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

• (#24) She Cheated With Her Son's Roommate

  From a former Redditor:

  So my old roommate's mom cheated on her husband (roommate's dad). They had been together for 40 years and she [banged] some guy in her daughter's bed while the whole family was downstairs at a party. No one found out but it was pretty [crappy] of her to do. I was the guy she cheated with.
• (#2) He Cheated With His Cousin

  From Redditor u/haibane_rakka:

  Someone I know is getting a divorce because her husband is having an affair with his much-younger cousin. Apparently the age thing isn't as big a deal (legally) in their location as the family thing, but the whole situation is all sorts of f*cked up.
• (#7) She Cheated In An Asian Restaurant Right Before Her Wedding

  From Redditor u/Anglicanweasel:

  My boss, an enthusiastic outdoorsman and very gentle fellow, comes to work one day with a black eye and puffy face. I ask him what happened, he explains that there was a fist fight at the AGM of his Hunt.

  Apparently there was a member who had recently split from his wife. They had just married and had had their first child. Unfortunately for their marriage, the child was born Asian. Both husband and wife in this instance were Caucasian. This chap didn't discover this until the child was born, whereupon his wife confessed to committing an act of desperate passion on the floor of an Asian chip shop with one of the staff during her hen night (bachelorette).

  My boss was injured in the fracas that erupted after one of the members of the Hunt decided that four months after the fact was long enough and he could crack a joke about it during his speech to the assembled members of the Hunt.

  He claimed afterwards that George had no sense of humor.
• (#19) He Cheated With His Wife's Maid Of Honor

  From Redditor u/Jesus_Faction:

  A friend of mine was dating this guy for seven years before they finally got married. They got divorced after one month of being married because she found out that he was cheating on her with her maid of honor. The maid of honor tried to get him to go for alimony too.
• (#26) He Cheated With His Student Right After His Wife Gave Birth

  From Redditor u/heyrubyway:

  A high school friend of mine was that kind of really hot tall blonde girl that made all guys [go wild]. She loved getting attention and I think she especially loved flirting with guys that were out of bounds, like she seduced several guys who had girlfriends. I guess she just didn't really care about other people’s feelings.

  But the worst was that she started an affair with her high school math teacher in our last year of school (she was 19, he was about mid-30s). He had just married his wife who was pregnant at the time. Girl and teacher wrote emails back-and-forth for months. The first time they met up.... with each other was the night that his wife gave birth to their son. So he stayed with his wife and son in the hospital until the evening, then left to go home [to] one of his students... Still makes me stick to my stomach how someone could ever do that to their partner.

  The wife found out eventually, but after a little break they’re still together now, seven years later.
• (#28) He Bought His Mistress Plane Tickets With His Wife's Credit Card

  From Redditor u/B0TTiG:

  I work at a call center for an online travel company. First call this morning was from a woman claiming that there was a fraudulent charge on her account from our company. She supplied the credit card number and I was able to pull up two round-trip tickets purchased a week ago. They were going to a casino for the weekend, and this was the first his wife had heard of it.

  She said he denied making the purchase and had no idea what it could have been for. Once she realized what was happening, she blurted out a name that matched the name on the ticket. Apparently, there was some history, because she was able to identify who he was taking on the trip without me saying.

  The icing on this... cupcake was that he posted a review for the trip in our system. He said that he didn't take the trip yet, but was excited to spend the weekend celebrating his new love's birthday at the casino. I couldn't tell this to the woman on the phone... she was already incensed and did the best she could to be polite as we ended the conversation.

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