Random Craziest Cheating Stories People Have Ever Heard (30 items)

• (#13) He Took His Lover On The Honeymoon He Bought For His Wife

  From Redditor u/bloodthirstyllama: 

  My old housemate was engaged to a guy and had just taken out a mortgage on a house together. On Christmas Day, after eight years of being together, he told her that he didn't love her, hadn't for six months, and was sleeping with his secretary. She breaks down, he gets [mad] at her and tells her to sleep on the coach and then tells her to move out the day after.

  Two months later he is officially with this other girl and takes her to New York, the planned destination for my housemate's honeymoon.
• (#29) He Rented Out Adult Videos For His Mistress On His Wife's Account

  From Redditor u/HeroOfTime1987: 

  Worked in a local video store when I was in HS. About once a month or so a customer would come in with this attractive looking blonde woman on his arm. They would rent [adult videos] and scurry off into the night. Due to the fact this was the only store in a few miles, we were popular with the locals. Needless to say I knew this man as the father of a kid from my class.

  Anyway, one random day when I'm not paying attention, a woman comes in to rent a video. She gives me her card, I scan it, and see there is a late charge. She asks what movie it was so she can find out whether to ask her son or daughter to pay the fee when she gets home. I look up the title... and turn the screen towards her so I don't have to say the title out loud in front of other customers. She gets red-faced and asks if there was any way her children could have rented this. I check the account info and that when I see the last name. I'm sure I turned just as red as her as I started to put two and two together, at the same time as this woman. I tell her I know her kids aren't of age so there is no way that we would rent [this video] to them. She asks for a print out of the rental history and I gave it to her even though it wasn't allowed.

  Felt so bad seeing that kid depressed at school a week or so after.
• (#22) She Cheated On The Kitchen Counter With Her Boyfriend's Little Brother

  From Redditor u/sadeqsr:

  My ex and I were dating for two-and-a-half years. I came back from a business trip without telling her when I was coming home so I could surprise her, I walked into my apartment saw her [banging] my younger brother on the kitchen counter.... I was devastated, my...brother didn't apologize or anything. I just grabbed my stuff and walked right out.

  Still hurts thinking about the situation as I'm writing this.
• (#21) His Kidneys Messed Up While He Cheated With His Wife's Friend; It Was Also Their Anniversary

  From Redditor u/fingeredbykreuger:

  My ex-boyfriend told me he had to work on our anniversary which also happened to be the night before my birthday. I was disappointed but whatever. Next day he told me his kidneys (he has a bad kidney problem that gets worse when he drinks) were acting up and he couldn't come to my birthday dinner.

  Came to find out he was drinking and [getting with] one of my best friends the night of our anniversary.
• (#23) He Didn't Know His Girlfriend Was Setting Him Up

  From Redditor u/lewismacp2013: 

  My brother's friend had been talking to another girl in a dating website for months. Finally his girlfriend asked him if he was talking to another girl. He said no. She confessed that she was girl from the website.
• (#10) She Cheated On Her Husband With An Entire Family

  From Redditor u/Xenophorge:

  I knew this girl who took the prize home. She gets married to my buddy right after graduating HS. He joins the military, goes off for training, she starts [messing] around on him with this one guy. Then, she breaks it off with the guy she was [messing] around with to start [messing] around some more with his older brother.

  My buddy is still getting trained here, making bank all the while (and she's spending it as fast as he can earn it). She stops [messing] around with the older brother, steps up to their father! Now she's [getting it on] the father, he talks her into becoming a [dancer] at the bar he worked at, and she gets up on stage for all of us to see. Some nights, he brought her and other girls home for [good] times. All the while married to my buddy, who dropped her.... finally as soon as he came home.

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