Sissy Prostitute Stories

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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...

From Business Owner to Prostitute

by Kellycumslut on Dec 2, 2019
Transgender & Crossdressers

How things have changed. From respected business owner to insatiable street prostitute. For a long time I ran a very successful business in London employing 14 staff and loving my work. I worked six days a week and on Sunday I did the paperwork, wages and stock checks. I had no time for social life, I was working for a successful future and in the evenings...

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...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Summer Plans

by Weebwithkinks on Feb 21, 2020
Transsexual

Finally summer is here you've been waiting for this for a long time after a gruelling 1st year of university, you can relax for the next 5 months without any deadlines or assignments. You're heading back home for the summer to spend it with your family, nothing special but a much needed change of pace. Last time you spoke to your parents they said nothing mu...

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A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

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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...

Julie is a Whore Ch. 04

by Pretty_Sissy_Julie on Jul 14, 2020
Transgender & Crossdressers

I had just finished sucking Morris' black cock when he showed me that Madame and my sister were watching the entire encounter. I was naked and soaked with his morning piss as well as have my face covered in my cum and spittle. He playfully slapped my arse and told me I should go talk to Madame. As I walked I felt every step as his piss squished in my stocki...

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...

Marcia Goes Back to School

by Belongs2Beth on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: This story continues the adventures of eighteen year old Marcia (nee Marcus) Cicero. The tale opens a week after the events related in "Carol's Gifts". Marcia has shown visible signs of blossoming in the wake of Mistress Carol's injection of powerful hormones and is anticipating returning to her school for the first time as a girl. To answer an...