Prostate%20milking Stories

9,406 results
Orientation
Length
Source
Infinite Scroll

Julia Milks Her Colleague

by JohntheRapturist on Sep 12, 2017
Fetish

Tommy watched with aching adoration as the taut, luscious globes of Julia's ass swayed by in her skin-tight yoga pants. The pants were nearly translucent. The two were classmates in nursing school, and members of the same commercial gym nearby. Tommy would occasionally glance self-consciously through the glass doors where Julia participated in yoga sessions....

First Multiple Sissygasm Today

by JessC on Sep 16, 2017
Transsexuals & Crossdressers

I had my very first multiple sissygasm. I own a fucking machine. It has been the source of much pleasure since I bought it. I decided recently to try for a really great sissygasm. For those of you that don't know, a sissygasm is having an orgasm with a soft cock from ass/prostate stimulation. Well, I decided that I was going to prep myself to have a nice la...

Ward Humiliation

by innertube on Sep 14, 2017
Exhibitionist & Voyeur

These events happened when I was 24 and had just graduated from college. I was enduring a frustratingly long stay in my local hospital having been diagnosed with a mild infection and requiring to be monitored during a course of antibiotics. The main symptom I had suffered was a swollen gland at the top of my groin, and my pubic hair had been clipped away, sh...

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...

Domination by Tentacle

by SpagettiMaster on Sep 16, 2017
Sci-Fi & Fantasy

~Note: This is one of my idle fantasies while on a vacation. This content of this story is largely gay and prostate/cock sounding, so if you're not interested you can read another excellent story on this site :) Enjoy~ ***** I awake on my back feeling cold metal beneath me. It is not entirely uncomfortable, as the metal seems to curve around my body, leavi...

My Kinky Doctor

by Hrolf on Sep 19, 2017
BDSM

When the nurse finished taking my vital signs she said, "Dr. Rosen will be in in a minute," and left the room. I was perched on the examining table in one of those awful gowns that open at the back, which I always thought are specifically designed to humiliate you. I had to wait quite a while, with nothing to do except swing my legs forward and back. Finall...

Mistress Katie Supervises Ch. 01

by royalrogue on Sep 18, 2017
BDSM

Three weeks. It had been a long three weeks for Michael since his last orgasm. Since Domina had strapped him to the bed, teased and milked him to an intense orgasm. She'd eased the thick prostate massager into his tight ass and used it to heighten his arousal. Smiling as his cock throbbed and dripped, while she played with only his nipples and his ass, teasi...

The Photographer's Trap Ch. 02

by ElizzyViolet on Jun 25, 2019
Transgender & Crossdressers

Elizabeth here; lots of people wanted another one, so this is the second part of "The Photographer's Trap". Reading the first part is probably a good idea. You'll see some toys and butt stuff in this one, unlike in the previous. Happy reading! ~~~~~ ~~~~~ Since that Saturday morning, Timothy started to find himself wearing panties underneath his ordinary c...

Sexy Doctor Gives Prostate Exam

by SluttyBisexualGuy on Nov 25, 2017
BDSM

Ethan walked into his doctor's office to check in for his 2:00 PM appointment. He was nervous. He'd never actually had a prostate exam before. His girlfriend Jenna had suggested that he go and see a doctor on his 25th birthday and get a full physical to make sure that all of his parts were in working, sustainable order. He knew he was a bit young to start...

Never Say Never Pt. 03

by SunChris on Sep 12, 2017
Anal

Well, as you can see, Rachel made the transition. Lucky me. Sex with Rachel has always been great, but anal sex has added an entirely new level of enjoyment. According to Rachel, her orgasms while having anal sex are off the charts. We still very much enjoy regular vaginal intercourse, but we definitely like to delve into anal play. It is more work, so to s...