Transgender & Crossdressers Stories

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Infinite Scroll

Meadows

by Dar_Jisbo on Sep 23, 2019
Transgender & Crossdressers

Thank the deity of your choice for Moore's Law. By 2030, computers were bumping up against the speed-of-light limit, but thanks to technological breakthroughs making the circuits smaller, as well as advancements in parallel processing, Moore's Law continued to hold. And by 2035, we'd reached "the singularity", where computers (androids, actually) could des...

I Adore Crossdressers

by Ab9095 on Nov 26, 2018
Transgender & Crossdressers

I adore crossdressers. Adore!! Pretty little pantied asses up in the air. Shaved dicks and balls hanging down. Pretty little assholes. Fuck Yeah!!! I love seeing their hard dicks flopping when they are riding a cock. Fucking A, when they are hot they are HOT!!! They don't have to be perfect any more than any woman does. They are ALL good. But I do love it...

Slide

by Dar_Jisbo on Mar 16, 2020
Transgender & Crossdressers

I looked at the e-mail. Another request for my tutoring services. I'd developed quite a reputation in the city. I sent a reply asking for the usual details. Tracy, age 22, wanted help with advanced mathematics. She was living in a small apartment nearby, lived alone, and was a first-year graduate student, having completed her undergraduate work the year be...

Jeff Explores His Fantasies

by majorpayne_1342 on Apr 13, 2020
Transgender & Crossdressers

It has now been nine years and I never thought things would turn out the way it did. At first, I was skeptical because this was a whole new experience that I've never heard of. However, the more knowledge I received about it, the more excited I got. It brought out of me a desire and a passion hidden inside that was begging to come out. It all started with a...

Freaky Behavior

by Dar_Jisbo on Feb 12, 2019
Transgender & Crossdressers

Boredom and curiosity are powerful forces. I'd been wondering what sex with a transgender woman would be like. Not enough to actually try and date one, that would require putting in more effort than I wanted. I had never actually dated a cisgender woman either. Any time I wanted to get my rocks off and didn't feel like jerking it to porn, I would just hire...

Are You a Sissy?

by dominantdadddy on Sep 26, 2017
Transsexuals & Crossdressers

There I was, early Friday evening, standing on the front steps of my co-worker, Liam's house. As instructed, I brought with me a small overnight bag with the following items: a toothbrush, toothpaste, razor, shaving foam, and flip flops. I was nervous. I was not sure what was in store for me. But I had an idea. On Tuesday, Liam had called me into his off...

Breeding Natalia

by sweetsatine on Jul 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Nathaniel Geller had been a young, up-and-coming salesman at MedZ who'd shown great potential. In just a few years, he made his way from ambitious college graduate to savvy junior manager. Risky ventures that others were skeptical of luckily always seemed to turn out succes...

Hotel Surprise Temptation

by Subman666 on Jul 15, 2020
Transgender & Crossdressers

The best visit to Chicago, my hotel bar fun, and juicy Italian Steak Sandwich. During my last trip to Chicago, I made sure to leave time to get out, see some sights and get a local Italian Steak smothered sandwich. The real purpose of that Chicago trip was to learn about some of our company's new software products. We spent about 8 hours each day, testing...

Crossroads

by Dar_Jisbo on Feb 4, 2020
Transgender & Crossdressers

It began - of all places - with a random video on a porn site. I stumbled across the video - a solo performance by a sexy blonde transgender woman - and posted a comment on it. My comment: "Your boyfriend must be a very lucky man. You're gorgeous." Her reply: "I don't have a boyfriend. :( Thank you for saying I'm gorgeous." She had a personal website. I c...

Just Look at Me Now Ch. 03

by GFfan on Apr 13, 2020
Transgender & Crossdressers

Eager as I am to tell you about my first crossdressed Halloween with Jude and Becky, I must save that for a later chapter and fill you in on some major developments that occurred as my first summer of feminization ripened into autumn. Surrounding these landmark events were patterns of submission we had established early on. I wore panties 24/7, and I shoppe...