Gay Prostate Stories

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Infinite Scroll

Back Fence Glory Hole

by Whispor on Sep 14, 2017
Erotic Couplings

I met Dorothy at a community meeting to discuss zoning proposals in our neighborhood. I recognized her as the elderly neighbor who lived behind us, but we had never been formally introduced or spoken to each other. We made small talk about the issues being discussed, how nice the neighborhood was, and so on. I'm 41. Dorothy was older. Much older. She menti...

Dual Use Building Retail Strip

by Alluring_Crimson_Shifter on Dec 24, 2019
Anal

Nancy was recently separated. She had to start a new life and was busy getting an affordable place to stay, and a new job. She stood in front of the mirror getting ready for work. She was a hair stylist, and she loved her silky brunette hair. She looked at the frontal view of her panties and loved how good her pussy looked. "Hello good looking," she said to...

Queen of Paradise Ch. 02

by ptpl_guy on Sep 16, 2017
Transsexuals & Crossdressers

This is a work of fiction. Names, characters, businesses, places, events, and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. ***** Earlier, Mark and Maria stayed at the pool as Mike headed up for his transformation. The...

A Whole New 'Woman'

by cds6 on Sep 16, 2017
Transsexuals & Crossdressers

I was out of town on a business trip. Work ran late at the client's office and I was a little tired, but really wanted a drink. Not knowing the area, I just drove around until I found a decent-looking bar. As I made my way in, I only noticed that the lights were dim and the bar was set up like a relaxed club. The theme was very post-modern and there was ele...

Turned into a Slut Ch. 01

by xaitonnar22 on Sep 19, 2017
BDSM

This is a repost/reedit of my story. The beginning hasn't really changed but I did add a fifth ending chapter. * My girlfriend and I have always been a little kinky. We liked to tie each other up every now and then. We both enjoyed it every time we did it. I didn't realize that it was only the start of something that would land me in the position I am in...

Secrets

by Dawns on Sep 16, 2017
Transsexuals & Crossdressers

I was wearing panties that day under my black denim jeans, a habit that went back a few weeks to the Halloween party given by my sister at her home. My Brooke Shields impersonation that night, a very good one, led to jokes that I could date a guy. Cross dressing in any form is not something that I talk about. It's just something I do. It would embarrass me...

Rented Out Ch. 02

by voluptuary_manque on Sep 16, 2017
BDSM

My thanks to those who enjoyed the first chapter in this story and especially to those who commented on it. I live for comments. * Mark stood at the back door of the mayor's official mansion. He gulped and started to unbutton his shirt. While guests, officials on business or even the general public might enter through the front door, those who came to the...

Becoming Her Bitch

by HerLittlePiggy on Sep 13, 2017
BDSM

"Take it like a man you sissy bitch," Jennifer said as she thrust her big strap on into my ass. "Yes mistress," I groaned as the long life like dick pounded my prostate. "I'm not your fucking mistress you sissy pig," my wife yelled as she slapped my ass hard leaving it stinging and red. "A mistress wouldn't have her cock inside your sissy ass. From now on...

Lois Lane's Night Out

by exxxidor456 on Aug 13, 2017
Fan Fiction

As with all my stories, I welcome other authors to add chapters! Remember to like and bookmark your favorite chapters! Regular chapters with 5+ likes get a sequel, chapters with 10+ likes get two. End chapters get an epilogue with 10+ likes. Chapters with the most likes & bookmarks get updated first! All characters in this story are at least 18 years old...

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Jack and Jill Pt. 02: Jean

by candyflosslover on Jul 13, 2020
Transgender & Crossdressers

It was two weeks later when Jean returned, it had been arranged that she would get there a couple of hours before Jill came home, to prepare him. He wasn't sure what to expect and he felt a mixture of excitement and anticipation. He followed her into the bathroom where she stripped him naked and shaved his entire body. He loved the smooth feel of his skin, e...