Sissy Prostitute Stories

12,544 results
Orientation
Length
Source
Infinite Scroll

Growing Pains

by Spoox on Feb 8, 2020
Romance

Tip: This is a slow burner loosely based on my experiences. If you want something to wank off to, skip to the chapter First Date and the options that lead off from there. Don woke to the electronic buzz from his alarm. He rolled onto his side and reached for the snooze button. On pressing it, he heard the familiar pitter-patter of feet on the stairs. "G...

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Cream Puff Ch. 01

by RubixStu on Mar 12, 2019
Transgender & Crossdressers

Never borrow money you can't pay back right away. When I got in trouble with the IRS, I borrowed money from my wife's brother Larry, and I struggled to pay it back. We were drinking at his house a few weeks before his wedding when he brought it up. Larry: Hey cream puff, I know you don't have the cash to pay me back right now, how about doing a job for m...

Letter From Tacoma

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: When my husband, who is owner and ringmaster of the Epic Circus, comes into our hotel room (We, thankfully, don't have to live in the circus trailers) I'm ready for him. He lays the whip down, and then it's my turn... "Strip it all off Apollo, my love! Now you'll get a nice thrashing....it's MY turn to use the whip!" Sometimes after th...

Black Man's White Sissy

by nancyvasquez on Sep 18, 2017
Transsexuals & Crossdressers

I started jerking off to ejaculation when I was around 18. Once I started doing it, it was all I thought about, 27/7 it seemed like. I collected fuck mags and porno tapes wherever I could find them, to use as visual aids. Just looking at those sexy nude women being loved up by their hot men made my dick so fuckin' HARD! Because of that I was able to convince...

The Making of a Mistress Pt. 05

by EiryCGar on Sep 14, 2020
BDSM

Author's note: Marie has married and taken possession of Charles, now known by his initials as Cunt. She has become an official Hotwife; Cunt is now a true cuckold. This chapter deals with their honeymoon on Felicity's island, and the momentous decision that is taken when she and Cunt return home. As always in my fictional stories, all sexual acts take plac...

Trapped! Pt. 01

by TheEroticProspero on Jul 6, 2020
Transgender & Crossdressers

Trapped Part 1: A Trap Is Sprung As a teacher, I shouldn't admit this. But sometimes you have students you just hate. And for almost a year I had hated Jessica Dane. I was only 25, fresh out of university, straight into a job teaching English. For all my life I was poor, short, thin, and pale. My only saving grace appearance wise was my long, rocker...

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...

The Virgin Tranny & the Bride Ch. 09

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Dear Friends, A MESSAGE FIRST. I am submitting a further chapter in the series The Virgin Tranny and the Bride. However I am concerned that I may be doing something wrong at this stage which is preventing these articles from registering in the Top 500 chart despite a number of votes and a high rating. Perhaps it is me, or perhaps there is a technical probl...

Vacation Expectation

by IPleaseYouTease on Oct 6, 2020
Fetish

The wife's side of a conversation with her husband as she gets packed to go on a 10-day vacation with her lover and leave him behind. ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ ~~~~~~~~~~~~~~~ "Okay Dearie. Up on the bed. It's almost time for me to leave. I have a plane to catch. Don't you worry. I know that once you're done binding your hands and fee...

Sam Meets Ms. D

by jadedappetite on Sep 26, 2017
Transsexuals & Crossdressers

Sam was a very bright, 18 year old man. He was slighter than some of his peers, having never worked out his muscles. Sam was somewhat of an outsider, not sharing in all of the same interests as the youth around him growing up. He had few friends. Being a junior in college, he had his own apartment under the new free housing act. He was non-religious and this...