Sissy Prostate Stories

15,115 results
Orientation
Length
Source
Infinite Scroll

Memories

by StarsAligned on May 7, 2019
Erotic Couplings

Sarah stirred as she awoke; groggy from the slight wine hang over from their dinner the evening before. It wasn't a true hangover, but she had been happily buzzed from the rose moscato and love she felt from Henry. This was her idea of perfection in life. She didn't want to open her eyes as they laid there together, his arms wrapped around her naked torso,...

The Old Artist Ch. 03

by MagicBob on May 6, 2019
Mature

All characters over eighteen. Thanks to S for helping me edit this story. *** Later that afternoon, Gary got a call from Kate. "Hey Kate, how are you?" He wondered how she was fairing after her first mega-orgasm. "You sweet man, just what the fuck did you do to my brain? It keeps sending quakes to my vagina, and the kids in the class are wondering what is...

Love on the Edge Pt. 02

by giandomenico on Jun 26, 2019
Transgender & Crossdressers

A year had passed. Alec looked up hard at the quarry wall then down to his canvas. Something wasn't quite right 'And,' he thought, 'anything which isn't quite right in painting makes the whole thing wrong.' Usually he could see straight away what needed to be changed. Today he couldn't. It was as though the essential wrongness lay not in any detail or ma...

A Different Kind of Teacher Ch. 03

by First_time_bi on Apr 20, 2020
Transgender & Crossdressers

I woke sometime later. It was dark. I could feel Lisa breathing beside me. I gently rolled over. Lisa had slipped over onto her back. There was a soft light coming in from the window. I watched as her chest rose and fell with each breath. Her breasts fell slightly to each side, but the nipples were still prominent, still hard. Her body tapered from her full...

Revelations of Amanda Ch. 01

by Alkino on Sep 28, 2020
Exhibitionist & Voyeur

It was half past two in the morning. Since it was a Tuesday, most of the city was asleep, as always, with the usual exceptions - hotels and gas stations, night shift workers, insomniacs and lonely souls of all kinds. Gusts of wind brought promise of rain after several intolerably hot days, blowing scraps of discarded newspapers down the sleepy alley beneath...

Bill Meets Jessica Ch. 02

by lateknew on Dec 3, 2019
Fetish

Following chapter 1. Jessica and Bill (Alexa) meet again - Friday. Jessica wants another meeting. ***** I received a message from Jess asking if I wanted to meet her for coffee up town, a week had gone by since our initial meeting. That was a pleasant surprise for me. I texted "Ok, we meet in half an hour," knowing where we are to meet, soon after I recei...

A BBW Experience

by BigDonGStone on Nov 12, 2019
Erotic Couplings

To my readers: Dedicated to my friend Christy, who graciously allowed me to use her name in this story. Too many people look at BBW's as a fetish or an aberration. In fact, as a BBW lover, I can state without reservation that a BBW is no different than any other woman. It is unfortunate that a tag or label is attached to describe physical attributes. The...

Take Me

by CuriousCouple24 on Dec 24, 2019
Anal

Pat woke to the incessant throbbing of his cock. His hand slid down his stomach and found the head of his shaft drenched in pre-cum. Pat pressed the tip into the center of his palm and slowly twisted, lubricating his full length with his emissions. Pat stroked his cock slowly. He grasped his cock so that his thumb and forefinger made a ring around the base...

The Training of Jeff Stintum Ch. 27

by JoyceJulep on Jul 13, 2020
Fetish

Chapter 27: The Red Light Jeff wondered how it was that he could be so continuously amazed by Sarah's body, even though he had seen her, and felt her, up close so many times. But as he heard Sarah hum deeply down at him as she pulled out of his parent's driveway and drove down the road, he couldn't help his eyes drifting downward to gawk at her body. It was...

The Theater

by WhiskeyIsGood on May 11, 2020
Transgender & Crossdressers

This is based off my actual first encounter with a transsexual, and also my first trip to an adult theater back in March, just before the lockdown started. It certainly didn't go the way that I expected, but I still had a good time that day. I figured I would share my experience with my fans, although this is a slightly exaggerated version of what actually h...