Shemale Fuck Guy Stories

265,604 results
Orientation
Length
Source
Infinite Scroll

Realization vs. Reality

by Throckmorton on Dec 24, 2019
Transgender & Crossdressers

This story is one hundred percent true to the best of my recollection. I wanted to tell someone for so long, but never have, until now. Feed back is appreciated, and applications are being accepted. Read the story, you’ll understand. To get to the story… So…here I sit. 40 years old and revisiting the confusion of my youth. I am, and always have been, a fir...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

Open in Reader

The Neighbour Who Had It All

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

Not my usual fare, if I have enough stories to be considered usual. Shemale, transsexual, chick with a dick, whatever you want to call it, it's here, so fair warning. I'd also consider it a bit of a romance story, though not a straightforward one. There's also some master/slave, not very much, it's more a hint of where their relationship will probably go i...

Amatuer Strip Night Ch. 02

by Travel_by_day on Sep 16, 2017
Transsexuals & Crossdressers

Sasha stood in her bra and panties looking nervously out over the crowd at the topless strip club. She shuffled her feet and looked down, her blonde hair covering her face and she wondered to herself if coming back out onto the floor had been a good idea at all. Sasha had just won first place at the topless bar's amateur strip night, putting on a rocking co...

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...

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...

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...

Shemale Subway Sex

by Travel_by_day on Sep 13, 2017
Transsexuals & Crossdressers

I was out at a dance club with some friends on Saturday night. Clubbing isn't really my scene though, and I soon found myself very bored. Looking at my watch, I saw that it was almost 1 o'clock in the morning. I was having an awful time, and if I didn't leave then, I would miss the last subway train and have to take a $50 cab ride home. So I said goodbye to...

Erin and the Shemale

by kimberlykitten on Sep 25, 2017
Transsexuals & Crossdressers

Erin was up bright and early on Friday, getting a good hour jog into her schedule. She didn't have to be in class until two hours from now. As she was jogging, earlier male joggers had passed her by with their eyes directly on her bouncing melons. Even wearing two sports bras and two regular bras weren't enough to hold Erin's gargantuan jugs down. Erin did...

Accommodating Neighbors Ch. 04

by gentlegem on Sep 14, 2017
Mature

Chapter 4 Our Visit to the Adult Toy Store (Authors Note. This is the 4th story in a series. For those of you who haven't read the first 3, it is based on the relationship of a 44 year old red haired lady and a 63 year old man who live in the same apartment complex. Much of it is based on true characters and events.) * Becca and I didn't see each other f...