Chastity Prostate Stories

15,547 results
Orientation
Length
Source
Infinite Scroll

Helen's Slave Ch. 02

by VivianeGreen on Sep 15, 2017
BDSM

*This story is dedicated to non-monogamous lovers everywhere. And more importantly, the couple who inspired this tale. I can only dream...* Alex walked up to the stern looking man at the front door of the leather club he and his wife frequented, and said, "I was told to go to room 107." He was already wearing the collar his wife had first collared him wit...

First Time

by eroticbisexual on Sep 15, 2017
First Time

My wife and I have been married for a long time. We are deeply in love, and have a great sex life. I have always been kinkier than her, but over the years she has explored with me and over time become a sexy minx who secretly loves our kinky play. She is very beautiful, slim, erotic and with a body that make me proud to be her husband. I have always had bi...

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...

Chastity Resort Pt. 07

by handyrandy9 on Sep 25, 2017
Fetish

This is a continuation of a multi-part story. If you don't start with part #1, none of this will make sense. ***** After the sex shop on the boardwalk (where I ate out Anna in the changing room to an impromptu orgasm) the rest of the afternoon was relatively uneventful. The four of us shopped for a while longer, then we all sat on the beach sipping drink...

Remaking a Boyfriend Pt. 02: Important Lessons

by her_every_command on Nov 12, 2019
BDSM

Ray awoke to the unfamiliar sight of the soft glow of predawn light from the window and a throbbing pain in his cock and balls. He instinctively grabbed them, only to be surprised by the feeling of warm metal. The surprise morphed into anger as he remembered the events of yesterday. The sharp ache at the base of his swollen penis showed no signs of abating....

Mistress Katie Supervises Ch. 04

by royalrogue on Sep 18, 2017
BDSM

Michael was sweeping the garage when Mistress Katie's car pulled into the driveway. Puzzled, he watched as she got out of car. She was dressed in a white knee length sundress with plenty of luscious cleavage exposed and a high-heeled pair of sandals. Smiling, she walked into the garage and approached her submissive. "Surprise," she said, "I know you weren't...

Suzy and the Trucker Pt. 02

by HappilyLockedMan on Jun 18, 2018
Group Sex

Dear Reader, the characters in this story were introduced in "Suzy and the Trucker." You may enjoy this story more if you read that one first. ***** It started with the tiniest little tickle of an idea but grew into an obsession. Vera's imagination was in high gear as she scrolled the internet searching "sex toys". She thought she knew what she wanted bu...

Teased, Denied and Sissified Ch. 04

by subbieman on Sep 12, 2017
Fetish

Quick Recap It had been nearly two weeks since Ashley caught me trying on her panties and I was now wearing a fresh new pair every day along with a bra as she encouraged me to find my "inner-sissy" and explore my fetish. I had also learned that she obtained more pleasure from her toys than my cock and, as part of this "exploration," she had decided it was b...

A Freshman's Summer Class Ch. 03

by CapnSteelBoy on May 11, 2020
Transgender & Crossdressers

Edited by HotandHollow **All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventure continues during his summer of higher education learning! This is a continuing series I'll be releasing as my helpful editor(s) help me clean up my mess.. Much thanks goes out to them, as the editor(s) tha...

Dynamic Servitude Pt. 03

by Cagersslave on Apr 28, 2020
BDSM

Dynamic servitude: A Master to a Daddy A slave to a son Part three. The Master leads Cager's slave from the lounge to the bedroom, Cager's slave shuffling along on the floor on his hands and knees, his eyes transfixed on the tall boots. he sees the boots pass the threshold of another room and He stops, turns and sits on the bed. 'Look up slave.' S...