I can't remember my first, I have vague memories of stumbling across Bondage Fairies and seeing short poorly compressed clips ripped from La Blue Girl, but I remember the thing that really got me into hentai was an AMV for Bible Black set to Relax by Frankie Goes to Hollywood.

Slow internet back then so it was just images for me at first, I think. It probably had something to do with the girls from Bleach (these are some of the oldest saved)

>>446 Does that pic even counts as hentai?

Viper GTS, at the time it was the best hentai ova I'd ever seen when I was new to hentai ova's in my early tweens.

>>1090 Barely, back when paheal was more relevant it still had a ton of shit porn flooding it's gallery. Had to wade through a ton of crap to fine good shit. That still is the truth to this day but thankfully tags exist for most booru styled sites like sankaku and others.

Not sure on the unwritten rules so I'm spoiling it for Futanari. But this is what started it all for me.

This is one of the earliest things I remember. I also recall the model viewer in Soul Calibur 3 and Tekken 5. Plus, I remember getting hard over some Sega and PS1 games, though back then I had no clue what was going on. Back in 2003, a classmate handed me a floppy disk loaded with Flintstones and Jetsons porn, and yeah, I got a lot of use out of it. Spoilered for bestiality

>>6693 The rules aren't unwritten. They're in two places, and one of those places is a pinned thread. But yes, futa should be spoilered outside a futa thread, and generally not dumped en masse even if spoilered outside a futa thread, so your intuition is right.

Found this in an ftp directory when I was 13. I've frequently deep dived to find it again ever since.