Your cheating stories

screwher

Literotica Guru
Joined
Mar 17, 2012
Posts
13,389
Over on the General Board a new thread about cheating stories was started. I got excited only to find it quickly turned into a goof thread about cheating on taxes, diets, etc.. So I’m starting a proper thread here about the subject.

Share with us your experience about cheating. Did you ever cheat on your spouse or (long term) girlfriend/boyfriend? Did your significant other cheat on you? Please share some details - Who? When? Where? And what were the ramifications ? Positive or negative?
 
Over on the General Board a new thread about cheating stories was started. I got excited only to find it quickly turned into a goof thread about cheating on taxes, diets, etc.. So I’m starting a proper thread here about the subject.

Share with us your experience about cheating. Did you ever cheat on your spouse or (long term) girlfriend/boyfriend? Did your significant other cheat on you? Please share some details - Who? When? Where? And what were the ramifications ? Positive or negative?

Bumped. I’m sure there’s lots of stories out there.
 
hey ...

Bumped. I’m sure there’s lots of stories out there.

I know for a fact there are--, I just can't tell any of mine. Its been five years since anyone come looking and asking for someone with my name. I kinda like that level of anonymity. It is no fun waking up to the law at your door.
 
For a few years, I was dating a lady who was the sister of my neighbor. Well the neighbor turned out to be insanely jealous; whatever her sister had, she wanted. Including me. Whenever my GF spent the night at my place, as soon as she left in the morning, my neighbor would come over and insist on having sex with me. She always wanted to be my "most recent" fuck. I knew it was wrong, and I should have refused, but.... well, you know.
 
A few years ago I had met this guy off a sugar Daddy dating website. We ended up hitting it off and eventually he offered me a job working at his dental practice. His wife was always coming in office to drop him off food or just stop in to say hi. I always felt so two faced being so sweet & nice to her when she was there, and in back of my mind knowing I’m fucking her husband. She ended up finding pics of me on his phone, which got her to place a tape recorder in his personal office. She eventually had the audio of us having sex in his office. She contacted my boyfriend on Facebook and told him everything. I was promptly fired they separated for a short time but ended up working on things and got back together.
 
Some years ago my wife went off sex for quite a while, I went looking online for sex elsewhere. I started chatting to this woman who had recently separated from her husband as she was in a sexless marriage. I met her one morning at her place and I didn't know what to expect, we chatted then started kissing and we went to her bedroom. She was quite wild and I could see she was letting all her frustrations out. We met for a while regularly and I would turn up and she would be naked and ready for sex. She was quite loud as well so I don't know what her neighbours thought.
 
Years ago a girl I was working with started throwing herself at me. I knew she had a boyfriend but she wanted to hang out. I mulled it over and eventually she did come to my place and we fucked. That led to me banging her at her place when her boyfriend was at work....multiple times. One time I remember he called her on the phone and she spoke with him while I was inside her.

He did eventually find out and got angry. But I believe they stuck it out and are now married with kids. (Hopefully his.)
 
A few years ago my wife and I fell on some hard times. She ended straying and started to screw a guy she worked with. I found out, I was mad at first but decided it was a two way street. So this girl that worked with me, she was around 21, we started to talk. She would flirt a lot with me and I flirted back. One day she invited me back to her place that evening, I went and we ended up screwing the entire night. I almost forgot about what 21 year old girl is capable of, but I kept up with her. We continued seeing each other for a few months until she transferred out to another location.
 
If you've read my posts you know that I was a cuckold with my 1st wife. One time I encouraged her to sleep with a married friend of ours that we had just met and they did a few times, I got to watch once, but, it ended after his wife almost caught them during a pool party at his house.

Fast forward 3 years, he'd become my best friend, the 4 of us hung out and partied regularly, but unknown to either of us spouses, their sexual relationship had picked up and they'd been fucking for almost a year when I got suspicious after a drunken night out clubbing when the 2 of them disappeared for a while. She finally admitted the affair, with no apology, and is happy to tell me all the details especially how many times I'd eaten his cum from kissing her after she'd blown him (sometimes while he was there watching her kiss me) or how she made me eat her pussy while it was full of his cum. She tried, and actually did a good job, to destroy me with stories of how much of a better lover he was, how much bigger and better his cock was (I'd seen it and it was true). Then when I went to talk with him at his private office, somehow he got us watching porn together, and I ended up sucking him off. It had been years since I'd suck off a man and I was actually pretty desperate to do it and very venerable from the way my wife had been treating me, so, I really went to town on him choking, gagging and drooling like a cock slut. Of course he told her and she used it as another way to humiliate me. We divorced a few months later and they are still married to this day.
 
I had been off sex for quite a while and at the time I was working in an office with a few people, one of the guys was quite friendly and after a while I confided things to him and he did the same with me. His wife had also gone off sex as well, one night we went for a drink after work and he was getting a bit flirty with me. I somehow liked it, since me and hubby were not being sexual he started to not bother with kisses or cuddles anymore. I was enjoying this guy taking an interest, he gave me a lift home and before I got out of the car we kissed and I enjoyed it.

We talked some more and one day he asked me back to his house as his wife was away. As soon as we were in the house we were kissing and touching each other we went up stairs and we were soon naked and all over each other. The sex was so intense and after the first time I wanted more. We carried on seeing each other before I realised that I should be having sex with my husband. This guy was nothing special as in he didn't have a big thick cock or any kind of technique that would send me wild. I think it was just the fact I was discovering sex again. I ended it and told my husband about it, he told me about his affairs as well. It took time but we worked through it and it led us to explore many different things.
 
