Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

First Suck

by mercury7259 on Dec 10, 2019
Transgender & Crossdressers

Donna I'm sitting here looking out the window, seeing, but not really looking. My mind is racing, not being able to single in on any one particular thought. I see puffy cotton ball clouds and a radiant blue sea as the voice comes on and says "We'll be landing in Manila in 30 minutes. The current temperature is 86 degrees and clear. We hope you have enjoyed...

The Island: Introduction

by ReturnoftheCapnCock on Oct 6, 2020
Non-Erotic

I didn't know what this remote island in the Bay of Thailand or its institute would bring me. I didn't know where life would take me. But I knew that I was in for an adventure of a lifetime that I would, hopefully, recall fondly. This is my story of my time on The Island. I will be writing about "my" erotic adventures in this series. Sometimes, I will write...

Surreptitious Love Ch. 57

by BenGarland on Sep 14, 2020
Erotic Couplings

CHAPTER 57 -- A NICE SURPRISE Nguyet asked me last Monday short and crisp—using her full name again from her office email—if I was interested in another meeting with her. We had role-played that I was interested in the cookie-cutter houses her company was selling, and the first house viewing—our last role-play—had turned into a two-hour-long ribald rumpus,...

Addicted to Pream's Cream Pt. 02

by Vodka_Jim on Sep 26, 2017
Transsexuals & Crossdressers

Author's Note: I'm sorry it took me so long to complete Chapter 2 of this story. I plan to be more regularly submitting stories. I have a couple more in the works and then will probably come back to the Pream story line. I hope you all enjoy. I welcome your comments. *********************** My heart is beating so hard in my chest that I can almost hear it...

She Sucks She Cock by the Sea Shore

by FredTR on May 21, 2019
Transgender & Crossdressers

It felt like it had been years since Liz had been able to take a day and just relax. Her first year at college had been a whirlwind of papers, tests and classes. And her job at the bookstore. Sure she'd gotten laid a few times (okay, maybe more than "a few" times), but that just seemed to stress her out more because she always felt guilty and worried her boy...

My First Ladyboy Ch. 02

by 69plus1 on Sep 19, 2017
Transsexuals & Crossdressers

We had just fucked ourselves senseless and Billi was leading me to her shower. After she adjusted the temp we got under the spray. First off was to clean my cock of the lube and cum. I leaned back to the shower wall and spread my legs like a slut as she covered me with soft soap from cock tip to balls and back to my ass. I was sexually spent but she easily...

Marion's Turn Ch. 01

by jomar on Sep 13, 2017
Fetish

I stood in the foyer. She was gorgeous. Hair up, dressed in black; corset, stockings, panties, high heels. And a strap-on. "You really gave it to me good last month, baby. I didn't expect those other guys. At first I was a teensy bit mad...but I gave into it and I couldn't get enough cock, could I, baby. Mmm, those cocks in all my holes, all slippery with...

Letter from Sherier Place

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: I am a member and Substitute Treasurer of the Keeplock Club, a select group of women who keep their husbands and significant others in chastity belts. Our oldest member is seventy-eight, the youngest, a college junior. It's a constant vigilance, and I thought you might find it interesting, as your column discusses much of this. On Wednesd...

The Booted Barberess Ch. 03

by trasaro on Sep 16, 2017
Fetish

After some fantastic leather-clothed and booted sex, I was about to take the lovely Emma out for a pub supper at "The Stag in Rut" in Bodling. I had only met her earlier that day at the barber shop in Bodling, where she worked, when she had given me rather more than a haircut. We had quickly realised that we shared a number of fetishes, including boots, leat...