I stole a snickers bar when I was like 5. My mom knew before I got home. She kicked my ass when I got home.

I read a YA book about someone methodically planning, then stealing a computerized chess board (a big deal in the 80's/early 90's). They recorded people saying different words for the audio message telling the clerk to lock themself in the BATHROOM, timed it out, etc. While this obviously wasn't me, it always stuck with me, and I somehow got secondhand guilt from it...

Sweets, then upgraded to lighters

I stole a pen once, by accident

Idk if it was the first but I stole a bunch of pens from one of my teachers after i found out she was fired.

I think it was something like $30 out of my brother's wallet. Boy did I get in trouble for that one. In my defense, he had just left it lying on top of his bed's side table! You can't expect a five year old to not steal $30 out of a wallet just lying on a side table in a room with a closed door!

I don't even know what I spent it on, thinking back. Probably those little styrofoam airplanes you could put together from the little store out in the country that was nearby.

I saw a grey snubnose pistol toy somebody left lying around at a rental shop when I was like... 5? It was exactly like the one I had, but mine was green and I wanted the realistic grey. Felt so bad about it once I got home that I hid it and never touched it, and then it eventually went missing.

Cannot recall the first thing, but I at least know my brother got a PSP the one and only time he ever stole money from my parents. Back when those were still relevant.

Edit:

Thinking about it, probably some time off my parents life from before I was even born. Doctors did variously tests and I was supposed to be the special needs child of the family. Worst I got was a case of high functioning autism. They definitely would have taken on the challenge of raising me, but I can almost guarantee they worried enough about me that I took some time off their lives.

There was a candy machine at my local grocery store's front lobby, and when I was around 8-9, my friend and I noticed that the top of the machine wasn't attached properly. We removed the top and filled our pockets with candy. Unfortunately, I told my brother about it who told my parents who made me go apologise to the store owner

The joy and boredom of growing up in a small town

Kisses?

I was like 7 and wanted some disks for a Bionicle, but I didn't want to hold onto it the entire time while looking at toys. So I put it in my pocket... and forgot about it.