I have a memory of doing that 20 years ago as a pre-teen to make my friend like 50 cents.

Many of the adult-oriented ads paid upwards of $0.50/click.

Your parents would definitely wonder why you were receiving checks in the mail from Xpics.

Once I left the Visual Basic scripted web control running overnight by mistake...

I used to do the same thing, but I don't think any of them were adult sites. It was all done through some kind of ads broker, and the cheques came directly from them.

Looking back, it was pretty shitty behaviour by me, but as a 14 year old boy, it just didn't even feel like a crime, even a victimsless one; it almost felt entrepreneurial.

Your 14 year old self learned the core lesson of business success.

Thats how i made my first 10k on the web, still have the check:)