Shemale Dating Stories

35,053 results
Orientation
Length
Source
Infinite Scroll

Shemale Devil in Disguise Pt. 03

by Chomedey on Mar 2, 2020
Transgender & Crossdressers

This story is the continuation of Shemale devil in disguise, part 02 Mid-July 2018: About two months have passed since I went back to my parents for work and almost a month since me and Joel decided to do some investigation about Rebecca. Okay, I'll admit, we didn't find too much. We both added her on Facebook but she never accepted the friend request. We d...

When Sara Met Bob Ch. 02

by yellowfrog on Sep 14, 2017
Fetish

PART II: Bob learns to sip Sara's pee and Sara explores his prostate. * Our first night together was one of unblemished bliss. Spooning Bob all night, I felt his breathing and his heartbeat. With the first rays of morning I knew we both had to rise and shine for the day ahead of us. Neither wanted to get up, especially not me. On the other hand, my bladder...

Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

Pam's Shemale Experience Ch. 04

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

Neighbors strolling by the residence of Pam and John believed the day to be one like any other. It was a Saturday, balmy and humid; nothing out of the ordinary had happened or most likely would happen. Some neighbors knew that John was away for the weekend, and that the children had gone to visit their grandparents. Those same neighbors also knew that a frie...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

Open in Reader

Joel Gets Caught by His Wife

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is a fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * It was Monday afternoon. Joel had taken the day as an opportunity to work from home...

Tony to Tanya Ch. 02

by joshy029 on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: Thanks to everyone who read, voted and commented on the first installment of the "Tony to Tanya" series. I'm really appreciative of you all. It is, after all, always good to get such positive comments as a new writer. I'd also like to say that i have another installment after this one. It's only the most basic of ideas right now, but it will...

Celebrity Shemales!

by Thorsten007 on Feb 6, 2018
Transsexual

Here, you can fuck the shemale version of your favorite celebrities! Feel free to add new celebrities! IMPORTANT: Leave a like for whichever celebrity you want me to write a shemale story for first!What's next? Scarlett Johansson Nicki Minaj Natalie Portman Britney Spears Jennifer Lawrence Margot Robbie Kate Winslet Kate Upton Keira Knightley Emma Watson Ka...

Open in Reader

The Shemale Possession

by SexyKate69 on Dec 12, 2018
Transgender & Crossdressers

I was in another day in the laboratory, arranging the experimental machines. It would be an ordinary day if it were not for one of the machines that went into overload and exploded, after the explosion I opened my eyes and I was scared to see myself stretched out on the floor. How could that be? There was only one explanation, I was dead, that's when I notic...

Pizza Boy Sissy Pt. 01

by BluntSlut on Sep 14, 2017
Transsexuals & Crossdressers

A fantasy fiction. ***** My name was Sam and I was a 18 year old pizza delivery driver. I just finished high school graduating early and started the summer working for Papa Pizzas. I had never really been a ladies man due to my non masculine body and long girl like hair. I was also really nervous to try to get with woman because I had a small penis. Becaus...