Sissy Prostitute Stories

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Billy's Sissy Adventures.

by Trom1806 on Aug 21, 2023
Interracial

Billy's Sissy Adventures. Adventures of a young white sissy guy in sunny California and maybe somewhere else... Synopsis You are Billy Atkins, a white male student at Hayne College in Hautenville, California. Chapter 1: Introduction You are Billy Atkins, a white male student at Hayne College in Hautenville, California.......

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...

Life as a Gooner

by Yelawolf on Feb 18, 2024
Bisexual

Life as a Gooner A guy life as a porn obsessed loser Synopsis You are a Gooner. A person who loves to masterbates to porn nonstop. Will you fall deeper into your addiction or finally lose your virginity Chapter 1: Introduction "Come on {mc}. Me and Trey are going to shoot some hopes down at the YMCA. You need to stop d......

Three Old Tarts and a Sissy

by Sissy Adele Howells on Oct 13, 2017
Fetish

At 50 years old, I have started to have kinky thoughts about older women. This fantasy that I am about to narrate to you concerns three neighbours of mine. Between them their ages total 200 years. They have found out that I'm a kinky sissy, but this seems to make them crave for more sexual activity. The eldest of the three Joan Harries, encourages the other...

Julie is a Whore Ch. 06

by Pretty_Sissy_Julie on Jul 14, 2020
Fetish

Ch 6 Hello, my name is julie and I am a sissy CD. I am very passable and by the time of the events in this story took place and I had a nice bra size of 34B. This is a difficult story for me to write because I am going to write it in 3 parts. The first 2 parts will seem to be unrelated, but hopefully the third part will tie it all together. Just as a warnin...

Julie is a Whore Ch. 10

by Pretty_Sissy_Julie on Sep 14, 2020
BDSM

This is a story about BDSM and pleasure. Please understand everything done was consensual The scenes are no worse than you might see in the movies. There is no actual "snuffing." All of the women involved savored the experienced and had intense orgasms. This story is for your entertainment only. My name is julie, I have been living as a sissy whore for year...

Sissy Plays the Game of Thrones

by SissyKelly on Dec 1, 2017
Celebrities & Fan Fiction

Kelly Waters, fucking Waters I thought to myself as I shook my head. I think the worst part of being a bastard is knowing you could choose any last name, but having it dictated still by birth. I knew not who my parents were, in fact I only knew I was Kelly Waters thanks to the man who raised me, Lord Petyr Baelish. I was born in his house, his whore house,...

Sissy Plays the Game of Thrones Pt. 03

by SissyKelly on Dec 13, 2017
Celebrities & Fan Fiction

I felt the shocked and angry eyes of Jamie Lannister staring at me. My twitching butthole. My balls. The base of my cock, the rest of it buried in his sisters pussy. His lovers pussy. "What the- what are you?" Jamie asked, I couldn't speak. I pulled out of Cersei's pussy and fell next to her on the bed, she sat up and smiled at Jamie. "Oh little brother,...

A Sissy Saga Ch. 09

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam Hancock arose in the morning alone but feeling joyous and revitalised. But when her early toilet had been done her smile faded, and she frowned. On the dressing table lay the fat envelope she'd received that morning from the lawyers employed by Lady Diana. It enclosed a letter that was dreadfully succinct. '... Our client as brought to our attention...