Trans Massage Stories

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Why I Prefer Sex Work to Dating

by ShyTammy on Sep 17, 2017
Non-Erotic

First off I want to apologize for not posting anything. Emily and I are working on the next chapter of her story and I still have it on my desk to finish the "Our Secrets" series. So hopefully you'll have something new to read soon. In the mean time I wanted to get this out there. So it is the morning after Christmas when I started this and I am feeling so...

The Last Frontier - I Hope Ch. 02

by massageguy64 on Jun 24, 2019
Erotic Couplings

So if you have read my work you know that I mostly write about my experiences getting massages, mostly Happy Ending massages. These are all true stories, and I hope my writing reflects that. While a lot of these happen while I travel for business, they also happen at home in Texas. Sometimes they are basic hand job happy endings and sometimes they are full o...

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...

My Life Pt. 06

by ShyTammy on Sep 26, 2017
Transsexuals & Crossdressers

So I think I have mentioned before that I am a licensed massage therapist. I got my license because it was a good way to have flexible hours and decent pay while going to school. I also used it as an avenue for the more profitable and often times more pleasurable sex work that I do. The sex work has been mostly men. The legitimate massage business has been...

The Third Clearwater

by Damos on Jan 5, 2019
Fantasy

The Arrival It was a rainy day in Forks and looking out the window was met by Sue, my Aunt staring at me through her mirror at me, "It's Okay Damian, Charlie will take care of it all!" "I just can't believe she is gone! it was only yesterday when I was sat there watching the game with her and now she is gone!" she nodded before smiling sp...

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From a Husband to a Dutiful Sissy Ch. 15

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Fifteen: A Big Decision and Telling Mikel. Helen and I are dressed and ready to go to the ladies gym for a morning workout. I love this and dressing in my girlie workout clothes. Today I am going all black, a black leotard, black tights and black ladies shorts. I am going to contrast with my bright pink trainers. My now comfy long, just below my sho...

Hung Francine meets Hot New Friend

by mrstanley on Oct 15, 2017
Transsexuals & Crossdressers

This story is from Francine's point of view. Francine meets Octavia My name is Francine and I am a thirty five year old red headed Transsexual woman with blue eyes. My skin is very pale and I am covered in reddish freckles on my shoulders and forearms. I am 6 feet tall in my bare feet. I weigh 165 pounds, and have a well toned muscular physique. I lift wei...

The Outing of Lisa

by BmthAdmirer on Sep 16, 2017
Transsexuals & Crossdressers

Over the years as a Out bisexual guy I have always tried to keep Lisa my far more feminine side hidden away. I spent many years dressing and loved it but decided when I had to move to a new house share it was time for Lisa to go permanently. Unfortunately as many other cross dressers and transvestites know that is far easier than first thought to destroy a...

Chasing Waves Ch. 04

by dourdan on Feb 26, 2019
Transgender & Crossdressers

Ten years later; Msgt Diego Quinto's life was a barrage of bullets, deployments, violent arguments with his wife, and chemo- a seemingly endless round of chemo for his, now thirteen-year-old, son Cam. His only light was his little daughter, five-year-old Jenessa. (His wife called her Jenny, but to him, she was Jen.) Little Jen lived as an organ and tissue do...

Katherine's Choice Ch. 02

by grover10 on Sep 14, 2017
Celebrities & Fan Fiction

(Celebrity, Pornstar, Transsexual, Seduction) (Copyright) Mainstream celebrity character suggested by another Literotica member. Main characters: Katherine Heigl, Jessy Dubai * Katherine stepped out of the shower and dried herself off. She hung up the wet towel on the back of the bathroom door. Katherine opened the door and stepped out into her hotel roo...