Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

Caught with Consequences Ch. 03

by MicheleNylons on Jul 13, 2020
Transgender & Crossdressers

Chapter Three -- Truth and Consequences The package arrived overnight and was waiting for Adele when she arrived early at the office. It was a plain brown padded postage bag with no markings on it. It was addressed simply to Adele Edwards and marked urgent. Adele put the package down on her desk and deliberated. She guessed what was inside it and she knew...

The Square Peg Ch. 08

by icedragonmo3 on Apr 15, 2020
Transgender & Crossdressers

Disclaimer: Welcome to chapter 8 of The Square Peg. This story contains a relationship between a mtf and a ftm. Things don't always go perfectly. If you haven't read the previous chapters, much of this won't make sense. Vonnie goes by the name Kevin at school and at home, and by Veronica at work. Drew goes by Andrea at school, and his dad sometimes calls him...

The Girls Across the Hall

by NatureSuperal on Aug 7, 2018
Transsexuals & Crossdressers

"Relax. Trust me. I know what I'm doing. I really enjoy doing this. You're going to love it." As it turns out, she was right. But, I'm getting ahead of myself, no pun intended. Best to start at the beginning. My name is Chris. I am 20 years old, six feet tall, 170 pounds. I just graduated college and was starting grad school in the fall, so I had a summer...

Is he a He or a She

by uksnowy on Sep 16, 2017
Transsexuals & Crossdressers

"Again darling," moaned Ji Su. "But harder and deeper this time," she twisted her neck back at me and told me urgently. "Fuck me sweetie you've worn me out already. Twice this morning, once after lunch then now and it's not bedtime yet," I panted, slamming as best I could at her delicious upturned rump. My hands gripped her hips, her back already running w...

Janet's Night Out

by JanetHarper on Sep 16, 2017
Transsexuals & Crossdressers

This is the follow up to Silent Night, Hot Night. To the few who expressed interest in the next chapter, I apologize for it taking so long. I'm not a very quick writer. Special thanks to Whordinarygirl for editing the story and her helpful suggestions. ***** New Year's Day had come and gone. The excitement of the holidays had faded with not much on the...

Up the Cuts

by TransPunkPrincess on Sep 18, 2017
Transsexuals & Crossdressers

Author's Note: This story was written by a transgender woman, with other transgender women as the intended audience. If that isn't you, then this is probably going to seem like a big departure from most of the stories on this site, and there may be some vocabulary or situations that are unfamiliar to you. Don't tell me about them. Google is your friend. Con...

The Flaming Girls Ch. 01

by MicheleNylons on Mar 2, 2020
Transgender & Crossdressers

Chapter One - Better off Dead Charlie Ringwald put a Consulate menthol cigarette between her lipsticked lips and lit up, drawing the smoke deep into her lungs. The smoke gave a false illusion of warmth on the bitter foggy night. She put her cigarettes back into the cheap handbag hanging from her shoulder by the thin vinyl strap and wrapped her arms around h...

Truth or Fantasy 18: My wrap-dress

by 1sfshermale on Apr 22, 2020
Transgender & Crossdressers

It was an unusually warm late winter, early spring day. Freeing. Liberating. Enough of those heavy winter coats and boots. Enough of the scarves and gloves. Enough of being cooped up and encumbered under layers of fleece. I was overcome with the need to go out. I went to my closet to remind myself what I had in the way of lightweight outfits. I am thinking...

Enlivened Dreams Pt. 01

by SAR1995 on Jul 13, 2020
Transgender & Crossdressers

I looked around the room that has been my entire life for the last 18 years. The smell of fresh paint wafted through the air. I spent years drawing all over those walls. Since my parents were going to rent out the room once I left, it needed to start anew; like me. I started transitioning around the time I started high school and I had only gotten better at...

Big Flipping Deal Ch. 02

by IanSaulWhitcomb on Sep 25, 2017
Transsexuals & Crossdressers

[The story so far: Nick has inherited one half of a house from a sweet old lady neighbor, the now-deceased Mrs. Pinobscott. In a posthumous attempt at matchmaking, Mrs. P left the house jointly to Nick and her niece, Lindsey, a smoking-hot blonde whom Nick quickly becomes infatuated with, despite Lindsey's insistence that he doesn't want to get involved with...