Prostate%20milking Stories

9,406 results
Orientation
Length
Source
Infinite Scroll

What You Need

by Hi_Literotica on Sep 25, 2017
Fetish

This story contains descriptions of domination, pegging and cum-play. If any of these are likely to offend you I suggest you stop now. If not then please read on and enjoy. I appreciate your comments and constructive feedback. ***** My wife was preparing her lunch for work as I finished my morning coffee. I was home for a few days after another long stret...

Smack Ch. 03

by UnknownAuthor on Sep 11, 2017
BDSM

************** ** SMACK -- PART III ** DISCLAIMER ** All characters portrayed are over 18 years of ** age. ** Story contains BDSM, FemDom, Anal and Spanking ************** Liz continues to slowly drop more lube onto my hole and what was now one finger becomes two fingers and the fit is tighter. It feels so good but my ass is on fire from the spankin...

Teased and Denied Ch. 09

by bighouselover on Sep 25, 2017
BDSM

Days turned to weeks and weeks to months. Lori continually teased and tormented my poor cock and balls for hours at a time 3 or 4 times a week. I was milked weekly as usual. Ashley made appearances from time to time but as yet had not brought me another creampie to eat. I was hoping she had forgotten. After a couple of months Lori removed my ball stretcher a...

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...

Grateful Neighbor Ch. 02

by HarryLAbia on Aug 30, 2017
Erotic Couplings

Chapter 2 – Cast off I don't know if she was ashamed of having been so unabashedly seductive, or if she'd found a way to get Paul to help more, or even if she'd figured a way to get by on her own. Regardless, I didn't see Sandra for several weeks after our dalliance. One day, as I was returning home from work, I saw her working in her front garden. From th...

Prostate Massage to Explosive Cum

by Aeiou5678 on Jun 15, 2020
Erotic Couplings

Men are dogs. Plain and simple. If you don't believe it, look at me. As I pressed the elevator button for the floor where my office was located, I reflected, with no small amount of guilt, on my little adventure with my secretary, Mariska the previous day. Gad, why did I let it happen? Why? When I kissed my wife's lips that night, all I could think of wer...

Muscle Mature Fucks Rough Pt. 02

by razmatazz17 on Sep 25, 2017
Transsexuals & Crossdressers

*Thank you to all the lovely people who liked my last story, I just joined Literotica, so it's good to see people enjoying my work. I hope to do more with this series, and different stories in the future, but for now enjoy!* * I slept that night, thinking about what had occurred earlier in the day. I was raped, and I couldn't believe it. My girlfriend want...

Office Fun Ch. 02

by Gellid on Sep 14, 2017
Transsexuals & Crossdressers

Marcia was sitting in the car park of the office, about to leave having just finished work, when she saw Lee walk out of the building and head towards his car. It had been four days since they had fucked in the office, and she was eager for a second round. She checked herself in the rear view mirror before beeping the horn. Lee looked towards her and she bec...

Cuckold CEO Ch. 05

by drdick69 on Oct 9, 2018
Fetish

Day three of our vacation started with a thud. I woke up rolled over and my wife informed me that she had started her period. Well at least I was getting unlocked from my cock cage for a week. Usually, when my wife has her period, she unlocks my cage and lets me jerk off to relieve myself for a week. Sometimes we play sexy games with each other, but mostly i...

Working with Her G-Spot & His Prostate

by LaceySheets on Sep 14, 2017
How To

Spend A Passionate Evening Finding Each Other's G-Spots The G-spot may not be a surprise to some women who have already discovered the ultimate orgasm using this quarter-sized button of spongy tissue of the front vaginal wall. These women may have gone looking for it themselves or perhaps discovered it accidentally during intercourse. If you don't experimen...