Transgender & Crossdressers Stories

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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...

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...

Safe Place

by Dar_Jisbo on Oct 31, 2018
Transgender & Crossdressers

[Two months into the Second War Between The States, which began after the results of the 2020 elections were in and the Democrats added to their Congressional majorities and retook the White House, President Sheldon Whitehouse took office. As his first act, he proposed that the country be split into the New Confederacy, in the Southeastern region, and Americ...

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...

Allen

by IRivera719 on Dec 25, 2019
Transgender & Crossdressers

Allen shaves, his eyes focused, the lights of the bathroom vanity dancing as he does the practiced moves for the umpteen-millionth time. He still enjoyed it and he enjoyed the fact that each morning presented him with a very male challenge. Last few touches and he rinsed the razor, rinsed his face, looked at himself in the mirror and smiled. He was nude, his...

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...

Jacqui/Jack

by wife2hotblk on Sep 16, 2017
Transsexuals & Crossdressers

My name is Jack. It used to be Jacqueline, but that was a lifetime ago. My forty-ninth birthday is next Friday, but I have actually only been living for the past five years. I am what they call a transman or female-to-male transsexual. As a child, my life was pretty perfect. No divorced parents, a nice middle class neighbourhood. No one seemed to notice or...

My Sexy Woman

by Rayy69ruizz on Sep 14, 2017
Transsexuals & Crossdressers

I was 19 fresh from high school as starting college. I had girlfriends all throughout high school I decided to take a break from dating. One day I was browsing through the web on social media, MySpace, to be exact, when I got a friend request. It was from a beautiful woman. She had a beautiful body, her skin looked smooth and very tan, had very erotic body....

Autumn by Marina Ch. 02

by ashleyw_xoxo on Jun 8, 2020
Transgender & Crossdressers

The next day was agony waiting to go out with Marina again. I tried to pry into what she had planned for me, but all she said was "just drinks and then some time at my place". So I met her at her place at 7pm, and we went to the bar nearby. After three drinks (probably 5 for me as I always seemed to be finishing hers for her) we went back to her place. "So...

Friends to Lovers

by awpbmn on Oct 22, 2019
Transgender & Crossdressers

All characters depicted are over 18 years old. *** She enters, stripped to her bra and panties, and sees him sitting at the edge of the bed in only his boxers. He admires her supple, athletic body, her womanly hips, and her large breasts. He had imagined her body so many times. He had known her since childhood, he had watched her develop alongside him, had...