First Prostate Milking Story Stories

329,355 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Crossdresser's First Anal Orgasm

by ksha on Sep 16, 2017
Anal

A young man still experimenting with his body, found a new fetish he enjoyed quite a lot. He found the joys of anal masturbation. He had heard rumours of an orgasm so wonderful it would leave you shaking afterwards. He was in search of his very first prostate orgasm. This is the story of the first time this young man would discover the joys of prostate pleas...

Mrs. Swanson's Boarding House Ch. 06

by 0ra11yfix8ed on Sep 25, 2017
BDSM

It has been quite some time since chapter 5 was submitted so if you are not already familiar with the story line it might be advisable to start with Chapter 1. Fems up, ladies! * It was getting late in the afternoon and Mrs.Swanson was at her best as she combined two of her favorite activities; masturbating young men and displaying her considerable power...

Nocturnal Anal Stimulation. A Study

by suppleWriter on Sep 17, 2017
Fetish

Note: this is a story, fiction. None of the facts are correct, and all the names are false, invented. So enjoy! (Re-posted with the above clarification, and links deleted). Nocturnal Anal Stimulation in Orgasm-Denial Relationships - A Study NOCTURNAL ANAL STIMULATION IN ORGASM-DENIAL RELATIONSHIPS. A STUDY BY: Willsoin,D.E., Arangji,T.F - UCNYCE - Dept...

Mother Mistress Ch. 07

by JamesLacy on Sep 12, 2017
BDSM

This story is the property of the author. It is not to be changed in any way, nor published or shown at other web sites without the permission of the author. Feedback and comments to; James Lacy at the address in his profile. All comments appreciated. Earlier, Mother Mistress had called Cindy to tell her that she and Jane decided to spend another two week...

Chastity with Steve Pt. 03

by drdick69 on Aug 21, 2018
BDSM

It's been about two months since Steve asked me to lock up his cock. It didn't take long before I realized that I really enjoyed the power exchange. I now had him doing everything I asked, without complaint. The house never looked better. My pussy had not seen his cock for the same period. Although I love and enjoy normal sex, I love being served even more....

How I Became a Chastized Cuckold Ch. 04

by gizzard on Sep 19, 2017
Loving Wives

**Warning** This fantasy story series contains or will contain elements of Male Chastity, Orgasm Denial, Female Domination, Cuckolding, Interracial Sex, Bi-sexual Innuendo and Tendencies, Teasing, and BDSM Activities. If any of these topics are offensive you to, I recommend not reading. * It was a few days before she allowed me to use the rubber black cock...

Waiting Leads to Fantasy

by lovingspouse on Sep 17, 2017
BDSM

My first submitted story... ______________________________ You were out with the girls for Happy Hour and i find a note which reads "My loyal knight, Shower, shave, and be kneeling when I return. Dress like the slut you are. I want your ass, nipples, and cock stimulated. Don't disappoint Me. your, Queen" So, Black crotch-less tights Black slip, held up...

When Sara Met Bob Ch. 02

by yellowfrog on Sep 14, 2017
Fetish

PART II: Bob learns to sip Sara's pee and Sara explores his prostate. * Our first night together was one of unblemished bliss. Spooning Bob all night, I felt his breathing and his heartbeat. With the first rays of morning I knew we both had to rise and shine for the day ahead of us. Neither wanted to get up, especially not me. On the other hand, my bladder...

Cowper's Gland (The Ultimate Lube)

by jasliz on Sep 15, 2017
BDSM

My wife is very kinky; I'll say that right now. She likes dominating me and teasing my body until I scream for release. She says it's for research... her own. Since she calls it research she institutes 'controls', basically the controls are me tied up so I can't touch her or myself. She made me set up a table in the basement with padded straps for my wrists...

Physiotherapy

by GforGraham on Jun 1, 2020
Mature

Warning: I'm told I use too many words, so don't expect a short jerkoff story, just a short story by my normal standards. I tried being brief and lost the plot, so will stick to my own style and letting the story tell itself and be as brief or as long as it needs to be. You have been warned. Chapter 1 "Mr Waterman, from all the information here I'm sorr...