Huge Shemale Stories

130,457 results
Orientation
Length
Source
Infinite Scroll

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...

Call in the Professional

by xploring96 on Oct 15, 2017
Transsexuals & Crossdressers

The following story includes a transgender character, prostitution, Domination/submission, and derogatory terms used to humiliate. If this offends you please do not read any further. ***** How did Greg get here? It's election day in Washington DC and he is standing in the Ronald Reagan Airport with a big problem. To understand his problem it is important t...

Man Is Humiliated By Escort

by fun4all6969 on Sep 12, 2017
Transsexuals & Crossdressers

I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot to do with my wife's lack of a sex drive. I recently replied to an o...

Me & Miss Cocker

by sexlover on Sep 2, 2017
Fetish

A few weeks ago, I moved into the final year of school. Our English teacher had left at the end of the previous school year, and we had a new teacher, Miss Cocker. Now to say Miss Cocker is a babe is an understatement, she is about 6.2' tall and she has long voluptuous legs, which are usually stocking clad, blonde hair that goes just below her shoulders, b...

T's First Escort

by HORNYWRITERTS on Sep 26, 2017
Transsexuals & Crossdressers

I'd been waiting for about twenty minutes before the doorbell rang. Earlier that evening I decided I would finally take the plunge. I went online to Craigslist and, under the Casual Encounters Section, I found the list for Men Seeking Transsexuals and another list for Transsexuals Seeking Men. Of course, pretty much all of the ads were for escorts. A few ye...

Pool Party

by GuyIncognito06902 on Sep 26, 2017
Celebrities & Fan Fiction

Happy to share this story with you. This one is a bit odder than the usual fare and I warn you going in that this story involves well hung celebrity shemales. I kind of wanted to save it as a surprise twist, but that seemed a bit unfair to have the story seem like a typical lesbian celebrity story and then have it be about girls with hot cocks instead of cun...

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

Shemale Conquest

by standingstones on Sep 13, 2017
Transsexuals & Crossdressers

I decided to go out by myself one Friday night. I was tired of hitting the bars with my girlfriends so I thought I would go solo. I drove to one of the normal places we frequent. When I got there the place was packed. They had a dj playing loud music so I found myself a table to sit down for awhile. I was looking at the crowd when an attractive, black haired...

Commissions

by Rekki on Oct 27, 2020
Miscellaneous

A combined ensemble of all the public commissions I made in 2020. All the mentioned characters are 18 years of age.What's next? Red on White - Asami Sato x Blanca Vasquez Futa-TF Kimono The Spartan Finals Tracy and the Greenhorn Barbaric Love Lordran's loyal whore What's next? Red on White - Asami Sato x Blanca Vasquez Futa-TF Kimono The Spartan Fin...

Open in Reader

Fetish Pro Wrestling Ch. 03

by VexingVanna on Feb 3, 2020
Fetish

Hi everyone! This one is going to be a little longer -- I'm moving halfway across the country (America, that is lol), and getting settled in to a new area, culture, job, and everything else different that comes with moving to a place that's almost the exact opposite of where I was. I wanted to give you all something that might take a little longer to read, a...