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.

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)

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

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.

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

A prop gift in a store after holiday season. It was just about tiny enough to fit in my pocket. Imagine my disappointment when I tore off the wrapping paper and found a cube of Styrofoam. I was like 5 at the time.

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.

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.

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

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

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.

Does software piracy count?

Ah who am I kidding, of course it doesn’t.