First Time Cheating Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

First time cheating

by wanderingeye67 on Sep 23, 2019
Erotic Couplings

We’d been married a while. Well, 26 years is a while, I guess. Like every other couple out there we were on fire at first, then the sex life started to wind down a bit as we settled into our lives. Karen’s older than I am, by about 10 years. It was never a problem until she was in her 50’s. Then she became less and less interested in sex. By the time I was...

First Time Cheating

by bdavidson on Jul 27, 2020
Erotic Couplings

After our third child was old enough to go to school, my husband wanted me to go back to work. He had a good job with an engineering firm, but felt we needed the extra income, so like a good wife I agreed and started to look around. As luck would have it, a construction company down the street was looking for help in their office, and after an interview I wa...

His First Time Cheating On His Wife

by elainepwl on Sep 16, 2017
Mature

If you haven't read the first part, I hope that you do. I had a wonderful time writing it, as it was my first attempt to write from the man's point-of-view. Based on the responses many of you sent, I was fairly successful. This picks up from where I had given, and taken, some great oral sex with my boss. He is much older than I am, about the same age as my f...

My first time cheating Pt. 01

by housewife_barb on May 12, 2020
Loving Wives

I first met my husband to be when I was young, he is 8 years older than me. He was my first man that I had sex with. Our first child came pretty quickly, just 11 months after our first date. Like any couple at first we made love all the time. This quickly dwindled during my pregnancy, though I did partake in blowjobs. Which my future husband seemed to prefer...

My first time cheating Pt. 02

by housewife_barb on Jun 1, 2020
Loving Wives

All my submissions are Taken from my personal Journals. Part Two... Sitting on the loo, I didn't know what to think; I felt good, satisfied, really satisfied, but I knew I'd cheated on Tom. Did I feel guilty? Yes and no. I just sat there and re-buttoned my blouse, pulling it across my nipples which were still stiff and a bit tender from Simon's biting. I g...

My First Time Cheating

by KimCate on Oct 12, 2020
Erotic Couplings

I had just turned 19 at the time that this happened, and even at that point I was already rather well experienced in all things sexual compared to many girls my age. I had been called the Two Week Wonder during high school because I'd date a guy for two weeks and usually put out, then dump him and move on. I thought it was the proper way to do things after a...

Cheating Husband-First Time Cheating

by MONALISALEE on Sep 26, 2017
Interracial Love

I am 42 years of age and from Singapore where there's lots of Indians, Paki and Bangladesh come to work. My husband of 15 years, is an agent supplying foreign workers to construction companies and me sort of helping him as a secretary cum accounts. He is mildly mannered when he is sober but when he had too much to drink, he would sometimes abused me which as...

My Wife First Time Cheating

by Maro-lb on Apr 22, 2025

Part 1. Six years ago on our wedding anniversary day my wife and I decided to spend our day on a private beach for adults where I had booked a private section with a double bed and a big couch between the beach and the pool that can be closed all around with curtains any time needing our privacy. Seating on our couch having some drinks pulled my hand from he...

The First Time

by FaithfulJulie on Sep 14, 2017
Loving Wives

After many years of marriage; our sex life was almost gone, we were having sex ones a month or less, and was kind of boring. He just got on top of me; pound me for a few minutes and finished, while cleaning up myself in the bathroom, I will use my consul, (vibrator) to pleasure my self. I was at that age when women wanted to be sexually desired and to have...

Cuckold Couple Ch. 02: First Time

by CuckoldingCouple on May 20, 2019
Loving Wives

Angela left our house at ten thirty in the morning and to my surprise she was back just after eleven. I had wondered whether Angela would go through with it or not, it seemed the latter. I was partly relieved to be honest, maybe this wasn't such a good idea after all, it could lead to all sorts of problems. However, I hadn't been able to think of anything e...