In the first grade, I was bullied by a popular kid in my school.

Back in those days (early '90s), the cool thing was to have pencil grips. Kids loved to show off an assortment of colors and styles of them. This bully of mine happened to have a single pencil, covered from tip to eraser with pencil grips, which was his prize possession. He was always showing it off to everyone. It was rumored he’d been stealing them off other kids, but no one could definitively prove it.

When he wasn’t looking one day, I snatched his favorite pencil with all the pencil grips. It was justice for all the times he picked on me in grade school. I enjoyed watching him frantically turn his backpack inside out, trying to find it.

I didn’t get to keep it for long, though. A week later, one of the stricter teachers found it in my backpack and told me I had too many pencil grips for a single pencil, so she confiscated it. I didn’t know any better at the time, or else I would’ve complained about her stealing my property. But it was already stolen, so I didn’t really care to fight it.

That was the first and last time I stole something. I actually agonized over it for a long time afterward. I was relieved when the teacher stole it from me because it was finally out of my hands and I didn’t have to worry about it anymore. I never stole anything else again; the anxiety of holding onto stolen goods etched itself deep into my psyche.

Also calling out my sister: When I was maybe 6 or so, my mother found a stash of candy in a cabinet of our kitchen; mostly Lifesavers. She asked me where it came from and I just shrugged. She then asked my sister, who was 2 years younger than me, and my sis immediately broke down crying. Turns out, every time my mother went to the gas station, my little sis would grab a couple rolls of Lifesavers and pocket them. She thought my parents would never look in the messy cabinets of our kitchen.

I'm pretty sure she never stole again after getting caught. She was a wreck for a while afterward and almost terrified of candy when offered.

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.

In my teens, I stole some CDs. This was pre-napster. I didn’t have money to spend bit it’s hard to deny the importance of music to people, especially in those formative years. I only took 2 maybe 3 total, because the guilt of taking it a CD each time wasn’t worth it.

To give you an idea of how much guilt, I don’t like people offering me food… Because it was theirs and now it’s not. The fact they offered it means nothing. (Of course, the reverse isn’t true)

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.

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.

It was a red and green plastic pencil sharpener shaped like a dachshund. You stuck your pencil in his butt. I stole it from a desk in Sunday School. I stole from God.

I accidentally took a screwdriver from Sears as a toddler. Been stealing screwdrivers every day since /s

Nice try, corporate!

A newspaper.

Did not know it was stealing… I was … maybe 7?

Up until that point in my life, I’d only ever been to stores or restaurants that had free flyers or small community newsletters.

First time I was in a similar small store, I assumed full, 30+ page newspapers worked the same way.

After being informed that full newspapers cost money, and I had stolen it, I returned it.

The store clerk did not even realize I had taken the paper, laughed, appreciated my honesty, and gave me a tootsie pop.

When I was a teenager I once started reading a newspaper and walked out of a grocery store, not realizing you had to pay for them. I was distressed and one of my parents called the store and explained the situation and we paid for the newspaper the next time we went in.

When I was a small child, I once ate a gummy between the bulk candy bins. When explained later that you aren’t just allowed to take the candy and you have to pay for it, I panicked.

Neither of these were intentional thefts, but maybe they count.

A tiny dinosaur eraser when I was like 6 or 7?

I stole a pen once, by accident

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.

M:tG cards back in the late 90s.

There was a local comic book store called (no shit) The Funk Pit, which kept the mid tier cards stored in 3 ring binders full of those plastic card sleeves, and common cards stored in an “Inch Box” where they just charged you by the height of your stack. My friend and I would occasionally sneak a more expensive card out of the binder and slip it into our stack from the Inch Deck that cost $1.25.

There’s no way we were the first or last to do it, but I felt kinda shitty about it for years after.

A bottle from mad dog 20/20 from a gas station. I was like 15. Me and some buddies wanted to get drunk, none of us had fake IDs, and the weed dealer who normally supplied the booze wasn’t answering his phone. 5 of us went in, my buddy Brian volunteered to be tribute, and he grabbed a case of beer and just went to walk out the door with it. While the clerk was distracted dealing with that, we shoved mad dog in our pockets, and then went to the register with sodas. Brian dropped the case of beer and booked it. It was a very smooth operation.

Didn’t steal anything else for years, until I was like 18, and we were so poor that my mom and I started shoplifting out of genuine necessity, while waiting on her disability to kick in.