Shemale Piss Stories

24,697 results
Orientation
Length
Source
Infinite Scroll

From Tomboy To Boy

by PredatorSmile on Sep 16, 2017
Transsexuals & Crossdressers

Mike Flannigan is a wealthy man who, at the age of forty, could certainly afford to retire from his law firm with a lot of money to spend. He had always been the most driven person in his family. He was born in 1951 in Dallas and lived there for most of his life. His parents were a working-class couple, a policeman and a teacher. Mike Flannigan went to colle...

Jenna & Stephen Ch. 02

by Naf_Noparts on Sep 12, 2017
Transsexuals & Crossdressers

AUTHOR'S NOTE: My intention all along was to follow up with the progress in our relationship shortly after my original story, but so much has happened since that the story I'd start to write would be scrapped again and again. Here is the latest. Thank you so much to those of you who gave it such a high score, for your comments and constructive feedback, and...

My First Shemale Sex

by available269 on Sep 26, 2017
Transsexuals & Crossdressers

I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our firm in Las Vegas had experienced a server failure, and I wa...

The Creation of Amy Ch. 02

by michael1k on Sep 14, 2017
Transsexuals & Crossdressers

I woke with the sunlight streaming through the gap in the curtains in my room. I felt like I had been sleeping for hours. I felt warm weight laying on me. It was Amy. She was laying with her head on my stomach inches from my flaccid cock fast asleep. Her left arm and left leg thrown across me. I reached down and ran my hand over her perfectly smooth femini...

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...

Mommy's Slave

by Futafan567 on Dec 7, 2019
Transsexual

You are Jim. You are 18 years old and live in an average sized home with your mother Jennifer (Jen for short). Being homeschooled for most of your life, you never went outside very often. In fact your only “friends” are the two girls Amy and Mary who live across the street. You are really only friends with them because they live so close but you were never t...

Open in Reader

Brazilian Shemale

by Thorsten007 on Dec 30, 2017
Transsexual

Rules: Needs to be a brazilian shemale with big tits, a fat cock and a nice round bubble butt! Feel free to continue and create new storylines.What's next? James Kingston Pablo What's next? James Kingston Pablo...

Open in Reader

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

Blossoming Shemale Ch. 03

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale If you enjoyed it, I hope you'll enjoy this series. A note on political correctness: I have come to learn just a tiny bit about the transgender community, and by that I mean that I've learned that words such as shemale, transsexual and dickgirl are offensive...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...