Site:literotica.com "kept My Penis" Transgender Stories

4,372 results
Orientation
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Infinite Scroll

Welcome to Transaton City

by tslover69 on Apr 22, 2025

[This is a story game. so please click START GAME on the right hand menu otherwise none of this will make sense! Plus you will be missing out on the best part of the game!] A new town, a new start. That's what was on your mind as you drove past the "Welcome to Transaton City". You were headed to Transaton to get a fresh start after the last rough c...

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Tanya: Algonquin College Days

by Samuelx on Oct 15, 2017
Transsexuals & Crossdressers

"Hello," I said to the tall, curvy, bronze-skinned, dark-haired and curvaceous First Nations/Native American cutie, and she looked me up and down, pretty face oozing with attitude, and said nothing. Haughtily she walked out of the Loblaw's store, carrying herself like a queen or something. Big ass plus attitude equals irresistible in many a Black man's lexic...

Katsumi Nakasone of Japan

by Samuelx on Mar 7, 2018
Transsexuals & Crossdressers

"My name is Katsumi Nakasone-Hollander, but everyone calls me Kat," the tall, curvy, raven-haired, thirty-something Asian American businesswoman said with a smile. Jacques Moulin and his wife Renata Urbano-Moulin looked at her and nodded. They were in the City of Randolph, Massachusetts, at the headquarters of Nakasone-Hollander Realty. Interesting pair, Kat...

Eloise's Journey

by karen1947 on Oct 2, 2017
Transsexuals & Crossdressers

This is a fictional story. It is written from Eloise's viewpoint in first person. ***** 1. Hello all!! This is Eloise Schmidt. I haven't always been Eloise. I was named Brian at my birth. But by age 4, I found I liked to play with my Barbie dolls and wear Wonder Women underwear. I had an older sister (Emma) who loved to have me join her at tea parties...

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...

From Family Man to Bottom Bitch Ch. 02

by esclaro on May 18, 2020
Transgender & Crossdressers

In the years following my virtual encounters with Isabel, I felt driven to explore my attraction to transgender women. After seeing her and talking to her over the years, I knew that I would never be fulfilled sexually until I could realize my deepest desires. Desires which I never even knew that I had but which were now obvious and undeniable. What were t...

From Family Man to Bottom Bitch Ch. 03

by esclaro on May 18, 2020
Transgender & Crossdressers

After a couple of years chatting and jerking off with webcam girls, I was ready to meet someone in real life or IRL as it was known in the chat rooms. I had asked the model from Singapore if she would ever be willing to meet me and she said yes, but she disappeared before I was ever able to make arrangements to do so. It gave me some ideas that it was possi...

Bandalore

by 12inpen on Mar 31, 2018
Fantasy

{if isPlaying = true} Loading Creation Software Loaded Welcome to Bandalore {if enableSound = true}#so{soundID}{endif} {else if isPlaying = false} This story uses a custom Extension and the scoring system to ensure a more interactive and customized experience. To play properly you will need to use Google Chrome on a PC and have the Bandalore Editor Extens...

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Population Control

by protoborg on Apr 29, 2025

8.08 billion people. Not enough resources. Something needs to be done. Let's see how we can take care of this. Infertility, limited number of children, more homosexuals, more transgender people, lowered sex drive, more asexuals, more eunuchs, more nullos. Lots of solutions, not enough action. More than one person has tried to fiddle with the world's populati...

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The Bet Ch. 03

by MutableMalachi on Sep 15, 2017
BDSM

Allan released me from the bonds connecting me to the Cross, supporting me as I stepped free. I tried to shake him off, insisting I was fine - the whole scene had only lasted a few minutes, and I hadn't done anything - but he held firm. Once we started to walk, I realized to my embarrassment that I was not fine. My knees felt like jelly and my head swam. Cha...