Risky Stories

7,016 results
Orientation
Length
Source
Infinite Scroll

SMS 1: Primer

by Will Scarlet on Sep 19, 2017
BDSM

How should I begin? How I got to be in the position that I am in, and with my relationships such as they are, is a story I'll leave for another time. Let me tell you how things are. My name is William and I am 33. Kerry, my girlfriend, is 25, and her friend Fiona is also 25. We live in Edinburgh. I encourage Kerry to dominate me, and discuss me openly wit...

Lisa

by moonlight on May 22, 2016
Erotic Couplings

Disclaimer: All persons in this story are 18 years or older. It is a fictional world. Highschool girls are at least 18 years old. You are playing Lisa Meier. She is a highschool student in her first year. She is transfering to Saint-Etienne Academy a co-ed private catholic school today because her mum did find a new job as a secretary for a major law firm in...

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Keeping it a Secret

by Noi Jetat on Sep 17, 2017
BDSM

I thought I had kept things under wraps. I even had myself convinced that I took the job at the tack shop because I needed money. It's true, I did, but the truth is I had to hide a hard on every time I had to stock the riding crops. My boss, Jenny, was decent as bosses go. She was always friendly, and kept the discussions to work stuff. A nice arm's length,...

Risky Roleplaying

by RockHerWorld on Oct 15, 2018
Erotic Couplings

After booking my flight for the dates Mary suggested sending her my itinerary and getting a text back with a calendar showing the date I would arrive with a big green "O" one days later making it clear how fertile she would be and how risky the roleplaying would be knowing I would go wild thinking about being with her again and would be like an insatiable wi...

At the Amusement Park

by sparkle8 on Aug 31, 2017
Exhibitionist & Voyeur

It's July 4th, and there is going to be a fireworks display at Six Flags. Not just any display. This year they hired Liberty Fireworks, the best fireworks display group in the nation. We've been looking forward to this event for a month. The fireworks are still an hour away, so we are wandering the park, enjoying people watching, trying to knock down some c...

Male Bridesmaid

by pervy-young-prof on May 22, 2019
Erotic Couplings

Note: Some of the story will be path-dependent. It'll only make sense in the later stages if you play using Game Mode. SCENE 1: THE BAR You and Sara are sitting at a table in your favorite dive bar, and it's happy hour. In a week and a half, Sara—your ex, but also your good friend, now—is getting married to James. Tonight is the last time before the wedding...

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Sex in Public and Risky Places Ch. 02

by walterio on Sep 26, 2017
Novels and Novellas

Author's Note: Over the years I have had sex in interesting places, some public and others risky. As I reflect on those days past I realize just how risky some of those encounters were and how fortunate I was not to be discovered. Others were not risky but wild and exciting as they took place in a third party's residence with the person in the other room. I...

Sex in Public and Risky Places Ch. 06

by walterio on Sep 26, 2017
Novels and Novellas

Author's Note: Over the years I have had sex in interesting places, some public and others risky. As I reflect on those days past I realize just how risky some of those encounters were and how fortunate I was not to be discovered. Others were not risky but wild and exciting as they took place in a third party's residence with the person in the other room. I...

Sex in Public and Risky Places Ch. 05

by walterio on Sep 26, 2017
Novels and Novellas

Author's Note: Over the years I have had sex in interesting places, some public and others risky. As I reflect on those days past I realize just how risky some of those encounters were and how fortunate I was not to be discovered. Others were not risky but wild and exciting as they took place in a third party's residence with the person in the other room. I...

Sex in Public and Risky Places Ch. 01

by walterio on Sep 26, 2017
Novels and Novellas

Author's Note: Over the years I have had sex in interesting places, some public and others risky. As I reflect on those days past I realize just how risky some of those encounters were and how fortunate I was not to be discovered. Others were not risky but wild and exciting as they took place in a third party's residence with the person in the other room. I...