Prostate Milking Stories

30,157 results
Orientation
Length
Source
Infinite Scroll

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...

The Restaurant

by ryan_devry on Sep 18, 2017
Humor & Satire

Old Mr Postlethwaite's choice for Henry, of all people, to accompany him to lunch was met with some consternation by the young men at the office. Henry didn't work any harder than anyone else, they felt. He was certainly not smarter than Frank, for instance, or Malcolm, or even William. Then why did Mr Postlethwaite, the man they'd all wanted as their mentor...

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...

Neighborly Love

by glovesnap20 on Oct 6, 2020
Fetish

Though I had always thought that my neighbor, Ava, was cute, it took the loneliness of quarantine for me to finally summon the courage to ask her out. She was in her late twenties, had shoulder-length red hair and wore glasses. Though she dressed somewhat conservatively, her skirts, dresses and cardigans couldn't hide the nice curves of her petite body. In t...

A New Journey Ch. 02

by johnemerson30 on Sep 18, 2017
BDSM

Two days had passed since his wife had him bent over her knees to administer the spanking, and the embarrassment of the whole situation still resonated deeply within him. He was deeply embarrassed by the whole thing, but at the same time his heart raced with excitement every time he thought about it. It was such a surreal situation for him that he didn't k...

Anal Etiquette Ch. 03: Politics as Usual

by CypherWest on Sep 15, 2017
Anal

If you haven't already, be sure to check out the previous 3 parts starting at chapter 00! Also if you like what you read check out Lordodie's series that started it all! ***** Part 3: The Clinic Ashley and I took a seat in the waiting room of our local anal health clinic. I had received the necessary papers to fill out from the pretty receptionist seated...

The Girls College Ch. 04

by TF2123 on Nov 6, 2017
Fetish

Paul followed the two pretty girls through the halls of the school, until they reached a door labelled with a gold plate reading "Nurse Claire Lilly". Jessica slowly opened the door; it led to a small room with a white tiled floor. As they entered, a medical examination table became visible and a beautiful young woman with bright blonde hair dressed in light...

All About Me!

by Freakboy80 on Sep 13, 2017
BDSM

Lisa and Jim were smiling uncontrollably as they left the town hall. "I can't believe we are finally married!" expressed Jim as he held the car door open for his new bride. "I know I'm so happy." replied Lisa. Jim and Lisa had been dating for almost two years. Lisa is a nurse and Jim is a cop. They met one night when Jim had to bring a prisoner in for med...

Teased and Denied Ch. 06

by bighouselover on Sep 25, 2017
BDSM

Sunday morning arrived and I couldn't help but think back to what Miss Ashley had said about seeing me Sunday. I finally decided to ask my wife about it. When I did so, she responded with a very large and sexy grin. I was then told that she had promised Ashley that she could observe and possibly take part in my weekly milking. I blanched at the thought. I wo...

Eddie's Humiliation

by PAS on Sep 25, 2017
BDSM

Eddie Sandler was a good looking 22-year old college senior. He was tall, in good shape with short brown hair and a thin mustache and goatee, brown eyes and overall handsome features. Eddie had little problems attracting the opposite sex. In addition to good looks and a decent bank book, thanks to his parents, he was very sure of himself and demonstrated th...