Prostate Fingering Stories

43,883 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

When Sara Met Bob Ch. 04

by yellowfrog on Sep 14, 2017
Fetish

PART IV: Sara sculpts Bob's lovely penis Days turned to weeks, weeks turned to months and Sara derived ever-growing joys from milking Bob's prostate. The implanted micro-devices gave Sara the ability to massage his prostate remotely, be it from a distance in the same room, to the other end of the bar at the shemales saloon they frequented often, and even ov...

Call Me, Lover! Ch. 02

by twistedthoughts1978 on Sep 14, 2017
Transsexuals & Crossdressers

This is the second chapter of an ongoing fantasy. All people mentioned are 18 years of age or older. I recommend if you are just reading this that you read the previous chapter (Call me, lover.) to get the baseline. It has been almost a year since that Friday afternoon when my whole life changed. The year has flown by with how busy I have been. I had been...

Massage What?

by MightyCasey on Sep 19, 2017
How To

How to initiate prostate massage into your relationship. This is what worked for me without a large amount of ass-pain, pardon my pun. I'm not obsessed with my prostate or anything, but it's nice to have a wife doesn't mind giving me an occasional prostate massage. My wife of twenty five years Gwendolyn is a real cutie, she has always been a great lover...

His First Fingering

by missveronica on Mar 18, 2020
Anal

**After receiving some lovely responses over the years to my other anal story, "She Fingers Him," I wanted to write another that includes some prostate love. Although these stories are not connected, you may notice some similarities. I hope you enjoy both.** ***** She can't help the sigh that escapes her as his tongue circles her clit. His mouth is perfect...

Judi The Cockteaser!

by Bi_Siamese on Aug 31, 2017
Erotic Couplings

I married Judi when I was 27 years old. I was a tall, dark, and handsome stud looking for pussy rather than a relationship. When I met Judi, a blond 110lb. 5ft. 4in. bombshell with beautiful 36C breasts five years my senior and a lot more mature than myself I was easily swayed to submit. Judi was raised as a street smart woman hotel hooking in New York City...

Uncut

by Dann0 on Sep 19, 2017
Exhibitionist & Voyeur

My bout with prostate cancer has mostly been an ordeal to endure. There were a couple of bright spots, including laying spread eagle in the stirrups for a trans-urethral ultrasound, a nurse named Beth making adjustments to the rubber hose hanging out the end of my cock while she took in the view before she started the procedure. And there was also this inc...

The Deal Sammy Made for Rent

by TheLastBrothelontheLeft on Mar 2, 2020
Fetish

Whimpers escaped his lips. In between, he breathed in air in gasps and moans. Each one muffled by the pillow that his face was buried into. Behind him sat a beautiful person. A pair of hands gloved in white latex. They had slender effeminate facial features. Their body was lean and muscular. They seemed almost ethereal, bathed in the dim light of the bedroom...

The Cock Ch. 01

by robertjones on Sep 16, 2017
Interracial Love

Based on actual events. "Are you a Cock?" The words caught me off guard and totally by surprise. First off, who knows me at Asparagus (a nice fusion restaurant attracting a lot of very interesting people during the daytime)? I just stopped and looked up to see a pair of very amazingly attractive african american women standing next to me at my table. I kn...

Matt and Sarah

by Anonymous1forU on Oct 16, 2018
Exhibitionist & Voyeur

They hadn't seen each other in weeks. To say there was pent up sexual energy would be an understatement! They met in the hotel lobby and could barely contain themselves. Matt was tall, dark and handsome. He was 6'4 with broad shoulders and a trim waist. He was dressed in a button down shirt with the top three buttons unbuttoned. His slacks fit perfectly; tig...

Rough Sex - Femdom

by bluejay97 on Apr 15, 2020
BDSM

AUTHOR'S NOTE: These are my original characters, they belong to me, please do not steal. Thank you. _____ I looked into Jackie's eyes, her purple contacts obscuring her expanding pupils. She looked back with an intense stare, and glided towards me, the corner of her lip turning to a smirk. Then, she stopped smiling, and grabbed my face. Her lips parted,...