Sissy Prostitute Stories

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Orientation
Length
Source
Infinite Scroll

The Making of Davina Ch. 02

by Timewarp10 on Nov 20, 2018
Transgender & Crossdressers

David put make up on, and looking in the mirror he liked what he saw. It was as if he saw himself for the first time; a person within being born. Davina came to life. "Oh God! It feels so right!" David remarked, seeing Davina smiling back with Davina's eyes, and not David's. He was looking through a portal into his own true soul, and he wanted to step into...

The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

Sparrows Caught and Caged

by nikisixx on Oct 6, 2020
Fetish

NOTE: This is a work of original fiction. All names, circumstances, or situations herein are purely fictional. They are not based upon either real people, governments, organizations, places, or real events. Should any parallels to real circumstances be drawn, historical or otherwise, they are purely coincidental. --------------------------------------------...

Generation Z

by contactsteph77 on Apr 3, 2019
Transgender & Crossdressers

1 - James the scavenger James was born into a new world. One of the last people ever to be born. When he was just four weeks old, a virus began to spread across the USA. It was an illness that only seemed to be contracted by females of sexual maturity. Initially the survival rate was around eighty-five to ninety percent. It didn't take long before the ai...

Contentment at Last

by Sissyelaine on Nov 26, 2017
Transsexuals & Crossdressers

At school I was hopeless in class but excelled in all sports and in art. I left school as soon as I could and much to the amusement of my friends and family, I started a hairdressing apprenticeship in Mayfair, London. I worked hard and became very much in demand but to the outside world I played all the manly sports and chatted to all the girls maintaining m...

His Sissy Whore Pt. 02

by laumadhr on Sep 16, 2017
Transsexuals & Crossdressers

Hey guys, I'm back with part two of His Sissy Randi... Thank you for soo much love on the previous story. As always, please send feedback (positive or negative) to my profile. Please read part 1 before this, or you will not have full context. ~~~~~~~~~~~~ I looked at the makeup bottles...liquid eyeliner and mascara, lipstick, and some jewelery. He came to...

The Path to Happiness Pt. 03

by brendachaplin2000 on Sep 23, 2019
Transgender & Crossdressers

I woke from a blissful slumber to the smell of coffee. I was grateful for the sofa that acted as my bed in my squat, but this bed was so comfortable I did not want to get up. As my senses returned to me, I noticed my arse was a little sore, Becky's cock cage would need more lube than a little spit if it was to go back in me. I slipped reluctantly out of the...

Our Dinner with our Hostess

by wifestoy on Sep 16, 2017
Transsexuals & Crossdressers

After a very relaxing bubble bath I shaved Renee's legs and her sweet pussy, she gave me some pampering and shaved me. This was a real treat. I got a very sweet reward by Renee. She allowed me to eat some serious pussy after the bath. As we lay down on the rose petals the soft skin and mix of fragrance from the bath oils and rose petals was intoxicating. I g...

Abducted For the Better

by BluntSlut on Sep 16, 2017
Transsexuals & Crossdressers

I woke up blind folded to hear many different voices in the room I was in. I did not know where I was and I was blindfolded. I tried to move but it felt like my body was numbed. I must have been drugged because the last thing I remembered was raving at the bar with a group bad bitches. "Where was I, Why was I here, and who are all these people" I thought in...