Milking Prostate Stories Stories

84,016 results
Orientation
Length
Source
Infinite Scroll

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...

Dressed for Disaster: The Prequel

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

Dressed for Disaster: The Prequel Pat Summers put his suitcases on the bed, and made a quick survey of his room. He noted with approval the full-length mirror on the back of the closet door, and he poked his head into the bathroom to inspect the bathtub and vanity. Not overly luxurious, but they would do. First things first. He opened his computer case and...

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...

Milking Cocks

by Anal Slave on Sep 12, 2017
Fetish

My wife of ten years loves kinky sex. She will try anything once and if she doesn't like it she will still try it again. My body is under her complete control; she uses me any way she wants. Her new thing is milking cocks of course I can only produce so much cum. So we go to the local bar and she picks out some guys. She wants to have sex with. She is a lit...

Scenes from a Marriage Pt. 03

by DopamineFan on Mar 3, 2020
BDSM

My wife and I had just recently discovered that we both love it when she dominates me. In the last couple of weeks, we'd had our first two real scenes, which we both loved. We'd been talking a lot about what we were each interested in exploring, and she had been spending a lot of time online reading and learning about D/s. We had also continued to buy variou...

Fellatio

by kinkyraerae on Sep 13, 2017
Fetish

DISCLAIMER:// My boyfriend and I started writing these stories for each other a while ago. He challenged me in the beginning to write the most kinky story I could think of. You'll see what came of it. He's also posting his stories on his account. I'll update this with what it is soon enough. No, none of these events have actually happened. They are pure fan...

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...

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...

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...

Mistress Katie Supervises Ch. 03

by royalrogue on Sep 18, 2017
Fetish

Michael was mowing the lawn when she called. Slowly he had been crossing the small lawn, pushing the mower at comfortable pace chosen to avoid sweating too much in the warm summer afternoon heat. The quiet mower whirred, clipping the few grass blades that had grown tall enough to reach its rotating blades. Luckily, the mower did not prevent him from hearing...