First Time Cheating Stories

351,288 results
Orientation
Length
Source
Infinite Scroll

Never Say Never

by trigudis on Jul 16, 2019
Romance

Richard Edison wakes up the same way he always awakens after dreaming about his ex-girlfriend Juliet Zeboskey—frustrated. It's the same basic dream every time. He and Juliet meet up somewhere, then begin to make-out. Things get hot and heavy, reach a certain point, then it all comes crashing down when something intrudes or, as in this last dream, Juliet simp...

Perfect Marriage?

by taylorsam on May 7, 2019
Loving Wives

This story is complete fiction and represents a departure from my usual style. My hubby and I collaborated on this piece going down a dark road. Hope you like it. As always, constructive criticism is requested and welcomed. They say there are signs when your spouse is unfaithful. "They" are right, I just missed them till it was too late. My name is Robert,...

Revenge in Advance - Derby's Dose

by saddletramp1956 on Dec 11, 2018
Loving Wives

The following is a continuation of the saga based on edrider73's 2014 story, "Revenge in Advance," in which a wife purchases an insurance policy that ultimately details the revenge her husband would face if he was caught cheating on her. In a nutshell, Oscar, the husband in the story, learns that if he were to be caught cheating, he would essentially be kidn...

Slut: Teasing is My Game

by NeilMc123 on Jul 14, 2020
Loving Wives

I've just completed my chosen ensemble for this evening and I'm now standing in my bedroom, looking at my reflection in my full length wardrobe mirrors. I was just about to twirl around to view the full reflection of my pink PVC lingerie clad curvaceous body, when my husband walked into the bedroom, stopped at the doorway and sighed. "Are you really weari...

It's All About The Cheating Ch. 01

by DickThePimp on Jul 14, 2020
Interracial Love

It's All About The Cheating 01 By : DickThePimp New series all about the wacky world of cheating... Every story has the same theme, but a different cast just like Trailer Park Sex Addict "Hurry up, before James gets up. Oooooohhhhhhhh.... Uhhhhhhhhhh... SHITTTTTTTTTT!!!!" My girl Hazel is riding my buddy Spence's fat white dick in his trailer across the p...

What Men Want Ch. 03

by almost on Sep 1, 2017
How To

What Men Want Chapt 3-Why someone cheats, another chapter in the Almost series. Foreword: I titled this, They vs He or She because the causes of cheating are somewhat bipartisan. They don’t vary by gender, so, if she’s doing it to you, or he is, it’s for somewhat the same reason, and although those reasons can vary, some are listed below, or the one’s I’ve...

A Strange Car in the Driveway

by dimaggio5 on Sep 19, 2017
Loving Wives

I came home early from a business trip and found a strange car in my driveway. Now, I've read enough of these stories to know what that means. It's a cliché for a reason. Rather than just barge through the front door with guns blazing, I figured I'd do a little detective work. I parked my car down the road and backtracked to the rear of our house. I crouched...

Sex, Lies, and Confusion Ch. 02

by The Wanderer on Sep 14, 2017
Loving Wives

There we were eight of us at the diner, all of them were Caitlin and my closest friends. Our host's where Jimmy and Linda Lange, then there was Phil and Carla Thomas, Tony and Jean Marsh; my wife Caitlin and myself. Whilst Caitlin assisted Linda in serving the food, the rest of us made small talk. We all knew that when we had finished the meal the subject of...

Slut: Starts Dating Again Pt. 03

by NeilMc123 on Sep 13, 2017
Loving Wives

We climbed in to Neil's car, a 5 series BMW, with Neil insisting that my dress be above my waist revealing my pussy and stocking tops, and inserting the handle of my hairbrush into my cunt on the journey to my house. Like a good slut, I willingly obeyed, slipping the brush hand in and out of my smooth pussy, legs wide apart and spiked heels resting on his da...

Nothing to Talk About!

by likegoodwine on Sep 14, 2017
Loving Wives

By Likegoodwine copyright July 2013 Here's another story for you, a bit longer than my usual ones. I often write stories that depict characters that are a bit extreme. This one reflects more a normal kind of guy. There is cheating in this story but no revenge: only sadness then hope. The wife isn't burnt, not even scalded. She will just be forgotten. Thank...