The first thing was probably a set of earrings when I was a really little guy. I handed them to my mom when we got home and she was shocked at what a smooth swipe I pulled and we immediately went back to return them. So much for my thoughtful gift! Hahaha.

I also recall this thing at my very conserva-religious elementary school, where people set up a little market selling things as gifts and such. I was given some money to go buy presents for people, but nobody told me how to pay for anything, and I assumed it was like a big box store where you pay at the end.

So here I am like, what, 6 or 7 maybe? Going from table to table and just yoinking knick-knacks into my little bag. Nobody stopped me or otherwise corrected me. I still don’t see anywhere to “check out”! I end up just leaving, basically.

Cut to me waiting in the lunch line and just getting straight up shaken down and accosted for cash by some authoritarian staff types. I just handed them the bag of spending money I’d been supplied with and I don’t really remember what happened after that. Looking back though, those people were very mean to a confused child under 10, treating me like some deliberate criminal mastermind of petty-thievery lol.

I nicked a LEGO winch brick from primary school and my gran made me take it back. Not a criminal mastermind.

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 walking it with the 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)

When I went to malls as a teenager I would often get stopped and searched as if I was shoplifting. Was over 6’ at 16 and often wore hoodies. When I started getting into cross-dressing I was too ashamed to go through checkout with it. So I dressed in nicer clothes then hoodie and jeans, and shoplifted women’s clothing from every clothing store that ever stopped and searched me incorrectly previously. Part shame part revenge part kink.

I stole so many books as a kid. The library didn’t have books on Wicca and Paganism so I stole them from Waldenbooks.

Some loose change from my dad to buy lunch at school.

Sweets, then upgraded to lighters

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

I stole a pen once, by accident

Stole some clothes from Hot Topic; had to remove the ink tags later by hand. I skipped school with my crush at the time and it was a rush.

Not that I remember but apparently when I was 2 yrs old or so I snatched a handful of very expensive wedding cake from a bakery display window while my dad was busy paying at the counter. He noticed when picking me up to leave and godspeed back home because he couldn’t afford paying the now damaged cake.

The first and only thing I remember stealing was a monkey toy when I was 3 or 4 yrs. Went to a party or something at someone’s house, there were other kids there and I decided I deserved that monkey more than they did so I pocketed it. My parents found out afterwards, they weren’t happy about it but didn’t care enough to return the toy to the owner. I guess it was a cheap toy.

In 5th grade I discovered that my hand and wrist were small enough to reach up into 25 cent bathroom pad and tampon dispensers. I didn’t really understand what they were for but I thought it was funny to empty them out whenever I saw them.

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.

In kindergarten, a small suction-cup hourglass. The suction cup has already decomposed, but the rest is fine.

Yes, I still have it.
Unlike the pony from MLP (Twilight Sparkle) I had to “borrow” forever to someone else from family because I was a boy and had no business having a “girl toy”. I also stole it in kindergarten. It was small, hard plastic figure coated with some plush-like coating. It was worn off at bottom of the legs.

I still remember it, I didn’t forget. Ironic. What I stole was stolen from me.

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.