Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

Finding Dana

by PedalPower on Sep 16, 2017
Transsexuals & Crossdressers

It would always happen, without fail. I'd begin jacking off to regular, everyday porn, like everyone else. A man doing a woman, maybe two. Sometimes two women. Sometimes a woman on her own. But it never ended with that. The same thing would always happen — I would only come from watching a transgender girl. On the porn sites, they called them "Shemales." I...

Sarah had Sex in an ABS

by SarahCD on Feb 12, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

Sarah Visits Las Vegas

by SarahCD on Feb 26, 2019
Transgender & Crossdressers

I went to a business conference in Las Vegas. I had chosen to stay in a different hotel from the rest of my party since I wanted to build reward points with this hotel chain. Later, I was able to use them for a hotel room at the Paris Hilton in Paris. Without points, it would have been $600 a night. Being in a different hotel ended up having another major be...

Magic Dress - Diana Pt. 02

by SlightlyRude on Apr 23, 2019
Transgender & Crossdressers

MEET THE GIRLS We were told to come early, and I could change into my outfit at Jason and Lucille's house. Lucille greeted us, looking very pretty and very feminine. She could easily pass. We went upstairs with our bags, and I was transformed in my favourite green dress. When we came down there were another couple of women. One had a big bust and quite cu...

Dena and Annie Pt. 03

by daisyboi_sissy on Dec 24, 2019
Transgender & Crossdressers

This story is a complete work of fiction and is only to be taken that way. If Transgender sexual ideas offend you then do not read. If you are not above age 18 then you should not be here anyhow. ***** "Come on sexy let's see what Dena has for the camera! Make some man want to rush over and ravish that little body of yours. I begin posing around the bathr...

From Family Man to Bottom Bitch

by esclaro on May 12, 2020
Transgender & Crossdressers

If someone had told me that one day I would be sucking on a seven inch cock like a starving puppy and happily slurping up the cream from that cock, I would have shaken my head in disbelief. If someone had then told me that I would be offering up my asshole for that same cock to fuck and begging for a fresh load of cum deposited deep in my rectum, I would hav...

Groupie

by Dar_Jisbo on Oct 6, 2020
Transgender & Crossdressers

*All characters in this story are over 18 years old.* [2 years post-COVID] I was super-thrilled. My favorite band, the punk group Eleven Deadly Evelyns, was going on tour again and their first stop would be my city. They had formed right after the pandemic had finally ended and had quickly become an international hit. I immediately bought first-row ticke...

Dr. Awful

by JonThomas_ on Oct 31, 2018
Transgender & Crossdressers

Greetings all; the characters in my stories exist in my head, but there might be real life inspirations for some of them. Who knows? Anyways, my regular readers know that I enjoy writing about the transgender experience from different perspectives. Here I write a three act play about a straight man that is made into a transgender woman without his knowledge...

Sleeping Beauties Ch. 03

by MicheleNylons on Dec 3, 2019
Transgender & Crossdressers

Chapter Three - Teacher's Pet Felicity Kendal burst through the front door with her two excited daughters right behind her. They had come home from church to find their father's car parked in the driveway. "Daddy!" the girls called out in chorus. Michael Kendal rushed out of the kitchen where he had been waiting and hugged all three of them and kissed his...

Tgirl Blind Date Surprise

by sethp on May 7, 2019
Transgender & Crossdressers

This is a transgender story. If you don't like that, then stop reading now. If you've read BBW Blind Date Surprise, you'll find that this story is a riff on that one. Consider this an experiment. It's almost identical in plot, and dialogue with a few obvious differences. Hope you enjoy it. Special Thanks to EmmaTG and Holly and Salina for their input. But le...