Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

On Her Terms Ch. 03: The Descent

by econut on Sep 18, 2017
Fetish

To say Dale was confused by his new lifestyle arrangement would be an understatement. Over the past few weeks, his entire life had been turned upside down in a series of events that had escalated faster than he could even adjust to. And that was exactly the way Sam wanted it. Sam was Dale's ex-girlfriend's lesbian lover. And now Dale's Mistress. Or should i...

Neighbors Sissy Son Ch. 06

by newfield1981 on May 2, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Tiffany Charles My name is Charles Bennings but you can call me Tiffany Charles. If you've been following this story from the beginning, then you know I was born a boy but with my feminine body and face, I easily live my life as a girl. You also know that I make a lot of money do...

Recruiting of a Sissy Maid Ch. 08

by Sissy_Chantel on Oct 15, 2017
Transsexuals & Crossdressers

Chapter Eight: Chantel Moves Up at The Jade Maid Club. Six months now into Chantel's new life as a t-girl maid and slut at The Jade Maid Club has her progressing well. Hormones have aided in her feminization and she has proven to be a very good and docile enslaved sissy girl. Not perfect but impressive to see that Mr. Luftgrin, Mr. Jenkins in reviewing all...

Sissification 101: Ch. 03

by silkstockingslover on Jun 8, 2020
Transgender & Crossdressers

Sissification 101 Ch 03 Summary: Eric(a) gets pegged for the first time. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by a very supporti...

Six Months

by JamesMiehoff on Dec 10, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

The Audition

by bitomah33 on May 7, 2019
BDSM

His heart was beating so hard inside of his chest that he could no longer think clearly. He just realized they really did not plan out this scene ahead of time. He was so drawn to her energy that most of his rules regarding safety were ignored. For some strange reason he trusted this stranger, as if they were intimately involved in a former life. He was begi...

High School Dilemma Ch. 06

by LaurenWestley on Sep 15, 2017
Fetish

(Authoress's note: of course all disclaimers are still in place regarding characters etc. PLEASE DON'T READ THIS IS YOU HAVE AN AVERSION TO PEE SCENES AND EXTREME HUMILIATION. This is only a fantasy story XXX+. I only wish there is enough here to make each of you happy. To those who have given me constructive criticisms as well as those with praise thanks. I...

Eve Quest Pt. 03

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Sometime during the night I was released. That exquisite pain at the point my limbs were release must have dulled my recollection of the events. I'm reasonably sure I was given the Toilet command and I hope I did a good job. In any event, I was still on the bathroom floor when I heard my mistresses stirring around the next morning. I got up, crawled under th...

Groomed to Depravity Ch. 06

by ssamlee2000 on Sep 14, 2020
Transgender & Crossdressers

It was Mohamed's birthday today. In exchange for having "skipped on the job" on Saturday, I was to be the "entertainment" tonight for the party. I had my term exams this week, but I wasn't exactly in a position to say no. I'd already fallen so behind on the materials due to my weekend duties, I doubt one more night of studying would've helped me anyways. I...

Camboy's New Mistress

by pluggedforlife on Jun 5, 2018
Transsexuals & Crossdressers

His heart was pounding with passion. The big black dildo slid in and out of his well-lubed butthole, tickling his prostate. He could feel the large black penis glans squeeze out a drop of precum as he exhaled a moan of lust that was building up in his lungs. His steel chastity cage was flopping up and down, hitting his smoothly shaven crotch. His silver ho...