Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

The Greatest Liar Ch. 02: Exposure, Disclosure

by alexandrarios on Jul 2, 2019
Transgender & Crossdressers

Author's Note: This is a continuation of the narrative which commenced with "My Awkward Phase", which I posted here previously. Readers may wish to read that before continuing, although I have written them to stand alone. ***** Natives say that life cannot exist in LA without a car and money. My last days in LA proved those truisms. I'm from Brentwood, "...

Cockatoo Pt. 21

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback. ***** Following the call to Kritsada, I stayed in Cockatoo, chatting to Nin who had brought me another beer. I asked her to join me for a while, and we talked about last night. She had really hated Tony and was delighted with what we had done. I was quietly impressed; she was pretty, her English was excellent, had a great sense of humo...

Cockatoo Pt. 19

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

I live for feedback. ***** I stopped dead in my tracks, 'What did you say, Pao?' 'Miss Sam, she meet the man. The horrible man. Nin follow him and saw them talking.' 'Was Nin sure it was Sam?' 'Yes, Mr James, she said she saw them clearly outside hotel he staying.' I couldn't believe it. What the hell would Sam be doing with this creep? Areeya was now...

Sex Zoo 2.2: Entry 04

by JMaxwell69 on Sep 13, 2017
Sci-Fi & Fantasy

I was walking down a bright white arc of corridor absent-mindedly fingering the scar on the back of my head. It had to have occurred since I arrived here, but my hair had been much longer and my memories of my past life were fuzzy. I was trying to recall whether it could have happened during that vaguely remembered period that I continued to think of as my r...

Pleading Her Case

by griffin57 on Sep 15, 2017
Transsexuals & Crossdressers

Drew was finally warming up. It had been a long, cold day cutting firewood up by the Dam road. But his trailer was full and he was on his way home, attempting to beat the snow storm that was forecast. Three inches had already fallen and there was no end in sight. Predictions of close to a foot of the white stuff peppered the news on the radio and he was look...

Minimum Security Prison Bitch

by JonThomas_ on Dec 19, 2018
Transgender & Crossdressers

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows? As my regular readers are aware, I enjoy writing about the transgender experience from different perspectives. Here I write about a transgender woman whose experiences in prison were quite different than she expected them to...

Handcuffed at Dawn

by mpqm1968 on Aug 19, 2017
Erotic Couplings

The urgent sound of the hooter reverberated through the open window as Yvonne's tongue and lips worked slavishly on my cock. "The taxi's here," I clarified in hoarse tones, catching the look as my fiancée glanced up momentarily. It was a look that said: you're not going anywhere in a hurry – and she was right of course. Steadying myself on her head, strokin...

Without You I Have Nothing Ch. 27

by JAScooter on Sep 15, 2017
Novels and Novellas

'Friends of the Sydney Symphony Orchestra request the pleasure of Mr. & Mrs. P. O'Brien.' The invitation had arrived weeks earlier and reluctantly Peter had accepted. Immediately after Christmas, they flew to Sydney and Jennifer went shopping for an evening gown by herself. She adamantly refused to tell Peter what she had purchased or to model it for him....

Hung Trans Lesbians Fuck Two Ladyboys

by mrstanley on Jul 15, 2020
Transgender & Crossdressers

I haven't written a Trans story this year. In this story I try to describe more intimate intense scenarios with a wider variety of details. If you enjoy the story please vote and comment. Feel free to read my Fetish and Mature stories as well. Note 1: If you like Transsexuals, Trans Lesbians, Asian Ladyboys, Big Cocks, Extreme Cock Sucking, Anal Fucking, A...

She-Male Babysitter

by sirhugs on Sep 28, 2020
Transgender & Crossdressers

[Note to Readers: This is not a story with quick short sex scenes, so if that is your goal, it might not suit you. There are detailed sex scenes, or one long detailed sex scene, take your pick. The use of the infirmary apartment setting is an homage to John Irving's The World According to Garp, which otherwise shares nothing with this story. My thanks to Car...