Ladyboy Fuck Guy Stories

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Orientation
Length
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Infinite Scroll

Mistress Styles and the Humbler

by justincbenedict on Feb 26, 2019
BDSM

Styles. who'd gone by surname only since her Army days, smiled as she looked at her unfortunate husband, the ex-playboy Busby Letourneau. Busby moved uncomfortably on the hard kitchen stool. The seat was so small and of course his hands were tied behind his back, and it was a delicate balance. Styles stroked her husband's engorged cock and grinned, her ton...

Lin

by goldbloke on Sep 13, 2017
Fetish

It's time. Time to make my fantasy a reality. I book a flight to Thailand for the next day, only a cheap one to Bangkok International; I'll worry about a hotel when I get there. I land in the early evening and waste no time putting my plan into action, taking a cab to Pattaya as soon as I arrive and seeking out somewhere that manages to blend the seedy wit...

Cockatoo Pt. 43

by nikkiesilk on Oct 8, 2018
Transgender & Crossdressers Stories

Chapter 43 "Shoot him." Aki's voice bounced around the walls of the garage as I stared down at the gun in my hand, unable to grasp what was happening. Aki stood behind me, wrapped my fingers around the stock and pushed my forefinger through the trigger guard. He held his hand over mine and pointed the pistol at Jandaeng. "Shoot him and you will be rid of...

Midnight Ch. 02

by virtualatheist on Sep 15, 2017
Romance

Still no sex, sorry - VirtualAtheist ***** Over the next couple of weeks, I saw Alan and Erica here and there. We met up for a coffee at Starbucks in the city centre and one evening, Erica and Alan had me over for dinner at her flat. That was when I saw she had a complete DVD collection of Star Trek, The Original Series (digitally remastered), The Next Ge...

Marion Turns Me Round Ch. 04

by jomar on Aug 30, 2017
Transsexuals & Crossdressers

You might want to read the earlier chapters for a bit of context.... On the other hand, you know what you're in for here. I hope you enjoy the kink, baby. ***** Earlier in the day Marion had my hair styled, made me up, decked me out in womanly attire and accessories then thoroughly fucked me on her elegant leather couch. It was now early evening. And it...

Cockatoo Pt. 01

by nikkiesilk on Sep 14, 2017
Transsexuals & Crossdressers

I live for feedback. ***** It's a cliché, isn't it? Man comes home early and finds his wife in bed with someone else. Only slightly less of a cliché in my case, as the 'someone else' was my wife's closest girlfriend - closest in every sense of the word. It was a quick divorce; no kids, only a rented flat, so the only squabbles were about books and cds. In...

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, "...

An Opening to Be Filled

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

Aki was stroking me, her fingertips were lightly touching my small stiff member, hers too was stiff with lust for me. She had pushed my blouse up over my small breasts revealing their swollen nipples to the cool night air, her kisses upon them had left them stiff and turgid. I reciprocated with her bigger breasts, freeing them from restrictive clothes, sighi...

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...

Without You I Have Nothing Ch. 28

by JAScooter on Sep 15, 2017
Novels and Novellas

Resuming his position at the kitchen doors, the old Chinese carefully controlled the waiters as they successfully served Dingo's guests. Then, tiring of the charade, he turned, pushed on the swinging doors into the kitchen and grunted an order in Cantonese. Carrying a roasted pig's head on a huge platter, two waiters appeared. They followed the old Chinese...