Sissy Prostitute Stories

12,544 results
Orientation
Length
Source
Infinite Scroll

Groomed to Depravity Ch. 03

by ssamlee2000 on May 11, 2020
Transgender & Crossdressers

Mohamed sent me a link to a voice training regime for trans girls and gave me three days time to learn how to talk "properly". He said he'd call me today for my test. I skipped class again and stayed home awaiting the call. If I didn't answer or failed the test, he threatened to "make me regret it" the next time we met. All day I practiced my voice for fear...

AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

Female Erotic Police Squad Pt. 03

by mattpantyhose on Sep 14, 2017
Fetish

Most of the officers of Female Erotic Police Squad enlist in the service to catch criminals. But there are also some who do it for sex. Physical love is the modern way to fight crime, but it does not necessarily mean that sex should be considered merely a tool. As long as an officer fulfilled her duties properly there was no reason for her not to take additi...

Starlit Petal Ch. 01

by Certeis on Mar 21, 2018
Transsexuals & Crossdressers

NOTE: this story is an original setting, but anything you need to know is discussed in the story text. *** 'Swshh' 'swshh' 'swshh' Petal's legs moved back and forth rhythmically, the nylon stockings rubbing against each other at every pass. They were dangling in the air above him as he laid on the padded bench and read a book. Well, pretended to read it, a...

A Slut Awakens Ch. 02

by BrockFlair on Sep 12, 2017
Transsexuals & Crossdressers

So there I was four months, 12 days and 15 hours after finally becoming a girl. There I was, sitting in front of my new vanity and humming sweetly to myself as I did my hair and makeup. It was needless to say this was the happiest I would ever be in all of my life. I was beautiful! My long black hair was now down past my shoulders and now hung in sexy ringle...

The Blue Diamond Club Ch. 02

by MiloDeLaJolla on Sep 16, 2017
Transsexuals & Crossdressers

Subtitle: A Crossdresser's Misadventures A couple of weeks had gone by since my introduction into the Blue Diamond Club. I'd been too busy with work to pursue anything more; at least, that was my excuse. If I'd been honest, I feared how much further I'd be willing to go. I hadn't dressed in anything fem since that night. Instead, I masturbated in the dark o...

Sissy's Sexy Strut

by nancyvasquez on Aug 28, 2018
Transsexuals & Crossdressers

Last night kicked off the Labor Day Weekend, so I decided to do something daring -AND, very sexy, too! I was looking at myself in the mirror yesterday afternoon & checking out the effects of the beating I got from Mike the other night. My eye is still pretty much closed, and now it's all purpled. My upper lip is still puffed out too, but I think it looks dam...

Aunt Jo

by stories55 on Sep 14, 2020
Transgender & Crossdressers

He was getting ready to go off to college when his mother said he would be boarding with his Aunt Jo and save the money on the dorms. She said she would feel more comfortable with him under aunt Jo's watchful eye. It created a bit of disquiet in him. While he liked to have his way with women; the way his Aunt Jo had looked at him made him feel differently. I...

Groomed to Depravity Ch. 05

by ssamlee2000 on Jul 6, 2020
Transgender & Crossdressers

It was the penultimate weekend before the end of term. I had my exams in the next few days, but I didn't get to spend any time preparing this weekend. Instead, Mohamed took me to the city again. It was our fourth such trip. The itinerary didn't change much so far. We arrived Friday night. Saturday was for shopping, and once the night came, I was once again t...

Afro Stress Relief Ch. 02

by llts1970 on Apr 18, 2018
Transsexuals & Crossdressers

In the morning I was very nervous, what if my black co-workers had seen me in my outfit and also seen me doing those things with the other black studs, "Don't be worried Tina, it's unlikely they'd recognise you in the lighting of the club and your make-up. Even if they did I don't think you should be concerned, as I've said before it's not unusual for Afro-m...