Ladyboy Massage Stories

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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...

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...

A Ladyboy for Master Hans

by justincbenedict on Sep 16, 2017
Fetish

After Chip had cooked dinner and waited on Hans, and had his own meal in the kitchen, cleaning up quickly, he got busy polishing Hans's shoes and boots. But in the middle of polishing Master Hans's last set of boots, Hans interrupted Chip. "Chip. How many times I must tell you? You have not written down your Stuhlgang, your poo-poo!." Hans, who was a st...

Exotic Escapades Ch. 03

by exroticdistant on Sep 14, 2017
Transsexuals & Crossdressers

The smell of wood and coffee filled the quiet house as Tammy slowly picked herself up from a plush couch. Daggers of sunlight blinded her eyes as she eventually got on her two feet. Her body ached, and she noticed a small pink bandage on her left leg. The terror and pain of last night shook her as she slowly tried to find the kitchen. In the distance, she sa...

The Reunion Ch. 03: The Hot Tub

by Valtikka on Jul 14, 2020
Exhibitionist & Voyeur

*All characters in this story are at least eighteen years old* I only realize how much I missed these people after seeing them again. Jessie is the first to arrive. He's still driving the old Volvo my father gave him when he passed his driving test as a student. He brought his daughter Zoë with him and judging by the look on her face she would have rather b...

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...

Cockatoo Pt. 18

by nikkiesilk on Sep 16, 2017
Transsexuals & Crossdressers

We finished dinner in the restaurant, then walked upstairs to the flat and sat out on the terrace, drinking and talking about what our next steps should be in the plan to launch the new club. We threw around ideas for possible names, some better than others, and we provisionally settled on Cockatoo Cabaret as a tie in with the bar. I also mentioned that whe...

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...

Patricia

by Victor Field on Sep 12, 2017
Transsexuals & Crossdressers

This is inspired by, and sort of about, the incredibly beautiful Brazilian transsexual porn actress Patricia Araujo - Machado is her real last name (though in this story she doesn't do porn these days a la Elisha Cuthbert in the underrated "The Girl Next Door," the only actual similarity - no proms or award robberies here!). Apart from her, none of the chara...