Transsexual Fucks Guy Stories

150,484 results
Orientation
Length
Source
Infinite Scroll

Mistress Raven Black

by Samuelx on Oct 29, 2018
BDSM

"You're either dominant or you're not," Raven Black stated, speaking to the camera. On her blog, which was followed by tens of thousands around the world, the young Black woman spoke about her experiences as a professional dominatrix, the state of the affairs between Black men and Black women, and her private life. The videos that Raven Black made were quite...

Tiffany's Deal Ch. 02

by MicheleNylons on Jun 24, 2019
Transgender & Crossdressers

Chapter Two - The Flop Tiffany's earliest memories are of her as a young boy growing up in the Midwest. To say that her upbringing was difficult would be an understatement. Although not particularly small for his age Tom Robinson was very lithe and almost effeminate in manner. From the outset Tom knew he was different. He began to feel trapped in a body in...

Bostonfictionwriter's Big Bash Ch. 02

by BOSTONFICTIONWRITER on Sep 13, 2017
Non-Erotic

Look at this, the ones from my story Beautiful Betty, who made the biggest stink about attending, are the first ones here. Do you believe it? "Hey, Betty, you look very beautiful, as always. Davis, thank you for coming, it's nice to see you." "Take your dirty paws off my woman, Freddie, or I'll deck you and stomp you to death, you hack!." "Listen here, Da...

Secret Affairs

by kinkygeek on Jul 5, 2016
Cheating Spouses

You have been married for about five years now, and all this time you've managed to keep a string of affairs going on the side. As far as you know, your spouse has been completely faithful to you and has no idea you've been having sex with anyone else. You love your spouse dearly, and you two still make love passionately at least once a week. However, you ha...

Open in Reader

The First Time

by rampe on Sep 16, 2017
Transsexuals & Crossdressers

If you have read my stories before you know that I'm Finnish guy who doesn't write in English as well as someone who is from an English-speaking country. So, I apologize beforehand about my mistakes or odd lines. Without good editor helping me I couldn't publish this story. So thanking her very much! My stories consist of some elements that many can think of...

Shemale Becomes Friend

by refinedexperiences on Sep 12, 2017
Transsexuals & Crossdressers

Last month I was working a dating site with little satisfactory results when I finally got a response from a girl. She was 6 feet tall and blonde. She seemed to have a nice figure and seemed very very athletic. I played basketball in high school and am pretty trim, although all I do nowadays, as an adult in my 20s, is go for runs on the weekend. Still, I lov...

Bad Romance At Carleton U

by Samuelx on Sep 12, 2017
Transsexuals & Crossdressers

When a man stops lying to himself and rejects the lies told to him by others, he will find life much simpler. My name is Charles Joseph. My friends call me C.J. and I'm a young Black man of Haitian descent living in the City of Ottawa, Province of Ontario. I was born far from Canada, in the Caribbean island of Haiti. My folks and I moved to Canada eleven yea...

Jasmin wears the pants Ch. 02

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

In Part 1 of "Jasmin wears the pants" our hero is fascinated by a woman and in the end of the chapter he is waiting in front of her door just wearing his briefs. Thank you very much for all the positive feedback. I really appreciate the praise. Once again people who don't like TG stories and or are under aged shouldn't read on. All rights are reserved. If so...

What an Amazing Life - My TS Lover

by AmazingLife on Sep 14, 2017
Transsexuals & Crossdressers

Thanks for clicking on this story. I have been trolling around Literotica for a couple years now, mostly downloading stories to the hard disk of my notebook, to fuel my masturbatory fantasies while I am on the road. Probably like most of you, I am someone that people of the opposite sex never seem to pay attention to when passing on the street. Family gene...

From Kazakhstan with Love

by Samuelx on Sep 16, 2017
Interracial Love

Tell people that you're from Kazakhstan and they stare at you blankly. Same country Borat claimed to be from in that awful movie, I usually say, groaning inwardly and idiotic smiles immediately follow. Now they get it. Cultural relativity isn't a concept most people in North America can grasp. My name is Rashida Jabayev and I was born in the City of Kentau,...