Sissy Prostitute Stories

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Sissy_World 03

by JDBones on Sep 16, 2017
Transsexuals & Crossdressers

Billy rode in the front seat of the car, staring out the window, and watching the world go by. His mind swam and his body already hurt, but he knew better than to protest his pain to his Husband. If he did, he would be punished with a Bare ASS Spanking and he didn't want that. He stood at 5'6 and weighed maybe one hundred pounds soaking wet, but he doubted...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

Payback's a Bitch

by sissymaidallyson on Sep 13, 2017
Transsexuals & Crossdressers

Knelt on my knees and taking a glance to my right at the sight of a woman counting cash whilst I sucked off a guy I started to wonder how this had all happened. I had a good job and didn't have a huge problem with getting lovers. I was straight and loved women but here I was – nothing but a sissy prostitute being rented out for the oral pleasure of men I di...

blackmailed into a double life

by Giratuno on Apr 22, 2025

This story is a gift to my Mistress, pray for me that she likes it https://chyoa.com/user/Cdslavejessie It was late at night when Michael, a married man with a dark secret, crept quietly into his house. His body was still filled with the excitement of the past few hours as he tried to cover his tracks and hide his second identity from his wife. Michael led...

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Afro Stress Relief Ch. 10

by llts1970 on Mar 30, 2020
Transgender & Crossdressers

I woke up on the Saturday, not believing what I'd got up to in the Beer Bust and not sure what to do, now everybody knew what I was, a little white sissy bitch that worshipped black dick! How would everyone treat me on Monday at work, Elizabeth had said not to worry as 'what happens at the Beer Bust stays at the Beer Bust', however how could I tell my black...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

Afro Stress Relief Ch. 08

by llts1970 on Nov 11, 2019
Transgender & Crossdressers

It was Monday evening, again, and I hurried home from work to get ready for my shift at 'Babes With Asstitude' (BWA). My new Afro-boyfriend, Drake, rang to chat about our new venture as soon-to-be Brothel-keepers and tell me not to work 'too hard' on my shift as a whore at Drake's uncle, Leroy's, place, BWAs! Drake wanted to come over but I said I wouldn't b...

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...

Interracial Sissy

by nancyvasquez on Sep 16, 2017
Interracial Love

Remember how I told you the story my ex wife told me - of how that white prostitute at the strip club came out of the booth after having been in there with a black guy, and how she was flushed and proud and was telling all of the other hos about how proud she was to have been with that handsome black man? Well it happened to me tonight! I almost can't believ...

Julie is a Whore Ch. 05

by Pretty_Sissy_Julie on Jul 14, 2020
Fetish

Ch. 5 I am a sissy cross dresser that has been living as a woman in Madame's brothel for about 3 years now. During that time I have perfected my skills as a cock sucker and a top notch prostitute. I have my own room in the brothel where I live and entertain clients in other parts of the House. My sister, Becca, does not live in the brothel, but whenever she...