Chastity Prostate Stories

15,547 results
Orientation
Length
Source
Infinite Scroll

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...

Locked Up Ch. 03: Maid Maria

by Prof_Owen910 on Apr 14, 2020
BDSM

"Ohh fuck, Gwen, yes, fuck my boicunt, stuff your fat cock up my ass!" Words I never ever would have guessed I would say spilled out of my mouth before I buried my head in my pillow and cried out, my aching balls spasming as my fiancé fucked me to yet another massive anal orgasm. A month of straight anal play with no other stimulation had turned me into a...

My Name is Raquel Ch. 10

by Raquels_Panties on Apr 13, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. As my profile indicates, I have been a passive reader of Literotica for at least 15 years. During that time, and even before then, I wrote and rewrote Raquel's stories over end over in my head. If this is your first encounter with Raquel, I encourage you to go back and start at the beginning to understand her stor...