^^^^^

I think this may happen more often than people realize. Sometimes all it takes is a little something extra added to the mix. Just a little jump-start to get things fired up again.
 
The first time I cheated on my husband, It was with a crush from high school. We reconnected. We started chatting on line. I made some boudoir pictures for my husband and decided to let him take a look. Right after I sent him the pictures he has if I was available to chat. My husband was downstairs so I said that I did. Halfway into our conversation he asked if I could show him some skin. So I took off my shirt and he started masturbating. It's the first time I've seen a man do that to me since I've been married. I joined him. We did this a few times before he asked if we can meet up at the gym we both go to and we can work out together. At the end of the workout he asked if you can see my tits for real. I told him that I didn't want everybody else seeing them. So I drove him in my car behind the gym in a secluded area. I took off my sports bra and he started grabbing them. I saw him tenting his shorts. Then he told me to get out of the car. When I did, he threw me over the hood and hold down my shorts and my underwear and banged me from behind.
 
I had a little fling with a woman when I went to Grad school one semester. She was a very outdoorsy type, we did it doggy style a lot...lol. My wife was a bit suspicious...but quit worrying about it.

Few years prior to that, my fair lady had a one night stand with our good friend, while I slept off a marijuana high. They managed to do it six times while I dozed away. My only regret is they didn’t wake me up to watch or participate...lol.

Fast forward a few years, and she had an ongoing thing with a coworker, that lasted for nearly two years. It was kept secret for awhile, but ultimately I was informed and had no problem. It was sort of a sexual awakening for her that was needed to overcome some bad experiences from her childhood. Turned to be therapeutic to have a purely sexual experience with no strings attached. I was glad she had such a great experience.
 
My wife and I started dating in high school, but went to different colleges. She was free to date others, although we were in love, and she had sex with several guys for two and a half years until we got engaged. Then she was totally faithful. After we had been married a few years, we talked about her experience with other men and I asked if she missed the variety. She said, "no," but I gave her permission to try other men if she wanted to. There were a few ground rules, and I gave her a few condoms, just in case. She worked in a medical office and was constantly being hit on by sdales reps and others. Finally, she agreed to meet one of them at a medical convention in another city. She was in her 30's and he was in his 20's. They had fun sex at the convention. She did the same thing with another young sales rep at another convention. After a couple more experiences, she decided she had enough. It wasn't really cheating since she had my permission, and she still has a hall pass to do whatever she wants. She chooses not to be with other men or women.
 
While living with a girlfriend, her older married sister came to visit from San Diego where her husband was stationed. Both sister were petite and fit, with the older sister being slightly bustier. One day while the gf was at work, the sister and I were hanging out, watching tv and I started giving her a shoulder rub. One thing led to another and soon I had her stretched out naked on our bed while I gave her an all over body massage including breasts and ass, and fingering her pussy until she came.

I managed to do this a few ore times of the next few years before her sister and I broke up. Still regret not trying to slip my cock into her tight pussy.
 
After a couple of years discussing it and talking through all the likely outcomes my wife and I decided to try what was then known as wife swapping. We set up a profile and started meeting possible couples for swapping and guys for 3'somes.
As it worked out our first adventure was a 3'some with another guy, this was an MFM, both guys focussing on giving my ex the best time she ever had. It was highly successful, she loved it and the scene was set for our future.
We kept meeting couples as well with a view to a proper swapping but each couple we met either one or both of them were too old, too young, too fat , too thin, too ugly, too beautiful, tit's too big, tits too small, too tall, too short. Over the next few months there was never a perfect couple and it started to dawn on me we were never going to meet the right couple to swap with.
Meantime she was enjoying her regular 3'sums, as i was, but I was starting to feel aggrieved that while she was getting all the cock she wanted I was missing out on a bit of extramarital pussy.
So, I decided to take matters into my own hands. I put up my own secret profile. I was completely honest about my marital status and circumstances and started meeting women and couples for sex. I had no problem finding partners and I felt i had evened up the game.
I would have much preferred to have had my ex participate fully in the fun but after a couple of years she decided that she didn't want to even try swapping, she still wanted her 3'sums though and she said to be fair she was happy for me to meet others by myself so I could have some fun as well. As you can imagine I was very happy with this idea. I was able to stop hiding my cheating and it became legitimate.
We carried on with our "open" marriage for another 18 years when we did eventually split up. She never learned that I had spent a couple of years regularly cheating on her.
 
Is it wrong?

Is it wrong I have so many. I guess it’s not cheating cause most were prior to my marriage but I tended to be that guy. First time I can remember I was 20 and I had this amazing 36 year old “single mom” type neighbor. The chemistry was obvious between us. I would cook out with friends and invite her and her two kids over for dinner what have you. My friends thought it was cool I had this hot neighbor and so did I. I think she liked the fact she was hanging out with a much younger crowd. All kind of came to a head one night when I was just doing my nice neighborly thing and she and her kids were hanging out watching a movie after I made a dinner. It was late and she said it was time for her to go. I carried one of her asleep kids across the street to her home and she asked me to come in. After I handed off her little ones I was told to “not leave yet” and she settled them down. It was late like 1am. She came back into view and asked me if I wanted to watch a movie.... thinking Netflix and chill I was super stoked. That’s exactly what it was for the next few weeks until one day I saw a different car in her driveway. Observing over the next day or so I realized that she was married and it was her husband that had came home. We actually hit it off and he was a cool dude and he thanked me for looking after his kids and treating them nice. Not ever sure if his wife mentioned what went on between us the passed month. Two weeks later they moved never to be heard from again.
 
Last edited:
Back
Top