Transgender Stories

4,333 results
Orientation
Length
Source
Infinite Scroll

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...

Magic Dress - Serena

by SlightlyRude on Dec 3, 2019
Transgender & Crossdressers

Note: The early part of this story can be found in Cream and Lace. ***** CHAPTER 1 It was the biggest surprise I had ever had on a birthday, and it turned out to be the best birthday present of my life. My darling wife Samantha bought a dress for me. To some extent it should not have been such a surprise. My brother Frank was staying with us, and he like...

Sarah Gets Soaked and Meets a Girl

by SarahCD on Dec 18, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. *** I was on vacation in Florida. On the second day, I decided to visit the 'glades. I wore a matching red bra and panty set, with a...

Letter from Montgomery

by justincbenedict on Sep 24, 2019
Transgender & Crossdressers

Dear Shoeblossom, I didn't think there were any transgender men in Alabama, but apparently my husband and I got one as a client! This little convo was funny and somewhat arousing to friends of mine, so thus, I submit it. Syndi "Oh, thank you for letting me out, Syndi." "How was it, Won Joo? Let me sponge off those perky tits of yours." "Oh, that feels 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...

Rachael Ch. 05: The Audition

by SallyRichmond on Sep 28, 2020
Novels and Novellas

Chapter 5 The Audition Madame Silver had seen Rachael before she had her audition with Lisa. This would be the determining audition for Rachel and they both knew it. Rachael did not feel particularly nervous because of the recent sex with Lisa and not on edge due to the wine. She did, however, want to do a good job. Madame Silver having just been with a cl...

Rethinking Bisexuality

by WickedWick on Mar 13, 2019
Reviews & Essays

Every few months, we have an article come out that talks about Celebrity X who has decided that they're no longer bisexual and now straight (or gay). Then there are the articles critical of big media for labeling bisexual celebrities as gay (despite what the celebrities have said in the past). And let's not forget the articles about sciences struggle to "pro...

Glass Bauble

by AlexiaAlexander on Dec 10, 2018
Transgender & Crossdressers

Being secretly Transgender in a rural area can be frustrating. I live a life of quiet desperation and a whole lot of masturbating to porn. Reading and watching transformation stories stir my imagination for my own dreams. Finding a weird glass purple gem allowed dreams to become reality. It all started at the Flea Market. I was really on the low money side...

Accepted Ch. 04

by JustThots on Oct 16, 2018
Transgender & Crossdressers

This is the continuation of Sasha Milovic. I know it's been quite a while since Chapter 3, but fear not! I have not forgotten about Accepted, life just happens to get in the way sometimes. I've worked on Chapter 4 for quite awhile, but the world outside of the internet just wouldn't let me finish it until now. I hope it was worth the wait, and thank you for...

An Unexpected Sex Change

by cds6 on Sep 16, 2017
Transsexuals & Crossdressers

The night was just starting and I had just gotten downtown with my girlfriend. She is a cute brunette with a great body and is, obviously, completely in to me. I'm a good-looking guy, around 5' 6" with dark hair, brown eyes, and a slim, but somewhat defined physique. I'd say we're good for each other. This night, we decided we'd like to get some drinks and...