I am the oldest of four siblings. One brother 3 years younger, a sister 10 years younger, and a brother 12 years younger. These stories all involve the older little brother, who is also the star of this post. Believe it or not, we are pretty close, but he is a never-ending source of hilarity.
Not sure how this one started, but he and I used to beat the fuck out of each other all the time. We were wrestling around upstairs. I may have been 13ish, him 10ish.
My brother was just getting to the point where he was strong enough to hold his own against me, so I grabbed the remote control and started hitting him with it. He wrestled it away from me, sat on me, and tied my hair around the bannister and then tied my wrists together so I wouldn't be able to get to them (this was a typical strategy). I squirmed around, ripped the railing out of the floor with my (apparent) Samson hair, grabbed the remote control and launched it at him. He ducked, and it got lodged into the drywall behind him.
After being grounded for the rest of our lives (or, just...a long time), the remote control remained stuck in the drywall. When we pried it out a couple years later, it was broken forever and we never had a remote control for that TV again. It was an old school tube TV, and my parents kept it way longer than it was relevant - all until the younger baby siblings were almost grown up. They kept it around as a memento for the younger ones - remember how stupid their older brother and sister are.
My brother told my parents I'd had a raging party when they went out of town when I was in high school. What a little narc! Anyway, as revenge, I stole his retainer and threw it away. That doesn't sound so bad, except I knew that my mother would just ruin his life over it and she did not disappoint.
He had to do all six of our laundry for 6 months to pay off a $90 retainer, and gets to listen to my mom tell everyone this when she talks about how ill behaved all her children are - STILL, 13 years later.
I bought a car, with my babysitting money that I'd been saving for years - and my dad matched my funds. I was 16. Quickly, I backed it into my neighbor's truck, who had kind of parked in a blind spot behind our driveway because he was using his driveway for something. It was a beat up truck, and he was a funny and sweet old dude who didn't care and just let me come hang out at his pool to pretend I was working it off so my parents would shut up about it.
Well, my brother caught wind of this and blackmailed me. In hindsight, it wouldn't have been a big deal. Neighbor was cool, my parents were friends with him (he just knew they were...uhm...a little psycho), and I could have paid some money or done some yard work. But to my teenaged self with my first car, this counted as some sort of felony - I had misused the first expensive adult thing I ever had. So I was terrified.
He blackmailed me to basically drive him and his fuckup friend everywhere for two years. I remember my mom gushing about how he and I were so close and hung out together all the time.
2 years later, I passed on this car to him before I went to college. I was in the process of buying an old ass SUV from other neighbors so I could move myself to college, and was borrowing my dad's fairly nice car to drive myself to work. Because I like revenge, I parked my dad's car in that same blind spot and my brother NAILED it with what was now his car. My dad has never, EVER stopped talking about this, and my brother had to work it off FOREVER.
Apparently when my brother was just barely walking age, I used to tie his wrists up and lead him around with a rope and pretend he was my prisoner. Apparently.
So what kind of awful shit did you and your siblings do to each other?