Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

She Creates the Fantasy

by TheKingofNod on Sep 18, 2017
BDSM

I. She Catches Me Needless to say, I was very embarrassed when my wife caught me at the computer—shorts down, Kleenex in hand to catch the incriminating evidence, dick hard and out in the open, and a woman on the screen forcefully making her man cum. She said my name. "What the hell are you doing?" I tried shutting the computer screen, but she put her han...

Cindy's Birthday Surprise

by thomstevens on Jan 1, 2019
Anal

Cindy promised that she had something special planned for my 30th birthday. I wasn't sure whether to be pleased or frightened. And yet, there I was, naked, my wrists shackled to either bed post like Christ on the cross, my ankles shackled and bound up with straps against my thighs, making my nether region fully exposed and accessible. And then she put on t...

My First Customer Ch. 02 Pt. 02

by Darkwatch on Jun 4, 2019
BDSM

The warm sun felt wonderful, caressing my skin as I was hanging in my daze. The gentle breeze cooling the sweat from my tortured skin. Mistress Wendy had left me hanging from a tall tree in her back yard after whipping my ass soundly, and I wasn't sure just how long I had been left outside. My hands were pinioned behind my back and tied off to the collar aro...

Life and Time of Lady Vargos Ch. 19

by rik581 on May 21, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Martin stared out the car window as he was driven to meet Darren once again. He was in the back seat of a different car than the first trip and it was no limo by any means. Martin's thoughts were swirling around things he was beginning to notice. He was being allowed out w...

The Land of Dreams Ch. 08

by giandomenico on May 22, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** (A Tale of Old Leonesse) The Soldier's Reward This is one of my favourite tales of Old Leonesse, long before my time here. It is a tale of women of my kind becoming wives and mothers. It is told by a lady called Maia. Moonflower. I watched from my balcony, veiled, as my husband...

Neighbors Delight Ch. 03

by gummidurango60 on Jan 7, 2019
Transgender & Crossdressers

Day 2: The Morning After "Mmm," I stretched before opening my eyes. It took me a few seconds to realize where I was and what I was doing here. I remember Aaron caught me in fem yesterday when he brought over a UPS package that was delivered to his house instead of ours; then he blackmailed me into cleaning his house. Anyway, it led to my first fuck and an...

To Serve Her Ch. 02

by njcaptionlover on Feb 26, 2019
Transgender & Crossdressers

After staring at the pink collar, I looked into Tammy's eyes hazel eyes and nodded. "I need to hear you say it, sweetie." Her voice was soft and gentle yet there was a commanding tone to it that made me feel meek. "Tammy. I would like to serve you as your live-in slave." I am not the type of person who makes hasty decisions but there is something about T...

Now a Slave Ch. 08

by NScioli on Dec 11, 2018
BDSM

At this point, things are getting more severe. Chase is more active, and if people like him I will post his series here. If not, he's there as an oddity. The vampires are mentioned in this chapter saying that Chase's slaves are fed from only in an emergency of vampires being low on meals. I repeat, I do not see the vampires will ever show up, they are there...

The Ogress's New Pet Pt. 02

by Myrph on Jan 15, 2019
NonHuman

Author's Note: I don't care for sequels, but I just felt the urge to continue this one. I hope you enjoy! Story Tags: Futa on Male, Ogress, Monstergirl, cumflation, threesome, Mandragora, Nonhuman ***** Nathaniel held his lover's hand and wrapped his other arm around her beefy neck. His breathing slowed as he regained his composure. The Ogress slid one ha...

The Corner Office Ch. 03

by Sgt_Hook on Dec 12, 2018
Erotic Couplings

Time passed, and so did the passion that William and Olivia shared. Abruptly, Olivia became distant, basically ignoring William. She stopped calling him, returning his calls, and always had an excuse why they couldn't make love. After several months, William confronted Olivia to have her explain what was going on in their relationship. To his dismay, she avo...