First Time Cheating Stories

351,288 results
Orientation
Length
Source
Infinite Scroll

One Act Drama

by hansbwl on Sep 12, 2017
Loving Wives

This is a one act drama, or sketch played out in Virginia, in the small home town of: Harry - the lead character and his friends: Zed - considered to be a 0 Bob - he doesn't have a surname, just plain Bob will do, Risq - also called by some 001 (with license to kill) and lastly but not forgotten, Anonymous - the barkeeper. He is a guy who has a comment...

Blast From The Past

by Big Gunz on Sep 14, 2017
Mature

Cathy Spencer could hardly believe her eyes. First last night at the party and now today at her front door. Unbelievable. Terrifying actually. It had only been about 16 hours since she had laid eyes on him for the first time in almost four and a half years. He was only 18 back then, just on his way to university and away from home for the first time, a good...

Something We Have to Talk About

by nici on Sep 19, 2017
Loving Wives

I'm going to try my hand at writing a cheating wife story. I've read some fairly nice stories. But, in too many cheating wife stories I have read, the female characters seemed to either have a full blown narcissistic personality disorder, a histrionic personality disorder or they're so weak and spineless that I can only wonder how they could ever exist in th...

Sherry's Test Ch. 37d

by PolyVoyeur on Oct 8, 2019
Exhibitionist & Voyeur

The next scene had Tammy and me as schoolgirls that were caught cheating. We were both given uniforms that were a couple of sizes too small and damn we looked sexy in our tight white blouse, blue skirt and red plaid tie. Tammy, for those who don't remember, was my protégé who I had mentored and we had both been through some punishment scenarios together....

Anatomy of an Affair

by amyyum on Dec 3, 2019
Loving Wives

Warning: This material may be disturbing to some readers. Discretion is advised. Statistics I didn't know anything academic or intellectual about affairs before I was married. Growing up in a classic American suburban household where academic and athletic achievements were celebrated both for daughters, like me, and sons, it was always assumed that I'd get...

Enraptured by Spanking

by quagmires on Sep 12, 2017
BDSM

On my break at work I often log onto to various spanking websites to drool over stories and pictures. I am always careful to delete my browsing history before finishing my break. So I was startled when Winston, an Englishman who transferred from London to our branch in New York a few weeks ago, sat beside me one afternoon in the break room, and whispered "I...

Cheating Wife & Cuckold Husband #05

by SusanJillParker on Sep 15, 2017
Loving Wives

Please vote. Please give me the support of your vote. I dedicate this story to Walter from Southern California. * Something that all women say one time or another, "How do you like me now?" Later in their marriage, had they not shared the commonality of them both being cheating spouses who were sexually attracted to young, firm flesh, Jay didn't think th...

Is it Cheating?

by AnimatedSocks on Oct 7, 2019
Fetish

It was always hard to focus at this time a day; Five days a week, at ten am, Monday through Friday, for the past three weeks. He didn't know why it happened, and sure as fuck couldn't even begin to explain how. This sort of thing isn't supposed to be possible after all. This was real life. This wasn't some high fantasy setting in which this sort of thing was...

Rebecca Anne

by Just Plain Bob on Sep 17, 2017
Loving Wives

It came at me out of the blue. We had just finished dinner and Becky was washing the dishes and I was drying them and putting them away when Becky said: "Have you ever had an affair or thought of having one?" How in the hell do you honestly answer a question like that? Had I ever had one? No. Had I ever thought of having one? Many, many times. There was on...

Slut - My Wife the Cheater Pt. 01

by NeilMc123 on Jul 30, 2018
Exhibitionist & Voyeur

This a rework and update of an earlier story. *** I walked into the trendy nightspot, heading to the far end of the bar, where I could see Suzi and Jim were waiting for me. I'd been friends with these two for over ten years, and would meet up on a regular basis, mainly to lust after and flirt with Suzi. Jim didn't seem to have jealous bone in his body as I...