Prostate Stories

1,000 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

Prostate Play

by tone12of12 on Sep 12, 2017
BDSM

For instance, she said, did you know that a man can come without ever stroking his cock? Now, usually, this takes a lot of self control, but seeing as you are... indisposed, self control won't be so much of an issue. She ran her fingers down the side of my neck, across my chest and belly. Her tips circled around my cock and balls before drifting under me, ta...

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...

The Prostate Exam Pt. 02

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. She then persuaded him to...

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...

The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing bac...

The Prostate Exam Pt. 06

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

"Just as it should be, now walk to quickly to the Langham hotel. Make sure you keep the bag out in full view, for all to see, it cannot go in your back pack. I want anyone who sees you to know what a slut you are.." "Go straight to the bar and order a triple G&T and 3 shots of good tequila. If the bar man asks you what you're doing you will tell him that yo...

The Prostate Exam Pt. 05

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Since giving himself away in his first prostate exam to his Dominant Doctor Megan he had been prepared for use by an old Master, now Sissy was on her way to be used. Sissy was breathless as she read the text from Master V, she looked around the small airport to make sure she didn't know anyone, whilst she was looking at her texts. Thank goodness she didn't....

The Prostate Exam Pt. 03

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by pushing back against her finger, his female doctor had decided to test just how submissive he was. She gave him the option to back out if he didn't want to go any further, but she told him that if he did want to go furth...

My Prostate & Me: Alone Together

by lord_jefe on Sep 18, 2017
Toys & Masturbation

For my fans: You'll notice no number on this story, and that it's in the Toys & Masturbation category. The reason for this is that it's just me & my prostate right now, not in the past. The general tone of the story is pretty sad, but it improves, much like life. Times have changed. I'm 40, unemployed, and living with a family member since the wife left....

My Prostate & Me Ch. 03

by lord_jefe on Sep 18, 2017
Anal

If you haven't read the previous parts to this story -- I'd recommend it, as it explains a lot. I'd also recommend voting & feedback, as it's the only way I have of knowing if anyone is reading or liking this. And I realize this one starts off kind of unerotic. Bear with it. It cooks at the end! * Well, I had been ass fucked with a dildo. When all was sa...