Prostate Milking Stories

30,157 results
Orientation
Length
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Infinite Scroll

Mother Dear Pt. 09

by keptsissy on Sep 13, 2017
Fetish

"I love this place, baby boy. Every time we dine here I think back to that one fateful dinner, the dinner where this all began. The dinner after I came to your home unannounced innocently enough, wanting to take you out to eat only to find you dressed like a girl and on your knees doing what we bad girls do, delightful." She winks at me over her wine glas...

Subway Romp

by dravendevere on Sep 16, 2017
Fetish

As I looked over my shoulder I saw her standing there in line for the washroom. She always looked so damn cute when she had to pee. Her face always got a look of urgency, one that made it look as if she was going to burst at any moment. That really turned me on, imagining that she could explode into a torrent of golden honey liquid. I had never told her bef...

My Slut's Needs Ch. 02

by Penisleeve2020 on Apr 20, 2020
Fetish

L returned to her teasing, blowing on my balls, licking the head of my cock, sliding down to kiss my hole and getting me more and more excited. I tried to catch her head and really wanted to face-fuck her deep and hard or roll on top of her and skull-fuck her mercilessly but she wasn't having any of that just yet. She'd got me fully hard again when she sudde...

Roger's Visit to the Clinic

by glovesnap20 on Jul 4, 2018
Fetish

I found the clinic answering an ad in the local paper. Only working part time, I'm always scanning the back pages for odd jobs. "Subjects needed for medical test. Must be male, under 30. Call to apply. Free physical." Why not? With no health insurance, it was win-win. I called, and the receptionist, after confirming that I would qualify, was vague about wh...

The Versatile Student Ch. 02

by atlanticsexual on Sep 16, 2017
Fetish

Dave awoke with a start. Something seemed somehow different. His hand was drawn to his penis and there he felt it. ... At breakfast, Denise smiled at him. I'm really pleased with you Dave. You look so nice in your undershirt and boxer briefs, eating your breakfast, drinking your coffee. Richard left early for work, its just you and I. Denise, why the cha...

The Last American Male

by BuckRivers on Sep 12, 2017
Fetish

Author's Note: This story could reasonably be classified under Nonconsent or Fetish (Tease and Denial) or perhaps even some other category like SciFi. I think Fetish is the best spot, but will offer an apologetic shrug if readers think differently. Happy reading! * "Wake up, sleepyhead!" The guard tapped my bunk with her police baton. I opened one eye and...

My Big Day

by shaveverything on Sep 17, 2017
Fetish

I met Kim in high school and have been attracted to her ever since. She knew how much I liked her but she never gave me the chance. She liked teasing me. Now, five years later, I'm her sex slave. It started a few months ago with daily chat sessions. These consisted of me jerking off while she watched. Sometimes she'd let me cum, sometimes she'd deny me my o...

Misogynistic Man Owned!!!

by Ovid71 on Sep 12, 2017
Transsexuals & Crossdressers

You're sitting in a bar with his friends, talking about how there is this rumor that a pack of women are going around raping unsuspecting men. You all talk about; how all the men who were victims don't ever talk about what had happen that night, nor do they give any details. You say... "I can't believe it", I would tell everyone if I had fucked that many wo...

Danny's Education

by Greymead on Sep 19, 2017
Transsexuals & Crossdressers

"Damn it, Jem! I'm a doctor, not a sissy!" Jemima chuckled, recognizing my weak attempt at humor as I tried to avoid the question. She was still holding the brief, lavender panties out to me. "C'mon, honey. Just do it this once for me, please?" Her big eyes begged more eloquently than her voice, and, though I didn't care to let her know in case it made me...

Med Testing Lab Assignment Ch. 02

by boudin5 on Sep 12, 2017
Fetish

"Please remain where you are, Mister Connors," said nurse Olga. "I'm going to guide Mia through her first prostate exam." My dick was still bobbing from the testicle check, I had never been man-handled quite so overtly, and as she came closer I shuddered to think what this prostate probing would involve. "Now Brad if you would, please reach back and spre...