Literotica Guy Has Sex With Transgender Friend Stories

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Life of a Bi Guy

by Samuelx on Dec 17, 2018
Transgender & Crossdressers

What's good, Fam? I'm Kelvin "K-Man" Wattford and I'm a man with a big problem. Alright, let's get certain things out of the way. I'm a Bisexual man, deal with it. I make it with females and with dudes, well, certain dudes. I don't like effeminate males, I find them annoying as fuck. Sorry, but I've got to have some standards. That's not the issue in today's...

The Adventures of a Gigolo

by Sacremas on Apr 22, 2025

AN: These are going to be a series of AI-generated stories, all of them featuring the same main character. Originally my plan was to generate AI images representing each client, but I failed badly at every attempt, and even the image above is just something I pulled from Google. I added a few images to a couple of chapters using Stable Diffusion but they a...

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Breaking Barriers Ch. 01

by NicoKleimachs on May 30, 2018
Novels and Novellas

0://Pre-Production Kip's Blog: I always knew I was different growing up. I know what they try to teach you in kindergarten, that everyone is different and everyone is special. That's not the kind I mean. I don't even mean the kind of special because I couldn't hear, and I was fitted with large, colorful hearing aids before I even nailed down the alphabet....

The Kingdom of Hafizar

by Samuelx on Feb 12, 2019
Transgender & Crossdressers

The Kingdom of Hafizar, which is bordered by Kuwait to the north, the Kingdom of Saudi Arabia to the South and is considered the smallest of the Gulf States, stands at the doorway of progress and peril. The Kingdom has a population of three million inhabitants, most of them centered in the three major cities, Al-Mokhtar, Behar and Thobar. Ninety percent of t...

Nick - A Transgender Woman's First

by VanessaTG on Sep 16, 2017
Transsexuals & Crossdressers

It is surprisingly complicated for an attractive transgender woman to find a man to fuck. At a singles bar, that mainstay of late 20th-century anonymous hedonism, a potential lover could take violent exception to having his heteronormative worldview challenged after he realizes he's been flirting with a woman who has a penis. Or, put another way, I feel tha...

Husband's Transformation Ch. 01

by Prematurelimphubby on Jun 10, 2019
Transgender & Crossdressers

Brett was sitting at home alone while his wife Mandi was gone shopping. It had been a few days since their last sexual escapades. He was horny and he wanted release. He went to the bedroom and opened Mandi's drawer. He loved her panties and wore them often whenever he was home alone. In fact, he's even wore a pair while she was home. They were relatively t...

More than Friends

by phoenixcinders on Jul 4, 2018
Transsexuals & Crossdressers

Chapter 1 Love and Learning the Hard Way It's hard to believe that I, Kevin Peterson, get to have Jessica Graceson to share a dorm room with. I know what you're thinking, why on Earth would any college allow a guy and a girl share a dorm room? Well, Jessica isn't an ordinary girl, she's spectacular. She's amazing! She's my best friend. She's the world to m...

The Departure

by MadQuill on Sep 16, 2017
Transsexuals & Crossdressers

Please remember this is a copyrighted work and all legal disclaimers apply. I hope that the story isn't affect by the grammar errors. I'm sure there are some errors and I do care. Thank you for your comments. ***** I was reviewing my Scotch purchase in Heathrow's Duty-Free zone prior to flying back to the States. Oban single malt whiskey here is less exp...

A Date with Destiny

by StarrOftheNite on Aug 20, 2018
Transsexuals & Crossdressers

Most people like to have a mind's eye picture of what the narrator of a first person story looks like, and since this is a true autobiographical story about my personal quest for gender identification, sexual orientation and self-realization, it's probably important to the narrative, too. Physically, then and now, I'm almost six feet tall, broad shoulders, n...

Becoming a Woman

by Dawns on Sep 13, 2017
Transsexuals & Crossdressers

It was about six in the evening. An hour had passed since I came home from Walmart where I had been working for the past four years. The eight hour shift at cashier passed quickly. A large number of buyers came bye my register. My shower had been adjusted to the lukewarm temperature that I like and lasted some five or six minutes. Standing in front of the b...