As people grew more and more comfortable with sharing their deepest darkest secrets online, it opens the door for more and more instances of blackmail. Awful blackmail stories, especially today, often happen over a person's computer, where email chains, private photographs, and personal information all become ammunition for a persistent blackmailer. Marriage-destroying secrets and sex-shaming photographs emerge as a common thread among the worst blackmail stories. Thankfully, not all of these outrageous blackmail stories take such a negative turn. For all the awful blackmail stories out there, there are also funny blackmail stories between siblings and friends that just show tough love takes on many different forms.
On Reddit where people recall times they got blackmailed, each of these stories usually involves a similar theme such as a scorned lover, but they all turn out mighty different from case to case. These outrageous blackmail stories, in addition to being wildly engrossing, remind you why it's always good to keep your receipts in order.
These Kids Grew Up To Be Mob Enforcers
From Redditor u/automator3000:
As kids, my brother and I ran a Nintendo Rental store out of our bedroom. We had one customer - this kinda dumb kid who lived with his grandparents down the street. He "rented" two games one week and then went to spend a week with his dad.
When he came back, we hit him with an invoice for like $50 - late fees and non-local rental fees and all sorts of childhood nonsense. We looked at it as our prime money-making time! That would have been half-a-year's allowance for each of us!
He refused to pay, so we went after him. Stuffed his grandparents' mailbox with dead animals, sent him letters claiming to have naked pictures of him that we'd send to his dad, made false claims to the police.
He eventually paid. It was good.
Taken Advantage Of Via Webcam
From Redditor u/wickornot:
As a young teenage boy - aged 15 on the internet - I was in a weird scene with a bunch of other young guys. We would get older guys to buy us stuff from our Amazon wishlist by going on webcam sites and doing what they asked us to.
I got a friend request one day from a cute boy that I assumed went to my school so I accepted it. Soon after that I got a really angry phone call from a boy at my high school, screaming at me that his whole family shares a computer. I had no idea what he was talking about and hung up, kinda unnerved.
I got a message on Facebook from a friend in my class. She said that the same boy who had friended me had sent her screenshots of me, naked on cam.
I realized he had friended me and could see my whole friends list. About five other people had got pictures before I got an email from the guy. I remember the email address still, because it ended in @sh*ta**.com.
He told me he'd copied my friends list (I had deleted and blocked him as soon as I realized what was happening) and would keep sending pictures to people from my school unless I did what he wanted. Send him pictures and videos whenever he wanted mostly.
I couldn't find his email account anywhere because of the weird URL, so I couldn't report him. I didn't call the cops because I was paranoid I would go to prison for making p*rnography of myself.
I straight-up told him I had been looking for a reason [to] kill myself and thanked him for giving me one. His whole tone changed and he said not to do that because the cops would trace it back to him and he would go to prison. He told me he was 15 too and would delete the photos and not send them to anyone else.
That seemed to be the end of it. He kept messaging me after that and we ended up sorta friends for a while. Eventually we just kind of drifted apart. Still easily one of the worst moments of my life and the main reason I dropped out of high school immediately following this.
The Gay Agenda
From Redditor u/iquitinternet:
When I was 19 I was sort of dating a girl and we happen to exchange a whole bunch of nudes. When I wanted to move on and see other people, she said I couldn't and that she would post my nudes on a gay forum with my phone number if I didn't stay with her. I told her to go ahead and a few days later she sent me an AIM message with all the links to the forums my nudes were posted at. My phone rang for several months from guys looking for a good time. I was really flattered.
The Truth Will Set You Free
From Redditor u/expletiveinyourmilk:
My brother threatened to tell my mom that I had used the Comcast On Demand to watch p*rn. It was free because we had the premium channels at the time.
He made me do all of his chores and kept holding it over my head. After a month, he told me to do something and I told him I was tired of doing his stuff. He said he was going to call our mom at work and tell her. So, I did one better, I called her myself.
"About a month ago I watched a p*rn through On Demand."
"Okay...is it going to show up on the bill?"
"No, it was free."
"Okay... uh... just don't do it again. Okay?"
"I'll be home at six. Love you, bye."
"Love you too. Bye."
My brother was p*ssed that I didn't get punished.