Cuckold Risk Photo Roulette Stories

60,689 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

Roulette - Round 01

by EmeraldCoastGuy on Oct 5, 2020
Erotic Couplings

Ashley Winters -- 21, blond, and fit - walks out of a big box office supply store clutching the paper bag that contains a completed school project for one of her last classes before her graduation from Seaside Community College. As she's about to step foot into the parking lot she sees a familiar face walking towards the dollar store next-door. Ashley yells...

Roulette - Round One

by EmeraldCoastGuy on Jul 13, 2020
Erotic Couplings

Ashley Winters -- 21, blond, and fit - walks out of a big box office supply store clutching the paper bag that contains a completed school project for one of her last classes before her graduation from Seaside Community College. As she's about to step foot into the parking lot she sees a familiar face walking towards the dollar store next-door. Ashley yells...

Wife Makes Friends at Casino Ch. 01

by altego on Sep 13, 2017
Loving Wives

I greatly appreciate the assistance of my editors for this story. Firstly, Angle Love. She does a great job of gently correcting my grammatical mistakes and making this a better-written story. If you find any mistakes in the finished product, I assure you it is a change I made after her review. Secondly, P_A_Solcrofft. He does an outstanding job of reviewing...

Caravan Park Roulette

by nikki_2021 on Sep 14, 2017
Group Sex

"What the fuck is caravan park roulette?" Mandy demanded as she took another drink. "Its like this," Jenny replied, "You sneak into the men's shower block of the caravan park, slide under the door when some bloke is in there and give him a blow job if he lets you." "No fucking way!" Mandy laughed in response. "You've never done that," Emma said with disb...

Mercury Retrograde

by MSTarot on May 30, 2018
Sci-Fi & Fantasy

Big Alice was always hungry. And with her skilled hands on the controls it was Stephanie "Roulette" MacBaren's job to keep the big bitch fed. Following a path laid down by two seasons of steady work, Rue guided the insanely massive paddle wheel excavator on its way up and over a lobate scarp that made the big machine work for its meal. The slow turning bl...

The Thrill of Online Exhibitionism

by like2bewatched on Aug 31, 2017
Exhibitionist & Voyeur

This is the story of my continuing exploration of my exhibitionist desires. My earlier submission described how this temptation was first awakened during an innocent encounter in a bar. Since that time (and with some encouragement of friends on this site) I have tested my limits in a few of situations -- though I continue to be a pretty conservative, risk-av...

Cuckold Ch. 01

by Sammi_the_Seal on Mar 23, 2020
Loving Wives

Tom This is it! The moment I clicked on the "Upload Picture" button, all hungry eyes would be able to see my wife, Melissa. I hesitated - my heart thumped in my chest as I looked at the screen. Just then, I received a message in my inbox. It was from John_the_Bull, a man that had read one of my fantasies in a FetLife group. John_the_Bull: Hey Tom, when ar...

Spinning

by quirkyqueen on Sep 17, 2017
BDSM

"I am really going to do this...Really?!" I say to myself as I am close to pressing the 'Enter' button on the totally black and low tech looking website. The website looks as if it hasn't been updated since the late 90's, but it has written postings from just yesterday. There are no photos except of a brightly colored red door with a curly whip knocker. The...

The Arrangment

by Iwroteathing on Mar 2, 2020
Exhibitionist & Voyeur

It had been two years since Christine Andrews first saw her name on a brass plaque in the New York offices of HNF investments. She had been in charge of a lucrative hedge fund portfolio for some time and, as she predicted when she first got the job, she was almost completely uninterested. Christine had actually made news when she was in college as a financi...

Business Trip

by BobNbobbi on Sep 17, 2017
Loving Wives

Author Notes: This is a work of fiction; people and events take place only in the mind of BobNbobbi and nowhere else. As story, Business trip has no before or after; what you see here is all there is. There is also no consideration of why or of consequences. Those who do not care for the theme wife and lover other than husband will really not care for this s...