Ladyboy Stories

221 results
Orientation
Length
Source
Infinite Scroll

An Ever Changing Story

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. Recently I had been often going to the local park dressed in...

The Tax Man Comes

by Stormysailor on Jul 20, 2020
Erotic Couplings

Ced (for Cedric) approached what was probably a hobby farm or small business at the end of an unpaved, narrow road. An odd assortment of noisy dogs raised the alarm and a man came out of an outbuilding. They stared at one another for a while until Ced broke the ice, "Ross, from high school?" "Cedric, what are you doing in this part of the world?" "Obviou...

Barrack Room Betty Ch. 14

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Fourteen – Supergirls Bangkok "I've fucking had it with Jason!" Michele spat at Rod Latham "That fuckwit tracked me down and found me in a bar in Naples and created an absolute shitfight. And every night I'm here in the club he carries on like a petulant child whenever I work a punter and in particular Lieutenant Steve Winters who is one of our...

Seduced and Hoodwinked Ch. 03

by walterio on Jan 4, 2018
Transsexuals & Crossdressers

THE CLUB IS OPERATIONAL It had been five months since Darin moved in with Jasmine and her ladyboy hand maidens. The women's club took off very quickly and they now had nearly twenty women using the spa services offered at Jasmine's house. Each woman paid a $100 annual membership fee and then they paid for services when they received them. Darin was kept bus...

Jamie's Descent Pt. 04

by nikkiesilk on Sep 18, 2017
Transsexuals & Crossdressers

Fiona stood in front of me and said sharply, 'Stand, slut!' It was a tone of voice that made you think arguing about it wasn't such a good idea. I got up as quickly as I could, nearly falling over in my haste to obey. The tip of her pink tongue appeared and slid along her full lips. She had seemed tall before, but now she towered over me. I saw that someho...

Bibbit Smithers's Ordeals

by justincbenedict on Jul 11, 2018
BDSM

The Colonel's Chastity Tales June 2018 Stories BIBBS JUST CAN'T GET A BREAK Bibbit Smithers, Senior wondered why he was spending an expensive week at the Thumbscrew Lodge. Bibbs had had his ass kicked by his older brother, "Smitty" which you would think would have been bullying enough, right? And, Bibbs, no jock, had been charged with handing out towels t...

Shemale Orgy

by xploring96 on Nov 14, 2017
Transsexuals & Crossdressers

The following story includes transgender characters, Domination/submission and derogatory terms used to humiliate. If this offends you please do not read any further. Feedback on my stories is always appreciated. ***** All Ron could think about while he stared into her sultry eyes with their smoky dark eyeshadow was, how lucky I am that I am a faggot....

Seduced and Hoodwinked Ch. 05

by walterio on Jan 10, 2018
Transsexuals & Crossdressers

AN EROTIC SUNDAY On Sunday morning Darin woke up with Nin and Lawan in bed with him. They were on either side of him and he had his arms around them. As much as he would have liked to fuck them before he got out of bed, his bladder was ready to burst. He made his way to the bathroom and took his morning piss. After peeing and washing, he returned to his bed...

Inheritance Includes a Houseboy Ch. 04

by walterio on Sep 14, 2017
Novels and Novellas

AUTHOR'S NOTE: This story contains encounters involving gay sex, bi-sex and straight sex which is why it was categorized under Novels and Novellas. ***** BETSY'S WEEKEND Betsy arrived early Saturday morning as she wanted to get started early. She was accustomed to morning sex with me in the office so I wasn't surprised. When she arrived I introduced her...

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...