Sara derived ever-growing joys from milking Bob's prostate. The implanted micro-devices gave Sara the ability to massage his prostate remotely, be it from a distance in the same room, to the other end of the bar at the shemales saloon they frequented often, and even ov...

How Dicks ended up in My Mouth Ch. 01

by ret123 on Sep 19, 2017
Transsexuals & Crossdressers

My name is Joe. I am a married, successful business man with a pretty wife. I lead the life of an upper middle class guy. I grew up in a small Texas city and had a great childhood. I was a football star in high school and college and dated lots of attractive women. Most people would say my life is ideal. However, I have some secrets. The story begins when m...

Father-In-Law Shemale Adventure

by greyhound_guy30 on Sep 16, 2017
Transsexuals & Crossdressers

My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last moment I decided to take the day off. Since the girls were out, I...

One Mad Night Ch. 1

by C_Duke on Sep 12, 2017
Transsexuals & Crossdressers

I'd experienced a great many crazy perverted things in my sexual adventures, but this was a new one on me. The sort of thing you read about, or hear about, or lied about, or just saw on porno videos. Whether it was actually a fantasy, fetish, or obsession was always down to you. But there I was, lying in bed, my hand exploring on my "female" partner's body e...